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Welcome to effortless Keys living! Built in 2017, this beautifully designed 3-bedroom, 3.5-bath CBS canal-front home offers 2,126 sq. ft. of living space, coastal style, privacy, and comfort. With no neighbors directly across the street, enjoy added privacy and openness. Solid CBS construction and impact-resistant windows and doors rated for winds up to 180 mph provide peace of mind. Set on a 50-foot-wide, deep, flow-through canal, the home offers quick, direct access to open water with no bridges. The spacious great room features soaring ceilings, abundant natural light, and a beautiful kitchen with quartz countertops, stainless steel appliances, and elegant finishes. Two ensuite guest bedrooms are on the main living level, while the entire upper level is a private primary retreat with a walk-in closet and bonus den, ideal for an office, workout space, or sitting area. Balconies on multiple levels invite you to enjoy morning coffee, coastal breezes, and stunning sunsets overlooking the salt ponds. A 40-foot concrete dock and 20,000-pound boat lift keep your boat right at home and ready to go. A fish-cleaning station adds convenience after a day on the water, while downstairs enclosed storage provides room for fishing gear, water toys, and Keys essentials. Less than two miles from a public boat ramp, this waterfront home puts world-class fishing, diving, and days on the water within easy reach. Whether it's a morning of fishing, an afternoon of diving, or a sunset cruise, enjoy all the Florida Keys have to offer. With comfort, privacy, and exceptional boating access, this home captures effortless island living!

3 Beds ⋅ 4 Baths ⋅ 621868 MLS

Welcome to effortless Keys living! Built in 2017, this beautifully designed 3-bedroom, 3.5-bath CBS canal-front home offers 2,126 sq. ft. of living space, coastal style, privacy, and comfort. With no neighbors directly across the street, enjoy added privacy and openness. Solid CBS construction and impact-resistant windows and doors rated for winds up to 180 mph provide peace of mind. Set on a 50-foot-wide, deep, flow-through canal, the home offers quick, direct access to open water with no bridges. The spacious great room features soaring ceilings, abundant natural light, and a beautiful kitchen with quartz countertops, stainless steel appliances, and elegant finishes. Two ensuite guest bedrooms are on the main living level, while the entire upper level is a private primary retreat with a walk-in closet and bonus den, ideal for an office, workout space, or sitting area. Balconies on multiple levels invite you to enjoy morning coffee, coastal breezes, and stunning sunsets overlooking the salt ponds. A 40-foot concrete dock and 20,000-pound boat lift keep your boat right at home and ready to go. A fish-cleaning station adds convenience after a day on the water, while downstairs enclosed storage provides room for fishing gear, water toys, and Keys essentials. Less than two miles from a public boat ramp, this waterfront home puts world-class fishing, diving, and days on the water within easy reach. Whether it's a morning of fishing, an afternoon of diving, or a sunset cruise, enjoy all the Florida Keys have to offer. With comfort, privacy, and exceptional boating access, this home captures effortless island living!

589 Pirates Rd, Little Torch

$2,299,000

Welcome to your private island retreat in the heart of Duck Key. Perfectly positioned just a few homes from the Seaview Channel, this exceptional waterfront residence offers instant access to both the Atlantic Ocean and the Gulf of Mexico—an ideal setting for boaters, entertainers, and families alike. This beautifully maintained home features three bedrooms and three baths, including downstairs living space, providing flexible options for guests, extended family, or a private suite. The remodeled kitchen and bathrooms showcase a European design, with wood cabinetry, granite countertops, and refined finishes throughout. Indoor-outdoor living is at the heart of this property. Step outside to a gorgeous pool and Jacuzzi, surrounded by a spacious pool deck with a built-in bar area, perfect for entertaining under the Florida sun. A large screened-in balcony captures beautiful water views in every direction, offering a serene space to relax and unwind. This space could easily be enclosed to add more living space. Additional highlights include a one-car garage, 75 feet of concrete dockage, and a fabulous canal setting just moments from open water. Easy to show and ready to enjoy, this Duck Key home delivers the very best of Keys living—luxury, lifestyle, and location.

3 Beds ⋅ 3 Baths ⋅ 618104 MLS

Welcome to your private island retreat in the heart of Duck Key. Perfectly positioned just a few homes from the Seaview Channel, this exceptional waterfront residence offers instant access to both the Atlantic Ocean and the Gulf of Mexico—an ideal setting for boaters, entertainers, and families alike. This beautifully maintained home features three bedrooms and three baths, including downstairs living space, providing flexible options for guests, extended family, or a private suite. The remodeled kitchen and bathrooms showcase a European design, with wood cabinetry, granite countertops, and refined finishes throughout. Indoor-outdoor living is at the heart of this property. Step outside to a gorgeous pool and Jacuzzi, surrounded by a spacious pool deck with a built-in bar area, perfect for entertaining under the Florida sun. A large screened-in balcony captures beautiful water views in every direction, offering a serene space to relax and unwind. This space could easily be enclosed to add more living space. Additional highlights include a one-car garage, 75 feet of concrete dockage, and a fabulous canal setting just moments from open water. Easy to show and ready to enjoy, this Duck Key home delivers the very best of Keys living—luxury, lifestyle, and location.

272 W Seaview Dr, Duck Key

81250 Overseas Highway Unit 5, Islamorada

$2,290,000

Only sophistication and class represented in Islamorada's most exclusive development, Tarpon Flats. This rare offering has underwent a full high-end renovation to satisfy the most distinguished buyer. The elegant paver driveway leads up to pristine grounds showing off it's manicured landscaping. One of only 12 luxury bayfront homes on a sprawling four-acre parcel. The property exudes a unique charm blending Old Florida allure with the timeless essence of Nantucket. Covered parking and a versatile multi-purpose room on the ground floor with a foyer entry. On the second floor you will find an open living space with the kitchen & dining room overlooking the bay, 2 bedrooms/2 bathrooms, and serene positioning for nightly sunsets. The third floor is dedicated to the master suite and maid's quarters with more amazing views from the private balcony. If amenities are what you're after, Tarpon Flats delivers on all fronts: a beautiful tennis court with covered seating for spectators, a rare greenhouse to nurture your beloved plants, a waterfront pool & gazebo leading down to the beachfront, and plenty of dockage for your skiff. Come see the exclusivity of Tarpon Flats for yourself.

4 Beds ⋅ 3 Baths ⋅ 621329 MLS

Only sophistication and class represented in Islamorada's most exclusive development, Tarpon Flats. This rare offering has underwent a full high-end renovation to satisfy the most distinguished buyer. The elegant paver driveway leads up to pristine grounds showing off it's manicured landscaping. One of only 12 luxury bayfront homes on a sprawling four-acre parcel. The property exudes a unique charm blending Old Florida allure with the timeless essence of Nantucket. Covered parking and a versatile multi-purpose room on the ground floor with a foyer entry. On the second floor you will find an open living space with the kitchen & dining room overlooking the bay, 2 bedrooms/2 bathrooms, and serene positioning for nightly sunsets. The third floor is dedicated to the master suite and maid's quarters with more amazing views from the private balcony. If amenities are what you're after, Tarpon Flats delivers on all fronts: a beautiful tennis court with covered seating for spectators, a rare greenhouse to nurture your beloved plants, a waterfront pool & gazebo leading down to the beachfront, and plenty of dockage for your skiff. Come see the exclusivity of Tarpon Flats for yourself.

81250 Overseas Highway Unit 5, Islamorada

$2,250,000

Prior to the development of Truman Annex which was a notable Naval base located in the center of Key West, now has many upscale homes and condos. This newly renovated 3-bedroom, 3-bathroom residence blends historic charm with cutting-edge contemporary design by interior designer David Smith. Step inside to soaring open ceilings with exposed ductwork and striking geometric lighting. Smart home technology is seamlessly integrated, allowing you to control the entire residence from your iPhone or iPad. Blackout and privacy illusion shades are installed throughout with impact windows and doors. The chef's kitchen is a true showpiece, featuring illuminated crystalline quartz countertops, an oversized island with under-counter lighting, and premium Miele appliances. A sleek induction cooktop with downdraft ventilation, walnut cabinetry with custom divider drawers, and 48'' x 48'' high-grade porcelain tile flooring complete the space. The primary suite offers ,a dramatic down-lit interlocking panel accent wall, a custom walk-in closet, and views of the historic Little White House. Spa-inspired bathrooms showcase porcelain walls, quartz sinks, smart toilets, and multi-head showers. The second en-suite bedroom features a private terrace, illuminated niche, and a luxurious walk-in shower. Every closet in the home is custom-designed and thoughtfully lit. Additional highlights include a fully furnished turnkey offering, oversized 8' doors, recessed window trims and baseboards, a large community pool, and one covered deeded parking space.

3 Beds ⋅ 3 Baths ⋅ 621771 MLS

Prior to the development of Truman Annex which was a notable Naval base located in the center of Key West, now has many upscale homes and condos. This newly renovated 3-bedroom, 3-bathroom residence blends historic charm with cutting-edge contemporary design by interior designer David Smith. Step inside to soaring open ceilings with exposed ductwork and striking geometric lighting. Smart home technology is seamlessly integrated, allowing you to control the entire residence from your iPhone or iPad. Blackout and privacy illusion shades are installed throughout with impact windows and doors. The chef's kitchen is a true showpiece, featuring illuminated crystalline quartz countertops, an oversized island with under-counter lighting, and premium Miele appliances. A sleek induction cooktop with downdraft ventilation, walnut cabinetry with custom divider drawers, and 48'' x 48'' high-grade porcelain tile flooring complete the space. The primary suite offers ,a dramatic down-lit interlocking panel accent wall, a custom walk-in closet, and views of the historic Little White House. Spa-inspired bathrooms showcase porcelain walls, quartz sinks, smart toilets, and multi-head showers. The second en-suite bedroom features a private terrace, illuminated niche, and a luxurious walk-in shower. Every closet in the home is custom-designed and thoughtfully lit. Additional highlights include a fully furnished turnkey offering, oversized 8' doors, recessed window trims and baseboards, a large community pool, and one covered deeded parking space.

