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luxury houses with sea view for sale Monroe County, United States

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50

House Marathon (United States)

Experience the Florida Keys lifestyle on a double lot in Marathon's sought-after Little Venice. This 2 bed/2 bath waterfront retreat boasts open-water views, 100' of concrete dockage with a 20,000 lb boat lift, and a resort-style outdoor living area built for entertaining. The backyard features a pool(heated or chilled), hot tub, poolside cabana with sink and refrigerator, mature tropical landscaping, and expansive decks for soaking up sunsets or unwinding after a day on the water. Practical boating amenities include power, water, lighting, and a fish-cleaning station; RV hookups and ample parking accommodate guests and all your toys. Inside, cathedral ceilings create a bright, airy living space while every bedroom enjoys its own private bath for comfort and privacy. Notable updates and systems: newer metal roof, tankless water heater, large laundry/utility room, and abundant storage. Located in a weekly-rental zone, the property offers strong income potential as a primary home, vacation getaway, or investment. From open-water vistas to thoughtful outdoor spaces, this home captures everything the Keys have to offer.

… 
$1,499,000
103
2bedrooms
2bathrooms
land 486

By Ocean Sotheby's International Realty

50
Video

House Islamorada (United States)

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

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$3,950,000
4bedrooms
5bathrooms

By Ocean Sotheby's International Realty

16

House with pool and garden Key Largo (United States)

Wonderfully refreshed! Beautifully decorated four bedroom waterfront Sunrise Cay home. Far reaching views from the second floor of the bay and ocean. Ocean breezes from the front travel through to the back deck for sunset views. The primary suite has expansive water views. The very large screened lower level accommodates all the needs of active boaters and fishing enthusiasts with an extensive tackle room and substantial two car garage. Positioned on a 19,500 square feet large lot and built with over 5,000 square feet of finished living space, this home offers wonderful space, PRIME location, ample sunlight from both directions. The perfect home to enjoy the gorgeous natural beauty of Ocean Reef! 72 ft of canal front for a 42 ft boat on a 38 foot dock.

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$9,900,000
467
4bedrooms
4bathrooms
land 1,821

By Ocean Reef Club Sotheby's International Realty

44

House Marathon (United States)

Fully licensed 7 day vacation rental property now offered at Bonefish Yacht Club Townhomes, a Middle Keys premiere boating community cloistered around the 50 slip Bonefish Marina. Resort style living in this sought after oceanfront complex of only 34 homes. Conveys with A-16, a deep water, direct ocean access, 40' liveaboard boat slip. Other amenities featured are; swimming pool, tiki, meticulously maintained tropical landscaping, tennis and private beach access. Unparalleled views of the marina and Key Colony Channel. Two story townhome with covered parking and secure angler's room on the lower level, kitchen, living, dining on the main level and two spacious bedrooms with full baths on the third floor. Private, open air balconies to enjoy both sunrise and sunset. Concrete construction, impact windows and metal roof. Excellent for a full time residence, Keys fishing getaway or investment property as a income producing weekly rental. A true pleasure to show.

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$1,250,000
133
2bedrooms
3bathrooms
land 121

By Ocean Sotheby's International Realty

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50

House Marathon (United States)

Discover the potential of this concrete constructed, waterfront pool home tucked away on tranquil Flamingo Island. Offering the ideal opportunity to renovate, personalize, and create your own Florida Keys retreat, this property features three bedrooms, two bathrooms, and nearly 1,300 square feet of interior living space. More than 600 square feet of screened porches invite relaxed indoor-outdoor living, while over 500 square feet of enclosed storage provides valuable additional space for boating gear, bicycles, fishing equipment, and more. Boaters will appreciate the newly constructed 60-foot wood dock, completed in 2025, along with excellent deep-water access through nearby Sister Creek. After a day on the water, unwind beside the concrete pool or enjoy the peaceful island surroundings. Additional improvements include a metal roof installed in 2020 and termite tenting completed in 2025 by Hammerhead Termite Control. Located behind the Florida Keys Golf and Country Club, Flamingo Island is a quiet, dog-friendly waterfront neighborhood close to everything Marathon has to offer. Take the golf cart to Sombrero Beach, Publix, nearby restaurants, and local conveniences. With superior concrete construction, substantial dockage, a private pool, generous outdoor living areas, and an inviting waterfront setting, this fixer-upper presents a rare blank canvas ready to be transformed into your ideal Keys escape.

