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Experience the best of the Florida Keys in this exceptional pool home, ideally situated in Venetian Shores--one of Islamorada's most coveted waterfront communities. Offering 70 feet of protected dockage, this property is a premier boating opportunity with quick access to the bay and ocean via Snake Creek Bridge. Designed to accommodate family and guests with ease, the oversized home features five spacious bedrooms, four-and-a-half baths, a garage, and an upstairs flex space with a private balcony overlooking the pool and wide canal. Timeless finishes include a charming foyer, rich hardwood flooring throughout, a dedicated office, game room complete with a custom built-in bar, and abundant natural light that enhances every level of the home. Built for both comfort and peace of mind, the residence is equipped with impact-rated doors and windows, a whole-home generator, and a propane tank, providing year-round reliability and resilience. Whether you're entertaining poolside, hosting extended family, or setting out for a day on the water, this exceptional waterfront residence embodies the relaxed luxury and boating lifestyle that define Islamorada.

5 Beds ⋅ 6 Baths ⋅ 620757 MLS

Experience the best of the Florida Keys in this exceptional pool home, ideally situated in Venetian Shores--one of Islamorada's most coveted waterfront communities. Offering 70 feet of protected dockage, this property is a premier boating opportunity with quick access to the bay and ocean via Snake Creek Bridge. Designed to accommodate family and guests with ease, the oversized home features five spacious bedrooms, four-and-a-half baths, a garage, and an upstairs flex space with a private balcony overlooking the pool and wide canal. Timeless finishes include a charming foyer, rich hardwood flooring throughout, a dedicated office, game room complete with a custom built-in bar, and abundant natural light that enhances every level of the home. Built for both comfort and peace of mind, the residence is equipped with impact-rated doors and windows, a whole-home generator, and a propane tank, providing year-round reliability and resilience. Whether you're entertaining poolside, hosting extended family, or setting out for a day on the water, this exceptional waterfront residence embodies the relaxed luxury and boating lifestyle that define Islamorada.

109 Valencia Dr, Islamorada

Escape to ''The Castle'', a luxurious gated Gulf-front estate rarely spanning 1.14 acres on Big Pine Key. This extraordinary retreat is a graceful blend of architectural grandeur and coastal charm, thoughtfully designed for both relaxation and recreation. Boaters will delight in an unparalleled offering of 235 feet of dockage total: 140 feet of protected canal-front dockage featuring a 15,000 lb lift, cut-in slip, boat ramp, plus a 95-foot open water pier-style dock with additional 15,000 lb lift and cut-in slip, set against a 130-foot concrete seawall for secure, convenient access. Crafted in 2014 with solid poured concrete, impact-rated windows and doors, whole home generator and elevator, the home is built for enduring elegance. With over 4,600 square feet of refined interior space, this 3-bedroom, 3-bathroom estate is an architect's masterpiece with its stately presence, curved openings, and striking double staircase. Step inside to a breathtaking panorama of endless open Gulf waters and nightly sunset performances. The chef's kitchen is a dream for entertaining, featuring 10.5-foot island with seating for 8, dual sinks, refrigerators, and ovens, plus Jenn-Air 6-burner gas cooktop with pot filler, and rich wood cabinetry. Enjoy the grand family room with Gulf views, host movie nights in the private theater, or dine al-fresco under the stars. Nearby, find the full-size laundry room and storage. The top-floor primary suite is a sanctuary, offering sweeping water views, home office, private lounge with kitchenette, spa-like bath with clawfoot tub, tiled shower and generous walk-in closet with additional laundry. Outside, the resort-style pool beckons with a spa, water features, LED lighting, plus heater and chiller. Rooftop deck with 180-degree views, and unrivaled sunsets await. Offered fully furnished, this is ultimate Keys living without compromise!

3 Beds ⋅ 3 Baths ⋅ 619696 MLS

Escape to ''The Castle'', a luxurious gated Gulf-front estate rarely spanning 1.14 acres on Big Pine Key. This extraordinary retreat is a graceful blend of architectural grandeur and coastal charm, thoughtfully designed for both relaxation and recreation. Boaters will delight in an unparalleled offering of 235 feet of dockage total: 140 feet of protected canal-front dockage featuring a 15,000 lb lift, cut-in slip, boat ramp, plus a 95-foot open water pier-style dock with additional 15,000 lb lift and cut-in slip, set against a 130-foot concrete seawall for secure, convenient access. Crafted in 2014 with solid poured concrete, impact-rated windows and doors, whole home generator and elevator, the home is built for enduring elegance. With over 4,600 square feet of refined interior space, this 3-bedroom, 3-bathroom estate is an architect's masterpiece with its stately presence, curved openings, and striking double staircase. Step inside to a breathtaking panorama of endless open Gulf waters and nightly sunset performances. The chef's kitchen is a dream for entertaining, featuring 10.5-foot island with seating for 8, dual sinks, refrigerators, and ovens, plus Jenn-Air 6-burner gas cooktop with pot filler, and rich wood cabinetry. Enjoy the grand family room with Gulf views, host movie nights in the private theater, or dine al-fresco under the stars. Nearby, find the full-size laundry room and storage. The top-floor primary suite is a sanctuary, offering sweeping water views, home office, private lounge with kitchenette, spa-like bath with clawfoot tub, tiled shower and generous walk-in closet with additional laundry. Outside, the resort-style pool beckons with a spa, water features, LED lighting, plus heater and chiller. Rooftop deck with 180-degree views, and unrivaled sunsets await. Offered fully furnished, this is ultimate Keys living without compromise!

3742 Seagrape St, Big Pine

A LEGACY KEYS BAYFRONT PROPERTY OFFERING ENJOYMENT TODAY AND ENDLESS POSSIBILITIES FOR TOMORROW! Preserve and enhance the charm of a Florida Keys homestead, or reimagine the property to fit your future vision, with immediate use short-term and strong long-term investment potential. The rare double lot spans nearly one acre on a prime point of land along Florida Bay. With over 200 feet of improved shoreline, this property nearly doubles the width of typical waterfront parcels. Tucked away among native hardwoods at the Southern edge of Key Largo and the Village of Islamorada, this parcel offers exceptional privacy with both sunrise and sunset views. Features include a sandy beach, a cut-in boat basin with deep-water channel access, 2 ramps for launching pleasure watercraft, a resort-style pool, a concrete pier, aquarium-like waters with crystal-clear blue tones, and a sandy bay bottom teeming with marine life. The existing 4BD/2BA concrete residence provides instant enjoyment and valuable building rights, allowing you to create a custom waterfront retreat without waiting for a Monroe County ROGO allocation. A rare opportunity for a family compound or legacy estate in one of the Upper Keys' most unique bayfront settings.

4 Beds ⋅ 2 Baths ⋅ 616004 MLS

A LEGACY KEYS BAYFRONT PROPERTY OFFERING ENJOYMENT TODAY AND ENDLESS POSSIBILITIES FOR TOMORROW! Preserve and enhance the charm of a Florida Keys homestead, or reimagine the property to fit your future vision, with immediate use short-term and strong long-term investment potential. The rare double lot spans nearly one acre on a prime point of land along Florida Bay. With over 200 feet of improved shoreline, this property nearly doubles the width of typical waterfront parcels. Tucked away among native hardwoods at the Southern edge of Key Largo and the Village of Islamorada, this parcel offers exceptional privacy with both sunrise and sunset views. Features include a sandy beach, a cut-in boat basin with deep-water channel access, 2 ramps for launching pleasure watercraft, a resort-style pool, a concrete pier, aquarium-like waters with crystal-clear blue tones, and a sandy bay bottom teeming with marine life. The existing 4BD/2BA concrete residence provides instant enjoyment and valuable building rights, allowing you to create a custom waterfront retreat without waiting for a Monroe County ROGO allocation. A rare opportunity for a family compound or legacy estate in one of the Upper Keys' most unique bayfront settings.

