Realestateinthefloridakeys.com Search Results

Some homes invite you in, and others make you want to stay. 1220 Georgia Street does both. Tucked into a quiet pocket of Old Town on a corner lot, the home feels peaceful and removed, yet everything you need is just moments away. A short walk takes you to neighborhood cafes, the beach, or a quick bike ride into the heart of town, while at home, the pace feels slower and more relaxed. The approach sets the tone. A marble and Coralina pathway leads through lush landscaping to a welcoming front porch and a striking antique front door that hints at the character inside. Step through and the space opens up with high ceilings and large windows that fill the home with natural light. The living areas flow easily together and draw you toward the outdoors, where a private backyard retreat awaits. Surrounded by mature tropical foliage, the cocktail pool and IPE deck create a setting that feels both secluded and inviting, perfect for entertaining or unwinding. The main house offers 3 bedrooms and 2 bathrooms, complemented by a separate 1 bedroom and 1 bathroom guest cottage that provides flexibility for visitors or a quiet escape. This is a home that feels well cared for, loved, and ready for its next chapter. A place where the details matter, but the feeling matters even more.

4 Beds ⋅ 3 Baths ⋅ 619619 MLS

Some homes invite you in, and others make you want to stay. 1220 Georgia Street does both. Tucked into a quiet pocket of Old Town on a corner lot, the home feels peaceful and removed, yet everything you need is just moments away. A short walk takes you to neighborhood cafes, the beach, or a quick bike ride into the heart of town, while at home, the pace feels slower and more relaxed. The approach sets the tone. A marble and Coralina pathway leads through lush landscaping to a welcoming front porch and a striking antique front door that hints at the character inside. Step through and the space opens up with high ceilings and large windows that fill the home with natural light. The living areas flow easily together and draw you toward the outdoors, where a private backyard retreat awaits. Surrounded by mature tropical foliage, the cocktail pool and IPE deck create a setting that feels both secluded and inviting, perfect for entertaining or unwinding. The main house offers 3 bedrooms and 2 bathrooms, complemented by a separate 1 bedroom and 1 bathroom guest cottage that provides flexibility for visitors or a quiet escape. This is a home that feels well cared for, loved, and ready for its next chapter. A place where the details matter, but the feeling matters even more.

1220 Georgia St, Key West

$1,899,000

Rare opportunity to acquire SEVEN units in the X-Flood Zone in Old Town Key West. That's correct, seven market rate units! Renovations in progress! Priced at less than $272K per unit! Recent changes to IRS tax code (such as accelerated depreciation) can benefit RE Investors - ask your tax expert. Prime Old Town location, just 1/2 block from cemetery and 1/2 block off Truman Ave. Currently configured as 6 units (but City recognizes 7). Presently being used as: one 2-bedroom unit, three 1-bedroom units and 2 studio units. All with separate exterior entrances. Convenient location is close to many Old Town attractions including world famous Duval St. Perfect for employee housing or income producing multi-unit property. Advanced notice required before showings and don't expect to see all six of the units at once. Please do NOT disturb tenants. This is a duplicate entry.

7 Beds ⋅ 6 Baths ⋅ 615914 MLS

Rare opportunity to acquire SEVEN units in the X-Flood Zone in Old Town Key West. That's correct, seven market rate units! Renovations in progress! Priced at less than $272K per unit! Recent changes to IRS tax code (such as accelerated depreciation) can benefit RE Investors - ask your tax expert. Prime Old Town location, just 1/2 block from cemetery and 1/2 block off Truman Ave. Currently configured as 6 units (but City recognizes 7). Presently being used as: one 2-bedroom unit, three 1-bedroom units and 2 studio units. All with separate exterior entrances. Convenient location is close to many Old Town attractions including world famous Duval St. Perfect for employee housing or income producing multi-unit property. Advanced notice required before showings and don't expect to see all six of the units at once. Please do NOT disturb tenants. This is a duplicate entry.

909 Grinnell St, Key West

$1,899,000

Discover the essence of island living in this expansive 3,197sf, 6-bedroom, 3-bathroom home, perfectly positioned on a generous 9,500sf corner lot in the heart of Key West. This spacious 2 story CBS home features a gourmet kitchen, tile floors, 2 laundry areas, sundeck & a new roof. The sprawling yard, enclosed by a privacy wall, offers plenty of room for boat and trailer storage, RV parking, and a safe play area for kids and pets. An in-ground concrete pool with water feature adds to the outdoor appeal, while a storage shed provides extra convenience. Offering a rare combination of convenience and space, this residence is ideally located minutes from schools & grocery stores, while also being near the new Happy Landings Marina and the Key West Yacht Club, making boating a breeze! With a flexible layout and ample space, this property is brimming with possibilities, ready to be tailored to your vision of the perfect island retreat.

6 Beds ⋅ 3 Baths ⋅ 611164 MLS

Discover the essence of island living in this expansive 3,197sf, 6-bedroom, 3-bathroom home, perfectly positioned on a generous 9,500sf corner lot in the heart of Key West. This spacious 2 story CBS home features a gourmet kitchen, tile floors, 2 laundry areas, sundeck & a new roof. The sprawling yard, enclosed by a privacy wall, offers plenty of room for boat and trailer storage, RV parking, and a safe play area for kids and pets. An in-ground concrete pool with water feature adds to the outdoor appeal, while a storage shed provides extra convenience. Offering a rare combination of convenience and space, this residence is ideally located minutes from schools & grocery stores, while also being near the new Happy Landings Marina and the Key West Yacht Club, making boating a breeze! With a flexible layout and ample space, this property is brimming with possibilities, ready to be tailored to your vision of the perfect island retreat.

1229 5th St, Key West

$1,899,000

Rare opportunity to acquire SEVEN units in the X-Flood Zone in Old Town Key West. That's correct, seven market rate units! That's less than $272K per unit! Renovations in progress. Recent changes to IRS tax code (such as accelerated depreciation) can benefit RE Investors - ask your tax expert. Prime location, just 1/2 block from cemetery and 1/2 block off Truman Ave. Currently configured as 6 units (but City recognizes 7). Presently being used as: one 2-bedroom unit, three 1-bedroom units and 2 studio units. All with separate exterior entrances. Convenient location is close to many Old Town hot spots including world famous Duval St.. Perfect for employee housing or income producing multi-unit property. Advanced notice required before showings and don't expect to see all six of the units at once. Please do NOT disturb tenants. This is a duplicate entry.

7 Beds ⋅ 6 Baths ⋅ 615913 MLS

Rare opportunity to acquire SEVEN units in the X-Flood Zone in Old Town Key West. That's correct, seven market rate units! That's less than $272K per unit! Renovations in progress. Recent changes to IRS tax code (such as accelerated depreciation) can benefit RE Investors - ask your tax expert. Prime location, just 1/2 block from cemetery and 1/2 block off Truman Ave. Currently configured as 6 units (but City recognizes 7). Presently being used as: one 2-bedroom unit, three 1-bedroom units and 2 studio units. All with separate exterior entrances. Convenient location is close to many Old Town hot spots including world famous Duval St.. Perfect for employee housing or income producing multi-unit property. Advanced notice required before showings and don't expect to see all six of the units at once. Please do NOT disturb tenants. This is a duplicate entry.

909 Grinnell St, Key West

$1,899,000

Located on a corner lot in the highly sought-after Meadows neighborhood, this beautifully crafted Key West home offers exceptional design, privacy, and outdoor living. Built new in 2008 with top-of-the-line materials and superior craftsmanship, the residence features 2 bedrooms, 2.5 baths, and dramatic architectural details throughout. Upon entry, you are welcomed by soaring 11-foot ceilings and an expansive open living space highlighted by travertine tile flooring and abundant natural light. Eight-foot hurricane-rated sliding glass doors seamlessly connect the interior to a private, beautifully landscaped patio with a heated pool and spa--perfect for entertaining or relaxing in your own tropical retreat. The gourmet kitchen overlooks the living area and is appointed with custom solid wood cabinetry, granite countertops, and premium stainless steel appliances, including a six-burner gas range. Rich hardwood floors continue throughout the home, complemented by crown molding, high baseboards, and custom trim. Upstairs, both guest and primary suites are designed for comfort and privacy. The guest suite features its own private staircase, vaulted tray ceiling, and ensuite bath. The spacious primary suite is a true sanctuary, offering vaulted ceilings, multiple closets, abundant natural light, and access to a wide private balcony. The luxurious primary bath adds to the home's refined appeal. Additional features include Hardiboard siding, impact windows and doors, a metal roof, and a private carport with storage accessed through electronic gates. The fully fenced property is surrounded by lush tropical landscaping and is adjacent to a protected basin with native tropical flora, enhancing privacy and tranquility. Enjoy easy, low-maintenance living just a short stroll to Old Town and the Seaport--this is island living at its finest.