115 Front St Unit APT 101, Key West

$2,250,000

Historic Old Town Charm Meets Modern Luxury. Situated next to the iconic Key West Cemetery, this legal duplex sits proudly on the island's highest point, offering an unbeatable location with unmatched peace of mind. With the original Conch House built in the late 1800s, this historic estate captures the classic romance of classic island architecture while providing a passive income opportunity. It is the ultimate configuration for a buyer looking to live the island dream in a beautiful residence while utilizing the separate unit as a legal rental to offset living costs. The main house is a spacious sanctuary featuring 4 bedrooms and 3 bathrooms. Every room blends historic character with modern comfort, offering an airy layout perfect for relaxation or entertainment. Steps away, the independent unit is a beautifully efficient studio apartment. This legal secondary unit serves as a desirable rental asset, an independent guest suite, or a private home office, adding incredible flexibility and value in a market where legal duplexes are highly coveted. While the property retains its rich late-19th-century soul, it also functions with the reliability of new construction. The entire property underwent a meticulous top-to-bottom renovation from 2022 to 2025, modernizing every major component. Upgrades include a new roof (2022), all new plumbing (2024), fully updated electrical systems (2024), attic insulation (2025), and a brand-new HVAC system (2024). Calling this property home means enjoying a quiet backdrop and unique neighborhood charm. You are just a short walk or bike ride away from world-class dining, vibrant nightlife, and pristine beaches. The driveway provides off-street parking for 1 vehicle.

5 Beds ⋅ 4 Baths ⋅ 621640 MLS

Historic Old Town Charm Meets Modern Luxury. Situated next to the iconic Key West Cemetery, this legal duplex sits proudly on the island's highest point, offering an unbeatable location with unmatched peace of mind. With the original Conch House built in the late 1800s, this historic estate captures the classic romance of classic island architecture while providing a passive income opportunity. It is the ultimate configuration for a buyer looking to live the island dream in a beautiful residence while utilizing the separate unit as a legal rental to offset living costs. The main house is a spacious sanctuary featuring 4 bedrooms and 3 bathrooms. Every room blends historic character with modern comfort, offering an airy layout perfect for relaxation or entertainment. Steps away, the independent unit is a beautifully efficient studio apartment. This legal secondary unit serves as a desirable rental asset, an independent guest suite, or a private home office, adding incredible flexibility and value in a market where legal duplexes are highly coveted. While the property retains its rich late-19th-century soul, it also functions with the reliability of new construction. The entire property underwent a meticulous top-to-bottom renovation from 2022 to 2025, modernizing every major component. Upgrades include a new roof (2022), all new plumbing (2024), fully updated electrical systems (2024), attic insulation (2025), and a brand-new HVAC system (2024). Calling this property home means enjoying a quiet backdrop and unique neighborhood charm. You are just a short walk or bike ride away from world-class dining, vibrant nightlife, and pristine beaches. The driveway provides off-street parking for 1 vehicle.

811 Olivia St, Key West

$2,250,000

If you are seeking a private tropical backyard oasis look no further. This charming 2 story home is situated on a corner parcel in a quiet and peaceful mid town neighborhood. Behind the white picket fence, you will be welcomed to a great room with dramatic ceiling heights, wrapped with sliding glass doorwalls that open to over 500 square feet of covered porches. This home has been very well maintained with several recent updates, including impact windows and doors, pool resurfacing, a new primary A/C unit, deck and interior paint and a charging station for an electric vehicle. A thoughtful floor plan great for entertaining, includes 3bd/3.5ba with the primary suite on the main level. Two additional bedrooms with ensuite baths are private to the upstairs. Built in just 1999 this home is an open palette awaiting your personal selection of cosmetic updates without the unknown obstacles of a historic home. The magic of this home lives in the sprawling backyard wrapped in mature tropical gardens with a large, heated saltwater pool. An excellent opportunity to personalize a well built home that caters to indoor/outdoor living ideal for the year round tropical climate!

3 Beds ⋅ 4 Baths ⋅ 621172 MLS

If you are seeking a private tropical backyard oasis look no further. This charming 2 story home is situated on a corner parcel in a quiet and peaceful mid town neighborhood. Behind the white picket fence, you will be welcomed to a great room with dramatic ceiling heights, wrapped with sliding glass doorwalls that open to over 500 square feet of covered porches. This home has been very well maintained with several recent updates, including impact windows and doors, pool resurfacing, a new primary A/C unit, deck and interior paint and a charging station for an electric vehicle. A thoughtful floor plan great for entertaining, includes 3bd/3.5ba with the primary suite on the main level. Two additional bedrooms with ensuite baths are private to the upstairs. Built in just 1999 this home is an open palette awaiting your personal selection of cosmetic updates without the unknown obstacles of a historic home. The magic of this home lives in the sprawling backyard wrapped in mature tropical gardens with a large, heated saltwater pool. An excellent opportunity to personalize a well built home that caters to indoor/outdoor living ideal for the year round tropical climate!

1300 Seminary St, Key West

$2,250,000

Some homes give you a place to live. KoKomo gives you a lifestyle, an investment opportunity, and a reason to look forward to every sunrise. What if your next home felt like a vacation--and could produce income when you're away? Welcome to KoKomo at 280 14th Street, a waterfront retreat on one of Key Colony Beach's quieter residential streets. Imagine beginning your morning with coffee on the expansive wraparound screened porch, feeling the island breeze, and deciding whether the day calls for fishing, diving, cruising--or relaxing beside your private pool. This inviting 3-bedroom, 2-bath single-family home features: • An open floor plan with vaulted ceilings • Direct porch access from every bedroom • Private pool and spacious waterfront setting • Two-car garage • Versatile bonus/flex space • Approximately 37 feet of dockage • Fish-cleaning station and bait freezer • Proven vacation-rental history dating to 2003 For boaters, the location makes every day on the water easier. Enjoy quick access through Vaca Cut to the Gulf, while the open Atlantic is also only minutes away. You'll be close to golf, pickleball, tennis, Sunset Park, the marina, restaurants, and the Cabana Club--yet comfortably removed from the busier areas of the island. Continue operating KoKomo as an income-producing vacation rental, enjoy it seasonally, or make it your full-time waterfront home. Key Colony Beach permits vacation rentals with a seven-night minimum stay, offering valuable flexibility for future ownership. Can you picture yourself here?

3 Beds ⋅ 2 Baths ⋅ 621083 MLS

Some homes give you a place to live. KoKomo gives you a lifestyle, an investment opportunity, and a reason to look forward to every sunrise. What if your next home felt like a vacation--and could produce income when you're away? Welcome to KoKomo at 280 14th Street, a waterfront retreat on one of Key Colony Beach's quieter residential streets. Imagine beginning your morning with coffee on the expansive wraparound screened porch, feeling the island breeze, and deciding whether the day calls for fishing, diving, cruising--or relaxing beside your private pool. This inviting 3-bedroom, 2-bath single-family home features: • An open floor plan with vaulted ceilings • Direct porch access from every bedroom • Private pool and spacious waterfront setting • Two-car garage • Versatile bonus/flex space • Approximately 37 feet of dockage • Fish-cleaning station and bait freezer • Proven vacation-rental history dating to 2003 For boaters, the location makes every day on the water easier. Enjoy quick access through Vaca Cut to the Gulf, while the open Atlantic is also only minutes away. You'll be close to golf, pickleball, tennis, Sunset Park, the marina, restaurants, and the Cabana Club--yet comfortably removed from the busier areas of the island. Continue operating KoKomo as an income-producing vacation rental, enjoy it seasonally, or make it your full-time waterfront home. Key Colony Beach permits vacation rentals with a seven-night minimum stay, offering valuable flexibility for future ownership. Can you picture yourself here?

280 14th St, Key Colony

$2,250,000

Prime Multi Unit property in Old Town. Six legal apartments with 6 off street parking spaces is rarely available. There is a total of 10 bedrooms and 6 baths, divided into Three 1bd/1ba units, Two 2 bd/1ba units and one 3bd/1ba unit. Two story CBS & Frame building has total of 3,876 sf. Building sits on good size 3,598 sf. lot that runs from Pohalski St. to Havana Lane giving each tenant easy access to their apartment and off street parking spot. Each apartment has it's own separate Electric and Water meter. Lot sits in a BFE flood zone, former X flood zone, and is high and dry. Gross rents total $14,500 per month with limited expenses. Property has been in the family for generations and ready to pass on to a new owner. Perfect for a long term investor, 1031 Exchange Replacement Property or Employee Housing!