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$1,295,000
115
3bedrooms
2bathrooms
land 607

By Ocean Sotheby's International Realty

50
Video

House Key Largo (United States)

Welcome to 103 Andros Road, a stunning oceanfront estate nestled in the heart of Ocean Reef. This exceptional home is the perfect retreat for family relaxation, offering a serene escape from the demands of everyday life. Boasting 4,870 sq. ft. of living space, this 4-bedroom, 5 full bath, and 2 half bath residence is designed to embrace the breathtaking water views. The home's traditional yet sophisticated exterior complements its modern, minimalist interior, featuring clean lines and a comfortable atmosphere. A standout feature is the impressive infinity pool with glass walls, dual fire globes, and a 16' cascading waterfall, all overlooking the ocean. The open-concept living area flows seamlessly into the kitchen, dining, and bar spaces, with sliding glass doors that disappear into the walls to create an expansive indoor-outdoor experience. On the main floor, three beautifully appointed guest suites provide ample space and privacy. The entire second floor is dedicated to the master suite, complete with wrap-around glass walls opening to a private balcony with panoramic ocean views. Every detail in this home has been thoughtfully curated with architectural touches that elevate its elegance.

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$27,750,000
452
4bedrooms
7bathrooms
land 1,295

By Ocean Reef Club Sotheby's International Realty

50

Seaside house with pool and terrace Key Colony Beach (United States)

Motivated Sellers want you to experience the sweeping ocean views and breathtaking sunsets, from both floors of this beautifully updated oceanfront residence in Key Colony Beach--the gem of the Florida Keys. The spacious primary suite features an extended living area on the enclosed balcony with amazing blue water & sunset views, a custom bath, and generous walk-in closet. Two large guest bedrooms offer comfort and privacy for family or visitors. The gourmet kitchen boasts abundant cabinetry, stunning granite countertops, and opens to a light-filled living and dining area complete with a wet bar and panoramic ocean vistas--perfect for entertaining. This home suits any lifestyle: a high-performing vacation rental, a seasonal retreat for snowbirds, or a full-time residence in a meticulously maintained community of just 31 condos and townhomes. Enjoy resort-style amenities including a large oceanfront pool surrounded by expansive sun decks, a fishing pier with breathtaking sunset views, grilling and private lounging areas, covered parking garage, bike and kayak storage, plus guest parking, shuffleboard, and tennis/pickleball courts. Ideally located near marinas, restaurants, shopping, and local attractions, your island dream awaits in paradise.

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$844,000
179
3bedrooms
3bathrooms

By Ocean Sotheby's International Realty

50

Seaside house with pool Duck Key (United States)

Experience refined oceanfront living on sought-after Duck Key. This double lot estate offers 138 feet of protected deepwater dockage, complete with a solid concrete seawall designed to accommodate a sportfishing yacht, multiple center consoles, and all of your waterfront lifestyle needs. A true boater's paradise, this property offers both privacy and exceptional access to the Atlantic Ocean. The fully remodeled residence is constructed of concrete with a new roof. Inside, seven spacious bedrooms and six bathrooms provide ample accommodations for family and guests. Coastal-inspired interiors feature wood-look tile flooring throughout, woven statement light fixtures, and soaring ceilings with exposed beams and pecky cypress accents. Expansive impact windows and doors frame sweeping ocean views, bringing natural light into nearly every room. The gourmet kitchen anchors the main living space as the heart of the home, with a striking 12' island that creates the perfect setting for gatherings. Outfitted with top-of-the-line appliances, this space is equally suited for everyday living with family or hosting unforgettable evenings of entertaining. Spa-like marble bathrooms further elevate the home, blending comfort with luxury. Designed for both style and function, the property also offers a rare 4+ car garage and abundant storage. Outdoors, a sparkling pool invites afternoons in the sun, while the expansive double lot offers unmatched opportunities for expansion. Whether envisioning a private guest house, a tennis or pickleball court, or exploring the option to build and sell, this rare property provides endless possibilities for both personal enjoyment and investment potential—an uncommon luxury in the Florida Keys. Balancing modern sophistication with coastal simplicity, this sanctuary captures the essence of waterfront living from sunrise over the Atlantic to evenings by the water, in one of the most desirable neighborhoods in the Florida Keys.