2 Beds ⋅ 3 Baths ⋅ 618826 MLS

Located on a corner lot in the highly sought-after Meadows neighborhood, this beautifully crafted Key West home offers exceptional design, privacy, and outdoor living. Built new in 2008 with top-of-the-line materials and superior craftsmanship, the residence features 2 bedrooms, 2.5 baths, and dramatic architectural details throughout. Upon entry, you are welcomed by soaring 11-foot ceilings and an expansive open living space highlighted by travertine tile flooring and abundant natural light. Eight-foot hurricane-rated sliding glass doors seamlessly connect the interior to a private, beautifully landscaped patio with a heated pool and spa--perfect for entertaining or relaxing in your own tropical retreat. The gourmet kitchen overlooks the living area and is appointed with custom solid wood cabinetry, granite countertops, and premium stainless steel appliances, including a six-burner gas range. Rich hardwood floors continue throughout the home, complemented by crown molding, high baseboards, and custom trim. Upstairs, both guest and primary suites are designed for comfort and privacy. The guest suite features its own private staircase, vaulted tray ceiling, and ensuite bath. The spacious primary suite is a true sanctuary, offering vaulted ceilings, multiple closets, abundant natural light, and access to a wide private balcony. The luxurious primary bath adds to the home's refined appeal. Additional features include Hardiboard siding, impact windows and doors, a metal roof, and a private carport with storage accessed through electronic gates. The fully fenced property is surrounded by lush tropical landscaping and is adjacent to a protected basin with native tropical flora, enhancing privacy and tranquility. Enjoy easy, low-maintenance living just a short stroll to Old Town and the Seaport--this is island living at its finest.

1513 Pine St, Key West

$1,898,000

Just half a block from Duval Street and steps from South Beach and the iconic Southernmost Point, this beautifully renovated 2,205 sq. ft. historic Conch home offers the perfect blend of timeless Key West charm and modern luxury. Ideally situated in the vibrant heart of Old Town, the home is just a short stroll from exceptional restaurants, acclaimed art galleries, boutique shopping, beautiful beaches, and some of Key West's most celebrated attractions. Thoughtfully transformed into an elegant single-family residence, the home retains original Dade County pine floors and walls alongside extensive upgrades, including a gourmet kitchen, updated plumbing, 300-amp electrical service, new ACs, custom windows and a metal roof. The bright, open main level flows from inviting living and dining areas into a chef's kitchen with custom cabinetry, generous counter space, and an arched pass-through with bar seating. The kitchen overlooks a lush tropical oasis, featuring a heated and chilled pool and covered pergola, perfect for alfresco dining, relaxation, and entertaining under the Southernmost skies. The second floor offers two spacious guest bedrooms, a full bath, office nook, and balcony with glimpses of the ocean and Southernmost House. The entire third floor is a private primary suite with a walk-in closet, built-in quartz-topped storage, and spa-inspired bath with dual vanities and rainfall shower. Embrace effortless island living with ample bicycle and scooter parking and residential permit street parking for eligible residents. Fully furnished and turnkey, this low-maintenance retreat invites you to bring your toothbrush and explore Key West lifestyle from day one. Formerly configured as a duplex, the property also offers potential to restore two legal residences and create separate income streams, subject to verification and approvals. Schedule your private showing today to experience all this ideal property has to offer.

3 Beds ⋅ 3 Baths ⋅ 622063 MLS

Just half a block from Duval Street and steps from South Beach and the iconic Southernmost Point, this beautifully renovated 2,205 sq. ft. historic Conch home offers the perfect blend of timeless Key West charm and modern luxury. Ideally situated in the vibrant heart of Old Town, the home is just a short stroll from exceptional restaurants, acclaimed art galleries, boutique shopping, beautiful beaches, and some of Key West's most celebrated attractions. Thoughtfully transformed into an elegant single-family residence, the home retains original Dade County pine floors and walls alongside extensive upgrades, including a gourmet kitchen, updated plumbing, 300-amp electrical service, new ACs, custom windows and a metal roof. The bright, open main level flows from inviting living and dining areas into a chef's kitchen with custom cabinetry, generous counter space, and an arched pass-through with bar seating. The kitchen overlooks a lush tropical oasis, featuring a heated and chilled pool and covered pergola, perfect for alfresco dining, relaxation, and entertaining under the Southernmost skies. The second floor offers two spacious guest bedrooms, a full bath, office nook, and balcony with glimpses of the ocean and Southernmost House. The entire third floor is a private primary suite with a walk-in closet, built-in quartz-topped storage, and spa-inspired bath with dual vanities and rainfall shower. Embrace effortless island living with ample bicycle and scooter parking and residential permit street parking for eligible residents. Fully furnished and turnkey, this low-maintenance retreat invites you to bring your toothbrush and explore Key West lifestyle from day one. Formerly configured as a duplex, the property also offers potential to restore two legal residences and create separate income streams, subject to verification and approvals. Schedule your private showing today to experience all this ideal property has to offer.

421 United St, Key West

$1,895,000

A former church with a practical second calling. At 905 Grinnell Street, four occupied residences carry monthly rents totaling $11,249. There is also off-street parking--a feature whose virtues need little explanation to anyone acquainted with Old Town. The building retains its distinctive character while accommodating a three-bedroom residence, two two-bedroom residences, and a studio, each with one bathroom. Separate entrances and outdoor spaces lend the apartments a measure of independence. Together, they comprise approximately 3,383 square feet on a 5,737-square-foot lot. Concrete-block construction, a metal roof, and a location in the X-500 flood zone supply the practical details. The surrounding Historic District supplies the rest: neighborhood restaurants, shops, and Duval Street within walking distance. Offered at $1,895,000, with tenants in place and an established rental history. Rental and operating statements are available for those who prefer to read beyond the photographs.

8 Beds ⋅ 4 Baths ⋅ 621807 MLS

A former church with a practical second calling. At 905 Grinnell Street, four occupied residences carry monthly rents totaling $11,249. There is also off-street parking--a feature whose virtues need little explanation to anyone acquainted with Old Town. The building retains its distinctive character while accommodating a three-bedroom residence, two two-bedroom residences, and a studio, each with one bathroom. Separate entrances and outdoor spaces lend the apartments a measure of independence. Together, they comprise approximately 3,383 square feet on a 5,737-square-foot lot. Concrete-block construction, a metal roof, and a location in the X-500 flood zone supply the practical details. The surrounding Historic District supplies the rest: neighborhood restaurants, shops, and Duval Street within walking distance. Offered at $1,895,000, with tenants in place and an established rental history. Rental and operating statements are available for those who prefer to read beyond the photographs.

905 Grinnell St, Key West

$1,895,000

Ideally located just two blocks from the beach, this beautifully renovated Key West residence blends island living, modern comfort, and plenty of space to make it your own. Set on an expansive 6,000-square-foot corner lot, the home offers more than 2,200 square feet of living space in one of Key West's most desirable residential neighborhoods. Walk to the beach and iconic White Street Pier, along with nearby pickleball courts, playgrounds, the weekly artisan market, Bayview Park, and Fausto's Food Palace. Local favorites including Salute! On The Beach and Louie's Backyard are also just minutes away. At the heart of the home is a brand-new kitchen featuring custom cabinetry, stainless steel appliances, quartz countertops, and a fresh, sophisticated finish. Thoughtful renovations throughout provide a beautifully updated foundation while leaving room for the next owners to add their own personal style. Major improvements include a new roof, impact-rated windows and doors, updated HVAC, lighting, interior and exterior paint, water heater, and other essential systems--offering peace of mind with many of the home's major components already addressed. The property also has no history of flooding, an especially valuable feature for island living. Outside, the oversized corner lot offers exceptional potential to create a private Key West retreat, with ample room for a pool, tropical landscaping, and outdoor entertaining areas. Ample street parking is available, along with off-street parking suitable for a small sedan or golf cart. With more than 2,200 square feet of living space, a substantial corner lot, extensive improvements, and an exceptional location just two blocks from the Atlantic, this Rose Street residence presents a rare opportunity to create your own piece of Key West paradise.

