Ocean Sotheby's International Realty
1075 Duval Street Suite 15C, 33040 Key West (United States)
Listings of the agency
Listings for sale: 1 to 20 / 30
- 41
House with garden and terrace Key West (United States)
Located in the heart of Old Town Key West, 914 Windsor Lane is the quintessential Key West conch cottage that captures the island's timeless charm. Behind the classic white picket fence and vibrant turquoise front door awaits a thoughtfully updated 1-bedroom, 1-bath retreat blending historic character with modern comforts. Inside, vaulted cathedral ceilings, Dade County pine accents, quartz countertops, stainless steel appliances, and abundant natural light create an inviting island atmosphere. French doors open to a generous rear covered porch, perfect for outdoor dining and entertaining. The private tropical yard offers room for a pool and plenty of space to relax and enjoy the laid back Key West lifestyle. Additional highlights include a whole house generator, central A/C, metal roof, tankless water heater, private deeded parking area, and an unbeatable Old Town location just moments from dining, galleries, nightlife, and the best of island living.
…$1,100,00055m²1bedroom1bathroomland 202m²By Ocean 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.
…$1,550,000129m²2bedrooms2bathroomsBy Ocean Sotheby's International Realty
- 12
House with garden and terrace Key West (United States)
Timeless Old Town Charm! Discover the timeless appeal of this beautifully remodeled historic home located in the heart of Old Town, Key West. Offered fully furnished, this stunning 3-bedroom, 2.5-bath residence showcases lovingly restored Dade County Pine and blends classic craftsmanship with today's most desirable upgrades. 1211 Knowles Lane features a versatile 300 sq. ft. loft currently utilized as a third bedroom, office, and additional storage, perfect for flexible island living. Inviting front and side porches set the tone for relaxed Key West living, offering peaceful spaces to unwind and enjoy the tranquil neighborhood. Inside, you're welcomed by bright, spacious living areas highlighted by soaring ceilings and gorgeous flooring throughout the living and dining rooms. The thoughtfully updated kitchen boasts stainless steel appliances, custom cabinetry, and a generous pantry designed for both everyday living and entertaining.The bedrooms are comfortably sized, offering charm and privacy. Bathrooms have been tastefully renovated with contemporary fixtures while preserving the home's historic character. Step outside onto beautiful teak decking into your own private tropical oasis. The backyard retreat features an outdoor shower, hot tub, rooftop deck, and brick-paved driveways creating the ultimate indoor-outdoor island lifestyle. Located in a prime Old Town setting, you're just a leisurely walk or bike ride to Key West's beautiful beaches, renowned restaurants, and vibrant nightlife. *Bonus features: off street parking and located in the x-flood zone.
…$1,475,000119m²3bedrooms3bathroomsland 202m²By Ocean Sotheby's International Realty
- 31
House with garden Key West (United States)
Tucked away on a quiet lane in Old Town Key West, this historic island home offers a rare combination of architectural character, elevated location, and walkable convenience. Positioned in the desirable X-flood zone near the island's highest natural elevation, the property sits just steps from the energy of Duval Street while maintaining a peaceful residential feel. Originally constructed during the Henry Flagler railroad era, the home has been thoughtfully updated while preserving the warmth and authenticity that make Key West architecture so iconic. Inside, rich Dade County pine walls, hardwood flooring, and tall ceilings create an inviting atmosphere filled with natural texture and timeless charm. Impact windows and curated high-end finishes blend seamlessly with the home's historic roots. The kitchen was designed with both style and function in mind, featuring Dade County pine countertops and a collection of premium appliances, including a Sub-Zero refrigerator and Big Chill gas range. Flexible living areas allow the home to function as either a spacious two-bedroom retreat or a three-bedroom layout depending on your needs. Outdoor living is equally special. A lush backyard filled with mature tropical landscaping and fruit trees creates a private island setting that feels worlds away from the bustle of town, with space to potentially add a pool in the future. The welcoming front porch serves as a timeless gathering space, perfectly suited for morning coffee, evening cocktails, and enjoying the laid-back rhythm of Old Town living. Just a short stroll from Truman Waterfront Park, Fort Zachary Taylor Beach, galleries, restaurants, and marinas, this property captures the essence of classic Old Town living -- historic, relaxed, and unmistakably Key West.
