Realestateinthefloridakeys.com Search Results

A rare opportunity to own a beautifully renovated historic property on coveted Fleming Street in the heart of Old Town Key West. Thoughtfully designed and renovated with exceptional craftsmanship, this unique property offers 7 bedrooms and 6 baths, creating an extraordinary combination of flexibility, privacy, and Old Town charm. The property is comprised of a 5-bedroom, 4-bath main residence, a separate one-bedroom guest apartment, and a one-bedroom pool cottage, each offering its own living space and kitchen. The guest apartment provides the perfect private quarters for visiting family and friends, or could easily be incorporated into the main residence to create additional living space or an expansive primary suite. The detached pool cottage offers yet another private retreat or rental opportunity. Outdoor living is at the heart of this exceptional property. A secluded, lushly landscaped entertaining area features a lagoon-style heated saltwater pool, tiki bar, and outdoor shower - an ideal setting for relaxing afternoons, sunset cocktails, and entertaining guests. Front and rear balconies provide additional opportunities to enjoy the quintessential Key West lifestyle, from morning coffee to evening cocktails. A private off-street parking space adds an especially valuable convenience in Old Town. Inside, the renovation reflects an exceptional level of craftsmanship and attention to detail, with beautiful finishes and crown molding throughout. Just a few blocks from the energy of Duval Street, the Historic Seaport and all that Old Town Key West has to offer, yet designed to provide a private oasis when you return home. A truly special property with endless possibilities for living, entertaining, and enjoying the Key West lifestyle. Owner is a licensed Florida Real Estate agent.

7 Beds ⋅ 6 Baths ⋅ 621882 MLS

A rare opportunity to own a beautifully renovated historic property on coveted Fleming Street in the heart of Old Town Key West. Thoughtfully designed and renovated with exceptional craftsmanship, this unique property offers 7 bedrooms and 6 baths, creating an extraordinary combination of flexibility, privacy, and Old Town charm. The property is comprised of a 5-bedroom, 4-bath main residence, a separate one-bedroom guest apartment, and a one-bedroom pool cottage, each offering its own living space and kitchen. The guest apartment provides the perfect private quarters for visiting family and friends, or could easily be incorporated into the main residence to create additional living space or an expansive primary suite. The detached pool cottage offers yet another private retreat or rental opportunity. Outdoor living is at the heart of this exceptional property. A secluded, lushly landscaped entertaining area features a lagoon-style heated saltwater pool, tiki bar, and outdoor shower - an ideal setting for relaxing afternoons, sunset cocktails, and entertaining guests. Front and rear balconies provide additional opportunities to enjoy the quintessential Key West lifestyle, from morning coffee to evening cocktails. A private off-street parking space adds an especially valuable convenience in Old Town. Inside, the renovation reflects an exceptional level of craftsmanship and attention to detail, with beautiful finishes and crown molding throughout. Just a few blocks from the energy of Duval Street, the Historic Seaport and all that Old Town Key West has to offer, yet designed to provide a private oasis when you return home. A truly special property with endless possibilities for living, entertaining, and enjoying the Key West lifestyle. Owner is a licensed Florida Real Estate agent.

923 Fleming St, Key West

$5,295,000

A truly rare opportunity in the Florida Keys! Welcome to 554 Ocean Cay, an exceptional oceanfront building lot located within an exclusive gated community in Port Largo, Key Largo. What makes this property so extraordinary is its unique combination of direct Atlantic Ocean frontage in the backyard and 100 feet of deep-water dockage in the front, offering direct ocean access and the ability to accommodate yachts up to 100 feet. BEST OF ALL, THIS LOT WAS PREVIOUSLY IMPROVED WITH A HOME, OFFERING A SIGNIFICANT ADVANTAGE FOR BUYERS LOOKING TO BUILD WITHOUT THE TYPICAL WAIT ASSOCIATED WITH VACANT LAND IN THE FLORIDA KEYS! Very few properties in the entire Florida Keys offer this remarkable combination of oceanfront living, deep-water yacht dockage, and an existing residential building history. Imagine designing your custom waterfront estate overlooking the open Atlantic Ocean while keeping your yacht just steps from your front door. Enjoy breathtaking ocean views, exceptional boating access, and the privacy of an exclusive gated community. For the discerning buyer seeking a truly unique location to create a magnificent Florida Keys estate, opportunities like this are increasingly difficult to find. Two waterfront experiences, one extraordinary property. This is Florida Keys living at its finest!

621722 MLS

A truly rare opportunity in the Florida Keys! Welcome to 554 Ocean Cay, an exceptional oceanfront building lot located within an exclusive gated community in Port Largo, Key Largo. What makes this property so extraordinary is its unique combination of direct Atlantic Ocean frontage in the backyard and 100 feet of deep-water dockage in the front, offering direct ocean access and the ability to accommodate yachts up to 100 feet. BEST OF ALL, THIS LOT WAS PREVIOUSLY IMPROVED WITH A HOME, OFFERING A SIGNIFICANT ADVANTAGE FOR BUYERS LOOKING TO BUILD WITHOUT THE TYPICAL WAIT ASSOCIATED WITH VACANT LAND IN THE FLORIDA KEYS! Very few properties in the entire Florida Keys offer this remarkable combination of oceanfront living, deep-water yacht dockage, and an existing residential building history. Imagine designing your custom waterfront estate overlooking the open Atlantic Ocean while keeping your yacht just steps from your front door. Enjoy breathtaking ocean views, exceptional boating access, and the privacy of an exclusive gated community. For the discerning buyer seeking a truly unique location to create a magnificent Florida Keys estate, opportunities like this are increasingly difficult to find. Two waterfront experiences, one extraordinary property. This is Florida Keys living at its finest!

554 Ocean Cay Dr, Key Largo

$5,200,000

Stunning brand-new waterfront estate offering 6 bedrooms and 8 bathrooms with modern designs and luxury finishes throughout. The gourmet kitchen features premium Sub-Zero appliances and flows seamlessly into spacious living and entertaining areas. Built for long-term durability with a metal roof, solar panels, and a water cistern system. Enjoy resort-style outdoor living with a custom pool, covered lounge areas, and a 55-foot private dock with a garage and tackle room, perfect for boaters and fishing enthusiasts. Experience the best of modern waterfront living in Key Largo. House is completely fenced not shown on pictures because all fencing is new.

6 Beds ⋅ 8 Baths ⋅ 621737 MLS

Stunning brand-new waterfront estate offering 6 bedrooms and 8 bathrooms with modern designs and luxury finishes throughout. The gourmet kitchen features premium Sub-Zero appliances and flows seamlessly into spacious living and entertaining areas. Built for long-term durability with a metal roof, solar panels, and a water cistern system. Enjoy resort-style outdoor living with a custom pool, covered lounge areas, and a 55-foot private dock with a garage and tackle room, perfect for boaters and fishing enthusiasts. Experience the best of modern waterfront living in Key Largo. House is completely fenced not shown on pictures because all fencing is new.

259 Saint Thomas Ave, Key Largo

$5,200,000

Prime Commercial Property in Iconic Key West - High Visibility & Versatility! This property offers a rare opportunity to own a substantial commercial footprint in one of Florida's most iconic destinations. Whether you're expanding a brand, launching a new concept, or investing in Key West's vibrant market, 3424 N Roosevelt Blvd is a strategic asset with flexible potential. Location Highlights include: • Strategic Location - Located on Key West's main commercial corridor • Proximity - 7 minutes (2.5 miles) to Key West International Airport • Exceptional Visibility - High traffic exposure from both locals and tourists • Surrounded by Amenities -Including hotels, restaurants, banks, shops, fitness centers, and grocery stores. Property Details • Building Square Footage: 3,420 sq ft • Building w/ Tiki: 7,491 sq ft • Lot Square Footage: 36,002 sq ft • Frontage: 155 feet Current Use • Vehicle - Rentals Currently operates as a successful vehicle rental business. • Service Department - Features a care center with six service bays. Business Opportunity sold separately, inquire with agent.

3 Baths ⋅ 617330 MLS

Prime Commercial Property in Iconic Key West - High Visibility & Versatility! This property offers a rare opportunity to own a substantial commercial footprint in one of Florida's most iconic destinations. Whether you're expanding a brand, launching a new concept, or investing in Key West's vibrant market, 3424 N Roosevelt Blvd is a strategic asset with flexible potential. Location Highlights include: • Strategic Location - Located on Key West's main commercial corridor • Proximity - 7 minutes (2.5 miles) to Key West International Airport • Exceptional Visibility - High traffic exposure from both locals and tourists • Surrounded by Amenities -Including hotels, restaurants, banks, shops, fitness centers, and grocery stores. Property Details • Building Square Footage: 3,420 sq ft • Building w/ Tiki: 7,491 sq ft • Lot Square Footage: 36,002 sq ft • Frontage: 155 feet Current Use • Vehicle - Rentals Currently operates as a successful vehicle rental business. • Service Department - Features a care center with six service bays. Business Opportunity sold separately, inquire with agent.

3424 N Roosevelt Blvd, Key West

$5,200,000

Introducing Blue Sky Pointe - the crown jewel of Sugarloaf Key. Perched on a gated 33,750 sq. ft. peninsula with approximately 730 feet of waterfront, this spectacular 4 Bed, 3.5 Bath modern coastal showpiece is surrounded by glistening water and enjoys Keys famous sunset views over Sugarloaf Sound. Fully renovated with premium craftsmanship, the home features a standing seam metal roof, PGT impact windows/doors, and Hardi board siding. Inside, enjoy a sunlit open-concept floor plan with soaring ceilings, a gourmet kitchen with quartz counters, premium stainless appliances, gas stove, a hidden butler's pantry, and a waterfront Bedroom wing, all oriented to frame the water from every room. Step outside and immerse yourself in resort-style living with a heated and chilled waterfront pool, soothing spa, hot tub, invigorating cold plunge, and a fire pit encircled by flickering tiki torches to gather with friends and family while sipping cocktails as the sun melts into the horizon. Lounge on the expansive covered porch while enjoying views of the peaceful nature preserve for incredible bird watching, and a setting that offers total privacy and serenity. Boaters will love the protected canal access with 2 boat lifts (8K & 12K lbs), just minutes from open water. Additional features include a 4-car garage with EV charger, covered RV Tiki with 50 amp service, whole-house 35kW generator (750-gal tank), whole house water softening system and Sonos throughout, including garage and outdoor zones. Whether you're seeking a private sanctuary, a trophy lot, or the ultimate Florida Keys lifestyle, Blue Sky Pointe delivers. This is the most premiere lot on Sugarloaf Key — a once-in-a-lifetime opportunity.