4 Beds ⋅ 4 Baths ⋅ 621516 MLS

Ideally located just two blocks from the beach, this beautifully renovated Key West residence blends island living, modern comfort, and plenty of space to make it your own. Set on an expansive 6,000-square-foot corner lot, the home offers more than 2,200 square feet of living space in one of Key West's most desirable residential neighborhoods. Walk to the beach and iconic White Street Pier, along with nearby pickleball courts, playgrounds, the weekly artisan market, Bayview Park, and Fausto's Food Palace. Local favorites including Salute! On The Beach and Louie's Backyard are also just minutes away. At the heart of the home is a brand-new kitchen featuring custom cabinetry, stainless steel appliances, quartz countertops, and a fresh, sophisticated finish. Thoughtful renovations throughout provide a beautifully updated foundation while leaving room for the next owners to add their own personal style. Major improvements include a new roof, impact-rated windows and doors, updated HVAC, lighting, interior and exterior paint, water heater, and other essential systems--offering peace of mind with many of the home's major components already addressed. The property also has no history of flooding, an especially valuable feature for island living. Outside, the oversized corner lot offers exceptional potential to create a private Key West retreat, with ample room for a pool, tropical landscaping, and outdoor entertaining areas. Ample street parking is available, along with off-street parking suitable for a small sedan or golf cart. With more than 2,200 square feet of living space, a substantial corner lot, extensive improvements, and an exceptional location just two blocks from the Atlantic, this Rose Street residence presents a rare opportunity to create your own piece of Key West paradise.

1423 Rose St, Key West

$1,895,000

Meticulously upgraded island retreat offering resort-style outdoor living on 3 lots spanning 22,500 sq ft, luxury finishes, and smart technology throughout. The backyard oasis features a resort-style pool with an integrated lap lane, custom-blend glass waterline tile, and premium glass bead aggregate finish. Enjoy the sun shelf, waterfall wall, four therapy jets, kept comfortable all year long by a heat pump with chiller. The 18x28 gazebo offers exposed beams, a T&G ceiling, matching metal roof, full summer kitchen, bar, dining/lounge area, and a wood-burning pizza oven. Nearly 6,000 sq ft of travertine pavers cover the driveway, pool deck, and patio, with matching new travertine stairs and over 4,000 sq ft of turf. The covered patio features a new screen enclosure, plus an 8x11 storage shed with matching metal roof. The fully fenced yard includes a walk gate and 10-ft double gate for boat storage. Over 1,500 sq ft of enclosed garage that can accommodate 6 cars and still room for storage and other toys. Inside and out, the home has just been freshly painted (including gutters and railings) with new porcelain wood-plank tile flowing throughout the interior, entry, and terrace. The updated pantry/laundry offers quartz counters and custom built-in shelving. The primary suite showcases a reclaimed wood feature wall, matching platform king bed frame, custom nightstands, and a spa bath with quartz counters and handcrafted glass tile mosaic. Custom walk-in closets serve the primary and guest suites; the third bedroom has a custom media/storage closet. Smart features include a 12-speaker Sonos Wi-Fi system, whole-home smart lighting/pool/climate control, Starlink Gen 4 with wired routers, Ring camera monitoring, automated landscape lighting, and new AC (2026). This is more than a home, it's a fully reimagined island lifestyle.

3 Beds ⋅ 2 Baths ⋅ 620892 MLS

Meticulously upgraded island retreat offering resort-style outdoor living on 3 lots spanning 22,500 sq ft, luxury finishes, and smart technology throughout. The backyard oasis features a resort-style pool with an integrated lap lane, custom-blend glass waterline tile, and premium glass bead aggregate finish. Enjoy the sun shelf, waterfall wall, four therapy jets, kept comfortable all year long by a heat pump with chiller. The 18x28 gazebo offers exposed beams, a T&G ceiling, matching metal roof, full summer kitchen, bar, dining/lounge area, and a wood-burning pizza oven. Nearly 6,000 sq ft of travertine pavers cover the driveway, pool deck, and patio, with matching new travertine stairs and over 4,000 sq ft of turf. The covered patio features a new screen enclosure, plus an 8x11 storage shed with matching metal roof. The fully fenced yard includes a walk gate and 10-ft double gate for boat storage. Over 1,500 sq ft of enclosed garage that can accommodate 6 cars and still room for storage and other toys. Inside and out, the home has just been freshly painted (including gutters and railings) with new porcelain wood-plank tile flowing throughout the interior, entry, and terrace. The updated pantry/laundry offers quartz counters and custom built-in shelving. The primary suite showcases a reclaimed wood feature wall, matching platform king bed frame, custom nightstands, and a spa bath with quartz counters and handcrafted glass tile mosaic. Custom walk-in closets serve the primary and guest suites; the third bedroom has a custom media/storage closet. Smart features include a 12-speaker Sonos Wi-Fi system, whole-home smart lighting/pool/climate control, Starlink Gen 4 with wired routers, Ring camera monitoring, automated landscape lighting, and new AC (2026). This is more than a home, it's a fully reimagined island lifestyle.

122 S Bahama Dr, Duck Key

$1,895,000

Welcome to Ocean Harbour, one of Islamorada's premier communities! This unique 4 Bedroom, 3 Bathroom expansive 2668sqft condominium offers a desirable split floor plan with an open kitchen, dining room and living area, impact windows and doors, new a/c and water heater along with an enclosed air-conditioned porch, all overlooking breathtaking views of the Atlantic Ocean. Enjoy the convenience of a private rear entry staircase leading directly to your 50' boat slip (#27), nestled in the expansive marina. Additional perks include storage room and covered parking. Set on 12 acres of lush tropical grounds, Ocean Harbour offers endless amenities including a heated swimming pool, hot tub, sandy beach, boat ramp, trailer storage, tennis and pickleball courts, clubhouse, and a fitness center with ocean views. Enjoy nearby Florida Bay access through Snake Creek offering offshore or backcountry fishing and numerous delicious waterfront restaurants. This property truly offers the best of Keys living!

4 Beds ⋅ 3 Baths ⋅ 620649 MLS

Welcome to Ocean Harbour, one of Islamorada's premier communities! This unique 4 Bedroom, 3 Bathroom expansive 2668sqft condominium offers a desirable split floor plan with an open kitchen, dining room and living area, impact windows and doors, new a/c and water heater along with an enclosed air-conditioned porch, all overlooking breathtaking views of the Atlantic Ocean. Enjoy the convenience of a private rear entry staircase leading directly to your 50' boat slip (#27), nestled in the expansive marina. Additional perks include storage room and covered parking. Set on 12 acres of lush tropical grounds, Ocean Harbour offers endless amenities including a heated swimming pool, hot tub, sandy beach, boat ramp, trailer storage, tennis and pickleball courts, clubhouse, and a fitness center with ocean views. Enjoy nearby Florida Bay access through Snake Creek offering offshore or backcountry fishing and numerous delicious waterfront restaurants. This property truly offers the best of Keys living!

87851 Old Hwy Unit P3, Islamorada

$1,890,000

Nestled in the heart of Old Town Key West, this historic gem boasts an impeccable blend of classic architecture and modern amenities. With a rich history dating back to the late1800's, this captivating residence offers the perfect opportunity to own a piece of Key West's storied past. Awarded the Gold Star for Historic Preservations, 516 Elizabeth St. is the perfect example of a Classical Revival Eyebrow House - a style unique to Key West. The roof overhangs over the second floor windows onto classic porch columns giving the suggested appearance of 'eyebrows' providing protection from rain and sun allowing the inside to have fresh air even during the hot summer months. Upon entering the home, original Dade County pine walls, high 10ft ceilings, original double hung wooden windows exude the timeless elegance of a bygone era. While preserving its historic character, this home has been thoughtfully updated with modern amenities. The kitchen features custom wooden cabinets and stainless steel appliances and all bathrooms are beautifully renovated. Enjoy the convenience of contemporary living without compromising on the historic appeal. The primary bedroom and bathroom upstairs provide a tranquil retreat, and the guest bedroom downstairs with it's own bathroom is convenient and comfortable. French doors lead from the formal dining room and kitchen to a sundeck with a covered dining area and extra lounging space to entertain. A Pool with water feature and new decking was just added to the property. This home has a rich history, with tales of past occupants, the Pinder family, and the unique stories of its heritage adding an extra layer of prestige and historical significance to its charm. This historic home is a rare find in a prime location, offering the best of both worlds. The house has some monthly vacation rental history and is sold furnished (some personal pieces & all art work excluded)!