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$7,199,000
372
7bedrooms
6bathrooms
land 3,076

By Ocean Sotheby's International Realty

48
Video

House Key Largo (United States)

Experience the pinnacle of coastal luxury in this spectacular 4-bedroom, 4.5-bathroom estate, offering 3,454 square feet of light-filled living space on an oversized 26,450-square-foot lot. Commanding 170 feet of seawall, the property delivers unobstructed views across a picturesque water basin. This prime location provides ample deep-water maneuvering room for multiple large vessels, making it a true paradise for avid boaters. Exceptional curb appeal welcomes you, featuring a paved driveway and lighted landscaping. Inside, architectural grandeur meets effortless comfort. The living room features an inviting fireplace and flows seamlessly into an adjacent den. The kitchen is a culinary haven, with a generous center island that seats four. Positioned as a private sanctuary, the master suite boasts soaring ceilings, oversized walk-in closet, and an exclusive covered patio. The spa-like master bath looks directly onto a dedicated orchid lanai. Outdoors, an entertainer’s paradise awaits: a large covered living area transitions into a fully equipped summer kitchen—complete with a built-in grill and refrigerator drawers—all framed by lush, tropical landscaping and a sparkling heated pool. A spacious three-car garage completes this unparalleled waterfront retreat.

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$13,800,000
321
4bedrooms
5bathrooms
land 10,703.9ha

By Ocean Reef Club Sotheby's International Realty

50

House Key West (United States)

Experience the quintessential island lifestyle in this stunning waterfront townhome at Flagler's Landing, where Gulf views meet the convenience of a central Key West location. This elevated residence offers approximately 1,387 sq ft of living space with open Gulf views from the main living areas, private balcony, and both upstairs bedrooms. The main level is designed for effortless entertaining, featuring an open-concept design with spacious living and dining areas. The gourmet kitchen is anchored by a custom coral stone island with seating for six, equipped with custom cabinetry, under-cabinet lighting, premium GE appliances, a six-burner range, and a brand-new refrigerator. Warm bamboo flooring, recessed lighting, and a wide waterfront balcony accessed through sliding glass doors create an inviting atmosphere for indoor-outdoor living, perfect for enjoying sunsets and ocean breezes. A powder bath completes this level. A spiral staircase leads to the second level, where the hallway features built-in bookshelves and access to an additional front-facing balcony. Both serene bedrooms enjoy expansive waterfront views and walk-in closets. The primary suite and guest bedroom provide a relaxing coastal setting for family or visitors, complemented by a full bath featuring a glass walk-in shower, a large vanity, and a jacuzzi-style tub. Additional features include central A/C, ground-level covered private parking, dedicated storage, a laundry area, and a charming ground-floor brick patio. For boating enthusiasts, the property includes a private shallow-draft boat slip suitable for an approximately 24 ft boat, enjoyable any season all year. Residents also enjoy community access to a heated concrete pool. Perfectly situated near beaches, restaurants, shopping, and marinas, this home provides a unique opportunity to own a premier piece of paradise in an exclusive enclave where properties rarely become available.

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$1,375,000
129
2bedrooms
2bathrooms

By Ocean Sotheby's International Realty

50
Video

Seaside house with pool and garden Marathon (United States)

Enter the bougainvillea-lined gates of Casa Feliz, a private oceanfront retreat on Grassy Key with expansive water views, white sand beach, and a true resort-style experience in the Florida Keys. An exceptional investment opportunity, Casa Feliz is a strong producing vacation rental with rental history and future bookings already in place. Set on over 24,000 square feet of lush grounds with mature landscaping, fruit trees, fresh herbs, and .29 acres of bay bottom, this exceptional estate is designed for both relaxation and entertaining. A 148-foot observation dock invites kayaking, paddleboarding, fishing, and endless enjoyment of marine life, while the unique orientation captures both breathtaking sunrise and sunset views over the water, a rare and coveted feature in the Keys. Outdoor living is elevated with a resort-style saltwater pool featuring cascading waterfalls, spillover spa, and fully equipped poolside cabana complete with wet bar, refrigerator, ice maker, and cooking area. A fire table and beachside fire pit create the ultimate setting for entertaining or unwinding beneath the stars. Completely renovated down to the studs in 2022, the three-story residence was thoughtfully redesigned to maximize sweeping ocean views from nearly every room. Offering four custom bedroom suites, each with private en-suite bath, the home comfortably accommodates guests in luxury. The top-floor penthouse suite features a private balcony, 180-degree ocean views, custom 96-inch circular bed, and kitchenette with coffee station. Expansive accordion impact glass doors seamlessly blend indoor and outdoor living throughout. The gourmet kitchen showcases Café appliances, induction cooktop, quartz countertops, mosaic tile backsplash, wine cooler, glass shelving, and multiple dining areas ideal for hosting. Additional highlights include a movie theater, library loft, Control4 smart technology, custom millwork, local artist mural, and more. Discover why Grassy Key is the place to be.

