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$3,600,000
4 Beds 4 Baths 620913 MLS
Discover modern island luxury at 119 Simonton Street, a premier end-unit townhouse nestled within the exclusive gated community of Old Town Villas. Built in 2018 and spanning a generous 2,691 square feet, this residence seamlessly blends sophisticated contemporary design with the timeless allure of Key West. The interior features new white oak flooring that leads you through an open-concept living space. The kitchen is a true standout, boasting elegant granite countertops and a custom kitchen island--a unique feature in the community. For the ultimate convenience, a private elevator services all four floors of the home, transporting you from the air-conditioned two-car garage to the spectacular rooftop terrace where you can view daily sunrises over the Historic Key West Marina and sunsets over Mallory Square, both a very short walk away. The top floor features a rare full bathroom and a flexible bonus room ideal for a home office or guest suite. Whether you're mixing drinks at the custom wet bar or lounging on the terrace, this level serves as the ultimate private retreat for taking in breathtaking panoramic views. Peace of mind is built into the architecture with full impact-rated windows and doors and a durable metal roof, ensuring the home is as secure as it is beautiful. The third floor has two primary bedrooms featuring large walk-in closets and balconies. The lifestyle offered here is unparalleled, situated just one block off the vibrant energy of Duval Street. You are steps away from the island's best dining and boutiques, yet you can retreat instantly to the quiet security of a gated community. Spend your afternoons lounging by the large tropical community pool and cabana area, enjoying a level of comfort and convenience unsurpassed in the heart of Old Town. With a rare two-car garage and an unbeatable location, this residence captures the very best of the Florida Keys lifestyle.

119 Simonton St, Key West

$649,000
2 Beds 2 Baths 620820 MLS
There are homes that simply check the boxes--then there are homes that immediately feel like ''home.'' Tucked on a quiet, 1-way lane w/in Key West Golf Club, 19 Spoonbill enjoys a superbly tranquil setting overlooking the lush, colorful Butterfly Garden/pond. The pace seems to slow. From the newly built composite rear veranda/rear steps, the gentle trickle of water from the Butterfly Garden statue becomes part of the soundtrack. Tropical greenery creates a peaceful backdrop for morning coffee/afternoon relaxation/evening glass of wine. Exceptional Location. Community Center/Fitness Room/HOA Office are just steps away, while the spectacular lagoon-shaped community pool w/tropical waterfalls is only a short stroll through the garden or down the inviting lane. Everyday living feels a little more like a Key West escape. Inside/out, this pristine residence has been given an extraordinary level of care. Freshly painted throughout, the home is sparkling, warm & inviting! For the homeowner seeking a property where the hard work has already been done, this one is the answer. Impressive exterior renovation. The entire front fence/gate has been meticulously rebuilt, posts/pickets re-secured w/ stainless-steel fasteners, 5 new pressure-treated wood panels. Front lower veranda has been completely rebuilt, enhanced w/new composite picture framing, rich English Walnut composite decking/new stair stringers, posts wrapped in composite sleeves/new composite railings. Upper belt/trim on the front/rear replaced w/Azek, secured w/stainless fasteners. Side/rear fencing was carefully re-secured, new pickets/new gate added. Freshly painted white trim/soffits/gutters/rails/balusters complete the polished exterior presentation. 4 brand-new stainless Frigidaire Gallery Series appliances. Wainscoting accented stairwell/rich wooden stairs/flooring upstairs, 2 glorious upper verandas, new lighting fixtures, 2021 AC, tented in 2018/continued Orkin treatment plan, solar lighting. LOOK NO FURTHER