…$1,150,000101m²2bedrooms2bathroomsland 243m²By Ocean Sotheby's International Realty
- 44
Contemporary house with garden Key West (United States)
Located in the heart of Key West, 1712 Laird Street offers a rare blend of central convenience and residential tranquility. Positioned within a short stroll of Smathers Beach, Higgs Beach Park, the Key West Nature Preserve, White Street Pier, and the island's beloved Garden Club and dog park, this home places the best of the island lifestyle quite literally at your doorstep. Duval Street and the Old Town Historic District lie just 1.5 miles away, while Mallory Square and the waterfront—famed for their sunsets, dining, and culture—are approximately 2 miles from the property, allowing effortless access without sacrificing peace and privacy . Designed by an architect with a discerning eye for light and space, the residence showcases a modern open-concept floor plan enhanced by expansive glass elements that invite the outdoors in. Cathedral ceilings soaring from 12 to 15 feet throughout every room create a sense of volume and airiness seldom found in Key West homes, delivering a bright, refined interior that feels both contemporary and timeless . Set on a 5,000-square-foot parcel, the grounds are thoughtfully landscaped with low-maintenance native flora, including seven mature palm trees, a striking gumbo limbo, and established orchids. The result is a private tropical sanctuary—lush, authentic, and effortlessly elegant—perfectly suited for island living without pretense . Large back yard offers plenty of space to add a pool!
…$1,289,000128m²3bedrooms2bathroomsland 486m²By Ocean Sotheby's International Realty
- 50
House with garden Key West (United States)
Multi-unit legal duplex! With only two owners in its history, this well-maintained two-story property presents a rare investment opportunity in Key West. Configured as a legal duplex with two separately metered 1-bedroom, 1-bath units, it offers exceptional flexibility--ideal for investors seeking strong rental potential, business owners looking for employee housing, or owner-occupants wanting to offset costs by renting one unit while living in the other. Set on a 5,000 sq ft lot, the property is surrounded by lush, mature tropical landscaping with a wide variety of plants and palms, creating a private, shaded, treehouse-like setting filled with natural light. Two large screened porches and additional open-air spaces provide ideal indoor-outdoor living, while an outdoor shower enhances the island lifestyle. The home has been thoughtfully updated and well cared for, featuring Mitsubishi mini-split A/C systems in both units, a new hot water heater, new ceiling fans, impact windows upstairs, new gutters, updated appliances, and soft-close cabinetry. Interior finishes include a mix of pine, vinyl, and concrete flooring, along with stainless, Formica, and butcher block countertops. Both units offer full bathrooms with tubs. Additional highlights include two off-street parking spaces, low-maintenance grounds, and multiple windows throughout for abundant natural light and airflow. Located in desirable Midtown East, just minutes from everything Key West has to offer, this is a versatile, income-producing property with strong upside potential.
…$1,250,000104m²2bedrooms2bathroomsland 445m²By Ocean Sotheby's International Realty
- 44
Seaside apartment with pool Key West (United States)
Discover the rare opportunity to own a premier developer's unit in one of Key West's most desirable waterfront communities. Perfectly positioned just across the street from world-famous Smathers Beach, this spacious 3-bedroom, 2-bath condo blends coastal luxury with unbeatable island convenience. Inside, expansive living spaces open to large windows and glass doors showcasing ocean views and endless natural light. The open-concept kitchen flows seamlessly into the dining and living areas—ideal for entertaining or relaxing after a day on the sand. Retreat to the ocean-view primary suite, complete with generous closet space and private bath. Two additional bedrooms offer the flexibility for guests, family, a home office, or rental income. Step outside and enjoy resort-style amenities—lush tropical grounds, shoreline paths, sparkling pool, and easy access to water sports, biking, and Key West's sunset scene. Whether you're seeking a primary residence, island getaway, or investment opportunity, this condo delivers everything that makes Key West living unforgettable. Highlights: *Rare developer's unit with expanded layout/premium features *Just steps to Smathers Beach, bike paths & sunrise walks *3 Bedrooms / 2 Bathrooms *Assigned covered parking bay and storage unit *Resort amenities & gated community *Minutes to Old Town, dining, airport & nightlife Your Key West waterfront life starts here—schedule your private showing today!
