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2911 Seidenberg Ave, Key West
$1,100,000
3 Beds ⋅ 2 Baths ⋅ 621482 MLS
Welcome to your dream home in the heart of Key West's MidTown! This beautifully updated 3-bedroom, 2-bathroom residence blends modern comfort with island charm. Step inside to a spacious, open-concept living area designed for both relaxing and entertaining. The true highlight is the private backyard oasis -- featuring a sparkling pool surrounded by fresh tropical landscaping, an expansive deck, and plenty of room for outdoor dining and lounging. Whether hosting guests or enjoying a quiet evening under the palms, this outdoor retreat feels like your own private paradise. Recent renovations provide peace of mind, including new impact windows and doors, Hardie board siding, and other thoughtful upgrades. Off-street parking adds everyday convenience. Perfectly located in the desirable MidTown neighborhood, this home keeps you close to shopping, dining, and all the best of Key West living. Don't miss this opportunity to own a beautifully updated slice of paradise in Key West -- schedule your private showing today!

2911 Seidenberg Ave, Key West
927 Thomas St Unit 1, Key West
$1,133,000
2 Beds ⋅ 3 Baths ⋅ 621479 MLS
Your Old Town Key West dream can start now -- with income built in. This exceptional 2-bedroom, 2.5-bath, townhouse-style condo offers a rare combination of Old Town lifestyle, flexible living space, and income-producing potential. Currently configured with a lock-off 1-bedroom apartment, the property offers an ideal opportunity for the future Key West homeowner: enjoy the larger 1 Bedroom, 1.5 Bath unit with private garden/patio as your own Key West retreat while the lock-off apartment provides substantial annual rental income. When the time comes to make Key West your full-time home, the property can be easily converted back to its original spacious 2-bedroom townhouse-style layout. A private gated entry opens to your own generous outdoor oasis, complete with a waterfall pond, large patio, and charming ''she-shed'' -- perfect for storage, an art studio, or entertaining. Inside, you'll find high ceilings, abundant natural light, generous storage, in-unit washer/dryers, and newer stainless-steel appliances. Just two blocks from Duval Street in the heart of Old Town's vibrant Bahama Village, you're surrounded by restaurants, galleries, shops, nightlife, and countless Key West attractions -- all within easy walking distance. Whether you're ready for a Key West home now or envision making the island your full-time home in the future, this is a rare opportunity to own your piece of Old Town, enjoy income along the way, and ultimately create the spacious Key West home you've been dreaming of. Some seller financing considered. Seller is a Florida Licensed Realtor. Photos 10-17 show Original Layout, 18=FloorPlan, 19-37 show Back Unit, 38-49 show Front Lock-Off Apt.

927 Thomas St Unit 1, Key West
1401 Atlantic Blvd, Key West
$3,295,000
5 Beds ⋅ 4 Baths ⋅ 621476 MLS
Discover the perfect blend of transient investment potential and coastal charm on Atlantic Boulevard. Just steps from the beach, this exceptional property offers a truly enchanting lifestyle with a distinctive boho-coastal aesthetic. The Atlantis House featuring five bedrooms and four bathrooms across three thoughtfully curated living spaces, this one-of-a-kind compound combines character, comfort, and style with an exciting opportunity for transient rental income. The primary residence is an exquisite 3-BR/2-BA monthly rental boasting a light-filled, open-concept floor plan for effortless island entertaining. You are welcomed into a mosaic-tiled foyer featuring whimsical swinging hammock chairs and a charming custom scooter coffee bar, flowing into spacious living areas adorned with timeless terrazzo floors. The heart of the home is a true gourmet kitchen, featuring a large island, pristine white quartz countertops, and separate Sub-Zero refrigerator and freezer. The main level offers two luxurious bedrooms opening to a beautifully landscaped fenced yard with a bistro patio. A spiral staircase leads upstairs to a third bedroom--a spectacular oasis with open water views. This level features dual sliding doors opening onto a magical, Trex rooftop terrace with a dining pergola and views of the Atlantic. It is the perfect perch to watch the sunrise with coffee in hand and return for the sunset. Around the corner are two detached, transient-licensed 1BR/1BA guest suites with dedicated parking. Both offer tasteful decor and private access to a backyard oasis with a large shared deck shaded by towering palms. Live the ultimate Key West lifestyle, a stone's throw from launching your kayak at the beach and a one-minute walk from the iconic White Street Pier. The Atlantis House conveys with its own house-made Atlantis Key Lime Pie recipe, passed from the former owner to the new owner, a tradition carried for more than 30 years. A one-of-a-kind treasure!