4 Beds ⋅ 4 Baths ⋅ 618184 MLS

Introducing Blue Sky Pointe - the crown jewel of Sugarloaf Key. Perched on a gated 33,750 sq. ft. peninsula with approximately 730 feet of waterfront, this spectacular 4 Bed, 3.5 Bath modern coastal showpiece is surrounded by glistening water and enjoys Keys famous sunset views over Sugarloaf Sound. Fully renovated with premium craftsmanship, the home features a standing seam metal roof, PGT impact windows/doors, and Hardi board siding. Inside, enjoy a sunlit open-concept floor plan with soaring ceilings, a gourmet kitchen with quartz counters, premium stainless appliances, gas stove, a hidden butler's pantry, and a waterfront Bedroom wing, all oriented to frame the water from every room. Step outside and immerse yourself in resort-style living with a heated and chilled waterfront pool, soothing spa, hot tub, invigorating cold plunge, and a fire pit encircled by flickering tiki torches to gather with friends and family while sipping cocktails as the sun melts into the horizon. Lounge on the expansive covered porch while enjoying views of the peaceful nature preserve for incredible bird watching, and a setting that offers total privacy and serenity. Boaters will love the protected canal access with 2 boat lifts (8K & 12K lbs), just minutes from open water. Additional features include a 4-car garage with EV charger, covered RV Tiki with 50 amp service, whole-house 35kW generator (750-gal tank), whole house water softening system and Sonos throughout, including garage and outdoor zones. Whether you're seeking a private sanctuary, a trophy lot, or the ultimate Florida Keys lifestyle, Blue Sky Pointe delivers. This is the most premiere lot on Sugarloaf Key — a once-in-a-lifetime opportunity.

17013 Coral Dr, Sugarloaf

$5,200,000

This Large property is on the Oceanside of Downtown Key Largo with 500 ft of concrete Deep Water Dockage that has direct ocean access. 5 combined lots of 100 x 125 ft each, where most lots in Port Largo are only 75 ft. X 125. There is a 5,508 sq. ft. concrete building with concrete roof that is commercially zoned. Sale includes the commercial building, and over 62,000 sq. ft. of land that has gas and diesel tanks on the property and a sewage pump out to service boats. Currently 3 tenants are in place with active leases. This is a rare opportunity of an Iconic Key Largo Property. Please DO NOT walk the property or bother the tenants.

4 Baths ⋅ 612573 MLS

This Large property is on the Oceanside of Downtown Key Largo with 500 ft of concrete Deep Water Dockage that has direct ocean access. 5 combined lots of 100 x 125 ft each, where most lots in Port Largo are only 75 ft. X 125. There is a 5,508 sq. ft. concrete building with concrete roof that is commercially zoned. Sale includes the commercial building, and over 62,000 sq. ft. of land that has gas and diesel tanks on the property and a sewage pump out to service boats. Currently 3 tenants are in place with active leases. This is a rare opportunity of an Iconic Key Largo Property. Please DO NOT walk the property or bother the tenants.

522 Caribbean Dr, Key Largo

$5,195,000

Double waterfront MM 2 in Key West. Presenting a rare opportunity to acquire a distinguished single-family waterfront home on highly desired Hilton Haven Drive, a truly unique private Key West Street with everything from a luxury resort and high-end properties to houseboats. This spectacular residence is a true gem facing both South and North. On the south side, enjoy sweeping decks, a waterfront pool, 15,000 lb. boat lift and convenient dock overlooking the Key West Yacht Club and Garrison Bight. On the north side, enjoy unencumbered views from the serene, covered entry porch of the Gulf of Mexico with a deeded 75' by 300' bay bottom parcel. Upon entering through the handsome oversized wooden doors, you are greeted by the living room's custom hand built beamed wood cathedral ceiling and a majestic staircase. The sunroom features French doors that open to views of the pool and harbor. The expansive backyard includes a covered dining area, a 45' waterfront deck overlooking the dock and boat lift. The chef's kitchen is designed for entertaining, equipped with ample counter space, Viking appliances, and a Fisher Paykel cooktop. The first-floor primary suite opens to a rear private deck and dock. Completing the first floor is the laundry room, half-bath, full bath, and a charming guest bedroom. The sunroom with wet bar and bathroom provides access to the one car garage, and second staircase leading to the second floor office with custom wood paneling, cabinetry, a full bath and deck with views of the Florida Bay and Garrison Bight. The second floor provides a bonus game room and hosts two additional bedrooms connected by a beautiful bathroom. Throughout this meticulously renovated residence, the present owner has incorporated vaulted ceilings on all levels, custom woodwork, and built-ins, creating a truly spectacular living space. The property must be seen to truly appreciate it. https://show.tours/v/2qnvjWF

5 Beds ⋅ 6 Baths ⋅ 621709 MLS

Double waterfront MM 2 in Key West. Presenting a rare opportunity to acquire a distinguished single-family waterfront home on highly desired Hilton Haven Drive, a truly unique private Key West Street with everything from a luxury resort and high-end properties to houseboats. This spectacular residence is a true gem facing both South and North. On the south side, enjoy sweeping decks, a waterfront pool, 15,000 lb. boat lift and convenient dock overlooking the Key West Yacht Club and Garrison Bight. On the north side, enjoy unencumbered views from the serene, covered entry porch of the Gulf of Mexico with a deeded 75' by 300' bay bottom parcel. Upon entering through the handsome oversized wooden doors, you are greeted by the living room's custom hand built beamed wood cathedral ceiling and a majestic staircase. The sunroom features French doors that open to views of the pool and harbor. The expansive backyard includes a covered dining area, a 45' waterfront deck overlooking the dock and boat lift. The chef's kitchen is designed for entertaining, equipped with ample counter space, Viking appliances, and a Fisher Paykel cooktop. The first-floor primary suite opens to a rear private deck and dock. Completing the first floor is the laundry room, half-bath, full bath, and a charming guest bedroom. The sunroom with wet bar and bathroom provides access to the one car garage, and second staircase leading to the second floor office with custom wood paneling, cabinetry, a full bath and deck with views of the Florida Bay and Garrison Bight. The second floor provides a bonus game room and hosts two additional bedrooms connected by a beautiful bathroom. Throughout this meticulously renovated residence, the present owner has incorporated vaulted ceilings on all levels, custom woodwork, and built-ins, creating a truly spectacular living space. The property must be seen to truly appreciate it. https://show.tours/v/2qnvjWF

18 Hilton Haven Road, Key West

$5,100,000

OWNER FINANCING AVAILABLE AT 6% Experience luxury waterfront living in the Florida Keys with this exceptional 5 bedroom, 4 bath estate, ideally positioned at the end of a quiet street with 173 feet of deep-water dockage and an expansive turning basin offering easy maneuverability for large boats, performance boats, and large sportfishing vessels. Offered fully furnished and completely move-in ready, this home is designed for effortless Keys living from day one. Furnishings, décor, and thoughtfully selected finishes complement the home's sophisticated design, while the chef's kitchen features a complete suite of premium Thermador appliances. Built for both luxury and durability, the smart home showcases high-end interior finishes and premium composite exterior materials designed for the coastal environment. Features include a private elevator, programmable smart-home hubs throughout, whole-house surround sound extending to the pool and rooftop, and two laundry rooms, one on each living level. Expansive indoor living areas transition seamlessly outdoors to a private resort-style pool with sun shelf and gazebo. Oversized balconies off the primary suite and kitchen overlook the water, capturing spectacular bay sunsets and views of boats passing through iconic Toilet Seat Cut. The nearly 2,000-square-foot rooftop terrace is a true showpiece, complete with turf, bar, BBQ area, immersive audio, and panoramic views. With direct bay access and a short ride to Tavernier Creek for convenient Atlantic Ocean access, this fully furnished waterfront estate delivers boating, entertaining, luxury, and the Florida Keys lifestyle in one extraordinary package.

5 Beds ⋅ 4 Baths ⋅ 621368 MLS

OWNER FINANCING AVAILABLE AT 6% Experience luxury waterfront living in the Florida Keys with this exceptional 5 bedroom, 4 bath estate, ideally positioned at the end of a quiet street with 173 feet of deep-water dockage and an expansive turning basin offering easy maneuverability for large boats, performance boats, and large sportfishing vessels. Offered fully furnished and completely move-in ready, this home is designed for effortless Keys living from day one. Furnishings, décor, and thoughtfully selected finishes complement the home's sophisticated design, while the chef's kitchen features a complete suite of premium Thermador appliances. Built for both luxury and durability, the smart home showcases high-end interior finishes and premium composite exterior materials designed for the coastal environment. Features include a private elevator, programmable smart-home hubs throughout, whole-house surround sound extending to the pool and rooftop, and two laundry rooms, one on each living level. Expansive indoor living areas transition seamlessly outdoors to a private resort-style pool with sun shelf and gazebo. Oversized balconies off the primary suite and kitchen overlook the water, capturing spectacular bay sunsets and views of boats passing through iconic Toilet Seat Cut. The nearly 2,000-square-foot rooftop terrace is a true showpiece, complete with turf, bar, BBQ area, immersive audio, and panoramic views. With direct bay access and a short ride to Tavernier Creek for convenient Atlantic Ocean access, this fully furnished waterfront estate delivers boating, entertaining, luxury, and the Florida Keys lifestyle in one extraordinary package.

265 Pueblo St, Tavernier

$4,999,999

Looking for one of the most unique Bayfront Estates in the Florida keys, well you just found it. Just over 3 acres located on the Gulf of America. What makes the property so unique first and foremost is the privacy it offers. Upon entering the double gate, you are surrounded by huge trees, heavy foliage and vegetation which provides you with complete privacy. There are walking trails all through the entire property, including out to the Bayfront to enjoy some of the most spectacular year round sunsets you will ever see. The property directly to the North is a preserve called, Crane Point Hammock and Museum & Nature Trails. The subject property boasts its own huge boat basin with new custom Ipe wooden dock to accommodate large vessels and/or multiple vessels with two 50 AMP services, all the power you may need. There is a separate dock and slip tucked inside the private boat basin the owner had custom built for his 52 foot Viking Express. There is also a 20,000 pound boat lift and a small boat ramp for your flats skiff. The main home has that Old Florida Charm, three bedrooms, two baths and great room with exposed beams and tongue and groove ceilings. Take the stairs up you your private master retreat with spectacular views overlooking your private basin and the bay. The home also offers three screened lanais with water views. Attached to the main home is a private, separate entrance apartment with bedroom, bathroom and kitchen for complete privacy from the main living quarters. Across the pavered driveway is the detached three car garage and above offers a 1 bedroom, 1 bath, living room and kitchenette. The property is located 1.5 miles South of Marathon International Airport to make it easy for pilots and chartered jets and prop planes to come and go from this one of a kind Estate. Easy access to the Atlantic Ocean. Looking for peace, privacy and serene relaxing Florida Bay and sunsets views? You just found it!!