2 Beds ⋅ 3 Baths ⋅ 621199 MLS

Nestled in the heart of Old Town Key West, this historic gem boasts an impeccable blend of classic architecture and modern amenities. With a rich history dating back to the late1800's, this captivating residence offers the perfect opportunity to own a piece of Key West's storied past. Awarded the Gold Star for Historic Preservations, 516 Elizabeth St. is the perfect example of a Classical Revival Eyebrow House - a style unique to Key West. The roof overhangs over the second floor windows onto classic porch columns giving the suggested appearance of 'eyebrows' providing protection from rain and sun allowing the inside to have fresh air even during the hot summer months. Upon entering the home, original Dade County pine walls, high 10ft ceilings, original double hung wooden windows exude the timeless elegance of a bygone era. While preserving its historic character, this home has been thoughtfully updated with modern amenities. The kitchen features custom wooden cabinets and stainless steel appliances and all bathrooms are beautifully renovated. Enjoy the convenience of contemporary living without compromising on the historic appeal. The primary bedroom and bathroom upstairs provide a tranquil retreat, and the guest bedroom downstairs with it's own bathroom is convenient and comfortable. French doors lead from the formal dining room and kitchen to a sundeck with a covered dining area and extra lounging space to entertain. A Pool with water feature and new decking was just added to the property. This home has a rich history, with tales of past occupants, the Pinder family, and the unique stories of its heritage adding an extra layer of prestige and historical significance to its charm. This historic home is a rare find in a prime location, offering the best of both worlds. The house has some monthly vacation rental history and is sold furnished (some personal pieces & all art work excluded)!

516 Elizabeth St, Key West

74980 Overseas Highway Unit 3, Islamorada

$1,890,000

Experience the ultimate Florida Keys lifestyle in this stunning split-level waterfront loft and take advantage of the vacation rental revenue. Ideally located in highly sought-after Lower Matecumbe. This exceptional 5-bedroom, 3-bath residence combines contemporary design with breathtaking water views, creating a truly unique island retreat. The thoughtfully designed layout features three spacious bedrooms on the lower level and two additional bedrooms upstairs, connected by a spectacular modern staircase that serves as a striking architectural centerpiece. Soaring ceilings and expansive windows fill the home with natural light, while the open-concept floor plan seamlessly connects the living, dining, and entertaining spaces. The sleek, modern kitchen is perfectly positioned to serve both everyday living and waterfront gatherings. Generously sized bedrooms and beautifully appointed bathrooms provide comfort and privacy for family and guests alike. Step outside to an impressive 667-square-foot waterfront screened deck overlooking the tranquil lagoon, offering the perfect setting for outdoor dining, entertaining, or simply enjoying the peaceful surroundings. Boaters will appreciate the deep-water dockage featuring a large boat slip and 16k boat lift, with convenient access to both the Atlantic Ocean and Florida Bay. Enjoy stunning views of the bayside lagoon and the ocean, along with world-class fishing, diving, and boating right from your backyard. Additional amenities include covered parking and ample storage space for all your water toys. Offering the perfect blend of modern elegance, waterfront living, and premier boating access, this remarkable Lower Matecumbe property is a rare opportunity to own a piece of paradise in one of Islamorada's most desirable locations. Onsite property management for true peace of mind.

5 Beds ⋅ 3 Baths ⋅ 620271 MLS

Experience the ultimate Florida Keys lifestyle in this stunning split-level waterfront loft and take advantage of the vacation rental revenue. Ideally located in highly sought-after Lower Matecumbe. This exceptional 5-bedroom, 3-bath residence combines contemporary design with breathtaking water views, creating a truly unique island retreat. The thoughtfully designed layout features three spacious bedrooms on the lower level and two additional bedrooms upstairs, connected by a spectacular modern staircase that serves as a striking architectural centerpiece. Soaring ceilings and expansive windows fill the home with natural light, while the open-concept floor plan seamlessly connects the living, dining, and entertaining spaces. The sleek, modern kitchen is perfectly positioned to serve both everyday living and waterfront gatherings. Generously sized bedrooms and beautifully appointed bathrooms provide comfort and privacy for family and guests alike. Step outside to an impressive 667-square-foot waterfront screened deck overlooking the tranquil lagoon, offering the perfect setting for outdoor dining, entertaining, or simply enjoying the peaceful surroundings. Boaters will appreciate the deep-water dockage featuring a large boat slip and 16k boat lift, with convenient access to both the Atlantic Ocean and Florida Bay. Enjoy stunning views of the bayside lagoon and the ocean, along with world-class fishing, diving, and boating right from your backyard. Additional amenities include covered parking and ample storage space for all your water toys. Offering the perfect blend of modern elegance, waterfront living, and premier boating access, this remarkable Lower Matecumbe property is a rare opportunity to own a piece of paradise in one of Islamorada's most desirable locations. Onsite property management for true peace of mind.

74980 Overseas Highway Unit 3, Islamorada

$1,885,000

Open water, glowing sunsets, and your own sandy shoreline--this updated waterfront home captures the spirit of Florida Keys living! Situated on a corner lot with 180 feet of waterfront, this 3-bedroom, 2-bath concrete block home pairs inviting interiors with outdoor spaces made for enjoying life on the water. Updated with impact windows and sliding glass doors. Relax on the screened deck, watch for passing dolphins, and enjoy happy hour as the sunset paints the sky. Take a refreshing dip in the heated fiberglass pool or unwind along your sandy beach with the waterfront as your backdrop. Boating amenities include a 100-foot concrete dock with 11,000-pound davits, while concrete steps into the canal provide convenient water access. Launch a kayak from the beach, cast a line from the dock, or head out to explore the surrounding waters. An outdoor shower, downstairs storage, and a concrete RV/boat parking pad everyday convenience. Areca palms line the side property for tropical privacy, complemented by a concrete wall and custom aluminum gate. From poolside afternoons to sunset evenings by the water, this home is ready for your next chapter in the Keys.

3 Beds ⋅ 2 Baths ⋅ 621866 MLS

Open water, glowing sunsets, and your own sandy shoreline--this updated waterfront home captures the spirit of Florida Keys living! Situated on a corner lot with 180 feet of waterfront, this 3-bedroom, 2-bath concrete block home pairs inviting interiors with outdoor spaces made for enjoying life on the water. Updated with impact windows and sliding glass doors. Relax on the screened deck, watch for passing dolphins, and enjoy happy hour as the sunset paints the sky. Take a refreshing dip in the heated fiberglass pool or unwind along your sandy beach with the waterfront as your backdrop. Boating amenities include a 100-foot concrete dock with 11,000-pound davits, while concrete steps into the canal provide convenient water access. Launch a kayak from the beach, cast a line from the dock, or head out to explore the surrounding waters. An outdoor shower, downstairs storage, and a concrete RV/boat parking pad everyday convenience. Areca palms line the side property for tropical privacy, complemented by a concrete wall and custom aluminum gate. From poolside afternoons to sunset evenings by the water, this home is ready for your next chapter in the Keys.

22939 Sharp Ln, Cudjoe

$1,875,000

Rare canal-front duplex on Duck Key's prestigious Indies Canal with 70 feet of new composite dockage, sweeping canal views, and deep-water access to both the Gulf and Atlantic. New roof, new AC, and precast concrete construction throughout -- this is a solid, storm-ready build with significant insurance advantages over at-grade alternatives and no deferred maintenance surprises. Two self-contained side-by-side units, each 2BD/2BA with in-unit washer/dryer, private canal-view balcony, open floor plan, and under-house storage. Unit 1 is fully renovated -- granite counters, stainless appliances, new Kitchenaide soft close cabinetry, updated baths, tile floors throughout. Unit 2 features upgraded tile floors and a bright open canvas with kitchen and baths ready for your finish. The options here are unusually flexible: rent both units for strong 28-day vacation rental income, live in one and let the other pay your carry, or convert the entire structure to a single-family waterfront compound -- there's even room for a pool. That kind of optionality, in a precast concrete above-flood building with a new roof and new dock, simply does not exist elsewhere on Duck Key. Monroe County 28-day minimum rental applies. Sold as a complete duplex; cannot be split.

4 Beds ⋅ 4 Baths ⋅ 620609 MLS

Rare canal-front duplex on Duck Key's prestigious Indies Canal with 70 feet of new composite dockage, sweeping canal views, and deep-water access to both the Gulf and Atlantic. New roof, new AC, and precast concrete construction throughout -- this is a solid, storm-ready build with significant insurance advantages over at-grade alternatives and no deferred maintenance surprises. Two self-contained side-by-side units, each 2BD/2BA with in-unit washer/dryer, private canal-view balcony, open floor plan, and under-house storage. Unit 1 is fully renovated -- granite counters, stainless appliances, new Kitchenaide soft close cabinetry, updated baths, tile floors throughout. Unit 2 features upgraded tile floors and a bright open canvas with kitchen and baths ready for your finish. The options here are unusually flexible: rent both units for strong 28-day vacation rental income, live in one and let the other pay your carry, or convert the entire structure to a single-family waterfront compound -- there's even room for a pool. That kind of optionality, in a precast concrete above-flood building with a new roof and new dock, simply does not exist elsewhere on Duck Key. Monroe County 28-day minimum rental applies. Sold as a complete duplex; cannot be split.