10 Beds ⋅ 6 Baths ⋅ 620102 MLS

Prime Multi Unit property in Old Town. Six legal apartments with 6 off street parking spaces is rarely available. There is a total of 10 bedrooms and 6 baths, divided into Three 1bd/1ba units, Two 2 bd/1ba units and one 3bd/1ba unit. Two story CBS & Frame building has total of 3,876 sf. Building sits on good size 3,598 sf. lot that runs from Pohalski St. to Havana Lane giving each tenant easy access to their apartment and off street parking spot. Each apartment has it's own separate Electric and Water meter. Lot sits in a BFE flood zone, former X flood zone, and is high and dry. Gross rents total $14,500 per month with limited expenses. Property has been in the family for generations and ready to pass on to a new owner. Perfect for a long term investor, 1031 Exchange Replacement Property or Employee Housing!

912 Pohalski St, Key West

$2,250,000

Prime Multi Unit property in Old Town. Six legal apartments with 6 off street parking spaces is rarely available. There is a total of 10 bedrooms and 6 baths, divided into Three 1bd/1ba units, Two 2 bd/1ba units and one 3bd/1ba unit. Two story CBS & Frame building has total of 3,876 sf. Building sits on good size 3,598 sf. lot that runs from Pohalski St. to Havana Lane giving each tenant easy access to their apartment and off street parking spot. Each apartment has it's own separate Electric and Water meter. Lot sits in a BFE flood zone, former X flood zone, and is high and dry. Gross rents total $14,500 per month with limited expenses. Property has been in the family for generations and ready to pass on to a new owner. Perfect for a long term investor, 1031 Exchange Replacement Property or Employee Housing!

10 Beds ⋅ 6 Baths ⋅ 620101 MLS

Prime Multi Unit property in Old Town. Six legal apartments with 6 off street parking spaces is rarely available. There is a total of 10 bedrooms and 6 baths, divided into Three 1bd/1ba units, Two 2 bd/1ba units and one 3bd/1ba unit. Two story CBS & Frame building has total of 3,876 sf. Building sits on good size 3,598 sf. lot that runs from Pohalski St. to Havana Lane giving each tenant easy access to their apartment and off street parking spot. Each apartment has it's own separate Electric and Water meter. Lot sits in a BFE flood zone, former X flood zone, and is high and dry. Gross rents total $14,500 per month with limited expenses. Property has been in the family for generations and ready to pass on to a new owner. Perfect for a long term investor, 1031 Exchange Replacement Property or Employee Housing!

912 Pohalski St, Key West

$2,249,000

Some places in Key West you visit. This one you call home. 1104 Packer St is a storybook Conch cottage, full of surprises & charm. Inside, a grand foyer & tall ceilings welcome you in, and the home opens with a warmth that feels instantly familiar. Hardwood floors run throughout & original pulley windows nod to the island's history. Enjoy morning coffee or evening sundown from your own front porch. The open living & dining room is wrapped in windows framing your backyard oasis, with vaulted ceilings & natural light in every corner. French doors open to the pool, so gatherings flow easily from table to terrace. The large kitchen, with new Bosch appliances, Viking range & tons of storage, overlooks the pool & living/dining areas allowing the host to be part of the celebration. Step outside & the world softens. The new heated saltwater pool, installed 2026, shimmers beside travertine decking & an undercover porch/lanai, a private sanctuary for long afternoons & quiet evenings. When night falls & the island hushes, stretch out on a lounge chair & count the stars. The large ensuite primary bedroom is a true retreat, with a stunning new bath: two vanities, a classic clawfoot tub for long, quiet soaks & a spa-like shower. A third bedroom/office has a private entrance. Upstairs, a second guest bedroom offers an ensuite bath, & and private ensuite guest cottage keeps visitors comfortable & independent. Recent remodel includes new roof, AC, heated saltwater pool, tankless water heater, refreshed kitchen w/new appliances, & remodeled primary bath. Just arrive & exhale. This private home sits in a quiet, desired location, low risk flood zone only steps from Duval St, restaurants, entertainment & the beach. Old Conch soul, thoughtfully modern, ready to be yours. Come home to 1104 Packer St.

4 Beds ⋅ 4 Baths ⋅ 621864 MLS

Some places in Key West you visit. This one you call home. 1104 Packer St is a storybook Conch cottage, full of surprises & charm. Inside, a grand foyer & tall ceilings welcome you in, and the home opens with a warmth that feels instantly familiar. Hardwood floors run throughout & original pulley windows nod to the island's history. Enjoy morning coffee or evening sundown from your own front porch. The open living & dining room is wrapped in windows framing your backyard oasis, with vaulted ceilings & natural light in every corner. French doors open to the pool, so gatherings flow easily from table to terrace. The large kitchen, with new Bosch appliances, Viking range & tons of storage, overlooks the pool & living/dining areas allowing the host to be part of the celebration. Step outside & the world softens. The new heated saltwater pool, installed 2026, shimmers beside travertine decking & an undercover porch/lanai, a private sanctuary for long afternoons & quiet evenings. When night falls & the island hushes, stretch out on a lounge chair & count the stars. The large ensuite primary bedroom is a true retreat, with a stunning new bath: two vanities, a classic clawfoot tub for long, quiet soaks & a spa-like shower. A third bedroom/office has a private entrance. Upstairs, a second guest bedroom offers an ensuite bath, & and private ensuite guest cottage keeps visitors comfortable & independent. Recent remodel includes new roof, AC, heated saltwater pool, tankless water heater, refreshed kitchen w/new appliances, & remodeled primary bath. Just arrive & exhale. This private home sits in a quiet, desired location, low risk flood zone only steps from Duval St, restaurants, entertainment & the beach. Old Conch soul, thoughtfully modern, ready to be yours. Come home to 1104 Packer St.

1104 Packer St, Key West

$2,249,000

Over 3400 sqft of Luxury Living is featured with this 2007 custom built CBS in the gated community of Stirrup Key Sub in Marathon. Elevated water views, a deeded boat slip, protected community marina, multiple outdoor living areas and a private pool. Designed for both everyday comfort and entertaining, this multi-level home offers generous interior space, flexible living areas, and a thoughtful indoor-outdoor layout. The ground level features a three-car garage, ample storage, and direct access to the pool area, creating an easy flow for relaxing, hosting, and enjoying the Keys lifestyle. The second floor serves as the main living level with two bedrooms, two full baths, a full kitchen, and open living and dining areas that extend onto a large screened lanai. This level is ideal for casual gatherings, quiet mornings, and evening breezes. The third floor offers a private primary suite, sitting area or fourth bedroom, bar/kitchenette, fireplace, spa-style bath, and an expansive lanai with peaceful elevated views. A spiral staircase leads to the fourth-floor widow's walk, finished with travertine flooring and a water hookup. From this vantage point, panoramic views stretch across Marathon and toward the Gulf, creating a quiet setting for sunrise, sunset, and open-air relaxation. A private nature path winds through preserved surroundings and leads to a Gulf-front observation dock, ideal for wildlife viewing and enjoying the surrounding natural setting. Additional features include a lift to the second floor for added convenience. Centrally located in Marathon, the home offers convenient access to shopping, dining, & daily necessities. With a deeded marina slip, elevated water views, pool, garage space, storage, multiple lanais, and a flexible custom layout, this property offers a rare combination of privacy, space, and boating access in Marathon. Schedule a private showing to experience this custom home and deeded marina slip in person.

4 Beds ⋅ 3 Baths ⋅ 619793 MLS

Over 3400 sqft of Luxury Living is featured with this 2007 custom built CBS in the gated community of Stirrup Key Sub in Marathon. Elevated water views, a deeded boat slip, protected community marina, multiple outdoor living areas and a private pool. Designed for both everyday comfort and entertaining, this multi-level home offers generous interior space, flexible living areas, and a thoughtful indoor-outdoor layout. The ground level features a three-car garage, ample storage, and direct access to the pool area, creating an easy flow for relaxing, hosting, and enjoying the Keys lifestyle. The second floor serves as the main living level with two bedrooms, two full baths, a full kitchen, and open living and dining areas that extend onto a large screened lanai. This level is ideal for casual gatherings, quiet mornings, and evening breezes. The third floor offers a private primary suite, sitting area or fourth bedroom, bar/kitchenette, fireplace, spa-style bath, and an expansive lanai with peaceful elevated views. A spiral staircase leads to the fourth-floor widow's walk, finished with travertine flooring and a water hookup. From this vantage point, panoramic views stretch across Marathon and toward the Gulf, creating a quiet setting for sunrise, sunset, and open-air relaxation. A private nature path winds through preserved surroundings and leads to a Gulf-front observation dock, ideal for wildlife viewing and enjoying the surrounding natural setting. Additional features include a lift to the second floor for added convenience. Centrally located in Marathon, the home offers convenient access to shopping, dining, & daily necessities. With a deeded marina slip, elevated water views, pool, garage space, storage, multiple lanais, and a flexible custom layout, this property offers a rare combination of privacy, space, and boating access in Marathon. Schedule a private showing to experience this custom home and deeded marina slip in person.

205 Stirrup, Marathon

$2,247,000

Prime Old Town Key West Location with Off Street Parking and 55 ft of Truman Avenue Frontage. The property currently consists of four licensed rental apartments; one 2BR/1BA unit and three 1BR/1BA units. Property formerly configured for two business offices. Perfect for your business downstairs and reside upstairs. Generous off-street parking; a rare and valuable feature in Old Town, enhances desirability for business and/or residential occupants. Lots of Options: long-term rentals, monthly vacation rentals, employee housing, or mixed-use potential with commercial use on the ground level and residential above. The flexible interior layout also offers the potential to be a duplex. Or reimagine as a spacious single-family residence. Conversion to four condos offers the highest investment return. This is an extremely well-located property with multiple use possibilities. Buyer to verify any conversion from existing use. Classic Conch-style construction with covered porches adds to the property's island appeal and long-term value.