19 Spoonbill Way, Key West

$615,000
3 Beds 2 Baths 620811 MLS
In New Town, where island convenience meets everyday ease, this beautifully renovated home delivers the kind of low-maintenance, family-ready living that's increasingly hard to find in Key West. Offered at $615,000, three-bedroom homes at this level are a rarity on the island, making this an exceptional entry point into Keys ownership. Set on a 2,055 sq. ft. lot with a fully fenced front yard, the home welcomes children and pets alike into a private, secure outdoor retreat -- a rare offering so close to town. Inside, 1,264 sq. ft. of thoughtfully renovated living space unfolds across two levels, beginning with a ground-floor primary suite positioned just off the open kitchen and living area, ideal for single-level living or a private guest retreat. The kitchen has been tastefully updated with new cabinetry and granite countertops, anchoring a bright, tiled main level built for effortless entertaining. Recently installed impact windows and doors on the first floor bring both peace of mind and energy efficiency, a significant upgrade in the islands. Upstairs, two additional bedrooms share a well-appointed bath beneath cozy carpeted flooring, while a versatile exterior porch off the second floor offers flexibility to enclose as a home office, additional storage, or a walk-in closet -- or simply enjoyed as-is for morning coffee in the island breeze. With no HOA or condo fees, ownership here comes with true freedom -- no added costs, no added rules. Sold unfurnished and ready for immediate occupancy, this home offers a seamless path to island living without delay. Located within easy reach of top schools and Key West's favorite shopping destinations, this is a rare opportunity to plant roots in the Keys without compromise. Welcome home to island living, made simple.

3206 Harriet Ave, Key West

$4,499,999
3 Beds 3 Baths 620745 MLS
Located in the Beach Club, this reimagined residence offers a rare combination of luxury, privacy, and oceanfront living within one of Key West's premier & financially secure condo communities. This 3 bed, 3 bath residence encompasses 2,309 sq ft of thoughtfully designed living space with views of the Atlantic Ocean. Offered fully furnished, every detail has been curated to blend contemporary elegance with the relaxed refinement of island living. A robust high-speed WiFi system with multiple access points & 800 Mbps of service enhances the home's modern convenience. Walls of pocket glass doors frame endless ocean vistas while filling the living spaces with natural light. Designer lighting, Hunter Douglas Luminette sheer window treatments, and exceptional craftsmanship are showcased throughout. The kitchen features Miele appliances, integrated cabinet lighting, custom-organized drawers, and an innovative smart-glass circular window connecting the kitchen and dining area. With the touch of a button, the glass transitions from opaque to transparent. Designed for both entertaining and everyday living, the open-concept living and dining areas flow seamlessly. The dining space is highlighted by striking brass architectural lighting, while a custom-built bar with a wine cooler and ice maker creates an inviting entertaining alcove. The terrace extends the living space outdoors, offering a comfortable setting to enjoy the surrounding views. The primary suite features a distinctive white oak accent wall, built-in workspace and vanity with concealed power outlets, a spa-inspired bath, generous closet space, dual shoe closets, and a private waterfront terrace. One guest bedroom doubles as a media room with designer floral wall covering and club chairs that convert into twin beds. The third guest bedroom is a spacious ensuite retreat offering comfort and privacy. Residents enjoy gated access, exceptional amenities, covered deeded parking space, & private storage.

1500 Atlantic Blvd Unit 308, Key West

$599,000
1 Beds 1 Baths 620722 MLS
Life feels a little slower in the Casa Marina neighborhood. Mornings begin with a walk to Higgs Beach, afternoons are spent by the pool, and evenings often end just down the street at Salute! on the Beach or Louie's Backyard. Tucked within the peaceful Southpark Condominium community, 816 South Street, Unit 4 places you in the heart of one of Key West's most desirable locations while offering the privacy and simplicity of low maintenance island living. Inside, this 1 bedroom, 1 bathroom condominium feels bright, comfortable, and welcoming. The open living spaces flow naturally to two private outdoor decks, one at the front of the home that is perfect for enjoying the neighborhood atmosphere and another tucked just off the bedroom, surrounded by mature tropical landscaping for a more private escape. The community itself offers the amenities that make everyday living feel like a vacation, including a beautifully maintained heated swimming pool set among lush tropical grounds. An assigned off street parking space and a spacious locked storage area provide conveniences that are increasingly valuable in Key West. Located just 4 blocks from Duval Street, you can easily walk or bike to beaches, restaurants, galleries, shopping, and everything that makes island life so special, while still returning home to one of the quieter residential pockets of Old Town. Whether you are searching for a full time residence, a seasonal retreat, or simply a place where life naturally slows down, 816 South Street, Unit 4 offers an opportunity to experience the very best of Casa Marina living.