…$1,425,000130m²3bedrooms2bathroomsBy Ocean Sotheby's International Realty
- 50
House with pool Big Pine Key (United States)
Welcome to your perfect Florida Keys getaway in the heart of Big Pine Key. This charming 2-bedroom, 1-bath home offers an inviting open-concept layout that flows seamlessly between the living, dining, and kitchen areas. Natural light pours in through large windows, creating a bright, airy feel that complements the relaxed island setting. The kitchen features stainless steel appliances and a functional layout ideal for everyday living or entertaining. Step outside to enjoy ample space for gathering with friends, soaking up the sunshine, or unwinding after a day on the water. A dedicated storage area keeps all your outdoor gear organized and ready to go. Recent updates include: -On-demand hot water heater (2023) -12x20 above-ground pool (2022) -Plantation shutters (2022) -Upgraded HVAC air handling unit (2022) -Galvanized 6x10 shed for extra storage -RV hookup available Enjoy convenient access to multiple nearby boat ramps, and the benefit of being on one of the only islands between Marathon and Key West with a grocery store. Don't miss the opportunity to own a piece of paradise--schedule your showing today and start living the Florida Keys lifestyle.
…$595,00079m²2bedrooms1bathroomland 526m²By Ocean Sotheby's International Realty
- 30
Seaside contemporary apartment with terrace Big Coppitt Key (United States)
Experience refined island living in this newly remodeled waterfront condominium--VA buyer ready and now approved for conventional financing--ideally located just minutes from NAS Key West and the charm of Old Town. This light-filled 1-bedroom, 1-bath residence has been thoughtfully transformed with sophisticated modern finishes and a clean, open design. From the moment you enter, you're welcomed by new flooring, elevated fixtures, and a seamless layout designed for both comfort and style. The designer kitchen showcases sleek cabinetry, quartz-inspired countertops, stainless steel appliances, and a contemporary backsplash--perfectly blending function with understated elegance. The living space opens to a private waterfront balcony, offering tranquil views and gentle island breezes--an inviting setting for morning coffee or sunset relaxation. The spacious bedroom provides abundant natural light and generous closet space, while the beautifully updated bath features modern tilework, a refined vanity, and polished fixtures that complete the home's elevated aesthetic. Residents enjoy assigned parking, waterfront common areas, and temporary dock space ideal for kayaking or simply enjoying the serene coastal setting. With effortless, low-maintenance ownership, this residence is perfectly suited as a primary home, second residence, or sophisticated lock-and-leave retreat in the heart of the Florida Keys. TO FURTHER ENHANCE THIS EXCEPTIONAL OPPORTUNITY, THE SELLER IS OFFERING A CREDIT EQUAL TO SIX MONTHS OF HOA FEES AT CLOSING WITH A QUALIFIED OFFER.
…$299,00050m²1bedroom1bathroomBy Ocean Sotheby's International Realty
- 31
House Key West (United States)
***BRAND NEW ROOF JUST INSTALLED *** 1614 Dennis St is a rare income-producing triplex offering strong cash flow and flexible use in the heart of Key West. Generating over $125,000 annually in rental income, this well-configured property features three separate units, each with its own washer and dryer, making it highly desirable for long-term tenants and employee housing. The layout includes two spacious 2-bedroom / 1-bath units and an upstairs 3-bedroom / 2-bath residence, providing multiple rental strategies and value-add potential. A standout feature is parking for up to 7 vehicles--a true luxury in Key West and a major draw for tenants. Large Shed on property with two dedicated spaces that could be converted into a workspace. Ideal for investors seeking steady returns or employers looking for quality workforce housing, this triplex combines strong income, practical design, and exceptional parking in one compelling opportunity. Please note some photos were digitally staged and or altered to protect tenant privacy.