5 Beds ⋅ 5 Baths ⋅ 621022 MLS

Looking for one of the most unique Bayfront Estates in the Florida keys, well you just found it. Just over 3 acres located on the Gulf of America. What makes the property so unique first and foremost is the privacy it offers. Upon entering the double gate, you are surrounded by huge trees, heavy foliage and vegetation which provides you with complete privacy. There are walking trails all through the entire property, including out to the Bayfront to enjoy some of the most spectacular year round sunsets you will ever see. The property directly to the North is a preserve called, Crane Point Hammock and Museum & Nature Trails. The subject property boasts its own huge boat basin with new custom Ipe wooden dock to accommodate large vessels and/or multiple vessels with two 50 AMP services, all the power you may need. There is a separate dock and slip tucked inside the private boat basin the owner had custom built for his 52 foot Viking Express. There is also a 20,000 pound boat lift and a small boat ramp for your flats skiff. The main home has that Old Florida Charm, three bedrooms, two baths and great room with exposed beams and tongue and groove ceilings. Take the stairs up you your private master retreat with spectacular views overlooking your private basin and the bay. The home also offers three screened lanais with water views. Attached to the main home is a private, separate entrance apartment with bedroom, bathroom and kitchen for complete privacy from the main living quarters. Across the pavered driveway is the detached three car garage and above offers a 1 bedroom, 1 bath, living room and kitchenette. The property is located 1.5 miles South of Marathon International Airport to make it easy for pilots and chartered jets and prop planes to come and go from this one of a kind Estate. Easy access to the Atlantic Ocean. Looking for peace, privacy and serene relaxing Florida Bay and sunsets views? You just found it!!

1590 Pelican Pass, Marathon

$4,995,000

Where Casa Marina Charm Meets Modern Island Living. Set on an expansive 10,000 sq. ft corner lot in prestigious Casa Marina, one of Key West's most sought-after neighborhoods, this fully renovated 4-bedroom, 3-bath residence offers nearly 2,100 sq. ft of thoughtfully designed living space just moments from the Atlantic shoreline and the charm of Old Town. A comprehensive 2020 renovation transformed the home from top to bottom, delivering vaulted ceilings, energy-efficient LED lighting, and all-new hurricane-rated impact windows and doors that fill the interior with natural light. The open floor plan flows effortlessly between living, dining, and kitchen spaces, making it ideal for both everyday living and entertaining. At the heart of the home, the chef's kitchen features top-of-the-line Dacor appliances and custom bespoke cabinetry. The private primary suite is tucked at the rear of the home with an ensuite bath and sliding glass doors that open directly to the lanai. Each additional bedroom includes built-in closets, offering comfort and flexibility for guests or a home office. Outdoors, a custom heated in-ground pool with a soothing water feature is surrounded by elegant travertine decking and a spacious covered patio, creating a private tropical retreat for relaxing or hosting under the Key West sky. The low-maintenance front yard features artificial turf and landscape lighting that showcases the tropical foliage after dark. Peace of mind comes standard with a whole-house generator, 2-zone central A/C with linear vents, and a new standing seam metal roof that may qualify for wind insurance credits. A rare one-car garage and ample off-street parking complete this exceptional Casa Marina offering.

4 Beds ⋅ 3 Baths ⋅ 621521 MLS

Where Casa Marina Charm Meets Modern Island Living. Set on an expansive 10,000 sq. ft corner lot in prestigious Casa Marina, one of Key West's most sought-after neighborhoods, this fully renovated 4-bedroom, 3-bath residence offers nearly 2,100 sq. ft of thoughtfully designed living space just moments from the Atlantic shoreline and the charm of Old Town. A comprehensive 2020 renovation transformed the home from top to bottom, delivering vaulted ceilings, energy-efficient LED lighting, and all-new hurricane-rated impact windows and doors that fill the interior with natural light. The open floor plan flows effortlessly between living, dining, and kitchen spaces, making it ideal for both everyday living and entertaining. At the heart of the home, the chef's kitchen features top-of-the-line Dacor appliances and custom bespoke cabinetry. The private primary suite is tucked at the rear of the home with an ensuite bath and sliding glass doors that open directly to the lanai. Each additional bedroom includes built-in closets, offering comfort and flexibility for guests or a home office. Outdoors, a custom heated in-ground pool with a soothing water feature is surrounded by elegant travertine decking and a spacious covered patio, creating a private tropical retreat for relaxing or hosting under the Key West sky. The low-maintenance front yard features artificial turf and landscape lighting that showcases the tropical foliage after dark. Peace of mind comes standard with a whole-house generator, 2-zone central A/C with linear vents, and a new standing seam metal roof that may qualify for wind insurance credits. A rare one-car garage and ample off-street parking complete this exceptional Casa Marina offering.

1100 Johnson St, Key West

$4,995,000

Welcome to an extraordinary oceanfront residence in the exclusive Casa Caselles community, where two townhomes have been masterfully combined into one spectacular 4,224 sq. ft. luxury retreat. Completely reimagined, this one-of-a-kind home features a private interior elevator with automatic doors accessing all floors, exceptional craftsmanship, and effortless oceanfront and poolside living. Offering 4 en-suite bedrooms, 4.5 baths, 2 expansive living rooms divided by a wall insulated with commercial soundproofing, an exercise room, and a hidden office seamlessly integrated into the custom kitchen, the residence is designed for everyday comfort and grand-scale entertaining. The chef's kitchen centers around an oversized island with custom European-style cabinetry, premium quartz countertops, a BlueStar gas range, paneled Sub-Zero refrigerator, Cove dishwasher, U-Line ice maker, wine refrigerator, and Perlick refrigerator/freezer drawers. The family room includes an electric fireplace and custom wet bar with refrigerator drawers, dishwasher, and built-in cabinetry. Travertine flooring, custom built-ins, hidden storage, recessed lighting, remote-controlled window coverings, and in-wall TV wiring reflect meticulous attention to detail. Every major system has been replaced, including electrical, plumbing, insulation, and HVAC. Twelve balconies and hurricane-rated sliding glass doors provide beautiful light in every room, while a whole-house generator provides peace of mind. The luxurious primary suite offers a custom walk-in closet, and every bedroom has private balcony access. A guest suite includes a zero-entry shower for added comfort and accessibility. Tiled courtyards, expanded entertaining terraces, covered parking for four vehicles, an outdoor shower, and multiple laundry areas enhance daily living. Residents also enjoy an oceanfront pool overlooking the Atlantic, completing one of Key West's most distinctive waterfront residences.

4 Beds ⋅ 5 Baths ⋅ 620618 MLS

Welcome to an extraordinary oceanfront residence in the exclusive Casa Caselles community, where two townhomes have been masterfully combined into one spectacular 4,224 sq. ft. luxury retreat. Completely reimagined, this one-of-a-kind home features a private interior elevator with automatic doors accessing all floors, exceptional craftsmanship, and effortless oceanfront and poolside living. Offering 4 en-suite bedrooms, 4.5 baths, 2 expansive living rooms divided by a wall insulated with commercial soundproofing, an exercise room, and a hidden office seamlessly integrated into the custom kitchen, the residence is designed for everyday comfort and grand-scale entertaining. The chef's kitchen centers around an oversized island with custom European-style cabinetry, premium quartz countertops, a BlueStar gas range, paneled Sub-Zero refrigerator, Cove dishwasher, U-Line ice maker, wine refrigerator, and Perlick refrigerator/freezer drawers. The family room includes an electric fireplace and custom wet bar with refrigerator drawers, dishwasher, and built-in cabinetry. Travertine flooring, custom built-ins, hidden storage, recessed lighting, remote-controlled window coverings, and in-wall TV wiring reflect meticulous attention to detail. Every major system has been replaced, including electrical, plumbing, insulation, and HVAC. Twelve balconies and hurricane-rated sliding glass doors provide beautiful light in every room, while a whole-house generator provides peace of mind. The luxurious primary suite offers a custom walk-in closet, and every bedroom has private balcony access. A guest suite includes a zero-entry shower for added comfort and accessibility. Tiled courtyards, expanded entertaining terraces, covered parking for four vehicles, an outdoor shower, and multiple laundry areas enhance daily living. Residents also enjoy an oceanfront pool overlooking the Atlantic, completing one of Key West's most distinctive waterfront residences.

1616 Atlantic Blvd Unit 11, Key West

$4,950,000

DUAL TRANSIENT LICENSES | A RARE DEPARTURE FROM THE ORDINARY While most Old Town properties embrace tropical pastels and wooden shutters, this exceptional compound stands as a bold architectural departure. With its striking modern aesthetic, raw concrete elements, and serene private courtyard, this is where minimalist design meets maximum investment potential, just one block from Duval Street. | THE COMPOUND | Built in 2008 on a generous 5,220sf lot, this 2,441sf property features two distinct units, a front house and back house, connected by a heated pool oasis. Four bedrooms, four full baths, soaring two-story ceilings, and thoughtfully curated interiors showcase warm mid-century touches against clean architectural lines. Wood and tile floors, built-in cabinetry, walk-in closets, and abundant natural light through expansive glass doors create spaces that are both meditative and functional. | THE SANCTUARY | High privacy walls enclose a tranquil pool courtyard with tropical landscaping, outdoor shower, and ample off-street parking. Electric gate entry ensures complete seclusion while downtown's energy pulses just steps away. | THE OPPORTUNITY | Two active transient rental licenses with 1-day minimum stays unlock exceptional income in Key West's most sought-after location. The property's distinctive design aesthetic attracts discerning guests seeking something different, proven by outstanding reviews and strong rental performance. HNC zoning supports flexible commercial use, while X flood zone designation offers insurance advantages. | THE LOCATION | Heart of Old Town, steps from Duval's legendary dining, nightlife, galleries, and waterfront. Close enough to all the action, far enough from the noise. This is investment-grade real estate with soul, where architectural distinction drives premium rates and occupancy.