816 S St Unit 4, Key West

$1,099,000
2 Beds 3 Baths 620653 MLS
One of the greatest luxuries in Key West isn't extravagance--it's finding a home where life feels a little quieter, a little easier, and a little more connected to the island around you. That's exactly what you'll find at 97 Seaside North Court. Tucked inside the often-overlooked gated Seaside Residences community, this light-filled townhome offers something increasingly difficult to find in Key West--privacy, space, and a sense of calm.Natural light pours through eight additional windows found only in some end units, while mature palms and established mahogany trees create a backdrop of green from every room. Whether enjoying a quiet morning coffee, working from home, or entertaining friends, the four opposing balconies welcome the island breezes and connect the home to its peaceful surroundings. Built with solid masonry construction, impact-rated windows and doors, 16 solar panels paired with a Generac battery storage system, and an elevator that services every floor, this home was designed with comfort, durability, and resilience in mind. The ground-level screened enclosure with a garden offers exceptional flexibility as a home gym, yoga studio, covered dining area, or entertaining space.Residents enjoy a secure, well-maintained community with resort-style amenities including a swimming pool and fitness center, all within easy reach of Smathers Beach, Key West's longest stretch of sandy beach. Built in 2005 on a larger-than-average lot, with 1,824 square feet of air-conditioned living space, three full baths, an outdoor shower, garage, and even a rooftop stargazing deck. 97 Seaside Court North is now offered at an exceptional value within Seaside Residences--an opportunity to enjoy one of Key West's most desirable gated communities without compromising on space, quality, or lifestyle.

97 Seaside N, Key West

$4,995,000
4 Beds 5 Baths 620618 MLS
Welcome to an extraordinary oceanfront residence in the exclusive Casa Caselles community, where two townhomes have been masterfully combined into one spectacular 4,224 sq. ft. luxury retreat with private interior elevator accessing all floors . Completely reimagined, this one-of-a-kind residence showcases exceptional craftsmanship, sophisticated design, and effortless waterfront living. Offering 4 en-suite bedrooms, 4.5 baths, 2 expansive living areas, an exercise room, and a hidden office seamlessly integrated into the custom kitchen, the home is designed for both everyday living and grand-scale entertaining. An oversized island anchors the chef's kitchen, complemented by custom European-style cabinetry, premium quartz countertops, and an impressive suite of appliances including a BlueStar gas range, paneled Sub-Zero refrigerator, Cove dishwasher, U-Line ice maker and wine refrigerator, and Perlick refrigerator/freezer drawers. The inviting family room features an electric fireplace and a custom wet bar with refrigerator drawers, dishwasher, and built-in cabinetry, creating an ideal space for entertaining. Throughout the home, travertine flooring, custom built-ins, abundant hidden storage, recessed lighting, remote-controlled window coverings, and in-wall TV wiring reflect meticulous attention to detail. Every major system has been replaced, including electrical, plumbing, insulation, HVAC systems, 12 hurricane-rated sliding glass doors, and a whole-house generator. The luxurious primary suite features a custom walk-in closet, while every bedroom enjoys private balcony access. A guest suite features a zero-entry shower, offering added comfort and accessibility. Beautifully tiled courtyards, expanded entertaining terraces, covered parking for four vehicles, an outdoor shower, and multiple laundry areas enhance everyday living. Residents enjoy an oceanfront pool overlooking the Atlantic, completing one of Key West's most distinctive waterfront residences.

1616 Atlantic Blvd Unit 11, Key West

$1,199,000
2 Beds 4 Baths 620515 MLS
Welcome to Seaside Residences, one of Key West's most sought-after gated communities. This beautifully updated three-story townhome is one of the largest residences in the community, offering 2 bedrooms, 3.5 bathrooms, 1,824 square feet of thoughtfully designed living space, making it the second-largest property in Seaside Residences. A private elevator services all three levels, providing both comfort and convenience. Enjoy the best island living with three private balconies offering beautiful sunrise and sunset views, plus a private rooftop deck perfect for relaxing, entertaining, or soaking up the Florida sunshine. The ground level features a private garage, laundry area, half bath, and a spacious outdoor patio complete with a tranquil fountain and fire pit--an ideal space for gathering with family and friends. The second level offers a spacious primary suite with an ensuite bath featuring dual vanities and a large walk-in shower, while the guest bedroom enjoys its own private full bath. The top floor showcases an open-concept living, dining, and kitchen area filled with abundant natural light. The kitchen features rich wood cabinetry, granite countertops, stainless steel appliances, generous pantry space, and an ideal layout for both everyday living and entertaining. Recent upgrades include a new air conditioning system, new water heater, and impact-resistant windows and doors throughout, providing peace of mind, energy efficiency, and storm protection. Residents enjoy exceptional community amenities including a resort-style pool, fitness center, and the convenience of building insurance covered through the HOA. Ideally located just steps beaches, Old Town Key West, world-class dining, shopping, marinas, and local attractions, this property also allows short-term rentals, making it an outstanding opportunity as a full-time residence, luxurious vacation home, or exceptional income-producing investment.

