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Browse All Key West FL Between $800K - $900K Properties for Sale

$819,000
1 Beds 1 Baths 620379 MLS
This elegant historic Old Town cottage is a rare offering paired with a highly competitive price. In addition, it is being sold completely turnkey! Sparkling, gallery-like, and filled with natural light, this beautifully renovated Old Town Key West cottage offers the perfect blend of charm, privacy, and modern comfort. Tucked away on a quiet one-way street, this tropical retreat is just a short stroll to Cafe Sole, Little Pearl, Fausto's Food Palace, local bakeries, and charming boutiques. Renovated down to the studs, the home features vaulted ceilings and an open-concept layout where the gourmet kitchen, entertainment bar, and living area come together to create a bright, welcoming gathering space. True to the Key West lifestyle, an expansive sliding glass door opens to a serene tropical oasis framed by lush fig vines, Spanish lime trees, swaying palms, and a majestic Royal Poinciana tree, where morning coffee, afternoon cocktails, and evenings under the stars become part of everyday life. The property also offers dedicated off-street golf cart parking, potential for a small pool, and no HOA fees, further enhancing its appeal as a private sanctuary. Thoughtfully selected upscale finishes include solid teak flooring, granite countertops, and a beautifully appointed Calacatta marble shower tub. The renovation includes all-new electrical and plumbing systems, an efficient tankless hot water heater, a metal roof, impact-rated windows and opening protections, and stylish finishes throughout. Situated in the desirable X Flood Zone, the property offers an added layer of peace of mind with reduced flood risk concerns. Steeped in Key West history, this charming cottage was once home to a local cigar maker, offering a connection to the island's rich cultural heritage while embracing the pleasures of contemporary living.

1105 Olivia St, Key West

$868,000
2 Beds 2 Baths 620198 MLS
Rare opportunity to own a transiently licensed 2-bedroom, 2-bathroom condo in Key West, offering exceptional flexibility for personal use and short-term vacation rental income. Located within the sought-after Sunrise Suites community, this beautifully updated residence combines modern coastal style with a prime island location just minutes from beaches, Old Town, and Key West's most popular attractions. Inside, you'll find a bright, open-concept living space featuring elegant quartz countertops, contemporary white cabinetry, and a thoughtfully designed layout that maximizes comfort and functionality. The spacious primary suite and guest bedroom provide comfortable accommodations, while the open living and dining areas create the perfect setting for relaxing or entertaining. A private balcony offers the ideal place to unwind and enjoy breathtaking sunset views over the island. This turnkey condo is equipped with a beautifully updated kitchen, in-unit washer and dryer, and central air conditioning, making it equally appealing as a primary residence, second home, or investment property. Owners and guests enjoy access to resort-style amenities including a shared heated swimming pool, hot tub, tennis court, and beautiful walking and biking paths. The community's convenient location near Key West International Airport and just a short drive from Duval Street provides easy access to world-class dining, nightlife, shopping, fishing, and water sports. With its coveted transient rental license, updated interior, desirable amenities, and strong vacation rental potential, this Key West condo presents an outstanding opportunity to own a piece of paradise while generating income in one of Florida's most sought-after destinations.