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$3,495,000
226
4bedrooms
4bathrooms
land 3,440

By Ocean Sotheby's International Realty

50

Property Key Largo (United States)

Discover effortless Florida Keys living at Fisherman's Cove, an exclusive private residence club overlooking Blackwater Sound in Key Largo. This 1/8 fractional ownership offers approximately 2,300 square feet of beautifully appointed living space with three spacious bedrooms, three full bathrooms, and a recently renovated interior blending contemporary finishes with relaxed island style. Designed for both comfort and entertaining, the residence features a fully equipped gourmet kitchen with bar seating and an expansive private balcony ideal for taking in the waterfront surroundings. Ownership extends well beyond the residence itself, with access to an impressive collection of amenities including a resort-style pool with three private cabanas, rooftop owners' deck, concierge and housekeeping services, and two owners-only boats, a 26' Sea Fox and 24' Contender, for enjoying the waters of the Florida Keys. Located above Jimmy Johnson's Big Chill, Fisherman's Cove places dining, entertainment, boating, and waterfront relaxation all within steps of your residence. Owners enjoy flexible year-round use, typically 5-7 weeks annually, with opportunities for additional stays based on availability. Fisherman's Cove is a private residence club with privileges reserved exclusively for owners. Rentals are not permitted. This is a 1/8 Fractional Ownership Opportunity.

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$315,000
204
3bedrooms
3bathrooms

By Ocean Sotheby's International Realty

24

House with terrace Key Colony Beach (United States)

Nicely renovated 2BD/2BA waterfront half-duplex in vibrant Key Colony Beach, offering impressive water views from both the front and back of the home. Stilted concrete construction, metal roof and impact windows make the insurances extremely affordable. Wake up to glowing sunrises over the water and wind down with color-soaked Keys sunsets from your private balconies perfect for morning coffee, sunset cocktails, and effortless indoor-outdoor living. A deep-water pier-style dock accommodates boats up to 40 ft giving you instant access to world-class fishing, diving, and boating. Designed for adventure and convenience, the property includes parking for up to 3 vehicles, 2 covered spaces beneath the home and an additional uncovered driveway space ideal for extra parking or a boat trailer. A dedicated tackle room keeps gear organized and ready for your next trip offshore. Everything you love about Key Colony Beach is within easy walking distance, Sunset Park for oceanfront strolls and nightly sunsets, the Key Colony Beach Golf Course, tennis and pickleball courts, the Cabana Club with oceanfront pool and beach access (membership-based), and the Key Colony Beach Marina. Restaurants, walking paths, and the island's friendly, laid-back atmosphere are all right at your doorstep. With 7-day rentals permitted, this property offers excellent vacation-rental potential in one of the most desirable waterfront, boating communities in the Middle Keys. A bright, breezy coastal escape and always a pleasure to show.

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$889,000
91
2bedrooms
2bathrooms
land 202

By Ocean Sotheby's International Realty

50
Video

House Islamorada (United States)

Discover an extraordinary opportunity to own 34,000 square feet of prime bayfront real estate in one of Islamorada's most coveted and private enclaves. Boasting 100+ feet of pristine bay frontage, this exceptional property captures open water views, serene sunsets, and the essence of the Florida Keys lifestyle. Tucked within the property is a charming ground level 1950s cottage offering one bedroom and one bathroom - ideal as a weekend escape, guest retreat, or comfortable interim residence while you bring your custom waterfront vision to life. For boating enthusiasts, the estate offers dockage with direct bay access, placing world-class fishing, sandbars, and crystal-clear waters just moments away. A permit has been submitted to repair and expand the existing dock and add two boat lifts (20,000 lb and 16,000 lb), significantly enhancing the property's boating capabilities and long-term value. Surrounded by multimillion-dollar estate home sales, this offering represents a rare chance to secure a premier bayfront parcel in one of Islamorada's most sought-after locations. With the existing estate slated for demolition and redevelopment, the conceptual renderings unveil a spectacular 4,872-square-foot custom residence offering five bedrooms, five and a half bathrooms, a three-car garage, and a resort style pool - all thoughtfully designed to capture water views from every vantage point. This vision blends refined indoor living with outdoor elegance, creating a seamless waterfront sanctuary. Whether you envision a private coastal retreat or an entertainer's paradise, this remarkable bayfront estate offers endless possibilities in an unparalleled setting.