36 Sunset Rd, Key Largo

WHERE SUNRISE MEETS SUNSET- CREATE YOUR WATERFRONT MASTERPIECE IN THE FLORIDA KEYS! Remarkable and rare bayfront building opportunity in South Key Largo awaits on this unique property that spans nearly an acre of upland across two contiguous lots offering 200 feet of prime waterfront with a highly coveted building right already in place. Design and build your dream estate to your exact specifications, with the unparalleled bonus of both sunrise and sunset views from its exclusive point of land. Boating enthusiasts will appreciate a quarter acre of sandy baybottom below two docking areas, a concrete seawall, a protected boat basin, and ample space for your waterfront escapades. Enjoy the natural beauty of a sandy beach framed by sea oats, swaying palm trees, and mature native foliage, all tucked away behind a quiet, family-oriented neighborhood far from the highway's hustle and bustle. Whether you're seeking serenity, privacy, or a blank canvas to create your ultimate island retreat, this property is truly one of a kind. Don't miss this extraordinary opportunity to create your literal peace of paradise in the Florida Keys! Bonus: There is an existing single family home/bungalow & pool on-site that can be utilized as your primary building right or kept as a guest house for your larger estate...the choice is yours! Duplicate Listing, see MLS #616004

613012 MLS

WHERE SUNRISE MEETS SUNSET- CREATE YOUR WATERFRONT MASTERPIECE IN THE FLORIDA KEYS! Remarkable and rare bayfront building opportunity in South Key Largo awaits on this unique property that spans nearly an acre of upland across two contiguous lots offering 200 feet of prime waterfront with a highly coveted building right already in place. Design and build your dream estate to your exact specifications, with the unparalleled bonus of both sunrise and sunset views from its exclusive point of land. Boating enthusiasts will appreciate a quarter acre of sandy baybottom below two docking areas, a concrete seawall, a protected boat basin, and ample space for your waterfront escapades. Enjoy the natural beauty of a sandy beach framed by sea oats, swaying palm trees, and mature native foliage, all tucked away behind a quiet, family-oriented neighborhood far from the highway's hustle and bustle. Whether you're seeking serenity, privacy, or a blank canvas to create your ultimate island retreat, this property is truly one of a kind. Don't miss this extraordinary opportunity to create your literal peace of paradise in the Florida Keys! Bonus: There is an existing single family home/bungalow & pool on-site that can be utilized as your primary building right or kept as a guest house for your larger estate...the choice is yours! Duplicate Listing, see MLS #616004

36 Sunset Rd, Key Largo

$4,645,000

Experience breathtaking sunsets throughout the year on this waterfront lot ready for construction in Islamorada. There's no enduring lengthy waiting periods for development - this parcel comes with an active permit and holds a Residential Estate zoning designation. Encompassing a generous expanse from the highway to the bay, the property boasts an impressive 1.2 acres of land plus another .24 acres of bay bottom, accommodating deep-water dockage and a picturesque sandy beach. Seize the opportunity to actualize your ideal residence right now!

618904 MLS

Experience breathtaking sunsets throughout the year on this waterfront lot ready for construction in Islamorada. There's no enduring lengthy waiting periods for development - this parcel comes with an active permit and holds a Residential Estate zoning designation. Encompassing a generous expanse from the highway to the bay, the property boasts an impressive 1.2 acres of land plus another .24 acres of bay bottom, accommodating deep-water dockage and a picturesque sandy beach. Seize the opportunity to actualize your ideal residence right now!

75750 Overseas Hwy, Islamorada

$4,600,000

Located in sought-after Venetian Shores subdivision in Islamorada, this canal-front home was renovated in 2022. Sought after location - just one lot in from Snake Creek, offering exceptional boating access, 100' of deep water dockage with a 20k boat lift. With approximately 4,600sf of living space, 5 bedrooms and 5.5 bathrooms, the home is situated above base flood elevation and offers an impressive amount of space for the Florida Keys lifestyle. The east-facing orientation captures the morning sun and prevailing breezes while providing welcome afternoon shade. The main residence features 4 bedrooms and 4.5 bathrooms, an open living area with soaring ceilings, a spacious kitchen, pool table area, and a private office with incredible views stretching from the ocean to the bay. An expansive screened waterfront porch serves as an extension of the living area, offering a comfortable setting to relax, entertain, and enjoy the canal views and prevailing breezes. The lower level offers a separate 1 bedroom, 1 bath guest space with views of the pool and its own screened porch. With nearly 1,200sf of covered porches, the home was designed to fully embrace indoor-outdoor Keys living. A new pool was added in 2023, offering privacy and complemented by tropical landscaping, outdoor lighting, artificial turf, and white fencing. Situated on a 9,500sf lot, the property also offers an impressive 1,188sf four-car garage plus an additional dedicated storage room - an exceptional amount of storage rarely found in a Keys home. Additional features include impact windows and doors throughout, metal roof, a paver driveway, and a cul-de-sac location. With expansive living and outdoor spaces, panoramic water views, 100' of deep water dockage, and Snake Creek just seconds away for convenient ocean-to-bay access, this Venetian Shores home offers a rare combination of space, storage, location, and boating convenience in the heart of Islamorada.

5 Beds ⋅ 6 Baths ⋅ 620549 MLS

Located in sought-after Venetian Shores subdivision in Islamorada, this canal-front home was renovated in 2022. Sought after location - just one lot in from Snake Creek, offering exceptional boating access, 100' of deep water dockage with a 20k boat lift. With approximately 4,600sf of living space, 5 bedrooms and 5.5 bathrooms, the home is situated above base flood elevation and offers an impressive amount of space for the Florida Keys lifestyle. The east-facing orientation captures the morning sun and prevailing breezes while providing welcome afternoon shade. The main residence features 4 bedrooms and 4.5 bathrooms, an open living area with soaring ceilings, a spacious kitchen, pool table area, and a private office with incredible views stretching from the ocean to the bay. An expansive screened waterfront porch serves as an extension of the living area, offering a comfortable setting to relax, entertain, and enjoy the canal views and prevailing breezes. The lower level offers a separate 1 bedroom, 1 bath guest space with views of the pool and its own screened porch. With nearly 1,200sf of covered porches, the home was designed to fully embrace indoor-outdoor Keys living. A new pool was added in 2023, offering privacy and complemented by tropical landscaping, outdoor lighting, artificial turf, and white fencing. Situated on a 9,500sf lot, the property also offers an impressive 1,188sf four-car garage plus an additional dedicated storage room - an exceptional amount of storage rarely found in a Keys home. Additional features include impact windows and doors throughout, metal roof, a paver driveway, and a cul-de-sac location. With expansive living and outdoor spaces, panoramic water views, 100' of deep water dockage, and Snake Creek just seconds away for convenient ocean-to-bay access, this Venetian Shores home offers a rare combination of space, storage, location, and boating convenience in the heart of Islamorada.