126 N Indies Dr, Duck Key

$1,875,000

Spacious and sophisticated waterfront home situated on a wide canal with desirable eastern exposure, offering serene views of the in-ground pool and 100-foot-wide canal. Designed for both entertaining and everyday comfort, the home features a covered patio on the lower level and a generous wooden deck on the upper level, connected by elegant spiral stairs leading to a dedicated entertainment area below. The newly updated upstairs kitchen is bright, modern, and exceptionally spacious, anchoring the upper-level living space. This five-bedroom, three-bathroom residence is thoughtfully laid out with two bedrooms and two bathrooms upstairs, and three bedrooms with one bathroom downstairs--ideal for extended family, guests, or rental flexibility. A circular paver driveway provides ample parking, while separate living areas on each floor enhance privacy and functionality. The Corian kitchen, expansive layout, and waterfront lifestyle make this property suitable as a large family home, corporate retreat, or high-performing vacation rental. Complete with a private boat lift and quick access to the Atlantic Ocean, this home delivers the full waterfront experience--whether as a permanent residence or an income-generating investment.

5 Beds ⋅ 3 Baths ⋅ 618755 MLS

Spacious and sophisticated waterfront home situated on a wide canal with desirable eastern exposure, offering serene views of the in-ground pool and 100-foot-wide canal. Designed for both entertaining and everyday comfort, the home features a covered patio on the lower level and a generous wooden deck on the upper level, connected by elegant spiral stairs leading to a dedicated entertainment area below. The newly updated upstairs kitchen is bright, modern, and exceptionally spacious, anchoring the upper-level living space. This five-bedroom, three-bathroom residence is thoughtfully laid out with two bedrooms and two bathrooms upstairs, and three bedrooms with one bathroom downstairs--ideal for extended family, guests, or rental flexibility. A circular paver driveway provides ample parking, while separate living areas on each floor enhance privacy and functionality. The Corian kitchen, expansive layout, and waterfront lifestyle make this property suitable as a large family home, corporate retreat, or high-performing vacation rental. Complete with a private boat lift and quick access to the Atlantic Ocean, this home delivers the full waterfront experience--whether as a permanent residence or an income-generating investment.

320 5th St, Key Colony

$1,850,000

A rare and compelling corner residence in the heart of historic Old Town, 530 White Street offers the distinctive character and generous proportions rarely found in this most coveted of Key West neighborhoods. Originally built in the late 1800's, in classic Conch style, the home sits on a spacious 7,400 square-foot lot at the intersection of White Street and Stump Lane, providing both presence and privacy within easy reach of the island's most storied streets. The two-story frame residence, with approximately 2,146 square feet, is currently arranged as three private residences. Two downstairs and one above, creating an ideal configuration for multi-generational living, guest accommodations, or income potential. Downstairs, the first suite features the warmth of original Dade County pine walls and wood floors, while the second opens to the garden with cathedral ceilings and a private deck. Above, a bright one-bedroom residence enjoys a generous private deck, expansive living and dining spaces, and access to a loft. Wraparound porches, a metal roof, and mature landscaping lend the property the quiet grace of Key West's architectural heritage. A workshop, off-street parking, and abundant outdoor space offer further opportunities, including the potential for a pool or refined garden retreat. Zoned within the historic district, 530 White Street presents an exceptional canvas for those seeking to restore, reimagine, or simply enjoy a true Old Town home of substance and scale. This is an uncommon opportunity to acquire a large-lot historic residence in one of America's most romantic and enduring island communities.

5 Beds ⋅ 3 Baths ⋅ 622062 MLS

A rare and compelling corner residence in the heart of historic Old Town, 530 White Street offers the distinctive character and generous proportions rarely found in this most coveted of Key West neighborhoods. Originally built in the late 1800's, in classic Conch style, the home sits on a spacious 7,400 square-foot lot at the intersection of White Street and Stump Lane, providing both presence and privacy within easy reach of the island's most storied streets. The two-story frame residence, with approximately 2,146 square feet, is currently arranged as three private residences. Two downstairs and one above, creating an ideal configuration for multi-generational living, guest accommodations, or income potential. Downstairs, the first suite features the warmth of original Dade County pine walls and wood floors, while the second opens to the garden with cathedral ceilings and a private deck. Above, a bright one-bedroom residence enjoys a generous private deck, expansive living and dining spaces, and access to a loft. Wraparound porches, a metal roof, and mature landscaping lend the property the quiet grace of Key West's architectural heritage. A workshop, off-street parking, and abundant outdoor space offer further opportunities, including the potential for a pool or refined garden retreat. Zoned within the historic district, 530 White Street presents an exceptional canvas for those seeking to restore, reimagine, or simply enjoy a true Old Town home of substance and scale. This is an uncommon opportunity to acquire a large-lot historic residence in one of America's most romantic and enduring island communities.

530 White St, Key West

$1,850,000

Experience the ultimate Florida Keys lifestyle in this spacious Islamorada canal front home featuring 70 feet of dockage and a 10,000 lb boat lift! The home offers 3 beds/ 2 baths laid out with 2 bedrooms and 1 bathroom upstairs, plus 1 bedroom and 1 bathroom downstairs, with a bonus convenient laundry / storage area not counted in the Sqft. Relax and Enjoy a large, open porch overlooking the canal under a solid concrete roof, perfect for relaxing and taking in the coastal breezes. Impact-resistant windows and doors throughout provide added peace of mind. Outdoor living is at its finest with a tiki hut, fire pit, jacuzzi, golf course, and even an ice maker to keep your coolers stocked for those perfect boating days! Ample parking provides plenty of room for multiple vehicles and boat trailers. Ideally situated in a friendly oceanside neighborhood near Tavernier Creek, you'll enjoy quick boating access to the bayside in just minutes. Fantastic restaurants, shopping, and everything that makes Islamorada special are right around the corner! This canal front home offers the perfect combination of comfort, convenience, fun and the laid-back Florida Keys lifestyle!

3 Beds ⋅ 2 Baths ⋅ 622027 MLS

Experience the ultimate Florida Keys lifestyle in this spacious Islamorada canal front home featuring 70 feet of dockage and a 10,000 lb boat lift! The home offers 3 beds/ 2 baths laid out with 2 bedrooms and 1 bathroom upstairs, plus 1 bedroom and 1 bathroom downstairs, with a bonus convenient laundry / storage area not counted in the Sqft. Relax and Enjoy a large, open porch overlooking the canal under a solid concrete roof, perfect for relaxing and taking in the coastal breezes. Impact-resistant windows and doors throughout provide added peace of mind. Outdoor living is at its finest with a tiki hut, fire pit, jacuzzi, golf course, and even an ice maker to keep your coolers stocked for those perfect boating days! Ample parking provides plenty of room for multiple vehicles and boat trailers. Ideally situated in a friendly oceanside neighborhood near Tavernier Creek, you'll enjoy quick boating access to the bayside in just minutes. Fantastic restaurants, shopping, and everything that makes Islamorada special are right around the corner! This canal front home offers the perfect combination of comfort, convenience, fun and the laid-back Florida Keys lifestyle!

142 Harbor Dr, Islamorada

$1,850,000

This Commercial Residential mixed use building offers an excellent investment or owner operator opportunity. A prime location 513 Truman has excellent visibility with heavy foot and vehicular traffic. Downstairs is a large commercial space currently vacant. It could easily accommodate numerous commercial tenants. Upstairs are two apartments including a one bedroom one bath and a large studio. Both residential units have modern finishes including full kitchen, granite counters, stainless appliances, ample closet space and a shared laundry room. Each unit features a private balcony. The original building was renovated and a large two story addition was built in 2010 which included the two apartments and an addition to the commercial space. There is parking for 2/3 cars tandem style on the side of the building. This versatile property is a rare find, located in a transient receiver zone.

2 Beds ⋅ 6 Baths ⋅ 621449 MLS

This Commercial Residential mixed use building offers an excellent investment or owner operator opportunity. A prime location 513 Truman has excellent visibility with heavy foot and vehicular traffic. Downstairs is a large commercial space currently vacant. It could easily accommodate numerous commercial tenants. Upstairs are two apartments including a one bedroom one bath and a large studio. Both residential units have modern finishes including full kitchen, granite counters, stainless appliances, ample closet space and a shared laundry room. Each unit features a private balcony. The original building was renovated and a large two story addition was built in 2010 which included the two apartments and an addition to the commercial space. There is parking for 2/3 cars tandem style on the side of the building. This versatile property is a rare find, located in a transient receiver zone.