1401 Atlantic Blvd, Key West
1901 S Roosevelt Blvd Unit 208E, Key West
$1,349,000
3 Beds ⋅ 2 Baths ⋅ 621474 MLS
Ocean Views & Island Living at La Brisa - Key West. Wake up to ocean views and embrace the Key West lifestyle! Rarely available, this 3-bedroom, 2-bath condominium in the gated La Brisa community offers direct ocean views and an exceptional location directly across from Smathers Beach. Whether you're looking for a full-time residence, a seasonal island retreat, or an investment opportunity, Unit 208E offers an inviting combination of coastal living, everyday comfort, and resort-style amenities. The open-concept living and dining areas flow seamlessly into the updated kitchen, creating a bright, welcoming space for relaxing or entertaining. Sliding glass doors lead to a private balcony where you can savor your morning coffee, enjoy the ocean breeze, and take in the beautiful water views. The primary suite is a peaceful retreat, featuring ocean views through a large picture window, direct balcony access, generous closet space, and a private en-suite bath. Two additional bedrooms provide flexible space for family and guests or even a home office Convenience is built in, with assigned covered parking and a dedicated storage area located next to the elevator. La Brisa is a professionally managed, gated community known for its well-maintained grounds and impressive amenities, including a heated swimming pool, hot tub, saunas, clubhouse, lighted tennis/pickleball court, car wash area, grilling area, and complimentary EV charging station. Just steps from Smathers Beach and close to bike paths, Key West International Airport, local restaurants, and the island's many attractions, this condominium puts the best of Key West within easy reach. Your island lifestyle starts here. Experience the ocean views, enjoy the amenities, and make Unit 208E at La Brisa your own. Move-in ready and available for immediate occupancy.

1901 S Roosevelt Blvd Unit 208E, Key West
1212 Olivia St, Key West
$2,475,000
3 Beds ⋅ 2 Baths ⋅ 621462 MLS
Discover the charm of what was once a carriage house and now a single-level home nestled in the highly desirable Meadows neighborhood of Old Town Key West. This inviting 3-bedroom, 2-bath residence blends historic character with modern updates, offering the quintessential island lifestyle. Effortless indoor-outdoor living defines this home, which features an open, airy feel that flows seamlessly to a private backyard oasis. The renovated kitchen features quartz countertops, modern finishes perfect for entertaining or everyday living. A versatile bonus loft provides the ideal space for a home office. Step outside to your own tropical retreat, complete with a sparkling pool surrounded by a spacious brick patio, cabana bar, fabulous outdoor shower and mature landscaping that creates privacy and a lush island ambiance. Topped off with off-street parking, whole house generator, x flood zone and close proximity to everything that makes Key West living so special, while still providing a peaceful neighborhood setting. This is truly a gem waiting to become your tropical island home!

1212 Olivia St, Key West
3312 Northside Dr Unit APT 707, Key West
$499,000
2 Beds ⋅ 2 Baths ⋅ 621440 MLS
Stunning Renovated 2-Bedroom Condo with Panoramic Ocean Views - Key West, FL Welcome to your slice of paradise! This beautifully renovated 2-bedroom, 2-bath condo on the 7th floor offers breathtaking, unobstructed ocean views and the best of island living in Key West. Step inside to find a bright and airy open-concept living space, complete with modern finishes, sleek tile flooring, and expansive windows that flood the unit with natural light. The updated kitchen features granite countertops, stainless steel appliances, custom cabinetry, and a stylish backsplash--perfect for entertaining or relaxing with a view. The spacious primary suite includes ocean views, a nice closet, and a en-suite bath. A second bedroom and full bathroom make this an ideal space for guests or a home office. Enjoy your morning coffee or evening wine from your private balcony overlooking the turquoise waters of the Atlantic. The condo also offers resort-style amenities including a pool,secure entry, and open parking. Located just minutes from Key West's world-class dining, shopping, and entertainment, this condo is your dream home in the heart of the island. Whether you're looking for a full-time residence, vacation getaway, or investment opportunity, this one has it all. Don't miss your chance to own this ocean-view gem--schedule a private showing today!