157 Valencia Dr, Islamorada

$4,600,000

This is an exceptionally rare chance to secure a versatile mixed use commercial property in Islamorada's most established business corridors. Sale does not include real estate business. These three building and the land are ideally positioned for a wide range of commercial uses. Its central location within the Village of Islamorada provides strong access to both local residents and year-round visitor activity, making it an appealing option for investors and owner-operators. The building features a practical, adaptable layout suitable for professional offices, medical or wellness services, boutique retail, administrative operations, or specialty businesses. Large front-facing windows bring in natural light and enhance street presence, creating an inviting entry point for customers and clients. The interior opens into a flexible main area that can function as a reception space, retail floor, open office environment, or showroom. The footprint also supports the creation of private offices, treatment rooms, or storage areas, allowing businesses to tailor the space to their operational needs. On-site parking adds significant value, providing convenient access for customers and employees--an important advantage in Islamorada's commercial zones. Excellent signage opportunities ensure strong brand exposure. Easy ingress and egress make the location suitable for both destination-based and walk-in business models. Surrounded by established businesses, restaurants, marinas, and residential neighborhoods, the property benefits from a diverse and active customer base. Islamorada's strong local economy and tourism-driven demand enhance the long-term appeal of this location. With limited standalone commercial inventory available in the Upper Keys, 81579 Old Highway offers a unique setting for multiple uses within walking distance to Cheeca Lodge, The Moorings, and Worl Wide Sportsman. Totally renovated in 2019. Virtual tour www.166bayviewdrive,com

1 Beds ⋅ 4 Baths ⋅ 618814 MLS

This is an exceptionally rare chance to secure a versatile mixed use commercial property in Islamorada's most established business corridors. Sale does not include real estate business. These three building and the land are ideally positioned for a wide range of commercial uses. Its central location within the Village of Islamorada provides strong access to both local residents and year-round visitor activity, making it an appealing option for investors and owner-operators. The building features a practical, adaptable layout suitable for professional offices, medical or wellness services, boutique retail, administrative operations, or specialty businesses. Large front-facing windows bring in natural light and enhance street presence, creating an inviting entry point for customers and clients. The interior opens into a flexible main area that can function as a reception space, retail floor, open office environment, or showroom. The footprint also supports the creation of private offices, treatment rooms, or storage areas, allowing businesses to tailor the space to their operational needs. On-site parking adds significant value, providing convenient access for customers and employees--an important advantage in Islamorada's commercial zones. Excellent signage opportunities ensure strong brand exposure. Easy ingress and egress make the location suitable for both destination-based and walk-in business models. Surrounded by established businesses, restaurants, marinas, and residential neighborhoods, the property benefits from a diverse and active customer base. Islamorada's strong local economy and tourism-driven demand enhance the long-term appeal of this location. With limited standalone commercial inventory available in the Upper Keys, 81579 Old Highway offers a unique setting for multiple uses within walking distance to Cheeca Lodge, The Moorings, and Worl Wide Sportsman. Totally renovated in 2019. Virtual tour www.166bayviewdrive,com

105 Palm Ave, Islamorada

$4,600,000

Welcome to paradise at 117 Leoni Drive in the exclusive Venetian Shores neighborhood! This stunning 4,100 sq. ft., canal-front home offers bay and ocean access via snake creek, 70 feet of dockage, and luxurious living with 5 bedrooms and 6 bathrooms. Built with precision and modern style, this brand-new custom CBS residence boasts lush landscaping, a sparkling pool, and high-end finishes throughout. Step upstairs to find a tranquil master suite with an expansive walk-in closet, a beverage center, a large shower, and dual vanities. Three additional guest suites with private bathrooms, a spacious living area, a large laundry room, and a versatile bonus room complete the upper level, providing ample space for relaxation and recreation. On the main floor, the gourmet kitchen is a chef's dream, featuring top-of-the-line appliances, storage pantry, Taj Mahal quartzite countertops, a wine cooler, and custom cabinetry throughout. A private guest room with an ensuite bathroom is perfect for the friends and family to visit for a staycation. The open-concept main living area flows seamlessly into the outdoors where a full bath and outdoor kitchen await. Relax by the lounge pool, enjoy synthetic grass surroundings, and take advantage of the full dock. This canal-front oasis is a rare find in the coveted Upper Keys and offers the perfect blend of luxury, comfort, and convenience. Your slice of paradise awaits!

5 Beds ⋅ 6 Baths ⋅ 617341 MLS

Welcome to paradise at 117 Leoni Drive in the exclusive Venetian Shores neighborhood! This stunning 4,100 sq. ft., canal-front home offers bay and ocean access via snake creek, 70 feet of dockage, and luxurious living with 5 bedrooms and 6 bathrooms. Built with precision and modern style, this brand-new custom CBS residence boasts lush landscaping, a sparkling pool, and high-end finishes throughout. Step upstairs to find a tranquil master suite with an expansive walk-in closet, a beverage center, a large shower, and dual vanities. Three additional guest suites with private bathrooms, a spacious living area, a large laundry room, and a versatile bonus room complete the upper level, providing ample space for relaxation and recreation. On the main floor, the gourmet kitchen is a chef's dream, featuring top-of-the-line appliances, storage pantry, Taj Mahal quartzite countertops, a wine cooler, and custom cabinetry throughout. A private guest room with an ensuite bathroom is perfect for the friends and family to visit for a staycation. The open-concept main living area flows seamlessly into the outdoors where a full bath and outdoor kitchen await. Relax by the lounge pool, enjoy synthetic grass surroundings, and take advantage of the full dock. This canal-front oasis is a rare find in the coveted Upper Keys and offers the perfect blend of luxury, comfort, and convenience. Your slice of paradise awaits!

117 Leoni Dr, Islamorada

$4,599,000

Seize Your Dream with Fast-Tracked Building Permits!** Unlock the potential to construct your ideal oceanfront retreat on this exceptional estate-sized lot. This stunning 1.5-acre parcel is completely cleared and filled to grade, allowing for an expedited permitting process. With the preexisting home already removed, you can start building in just two to three months after submitting your architectural plans. (ROGO exempt) This property has been divided into two parcels, offering the flexibility to create one or two homes, depending on your vision. It's perfectly situated in the heart of Marathon, just a short stroll away from the renowned Sombrero Beach and Park. Enjoy access to a scenic bike and walking path that meanders through the nearby golf course and connects to the Publix Shopping Center, the best beach in the Keys, and charming neighborhoods. You'll find Marathon International Airport, Fisherman's Hospital, and Home Depot within a quick five-minute drive. Marathon is known for its friendly fishing and diving community, boasting an array of restaurants and shops. The boating access from this lot can accommodate vessels with a draft of up to 4 feet, and a dock permit is already applied for and readily obtainable. Don't miss this rare opportunity to make your seaside dream a reality!

619871 MLS

Seize Your Dream with Fast-Tracked Building Permits!** Unlock the potential to construct your ideal oceanfront retreat on this exceptional estate-sized lot. This stunning 1.5-acre parcel is completely cleared and filled to grade, allowing for an expedited permitting process. With the preexisting home already removed, you can start building in just two to three months after submitting your architectural plans. (ROGO exempt) This property has been divided into two parcels, offering the flexibility to create one or two homes, depending on your vision. It's perfectly situated in the heart of Marathon, just a short stroll away from the renowned Sombrero Beach and Park. Enjoy access to a scenic bike and walking path that meanders through the nearby golf course and connects to the Publix Shopping Center, the best beach in the Keys, and charming neighborhoods. You'll find Marathon International Airport, Fisherman's Hospital, and Home Depot within a quick five-minute drive. Marathon is known for its friendly fishing and diving community, boasting an array of restaurants and shops. The boating access from this lot can accommodate vessels with a draft of up to 4 feet, and a dock permit is already applied for and readily obtainable. Don't miss this rare opportunity to make your seaside dream a reality!

88 Tingler Ln, Marathon

Experience the rare opportunity to own a brand-new waterfront residence in the heart of Key Colony Beach while still having the ability to personalize the finishes to reflect your own style. Currently under construction, this exceptional coastal home offers 4,596 square feet of thoughtfully designed living space with 4 spacious bedrooms, 3 full bathrooms, and 1 half bath. Designed for effortless indoor-outdoor living, the plans include a resort-style pool, expansive outdoor entertaining area with a fully equipped outdoor kitchen and bar, a two-car garage, plenty of storage, walk in laundry, and oversized bedrooms! Situated on an oversized 8,555-square-foot corner lot, the property also features 36 feet of concrete dockage, providing convenient access to the open waters of the Florida Keys for world class boating, fishing, and diving. This versatile location offers 7 day rental capabilities for those looking to purchase an income producing property, Vacation home or primary residence in an amenity rich community!