5 Beds ⋅ 4 Baths ⋅ 619930 MLS

Prime Old Town Key West Location with Off Street Parking and 55 ft of Truman Avenue Frontage. The property currently consists of four licensed rental apartments; one 2BR/1BA unit and three 1BR/1BA units. Property formerly configured for two business offices. Perfect for your business downstairs and reside upstairs. Generous off-street parking; a rare and valuable feature in Old Town, enhances desirability for business and/or residential occupants. Lots of Options: long-term rentals, monthly vacation rentals, employee housing, or mixed-use potential with commercial use on the ground level and residential above. The flexible interior layout also offers the potential to be a duplex. Or reimagine as a spacious single-family residence. Conversion to four condos offers the highest investment return. This is an extremely well-located property with multiple use possibilities. Buyer to verify any conversion from existing use. Classic Conch-style construction with covered porches adds to the property's island appeal and long-term value.

1104 Truman Ave, Key West

$2,247,000

LOTS OF OPTIONS! Prime Old Town Key West Location with Off Street Parking. A variety of uses; long-term rentals, monthly vacation rentals, employee housing, or mixed-use potential with possible commercial use on the ground level and residential above. The flexible interior layout offers the potential to be a duplex or reimagined as a spacious single-family residence. Conversion to four condos offers the highest investment return. (Buyer to verify) Generous off-street parking; a rare and valuable feature in Old Town, enhances desirability for business and/or residential occupants. Classic Conch-style construction with covered porches adds to the property's island appeal and long-term value. The property currently consists of four apartments; one 2BR/1BA unit and three 1BR/1BA units, all licensed rentals.. This is an extremely well-located property with multiple use possibilities in a high-demand market.

5 Beds ⋅ 4 Baths ⋅ 619927 MLS

LOTS OF OPTIONS! Prime Old Town Key West Location with Off Street Parking. A variety of uses; long-term rentals, monthly vacation rentals, employee housing, or mixed-use potential with possible commercial use on the ground level and residential above. The flexible interior layout offers the potential to be a duplex or reimagined as a spacious single-family residence. Conversion to four condos offers the highest investment return. (Buyer to verify) Generous off-street parking; a rare and valuable feature in Old Town, enhances desirability for business and/or residential occupants. Classic Conch-style construction with covered porches adds to the property's island appeal and long-term value. The property currently consists of four apartments; one 2BR/1BA unit and three 1BR/1BA units, all licensed rentals.. This is an extremely well-located property with multiple use possibilities in a high-demand market.

1104 Truman Ave, Key West

$2,246,000

Built for the offshore lifestyle, this exceptional Summerland Key waterfront home blends luxury coastal living with the kind of boating access serious anglers dream about. Completely renovated from top to bottom, the property sits on a deep water canal with 60 feet of brand new concrete dockage and quick direct access to open water, making it ideal for larger center consoles, sportfish boats, and offshore cruising. Inside, the home was designed for relaxed Keys living with vaulted ceilings, impact windows and doors, quartz countertops, custom wood cabinetry, stainless steel appliances, and an open layout filled with natural light and canal views. The spacious primary suite is privately situated on the second floor, offering a peaceful retreat with elevated views and added separation from the guest accommodations below. The outdoor living experience is what truly sets this property apart. The waterfront pool features all brand-new equipment, including a heater and chiller, allowing for year-round enjoyment in every season. A portion of the pool area is partially covered, creating the perfect shaded outdoor lounge space after a day on the water. Covered balconies, spacious patios, and tropical landscaping give the property a true private resort feel. The custom putting green and mini golf area adds a unique touch rarely found in the Keys, creating an incredible space for entertaining guests while enjoying the waterfront setting. Whether you're heading offshore for tuna and swordfish, running to the reef, or enjoying sunset cruises through the Lower Keys, this location puts you minutes from some of the best boating and fishing in the Florida Keys. Built with durable Hardie board construction, a metal roof, impact windows and doors, covered parking, and more than 1,000 square feet of enclosed storage space underneath the home, this turnkey waterfront retreat offers the perfect balance of luxury, functionality, and the authentic Florida Keys boating lifestyle.

3 Beds ⋅ 2 Baths ⋅ 620177 MLS

Built for the offshore lifestyle, this exceptional Summerland Key waterfront home blends luxury coastal living with the kind of boating access serious anglers dream about. Completely renovated from top to bottom, the property sits on a deep water canal with 60 feet of brand new concrete dockage and quick direct access to open water, making it ideal for larger center consoles, sportfish boats, and offshore cruising. Inside, the home was designed for relaxed Keys living with vaulted ceilings, impact windows and doors, quartz countertops, custom wood cabinetry, stainless steel appliances, and an open layout filled with natural light and canal views. The spacious primary suite is privately situated on the second floor, offering a peaceful retreat with elevated views and added separation from the guest accommodations below. The outdoor living experience is what truly sets this property apart. The waterfront pool features all brand-new equipment, including a heater and chiller, allowing for year-round enjoyment in every season. A portion of the pool area is partially covered, creating the perfect shaded outdoor lounge space after a day on the water. Covered balconies, spacious patios, and tropical landscaping give the property a true private resort feel. The custom putting green and mini golf area adds a unique touch rarely found in the Keys, creating an incredible space for entertaining guests while enjoying the waterfront setting. Whether you're heading offshore for tuna and swordfish, running to the reef, or enjoying sunset cruises through the Lower Keys, this location puts you minutes from some of the best boating and fishing in the Florida Keys. Built with durable Hardie board construction, a metal roof, impact windows and doors, covered parking, and more than 1,000 square feet of enclosed storage space underneath the home, this turnkey waterfront retreat offers the perfect balance of luxury, functionality, and the authentic Florida Keys boating lifestyle.

848 E Caribbean Dr, Summerland

$2,229,000

Welcome to 3801 Flagler Avenue in beautiful Key West! A stunning home designed for luxury, comfort, and privacy, offering the perfect indoor/outdoor island lifestyle. Situated on an oversized 9,500-square-foot lot, a rare find in Key West, this property features two separate structures, a spectacular two-tier saltwater pool with a tanning ledge and waterfall feature, and beautifully landscaped tropical grounds. The entire property feels like your own private resort. The main residence features one bedroom, one bathroom, a gourmet chef's kitchen, a spacious living area, and a beautiful second-floor loft. The open design and natural light give this home a peaceful, Zen-like feel. The second structure, located above the oversized two-car garage, provides the perfect accommodations for family and guests. Featuring two bedrooms, two bathrooms, and a generous living room, this separate living space offers exceptional comfort and privacy. Your guests will feel right at home while everyone enjoys their own personal space. Built for peace of mind and designed for effortless living, this newer-construction home offers exceptional features, including an elevated design above the FEMA AE-8 flood elevation, a whole-house generator, hurricane-impact windows and doors, and durable Hardi Board siding. Enjoy all the charm and beauty of Key West without the constant maintenance often associated with historic island homes. Step outside and discover your own tropical paradise. The beautifully landscaped grounds and stunning saltwater pool create a resort-style setting perfect for entertaining, unwinding or spending endless days soaking up the Florida Keys sunshine. Luxury, privacy, and convenience come together beautifully at 3801 Flagler Avenue. Owner is a licensed Florida Real Estate Broker. Call today to schedule your private showing!

3 Beds ⋅ 3 Baths ⋅ 621725 MLS

Welcome to 3801 Flagler Avenue in beautiful Key West! A stunning home designed for luxury, comfort, and privacy, offering the perfect indoor/outdoor island lifestyle. Situated on an oversized 9,500-square-foot lot, a rare find in Key West, this property features two separate structures, a spectacular two-tier saltwater pool with a tanning ledge and waterfall feature, and beautifully landscaped tropical grounds. The entire property feels like your own private resort. The main residence features one bedroom, one bathroom, a gourmet chef's kitchen, a spacious living area, and a beautiful second-floor loft. The open design and natural light give this home a peaceful, Zen-like feel. The second structure, located above the oversized two-car garage, provides the perfect accommodations for family and guests. Featuring two bedrooms, two bathrooms, and a generous living room, this separate living space offers exceptional comfort and privacy. Your guests will feel right at home while everyone enjoys their own personal space. Built for peace of mind and designed for effortless living, this newer-construction home offers exceptional features, including an elevated design above the FEMA AE-8 flood elevation, a whole-house generator, hurricane-impact windows and doors, and durable Hardi Board siding. Enjoy all the charm and beauty of Key West without the constant maintenance often associated with historic island homes. Step outside and discover your own tropical paradise. The beautifully landscaped grounds and stunning saltwater pool create a resort-style setting perfect for entertaining, unwinding or spending endless days soaking up the Florida Keys sunshine. Luxury, privacy, and convenience come together beautifully at 3801 Flagler Avenue. Owner is a licensed Florida Real Estate Broker. Call today to schedule your private showing!