3312 Northside Dr Unit APT 707, Key West
1901 S Roosevelt Blvd Unit N104, Key West
$849,000
2 Beds ⋅ 2 Baths ⋅ 621436 MLS
Coastal Living at Its Finest - 2-Bedroom Condo at La Brisa ! Wake up to ocean breezes in this beautifully appointed 2-bedroom, 2-bathroom condo located just steps from Smathers beach. Situated directly across the street from the shoreline, this bright and airy residence offers the perfect blend of comfort, convenience, and coastal charm. Inside, you'll find a spacious open-concept living and dining area filled with natural light, a modern kitchen , and two generously sized bedrooms with ample closet space. The primary suite features a private en-suite bathroom, while the second bedroom is ideal for guests or a home office. Relax on your private balcony with peaceful Salt Pond views, or take a short stroll across the street to sink your toes in the sand. This condo also offers amenities such as assigned parking, in-unit laundry, and access to a community pool, tennis courts and clubhouse. Perfect as a primary residence, weekend retreat, or investment property--this is beachside living made easy! Call for your private tour today !

1901 S Roosevelt Blvd Unit N104, Key West
197 Golf Club Dr, Key West
$1,350,000
3 Beds ⋅ 3 Baths ⋅ 621423 MLS
Welcome to the Sanctuary! This UPDATED/REMODELED gated single family POOL home is located on the 18th hole of the world famous Rees Jones designed Key West Golf Course. 1600 sq ft of living space with 3 bedrooms and 2.5 bathrooms. This 2 story home features an open floor plan with 9 ft ceilings and lots of windows allowing in natural light. An updated half bath is conveniently located on the first floor. The kitchen was updated with Calcutta Quartz countertops, ceramic plank tile backsplash resembling a weathered coastal wood and stainless steel Cafe appliances. Travel up the stairs with new Bamboo flooring to 3 bedrooms and 2 more updated baths. The Primary Suite features a Spa Like Escape bath with waterfall shower. French doors off the Primary Suite open to a screened balcony porch with views of tropical foliage and private pool. The pool was recently resurfaced and the pool pump and pool heater replaced. Sprinkler system also replaced. Freshly painted exterior. 24 hour security, fitness room, additional community pool are just a few of the amenities this property offers. You don't want to miss this beautiful turn key home in one of the most tranquil settings in Key West. It's a true Coastal Charmer!

197 Golf Club Dr, Key West
3316 Harriet Ave, Key West
$535,000
2 Beds ⋅ 2 Baths ⋅ 621365 MLS
Priced to sell and one of the most affordable opportunities in the popular Key West Estates! 3316 Harriet Avenue is an excellent option for a first-time homebuyer, investor, or workforce housing, offering NO HOA fees, deeded parking, shed, screened in covered porch, air-conditioning, and a private fenced outdoor area complete with landscaping. Conveniently located in New Town near shopping, schools, recreation, and everything Key West has to offer! This property provides a rare opportunity to own in Key West at an approachable price point. Schedule a showing today!

3316 Harriet Ave, Key West
626 Fleming St Unit A, Key West
$1,299,000
3 Beds ⋅ 3 Baths ⋅ 621356 MLS
Beautifully renovated 3bd/2.5ba townhouse incredibly located just 1.5 blocks from Duval Street with off street parking. The first floor is dedicated to an open concept living room and kitchen with built in custom banquette for dining and extra storage. Off the kitchen you will find a covered screened in patio for outdoor living or dining. The second floor features 2 bedrooms , balcony and a newly renovated full bathroom. Enjoy custom fit closets throughout to maximize storage. The 3rd floor is a private oasis dedicated to the primary suite with newly renovated full bathroom, laundry and more custom storage. You will appreciate details that create a hassle free investment including CBS construction, new metal roof, central a/c, recessed lighting, skylights, custom plantation shutters, brand new impact windows and doors. Come take a look at this perfectly located slice of paradise.

626 Fleming St Unit A, Key West
1220 Newton St Unit 5, Key West
$779,000
4 Beds ⋅ 2 Baths ⋅ 621353 MLS
Welcome to 1220 Newton Street, Unit 5, located in the beautiful Meadows neighborhood of Key West's Historic Old Town. For those looking for space and value in Key West, this four-bedroom, two-bathroom home is a rare find. Featuring impressive 10-foot ceilings, original hardwood floors, and plenty of natural light, the residence spans the second and third floors of this classic Conch mansion. Step inside to a bright and comfortable living room with an abundance of natural light. A great space to relax, entertain, or simply enjoy being home. The kitchen is conveniently located just off the main living area. Also on this level is a generously sized bedroom with French doors that could easily serve as a home office, den, or game room. A full bathroom is just around the corner and completes the main level. Upstairs, you'll find three additional bedrooms and a second full bathroom, providing separation and privacy from the main living areas below. This property offers plenty of flexibility as a full-time residence or investment property with the potential for long-term rental income. Call today to schedule your private showing!