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$4,499,500
88
1bedroom
1bathroom
land 3,157

By Ocean Sotheby's International Realty

50

House Summerland Key (United States)

Welcome to Pink Sands, a Glenn Gray-designed waterfront retreat where the vibrant colors and laid-back elegance of the Bahamas meet the timeless beauty of the Florida Keys. Recognizable by its signature pink façade and blue metal roof, this exceptional Summerland Key residence captures the spirit of island living while offering the quality, comfort, and peace of mind of modern CBS construction. Set along a protected canal with 125 feet of concrete dockage, two boat lifts, and direct deep-water access to both the Atlantic Ocean and Gulf of Mexico, this waterfront home is perfectly positioned for effortless days on the water, from world-class fishing and diving to sunset cruises and sandbar adventures. Impact windows and doors and thoughtfully designed indoor-outdoor living spaces create a home that is as durable as it is inviting. Sweeping open ocean views from the main living level and third-story observation deck provide the perfect backdrop for sunrise mornings and starlit evenings. A charming detached guest cottage connected by a covered breezeway creates a private compound ideal for hosting family and friends. The oversized homesite offers exceptional flexibility with ample room to add a custom pool, expand outdoor entertaining areas, or further enhance the property to suit your vision. Just 35 minutes from Key West, Pink Sands feels as though it belongs on Harbour Island while remaining firmly rooted in the authentic charm of Summerland Key. Blending Bahamian-inspired architecture with the confidence of newer CBS construction, exceptional boat dockage, direct ocean and Gulf access, and endless opportunities for future customization, this is a rare opportunity to own a distinctive Florida Keys waterfront home. Minutes from Looe Key Reef, Content Keys, and the backcountry flats, this exceptional location offers unparalleled access to some of the Florida Keys' most sought-after boating, fishing, diving, and paddleboarding destinations right from your private dock.

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$2,999,000
361
5bedrooms
4bathrooms
land 1,133

By Ocean Sotheby's International Realty

37

House Marathon (United States)

Lowest-Priced In-Ground Pool Home in Marathon with Weekly Rental Potential! Embrace the laid-back Florida Keys lifestyle in this charming tropical cottage, ideally located in the desirable Little Venice subdivision of Marathon. Offering 2 bedrooms, 2 bathrooms, and beautiful peek-a-boo ocean views, this bright and airy stilt home is perfectly designed for both relaxation and entertaining. The spacious deck provides the perfect setting for enjoying ocean breezes, morning coffee, or evening gatherings with family and friends. Inside, the open-concept living area features vaulted ceilings and abundant natural light, while the updated kitchen boasts stainless steel appliances, granite countertops, and ample cabinetry for effortless entertaining. Recent improvements include updated bathrooms, a new A/C system (2024), hot water heater (2026), and a durable metal roof (2013). Tastefully furnished with coastal-inspired décor, this home is being offered fully furnished, making it move-in or rental ready. Situated on a rare double corner lot, the property features a sparkling in-ground heated pool surrounded by tropical landscaping, along with covered parking, generous workshop/storage space below, and ample room for boat and trailer parking. An assumable low-cost flood insurance policy adds additional value and peace of mind.

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$729,500
109
2bedrooms
2bathrooms
land 486

By Ocean Sotheby's International Realty

50
Video

House with pool Islamorada (United States)

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

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$4,750,000
239
4bedrooms
5bathrooms
land 3.1ha

By Ocean Sotheby's International Realty

50

House Key Largo (United States)