33 Seaside S Ct, Key West

$589,900
2 Beds 2 Baths 620466 MLS
Updated home in a prime central Key West location! Perfect for a local buyer or as an affordable second home in a quieter part of town, this move-in-ready property offers comfort, convenience, and tropical charm. The home features two generously sized bedrooms, two full bathrooms, and is situated on a corner lot in New Town. Warm wood flooring runs throughout, while the kitchen and dining area showcase Corian countertops, stainless steel appliances, classic wainscoting details, and a timeless neutral coastal palette that creates a bright, relaxed island atmosphere. French doors offer a bright and inviting living area and open to a composite deck and a lush, fully fenced yard, creating an ideal setting for indoor-outdoor living. Enjoy your morning coffee from the upstairs porch overlooking the tropical landscape, complete with a peek-a-boo view of the nearby park and recreational facilities. The private, gated yard is a true island retreat, featuring banana and mature mango trees that produce an abundance of fruit, vibrant bougainvillea, and an outdoor shower that's perfect after beach or boating days. Additional highlights include off-street parking, no HOA fees, and a welcoming townhome-style layout designed for easy living. Conveniently located near schools, shopping, beaches, grocery stores, sports fields, and movie theaters, this home offers the best of the Key West lifestyle, with everyday conveniences just a short walk or bike ride away.

3201 Pearl Ave, Key West

$950,000
2 Beds 2 Baths 620451 MLS
Coastal Living at 1800 Atlantic - where everyday life is framed by ocean breezes and turquoise water. This highly sought-after oceanfront condominium community offers the rare privilege of walking distance to Smather's Beach on the Atlantic, minutes from the airport, and the effortless ease that makes Key West living so desirable. Stroll along the shoreline in the morning, watch boats drift along the horizon, and spend your afternoons relaxing beside the resort-style Olympic-size heated pool and spa, all set within lush tropical landscaping. Residents enjoy tennis and pickleball courts, an equipped fitness center, assigned covered parking, and professionally maintained grounds--delivering true comfort, simplicity, and peace of mind in a coastal setting. Recent upgrades include impact-rated doors and windows, enhancing storm protection, energy efficiency, and long-term ownership confidence while maintaining a clean, modern coastal aesthetic. Pet owners will appreciate the flexibility of 2 pets allowed (up to 50 lbs total). Monthly association fees include building insurance, exterior maintenance, professional management, water, high-speed internet - offering a truly turnkey lifestyle. Ideally located just minutes from Old Town Key West, you're close to world-class dining, galleries, marinas, and cultural events, yet tucked away in a quiet, oceanfront enclave that feels removed from it all. Whether by bike or a short drive, everything the island offers is within easy reach. Come experience why so many call this their Key West home away from home 🌴.

1800 Atlantic Blvd Unit 218B, Key West

$665,000
2 Beds 2 Baths 620447 MLS
3200 Harriet Avenue | Key West, FL Tucked away on a desirable corner lot, this spacious 2-bedroom, 1.5-bath townhouse offers 1,332 square feet of comfortable living and one of the largest floor plans in the community. Combining privacy, generous living space, and exceptional outdoor amenities, this home is a rare find in Key West. One of the property's most appealing features is the absence of HOA fees, allowing you to enjoy all the benefits of homeownership without monthly association dues or restrictive community fees. It's a rare opportunity to own a spacious townhouse with the freedom and flexibility typically associated with a single-family home. Step outside to your own private pool, creating the perfect setting for entertaining, relaxing, or enjoying the tropical island lifestyle year-round. The corner-lot location provides added privacy and outdoor space, making this home feel even more secluded. Inside, the well-designed floor plan offers bright, inviting living spaces with plenty of room to gather, work from home, or simply unwind after a day on the water. Conveniently located in New Town, 3200 Harriet Avenue is just minutes from shopping, dining, schools, beaches, and all that Old Town Key West has to offer. Whether you're looking for a primary residence, vacation home, or investment property, this home delivers an outstanding combination of space, privacy, and the quintessential Key West lifestyle.