513 Truman Ave, Key West

$1,850,000

Set along a peaceful canal on Cudjoe Key, this 2016 residence pairs solid CBS construction with an unmistakably elevated sense of island living. This 4 bedroom, 3.5 bath home features impact windows and doors and a standing seam metal roof, speaking to a level of craftsmanship built to endure, while 2,548 square feet of living space and roughly 1,370 square feet of balconies invite the surrounding water views and tropical air into everyday life. The main level is designed for both privacy and gathering, offering 3 guest bedrooms, 2 full baths and a laundry room alongside a second living area that opens onto a spacious covered balcony. One bedroom enjoys its own ensuite, while the remaining two share a well-appointed Jack and Jill bath. Ascend to the main living level and the home opens into a bright and airy Great room where kitchen, dining and living areas unfold together. Anchored by a substantial island and dining bar, the kitchen is finished with Silestone countertops, a sea glass tile backsplash and abundant custom cabinetry. Beyond, another expansive balcony extends the living space into the open air, ideal for evening entertaining or a quiet morning coffee. The primary suite occupies its own private wing upstairs, offering generous closets and a spa inspired ensuite with a jetted tub and separate walk-in shower. Outside, a heated and chilled concrete pool sets the stage for effortless indoor-outdoor living, while a 30-foot concrete dock with lighting and bubblers provides canal access for boating, paddling or an evening line in the water, with the open water just minutes beyond. Located just minutes from local restaurants, shopping and coffee shops, this a rare balance of quality, privacy and island sophistication, backed by a proven rental history that makes it as compelling an investment as it is a home.

4 Beds ⋅ 4 Baths ⋅ 621161 MLS

Set along a peaceful canal on Cudjoe Key, this 2016 residence pairs solid CBS construction with an unmistakably elevated sense of island living. This 4 bedroom, 3.5 bath home features impact windows and doors and a standing seam metal roof, speaking to a level of craftsmanship built to endure, while 2,548 square feet of living space and roughly 1,370 square feet of balconies invite the surrounding water views and tropical air into everyday life. The main level is designed for both privacy and gathering, offering 3 guest bedrooms, 2 full baths and a laundry room alongside a second living area that opens onto a spacious covered balcony. One bedroom enjoys its own ensuite, while the remaining two share a well-appointed Jack and Jill bath. Ascend to the main living level and the home opens into a bright and airy Great room where kitchen, dining and living areas unfold together. Anchored by a substantial island and dining bar, the kitchen is finished with Silestone countertops, a sea glass tile backsplash and abundant custom cabinetry. Beyond, another expansive balcony extends the living space into the open air, ideal for evening entertaining or a quiet morning coffee. The primary suite occupies its own private wing upstairs, offering generous closets and a spa inspired ensuite with a jetted tub and separate walk-in shower. Outside, a heated and chilled concrete pool sets the stage for effortless indoor-outdoor living, while a 30-foot concrete dock with lighting and bubblers provides canal access for boating, paddling or an evening line in the water, with the open water just minutes beyond. Located just minutes from local restaurants, shopping and coffee shops, this a rare balance of quality, privacy and island sophistication, backed by a proven rental history that makes it as compelling an investment as it is a home.

1106 Thatch Ln, Cudjoe

$1,850,000

Have your cake and eat it too! 60+ feet of Protected Seawall with boatlift, PLUS a gorgeous open water Gulf View. Elevated home with three bedrooms and two baths opens on to a wonderful deck to enjoy the sun. You can also get shade while enjoying the Gulf breezes in the screened patio off the Kitchen. As we head downstairs you can lounge around the pool and enjoy the views of the Gulf of Mexico. the boatlift is conveniently located so as not to block the view. Plenty of living space under the home, with room for boat trailers in the front. But wait, there's more; 338 square feet of permitted garage for storage. The perfect home for your and your family, or as a vacation rental.

3 Beds ⋅ 2 Baths ⋅ 620576 MLS

Have your cake and eat it too! 60+ feet of Protected Seawall with boatlift, PLUS a gorgeous open water Gulf View. Elevated home with three bedrooms and two baths opens on to a wonderful deck to enjoy the sun. You can also get shade while enjoying the Gulf breezes in the screened patio off the Kitchen. As we head downstairs you can lounge around the pool and enjoy the views of the Gulf of Mexico. the boatlift is conveniently located so as not to block the view. Plenty of living space under the home, with room for boat trailers in the front. But wait, there's more; 338 square feet of permitted garage for storage. The perfect home for your and your family, or as a vacation rental.

106 Alynn Pl, Marathon

$1,850,000

DIRECT OCEANFRONT lot with 120 feet of concrete seawall. Total of 153 feet of ocean frontage with cut in boat slip. Building right in place. NO TBR or BPAS (ROGO) needed to start building (this saves you time and money). End of street right-a-way deed conveys with the property. Huge lot: oceanfront concrete dock 120' plus additional 33' of oceanfront for the end of street right-a-way - Street 75' - Side: 133' - Back: 125.' Cleared and ready to build now. Lot is graveled, silver buttonwood hedge, partially fenced. You can see Key Colony to the East and Sombrero to the west with unobstructed ocean views. Glorious sunrise and sunsets! Listing agent is the owner. Call me directly with any questions.

620537 MLS

DIRECT OCEANFRONT lot with 120 feet of concrete seawall. Total of 153 feet of ocean frontage with cut in boat slip. Building right in place. NO TBR or BPAS (ROGO) needed to start building (this saves you time and money). End of street right-a-way deed conveys with the property. Huge lot: oceanfront concrete dock 120' plus additional 33' of oceanfront for the end of street right-a-way - Street 75' - Side: 133' - Back: 125.' Cleared and ready to build now. Lot is graveled, silver buttonwood hedge, partially fenced. You can see Key Colony to the East and Sombrero to the west with unobstructed ocean views. Glorious sunrise and sunsets! Listing agent is the owner. Call me directly with any questions.

1235 83rd Street Ocean St, Marathon

$1,850,000

701 Simonton Street offers a standout commercial presence in the heart of Old Town Key West, positioned on the highly visible corner of Simonton and Angela Streets. This single-story commercial building features 1,745 square feet of functional interior space on a 6,510 square foot lot, with 8+ off-street parking spaces and a convenient drive-through parking layout. The existing floor plan includes five private offices, a reception/lobby area, storage, central air conditioning, and a security system, creating flexibility for many uses. Frame construction, a metal roof, and an X flood zone location add practical appeal for an owner-user or investor. Located in the Historic Neighborhood Commercial (HNC-1) zoning district, this corner property offers strong visibility, convenient access, and rare on-site parking in one of Key West's most established and walkable Old Town locations. Located in the Transient rental License Transfer receivership zone as shown in the map attached.

3 Baths ⋅ 620342 MLS

701 Simonton Street offers a standout commercial presence in the heart of Old Town Key West, positioned on the highly visible corner of Simonton and Angela Streets. This single-story commercial building features 1,745 square feet of functional interior space on a 6,510 square foot lot, with 8+ off-street parking spaces and a convenient drive-through parking layout. The existing floor plan includes five private offices, a reception/lobby area, storage, central air conditioning, and a security system, creating flexibility for many uses. Frame construction, a metal roof, and an X flood zone location add practical appeal for an owner-user or investor. Located in the Historic Neighborhood Commercial (HNC-1) zoning district, this corner property offers strong visibility, convenient access, and rare on-site parking in one of Key West's most established and walkable Old Town locations. Located in the Transient rental License Transfer receivership zone as shown in the map attached.

701 Simonton St, Key West

$1,850,000

Open water pool home with breathtaking views of Bogie Channel and direct deep water access to both the Atlantic Ocean and the Gulf. Located on a spacious 13,275 sq ft lot, this solid concrete ground-level residence is a true boater's paradise featuring a 75-foot concrete dock and a protected boat basin. Inside, the 1,980 sq ft home offers a large great room, a Florida Room perfect for sunrise coffee, and a spacious kitchen with quartz countertops and a center island ideal for entertaining. Enjoy the seamless indoor-outdoor lifestyle with a waterfront pool surrounded by tropical landscaping, swaying palms, and a peaceful outdoor patio. The primary suite offers views of the pool and water, blending luxury and tranquility. Built to last with impact-resistant doors and windows and a durable metal roof. Additional features include a one-car garage, beautifully manicured grounds, and regular visits from native birds and Key Deer. Ride your bike across the bridge to No Name Key or walk to the world-famous No Name Pub. Just minutes to shopping, dining, and all the Lower Keys have to offer.