Welcome to one of Buccaneer Point's most extraordinary waterfront estates-a breathtaking modern Balinese-inspired sanctuary where timeless architecture, exceptional craftsmanship, and resort-style living come together in perfect harmony. Situated on an oversized lot with more than 110 feet of waterfront, this custom CBS estate features a concrete roof, standing-seam metal roofing, and over $150,000 in professionally designed tropical landscaping. Dual electric gates welcome you with Royal Palms, Canary Island palms, bamboo, and mature privacy landscaping. Built for both everyday living and entertaining, the home offers expansive waterfront views, premium travertine and wood-look tile flooring, Hunter Douglas motorized shades, and a fully integrated Control4 Smart Home System. The chef's kitchen is equipped with premium JennAir appliances, double convection ovens, an additional wall oven, a six-burner gas range with griddle, pot filler, oversized island, custom cabinetry, and direct access to the waterfront balcony. The outdoor living space is designed for year-round enjoyment with a heated saltwater pool and spa, expansive travertine patio, outdoor kitchen with TV, bar seating, authentic Bakers Pride pizza oven, putting green, waterfront lounge area, cabana bath, covered entertaining space, irrigation system, mosquito misting system, pet run, and fully fenced grounds. Inside, the home offers four spacious bedrooms, including a main-level primary suite with private balcony access and coffee bar. The upper-level owner's retreat features dual walk-in closets, coffee and wine bar, dressing area, steam shower, separate his-and-hers bathrooms, and a private waterfront balcony. A custom wood elevator services every level, leading to a rooftop observation deck with power and water, offering panoramic views of Florida Bay, and some of the best sunsets in the Keys. Combining quality construction, premium amenities & outstanding waterfront location, this is a rare opportunity.

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$2,350,000
269
4bedrooms
4bathrooms
land 1,093

By Ocean Sotheby's International Realty

50
Video

House with pool Big Pine Key (United States)

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

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$4,650,000
435
3bedrooms
3bathrooms
land 4,613

By Ocean Sotheby's International Realty

49

House Marathon (United States)

Welcome to your dream escape in the Florida Keys. This spacious 3-bedroom, 3-bath oceanfront townhome in the highly sought-after Bonefish Yacht Club Townhomes offer the perfect blend of coastal and laid-back island living. Set within an intimate marina community of just 34 residences nestled among lush tropical landscaping, this home feels both private and resort-like and also conveys with a deeded boat slip in Bonefish Marina (B-34). Enter through the foyer and up to two levels of open living, with 1,769 sq. ft. thoughtfully oriented for comfort, water views, and easy entertaining. The chef's kitchen features generous cabinetry, ample counter space, and an inviting eat-in island that flows seamlessly into the main living area, where sliding glass doors open to a spacious waterfront balcony overlooking the Key Colony Channel--watch charter boats head out with your morning coffee and return as you relax with a sunset cocktail. The primary suite is a serene retreat with its own private balcony, walk-in closet, and ensuite bath, while two additional bedrooms offer flexible space for guests, family, or a home office, each with access to well-appointed baths. On the ground level, a private garage and generous storage provide the perfect place for fishing gear, paddleboards, and all your Keys lifestyle essentials. Residents enjoy a temperature-controlled pool, expansive sun deck, tiki lounge with wet bar, tennis and pickleball courts, and a private sandy beach. This is a rare opportunity to own a turnkey, single-family attached townhome with a boat slip in one of the Keys' most desirable waterfront communities where every day feels like a vacation. New roof in 2023 and new A/C in 25 with 12 year warranty.

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$899,000
164
3bedrooms
3bathrooms
land 81

By Ocean Sotheby's International Realty

29

House with terrace Windley Key (United States)

Charming concrete bungalow in the heart of Islamorada! Move right into this beautifully updated 1BR/1BA retreat featuring fabulous ocean views from your private rooftop deck. Blending timeless Florida Keys charm with modern finishes, this home offers durable concrete construction with beautiful interior finishes, impact windows, an updated electrical panel, and parking for two vehicles. Relax under the covered Chickee Hut while enjoying spectacular Atlantic sunrises and unforgettable sunset skies. Community amenities include dock privileges, the Atlantic Ocean Jetty Area, a community Chickee Hut, and a low HOA fee of just $149/month, all conveniently located near Snake Creek Marina. Looking for a weekend getaway, vacation rental, or full-time island escape, this is your opportunity to experience the best of Florida Keys living.

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$439,000
38
1bedroom
1bathroom
land 121

By Ocean Sotheby's International Realty

50
Video

House Islamorada (United States)

Big, beautiful, and exceptionally solid, this waterfront Islamorada residence is perfectly situated on Sandy Cove Basin with protected deep-water dockage for multiple boats and direct bay access. A gated, pavered double driveway leads to an inviting foyer where marble floors and a private elevator welcome you. The elevated living level features a spacious great room with fireplace and coral accents, ideal for entertaining, along with a chef's kitchen offering custom teak cabinetry, granite countertops, island cooktop, and premium Sub-Zero and Bosch appliances. Wide screened porches extend the living space and capture open waterfront views. The home offers 5 bedrooms and 5.5 baths, a resort-style pool, and excellent updates including a new dock, new boat lift, and new A/C systems. A privacy wall enhances the secluded feel of this quiet, one-street neighborhood known for its consistently lovely homes. An exceptional opportunity for refined island living with outstanding boating access.