3200 Harriet Ave, Key West

$625,000
2 Beds 2 Baths 620312 MLS
One owner since new, this Key West Golf Club townhome has been maintained with a new roof, new A/C, and an updated kitchen and baths -- the major systems and finishes are already done. Tile runs throughout the first floor, which opens across the kitchen, dining, and living space, plus a half bath for guests. Upstairs holds two bedrooms and a full bath finished with durable, eco-friendly cork flooring -- a resilient, long-lasting surface prized for comfort underfoot and sustainability -- along with a permitted enclosure of the front balcony that adds livable space most units in the complex don't have, plus an in-unit washer/dryer and dedicated storage. Outdoor living wraps the home front to back: a covered front porch, two screened back porches, and a fenced yard built for grilling and entertaining. The community pool, gym, and Zen garden are steps away. The location is what sets this community apart. Key West Golf Club is the island's only gated golf-course community -- a Rees Jones-designed 18-hole course, on-site bar and grill, two pools, a fitness center, and 24-hour gated security. Old Town, the beaches, and the marinas are a quick car or bike ride away. HOA dues are reasonable and cover cable and common-area maintenance. Zoning allows 30-day minimum rentals, so the unit works for seasonal income, long-term tenancy, or part-time ownership. The numbers back it up: at 871 verified square feet, this is the largest 2-bedroom, 1.5-bath townhome currently listed in the community -- and at $718 per square foot, the lowest-priced per foot in its category. Owner financing may be considered for qualified buyers, adding flexibility rarely found in this market. One careful owner, move-in ready, priced to move, in a location that doesn't come around often. Schedule your private showing today.

1 Spoonbill Way, 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

$775,000
2 Beds 2 Baths 620157 MLS
TRANSIENT LICENCE RECEIVERSHIP ZONE! Welcome to your slice of paradise in Key West! This charming 2-bedroom, 2-bathroom condo located just steps from Duval Street offers an incredible opportunity. Currently utilized as an income-producing vacation rental, this home presents the perfect blend of comfort and convenience. Nestled in the heart of Key West, this condo boasts proximity to renowned attractions, vibrant restaurants, and the lively energy of Duval Street, ensuring endless entertainment options for residents and guests alike. Just a few blocks away lies Key West's South Beach, where sun-soaked days and breathtaking sunrises await. The interior of this inviting condo features two spacious bedrooms, providing ample room for relaxation and rejuvenation after a day of exploring the island. The well-appointed bathrooms offer both style and functionality, catering to the needs of residents and visitors. Whether you're lounging on the private balcony, enjoying the tropical breeze, or venturing out to experience the vibrant culture of Key West, this condo offers the quintessential island lifestyle. Don't miss your chance to own a piece of paradise and capitalize on the flourishing vacation rental market in this coveted location. Seize this opportunity to invest in Key West living at its finest. Schedule your showing today and envision the endless possibilities that await in this delightful condo just steps from Duval Street!

508 Louisa St Unit 3, Key West

$1,279,000
2 Beds 4 Baths 620140 MLS
Welcome to one of the most sought after gated communities in Key West Seaside Residences. This beautiful updated 2-bedroom 3.5 half bath offers 1824sq. ft of living space. It is a three-level townhouse with your own private elevator that accommodates all three levels. You have four private balconies on the top two floors which gives you a perfect view of the beautiful sunrises and sunsets. Not to mention that the roof deck has its private surroundings for beautiful views of the Atlantic Ocean and suntanning. On the first floor you will pull up to your private garage. There is also your laundry and half bath with Air conditioning. The rest of the first floor is your Bar/BBQ and ample space for entertaining your family and guests. This townhome comes with one of the few units with extra side yard which is turf with a putting green. Moving to the second floor there is your primary suite and ensuite bathroom with double vanities. There is a large shower for relaxing. Second bedroom also has its private full bath. Third floor opens to the main living room ocean view which flows to the dining room. The Kitchen features wood cabinetry with lots of storage. Granite countertops. Stainless Appliances and plenty of pantry storage, there is abundance of natural sunlight that flows across from large windows and doors. Townhouse comes with all impact hurricane windows and doors. Washer and dryer are fairly new (2023) and tankless water heater as well (2023). Air Condition replaced in September of 2023. (Priced to Sell). Included in your HOA fees are your insurances, pool and fitness center. Owner does hold a Florida Real Estate License