2 Beds ⋅ 2 Baths ⋅ 617440 MLS

Open water pool home with breathtaking views of Bogie Channel and direct deep water access to both the Atlantic Ocean and the Gulf. Located on a spacious 13,275 sq ft lot, this solid concrete ground-level residence is a true boater's paradise featuring a 75-foot concrete dock and a protected boat basin. Inside, the 1,980 sq ft home offers a large great room, a Florida Room perfect for sunrise coffee, and a spacious kitchen with quartz countertops and a center island ideal for entertaining. Enjoy the seamless indoor-outdoor lifestyle with a waterfront pool surrounded by tropical landscaping, swaying palms, and a peaceful outdoor patio. The primary suite offers views of the pool and water, blending luxury and tranquility. Built to last with impact-resistant doors and windows and a durable metal roof. Additional features include a one-car garage, beautifully manicured grounds, and regular visits from native birds and Key Deer. Ride your bike across the bridge to No Name Key or walk to the world-famous No Name Pub. Just minutes to shopping, dining, and all the Lower Keys have to offer.

1607 Sunrise Dr, Big Pine

$1,849,000

Beautiful Double Waterfront Lot in Prestigious Plantation Key Colony. This stunning 4-bedroom, 2-bath waterfront home sits on a Rare Double Lot with a Private Boat Ramp & Boat lift, . Step outside to your Private Oasis complete with a Private Tiki hut - Gorgeous secluded in-ground Pool and Cabana Hut Bungalow - The open-concept kitchen features Granite countertops and stainless steel appliances, ideal for effortless entertaining--Perfect for Boaters and outdoor enthusiasts. Tucked away in a quiet neighborhood, yet just minutes from restaurants, shopping, and top-rated schools, this home truly offers the best of island living. Seller will consider all reasonable offers.

4 Beds ⋅ 2 Baths ⋅ 617994 MLS

Beautiful Double Waterfront Lot in Prestigious Plantation Key Colony. This stunning 4-bedroom, 2-bath waterfront home sits on a Rare Double Lot with a Private Boat Ramp & Boat lift, . Step outside to your Private Oasis complete with a Private Tiki hut - Gorgeous secluded in-ground Pool and Cabana Hut Bungalow - The open-concept kitchen features Granite countertops and stainless steel appliances, ideal for effortless entertaining--Perfect for Boaters and outdoor enthusiasts. Tucked away in a quiet neighborhood, yet just minutes from restaurants, shopping, and top-rated schools, this home truly offers the best of island living. Seller will consider all reasonable offers.

150 Azalea St, Tavernier

$1,825,000

IMMACULATE OCEANSIDE WATERFRONT IN TAVERNIER, FLORIDA KEYS: Pristine, meticulously maintained 3-bedrm, 3-bath home, on deep-water canal w/open ocean access in approx. 5 minutes or less. This 2658 SqFt, Home-features a private 40-foot dock, 10,000-lb boat lift, w/approx. 60-foot-wide canal. This coastal elegance defines this two-story concrete residence, featuring solid CBS construction, a concrete roof, impact-resistant windows and doors, soaring ceilings, crown molding, w/ Plantation Shutters. The open-concept living & dining areas flow into a kitchen w/ custom wood cabinetry, granite countertops, and stainless steel appliances. A spacious downstairs den, w/Bathrm & additional living area provide versatility for guests, entertaining, or a potential '4th bedroom'. The ultimate indoor-outdoor lifestyle w/covered waterfront balconies on both levels, an outdoor kitchen, fish-cleaning station, w/lush tropical professional landscaping enhanced by elegant exterior lighting. Additional features include aluminum stairways, covered parking, a paved driveway, irrigation system, climate-controlled storage, and a 10,000-watt generator with GenerLink connection, see pictures! Located near the renowned Islamorada Sandbar, world-class fishing, diving, waterfront dining, Mariner's Hospital 1.5 miles, CVS, New Publix, Banks, Gym, Ace Hardware & More. OK to Lease for 28 day Minimum. Anchor In Paradise!

3 Beds ⋅ 3 Baths ⋅ 621574 MLS

IMMACULATE OCEANSIDE WATERFRONT IN TAVERNIER, FLORIDA KEYS: Pristine, meticulously maintained 3-bedrm, 3-bath home, on deep-water canal w/open ocean access in approx. 5 minutes or less. This 2658 SqFt, Home-features a private 40-foot dock, 10,000-lb boat lift, w/approx. 60-foot-wide canal. This coastal elegance defines this two-story concrete residence, featuring solid CBS construction, a concrete roof, impact-resistant windows and doors, soaring ceilings, crown molding, w/ Plantation Shutters. The open-concept living & dining areas flow into a kitchen w/ custom wood cabinetry, granite countertops, and stainless steel appliances. A spacious downstairs den, w/Bathrm & additional living area provide versatility for guests, entertaining, or a potential '4th bedroom'. The ultimate indoor-outdoor lifestyle w/covered waterfront balconies on both levels, an outdoor kitchen, fish-cleaning station, w/lush tropical professional landscaping enhanced by elegant exterior lighting. Additional features include aluminum stairways, covered parking, a paved driveway, irrigation system, climate-controlled storage, and a 10,000-watt generator with GenerLink connection, see pictures! Located near the renowned Islamorada Sandbar, world-class fishing, diving, waterfront dining, Mariner's Hospital 1.5 miles, CVS, New Publix, Banks, Gym, Ace Hardware & More. OK to Lease for 28 day Minimum. Anchor In Paradise!

226 Normandy Dr, Tavernier

$1,825,000

RARE OPPORTUNITY TO PURCHASE IN CASA MARINA FOR ONLY $835 PRICE PER SQUARE FOOT. (34% BELOW market value) Life feels a little different in Casa Marina. The streets are quieter, the homes are beautifully maintained, and everything from the beach to Old Town is just a short walk or bike ride away. Tucked within one of Key West's most desirable neighborhoods, 1115 South Street captures everything people love about living here. Step inside and the home immediately feels open and inviting. Ten foot ceilings, warm Brazilian cherry floors, and an abundance of natural light create spaces that feel both elegant and comfortable. The entire first floor is designed for gathering, anchored by an impressive kitchen with abundant cabinetry, expansive countertops, and high end appliances that make cooking and entertaining equally enjoyable. As beautiful as the interior is, your attention naturally shifts outdoors. French doors open to a private tropical backyard where a large swimming pool, separate hot tub, and coral stone patios with IPE decking create a peaceful setting for relaxing or entertaining. Surrounded by mature landscaping, the backyard feels like your own private retreat. With both bedrooms located upstairs, the home offers a thoughtful separation between everyday living and personal space. The primary suite even enjoys its own balcony overlooking the backyard, providing a quiet place to begin or end the day. Beautifully maintained and thoughtfully designed, this is a home where every detail encourages you to slow down, entertain often, and enjoy the best of Key West living.

2 Beds ⋅ 2 Baths ⋅ 620470 MLS

RARE OPPORTUNITY TO PURCHASE IN CASA MARINA FOR ONLY $835 PRICE PER SQUARE FOOT. (34% BELOW market value) Life feels a little different in Casa Marina. The streets are quieter, the homes are beautifully maintained, and everything from the beach to Old Town is just a short walk or bike ride away. Tucked within one of Key West's most desirable neighborhoods, 1115 South Street captures everything people love about living here. Step inside and the home immediately feels open and inviting. Ten foot ceilings, warm Brazilian cherry floors, and an abundance of natural light create spaces that feel both elegant and comfortable. The entire first floor is designed for gathering, anchored by an impressive kitchen with abundant cabinetry, expansive countertops, and high end appliances that make cooking and entertaining equally enjoyable. As beautiful as the interior is, your attention naturally shifts outdoors. French doors open to a private tropical backyard where a large swimming pool, separate hot tub, and coral stone patios with IPE decking create a peaceful setting for relaxing or entertaining. Surrounded by mature landscaping, the backyard feels like your own private retreat. With both bedrooms located upstairs, the home offers a thoughtful separation between everyday living and personal space. The primary suite even enjoys its own balcony overlooking the backyard, providing a quiet place to begin or end the day. Beautifully maintained and thoughtfully designed, this is a home where every detail encourages you to slow down, entertain often, and enjoy the best of Key West living.