1220 Newton St Unit 5, Key West
3615 Eagle Ave, Key West
$2,895,000
3 Beds ⋅ 4 Baths ⋅ 621305 MLS
Some homes in Key West give you a view. This one gives you an entire private world. Tucked behind its own gates on a lush 12,000-square-foot lot, 3615 Eagle Avenue is a custom-built retreat where a botanical garden isn't a backyard feature -- it's the whole point. Mature native palms, flowering tropical plants, and a resident population of birds and butterflies surround the home on every side, and nearly every room has been designed to keep that view in constant reach, with walls of impact-rated glass doors blurring the line between inside and out. Inside, cathedral ceilings and wide-plank tile floors set a calm, airy tone across sweeping one-level living space. The kitchen is built for people who actually cook and entertain -- Sub-Zero refrigeration, a gas range, dual dishwashers, a wine cooler, and an ice machine, all within reach of the garden views. The primary suite sits privately at the front of the home, paired with a fully renovated spa-style bath. A flexible office/den off the main living space easily converts to a fourth bedroom for guests, in-laws, or a work-from-home setup. Step outside to a covered pavilion overlooking a heated 33-foot pool and spa, connected by a sand pathway that winds through the garden -- an entertaining space that feels more resort than residential. A generator, oversized double-car garage with built-in storage, and covered parking for three additional vehicles round out the practical side of island living. Property includes 2 Rogos on Double Lot, allowing for a second structure to be built. This is a rare offering: real privacy, real green space, and real craftsmanship, minutes from everything that makes Key West Key West.

3615 Eagle Ave, Key West
3312 Northside Dr Unit APT 407, Key West
$430,000
2 Beds ⋅ 1 Baths ⋅ 621283 MLS
First time on the market since 1982. Santa clara condo building has been totally renovated with its 40 year inspection completed with no assesments to worry about This 2 bedroom 2 bath has all the updates and has tenants paying $ 3100 per month . The tenants would like to stay . Need at least 24 hrs to show . Owners are license realtors

3312 Northside Dr Unit APT 407, Key West
611 Grinnell St Unit 6, Key West
$950,000
2 Beds ⋅ 1 Baths ⋅ 621278 MLS
Grinnell Street is often said to be one of the best streets to live on in Old Town, and this charming 2-bedroom home makes it easy to see why. Tucked away in a small, quiet association of just seven residences, the property offers a peaceful setting right in the heart of Old Town, Key West. Inside, the home is bright and beautifully updated, with plenty of natural light throughout. The kitchen has been tastefully updated with crisp white cabinetry, quartz countertops and stainless steel appliances. The spacious primary bedroom is filled with natural light, while the second bedroom is perfect for guests, a home office, or both. A beautifully renovated bathroom and new A/C units complete the interior. One of the best parts of this home is the outdoor space. There are several private areas to lounge and unwind, along with your own outdoor dining space for enjoying morning coffee or dinner outside. A grill on site makes it easy to cook and entertain without ever having to leave home. The association also features a large heated swimming pool surrounded by beautiful landscaping, perfect for cooling off after a bike ride through Old Town. The home is being offered fully furnished and has future bookings already in place should the new owner wish to continue renting. Walk to neighborhood coffee shops, some of Key West's best restaurants and shops, the Historic Seaport and everything Old Town has to offer. Quiet, charming and incredibly well located, this is an easy Key West home to fall in love with.

611 Grinnell St Unit 6, Key West
613 Margaret St, Key West
$5,400,000
6 Beds ⋅ 7 Baths ⋅ 621215 MLS
Step back into timeless Key West soul, where leaf-stamped garden paths, sun-dappled outdoor showers, and the gentle trickle of private pool waterfalls create an unforgettable Old Town sanctuary. Hidden behind a classic wooden gate just moments from the Historic Seaport and Duval Street, this compound offers two private, fully equipped homes on a lush 7,796-sq. ft lot, providing the ultimate luxury island retreat or multi-generational estate. Verdant foliage frames the wrap-around front porch of the front cottage, inviting you to sit back and enjoy quintessential island living. Inside, sky-lit vaulted ceilings with exposed wooden beams pour warm sunshine across white-painted walls and rich wood floors. The light-filled layout centers around an enchanting cottage kitchen filled with warmth and timeless charm that flows seamlessly into the living space and guest half bath. Three bedrooms-each featuring its own private ensuite bath-offer exceptional comfort. Floor-to-ceiling glass draws you out to an outdoor dining area and a sparkling heated pool nestled among vibrant gardens. Wander through the botanical grounds to the rear house, a custom-crafted two-story sanctuary built in 2016. Showcasing exquisite Hickory hardwood floors, whitewashed Cypress interior walls, and slate-tiled baths, this home balances coastal elegance with high-end luxury. The chef's kitchen boasts an elite ILVE range and custom cabinetry, flowing into open living quarters that slide open to the backyard oasis. The main floor offers versatile living with a guest suite that double-functions as a private home office with a built-in Murphy bed. Upstairs, a Craftsman staircase leads to a secondary guest suite with an ensuite bath and a sprawling primary retreat, complete with an oversized spa bath and a private balcony overlooking the second heated waterfall pool. Do not miss this rare chance to own one of Old Town's premier dual-home properties, complete with dedicated off-street parking for two cars.