25 Seaside South Ct, Key West

$1,425,000
2 Beds 2 Baths 620045 MLS
***$10k BUYER INCENTIVE with a closing by 9/15/26*** Experience quintessential island living in this stunning waterfront townhome at Flagler's Landing, where sweeping Gulf views meet a central Key West location with private boat dockage. This elevated residence offers ~1,387 sq ft of living space with open water views from the main living areas, private balcony, and both upstairs bedrooms. Designed for effortless entertaining, the main level features an open-concept layout with spacious living and dining areas. The gourmet kitchen anchors the space with a custom coral stone island (seating for six), custom cabinetry, under-cabinet lighting, premium GE appliances, a six-burner range, and a new refrigerator. Warm bamboo flooring, recessed lighting, and a wide waterfront balcony create an ideal indoor-outdoor flow for sunsets and ocean breezes. A powder bath completes this level. A spiral staircase leads to the second level, where the hallway offers built-in bookshelves and a front-facing balcony. Both serene bedrooms feature walk-in closets and expansive water views. The primary and guest suites share a full bath with a glass walk-in shower, large vanity, and jacuzzi-style tub. Additional features include central A/C, ground-level covered parking, dedicated storage, a laundry area, and a ground-floor brick patio. For boating enthusiasts, the property includes a private shallow-draft slip suitable for a ~24 ft boat. Residents also enjoy community access to a heated concrete pool. Situated near beaches, dining, shopping, and marinas, this home is a rare opportunity to own a piece of paradise in an exclusive Key West enclave.

9 Mccoy Cir Unit 9, Key West

$3,500,000
3 Beds 3 Baths 619959 MLS
Located within the quiet, gated security of Old Town Villas, this 3-bedroom, 3-bathroom townhome offers a sophisticated, low-maintenance island retreat just one block off of Duval St. Built in 2017, with solid concrete construction, this exceptional residence blends contemporary elegance with a thoughtfully designed layout that maximizes privacy, comfort, and functionality. Stepping inside, the interior is highlighted by beautiful tile flooring that runs seamlessly throughout. The main level features an open-concept layout with a spacious living room and chef's kitchen complete with stainless steel appliances and granite peninsula offering abundant prep space and casual seating. Just off the kitchen, a flexible-use room can serve as a dining area or private bedroom suite, complete with its own ensuite bathroom. A hallmark of this property is the extensive amount of premium, custom-built cabinetry and shelving installed throughout by the California Closets, offering unparalleled storage and organization. For effortless luxury, a private elevator services all four levels, transporting you from the two-car garage all the way to the rooftop terrace. The third floor hosts two spacious ensuite bedrooms, each featuring private balconies and large walk-in closets complete with custom organizational systems. The top floor is dedicated to an open living room and office area--a flexible bonus space filled with natural light. Step out from this upper lounge onto the spectacular rooftop terrace, equipped with custom awnings for comfortable shade, designed to capture both sunrise serenity and vibrant sunset views. For total peace of mind, the home features impact-rated windows and doors throughout. Beyond your front door, enjoy the exclusive community amenities, including a large pool and cabana. Conveniently situated near the very best dining and boutiques Key West has to offer, this home delivers the ultimate blend of privacy, location and the coveted Key West lifestyle.