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$5,999,999
507
5bedrooms
6bathrooms
land 1,659

By Ocean Sotheby's International Realty

50
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House Plantation Key (United States)

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

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$4,650,000
404
5bedrooms
6bathrooms
land 647

By Ocean Sotheby's International Realty

50
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House with pool Key Largo (United States)

Gracious waterfront living awaits at 35 Angelfish Cay Drive, a beautifully renovated canal-front residence in the heart of Ocean Reef Club, Key Largo's premier private club. Perfectly positioned on a deep-water canal with 120 feet of canal frontage, this home offers quick and effortless access to offshore fishing, snorkeling, and diving—an ideal retreat for boating and water-sport enthusiasts. Originally built in 2006 and elegantly reimagined in 2023, the home spans 6,300 square feet of refined interiors designed for relaxed yet luxury living. Featuring 5 bedrooms, 4 full baths, and 2 half baths, the residence offers abundant space for family and guests. Light-filled living areas flow seamlessly into a gourmet kitchen, multiple entertaining spaces, and expansive windows framing tranquil water views. Outside, a generous pool deck invites lounging and gatherings, with gentle steps leading to the private dock—perfect for keeping boats, paddleboards, and all your favorite water toys at the ready. Ideally located within Ocean Reef's amenity-rich environment, this home blends privacy, convenience, and timeless elegance for an unparalleled island lifestyle.

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$18,475,000
589
5bedrooms
6bathrooms
land 1,659

By Ocean Reef Club Sotheby's International Realty

41

House Marathon (United States)

This marina townhome plus 40' deeded deep water liveaboard boat slip in the exclusive Bonefish Yacht Club offers the perfect blend of luxury living and resort-style amenities in the heart of the Florida Keys. Nestled within a private 34-residence community set across more than four acres of beautifully maintained tropical grounds, the property captures the feel of a secluded oceanside retreat. Inside, the home offers 1,464 sq. ft. of light-filled living space featuring a gourmet chef's kitchen with brand new stainless steel appliances, a dedicated dining area, and an open-concept living room that flows seamlessly to a waterside balcony overlooking the marina, perfect for alfresco dining and entertaining. The spacious primary suite features a private waterfront balcony, walk-in closet, and a ensuite bath. The guest suite also enjoys its own balcony, a full bath, and generous closet space. The ground level includes a private tiled garage and storage area, ideal for a vehicle, fishing equipment, and water toys, perfect for the avid angler. Bonefish Yacht Club residents enjoy exceptional amenities including a heated and chilled pool with expansive sun deck, a tiki lounge gathering area with wet bar and seating, tennis/pickleball courts, and a private community beach. Offering breathtaking water views and beautifully maintained resort amenities, this residence delivers a rare opportunity to enjoy luxury waterfront living with access to world-class boating, fishing, and the best of the Florida Keys lifestyle.

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$1,175,000
136
2bedrooms
3bathrooms
land 121

By Ocean Sotheby's International Realty

45
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House Key Largo (United States)

Located on 1.85 acres of tropical and native landscaping, this mystical waterfront estate in Key Largo offers the perfect blend of privacy, comfort, and coastal living. Designed with both family life and entertaining in mind, this charming three bedrooms, two and a half bath residence features a spacious, light filled, open concept floor plan with clean architectural lines and seamless indoor- outdoor living. At the center of the home is a beautifully appointed kitchen anchored by an expansive island, creating the ideal gathering space for casual family meals and entertaining guests. Generous living spaces flow effortlessly to a covered central courtyard, extending the home's living area into a private outdoor sanctuary. Beyond the courtyard, the backyard unfolds into a breathtaking waterfront setting with direct ocean access. Surrounded by mature landscaping and exceptional privacy, this serene retreat feels like your own secluded oasis. Whether you are relaxing by the water, enjoying the tranquil surrounds, or setting out for a day on the ocean, this property captures the best of the Florida Keys lifestyle.

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$1,874,000
237
3bedrooms
3bathrooms
land 7,487

By Ocean Sotheby's International Realty

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