3801 Flagler Ave, Key West

$2,220,000

High quality concrete 3/2 in Summerland Cove. One of the best boating communities in the lower Keys for deep water, aqua blue canal water, and oceanside access with no bridges! Brand new 60' concrete dock has just been installed. Step inside to find the fresh, modern renovation done in 2024. Featuring 3 bedrooms 2 baths with the private 3rd floor primary suite. 24'' modern white tile throughout, impact windows and doors with custom window blinds with a filtered light or privacy mode. Expansive great room with vaulted ceiling, all new recessed lighting, coastal kitchen with quartz countertops and waterfall edge. The large covered back porch overlooks the canal. Rear stairs to the custom concrete pool and 60' concrete dock. Lower storage room and covered parking. Enjoy access to world class fishing and diving sites in just minutes. Situated on a 60x100 ft lot in one of the most desirable neighborhoods in the Lower Keys.

3 Beds ⋅ 2 Baths ⋅ 619294 MLS

High quality concrete 3/2 in Summerland Cove. One of the best boating communities in the lower Keys for deep water, aqua blue canal water, and oceanside access with no bridges! Brand new 60' concrete dock has just been installed. Step inside to find the fresh, modern renovation done in 2024. Featuring 3 bedrooms 2 baths with the private 3rd floor primary suite. 24'' modern white tile throughout, impact windows and doors with custom window blinds with a filtered light or privacy mode. Expansive great room with vaulted ceiling, all new recessed lighting, coastal kitchen with quartz countertops and waterfall edge. The large covered back porch overlooks the canal. Rear stairs to the custom concrete pool and 60' concrete dock. Lower storage room and covered parking. Enjoy access to world class fishing and diving sites in just minutes. Situated on a 60x100 ft lot in one of the most desirable neighborhoods in the Lower Keys.

937 Gulf Dr, Summerland

$2,200,000

Turn your dream home into reality. Discover the opportunity to create your own private retreat in the exclusive and highly desirable community of Duck Key, Florida. This exceptional vacant lot offers the perfect canvas to bring your vision of luxury island living to life. with planning completed and building permits ready for construction, you can move one step closer to designing and building a custom residence tailored to your lifestyle. Duck Key offers a distinctive blend of tranquility, privacy and costal sophistication.

621751 MLS

Turn your dream home into reality. Discover the opportunity to create your own private retreat in the exclusive and highly desirable community of Duck Key, Florida. This exceptional vacant lot offers the perfect canvas to bring your vision of luxury island living to life. with planning completed and building permits ready for construction, you can move one step closer to designing and building a custom residence tailored to your lifestyle. Duck Key offers a distinctive blend of tranquility, privacy and costal sophistication.

276 W Seaview Dr, Duck

$2,200,000

This custom-built 2015, 3-story canal-front residence sits on a rare 10.5-foot elevation on Key Largo's oceanside, Mile Marker 95.5. With 3,018 square feet of interior living space, this 4/3 home features bamboo & porcelain tile flooring, plantation shutters, custom cabinetry, Silestone countertops, SS appliances, & a reverse-osmosis water filtration system. The second-story's main living area opens to an oversized screened porch with removable all-season windows and a wraparound balcony, while modern conveniences like a built-in whole-house vacuum and intercom system run throughout. The top floor features a primary bedroom suite with French doors opening to a private balcony, custom Elfa closet organization, and a convenient laundry chute to the laundry room. The property's ground level offers outdoor lifestyle with a 2-car garage and a modular garage storage system, game room, tackle room, Jacuzzi, outdoor kitchen/sink, and an expanded deck under a retractable awning. Fully fenced, mechanically gated grounds include a pavered driveway, extra side parking, landscape lighting, a rainwater irrigation system, security cameras, & roll-down storm shutters. The deep-water canal setup includes a 10,000-pound boat lift and davits, a canal aerator, a fish-cleaning station, and an outdoor shower. Cruise out and enjoy the sandbars of Dove & Rodriguez keys, a protected bird population area, or world-class diving at the protected Molasses Reef, part of the National Marine Sanctuary. Welcome home! VOLUNTARY HOA IS $150 PER YEAR

4 Beds ⋅ 3 Baths ⋅ 621657 MLS

This custom-built 2015, 3-story canal-front residence sits on a rare 10.5-foot elevation on Key Largo's oceanside, Mile Marker 95.5. With 3,018 square feet of interior living space, this 4/3 home features bamboo & porcelain tile flooring, plantation shutters, custom cabinetry, Silestone countertops, SS appliances, & a reverse-osmosis water filtration system. The second-story's main living area opens to an oversized screened porch with removable all-season windows and a wraparound balcony, while modern conveniences like a built-in whole-house vacuum and intercom system run throughout. The top floor features a primary bedroom suite with French doors opening to a private balcony, custom Elfa closet organization, and a convenient laundry chute to the laundry room. The property's ground level offers outdoor lifestyle with a 2-car garage and a modular garage storage system, game room, tackle room, Jacuzzi, outdoor kitchen/sink, and an expanded deck under a retractable awning. Fully fenced, mechanically gated grounds include a pavered driveway, extra side parking, landscape lighting, a rainwater irrigation system, security cameras, & roll-down storm shutters. The deep-water canal setup includes a 10,000-pound boat lift and davits, a canal aerator, a fish-cleaning station, and an outdoor shower. Cruise out and enjoy the sandbars of Dove & Rodriguez keys, a protected bird population area, or world-class diving at the protected Molasses Reef, part of the National Marine Sanctuary. Welcome home! VOLUNTARY HOA IS $150 PER YEAR

1217 Mockingbird Rd, Key Largo

$2,200,000

Welcome to 273 W Seaview Dr, a private retreat in the heart of Duck Key, home to Hawks Cay Resort and some of the best boating and fishing waters in the Florida Keys. Built in 2020 on a 15,247 SF lot, this concrete home is elevated on concrete pilings and engineered to withstand hurricane force winds, with impact windows and doors throughout for lasting peace of mind and favorable insurance considerations. The main living level is reached by two separate entries, a front stairway and a rear balcony, and offers 3 bedrooms, 2 full bathrooms, and an in unit washer and dryer across a bright, thoughtfully finished floor plan with custom exterior finishes, drywall interiors, a flat clay tile roof, and forced air cooling. Below, the ground level provides extensive covered parking and storage space, along with a shaded open porch, ideal for boat gear or beach equipment. Outdoors, the property has been extensively upgraded. The owner just completed a brand new 288 SF pool with a paver deck, and recently added a paver brick driveway and multiple brick and tile patio areas for entertaining. The yard is enclosed with wrought iron fencing and gates for added privacy. A standout feature is the detached 2,046 SF garage on the south side of the property, built in 2023 with room for up to nine vehicles, a rare find for boat owners, car collectors, or anyone in need of serious storage space in the Keys. This property suits a vacation home or full time residence equally well. Duck Key offers a welcoming, close knit island community along with excellent public, private, and charter schools nearby. Enjoy the Florida Keys lifestyle: no state income tax, roughly 230 sunny days a year, and some of the most stunning beaches, fishing, and boating waters in the country. Live securely, comfortably, and luxuriously in paradise, and schedule your private showing today.

3 Beds ⋅ 2 Baths ⋅ 620645 MLS

Welcome to 273 W Seaview Dr, a private retreat in the heart of Duck Key, home to Hawks Cay Resort and some of the best boating and fishing waters in the Florida Keys. Built in 2020 on a 15,247 SF lot, this concrete home is elevated on concrete pilings and engineered to withstand hurricane force winds, with impact windows and doors throughout for lasting peace of mind and favorable insurance considerations. The main living level is reached by two separate entries, a front stairway and a rear balcony, and offers 3 bedrooms, 2 full bathrooms, and an in unit washer and dryer across a bright, thoughtfully finished floor plan with custom exterior finishes, drywall interiors, a flat clay tile roof, and forced air cooling. Below, the ground level provides extensive covered parking and storage space, along with a shaded open porch, ideal for boat gear or beach equipment. Outdoors, the property has been extensively upgraded. The owner just completed a brand new 288 SF pool with a paver deck, and recently added a paver brick driveway and multiple brick and tile patio areas for entertaining. The yard is enclosed with wrought iron fencing and gates for added privacy. A standout feature is the detached 2,046 SF garage on the south side of the property, built in 2023 with room for up to nine vehicles, a rare find for boat owners, car collectors, or anyone in need of serious storage space in the Keys. This property suits a vacation home or full time residence equally well. Duck Key offers a welcoming, close knit island community along with excellent public, private, and charter schools nearby. Enjoy the Florida Keys lifestyle: no state income tax, roughly 230 sunny days a year, and some of the most stunning beaches, fishing, and boating waters in the country. Live securely, comfortably, and luxuriously in paradise, and schedule your private showing today.

273 W Seaview Dr, Duck Key

$2,200,000

Welcome to Your Slice of Paradise in the Florida Keys Discover the perfect blend of island charm, waterfront living, and investment potential in this fully furnished, turnkey home in the heart of Marathon. Whether you're searching for a vacation getaway, a full-time residence, or a proven income-producing property, this exceptional home offers it all. Property Highlights 3 Bedrooms | 2 Bathrooms Bonus room/flex space perfect for guests, a home office, or additional living space Fully furnished and move-in ready Excellent vacation rental history 17,000 lb boat lift 150 feet of seawall Private tiki hut for relaxing and entertaining Short walk to Sombrero Beach Just a 3-minute idle boat ride to the open Atlantic Ocean Minutes from the iconic Sombrero Key Lighthouse Exceptional boating access with quick ocean access Beautiful outdoor living spaces designed to embrace the Florida Keys lifestyle Wake up to gentle ocean breezes, spend your days boating or relaxing on the beach, and unwind beneath the tiki hut as the sun sets. With outstanding boating access, a sought-after location, and a successful vacation rental history, this waterfront retreat is the perfect opportunity to experience the very best of island living. Live like you're on vacation every day in the beautiful Florida Keys.