4 Beds ⋅ 4 Baths ⋅ 621632 MLS

DUAL TRANSIENT LICENSES | A RARE DEPARTURE FROM THE ORDINARY While most Old Town properties embrace tropical pastels and wooden shutters, this exceptional compound stands as a bold architectural departure. With its striking modern aesthetic, raw concrete elements, and serene private courtyard, this is where minimalist design meets maximum investment potential, just one block from Duval Street. | THE COMPOUND | Built in 2008 on a generous 5,220sf lot, this 2,441sf property features two distinct units, a front house and back house, connected by a heated pool oasis. Four bedrooms, four full baths, soaring two-story ceilings, and thoughtfully curated interiors showcase warm mid-century touches against clean architectural lines. Wood and tile floors, built-in cabinetry, walk-in closets, and abundant natural light through expansive glass doors create spaces that are both meditative and functional. | THE SANCTUARY | High privacy walls enclose a tranquil pool courtyard with tropical landscaping, outdoor shower, and ample off-street parking. Electric gate entry ensures complete seclusion while downtown's energy pulses just steps away. | THE OPPORTUNITY | Two active transient rental licenses with 1-day minimum stays unlock exceptional income in Key West's most sought-after location. The property's distinctive design aesthetic attracts discerning guests seeking something different, proven by outstanding reviews and strong rental performance. HNC zoning supports flexible commercial use, while X flood zone designation offers insurance advantages. | THE LOCATION | Heart of Old Town, steps from Duval's legendary dining, nightlife, galleries, and waterfront. Close enough to all the action, far enough from the noise. This is investment-grade real estate with soul, where architectural distinction drives premium rates and occupancy.

720d Simonton St, Key West

$4,950,000

Introducing - Casa Del Mar Estate - this exceptional new home offers a rare level of privacy, scale, and waterfront living on an expansive 26,000+ square foot lot accessed by a private road. Designed to take full advantage of its spectacular setting, the property enjoys unobstructed ocean views and an effortless connection between the residence and the surrounding water. The main living quarters offer four bedrooms and three bathrooms, complemented by substantial finished storage space on the lower level. Built with quality and longevity in mind, the residence features impact-resistant windows and doors, a durable metal roof, concrete construction, and premium finishes throughout, offering the ideal combination of style, security, and peace of mind for waterfront living in the Florida Keys. Beyond the residence, the grounds have been thoughtfully designed for refined outdoor living and entertaining, with a resort-style pool positioned directly toward the ocean and a beautifully appointed gazebo creating the perfect setting for sunset gatherings and private celebrations. An outdoor kitchen, pool table, and table tennis area further extend the living space outdoors, creating an environment equally suited to relaxed afternoons with family or elegant entertaining with guests. The waterfront experience is equally impressive, with generous dockage and a new 20,000-pound boat lift, providing exceptional convenience for boating. Two substantial outdoor sheds offer additional storage for boat side essentials, tools, fishing equipment, and water toys, while the expansive grounds provide something rarely found in the Keys: meaningful room for future expansion. A generous portion of the property remains available for new owners to reimagine and potentially add a guest house, A rare combination of privacy, expansive oceanfront grounds, unobstructed views, exceptional boating amenities, and future expansion potential, offering the ultimate Florida Keys lifestyle.

4 Beds ⋅ 3 Baths ⋅ 621424 MLS

Introducing - Casa Del Mar Estate - this exceptional new home offers a rare level of privacy, scale, and waterfront living on an expansive 26,000+ square foot lot accessed by a private road. Designed to take full advantage of its spectacular setting, the property enjoys unobstructed ocean views and an effortless connection between the residence and the surrounding water. The main living quarters offer four bedrooms and three bathrooms, complemented by substantial finished storage space on the lower level. Built with quality and longevity in mind, the residence features impact-resistant windows and doors, a durable metal roof, concrete construction, and premium finishes throughout, offering the ideal combination of style, security, and peace of mind for waterfront living in the Florida Keys. Beyond the residence, the grounds have been thoughtfully designed for refined outdoor living and entertaining, with a resort-style pool positioned directly toward the ocean and a beautifully appointed gazebo creating the perfect setting for sunset gatherings and private celebrations. An outdoor kitchen, pool table, and table tennis area further extend the living space outdoors, creating an environment equally suited to relaxed afternoons with family or elegant entertaining with guests. The waterfront experience is equally impressive, with generous dockage and a new 20,000-pound boat lift, providing exceptional convenience for boating. Two substantial outdoor sheds offer additional storage for boat side essentials, tools, fishing equipment, and water toys, while the expansive grounds provide something rarely found in the Keys: meaningful room for future expansion. A generous portion of the property remains available for new owners to reimagine and potentially add a guest house, A rare combination of privacy, expansive oceanfront grounds, unobstructed views, exceptional boating amenities, and future expansion potential, offering the ultimate Florida Keys lifestyle.

143 Dorsett Dr, Marathon

$4,950,000

Exceptional commercial waterfront opportunity in the heart of Marathon. This prime commercial property consists of five contiguous lots totaling approximately 30,000 square feet, with 300' on Coco Plum Dr and 300 feet of waterfront. The property includes 18 boat slips with a control depth of approximately 5 feet, offering outstanding maritime access and functionality. Zoned MU-M (Multi-Use Maritime), this versatile zoning allows for a broad range of uses including maritime industry operations such as fishing equipment sales and service, seafood processing, marine-related manufacturing, and boat storage. Additional permitted uses include retail, restaurant, affordable housing, and residential development, making this a uniquely flexible investment property. Parcel IDs include: 00362930, 00362940, 00362950, 00362960, and 00362970. The seller will provide a complete list of all personal property included in the sale, including major furniture, fixtures, and equipment. This is a rare opportunity to acquire a substantial, high-exposure commercial property with extensive waterfront and mixed-use potential in one of the most desirable areas of the Florida Keys.

1 Baths ⋅ 614960 MLS

Exceptional commercial waterfront opportunity in the heart of Marathon. This prime commercial property consists of five contiguous lots totaling approximately 30,000 square feet, with 300' on Coco Plum Dr and 300 feet of waterfront. The property includes 18 boat slips with a control depth of approximately 5 feet, offering outstanding maritime access and functionality. Zoned MU-M (Multi-Use Maritime), this versatile zoning allows for a broad range of uses including maritime industry operations such as fishing equipment sales and service, seafood processing, marine-related manufacturing, and boat storage. Additional permitted uses include retail, restaurant, affordable housing, and residential development, making this a uniquely flexible investment property. Parcel IDs include: 00362930, 00362940, 00362950, 00362960, and 00362970. The seller will provide a complete list of all personal property included in the sale, including major furniture, fixtures, and equipment. This is a rare opportunity to acquire a substantial, high-exposure commercial property with extensive waterfront and mixed-use potential in one of the most desirable areas of the Florida Keys.

38 Coco Plum Dr, Marathon

$4,950,000

Discover a luxurious oceanfront haven on Duck Key, Florida, listed at $5,250,000. This 4-bed, 4-bath, 3,417 sq ft home on a 10,070 sq ft lot in Plantation Island blends elegance with island charm. Built in 1965 and exquisitely updated in 2019 with brand new AC, Electric and Plumbing. It features shell stone-wrapped walls, iceberg marble floors on the first level, and onyx marble upstairs, with a book-matched slab in the master suite. The gourmet kitchen boasts a La Cornue gas stove, ideal for hurricane season. Enjoy 72 ft of deep-water dockage with 20,000 lb and 10,000 lb boat lifts, coral stone steps to a canal, and access to a private Duck Key boat ramp ($10 fee) and marina for safe storage and fueling. Fish for tuna, mahi-mahi, and snapper near deep ocean drops and humps, with easy bayside access via nearby bridges. Lush mango, guava, and plantain trees, plus bougainvillea, create a tropical oasis. Duck Key, 60 miles from Key West and 100 miles from Miami, offers 230 sunny days, 70s-90s temps, and no state income tax. Join the optional Duck Key clubhouse for a pool, tennis, pickleball, and events, or Hawks Cay Resort for its Michelin-rated Salt and Ash restaurant, saltwater lagoon, Dolphin Connection, and pools. Relax at Grassy Key Sandbar or dive into vibrant marine life with dolphins and manatees. With top schools and a tight-knit community, this home, steps from the island's entrance, features calacatta stone, Restoration Hardware furniture, and marble baseboards. Cash, conventional, or seller financing available.

4 Beds ⋅ 4 Baths ⋅ 618179 MLS

Discover a luxurious oceanfront haven on Duck Key, Florida, listed at $5,250,000. This 4-bed, 4-bath, 3,417 sq ft home on a 10,070 sq ft lot in Plantation Island blends elegance with island charm. Built in 1965 and exquisitely updated in 2019 with brand new AC, Electric and Plumbing. It features shell stone-wrapped walls, iceberg marble floors on the first level, and onyx marble upstairs, with a book-matched slab in the master suite. The gourmet kitchen boasts a La Cornue gas stove, ideal for hurricane season. Enjoy 72 ft of deep-water dockage with 20,000 lb and 10,000 lb boat lifts, coral stone steps to a canal, and access to a private Duck Key boat ramp ($10 fee) and marina for safe storage and fueling. Fish for tuna, mahi-mahi, and snapper near deep ocean drops and humps, with easy bayside access via nearby bridges. Lush mango, guava, and plantain trees, plus bougainvillea, create a tropical oasis. Duck Key, 60 miles from Key West and 100 miles from Miami, offers 230 sunny days, 70s-90s temps, and no state income tax. Join the optional Duck Key clubhouse for a pool, tennis, pickleball, and events, or Hawks Cay Resort for its Michelin-rated Salt and Ash restaurant, saltwater lagoon, Dolphin Connection, and pools. Relax at Grassy Key Sandbar or dive into vibrant marine life with dolphins and manatees. With top schools and a tight-knit community, this home, steps from the island's entrance, features calacatta stone, Restoration Hardware furniture, and marble baseboards. Cash, conventional, or seller financing available.