141 Simonton St, 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

$1,025,000
2 Beds 2 Baths 619778 MLS
This spacious two-bedroom, two-bath penthouse condo boasts a stunning balcony with ocean views, making it the perfect place to relax and enjoy the breathtaking scenery. The beautifully designed kitchen features a breakfast bar, granite countertops, and stainless steel appliances, making it a chef's dream come true. The stunning living room and dining room are flooded with natural light, creating a bright, inviting space perfect for entertaining guests. The floor-to-ceiling windows allow the natural light to pour in and are complemented by the soaring cathedral ceilings, which add an extra layer of grandeur and elegance to the space. Ample storage throughout ensures you'll have plenty of space to store all your belongings and keep your new home tidy and organized. The best feature of this penthouse is the breathtaking sunrises you'll enjoy over the Atlantic Ocean. Whether you're sipping your morning coffee or simply taking in the view, this condo will provide the perfect setting for relaxation and rejuvenation. The complex: One of the best parts of 1800 Atlantic is its private beach. You can soak up the sun, enjoy the stunning ocean views, or dip in the Olympic-sized heated pool while relaxing within this gated and secured oceanside community. For those who love staying active, three lighted tennis courts are perfect for a friendly game with friends or a competitive match, and the fitness center is fully equipped with everything you need to stay in shape and achieve your health goals. With storage and covered garage parking, you'll have plenty of space to keep all your belongings safe and secure. With its tropical resort-style setting and luxurious amenities, 1800 Atlantic is the perfect place to call home.

1800 Atlantic Blvd Unit 427C, Key West

$575,000
3 Beds 2 Baths 619747 MLS
Experience the relaxed charm of island living in this nicely updated third-floor 3-bedroom, 2-bath condo located in the highly desirable Las Salinas community. Filled with natural light, the open-concept layout creates a bright and welcoming atmosphere that feels comfortable from the moment you walk in. The thoughtfully designed kitchen features quartz countertops, stainless steel appliances, and a convenient washer/dryer combo, all opening to a spacious living and dining area perfect for entertaining or simply unwinding after a day on the water. Step outside to your private balcony overlooking the community pool -- an ideal spot for morning coffee, peaceful evenings, and enjoying the island breeze. The primary suite includes a private en-suite bath, while the additional bedrooms offer generous closet space for comfortable everyday living. An exterior storage locker provides extra room for bikes, beach gear, and all your island essentials, adding even more practicality and value. Residents of Las Salinas enjoy resort-style amenities including a large sun-drenched swimming pool, newly updated fitness center, bike storage, and lush tropical landscaping -- all with one of the lowest HOA fees in Key West, including insurance. Ideally located on the east side of the island, you're just moments from Smathers Beach, restaurants, shopping, and Key West International Airport. The nearby scenic promenade along the Atlantic Ocean is perfect for biking, jogging, or taking peaceful morning walks while enjoying breathtaking Keys sunrises. Whether you're searching for a full-time residence, vacation getaway, or smart investment property, this condo offers the easygoing lifestyle people dream about when they think of Key West.

3930 S Roosevelt Blvd Unit N304, Key West

$2,445,000
2 Beds 3 Baths 619742 MLS
Discover a rare blend of history, artistry, and luxury in this extraordinary residence at the celebrated William Fleming House--one of Old Town Key West's most iconic and meticulously restored historic buildings. Originally constructed in the 1890s as Peacon's General Store, this architectural treasure has been transformed into an exclusive boutique condominium, exquisitely and entirely renovated. Inside, the first level condo rises to an unforgettable 16 feet, creating a sense of openness and serenity that feels both dramatic and inviting. Sunlight pours through impact-rated windows and doors, illuminating the vintage wood flooring and expansive walls that are ideal for showcasing meaningful art and personal collections. The thoughtfully designed layout includes two bedrooms, two full bathrooms, a half bath and a versatile loft space- accessed by a traditional staircase--offering remarkable flexibility for work, guests, creative pursuits, or quiet retreat. A private outdoor deck extends your living space and provides a peaceful spot for morning coffee or evening unwinding. The William Fleming House elevates daily living with its heated outdoor pool, lush tropical landscaping, and assigned off-street parking. Located in the desirable X-flood zone and directly across from Williams Hall, this residence places you in the heart of Old Town's cultural and architectural richness. With its unmatched scale, history, and character, this home invites you to bring your vision and transform it into a truly exceptional Key West sanctuary--one that reflects your style, your story, and your sense of place.