3 Beds ⋅ 2 Baths ⋅ 620513 MLS

Welcome to Your Slice of Paradise in the Florida Keys Discover the perfect blend of island charm, waterfront living, and investment potential in this fully furnished, turnkey home in the heart of Marathon. Whether you're searching for a vacation getaway, a full-time residence, or a proven income-producing property, this exceptional home offers it all. Property Highlights 3 Bedrooms | 2 Bathrooms Bonus room/flex space perfect for guests, a home office, or additional living space Fully furnished and move-in ready Excellent vacation rental history 17,000 lb boat lift 150 feet of seawall Private tiki hut for relaxing and entertaining Short walk to Sombrero Beach Just a 3-minute idle boat ride to the open Atlantic Ocean Minutes from the iconic Sombrero Key Lighthouse Exceptional boating access with quick ocean access Beautiful outdoor living spaces designed to embrace the Florida Keys lifestyle Wake up to gentle ocean breezes, spend your days boating or relaxing on the beach, and unwind beneath the tiki hut as the sun sets. With outstanding boating access, a sought-after location, and a successful vacation rental history, this waterfront retreat is the perfect opportunity to experience the very best of island living. Live like you're on vacation every day in the beautiful Florida Keys.

64 Tingler Ln, Marathon

$2,200,000

Welcome to 317 E Seaview Cir, now for sale on Duck Key's exclusive Yacht Club Island. Built in 2021, this three story concrete home is elevated on concrete pilings for lasting hurricane resilience, with a paver driveway and walkway leading to the entrance. The home offers 3 bedrooms and 2.5 bathrooms, along with an included washer and dryer. Take in open ocean views from both the second and third stories, and enjoy the added peace of a vacant lot next door. The beautifully landscaped grounds create a true island living feel, and the concrete pool, finished with a paver deck, heat pump, and a four foot high self closing safety gate, is ready for year round enjoyment. Duck Key offers a welcoming, close knit island community along with excellent public, private, and charter schools nearby. Enjoy the Florida Keys lifestyle: no state income tax, roughly 230 sunny days a year, and some of the most beautiful beaches, fishing, and boating waters in the country. Schedule your private showing today.

3 Beds ⋅ 3 Baths ⋅ 618195 MLS

Welcome to 317 E Seaview Cir, now for sale on Duck Key's exclusive Yacht Club Island. Built in 2021, this three story concrete home is elevated on concrete pilings for lasting hurricane resilience, with a paver driveway and walkway leading to the entrance. The home offers 3 bedrooms and 2.5 bathrooms, along with an included washer and dryer. Take in open ocean views from both the second and third stories, and enjoy the added peace of a vacant lot next door. The beautifully landscaped grounds create a true island living feel, and the concrete pool, finished with a paver deck, heat pump, and a four foot high self closing safety gate, is ready for year round enjoyment. Duck Key offers a welcoming, close knit island community along with excellent public, private, and charter schools nearby. Enjoy the Florida Keys lifestyle: no state income tax, roughly 230 sunny days a year, and some of the most beautiful beaches, fishing, and boating waters in the country. Schedule your private showing today.

317 E Seaview Cir, Duck Key

$2,199,000

Beyond the doors of 3821 Eagle Avenue, a private courtyard evokes the intimacy of a Tuscan retreat. Cascading vines, sculptural bougainvillea and lush greenery frame the 29x15 pool while a shaded terrace invites long lunches that linger into evening. Expansive folding glass doors connect the interiors to the outdoors allowing gatherings to flow naturally from kitchen to poolside. Warm wood cabinetry and a substantial waterfall edge island anchor a kitchen that knows culinary appointed with a Wolf induction range, Wolf hibachi grill, Double Fulgor Milano ovens and Hestan wine refrigeration. Generous surfaces invite abundant platters and conversation while the outdoor kitchen complete with a sink, two gas burners and a large Green Egg extends the experience into the garden. Large impact windows bring garden views into the bedrooms and living spaces keeping the surrounding greenery in sight throughout the home. The home balances open spaces for entertaining with the privacy of a personal escape. Its setting on Eagle Avenue, a beautiful wide street with sidewalks seldom found in Key West, completes a home with a distinctly Mediterranean sensibility and an unmistakable island soul.

3 Beds ⋅ 2 Baths ⋅ 621869 MLS

Beyond the doors of 3821 Eagle Avenue, a private courtyard evokes the intimacy of a Tuscan retreat. Cascading vines, sculptural bougainvillea and lush greenery frame the 29x15 pool while a shaded terrace invites long lunches that linger into evening. Expansive folding glass doors connect the interiors to the outdoors allowing gatherings to flow naturally from kitchen to poolside. Warm wood cabinetry and a substantial waterfall edge island anchor a kitchen that knows culinary appointed with a Wolf induction range, Wolf hibachi grill, Double Fulgor Milano ovens and Hestan wine refrigeration. Generous surfaces invite abundant platters and conversation while the outdoor kitchen complete with a sink, two gas burners and a large Green Egg extends the experience into the garden. Large impact windows bring garden views into the bedrooms and living spaces keeping the surrounding greenery in sight throughout the home. The home balances open spaces for entertaining with the privacy of a personal escape. Its setting on Eagle Avenue, a beautiful wide street with sidewalks seldom found in Key West, completes a home with a distinctly Mediterranean sensibility and an unmistakable island soul.

3821 Eagle Ave, Key West

$2,199,000

Fully Furnished Tropical Keys Oasis - Waterfront Luxury Living Just unpack and start living the island life in this completely renovated, one-of-a-kind tropical oasis that rivals any luxury 5-star resort. Relax in the sparkling pool surrounded by lush, mature landscaping, including coconut palms, banana trees, mango trees and a Hass avocado tree. Vibrant bougainvillea archways create a stunning entry to one of the most exquisitely landscaped homes on the island. Outdoor living here is elevated to the next level and is perfect for entertaining. Enjoy 60 feet of waterfront with an expansive maintenance-free deck, a 15,000-lb boat lift and a drop dock perfect for swimming in the lagoon or launching kayaks. Inside, discover a beautiful 4-bedroom, 2.5-bath home featuring a chef's kitchen with a 6-burner gas stove, double farm sink, all-new stainless-steel appliances and a massive center island with abundant storage, so you can enjoy everyday luxury living. Gorgeous tile flooring flows throughout. The first floor offers three guest bedrooms, a stylishly renovated bath, a convenient half bath and a full laundry room with gas dryer. The spacious living room opens through triple sliding glass pocket doors to a screened porch secluded by palms, bringing your indoor living outdoors in the winter and ideal for morning coffee or dining al fresco year-round. Upstairs, the primary suite is a private retreat with panoramic water views, a custom walk-in closet and a spa-inspired bathroom with an oversized shower featuring six body jets, a handheld sprayer and a ceiling-mounted rain shower. Dual vanities and a lighted mirror complete this luxurious sanctuary. Additional features include: - Brand-new impact windows and doors throughout - Metal roof - Fully fenced backyard, perfect for pets and privacy - 300 sq. ft. storage room with impact windows and doors - Irrigation system - Propane gas - Endless on-demand gas water heater - And so much more!

4 Beds ⋅ 3 Baths ⋅ 621763 MLS

Fully Furnished Tropical Keys Oasis - Waterfront Luxury Living Just unpack and start living the island life in this completely renovated, one-of-a-kind tropical oasis that rivals any luxury 5-star resort. Relax in the sparkling pool surrounded by lush, mature landscaping, including coconut palms, banana trees, mango trees and a Hass avocado tree. Vibrant bougainvillea archways create a stunning entry to one of the most exquisitely landscaped homes on the island. Outdoor living here is elevated to the next level and is perfect for entertaining. Enjoy 60 feet of waterfront with an expansive maintenance-free deck, a 15,000-lb boat lift and a drop dock perfect for swimming in the lagoon or launching kayaks. Inside, discover a beautiful 4-bedroom, 2.5-bath home featuring a chef's kitchen with a 6-burner gas stove, double farm sink, all-new stainless-steel appliances and a massive center island with abundant storage, so you can enjoy everyday luxury living. Gorgeous tile flooring flows throughout. The first floor offers three guest bedrooms, a stylishly renovated bath, a convenient half bath and a full laundry room with gas dryer. The spacious living room opens through triple sliding glass pocket doors to a screened porch secluded by palms, bringing your indoor living outdoors in the winter and ideal for morning coffee or dining al fresco year-round. Upstairs, the primary suite is a private retreat with panoramic water views, a custom walk-in closet and a spa-inspired bathroom with an oversized shower featuring six body jets, a handheld sprayer and a ceiling-mounted rain shower. Dual vanities and a lighted mirror complete this luxurious sanctuary. Additional features include: - Brand-new impact windows and doors throughout - Metal roof - Fully fenced backyard, perfect for pets and privacy - 300 sq. ft. storage room with impact windows and doors - Irrigation system - Propane gas - Endless on-demand gas water heater - And so much more!