…$1,299,000251m²7bedrooms4bathroomsland 486m²By Ocean Sotheby's International Realty
- 50Video
Contemporary apartment with terrace and pool Key West (United States)
Discover a seamless blend of historic character and modern refinement at 1209 Packer Street, a distinctive Old Town residence that quietly impresses from the moment you step inside. Drawing inspiration from the rich architectural tapestry of Key West, this home thoughtfully weaves together Old Key West charm, Cuban mosaic tile accents, and contemporary finishes to create an atmosphere that feels both timeless and current. Behind its unassuming façade lies a surprisingly expansive interior offering four bedrooms and four baths, including three bedrooms with three baths on the main level and a private upstairs bedroom with its own bath, ideal as a guest suite, apartment-style retreat, or income-producing space. An additional office or flex space off one of the bedroom suites allows work and relaxation to coexist effortlessly. The single-level main floor is designed with intention—each bedroom enjoys privacy while remaining easily accessible. Interior details include travertine and Ipe Brazilian hardwood floors, wood-clad ceilings, and a gourmet kitchen outfitted with stainless steel appliances and a wrap-around peninsula that naturally becomes the heart of the home. Whether hosting friends or enjoying everyday living, the flow is intuitive and inviting. French doors throughout the home create a strong connection to the outdoors. One bedroom opens directly to the pool, while another enjoys a peaceful, tucked-away deck perfect for morning coffee or quiet reflection. The primary suite is a true sanctuary, featuring vaulted ceilings, a spacious marble bath with multi-jet shower, walk-in closet, and direct access to an expansive Ipe sundeck. Outside, a large heated pool anchors a lush, private oasis surrounded by tropical landscaping and a privacy fence—ideal for entertaining or unwinding in complete tranquility. A shaded loggia adds yet another layer of livable outdoor space. Off-street parking, including a bricked driveway, provides rare Old Town convenience.
…$2,175,000200m²4bedrooms4bathroomsland 445m²By Ocean Sotheby's International Realty
- 50
House with pool Key West (United States)
Set on the highly desirable upper end of Eagle Avenue, this four bedroom, three bath home blends timeless charm with a breezy indoor outdoor lifestyle. Arched doorways, plantation shutters, and warm wood floors set the tone, while natural light fills the expansive living spaces. The main living area is centered around a working gas fireplace, creating a welcoming focal point for both everyday living and entertaining. On the main level, you will find three bedrooms, two bathrooms, a formal dining room, and a separate cooks kitchen featuring custom cabinetry, quartz countertops, premium appliances, and a center island. Glass fold back doors open to a covered outdoor living area, pool, and spa, extending the living space outdoors and creating a relaxed courtyard style setting ideal for entertaining or unwinding. Upstairs, the fourth bedroom with ensuite bath offers a private retreat, along with an additional living space and a large finished attic providing exceptional storage. This home provides the perfect opportunity to personalize every space and make it your own. Additional highlights include gated, covered off street parking, tiled walkways, and a fully fenced property for added privacy. Some photos have been virtually enhanced to illustrate potential.
…$1,689,000254m²4bedrooms3bathroomsland 557m²By Ocean Sotheby's International Realty
- 41
House with pool Key West (United States)
Welcome to 60 Golf Club Drive a fully furnished tropical retreat with private pool and turnkey rental opportunity. Step into island living at its finest in this beautifully appointed three bedroom, two and one half bath home with well appointed den / office (could function as 4th bedroom) located in the sought-after Key West Golf Club community. This charming residence offers the perfect blend of comfort, style, and convenience, and is being sold fully furnished, including all furniture, décor, and household essentials—just bring your flip-flops. Enjoy your own private pool surrounded by lush tropical landscaping, creating a serene outdoor oasis perfect for lounging, entertaining, or a refreshing dip after a day in the sun. Whether you're seeking a vacation getaway or a lucrative investment, this home delivers. All future bookings will convey with the sale, offering immediate income potential and a seamless transition into ownership. Located in a gated community with 24-hour security, two resort-style pools, a fitness center, and close proximity to world-class dining, beaches, and downtown Key West, this property truly has it all. Don't miss your chance to own a turnkey slice of paradise in the Florida Keys.
…$995,000112m²3bedrooms3bathroomsBy Ocean Sotheby's International Realty
- 2
Apartment Stock Island (United States)
This is a unique opportunity to own a 25 X 80 deep water slip in paradise. The slip comes with parking and all the amenities of Safe Harbor Marina.
…$249,000By Ocean Sotheby's International Realty
- 2
Apartment Stock Island (United States)
This is a unique opportunity to own a 25 X 80 commercial deep water slip in paradise. This slip comes with parking and the amenities of Safe Harbor Marina.
…$249,000By Ocean Sotheby's International Realty
- 1
Apartment Stock Island (United States)
This is a unique opportunity to own a 25 X80 deep water house boat slip in paradise. The slip comes with parking and the amenities of Safe Harbor Marina.