800 Fleming St Unit Unit C1, Key West

$760,000
2 Beds 2 Baths 619590 MLS
Substantial price improvement. Motivated seller. This well-maintained 2-bedroom condo has just hit the market and is truly priced to sell. Offered turnkey and newly furnished in 2017, the unit features a bright, inviting living space with a tiled main living area and two generously sized bedrooms. The primary suite includes its own ensuite bath for added comfort and privacy. A standout feature is the spacious balcony that spans the full length of the unit--perfect for relaxing or entertaining--with direct access from both bedrooms and the living room. The kitchen and bathrooms retain their original finishes, offering a fantastic opportunity to customize and upgrade to your personal style. The condo includes a full-size, fully equipped kitchen, in-unit washer and dryer, and high-speed wireless internet for modern convenience. You'll also enjoy one assigned covered garage parking space along with a private storage area conveniently located just in front of it. This desirable waterfront complex offers resort-style amenities, including a stunning Olympic-size heated pool, relaxing jacuzzi, well-equipped fitness center, and beautifully landscaped botanical gardens. Tennis lovers will appreciate three lighted courts, including a clay court. Additional perks include visitor parking and on-site security. Ideally situated next to Smathers Beach on the Atlantic side of Key West, 1800 Atlantic is just two miles from downtown and Mallory Square. Whether you're seeking a full-time residence, an investment property, or a winter retreat, this is an exceptional opportunity to own in one of Key West's most sought-after communities.

1800 Atlantic Blvd Unit C223, Key West

$679,500
2 Beds 2 Baths 619544 MLS
Welcome to your slice of paradise in the highly sought-after Key Cove community in Key West, FL, where island living meets enjoyable comfort. This beautifully designed townhome offers the perfect blend of coastal charm and modern convenience. Featuring a bright, open-concept layout, the living and dining spaces flow seamlessly with the well appointed kitchen. Ideal for entertaining or unwinding after a long day. Enjoy outdoor living with the covered balcony off of the living room. The Living Room & Foyer has updated Engineered Hardwood - European French Oak Flooring in March 2023. Kitchen Tile updated in August 2025. The stairs and Hallway have Hardwood flooring as well updated in June 2021. New Hot Water Heater in August 2025 along with updated Kitchen Light and Faucet in March 2026. Most of the rooms in the home have been freshly repainted with Sherwin Williams Paint. Upstairs features two spacious bedrooms with high ceilings. A gorgeous bathroom with plenty of light. There's also a hall laundry room for easier lifestyle duties. This home features covered parking with a garage door. Plenty of space underneath for extra storage. Key Cove residents love the laid-back lifestyle. Convenient location for food shopping, dining and entertainment. Also, there's a Community Pool to hangout and enjoy your day. Whether you're searching for a full-time residence or a second home, this home delivers the Key West lifestyle you've been waiting for and more.

3029 N Roosevelt Blvd Unit APT 11, Key West

$609,000
2 Beds 1 Baths 619408 MLS
**Golf course frontage. No rear neighbors. Minutes to Old Town Key West.** Welcome to your island retreat in the sought-after Key West Golf Club community on Stock Island. Overlooking the first green of the Rees Jones-designed golf course, this beautifully updated 2-bedroom, 1.5-bath home offers a rare combination of privacy, scenic views, and resort-style living. Inside, the 780-square-foot home features waterproof flooring, crown molding, and a renovated kitchen and full bath (2021) with modern finishes and appliances. Additional upgrades include a WiFi-enabled LG laundry center, whole-home water filtration system, and Bahama shutters that enhance the home's classic island charm while providing added storm protection. Relax on the screened rear porch overlooking the first green--perfect for morning coffee or evening cocktails. The guest bedroom also features a private front balcony to enjoy the island breeze. Ideally located directly across from the community's large lagoon-style pool, fitness center, HOA office, and butterfly garden, this home offers convenient access to the neighborhood's premier amenities. HOA dues include community maintenance, high-speed fiber optic internet, and DIRECTV streaming service within this gated community. Whether you're looking for a primary residence, vacation home, or income-producing investment, this property offers exceptional flexibility with 28-day minimum rentals permitted with the required City of Key West license. Street parking for two vehicles adds everyday convenience. Enjoy peaceful golf course living just minutes from the restaurants, shops, waterfront, and nightlife of Old Town Key West and Duval Street. **Now offered at $609,000.** Owner is a licensed Florida real estate agent and the listing agent.

81 Golf Club Dr, Key West

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