27385 Saint Lucie Ln, Ramrod

$2,199,000

Enjoy endless ocean views from this charming Florida Keys waterfront retreat. Sitting on the edge of the Atlantic just one house in from open water, this stilted 2-bedroom, 2.5-bath CBS home also offers possible 3-bedroom flexibility and is a true boater's dream with 85 feet of waterfront frontage, concrete seawall, a 13,500 lb boat lift, deep-water dockage, and instant access to the Atlantic. The channel is slightly right as soon as you come out of the canal, placing you just minutes from Sombrero Light and some of the best boating, fishing, and diving the Keys have to offer. The home features a spacious, light-filled layout with a large living area, generous waterside windows, and sliding glass doors that frame the ocean views and open to east-facing covered porches on two levels. Inside, you'll find a comfortable eat-in kitchen with stainless steel appliances, abundant natural light, generous storage, walk-in closets, and impact windows and doors for added peace of mind. Outdoor living is the highlight, with a new waterfront pool and hot tub, expansive deck, large waterside porch, fenced yard, tropical landscaping, and multiple spaces to relax, dine, entertain, or simply take in the ocean breeze. Additional features include a garage, CBS construction, metal roof, travertine-paved driveway, inviting covered patio areas, and a large front yard offering flexibility for additional parking, boat/RV storage, or future use. The home is also available furnished, offering added convenience for those ready to start enjoying the Keys lifestyle right away. With open water just moments away, this Marathon property offers the perfect blend of boating, ocean views, poolside relaxation, and laid-back Keys living. This one is a must-see to truly appreciate.

2 Beds ⋅ 3 Baths ⋅ 620384 MLS

Enjoy endless ocean views from this charming Florida Keys waterfront retreat. Sitting on the edge of the Atlantic just one house in from open water, this stilted 2-bedroom, 2.5-bath CBS home also offers possible 3-bedroom flexibility and is a true boater's dream with 85 feet of waterfront frontage, concrete seawall, a 13,500 lb boat lift, deep-water dockage, and instant access to the Atlantic. The channel is slightly right as soon as you come out of the canal, placing you just minutes from Sombrero Light and some of the best boating, fishing, and diving the Keys have to offer. The home features a spacious, light-filled layout with a large living area, generous waterside windows, and sliding glass doors that frame the ocean views and open to east-facing covered porches on two levels. Inside, you'll find a comfortable eat-in kitchen with stainless steel appliances, abundant natural light, generous storage, walk-in closets, and impact windows and doors for added peace of mind. Outdoor living is the highlight, with a new waterfront pool and hot tub, expansive deck, large waterside porch, fenced yard, tropical landscaping, and multiple spaces to relax, dine, entertain, or simply take in the ocean breeze. Additional features include a garage, CBS construction, metal roof, travertine-paved driveway, inviting covered patio areas, and a large front yard offering flexibility for additional parking, boat/RV storage, or future use. The home is also available furnished, offering added convenience for those ready to start enjoying the Keys lifestyle right away. With open water just moments away, this Marathon property offers the perfect blend of boating, ocean views, poolside relaxation, and laid-back Keys living. This one is a must-see to truly appreciate.

1400 W 63rd St, Marathon

$2,199,000

On a quiet lane in Old Town, this classic Conch home offers a setting where life feels just a little slower and a lot more enjoyable. From the moment you step inside, the home draws you outward, where indoor living blends naturally with the surrounding outdoor spaces. The heart of the home is built around entertaining. The living area, kitchen, and dining space come together in a way that encourages gathering, while the outdoor covered patio is perfect for dining or lounging creating a natural extension for everything from slow mornings to late evenings. Step outside and the pace shifts. Sitting on a large L shaped lot, the pool becomes the centerpiece, surrounded by deck space, greenery, and just enough privacy to make it feel like your own little corner of the island. The inviting primary suite is a peaceful retreat, featuring vaulted ceilings and French doors that open directly to the pool. Upstairs, two additional bedrooms and a shared bath provide comfortable separation, while the detached poolside cottage, with its own bath and outdoor shower offers flexible space for guests, a workspace, or added privacy. A convenient powder room is also located just off the kitchen. Dade County pine walls, wood floors, and tall ceilings bring warmth and authenticity, giving the home a sense of history without ever feeling heavy. It is comfortable, inviting, and easy to live in, the kind of home that makes everyday moments feel just a little more special. Quiet, central, and layered with history, 1109 Stump Lane stands as one of Old Town's most compelling hidden opportunities, a rare chance to own a truly private retreat in the heart of Key West.

3 Beds ⋅ 4 Baths ⋅ 619404 MLS

On a quiet lane in Old Town, this classic Conch home offers a setting where life feels just a little slower and a lot more enjoyable. From the moment you step inside, the home draws you outward, where indoor living blends naturally with the surrounding outdoor spaces. The heart of the home is built around entertaining. The living area, kitchen, and dining space come together in a way that encourages gathering, while the outdoor covered patio is perfect for dining or lounging creating a natural extension for everything from slow mornings to late evenings. Step outside and the pace shifts. Sitting on a large L shaped lot, the pool becomes the centerpiece, surrounded by deck space, greenery, and just enough privacy to make it feel like your own little corner of the island. The inviting primary suite is a peaceful retreat, featuring vaulted ceilings and French doors that open directly to the pool. Upstairs, two additional bedrooms and a shared bath provide comfortable separation, while the detached poolside cottage, with its own bath and outdoor shower offers flexible space for guests, a workspace, or added privacy. A convenient powder room is also located just off the kitchen. Dade County pine walls, wood floors, and tall ceilings bring warmth and authenticity, giving the home a sense of history without ever feeling heavy. It is comfortable, inviting, and easy to live in, the kind of home that makes everyday moments feel just a little more special. Quiet, central, and layered with history, 1109 Stump Lane stands as one of Old Town's most compelling hidden opportunities, a rare chance to own a truly private retreat in the heart of Key West.

1109 Stump Ln, Key West

$2,199,000

Seller Financing Available | Pre-Construction Waterfront Retreat | Deep Water | Sunrise Views Located right across from the island of Boot Key, this exceptional pre-construction offering combines protected deep-water living, open-water views, and one of the most desirable boating locations in Marathon. Explore scenic kayak trails for beginners and advanced paddlers, surrounded by rich nature and wildlife where dolphins and manatees are frequently seen. The property faces east for breathtaking sunrises, while Boot Key provides natural protection during storms—creating an ideal, secure harbor environment. With approx 60 feet of deep-water dockage, enjoy ample space for large or multiple vessels, excellent maneuverability, and direct access to world-class boating. Inside the harbor, convenience is unmatched with 5 restaurants and 3 gas docks just minutes away. Commencing soon on this with construction, the custom home is designed with modern coastal style and true Keys practicality. The residence will feature 3 bedrooms and 2.5 bathrooms, offering elevated living spaces perfectly oriented toward panoramic Boot Key Harbor views. Whether you're a dedicated boater, nature lover, investor, or seeking a peaceful Keys escape, this rare property delivers the ultimate blend of location, protection, and lifestyle. Seller will finance with half down!

3 Beds ⋅ 3 Baths ⋅ 617567 MLS

Seller Financing Available | Pre-Construction Waterfront Retreat | Deep Water | Sunrise Views Located right across from the island of Boot Key, this exceptional pre-construction offering combines protected deep-water living, open-water views, and one of the most desirable boating locations in Marathon. Explore scenic kayak trails for beginners and advanced paddlers, surrounded by rich nature and wildlife where dolphins and manatees are frequently seen. The property faces east for breathtaking sunrises, while Boot Key provides natural protection during storms—creating an ideal, secure harbor environment. With approx 60 feet of deep-water dockage, enjoy ample space for large or multiple vessels, excellent maneuverability, and direct access to world-class boating. Inside the harbor, convenience is unmatched with 5 restaurants and 3 gas docks just minutes away. Commencing soon on this with construction, the custom home is designed with modern coastal style and true Keys practicality. The residence will feature 3 bedrooms and 2.5 bathrooms, offering elevated living spaces perfectly oriented toward panoramic Boot Key Harbor views. Whether you're a dedicated boater, nature lover, investor, or seeking a peaceful Keys escape, this rare property delivers the ultimate blend of location, protection, and lifestyle. Seller will finance with half down!

1252 24th St, Marathon

$2,195,000

Two residences, two private pools, and 75 feet of dockage--an inviting combination of space, privacy, and waterfront living in Key Colony Beach. This full duplex brings family and friends together while maintaining the independence of two separate homes. Each offers two bedrooms, two bathrooms, and a generous 1,075 square feet, plus a private entrance, carport, and laundry. Inside, Old Florida character meets modern comfort. Vaulted wood ceilings grace the living, dining, and kitchen areas, while original terrazzo floors in one residence offer a nostalgic nod to the Keys of yesteryear. Updates in 2024-2025 include refreshed kitchens and fully renovated bathrooms with a modern coastal feel. Both backyards have been transformed into private tropical retreats, each with its own pool, tiki hut, bar/cabana area, and 37.5 feet of dockage. A connecting gate keeps the outdoor spaces private or opens them for gatherings. Oceanside boating with convenient Gulf access via nearby Vaca Cut. Ideal for extended families and friends sharing a Keys getaway, with room to enjoy one residence while renting the other--or rent both when away. Introduced to the vacation rental market in early 2025, the property has generated and booked $167,000 in 2026 gross rental revenue, with six weeks reserved for owner use. And then there's the location. Just a two-minute walk to Sunset Park, with restaurants and other island amenities an easy walk or bike ride away. A property that brings together the best of Keys living--time on the water, space for family and friends, and the flexibility to enjoy it on your own terms.