…$249,000By Ocean Sotheby's International Realty
- 24
House Key West (United States)
Situated in the heart of Bahama Village, one of Key West's most historic and vibrant neighborhoods, 209 Olivia Street offers a rare chance to reimagine a classic island home. This three-bedroom, one-bath residence is ready for a renovation, presenting an exceptional opportunity to restore the charm and character of Old Town living. Located just moments from Duval Street, the Truman Waterfront, and Fort Zachary Taylor, the property offers both convenience and an authentic Key West lifestyle. With vision and restoration, this historic home could become a truly special residence in one of Key West's most desirable locations.
…$799,00084m²3bedrooms1bathroomland 202m²By Ocean Sotheby's International Realty
- 47
House with pool Key West (United States)
Traditional Key West home impeccably maintained, boasts three bedrooms, three full baths with plenty of closets throughout the home. Large private lot with a heated pool featuring a waterfall. Nice size cabana room that has a/c and heat with ample closet space can be a fourth bedroom. This home has large rooms for entertaining, quaint front porch and off street parking. A true treasure.
…$2,595,000190m²3bedrooms3bathroomsland 283m²By Ocean Sotheby's International Realty
- 25
Apartment with pool Key West (United States)
Welcome to 3841 North Roosevelt Blvd, Unit 121, the epitome of beachfront living at the Key West Beachside Resort and Residences. This stunning waterfront corner suite invites you to live like you are on vacation every day. This is a rare to come on the market opportunity, as there are only three one-bedroom units on the entire property, and this beachfront location remains the most desired. Inside, designer-grade finishes and furnishings create an atmosphere of refined elegance. Travertine flooring flows throughout the spacious living areas, complemented by an open gourmet kitchen featuring granite countertops, stainless steel appliances, and custom cabinetry. The well-appointed bedroom and two bathrooms provide ample space and privacy, while a sleeper sofa offers additional sleeping accommodations for guests. An oversized balcony provides a private retreat to enjoy the tropical breeze and breathtaking Gulf sunsets. Beyond your door, the resort's world-class amenities await, including a restaurant, bar, pool, spa, and fitness center. The on-site parking garage includes one deeded parking space, and there is a property shuttle for added convenience. This superb property offers incredible flexibility: use it as your private getaway, generate income through the onsite professionally managed rental program with no maximum stay restriction for owners, or both. The property boasts a proven track record of strong rental performance throughout 2025, demonstrating its appeal as a high-performing investment. Don't miss this prime opportunity to own a piece of paradise that is perfect for part-time residency and robust passive income. Reach out to learn more about how to make this your 2026 lifestyle.
…$799,0001bedroom2bathroomsBy Ocean Sotheby's International Realty
- 50
House Key West (United States)
Situated on one of Key West's most desirable streets, this private compound on Eagle Avenue offers a rare combination of space, privacy, and refined island living. Set on a double corner lot totaling 12,000 sq ft, the property is fully enclosed, offering enhanced privacy and a tranquil, resort-like setting. The main residence features 3 bedrooms, 2.5 baths, and approximately 1,765 sq ft of thoughtfully designed living space with a comfortable open floor plan ideal for entertaining. The spacious primary suite serves as a private retreat, complete with a large en suite bath featuring a walk-in shower and oversized Jacuzzi tub. A separate guest cottage offers 1 bedroom, 1 bath, and approximately 625 sq ft, providing excellent flexibility for guests, extended family, or additional living space. The professionally landscaped grounds are a standout feature, enhanced by landscape lighting and irrigation, and centered around a large pool set within an exceptionally private backyard. Outdoor amenities include a hammock and swing area, outdoor shower, and multiple areas for entertaining or quiet relaxation beneath the palms. Additional highlights include a whole-house generator, as security system, one-car garage, and generous off-street parking. Surrounded by notable luxury homes, Eagle Avenue is known for its quiet atmosphere, large lots, and enduring desirability. A rare opportunity to own a private Key West compound offering privacy, flexibility, and presence on one of the island's most sought-after streets. Seller is a licensed real estate agent.
…$2,345,000222m²4bedrooms4bathroomsland 1,115m²By Ocean Sotheby's International Realty
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