4 Beds ⋅ 4 Baths ⋅ 620400 MLS

Experience the rare opportunity to own a brand-new waterfront residence in the heart of Key Colony Beach while still having the ability to personalize the finishes to reflect your own style. Currently under construction, this exceptional coastal home offers 4,596 square feet of thoughtfully designed living space with 4 spacious bedrooms, 3 full bathrooms, and 1 half bath. Designed for effortless indoor-outdoor living, the plans include a resort-style pool, expansive outdoor entertaining area with a fully equipped outdoor kitchen and bar, a two-car garage, plenty of storage, walk in laundry, and oversized bedrooms! Situated on an oversized 8,555-square-foot corner lot, the property also features 36 feet of concrete dockage, providing convenient access to the open waters of the Florida Keys for world class boating, fishing, and diving. This versatile location offers 7 day rental capabilities for those looking to purchase an income producing property, Vacation home or primary residence in an amenity rich community!

1000 W Ocean Dr, Key Colony

Welcome to your slice of paradise in Marathon's highly sought-after ''Behind the Airport'' neighborhood. Live the ultimate Florida Keys lifestyle with unobstructed open water Gulf views, unforgettable sunsets, and exceptional outdoor living. Situated on an oversized 11,250 sq. ft. fenced lot, this 3-story CBS home offers 3 bedrooms, 2 bathrooms, and endless possibilities. Wake up each morning to panoramic water views from every level and spend your evenings watching the sun melt into the Gulf from multiple vantage points throughout the property. Boaters will appreciate the 80 foot dock direct access to world-class fishing, diving, and watersports. Nature lovers will enjoy the abundant marine life right in their backyard. Outdoor amenities abound with an in-ground swimming pool, two chickee huts, expansive entertaining area, and extensive storage space rarely found in the Keys. This is more than a home, it is a front-row seat to paradise.

3 Beds ⋅ 2 Baths ⋅ 620143 MLS

Welcome to your slice of paradise in Marathon's highly sought-after ''Behind the Airport'' neighborhood. Live the ultimate Florida Keys lifestyle with unobstructed open water Gulf views, unforgettable sunsets, and exceptional outdoor living. Situated on an oversized 11,250 sq. ft. fenced lot, this 3-story CBS home offers 3 bedrooms, 2 bathrooms, and endless possibilities. Wake up each morning to panoramic water views from every level and spend your evenings watching the sun melt into the Gulf from multiple vantage points throughout the property. Boaters will appreciate the 80 foot dock direct access to world-class fishing, diving, and watersports. Nature lovers will enjoy the abundant marine life right in their backyard. Outdoor amenities abound with an in-ground swimming pool, two chickee huts, expansive entertaining area, and extensive storage space rarely found in the Keys. This is more than a home, it is a front-row seat to paradise.

8070 Gulfstream Blvd, Marathon

Beautiful 100' of oceanfront property on Lower Matecumbe Key. This offering consists of a 100' lot with a triplex apartment building (3 TDRs),.This gives you lots of possibilities for redevelopment of the property. Fantastic near 180° ocean views make for gorgeous sunrises on the naturally sandy beaches. View Alligator Lighthouse, watch dolphins, manatees, and birds feeding on fish right in front of you. At night, beautiful full moon risings, cruise ships with their lights passing, and plenty of stars. Launch kayaks from the beach to do a little tarpon fishing and bonefish are making a comeback so you can wade with your fly rod for a thrill. Also snorkel for lobster in season in all the little crevices and holes off shore of the property. Note: One of the owners is a State of Florida Real Estate Licensee

3 Baths ⋅ 618928 MLS

Beautiful 100' of oceanfront property on Lower Matecumbe Key. This offering consists of a 100' lot with a triplex apartment building (3 TDRs),.This gives you lots of possibilities for redevelopment of the property. Fantastic near 180° ocean views make for gorgeous sunrises on the naturally sandy beaches. View Alligator Lighthouse, watch dolphins, manatees, and birds feeding on fish right in front of you. At night, beautiful full moon risings, cruise ships with their lights passing, and plenty of stars. Launch kayaks from the beach to do a little tarpon fishing and bonefish are making a comeback so you can wade with your fly rod for a thrill. Also snorkel for lobster in season in all the little crevices and holes off shore of the property. Note: One of the owners is a State of Florida Real Estate Licensee

75131 Overseas Hwy, Islamorada

Claim your position on one of Key Largo's most strategic stretches of water. This masterful new residence on Adams Cut delivers direct access to both ocean and bay. Two docks for serious boating, with a lift in place and room for a second. Whether you're running offshore at sunrise or cruising into the bay at golden hour, departure is effortless & return is even sweeter. The concrete structure exudes modern beauty w/low-maintenance ownership. Floor to ceiling impact windows frame 180 degrees around the floating concrete staircase that reads like an art piece. Entertaining is easy w/Wolf gas range, Subzero refrigerator, & beverage fridges. A private elevator services 3 stories. Second floor has a primary suite w/balcony overlooking the water, plus 2 more bedrooms. The top floor boasts a 2nd primary suite, and a full entertaining wing with/balcony & ample built-in bar ready to host game nights after a full day on the water. Outdoor paradise continues w/low-key turf, summer kitchen, and heated/chilled pool & spa. One car garage, Sonos system, & automated blinds using Control 4 & Lutron, are just a few features bolstering this home's lock-and-leave luxury allure. Key Largo is less than an hour from Miami, but worlds away in relaxation & mindset-the pinnacle of tropical living. This waterfront residence is built for those who understand the rhythm of the Keys — early departures, unhurried afternoons, & evenings defined by horizon lines rather than deadlines. A Very Special Home

4 Beds ⋅ 6 Baths ⋅ 618641 MLS

Claim your position on one of Key Largo's most strategic stretches of water. This masterful new residence on Adams Cut delivers direct access to both ocean and bay. Two docks for serious boating, with a lift in place and room for a second. Whether you're running offshore at sunrise or cruising into the bay at golden hour, departure is effortless & return is even sweeter. The concrete structure exudes modern beauty w/low-maintenance ownership. Floor to ceiling impact windows frame 180 degrees around the floating concrete staircase that reads like an art piece. Entertaining is easy w/Wolf gas range, Subzero refrigerator, & beverage fridges. A private elevator services 3 stories. Second floor has a primary suite w/balcony overlooking the water, plus 2 more bedrooms. The top floor boasts a 2nd primary suite, and a full entertaining wing with/balcony & ample built-in bar ready to host game nights after a full day on the water. Outdoor paradise continues w/low-key turf, summer kitchen, and heated/chilled pool & spa. One car garage, Sonos system, & automated blinds using Control 4 & Lutron, are just a few features bolstering this home's lock-and-leave luxury allure. Key Largo is less than an hour from Miami, but worlds away in relaxation & mindset-the pinnacle of tropical living. This waterfront residence is built for those who understand the rhythm of the Keys — early departures, unhurried afternoons, & evenings defined by horizon lines rather than deadlines. A Very Special Home

16 Bass Ave, Key Largo

$4,499,999

Located in the Beach Club, this reimagined residence offers a rare combination of luxury, privacy, and oceanfront living within one of Key West's premier & financially secure condo communities. This 3 bed, 3 bath residence encompasses 2,309 sq ft of thoughtfully designed living space with views of the Atlantic Ocean. Offered fully furnished, every detail has been curated to blend contemporary elegance with the relaxed refinement of island living. A robust high-speed WiFi system with multiple access points & 800 Mbps of service enhances the home's modern convenience. Walls of pocket glass doors frame endless ocean vistas while filling the living spaces with natural light. Designer lighting, Hunter Douglas Luminette sheer window treatments, and exceptional craftsmanship are showcased throughout. The kitchen features Miele appliances, integrated cabinet lighting, custom-organized drawers, and an innovative smart-glass circular window connecting the kitchen and dining area. With the touch of a button, the glass transitions from opaque to transparent. Designed for both entertaining and everyday living, the open-concept living and dining areas flow seamlessly. The dining space is highlighted by striking brass architectural lighting, while a custom-built bar with a wine cooler and ice maker creates an inviting entertaining alcove. The terrace extends the living space outdoors, offering a comfortable setting to enjoy the surrounding views. The primary suite features a distinctive white oak accent wall, built-in workspace and vanity with concealed power outlets, a spa-inspired bath, generous closet space, dual shoe closets, and a private waterfront terrace. One guest bedroom doubles as a media room with designer floral wall covering and club chairs that convert into twin beds. The third guest bedroom is a spacious ensuite retreat offering comfort and privacy. Residents enjoy gated access, exceptional amenities, covered deeded parking space, & private storage.