4 Beds ⋅ 4 Baths ⋅ 621805 MLS

Two residences, two private pools, and 75 feet of dockage--an inviting combination of space, privacy, and waterfront living in Key Colony Beach. This full duplex brings family and friends together while maintaining the independence of two separate homes. Each offers two bedrooms, two bathrooms, and a generous 1,075 square feet, plus a private entrance, carport, and laundry. Inside, Old Florida character meets modern comfort. Vaulted wood ceilings grace the living, dining, and kitchen areas, while original terrazzo floors in one residence offer a nostalgic nod to the Keys of yesteryear. Updates in 2024-2025 include refreshed kitchens and fully renovated bathrooms with a modern coastal feel. Both backyards have been transformed into private tropical retreats, each with its own pool, tiki hut, bar/cabana area, and 37.5 feet of dockage. A connecting gate keeps the outdoor spaces private or opens them for gatherings. Oceanside boating with convenient Gulf access via nearby Vaca Cut. Ideal for extended families and friends sharing a Keys getaway, with room to enjoy one residence while renting the other--or rent both when away. Introduced to the vacation rental market in early 2025, the property has generated and booked $167,000 in 2026 gross rental revenue, with six weeks reserved for owner use. And then there's the location. Just a two-minute walk to Sunset Park, with restaurants and other island amenities an easy walk or bike ride away. A property that brings together the best of Keys living--time on the water, space for family and friends, and the flexibility to enjoy it on your own terms.

240-250 11th St, Key Colony

$2,195,000

This stunning 5-bedroom, 5-bathroom fortress of a home, completely reimagined and rebuilt in 2023, offers 3,062 sq. ft. of luxurious living space on a 5,040 sq. ft. lot. Featuring 9-foot ceilings, custom wood cabinetry, porcelain wood-look tile and luxury vinyl flooring, the home showcases exceptional craftsmanship throughout. The chef's kitchen is a true centerpiece, featuring an impressive 17-foot island with seating for eight, professional grade appliances, a 36-inch gas range with vented hood, and a wine refrigerator. The spacious primary suite features a walk-in closet and a spa inspired wet room with dual showerheads, a clawfoot soaking tub, and dual vanities. Additional conveniences include laundry areas on both floors and abundant storage, including attic and under-home space. Built with durability and efficiency in mind, the home features impact resistant windows, spray foam insulation, and a double strapped aluminum standing seam roof. The backyard offers an inviting outdoor retreat, highlighted by a heated pool and traditional thatched chickee hut, perfect for relaxing or entertaining in true Key West style. From the moment you step inside, you'll appreciate the striking architectural symmetry, exquisite craftsmanship, and meticulous attention to detail that make this exceptional Key West residence truly one of a kind. *Please note that some photos have been digitally staged or altered*

5 Beds ⋅ 5 Baths ⋅ 621768 MLS

This stunning 5-bedroom, 5-bathroom fortress of a home, completely reimagined and rebuilt in 2023, offers 3,062 sq. ft. of luxurious living space on a 5,040 sq. ft. lot. Featuring 9-foot ceilings, custom wood cabinetry, porcelain wood-look tile and luxury vinyl flooring, the home showcases exceptional craftsmanship throughout. The chef's kitchen is a true centerpiece, featuring an impressive 17-foot island with seating for eight, professional grade appliances, a 36-inch gas range with vented hood, and a wine refrigerator. The spacious primary suite features a walk-in closet and a spa inspired wet room with dual showerheads, a clawfoot soaking tub, and dual vanities. Additional conveniences include laundry areas on both floors and abundant storage, including attic and under-home space. Built with durability and efficiency in mind, the home features impact resistant windows, spray foam insulation, and a double strapped aluminum standing seam roof. The backyard offers an inviting outdoor retreat, highlighted by a heated pool and traditional thatched chickee hut, perfect for relaxing or entertaining in true Key West style. From the moment you step inside, you'll appreciate the striking architectural symmetry, exquisite craftsmanship, and meticulous attention to detail that make this exceptional Key West residence truly one of a kind. *Please note that some photos have been digitally staged or altered*

2827 Harris Ave, Key West

$2,195,000

RARE RUNWAY-TO-REEF LIVING Fly in. Boat out. Live the Florida Keys lifestyle few properties can offer. At 86 S Airport Drive on Summerland Key, aviation and boating come together in one exceptional property. This CBS 3-bedroom, 3-bath home sits directly on the runway and alongside a flow-through canal, offering the rare convenience of keeping your plane and boat close to home. Built for island living, the home features a durable metal roof and impact windows. Outside, a waterfront tiki invites you to unwind after a day on the water, while a 20,000-pound boat lift, commercial ice maker, and deep draft make this a compelling base for serious boaters. Follow the well-marked channel to the ocean, or head toward the Gulf via Kemp Channel. Explore offshore waters, cruise the backcountry, or spend an afternoon relaxing on the sandbars at Snipes or Marvin Key. Here, your next adventure can begin in the air or on the water. For the pilot who loves to fish, the fisherman who loves to fly, or anyone drawn to the freedom of both, this is more than a home - it's a distinctive way to experience the Florida Keys. Runway access and flow-through canal boating at one address make this a truly rare find! See the additional features on the Document tab. Airport information is available at: https://www.summerlandkeyairport.com/ Note: 2022 40' WorldCat is also for sale (separately).

3 Beds ⋅ 3 Baths ⋅ 621715 MLS

RARE RUNWAY-TO-REEF LIVING Fly in. Boat out. Live the Florida Keys lifestyle few properties can offer. At 86 S Airport Drive on Summerland Key, aviation and boating come together in one exceptional property. This CBS 3-bedroom, 3-bath home sits directly on the runway and alongside a flow-through canal, offering the rare convenience of keeping your plane and boat close to home. Built for island living, the home features a durable metal roof and impact windows. Outside, a waterfront tiki invites you to unwind after a day on the water, while a 20,000-pound boat lift, commercial ice maker, and deep draft make this a compelling base for serious boaters. Follow the well-marked channel to the ocean, or head toward the Gulf via Kemp Channel. Explore offshore waters, cruise the backcountry, or spend an afternoon relaxing on the sandbars at Snipes or Marvin Key. Here, your next adventure can begin in the air or on the water. For the pilot who loves to fish, the fisherman who loves to fly, or anyone drawn to the freedom of both, this is more than a home - it's a distinctive way to experience the Florida Keys. Runway access and flow-through canal boating at one address make this a truly rare find! See the additional features on the Document tab. Airport information is available at: https://www.summerlandkeyairport.com/ Note: 2022 40' WorldCat is also for sale (separately).

86 S Airport Dr, Summerland

$2,195,000

Welcome to Pen Key Club -- Islamorada's most private and prestigious gated bayfront enclave -- where legacy living meets effortless island luxury. This spacious Key West-inspired residence offers the rare combination of privacy, scale, and resort-style amenities that families and discerning buyers seek but seldom find in the Keys. Wrapped in mature tropical landscaping and timeless architectural charm, the home lives beautifully indoors and out. Sunlit interiors flow to wide wraparound porches, garden-view patios, and multiple gathering spaces designed for entertaining, relaxing, and savoring the island's signature golden sunsets. With three large bedrooms, generous living areas, and inviting outdoor retreats, the home provides the comfort and flexibility ideal for full-time living, seasonal escapes, or multigenerational enjoyment. Pen Key Club is one of Islamorada's most exclusive communities, offering residents a curated suite of amenities: a resort-style pool, a protected marina, kayak launch, and a stunning owners-only sunset point. The protected marina delivers direct access to world-class sport fishing and boating, while full-time on-site property management ensures seamless peace of mind whether you're home or away. Perfectly positioned in the heart of Islamorada, the property offers quick access to fine dining, boutique shopping, and the legendary waters that define the sport fishing capital of the world. This is more than a home -- it's a private retreat, a long-term investment, and a rare opportunity to own within one of the Keys' most coveted communities. Experience the unmatched blend of luxury, leisure, and privacy that makes Pen Key Club truly exceptional.

3 Beds ⋅ 4 Baths ⋅ 621487 MLS

Welcome to Pen Key Club -- Islamorada's most private and prestigious gated bayfront enclave -- where legacy living meets effortless island luxury. This spacious Key West-inspired residence offers the rare combination of privacy, scale, and resort-style amenities that families and discerning buyers seek but seldom find in the Keys. Wrapped in mature tropical landscaping and timeless architectural charm, the home lives beautifully indoors and out. Sunlit interiors flow to wide wraparound porches, garden-view patios, and multiple gathering spaces designed for entertaining, relaxing, and savoring the island's signature golden sunsets. With three large bedrooms, generous living areas, and inviting outdoor retreats, the home provides the comfort and flexibility ideal for full-time living, seasonal escapes, or multigenerational enjoyment. Pen Key Club is one of Islamorada's most exclusive communities, offering residents a curated suite of amenities: a resort-style pool, a protected marina, kayak launch, and a stunning owners-only sunset point. The protected marina delivers direct access to world-class sport fishing and boating, while full-time on-site property management ensures seamless peace of mind whether you're home or away. Perfectly positioned in the heart of Islamorada, the property offers quick access to fine dining, boutique shopping, and the legendary waters that define the sport fishing capital of the world. This is more than a home -- it's a private retreat, a long-term investment, and a rare opportunity to own within one of the Keys' most coveted communities. Experience the unmatched blend of luxury, leisure, and privacy that makes Pen Key Club truly exceptional.

33 Pen, Islamorada

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