613 Margaret St, Key West
516 Elizabeth St, Key West
$1,890,000
2 Beds ⋅ 3 Baths ⋅ 621199 MLS
Nestled in the heart of Old Town Key West, this historic gem boasts an impeccable blend of classic architecture and modern amenities. With a rich history dating back to the late1800's, this captivating residence offers the perfect opportunity to own a piece of Key West's storied past. Listed on the National Register of Historic Places and awarded the Gold Star for Historic Preservations, 516 Elizabeth St. is the perfect example of a Classical Revival Eyebrow House - a style unique to Key West. The roof overhangs over the second floor windows onto classic porch columns giving the suggested appearance of 'eyebrows' providing protection from rain and sun allowing the inside to have fresh air even during the hot summer months. Upon entering the home, original Dade County pine walls, high 10ft ceilings, original double hung wooden windows exude the timeless elegance of a bygone era. While preserving its historic character, this home has been thoughtfully updated with modern amenities. The kitchen features custom wooden cabinets and stainless steel appliances and all bathrooms are beautifully renovated. Enjoy the convenience of contemporary living without compromising on the historic appeal. The primary bedroom and bathroom upstairs provide a tranquil retreat, and the guest bedroom downstairs with it's own bathroom is convenient and comfortable. French doors lead from the formal dining room and kitchen to a sundeck with a covered dining area and extra lounging space to entertain. A Pool with water feature and new decking was just added to the property. This home has a rich history, with tales of past occupants, the Pinder family, and the unique stories of its heritage adding an extra layer of prestige and historical significance to its charm. This historic home is a rare find in a prime location, offering the best of both worlds. The house has some monthly vacation rental history and is sold furnished (some personal pieces & all art work excluded)!

516 Elizabeth St, Key West
714 Olivia St Unit # 6, Key West
$1,225,000
1 Beds ⋅ 1 Baths ⋅ 621189 MLS
A TRANSIENT LICENSED vacation rental located in the heart of Old Town Key West, the X flood zone and just 2.5 blocks from world famous Duval Street. The transient license allows for nightly rentals. A savvy investor could pounce on this rare opportunity to own a well-managed income producing property with excellent history & immediate income. Unit 6, aka Hidden Oasis, is 1 of only 11 units within the coveted enclave known as The Colony which features a large heated community pool, shared off-street parking and a gated entry to the pool area & the unit, all managed by the HOA. Hidden Oasis has a prime location within the community tucked into the back left corner with an entry deck and an abundant private rear deck that includes exclusive use of umbrella seating for 4, a propane grill, a full size washer & dryer and an outdoor shower stall. This well maintained unit has an updated kitchen, bathroom and mini-split air conditioning. The living area is light & airy with transom windows, vaulted ceilings and a well-appointed open kitchen. The spacious bedroom features a king sized bed, tropical décor and access to the front deck. Pride of ownership is obvious when you review the recent history of this owner managed HOA. The community pool was resurfaced in 2023, all buildings had new metal roofs installed in 2021 and all buildings were termite tented August 2026. Take advantage of this rare opportunity for an excellent Key West investment with an owner use option. With local property management & HOA management already in place, Hidden Oasis makes for an immediate complete turnkey 'hands-free' vacation rental ownership choice for a remote owner. Sold furnished with future bookings.