3625 Seaside Dr Unit 25410, Key West

$889,000
3 Beds 2 Baths 619926 MLS
Now offered at $889,000, this 2-bedroom, 2-bath Key West beachfront condo sits ground-floor at Key West by the Sea, directly across from Smathers Beach, a rare setup that lets you walk to the sand without stairs, elevators, or commuting. At 1,221 square feet, the 3BR deeded layout lives comfortably open, with room to actually use the space rather than just pass through it. Dual-zone split A/C allows personalized comfort. Hurricane-impact, soundproof windows and doors provide enhanced security, energy efficiency, and peace of mind all year long. Inside, luxurious porcelain flooring runs throughout, paired with detailed bathroom tile work chosen to match the quality of the rest of the home. The kitchen carries soft-touch cabinetry and granite countertops -- quiet, durable choices that hold up well in a beach environment, which matters more here than most out-of-state buyers realize until they've owned property in the Keys for a few years. Key West by the Sea is a managed beachfront community with resort-style amenities, meaning pool, grounds, and building upkeep are handled for you offering low-maintenance, turnkey ownership that buyers relocating from out of state especially value. The building has never flooded, a track record that matters as much as the view when you're evaluating waterfront property in the Florida Keys. This stretch of South Roosevelt Blvd sits between the Atlantic shoreline and the island's laid-back Old Town core, across the street from Smathers Beach, close to Key West International Airport, and minutes from Duval Street, the historic Bight, and Higgs Beach. It's the kind of setting where morning coffee happens on the terrace with saltwater air and pool views, evenings mean sunset over the water instead of a screen, and life moves at the pace islanders have always known: bike rides instead of traffic, conch culture instead of chain restaurants. That's the island lifestyle longtime locals like myself have watched hold its value for decades.

2601 S Roosevelt Blvd Unit APT 103C, Key West

$874,500
3 Beds 3 Baths 619867 MLS
A bougainvillea-covered trellis and cozy front gate welcome you! Charming, secluded island retreat overlooks the Key West Golf Course. Within the gated KW Golf Club community, this beautifully maintained home offers a rare combination of privacy, tropical ambiance, truly unique architectural features. One of the most exceptional attributes is its expansive wraparound verandas on both levels, a customized feature found in only 1 townhome building w/in the entire community. These divine outdoor living spaces create an extraordinary extension of the home w/seamless indoor-outdoor island living, panoramic tropical views, refreshing S.E./S.W. breezes flowing throughout. Spacious interior features: upgraded Italian ceramic tile on main level, luxury vinyl flooring on steps/upstairs, vaulted ceilings, creating an open atmosphere. Custom kitchen offers ceiling-height cabinetry, granite countertops, upgraded stainless appliances, generous prep space. French doors throughout the residence invite natural light into every room while enhancing the true ''island residence'' experience. Convenient powder rm. downstairs, separate washing machine/dryer closet. Spacious living/dining room areas, taller ceiling, 2 nautical fans, leading directly to an amazing, tranquil space. The lower-level tiled veranda, dual ceiling fans, functions beautifully as an additional entertaining area, more generous in size compared to most homes. Hidden behind layers of tropical foliage, the rear yard feels like a secret island garden. Expansive Boston brick patio, towering palms, soothing heated jacuzzi, reminiscent of a boutique resort tucked quietly along #2 tee box/fairway. Gentle tropical breezes, surrounding greenery provides privacy/serenity. The primary bdrm. is en-suite w/French doors opening onto expansive upper veranda. 2 guest bedrooms w/shared bath each w/French doors. Extraordinary opportunity to own a private tropical retreat, classic KW architecture charm, laid-back sophistication & more

56 Golf Club Dr, Key West

$849,900
3 Beds 2 Baths 619859 MLS
Welcome to island living in the highly sought-after Key West Golf Club community! This beautifully maintained home at 34 Golf Club Drive offers the perfect blend of comfort, upgrades, and convenience in a gated neighborhood just minutes from Old Town Key West. This light-filled home features an open-concept living area with soaring ceilings, luxury vinyl plank flooring, and sliding glass doors that bring the outdoors in. The updated kitchen offers quartz countertops, white cabinetry, stainless steel appliances, and a functional layout ideal for entertaining or everyday living. Thoughtful upgrades include impact windows on the front and back of the home, hurricane shutters for major entrances and side windows, spray foam insulation in the crawl space, and a newer air handler installed approximately five years ago. A new rear fence and gate provide direct access to the golf course, while peaceful views of the 5th and 6th holes and lagoon create a relaxing island atmosphere. The upstairs bedrooms feature beautiful vaulted ceilings, adding charm and an airy feel throughout the upper level. Outdoor spaces are surrounded by mature tropical landscaping, perfect for relaxing or entertaining. Additional highlights include a termite guarantee already in place for added peace of mind and an assumable VA loan with an exceptionally low 1.99% interest rate. Non-military buyers may also qualify to assume the loan if the property will be used as their primary residence, subject to lender approval and VA guidelines. Residents of the Key West Golf Club community enjoy access to resort-style amenities including two pools, a fitness center, gated security, and beautifully maintained grounds. Whether you're searching for a primary residence, second home, or investment opportunity, this property captures the essence of easy Key West living. Tenant until 5/31/26 24 hour notice needed