3 Beds ⋅ 3 Baths ⋅ 620745 MLS

Located in the Beach Club, this reimagined residence offers a rare combination of luxury, privacy, and oceanfront living within one of Key West's premier & financially secure condo communities. This 3 bed, 3 bath residence encompasses 2,309 sq ft of thoughtfully designed living space with views of the Atlantic Ocean. Offered fully furnished, every detail has been curated to blend contemporary elegance with the relaxed refinement of island living. A robust high-speed WiFi system with multiple access points & 800 Mbps of service enhances the home's modern convenience. Walls of pocket glass doors frame endless ocean vistas while filling the living spaces with natural light. Designer lighting, Hunter Douglas Luminette sheer window treatments, and exceptional craftsmanship are showcased throughout. The kitchen features Miele appliances, integrated cabinet lighting, custom-organized drawers, and an innovative smart-glass circular window connecting the kitchen and dining area. With the touch of a button, the glass transitions from opaque to transparent. Designed for both entertaining and everyday living, the open-concept living and dining areas flow seamlessly. The dining space is highlighted by striking brass architectural lighting, while a custom-built bar with a wine cooler and ice maker creates an inviting entertaining alcove. The terrace extends the living space outdoors, offering a comfortable setting to enjoy the surrounding views. The primary suite features a distinctive white oak accent wall, built-in workspace and vanity with concealed power outlets, a spa-inspired bath, generous closet space, dual shoe closets, and a private waterfront terrace. One guest bedroom doubles as a media room with designer floral wall covering and club chairs that convert into twin beds. The third guest bedroom is a spacious ensuite retreat offering comfort and privacy. Residents enjoy gated access, exceptional amenities, covered deeded parking space, & private storage.

1500 Atlantic Blvd Unit 308, Key West

$4,499,000

Some waterfront homes offer a view. This one creates an entire lifestyle around it. Set along the Gulf within the sought-after gated Stirrup Key community, this beautifully appointed CBS residence captures panoramic open-water views, unforgettable sunsets, and a rare sense of privacy. Electronic gated entry and tropical surroundings create an immediate sense of arrival while extensive upgrades reflect elevated living and effortless enjoyment. Contemporary design and relaxed coastal living come together through an open, light-filled floor plan. Expansive impact windows and sliding glass doors frame the water from every angle, bringing the ever-changing Gulf backdrop into the interior. The chef's kitchen features quartz countertops, Bosch stainless appliances, custom cabinetry, and a seamless connection to the dining and living areas. Solar panels further enhance the home's thoughtful, energy-conscious design. The thoughtfully designed layout includes two spacious primary suites, each offering private balcony access and sweeping water views. A third guest bedroom, guest bath, private gym, and an additional full bath add comfort and versatility. Outdoors, the property unfolds as a private tropical escape. A waterfront pool, covered entertaining area, outdoor shower, and multiple gathering spaces create the perfect setting for relaxed afternoons and memorable evenings. Mature fruit trees surround winding garden pathways leading to peaceful seating areas and a waterfront fire pit. A deeded boat slip with lift in the private marina is located just steps from the front door, offering exceptional convenience on the water. Along the open-water shoreline, a private kayak dock with lift provides direct access to exceptional kayaking and paddleboarding from your own backyard. Just minutes from shopping, dining, and The Marathon International Airport, this exceptional residence offers a rare combination of open-water beauty, boating access, privacy, and effortless island living.

3 Beds ⋅ 4 Baths ⋅ 620861 MLS

Some waterfront homes offer a view. This one creates an entire lifestyle around it. Set along the Gulf within the sought-after gated Stirrup Key community, this beautifully appointed CBS residence captures panoramic open-water views, unforgettable sunsets, and a rare sense of privacy. Electronic gated entry and tropical surroundings create an immediate sense of arrival while extensive upgrades reflect elevated living and effortless enjoyment. Contemporary design and relaxed coastal living come together through an open, light-filled floor plan. Expansive impact windows and sliding glass doors frame the water from every angle, bringing the ever-changing Gulf backdrop into the interior. The chef's kitchen features quartz countertops, Bosch stainless appliances, custom cabinetry, and a seamless connection to the dining and living areas. Solar panels further enhance the home's thoughtful, energy-conscious design. The thoughtfully designed layout includes two spacious primary suites, each offering private balcony access and sweeping water views. A third guest bedroom, guest bath, private gym, and an additional full bath add comfort and versatility. Outdoors, the property unfolds as a private tropical escape. A waterfront pool, covered entertaining area, outdoor shower, and multiple gathering spaces create the perfect setting for relaxed afternoons and memorable evenings. Mature fruit trees surround winding garden pathways leading to peaceful seating areas and a waterfront fire pit. A deeded boat slip with lift in the private marina is located just steps from the front door, offering exceptional convenience on the water. Along the open-water shoreline, a private kayak dock with lift provides direct access to exceptional kayaking and paddleboarding from your own backyard. Just minutes from shopping, dining, and The Marathon International Airport, this exceptional residence offers a rare combination of open-water beauty, boating access, privacy, and effortless island living.

108 Sunset Dr, Marathon

$4,495,000

There is a certain rhythm to life in Key West. Mornings begin outside, friends have a way of staying longer than planned, and some of the best evenings never make it past the backyard. 1614 Washington Street was designed for exactly that kind of life. Natural light, high ceilings, and an easy connection to the outdoors give the home an immediate sense of openness. The main living spaces flow naturally toward the pool and tropical garden, creating a setting that works just as well for a quiet morning at home as it does for dinner with friends that stretches late into the evening. The heated and chilled pool features two distinct levels--a shallow splash deck and a deeper swimming area--connected by cascading water features and surrounded by mature tropical landscaping that feels remarkably private. The floor plan understands that guests are part of island life, but privacy still matters. The first-floor primary suite creates a comfortable retreat for the owners, while upstairs, three en-suite bedrooms surround their own den and lounge. Family and friends can settle in, unpack, and have a space of their own rather than simply occupying yours. Behind that relaxed lifestyle is a house designed to make living here easier. Award-winning local architect Matthew Stratton brought together solid masonry construction, impact-rated windows and doors, solar power with Tesla battery storage, an EV charger, custom cabinetry, quartz surfaces, and thoughtful systems chosen for the realities of coastal living. The technology is there when you need it and nearly invisible when you don't. Morning walks, bike rides, the beach, neighborhood restaurants, galleries, and everything that makes Key West unlike anywhere else are simply part of the day. 1614 Washington invites you to open the doors, gather the people you love, jump in the pool, stay for dinner, and make yourself at home. Because ultimately, the best luxury isn't about having more. It's having a home that lets you live well.