1115 South Street, Key West

$1,825,000

This new construction property is in a very quaint and quiet family friendly neighborhood in Key Largo. Centrally located on the island its a very close drive to a 5 Star rated VPK - 8th grade school, close to grocery shopping, leisure shops, local businesses, medical facilities and restaurants. With water views and water access, you are only a boat ride away from Blackwater Sound. A prestigious bay with boat parking for water front dining, shopping, and community parks.

3 Beds ⋅ 4 Baths ⋅ 618931 MLS

This new construction property is in a very quaint and quiet family friendly neighborhood in Key Largo. Centrally located on the island its a very close drive to a 5 Star rated VPK - 8th grade school, close to grocery shopping, leisure shops, local businesses, medical facilities and restaurants. With water views and water access, you are only a boat ride away from Blackwater Sound. A prestigious bay with boat parking for water front dining, shopping, and community parks.

764 Michael Dr, Key Largo

$1,800,000

Versatile mixed-use commercial opportunity in the heart of Stock Island! This fully fenced property features an approximately 2,060 sq. ft. CBS building situated on an approximately 7,458 sq. ft. lot, offering an excellent combination of indoor workspace and valuable outdoor yard space. A large 16' x 9'6'' overhead roll-up door provides convenient access to the building. This is a must-see property offering more space, functionality and potential than can be appreciated from the street. Ideal for an owner-user or investor seeking a flexible commercial property in a convenient Stock Island location with easy access to Key West and the Lower Keys. Real estate only; existing business and inventory are not included in the sale. Buyer to verify zoning, permitted uses, measurements and development potential with Monroe County. One of the property owners is a licensed Florida real estate broker.

1 Baths ⋅ 621666 MLS

Versatile mixed-use commercial opportunity in the heart of Stock Island! This fully fenced property features an approximately 2,060 sq. ft. CBS building situated on an approximately 7,458 sq. ft. lot, offering an excellent combination of indoor workspace and valuable outdoor yard space. A large 16' x 9'6'' overhead roll-up door provides convenient access to the building. This is a must-see property offering more space, functionality and potential than can be appreciated from the street. Ideal for an owner-user or investor seeking a flexible commercial property in a convenient Stock Island location with easy access to Key West and the Lower Keys. Real estate only; existing business and inventory are not included in the sale. Buyer to verify zoning, permitted uses, measurements and development potential with Monroe County. One of the property owners is a licensed Florida real estate broker.

5600 3rd Ave, Stock Island

$1,800,000

Key Colony Beach is one of the Florida's Keys most desired cities and due to this, there are very few buildable waterfront lots remaining and as of right now there are only 3 available and the next lot is priced at $2,650,000 making this the LOWEST PRICED Waterfront lot in all of Key Colony. Unlike most other cities in the keys, all Key Colony Beach lots are buildable, and permits will be issued once final plans are approved; no need to purchase building rights or have to wait years for a building permit. Lot has a Brand New 90Ft Seawall with Concrete Cap. What is even more special about this lot is that not only was the canal recently dredged, making it approximately 5 feet deep at low tide and approximately 40 feet wide; it offers rare privacy as across the canal will never have any homes built, which is very uncommon for Key Colony Beach. The lot is just shy of 10k sqft at 9756 and offers direct access to open ocean and the Bay via Vaca Cut in just minutes. For the avid boaters, there are three marine fuel docks just a short 8 minute boat ride away and two of them have bait tackle shops onsite. Key Colony's Sunset Park Beach is just a short walk from this lot and offers some of the best sunsets in the Florida Keys and it is dog friendly. For the avid golfers, Key Colony Beach Golf course is just a 3 minutes away and open to the public. Key Colony is also known for its annual lighted Boat Parade, which is a resident favorite. Do not miss the opportunity to acquire one of the last buildable waterfront lots in Key Colony. 180 12Th St just sold for $2,125,000 and was 415 sqft smaller. Plans are available for a 5 Bed, 5 Bath, 3,467 sqft Pool Home with multiple rear balconies overlooking the water views and surrounding tropical setting. by the very well-respected local builders Design Center. We have lenders offering construction financing up to 75% loan to value to finance the lot and the construction of the home or 40% loan to value for just the lot.

620981 MLS

Key Colony Beach is one of the Florida's Keys most desired cities and due to this, there are very few buildable waterfront lots remaining and as of right now there are only 3 available and the next lot is priced at $2,650,000 making this the LOWEST PRICED Waterfront lot in all of Key Colony. Unlike most other cities in the keys, all Key Colony Beach lots are buildable, and permits will be issued once final plans are approved; no need to purchase building rights or have to wait years for a building permit. Lot has a Brand New 90Ft Seawall with Concrete Cap. What is even more special about this lot is that not only was the canal recently dredged, making it approximately 5 feet deep at low tide and approximately 40 feet wide; it offers rare privacy as across the canal will never have any homes built, which is very uncommon for Key Colony Beach. The lot is just shy of 10k sqft at 9756 and offers direct access to open ocean and the Bay via Vaca Cut in just minutes. For the avid boaters, there are three marine fuel docks just a short 8 minute boat ride away and two of them have bait tackle shops onsite. Key Colony's Sunset Park Beach is just a short walk from this lot and offers some of the best sunsets in the Florida Keys and it is dog friendly. For the avid golfers, Key Colony Beach Golf course is just a 3 minutes away and open to the public. Key Colony is also known for its annual lighted Boat Parade, which is a resident favorite. Do not miss the opportunity to acquire one of the last buildable waterfront lots in Key Colony. 180 12Th St just sold for $2,125,000 and was 415 sqft smaller. Plans are available for a 5 Bed, 5 Bath, 3,467 sqft Pool Home with multiple rear balconies overlooking the water views and surrounding tropical setting. by the very well-respected local builders Design Center. We have lenders offering construction financing up to 75% loan to value to finance the lot and the construction of the home or 40% loan to value for just the lot.

200 15th Circle Ky, Key Colony

$1,800,000

Steeped in Key West history and unlike anything else available in Old Town, 511 Tabby Lane presents an opportunity to own one of the island's most extraordinary properties. Hidden away at the end of a charming pedestrian lane with direct access to iconic Duval Street, this remarkably private home offers a level of seclusion and potential that is virtually impossible to replicate. Rich in character and history, the property sits on an exceptionally deep 4,200-square-foot lot, a rarity in Old Town. There is simply no other property currently available that offers this combination of privacy, location, and land. The expansive lot provides endless possibilities, with ample space for a pool, pool house, guest quarters, lush gardens, outdoor entertaining areas, and more while still preserving the home's unique Old Town charm. Completely hidden from view behind a gated entrance, the property feels like a private tropical sanctuary in the heart of Key West. Whether you envision thoughtfully restoring the existing residence or creating a one-of-a-kind island compound, the possibilities are exceptional. The structure is believed to be a non-contributing building with HARC (buyer to verify), offering additional flexibility for future improvements. Adding to its rarity, the property is zoned for Transient License Receivership (buyer to verify), making it an incredibly attractive opportunity for investors, developers, or anyone seeking a truly unique Old Town residence. Properties of this caliber and significance rarely become available. 511 Tabby Lane represents a chance to own a piece of Key West history while creating something that future generations will treasure. This is Old Town at its most authentic--and an opportunity that simply cannot be duplicated.

3 Beds ⋅ 1 Baths ⋅ 620880 MLS

Steeped in Key West history and unlike anything else available in Old Town, 511 Tabby Lane presents an opportunity to own one of the island's most extraordinary properties. Hidden away at the end of a charming pedestrian lane with direct access to iconic Duval Street, this remarkably private home offers a level of seclusion and potential that is virtually impossible to replicate. Rich in character and history, the property sits on an exceptionally deep 4,200-square-foot lot, a rarity in Old Town. There is simply no other property currently available that offers this combination of privacy, location, and land. The expansive lot provides endless possibilities, with ample space for a pool, pool house, guest quarters, lush gardens, outdoor entertaining areas, and more while still preserving the home's unique Old Town charm. Completely hidden from view behind a gated entrance, the property feels like a private tropical sanctuary in the heart of Key West. Whether you envision thoughtfully restoring the existing residence or creating a one-of-a-kind island compound, the possibilities are exceptional. The structure is believed to be a non-contributing building with HARC (buyer to verify), offering additional flexibility for future improvements. Adding to its rarity, the property is zoned for Transient License Receivership (buyer to verify), making it an incredibly attractive opportunity for investors, developers, or anyone seeking a truly unique Old Town residence. Properties of this caliber and significance rarely become available. 511 Tabby Lane represents a chance to own a piece of Key West history while creating something that future generations will treasure. This is Old Town at its most authentic--and an opportunity that simply cannot be duplicated.

511 Tabby Ln, Key West

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