210 W Seaview Cir, Duck Key

$4,900,000

Experience modern waterfront living at its finest in this exceptional Key Largo residence where striking contemporary design meets the effortless luxury of the Florida Keys. Built in 2023 and spanning 4,787 square feet, this 3-story home offers 6 bedrooms, 5 baths and spectacular water views from nearly every room. Designed for both entertaining and an everyday escape, walls of glass fill the home with natural light while connecting the sophisticated interiors to expansive outdoor living spaces. The resort-style infinity pool features a sun shelf, submerged bar seating and massage jets, all overlooking the water. A rooftop deck and upper terrace capture ocean views, while a covered summer kitchen creates the perfect setting for sunset dinners and entertaining. Boaters will appreciate 70 feet of concrete dockage, a 20,000 pound boat lift and deep-water access that puts the Atlantic in your backyard. Inside, the chef's kitchen and oversized island anchor the open living space, complemented by a dramatic climate-controlled glass wine display. A private theater, versatile game room or gym, and elevator connecting all three levels add another layer of comfort and sophistication. From mornings on the water and endless shades of blue to evenings with breathtaking sunsets, 64 Andros Road offers the ultimate Keys lifestyle: modern, private, sophisticated and designed for those who want to live as beautifully as they play.

6 Beds ⋅ 5 Baths ⋅ 621334 MLS

Experience modern waterfront living at its finest in this exceptional Key Largo residence where striking contemporary design meets the effortless luxury of the Florida Keys. Built in 2023 and spanning 4,787 square feet, this 3-story home offers 6 bedrooms, 5 baths and spectacular water views from nearly every room. Designed for both entertaining and an everyday escape, walls of glass fill the home with natural light while connecting the sophisticated interiors to expansive outdoor living spaces. The resort-style infinity pool features a sun shelf, submerged bar seating and massage jets, all overlooking the water. A rooftop deck and upper terrace capture ocean views, while a covered summer kitchen creates the perfect setting for sunset dinners and entertaining. Boaters will appreciate 70 feet of concrete dockage, a 20,000 pound boat lift and deep-water access that puts the Atlantic in your backyard. Inside, the chef's kitchen and oversized island anchor the open living space, complemented by a dramatic climate-controlled glass wine display. A private theater, versatile game room or gym, and elevator connecting all three levels add another layer of comfort and sophistication. From mornings on the water and endless shades of blue to evenings with breathtaking sunsets, 64 Andros Road offers the ultimate Keys lifestyle: modern, private, sophisticated and designed for those who want to live as beautifully as they play.

64 S Andros Rd, Key Largo

$4,900,000

Once-in-a-Lifetime Opportunity: Own the Iconic Alabama Jacks in Key Largo! Step into the legacy of one of the most celebrated waterfront establishments in the USA. This legendary bar and restaurant, continually rated among the Best Bars & Restaurants in South Florida, Florida, and the nation, is ready for its next chapter. Located on Card Sound Road at the foot of the Card Sound Bridge, Alabama Jacks has been a beloved destination since the 1950s, renowned for its authentic charm, lively atmosphere, and world-famous conch fritters. Key Features: Rich History: Established in 1947 and operated by the current owner since 1981, this landmark has maintained its iconic status and rustic charm, drawing locals, tourists, and celebrities alike. Turnkey Package: Sale includes the business name, domain names, Facebook page, a thriving retail t-shirt business, proprietary recipes, and all furniture, fixtures, and equipment (FF&E). Prime Waterfront Property: Two parcels totaling 41,602 square feet (.95 acres) with over 360 linear feet of boat docks, direct boating access, and a private boat ramp (currently unused, offering potential for new revenue streams). Buildings & Infrastructure: Includes 2,297 sq. ft. of finished space, 4,729 sq. ft. of canopy space, and an apartment for onsite living or staff use. Also features a desalination system and a backup water truck with a tank. Long-Term Lease: New & Secure, 20-year lease with the U.S. Government renewed in 2021 through 2041. Unparalleled Legacy Alabama Jacks is a true piece of Americana, beloved by generations and celebrated in publications and TV appearances by icons like Emeril Lagasse, Conde Nast, and Kathie Lee Gifford. Whether you're continuing its proud traditions or exploring new opportunities, this business is primed for success. Opportunity to Franchise the name and brand. Don't miss this chance to own a slice of Florida Keys history and elevate an already thriving landmark to its next level.

1 Beds ⋅ 3 Baths ⋅ 613251 MLS

Once-in-a-Lifetime Opportunity: Own the Iconic Alabama Jacks in Key Largo! Step into the legacy of one of the most celebrated waterfront establishments in the USA. This legendary bar and restaurant, continually rated among the Best Bars & Restaurants in South Florida, Florida, and the nation, is ready for its next chapter. Located on Card Sound Road at the foot of the Card Sound Bridge, Alabama Jacks has been a beloved destination since the 1950s, renowned for its authentic charm, lively atmosphere, and world-famous conch fritters. Key Features: Rich History: Established in 1947 and operated by the current owner since 1981, this landmark has maintained its iconic status and rustic charm, drawing locals, tourists, and celebrities alike. Turnkey Package: Sale includes the business name, domain names, Facebook page, a thriving retail t-shirt business, proprietary recipes, and all furniture, fixtures, and equipment (FF&E). Prime Waterfront Property: Two parcels totaling 41,602 square feet (.95 acres) with over 360 linear feet of boat docks, direct boating access, and a private boat ramp (currently unused, offering potential for new revenue streams). Buildings & Infrastructure: Includes 2,297 sq. ft. of finished space, 4,729 sq. ft. of canopy space, and an apartment for onsite living or staff use. Also features a desalination system and a backup water truck with a tank. Long-Term Lease: New & Secure, 20-year lease with the U.S. Government renewed in 2021 through 2041. Unparalleled Legacy Alabama Jacks is a true piece of Americana, beloved by generations and celebrated in publications and TV appearances by icons like Emeril Lagasse, Conde Nast, and Kathie Lee Gifford. Whether you're continuing its proud traditions or exploring new opportunities, this business is primed for success. Opportunity to Franchise the name and brand. Don't miss this chance to own a slice of Florida Keys history and elevate an already thriving landmark to its next level.

58000 Card Sound Rd, Key Largo

$4,899,000

Experience turnkey luxury in the renowned Venetian Shores community with this exceptional 4-bedroom, 4-bath concrete waterfront residence, completely rebuilt from top to bottom with designer finishes and thoughtful details throughout. Offered fully furnished and completely outfitted, this home is truly ready to enjoy from day one. Everything is already in place, including linens, bathroom essentials, a fully stocked kitchen, and three mini-bar setups. Currently operating in a highly successful vacation rental program, the property has been thoughtfully designed and equipped for effortless personal use, entertaining, or continued rental operation. The beautifully finished interiors offer a sophisticated coastal feel, while an additional bonus space downstairs provides exceptional flexibility as a potential 5th bedroom, private office, game room, or lounge. Outdoor living is equally impressive. The resort-style pool is both heated and chilled for year-round enjoyment, while extensive landscape and architectural lighting creates an incredible atmosphere after sunset. Under-dock lighting illuminates the water below, perfect for nighttime fish watching and feeding. An outdoor shower provides the ideal place to rinse off after a swim or a long day on the water. Adding even more to the Keys lifestyle, the property includes a customized golf cart, making it easy to cruise through Venetian Shores and enjoy everything this highly sought-after neighborhood has to offer. From the complete rebuild and designer interiors to the turnkey furnishings, flexible living spaces, resort-style outdoor amenities, and established vacation rental operation, every detail of this home has been carefully considered. Simply arrive, unpack, and start enjoying the Florida Keys lifestyle.

4 Beds ⋅ 4 Baths ⋅ 621387 MLS

Experience turnkey luxury in the renowned Venetian Shores community with this exceptional 4-bedroom, 4-bath concrete waterfront residence, completely rebuilt from top to bottom with designer finishes and thoughtful details throughout. Offered fully furnished and completely outfitted, this home is truly ready to enjoy from day one. Everything is already in place, including linens, bathroom essentials, a fully stocked kitchen, and three mini-bar setups. Currently operating in a highly successful vacation rental program, the property has been thoughtfully designed and equipped for effortless personal use, entertaining, or continued rental operation. The beautifully finished interiors offer a sophisticated coastal feel, while an additional bonus space downstairs provides exceptional flexibility as a potential 5th bedroom, private office, game room, or lounge. Outdoor living is equally impressive. The resort-style pool is both heated and chilled for year-round enjoyment, while extensive landscape and architectural lighting creates an incredible atmosphere after sunset. Under-dock lighting illuminates the water below, perfect for nighttime fish watching and feeding. An outdoor shower provides the ideal place to rinse off after a swim or a long day on the water. Adding even more to the Keys lifestyle, the property includes a customized golf cart, making it easy to cruise through Venetian Shores and enjoy everything this highly sought-after neighborhood has to offer. From the complete rebuild and designer interiors to the turnkey furnishings, flexible living spaces, resort-style outdoor amenities, and established vacation rental operation, every detail of this home has been carefully considered. Simply arrive, unpack, and start enjoying the Florida Keys lifestyle.

115 Villa Bella Dr, Islamorada

$4,850,000

A RARE PRIVATE SANDY BEACH ESTATE IN ISLAMORADA! Discover a rare oceanfront paradise in the Florida Keys, situated on 1.35 acres of private oceanfront property featuring an extraordinary stretch of natural sandy beach, a feature seldom found in the Keys. Perfectly positioned next to iconic Sea Oats Beach, known for its pristine shoreline and seasonal sea turtle nesting, this exceptional estate offers privacy, coastal elegance, and breathtaking turquoise waters, just minutes from Islamorada's renowned dining and shopping. Enter through a private electric gate with ample parking for vehicles, boats, and trailers, plus an oversized three-car garage with pull-through access. An expansive ground-level storage area, currently utilized as a private gym, provides additional space for recreational equipment and boating gear. Built with concrete construction, the residence features impact-resistant windows and doors, along with a 25kW propane generator. Inside, marble floors, granite countertops, stainless steel appliances, a wine refrigerator, built-in ice maker, and spectacular open living spaces create an inviting coastal retreat. Four sets of double sliding impact glass doors frame panoramic ocean views and abundant natural light. The residence features five bedrooms and four full bathrooms, including two guest suites with private baths. The oceanview primary suite offers a walk-in closet, dual vanities, soaking tub, and walk-in shower. Outside, a lagoon-style pool, Jacuzzi, and wraparound balcony create an exceptional setting for entertaining and enjoying the ocean breezes. Offered below its 2026 appraised value, this remarkable oceanfront estate presents a rare opportunity to own 1.35 acres of private oceanfront property with a natural sandy beach, stunning open-water views, and convenient access to Islamorada's restaurants, shopping, and marinas.