4 Beds ⋅ 5 Baths ⋅ 618937 MLS

There is a certain rhythm to life in Key West. Mornings begin outside, friends have a way of staying longer than planned, and some of the best evenings never make it past the backyard. 1614 Washington Street was designed for exactly that kind of life. Natural light, high ceilings, and an easy connection to the outdoors give the home an immediate sense of openness. The main living spaces flow naturally toward the pool and tropical garden, creating a setting that works just as well for a quiet morning at home as it does for dinner with friends that stretches late into the evening. The heated and chilled pool features two distinct levels--a shallow splash deck and a deeper swimming area--connected by cascading water features and surrounded by mature tropical landscaping that feels remarkably private. The floor plan understands that guests are part of island life, but privacy still matters. The first-floor primary suite creates a comfortable retreat for the owners, while upstairs, three en-suite bedrooms surround their own den and lounge. Family and friends can settle in, unpack, and have a space of their own rather than simply occupying yours. Behind that relaxed lifestyle is a house designed to make living here easier. Award-winning local architect Matthew Stratton brought together solid masonry construction, impact-rated windows and doors, solar power with Tesla battery storage, an EV charger, custom cabinetry, quartz surfaces, and thoughtful systems chosen for the realities of coastal living. The technology is there when you need it and nearly invisible when you don't. Morning walks, bike rides, the beach, neighborhood restaurants, galleries, and everything that makes Key West unlike anywhere else are simply part of the day. 1614 Washington invites you to open the doors, gather the people you love, jump in the pool, stay for dinner, and make yourself at home. Because ultimately, the best luxury isn't about having more. It's having a home that lets you live well.

1614 Washington St, Key West

$4,490,000

Stunning Gulfside Waterfront Residence with Panoramic Water Views. Experience exceptional waterfront living in this 2022 built home featuring 5 bedrooms and 4.5 bathrooms, perfectly positioned on the Gulf side with breathtaking water views from nearly every room. The main level offers a bright and open layout designed for both comfort and entertainment. A spacious modern kitchen showcases elegant cabinetry, quartz countertops with a striking waterfall edge, and premium stainless-steel appliances. The kitchen flows seamlessly into the large dining and living areas, complete with a stylish wet bar, creating the perfect space for hosting and relaxing. This level also includes a convenient half bath and a utility room with laundry. Upstairs, the second-floor features five generously sized bedrooms and four full bathrooms. The expansive primary suite offers ample space, a beautifully designed modern bathroom, and a private porch where you can enjoy breathtaking sunset views over the water. Two additional bedrooms share a Jack-and-Jill bathroom and provide access to a balcony overlooking the pool and waterfront. A fourth bedroom, currently used as a home office, is located near another full hallway bathroom. The fifth bedroom is a private suite with its own ensuite bathroom. Outdoor living is just as impressive, featuring a large patio area ideal for entertaining, a spacious pool, and a 55-foot dock, making this property perfect for boating enthusiasts and waterfront relaxation. Additional highlights include a large two-car plus garage with ample storage space. This exceptional property combines modern design, generous living space, and stunning Gulfside views, creating a truly remarkable coastal home offering excellent convenience for boat owners. Boat Lift plans have already been approved and permits granted and available.

5 Beds ⋅ 5 Baths ⋅ 619048 MLS

Stunning Gulfside Waterfront Residence with Panoramic Water Views. Experience exceptional waterfront living in this 2022 built home featuring 5 bedrooms and 4.5 bathrooms, perfectly positioned on the Gulf side with breathtaking water views from nearly every room. The main level offers a bright and open layout designed for both comfort and entertainment. A spacious modern kitchen showcases elegant cabinetry, quartz countertops with a striking waterfall edge, and premium stainless-steel appliances. The kitchen flows seamlessly into the large dining and living areas, complete with a stylish wet bar, creating the perfect space for hosting and relaxing. This level also includes a convenient half bath and a utility room with laundry. Upstairs, the second-floor features five generously sized bedrooms and four full bathrooms. The expansive primary suite offers ample space, a beautifully designed modern bathroom, and a private porch where you can enjoy breathtaking sunset views over the water. Two additional bedrooms share a Jack-and-Jill bathroom and provide access to a balcony overlooking the pool and waterfront. A fourth bedroom, currently used as a home office, is located near another full hallway bathroom. The fifth bedroom is a private suite with its own ensuite bathroom. Outdoor living is just as impressive, featuring a large patio area ideal for entertaining, a spacious pool, and a 55-foot dock, making this property perfect for boating enthusiasts and waterfront relaxation. Additional highlights include a large two-car plus garage with ample storage space. This exceptional property combines modern design, generous living space, and stunning Gulfside views, creating a truly remarkable coastal home offering excellent convenience for boat owners. Boat Lift plans have already been approved and permits granted and available.

865 50th St, Marathon

$4,475,000

Nestled along the Florida Bay in exclusive Buccaneer Point, this exquisite bay front estate offers an unparalleled fusion of opulence, tranquility, and sweeping water views, redefining luxury living in the Florida Keys. Perfectly positioned at the tip of the peninsula, this exceptional property offers breathtaking panoramic views of the bay from every major living area. Experience unrivaled privacy and serenity with conservation land bordering the property to the West, ensuring unobstructed vistas and a tranquil setting. This meticulously updated 5-bedroom, 4-bathroom estate combines modern elegance with resort-style amenities. The open-concept gourmet kitchen is a chef's delight, featuring high-end appliances, custom cabinetry, and seamless flow into the expansive living and dining spaces--all with stunning water views. A sleek glass elevator provides effortless access to all levels, making every part of this home easily accessible. Step outside to your personal paradise: a lush backyard with low-maintenance turf, a custom putting green, and an inground pool equipped with heaters for year-round comfort. Boating enthusiasts will appreciate the 15,000-pound boat lift, offering direct access to the bay for endless adventures on the water. Additional highlights include a spacious two-car garage, ample storage, and a quiet cul-de-sac location that ensures privacy. Whether you're relaxing poolside, savoring sunsets from the expansive balcony, or entertaining guests in style, this home truly embodies the ultimate in luxury coastal living. Don't miss the rare opportunity to own this spectacular bayfront retreat in coveted Buccaneer Point Estates--schedule your private showing today!

5 Beds ⋅ 4 Baths ⋅ 619382 MLS

Nestled along the Florida Bay in exclusive Buccaneer Point, this exquisite bay front estate offers an unparalleled fusion of opulence, tranquility, and sweeping water views, redefining luxury living in the Florida Keys. Perfectly positioned at the tip of the peninsula, this exceptional property offers breathtaking panoramic views of the bay from every major living area. Experience unrivaled privacy and serenity with conservation land bordering the property to the West, ensuring unobstructed vistas and a tranquil setting. This meticulously updated 5-bedroom, 4-bathroom estate combines modern elegance with resort-style amenities. The open-concept gourmet kitchen is a chef's delight, featuring high-end appliances, custom cabinetry, and seamless flow into the expansive living and dining spaces--all with stunning water views. A sleek glass elevator provides effortless access to all levels, making every part of this home easily accessible. Step outside to your personal paradise: a lush backyard with low-maintenance turf, a custom putting green, and an inground pool equipped with heaters for year-round comfort. Boating enthusiasts will appreciate the 15,000-pound boat lift, offering direct access to the bay for endless adventures on the water. Additional highlights include a spacious two-car garage, ample storage, and a quiet cul-de-sac location that ensures privacy. Whether you're relaxing poolside, savoring sunsets from the expansive balcony, or entertaining guests in style, this home truly embodies the ultimate in luxury coastal living. Don't miss the rare opportunity to own this spectacular bayfront retreat in coveted Buccaneer Point Estates--schedule your private showing today!