34 Golf Club Dr, Key West

$850,000
2 Baths 619620 MLS
FOR SALE: Mellow Ventures LLC - Premier Eco-Tour & Luxury Houseboat Rental Company in the Florida Keys Step into one of the most unique lifestyle and income-producing businesses in the Florida Keys. Mellow Ventures LLC is a turnkey, multi-stream eco-tour and hospitality operation with a proven track record, established brand presence, and rare waterfront assets perfectly positioned for continued growth. Operating out of Key West, this boutique adventure company has built a reputation for intimate, sustainable experiences on the water—guided eco tours, private charters, island excursions, and custom adventures designed to showcase the natural beauty of the Lower Keys. In addition to its successful charter business, the sale includes two custom-built luxury houseboats, currently operating as high-demand short-term rentals. These floating suites offer a one-of-a-kind Airbnb experience that consistently generates strong occupancy and premium nightly rates. Each vessel blends modern comfort with an immersive waterfront setting, providing an unforgettable stay for guests seeking something truly special. Highlights Include: -Well-established eco-tour & charter business with brand recognition in Key West -24' Twin Vee -Two fully custom houseboats designed for nightly rentals -Strong Airbnb track record with exceptional occupancy -Multiple revenue streams: eco tours, private charters, overnight rentals -Turnkey operation with booking systems, media assets, furnishings & equipment -Excellent online reviews and repeat clientele -Ideal opportunity for owner-operator or investor seeking passive/managed income -Rare waterfront lifestyle business in a world-renowned destination This is a unique chance to acquire a thriving, experiential Keys business blending adventure tourism with boutique hospitality—a lifestyle investment that generates real returns.

Rat, Key West

$860,000
2 Beds 2 Baths 616231 MLS
Welcome to 3365 Flagler Avenue, a beautifully updated and meticulously maintained 2 bed, 2 bath townhome in the Villas of Key West. Built of solid CBS construction and spanning 1,339 square feet, this two-story home is located above flood, has off-street parking and no HOA fees. The interior features a bright, open floor plan with Saltillo tile floors, updated lighting, and smart home conveniences. The kitchen is well appointed with stainless steel appliances including newer refrigerator, microwave, and dishwasher, along with tasteful under-cabinet lighting. The upstairs primary suite offers vaulted ceilings, a private screened porch, walk-in closet, and a fully remodeled bathroom. A custom wall of built-in bookcases with a rolling library ladder provides a striking focal point and versatile space for books, art, or display. Upstairs you will also find the laundry area with a new washer, and a pull-down attic stairs providing additional storage. Outdoor living is exceptional. The front porch has been rebuilt with Azek decking and doubled pilings, while the expanded back porch includes steel beams, doubled pilings, an awning, and Azek decking. The large fenced yard has a multilevel deck, tropical landscaping, flagstone pavers, and plenty of space for a pool or spa. Over the past six years the seller has invested in thoughtful updates including a remodeled primary bath, electrical panel replacement and expansion, reworked plumbing with whole-home filter, a new water heater, and numerous upgrades to porches and outdoor living spaces. Additional features include mature landscaping, off-street parking, and a location just minutes to Old Town and beaches. This home is move-in ready, carefully maintained, and offers the perfect combination of comfort, style, and convenience in the heart of Key West. Sold as shown. NO HOA FEES!

3365 Flagler Ave, Key West

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