5 Beds ⋅ 4 Baths ⋅ 621750 MLS

A RARE PRIVATE SANDY BEACH ESTATE IN ISLAMORADA! Discover a rare oceanfront paradise in the Florida Keys, situated on 1.35 acres of private oceanfront property featuring an extraordinary stretch of natural sandy beach, a feature seldom found in the Keys. Perfectly positioned next to iconic Sea Oats Beach, known for its pristine shoreline and seasonal sea turtle nesting, this exceptional estate offers privacy, coastal elegance, and breathtaking turquoise waters, just minutes from Islamorada's renowned dining and shopping. Enter through a private electric gate with ample parking for vehicles, boats, and trailers, plus an oversized three-car garage with pull-through access. An expansive ground-level storage area, currently utilized as a private gym, provides additional space for recreational equipment and boating gear. Built with concrete construction, the residence features impact-resistant windows and doors, along with a 25kW propane generator. Inside, marble floors, granite countertops, stainless steel appliances, a wine refrigerator, built-in ice maker, and spectacular open living spaces create an inviting coastal retreat. Four sets of double sliding impact glass doors frame panoramic ocean views and abundant natural light. The residence features five bedrooms and four full bathrooms, including two guest suites with private baths. The oceanview primary suite offers a walk-in closet, dual vanities, soaking tub, and walk-in shower. Outside, a lagoon-style pool, Jacuzzi, and wraparound balcony create an exceptional setting for entertaining and enjoying the ocean breezes. Offered below its 2026 appraised value, this remarkable oceanfront estate presents a rare opportunity to own 1.35 acres of private oceanfront property with a natural sandy beach, stunning open-water views, and convenient access to Islamorada's restaurants, shopping, and marinas.

74501 Overseas Hwy, Islamorada

$4,850,000

A rare find with beautiful Atlantic ocean view, luxury oceanfront estate where architecture, nature, and experience converge into something truly extraordinary. Bali style modern villa with large outdoor entertainment area, perfectly manicured garden in the best neighborhood of Key Largo. Surrounding houses are in $7-8 million range. Buy the best priced property in the high end neighborhood. Set on an expansive 21,300 sq ft parcel with 86 feet of direct Atlantic frontage, this private sanctuary captures uninterrupted, cinematic views of endless turquoise waters - sunrises here are not just seen, they are felt. The residence embodies refined coastal modern living, where clean architectural lines meet the organic beauty of its surroundings. Every space is curated to frame the ocean, creating a seamless indoor-outdoor flow that elevates everyday living into a resort-level experience. At the heart of the property lies a spectacular 75-foot infinity-edge heated or chilled pool, visually merging with the Atlantic beyond - an illusion of swimming into the horizon itself. Complementing this is a private beach enclave and boat ramp, offering direct access to the ocean and the rare privilege of stepping into your own stretch of the Atlantic. This is more than a home - it is a personal retreat, an entertainer's dream, and a strategic oceanfront asset in one of Key Largo's most sought-after locations. Whether envisioned as a primary residence, luxury retreat, or investment opportunity, this property offers a lifestyle defined by privacy, prestige, and possibility.

3 Beds ⋅ 3 Baths ⋅ 619743 MLS

A rare find with beautiful Atlantic ocean view, luxury oceanfront estate where architecture, nature, and experience converge into something truly extraordinary. Bali style modern villa with large outdoor entertainment area, perfectly manicured garden in the best neighborhood of Key Largo. Surrounding houses are in $7-8 million range. Buy the best priced property in the high end neighborhood. Set on an expansive 21,300 sq ft parcel with 86 feet of direct Atlantic frontage, this private sanctuary captures uninterrupted, cinematic views of endless turquoise waters - sunrises here are not just seen, they are felt. The residence embodies refined coastal modern living, where clean architectural lines meet the organic beauty of its surroundings. Every space is curated to frame the ocean, creating a seamless indoor-outdoor flow that elevates everyday living into a resort-level experience. At the heart of the property lies a spectacular 75-foot infinity-edge heated or chilled pool, visually merging with the Atlantic beyond - an illusion of swimming into the horizon itself. Complementing this is a private beach enclave and boat ramp, offering direct access to the ocean and the rare privilege of stepping into your own stretch of the Atlantic. This is more than a home - it is a personal retreat, an entertainer's dream, and a strategic oceanfront asset in one of Key Largo's most sought-after locations. Whether envisioned as a primary residence, luxury retreat, or investment opportunity, this property offers a lifestyle defined by privacy, prestige, and possibility.

60 Ocean Front Dr, Key Largo

$4,799,000

Set along 175 feet of direct Atlantic Ocean seawall, this completely remodeled 2026 Key Largo waterfront residence pairs contemporary coastal design with the boating lifestyle that defines the Florida Keys. Privately situated on a gated 14,220 SF corner lot at the end of a quiet cul-de-sac, the three-level home enjoys sweeping ocean views, easterly breezes, and an additional 100 feet of protected canal frontage. Boaters will appreciate a 26-by-14-foot cut-in boat slip with 5,000-pound davits, complemented by an additional 31 feet of concrete seawall. Cruise to nearby Rodriguez Key, explore the Atlantic's renowned fishing and diving grounds, or enjoy a short ride to Tavernier Creek for passage to Florida Bay and the Gulf side. Inside, a complete renovation introduces a refined coastal-modern aesthetic with warm neutrals, clean lines, and thoughtfully selected finishes. Expansive impact-rated windows and doors frame the waterfront setting, while the ocean-view kitchen features stainless steel appliances, a quartz center island, and adjoining dining area. Five bedrooms and three bathrooms offer comfortable accommodations for family and guests, with wraparound porches extending the living spaces outdoors. Framed by palms and tropical landscaping, the private pool and generous grounds invite a future summer kitchen, waterfront dining, and gathering spaces overlooking the Atlantic. A detached two-car garage, dedicated laundry, and main-level storage add everyday practicality, while a previously enclosed elevator shaft offers potential for future elevator installation. Conveniently accessible from Miami, this oceanfront residence offers an exceptional balance of privacy, refined coastal living, and direct access to the waters that make the Florida Keys one of the most sought-after boating destinations in South Florida.

5 Beds ⋅ 3 Baths ⋅ 621639 MLS

Set along 175 feet of direct Atlantic Ocean seawall, this completely remodeled 2026 Key Largo waterfront residence pairs contemporary coastal design with the boating lifestyle that defines the Florida Keys. Privately situated on a gated 14,220 SF corner lot at the end of a quiet cul-de-sac, the three-level home enjoys sweeping ocean views, easterly breezes, and an additional 100 feet of protected canal frontage. Boaters will appreciate a 26-by-14-foot cut-in boat slip with 5,000-pound davits, complemented by an additional 31 feet of concrete seawall. Cruise to nearby Rodriguez Key, explore the Atlantic's renowned fishing and diving grounds, or enjoy a short ride to Tavernier Creek for passage to Florida Bay and the Gulf side. Inside, a complete renovation introduces a refined coastal-modern aesthetic with warm neutrals, clean lines, and thoughtfully selected finishes. Expansive impact-rated windows and doors frame the waterfront setting, while the ocean-view kitchen features stainless steel appliances, a quartz center island, and adjoining dining area. Five bedrooms and three bathrooms offer comfortable accommodations for family and guests, with wraparound porches extending the living spaces outdoors. Framed by palms and tropical landscaping, the private pool and generous grounds invite a future summer kitchen, waterfront dining, and gathering spaces overlooking the Atlantic. A detached two-car garage, dedicated laundry, and main-level storage add everyday practicality, while a previously enclosed elevator shaft offers potential for future elevator installation. Conveniently accessible from Miami, this oceanfront residence offers an exceptional balance of privacy, refined coastal living, and direct access to the waters that make the Florida Keys one of the most sought-after boating destinations in South Florida.

1200 Mockingbird Rd, Key Largo

$4,750,000

Welcome to one of the most exclusive waterfront parcels in the Florida Keys. Located just steps from Coco Plum Beach and the Atlantic Ocean, this rare investment opportunity is the ultimate blend of luxury, lifestyle, and income potential. Professional Designed and built by D'Asign Source in 2019, this home is testament to timeless architecture, sophisticated interiors, and exceptional craftsmanship. Spanning 4,066 square feet and featuring 6 spacious bedrooms and 6.5 bathrooms with custom millwork and designer fixtures. The interiors are professionally furnished with a curated blend of comfort and elegance, complemented by expansive ceiling heights, open-concept living areas and balconies throughout. Designed with privacy in mind, this home includes its own private pool, tiki hut, and a dock offering deepwater and direct ocean access. Impact windows and doors provide storm security and peace of mind, while the three (3) air conditioning units to ensures optimal climate control on each level. Boating an abundance of storage on each level, an oversized laundry room, walk in pantry and en- suite accompanying each room. Whether you envision a serene primary residence or a luxury short-term rental business this property offers incredible versatility and value. Zoned for weekly rentals, the income potential is substantial, making this one of the most attractive investment opportunities in the Florida Keys. With seller financing available up to 50% of the purchase price, acquiring this rare trophy property is as strategic as it is luxurious. ALSO AVAILABLE TO PURCHASE AS A PORTFOLIO WITH THE TWO ADJACENT HOMES (See MLS #615102)

6 Beds ⋅ 7 Baths ⋅ 621947 MLS

Welcome to one of the most exclusive waterfront parcels in the Florida Keys. Located just steps from Coco Plum Beach and the Atlantic Ocean, this rare investment opportunity is the ultimate blend of luxury, lifestyle, and income potential. Professional Designed and built by D'Asign Source in 2019, this home is testament to timeless architecture, sophisticated interiors, and exceptional craftsmanship. Spanning 4,066 square feet and featuring 6 spacious bedrooms and 6.5 bathrooms with custom millwork and designer fixtures. The interiors are professionally furnished with a curated blend of comfort and elegance, complemented by expansive ceiling heights, open-concept living areas and balconies throughout. Designed with privacy in mind, this home includes its own private pool, tiki hut, and a dock offering deepwater and direct ocean access. Impact windows and doors provide storm security and peace of mind, while the three (3) air conditioning units to ensures optimal climate control on each level. Boating an abundance of storage on each level, an oversized laundry room, walk in pantry and en- suite accompanying each room. Whether you envision a serene primary residence or a luxury short-term rental business this property offers incredible versatility and value. Zoned for weekly rentals, the income potential is substantial, making this one of the most attractive investment opportunities in the Florida Keys. With seller financing available up to 50% of the purchase price, acquiring this rare trophy property is as strategic as it is luxurious. ALSO AVAILABLE TO PURCHASE AS A PORTFOLIO WITH THE TWO ADJACENT HOMES (See MLS #615102)