51 Mutiny Pl, Key Largo

$4,450,000

Experience the ideal blend of historic charm and modern luxury in this fully renovated and expanded Key West residence, where no detail has been overlooked. Set on a quiet, one-way street in Old Town, this 4-bedroom, 4.5-bath home offers 2,985 square feet of thoughtfully designed living space. Inside, soaring cathedral ceilings and rich Dade County pine walls create a warm, timeless aesthetic. Gorgeous hickory wood floors run throughout, complemented by two custom staircases and striking architectural features. The flexible layout includes a first-floor primary suite with a spa-style bath finished in marble and travertine, plus a second primary suite upstairs that also includes a private office—providing options for comfort, work, and privacy. All of the bathrooms are designed with a serene, spa-like feel, and every upstairs bath includes its own soaking tub for ultimate relaxation. The gourmet kitchen features Miele appliances along with a custom bar complete with a duel zone wine cooler and beverage center—ideal for effortless entertaining. Outdoors, an Ipe deck surrounds the heated and chilled saltwater pool with cascading waterfall features, all controlled by a smart automation system. At the top of the water wall, a decorative propane fire feature adds a dramatic focal point, while an outdoor shower completes your private tropical retreat. Additional features include two off-street parking spaces, impact-rated windows and doors throughout, metal shingle roof and dual-zone central A/C. With designer furnishings included and sold exactly as presented, this residence is ready to enjoy in the heart of Key West's most desirable locations.

4 Beds ⋅ 5 Baths ⋅ 616715 MLS

Experience the ideal blend of historic charm and modern luxury in this fully renovated and expanded Key West residence, where no detail has been overlooked. Set on a quiet, one-way street in Old Town, this 4-bedroom, 4.5-bath home offers 2,985 square feet of thoughtfully designed living space. Inside, soaring cathedral ceilings and rich Dade County pine walls create a warm, timeless aesthetic. Gorgeous hickory wood floors run throughout, complemented by two custom staircases and striking architectural features. The flexible layout includes a first-floor primary suite with a spa-style bath finished in marble and travertine, plus a second primary suite upstairs that also includes a private office—providing options for comfort, work, and privacy. All of the bathrooms are designed with a serene, spa-like feel, and every upstairs bath includes its own soaking tub for ultimate relaxation. The gourmet kitchen features Miele appliances along with a custom bar complete with a duel zone wine cooler and beverage center—ideal for effortless entertaining. Outdoors, an Ipe deck surrounds the heated and chilled saltwater pool with cascading waterfall features, all controlled by a smart automation system. At the top of the water wall, a decorative propane fire feature adds a dramatic focal point, while an outdoor shower completes your private tropical retreat. Additional features include two off-street parking spaces, impact-rated windows and doors throughout, metal shingle roof and dual-zone central A/C. With designer furnishings included and sold exactly as presented, this residence is ready to enjoy in the heart of Key West's most desirable locations.

1113 Stump Ln, Key West

$4,445,000

Venetian Shores, the premier waterfront community in Islamorada!!! Looking for that larger than life home, well this is it! We have an 8 bedroom, 4 baths a pool, with nearly 5,000 sq. ft. of living area. Quick access to the Atlantic Ocean and Florida Bay with in minutes via Snake Creek. What makes this location unique is the 100 foot wide, deep water canals and what make this property more unique and valuable than others, we offer 100 linear feet of dockage. There is a 30,000 pound lift for your large boats and a 10,000 lift for your smaller boats. And there is still room for another vessel or personal water crafts. This home offers three levels, the main level has three bedrooms a full bath a kitchenette and living area with great views of the water. The second level, large living area with soaring ceilings, a massive kitchen, 2 bedrooms and a full bath. The third level offers 3 bedrooms and 2 full baths. There is an abundant pool and bar area for entertaining family and friends. Looking for a home to accommodate the large extended family, this is it or put it out in the Airbnb world, it would make a great income property.

8 Beds ⋅ 4 Baths ⋅ 619083 MLS

Venetian Shores, the premier waterfront community in Islamorada!!! Looking for that larger than life home, well this is it! We have an 8 bedroom, 4 baths a pool, with nearly 5,000 sq. ft. of living area. Quick access to the Atlantic Ocean and Florida Bay with in minutes via Snake Creek. What makes this location unique is the 100 foot wide, deep water canals and what make this property more unique and valuable than others, we offer 100 linear feet of dockage. There is a 30,000 pound lift for your large boats and a 10,000 lift for your smaller boats. And there is still room for another vessel or personal water crafts. This home offers three levels, the main level has three bedrooms a full bath a kitchenette and living area with great views of the water. The second level, large living area with soaring ceilings, a massive kitchen, 2 bedrooms and a full bath. The third level offers 3 bedrooms and 2 full baths. There is an abundant pool and bar area for entertaining family and friends. Looking for a home to accommodate the large extended family, this is it or put it out in the Airbnb world, it would make a great income property.

136 San Remo Dr, Islamorada

An exceptional opportunity to own one of Old Town Key West's most recognizable mixed-use investment properties. Perfectly positioned at the prominent corner of Whitehead Street and Front Street, Little Shops Off Duval enjoys unmatched pedestrian exposure in the heart of the Historic Seaport and Cruise Ship District. Located adjacent to the Mel Fisher Maritime Museum and directly across from the Audubon House, this iconic property sits along one of the busiest tourist corridors in Key West. The property encompasses approximately 7,755 square feet and features six established commercial storefronts together with a spacious three-bedroom, two-bath residential apartment, creating a diversified income-producing asset with both commercial and residential revenue streams. Long-standing tenants, and separate utility meters. Opportunities to acquire a premier corner property in this location are exceptionally rare. Whether you're seeking a legacy investment, a trophy commercial asset, or a high-profile addition to your portfolio, Little Shops Off Duval represents one of the most unique commercial ownership opportunities in the Florida Keys.

3 Beds ⋅ 5 Baths ⋅ 620614 MLS

An exceptional opportunity to own one of Old Town Key West's most recognizable mixed-use investment properties. Perfectly positioned at the prominent corner of Whitehead Street and Front Street, Little Shops Off Duval enjoys unmatched pedestrian exposure in the heart of the Historic Seaport and Cruise Ship District. Located adjacent to the Mel Fisher Maritime Museum and directly across from the Audubon House, this iconic property sits along one of the busiest tourist corridors in Key West. The property encompasses approximately 7,755 square feet and features six established commercial storefronts together with a spacious three-bedroom, two-bath residential apartment, creating a diversified income-producing asset with both commercial and residential revenue streams. Long-standing tenants, and separate utility meters. Opportunities to acquire a premier corner property in this location are exceptionally rare. Whether you're seeking a legacy investment, a trophy commercial asset, or a high-profile addition to your portfolio, Little Shops Off Duval represents one of the most unique commercial ownership opportunities in the Florida Keys.

218 Whitehead St, Key West

Now priced UNDER recent appraised value of $4,500,000! Embrace the RARE opportunity to own 1.75 acres of open water paradise in the prestigious, gated community of Stirrup Key. Over 600' feet of direct, open Gulf frontage, you'll enjoy spectacular sunrises and sunsets from nearly every vantage point, including a charming sunset gazebo overlooking the iconic Seven Mile Bridge in the distance. The custom Mediterranean-style residence captures the essence of resort living with expansive pavered patios, sparkling elevated pool, and spacious lounging areas absolutely perfect for entertaining against a stunning Gulf backdrop. Five protected basin docks provide sheltered boating access in the marina, while terraced tropical gardens cascade toward the water, lined with mature palms and lush landscaping for a serene coastal ambiance. Inside, soaring cathedral ceilings, wood plantation shutters, and an airy great room with real coral fireplace showcase timeless Keys craftsmanship. The split-bedroom layout ensures privacy, with a luxurious master suite featuring dual closets and skylit bath, plus separate guest quarters. Additional highlights include an elevator, 12,000-gallon cistern, huge garage for cars and golf carts, and a large lower-level storage area with workbenches, pool table, and extra laundry facilities. This gated community, with unique architecture, fewer lots, limited rentals and higher quality restrictions help to sustain a premium and private feel. Only minutes from the Marathon Airport, this one-of-a-kind estate combines open-water grandeur with island tranquility, a true Florida Keys sanctuary.