2394 Coco Plum Dr Unit 3, Marathon

$4,750,000

Welcome to one of the most exclusive waterfront parcels in the Florida Keys. Located just steps from Coco Plum Beach and the Atlantic Ocean, this rare investment opportunity is the ultimate blend of luxury, lifestyle, and income potential. Professional Designed and built by D'Asign Source in 2019, this home is testament to timeless architecture, sophisticated interiors, and exceptional craftsmanship. Spanning 4,066 square feet and featuring 6 spacious bedrooms and 6.5 bathrooms with custom millwork and designer fixtures. The interiors are professionally furnished with a curated blend of comfort and elegance, complemented by expansive ceiling heights, open-concept living areas and balconies throughout. Designed with privacy in mind, this home includes its own private pool, tiki hut, and a dock offering deepwater and direct ocean access. Impact windows and doors provide storm security and peace of mind, while the three (3) air conditioning units to ensures optimal climate control on each level. Boating an abundance of storage on each level, an oversized laundry room, walk in pantry and en- suite accompanying each room. Whether you envision a serene primary residence or a luxury short-term rental business this property offers incredible versatility and value. Zoned for weekly rentals, the income potential is substantial, making this one of the most attractive investment opportunities in the Florida Keys. With seller financing available up to 50% of the purchase price, acquiring this rare trophy property is as strategic as it is luxurious. ALSO AVAILABLE TO PURCHASE AS A PORTFOLIO WITH THE TWO ADJACENT HOMES

6 Beds ⋅ 7 Baths ⋅ 621945 MLS

Welcome to one of the most exclusive waterfront parcels in the Florida Keys. Located just steps from Coco Plum Beach and the Atlantic Ocean, this rare investment opportunity is the ultimate blend of luxury, lifestyle, and income potential. Professional Designed and built by D'Asign Source in 2019, this home is testament to timeless architecture, sophisticated interiors, and exceptional craftsmanship. Spanning 4,066 square feet and featuring 6 spacious bedrooms and 6.5 bathrooms with custom millwork and designer fixtures. The interiors are professionally furnished with a curated blend of comfort and elegance, complemented by expansive ceiling heights, open-concept living areas and balconies throughout. Designed with privacy in mind, this home includes its own private pool, tiki hut, and a dock offering deepwater and direct ocean access. Impact windows and doors provide storm security and peace of mind, while the three (3) air conditioning units to ensures optimal climate control on each level. Boating an abundance of storage on each level, an oversized laundry room, walk in pantry and en- suite accompanying each room. Whether you envision a serene primary residence or a luxury short-term rental business this property offers incredible versatility and value. Zoned for weekly rentals, the income potential is substantial, making this one of the most attractive investment opportunities in the Florida Keys. With seller financing available up to 50% of the purchase price, acquiring this rare trophy property is as strategic as it is luxurious. ALSO AVAILABLE TO PURCHASE AS A PORTFOLIO WITH THE TWO ADJACENT HOMES

2394 Coco Plum Dr Unit 1, Marathon

$4,750,000

Discover effortless waterfront living in the exclusive gated community of Shark Key. Beautifully designed and newly constructed, this stunning residence is offered fully furnished and turnkey, allowing you to move right in and begin enjoying the best of the Florida Keys. Combining coastal sophistication with relaxed island living, the home offers breathtaking open-water views, spectacular sunsets, and an exceptional indoor-outdoor living experience. Designed to embrace its waterfront setting, the residence features an inviting, open layout filled with natural light, beautiful water views, and a seamless connection to the outdoors. Expansive covered balconies and terraces extend the living space, providing wonderful areas for relaxing, dining, and entertaining while enjoying the surrounding tropical beauty and gentle island breezes. The private pool and outdoor living areas create a beautiful setting for spending time with family and friends or simply unwinding as the sun sets over the open water. Additional features include an elevator, enclosed storage, and abundant covered parking beneath the home. The generous ground-level area offers flexibility and possibilities for a variety of uses, adding to the property's convenience and appeal. Approved permits for an observation dock provide the opportunity to further enjoy the property's spectacular waterfront setting and sunset views. Located just minutes from Key West, Shark Key is one of the Florida Keys' most prestigious gated communities, offering residents an array of resort-style amenities, including tennis and pickleball courts, a swimming lagoon, and a private beach area. New construction, fully furnished, and completely turnkey, this is an opportunity to enjoy the beauty of the Florida Keys without the wait. Simply move in, settle in, and enjoy.

3 Beds ⋅ 3 Baths ⋅ 621785 MLS

Discover effortless waterfront living in the exclusive gated community of Shark Key. Beautifully designed and newly constructed, this stunning residence is offered fully furnished and turnkey, allowing you to move right in and begin enjoying the best of the Florida Keys. Combining coastal sophistication with relaxed island living, the home offers breathtaking open-water views, spectacular sunsets, and an exceptional indoor-outdoor living experience. Designed to embrace its waterfront setting, the residence features an inviting, open layout filled with natural light, beautiful water views, and a seamless connection to the outdoors. Expansive covered balconies and terraces extend the living space, providing wonderful areas for relaxing, dining, and entertaining while enjoying the surrounding tropical beauty and gentle island breezes. The private pool and outdoor living areas create a beautiful setting for spending time with family and friends or simply unwinding as the sun sets over the open water. Additional features include an elevator, enclosed storage, and abundant covered parking beneath the home. The generous ground-level area offers flexibility and possibilities for a variety of uses, adding to the property's convenience and appeal. Approved permits for an observation dock provide the opportunity to further enjoy the property's spectacular waterfront setting and sunset views. Located just minutes from Key West, Shark Key is one of the Florida Keys' most prestigious gated communities, offering residents an array of resort-style amenities, including tennis and pickleball courts, a swimming lagoon, and a private beach area. New construction, fully furnished, and completely turnkey, this is an opportunity to enjoy the beauty of the Florida Keys without the wait. Simply move in, settle in, and enjoy.

58 Cannon Royal Dr, Shark Key

$4,750,000

Villa 1 offers one of the most coveted locations within the exclusive 22-villa community at The Islands of Islamorada. Ideally positioned as the closest oceanfront villa to the private marina, this exceptional residence enjoys some of the community's most impressive ocean views and an incredible connection to the water. The Villas at the Islands of Islamorada is a meticulously designed, private gated community now offering fee-simple waterfront single family residences. Every comfort considered and exuding coastal living with stunning ocean views. Four bedrooms, four and one-half bathrooms three-floor villa offers 2,574 sq ft of interior plus 1,169 sq ft patios. Contemporary island architecture with an open, airy, and light-filled design. Residences are being offered fully furnished and amenities include open-concept kitchen, dining, and living spaces, powder room, ample closets, two oceanfront balconies, laundry room, 8 ft interior doors, and a 2-car garage with electric charging and added storage. The Beach Club delivers a luxurious experience with its pristine 600ft beach, private boat basin with ample dockage, two oceanfront pools, an oceanfront bar, fitness center, playgrounds for the kids, pickleball courts, unique driving range that extends into the ocean, plus a plethora of water activities allowing guests to fully immerse themselves in the Keys lifestyle. The privacy and exclusivity of this community set itself apart as a gated secluded beach destination environment surrounded by lush, mature landscaping that allows for effortless multigenerational vacations complete with and attentive staff. Open model unit available to show anytime. Some interior photos are from comparable villas within the property and not exact villa listed.

4 Beds ⋅ 5 Baths ⋅ 620933 MLS

Villa 1 offers one of the most coveted locations within the exclusive 22-villa community at The Islands of Islamorada. Ideally positioned as the closest oceanfront villa to the private marina, this exceptional residence enjoys some of the community's most impressive ocean views and an incredible connection to the water. The Villas at the Islands of Islamorada is a meticulously designed, private gated community now offering fee-simple waterfront single family residences. Every comfort considered and exuding coastal living with stunning ocean views. Four bedrooms, four and one-half bathrooms three-floor villa offers 2,574 sq ft of interior plus 1,169 sq ft patios. Contemporary island architecture with an open, airy, and light-filled design. Residences are being offered fully furnished and amenities include open-concept kitchen, dining, and living spaces, powder room, ample closets, two oceanfront balconies, laundry room, 8 ft interior doors, and a 2-car garage with electric charging and added storage. The Beach Club delivers a luxurious experience with its pristine 600ft beach, private boat basin with ample dockage, two oceanfront pools, an oceanfront bar, fitness center, playgrounds for the kids, pickleball courts, unique driving range that extends into the ocean, plus a plethora of water activities allowing guests to fully immerse themselves in the Keys lifestyle. The privacy and exclusivity of this community set itself apart as a gated secluded beach destination environment surrounded by lush, mature landscaping that allows for effortless multigenerational vacations complete with and attentive staff. Open model unit available to show anytime. Some interior photos are from comparable villas within the property and not exact villa listed.

82779 Old Hwy Unit 1, Islamorada

$4,750,000

TRANSIENT LICENSE TRANSFER RECEIVER ZONE!!!! A rare opportunity to own one of Key West's most captivating waterfront properties, where history, character, and endless potential come together. Nestled along the historic Trumbo Point waterfront, this remarkable estate has remained in the same family for generations and reflects a rich connection to one of the island's most significant maritime neighborhoods. Thought to have origins dating back to the early 20th century, the property showcases timeless Old Key West charm while offering the space and flexibility rarely found today. The main residence is complemented by a separate guest cottage on an oversized waterfront parcel, creating endless possibilities for multigenerational living, a private family compound, or an exceptional investment opportunity. Located in an area once shaped by the island's cigar industry, railroad expansion, and later the development of the Naval Air Station and Coast Guard facilities, this home sits within a neighborhood that tells the story of Key West's evolution through more than a century of history. From the moment you arrive, you'll appreciate the mature tropical landscape, water access, and the feeling of stepping into a piece of Old Key West. Whether you choose to preserve its historic character, thoughtfully enhance the existing structures, or create your own legacy estate, opportunities like this are exceptionally rare. Waterfront properties with this combination of history, location, size, and family ownership seldom become available. 901 Eisenhower Drive is more than a home--it's an opportunity to own a meaningful piece of Key West's past while creating its next chapter.

6 Beds ⋅ 5 Baths ⋅ 620662 MLS

TRANSIENT LICENSE TRANSFER RECEIVER ZONE!!!! A rare opportunity to own one of Key West's most captivating waterfront properties, where history, character, and endless potential come together. Nestled along the historic Trumbo Point waterfront, this remarkable estate has remained in the same family for generations and reflects a rich connection to one of the island's most significant maritime neighborhoods. Thought to have origins dating back to the early 20th century, the property showcases timeless Old Key West charm while offering the space and flexibility rarely found today. The main residence is complemented by a separate guest cottage on an oversized waterfront parcel, creating endless possibilities for multigenerational living, a private family compound, or an exceptional investment opportunity. Located in an area once shaped by the island's cigar industry, railroad expansion, and later the development of the Naval Air Station and Coast Guard facilities, this home sits within a neighborhood that tells the story of Key West's evolution through more than a century of history. From the moment you arrive, you'll appreciate the mature tropical landscape, water access, and the feeling of stepping into a piece of Old Key West. Whether you choose to preserve its historic character, thoughtfully enhance the existing structures, or create your own legacy estate, opportunities like this are exceptionally rare. Waterfront properties with this combination of history, location, size, and family ownership seldom become available. 901 Eisenhower Drive is more than a home--it's an opportunity to own a meaningful piece of Key West's past while creating its next chapter.

901 Eisenhower Dr, Key West

$4,750,000

TRANSIENT LICENSE TRANSFER RECEIVER ZONE!!!! A rare opportunity to own one of Key West's most captivating waterfront properties, where history, character, and endless potential come together. Nestled along the historic Trumbo Point waterfront, this remarkable estate has remained in the same family for generations and reflects a rich connection to one of the island's most significant maritime neighborhoods. Thought to have origins dating back to the early 20th century, the property showcases timeless Old Key West charm while offering the space and flexibility rarely found today. The main residence is complemented by a separate guest cottage on an oversized waterfront parcel, creating endless possibilities for multigenerational living, a private family compound, or an exceptional investment opportunity. Located in an area once shaped by the island's cigar industry, railroad expansion, and later the development of the Naval Air Station and Coast Guard facilities, this home sits within a neighborhood that tells the story of Key West's evolution through more than a century of history. From the moment you arrive, you'll appreciate the mature tropical landscape, water access, and the feeling of stepping into a piece of Old Key West. Whether you choose to preserve its historic character, thoughtfully enhance the existing structures, or create your own legacy estate, opportunities like this are exceptionally rare. Waterfront properties with this combination of history, location, size, and family ownership seldom become available. 901 Eisenhower Drive is more than a home--it's an opportunity to own a meaningful piece of Key West's past while creating its next chapter.

7 Beds ⋅ 5 Baths ⋅ 620661 MLS

TRANSIENT LICENSE TRANSFER RECEIVER ZONE!!!! A rare opportunity to own one of Key West's most captivating waterfront properties, where history, character, and endless potential come together. Nestled along the historic Trumbo Point waterfront, this remarkable estate has remained in the same family for generations and reflects a rich connection to one of the island's most significant maritime neighborhoods. Thought to have origins dating back to the early 20th century, the property showcases timeless Old Key West charm while offering the space and flexibility rarely found today. The main residence is complemented by a separate guest cottage on an oversized waterfront parcel, creating endless possibilities for multigenerational living, a private family compound, or an exceptional investment opportunity. Located in an area once shaped by the island's cigar industry, railroad expansion, and later the development of the Naval Air Station and Coast Guard facilities, this home sits within a neighborhood that tells the story of Key West's evolution through more than a century of history. From the moment you arrive, you'll appreciate the mature tropical landscape, water access, and the feeling of stepping into a piece of Old Key West. Whether you choose to preserve its historic character, thoughtfully enhance the existing structures, or create your own legacy estate, opportunities like this are exceptionally rare. Waterfront properties with this combination of history, location, size, and family ownership seldom become available. 901 Eisenhower Drive is more than a home--it's an opportunity to own a meaningful piece of Key West's past while creating its next chapter.

901 Eisenhower Dr, Key West

$4,750,000

Double Lot! Unparalleled Waterfront Command in Port Antigua. Boasting one of the largest water frontages in Islamorada's exclusive Port Antigua, this striking 3 story residence offers 4 bedrooms, 4.5 baths, and an extraordinary 220 feet of dockage with dual boat lifts. Every bedroom is beautifully appointed across thoughtfully designed living levels. Step outside to your private marina, where turnkey boating infrastructure meets the crystalline waters of the Florida Keys. Port Antigua residents enjoy exclusive access to a private beach and boat ramp amenities known only to a select few. Where unmatched dockage and island luxury converge in one of Islamorada's most coveted addresses.

4 Beds ⋅ 5 Baths ⋅ 619714 MLS

Double Lot! Unparalleled Waterfront Command in Port Antigua. Boasting one of the largest water frontages in Islamorada's exclusive Port Antigua, this striking 3 story residence offers 4 bedrooms, 4.5 baths, and an extraordinary 220 feet of dockage with dual boat lifts. Every bedroom is beautifully appointed across thoughtfully designed living levels. Step outside to your private marina, where turnkey boating infrastructure meets the crystalline waters of the Florida Keys. Port Antigua residents enjoy exclusive access to a private beach and boat ramp amenities known only to a select few. Where unmatched dockage and island luxury converge in one of Islamorada's most coveted addresses.

44 W Plaza Del Lago, Islamorada

$4,700,000

A Key West original. 1014 Flagler Avenue is a storied Casa Marina residence shaped by legendary Key West developer David Wolkowsky and set behind privacy walls on an exceptional 11,730-square-foot corner double lot. Some homes are built. Others are authored. At its center: 40 feet of pool, surrounded by mature tropical landscaping and hardscape by Craig Reynolds Landscape Architecture, creating the feel of a private compound hidden in plain sight. Inside, the scale shifts again with 22-foot ceilings, walls of glass, 10-foot doors and sliders, custom teak, and a dramatic floor-to-ceiling library. The main residence offers two bedrooms and two-and-a-half baths, anchored by a chef's kitchen and expansive indoor-outdoor living. Extensive updates include new systems and impact-rated windows and doors. A completely separate one-bedroom guest house adds its own kitchen, laundry and private garden. 3 bedrooms. 3.5 baths. 3,104 square feet. 11,730 square feet of land. 40 feet of pool. In a market full of beautiful houses, 1014 Flagler offers something harder to replicate: a point of view.

3 Beds ⋅ 4 Baths ⋅ 618577 MLS

A Key West original. 1014 Flagler Avenue is a storied Casa Marina residence shaped by legendary Key West developer David Wolkowsky and set behind privacy walls on an exceptional 11,730-square-foot corner double lot. Some homes are built. Others are authored. At its center: 40 feet of pool, surrounded by mature tropical landscaping and hardscape by Craig Reynolds Landscape Architecture, creating the feel of a private compound hidden in plain sight. Inside, the scale shifts again with 22-foot ceilings, walls of glass, 10-foot doors and sliders, custom teak, and a dramatic floor-to-ceiling library. The main residence offers two bedrooms and two-and-a-half baths, anchored by a chef's kitchen and expansive indoor-outdoor living. Extensive updates include new systems and impact-rated windows and doors. A completely separate one-bedroom guest house adds its own kitchen, laundry and private garden. 3 bedrooms. 3.5 baths. 3,104 square feet. 11,730 square feet of land. 40 feet of pool. In a market full of beautiful houses, 1014 Flagler offers something harder to replicate: a point of view.

1014 Flagler Ave, Key West

$4,700,000

Introducing Seven Palms Cove, a one-of-a-kind new construction community redefining luxury island living in the Florida Keys. With only seven exclusive oceanfront residences starting at $4M, this private, gated enclave offers an extraordinary opportunity to own a slice of paradise just minutes from Key West. Each home spans over 4,000 sq. ft. with 5 bedrooms, 5.5 bathrooms, and open-concept layouts with 10' ceilings, impact glass, and abundant natural light. The chef's kitchen includes premium appliances, quartz countertops, pantry, and large island ideal for entertaining. Multiple verandas, balconies, and a rooftop observation deck deliver 360-degree sunrise and sunset views. Outdoors, enjoy your own sparkling infinity pool, expansive pool deck, and seamless flow to the water. Every residence conveys with an assigned dock space in a private boat basin featuring new composite docks with electric, water, and a fillet station—perfect for boating enthusiasts. Homes are equipped with Tesla Solar, an elevator, and generous storage. Resort-style amenities include a sport court for tennis, pickleball, and basketball, along with oceanfront lounge areas, hammocks, and opportunities for paddleboarding and kayaking. Just one block from a private airport, accessibility is unmatched. For investors, Seven Palms Cove is an exceptional opportunity: there are no rental restrictions, and nearby comparable properties generate over $300,000 annually. Whether as a forever home, luxury vacation retreat, or high-performing investment, Seven Palms Cove offers the perfect blend of exclusivity, comfort, and opportunity in the Florida Keys.

5 Beds ⋅ 6 Baths ⋅ 616705 MLS

Introducing Seven Palms Cove, a one-of-a-kind new construction community redefining luxury island living in the Florida Keys. With only seven exclusive oceanfront residences starting at $4M, this private, gated enclave offers an extraordinary opportunity to own a slice of paradise just minutes from Key West. Each home spans over 4,000 sq. ft. with 5 bedrooms, 5.5 bathrooms, and open-concept layouts with 10' ceilings, impact glass, and abundant natural light. The chef's kitchen includes premium appliances, quartz countertops, pantry, and large island ideal for entertaining. Multiple verandas, balconies, and a rooftop observation deck deliver 360-degree sunrise and sunset views. Outdoors, enjoy your own sparkling infinity pool, expansive pool deck, and seamless flow to the water. Every residence conveys with an assigned dock space in a private boat basin featuring new composite docks with electric, water, and a fillet station—perfect for boating enthusiasts. Homes are equipped with Tesla Solar, an elevator, and generous storage. Resort-style amenities include a sport court for tennis, pickleball, and basketball, along with oceanfront lounge areas, hammocks, and opportunities for paddleboarding and kayaking. Just one block from a private airport, accessibility is unmatched. For investors, Seven Palms Cove is an exceptional opportunity: there are no rental restrictions, and nearby comparable properties generate over $300,000 annually. Whether as a forever home, luxury vacation retreat, or high-performing investment, Seven Palms Cove offers the perfect blend of exclusivity, comfort, and opportunity in the Florida Keys.

231 E Shore Dr Unit 6, Summerland

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