3 Beds ⋅ 4 Baths ⋅ 619002 MLS

Now priced UNDER recent appraised value of $4,500,000! Embrace the RARE opportunity to own 1.75 acres of open water paradise in the prestigious, gated community of Stirrup Key. Over 600' feet of direct, open Gulf frontage, you'll enjoy spectacular sunrises and sunsets from nearly every vantage point, including a charming sunset gazebo overlooking the iconic Seven Mile Bridge in the distance. The custom Mediterranean-style residence captures the essence of resort living with expansive pavered patios, sparkling elevated pool, and spacious lounging areas absolutely perfect for entertaining against a stunning Gulf backdrop. Five protected basin docks provide sheltered boating access in the marina, while terraced tropical gardens cascade toward the water, lined with mature palms and lush landscaping for a serene coastal ambiance. Inside, soaring cathedral ceilings, wood plantation shutters, and an airy great room with real coral fireplace showcase timeless Keys craftsmanship. The split-bedroom layout ensures privacy, with a luxurious master suite featuring dual closets and skylit bath, plus separate guest quarters. Additional highlights include an elevator, 12,000-gallon cistern, huge garage for cars and golf carts, and a large lower-level storage area with workbenches, pool table, and extra laundry facilities. This gated community, with unique architecture, fewer lots, limited rentals and higher quality restrictions help to sustain a premium and private feel. Only minutes from the Marathon Airport, this one-of-a-kind estate combines open-water grandeur with island tranquility, a true Florida Keys sanctuary.

111 Windy Point Cir Unit & Lot 78, Marathon

Rarely available, this 8,190 SF vacant homesite sits along a deep water canal on Duck Key, with open ocean views that are simply priceless. The lot already includes a concrete dock, boat lift, and seawall, giving boaters immediate deep water access without the wait or expense of new construction. That same seawall will provide lasting storm and wave protection for whatever home is built here. Because a home previously stood on this site, the lot is ROGO exempt, meaning you can build without competing in Monroe County's growth ordinance lottery, a rare and valuable advantage in the Florida Keys. Located next to Hawks Cay Resort, residents enjoy easy access to dolphin swims, dining by a Michelin rated chef, and a full service marina. Duck Key sits centrally in the Middle Keys, close to luxury restaurants, the Grassy Key sandbar, deep drops for offshore fishing, clear Bahamian like waters, nearby reefs for lobstering and reef fishing, and the Islamorada Humps for tuna. Weekly rentals are not permitted on the island, preserving a quiet, residential feel with more full time locals than tourists. Bring your builder and bring your vision, this is a rare opportunity to create your dream home on one of the best kept secrets in the Keys. Schedule a viewing today.

618564 MLS

Rarely available, this 8,190 SF vacant homesite sits along a deep water canal on Duck Key, with open ocean views that are simply priceless. The lot already includes a concrete dock, boat lift, and seawall, giving boaters immediate deep water access without the wait or expense of new construction. That same seawall will provide lasting storm and wave protection for whatever home is built here. Because a home previously stood on this site, the lot is ROGO exempt, meaning you can build without competing in Monroe County's growth ordinance lottery, a rare and valuable advantage in the Florida Keys. Located next to Hawks Cay Resort, residents enjoy easy access to dolphin swims, dining by a Michelin rated chef, and a full service marina. Duck Key sits centrally in the Middle Keys, close to luxury restaurants, the Grassy Key sandbar, deep drops for offshore fishing, clear Bahamian like waters, nearby reefs for lobstering and reef fishing, and the Islamorada Humps for tuna. Weekly rentals are not permitted on the island, preserving a quiet, residential feel with more full time locals than tourists. Bring your builder and bring your vision, this is a rare opportunity to create your dream home on one of the best kept secrets in the Keys. Schedule a viewing today.

318 E Seaview Cir, Duck

Experience the charm and character of this Gulf-front Old Florida Keys fishing lodge located in Stirrup Key, one of Marathon's most exclusive gated communities. Known for its large estate lots, deep-water access, and serene open-Gulf vistas, Stirrup Key offers privacy, prestige, and a true island lifestyle, just minutes from the conveniences of Marathon. The property consists of two lots in total for a combined size of 39,500 sf. The home sits on one of the few deep-water sites in Stirrup Key with upgraded 165 foot pier dock with 6 new pilings, where the water is so clear you can watch tarpon, angelfish, snapper, nurse sharks, lobsters and rays gliding beneath the dock. Beautifully maintained and elevated above flood, the residence features 3 bedrooms, 3 baths, and a loft that can serve as a fourth bedroom or home office. Brand new roof and impact windows and sliders were recently installed for peace of mind. The open-concept great room boasts massive ceilings and walls of windows showcasing 180-degree Gulf views. A spacious kitchen with center island and new range, Gulf front bar, wide overhanging eaves, exposed wood beams, and natural stone accents showcase classic tropical lodge architecture, perfect for entertaining. The primary suite with a large ensuite bath provide comfort and style, while a screened porch opens to the heated pool, positioned behind lush landscaping for afternoon shade. Outdoors, you'll find a sandy beach area, irrigated native landscaping, and expansive decks perfect for sunset gatherings. Additional amenities include two garage bays, one carport bay, a workshop, garden shed, and abundant storage. Stirrup Key residents enjoy the peace of a gated, low-density community with a 365 day rental minimum, ensuring tranquility and exclusivity year-round. With its unmatched combination of deep water, open-Gulf views, and spacious multi-lot layout, this property is a true rarity in the Florida Keys with potential for expansion.

3 Beds ⋅ 3 Baths ⋅ 617542 MLS

Experience the charm and character of this Gulf-front Old Florida Keys fishing lodge located in Stirrup Key, one of Marathon's most exclusive gated communities. Known for its large estate lots, deep-water access, and serene open-Gulf vistas, Stirrup Key offers privacy, prestige, and a true island lifestyle, just minutes from the conveniences of Marathon. The property consists of two lots in total for a combined size of 39,500 sf. The home sits on one of the few deep-water sites in Stirrup Key with upgraded 165 foot pier dock with 6 new pilings, where the water is so clear you can watch tarpon, angelfish, snapper, nurse sharks, lobsters and rays gliding beneath the dock. Beautifully maintained and elevated above flood, the residence features 3 bedrooms, 3 baths, and a loft that can serve as a fourth bedroom or home office. Brand new roof and impact windows and sliders were recently installed for peace of mind. The open-concept great room boasts massive ceilings and walls of windows showcasing 180-degree Gulf views. A spacious kitchen with center island and new range, Gulf front bar, wide overhanging eaves, exposed wood beams, and natural stone accents showcase classic tropical lodge architecture, perfect for entertaining. The primary suite with a large ensuite bath provide comfort and style, while a screened porch opens to the heated pool, positioned behind lush landscaping for afternoon shade. Outdoors, you'll find a sandy beach area, irrigated native landscaping, and expansive decks perfect for sunset gatherings. Additional amenities include two garage bays, one carport bay, a workshop, garden shed, and abundant storage. Stirrup Key residents enjoy the peace of a gated, low-density community with a 365 day rental minimum, ensuring tranquility and exclusivity year-round. With its unmatched combination of deep water, open-Gulf views, and spacious multi-lot layout, this property is a true rarity in the Florida Keys with potential for expansion.

115 Windy Point Cir, Marathon