714 Olivia St Unit # 6, Key West
1427 Washington St, Key West
$2,525,000
4 Beds ⋅ 3 Baths ⋅ 621162 MLS
Set on a quiet, tree-lined block in one of Key West's most sought-after residential pockets, this thoughtfully reimagined 4BD/3BA residence offers just over 2,000 square feet of refined island living -- the result of a multi-year renovation where no detail was overlooked. The first floor opens to a flexible bedroom or private office alongside a full bath, newly converted and finished to the same standard as the rest of the home. Beyond, an all-new updated kitchen anchors the space with stainless appliances, custom built-in cabinetry, fresh countertops and designer lighting. French doors wrap the open living room, flooding the interior with natural light and dissolving the line between inside and out. Step through to your private tropical oasis: a heated pool, newly resurfaced and framed in travertine, with a new outdoor shower for rinsing off after a day at the beach. A setting built equally for quiet mornings and evenings. Upstairs, the primary suite delivers an ensuite bath, walk-in closet and a private balcony made for morning coffee above the palms. Two additional guest bedrooms and a full guest bath complete the second floor. Behind the finishes, the seller has invested in everything that matters: new HVAC, on-demand hot water, all-new pool equipment, new tile flooring, baseboards and lighting throughout, plus fresh interior and exterior paint. Renovated bathrooms and updated floors carry the same considered hand from room to room. A short bike ride delivers you to Key West's finest restaurants, beaches, galleries, museums and world-famous Duval Street -- yet the block itself stays wonderfully removed from it all. A neighborhood stunner not to be missed.

1427 Washington St, Key West
1800 Atlantic Blvd Unit 325C, Key West
$995,000
2 Beds ⋅ 2 Baths ⋅ 621152 MLS
Exquisite, turnkey resort living awaits in this fully furnished 2-bedroom, 2-bathroom oceanfront condominium, offering an effortless transition into Key West luxury just steps from world-famous Smathers Beach. Tucked away in a quiet oceanfront enclave, you are just minutes from Old Town, world-class dining, marinas, and the airport. Inside, high-end interior upgrades feature rich wood-grain LVP flooring through the main living areas and bedrooms, complemented by elegant large-format porcelain tile in the renovated bathrooms. The kitchen and dedicated wet bar showcase polished marble countertops, custom white shaker cabinetry, stainless steel appliances, and built-in wine storage. Light-filled open living and dining spaces flow seamlessly through hurricane impact glass sliders onto a massive 38-foot private balcony framing lush tropical greenery and partial ocean views. The primary suite boasts generous closet space, an updated vanity, and a custom walk-in shower with a frameless glass enclosure and direct balcony access. Key Property Details: Parking & Storage: Assigned covered garage parking spot plus a private locked storage locker located directly in front of your vehicle. Turnkey Ready: Sold complete with all designer furnishings, artwork, flat-screen TVs, linens, and housewares for instant occupancy. Resort Amenities: On-site sunning beach, heated oceanfront Olympic-size pool, jacuzzi, saunas, a brand-new fitness center, 3 lighted tennis courts (including 1 clay court), BBQ picnic areas, and lush botanical gardens. Effortless Ownership: HOA fees cover building insurance, exterior maintenance, water, cable/high-speed internet, and fully funded reserves ($20k assessment paid). Strong rental track record ($72k+ net annual yield).

1800 Atlantic Blvd Unit 325C, Key West
411 Louisa St, Key West
$6,750,000
5 Beds ⋅ 5 Baths ⋅ 621141 MLS
Luxurious, Modern, Historic, & Impeccably Remodeled. Welcome to 411 Louisa Street, located in the heart of Old Town Key West, less than a block from Duval Street's top dining and entertainment. This stunning five-bedroom, four-and-a-half-bath residence offers 3,663 sq. ft. of living space on an 8,227 sq. ft.oversized lot, providing rare space and privacy in one of the island's most desirable neighborhoods. Enter through the white picket fence and tropical courtyard to your grand Key West estate, where every detail has been thoughtfully designed. The first floor is set for entertaining, featuring a spacious living area and a chef's kitchen with stone countertops, an oversized island, custom cabinetry, and premium Sub-Zero, Viking, and Wolf appliances. A generous walk-in pantry adds extra storage convenience. The primary suite, also on the ground level, overlooks the pool and boasts a spa-inspired bath with dual showers, a freestanding soaking tub (with air bubble massage) and a large walk-in closet with one of two laundry areas. Outdoors, enjoy your private resort-style backyard with an oversized pool, covered lounge, and outdoor kitchen complete with gas grill, ice maker, and mini-fridge, perfect to grill up those fresh catches or hotdogs for the kids. Sonos speakers throughout set the tone to enjoy a relaxed Key West lifestyle. A floating living room staircase leads to two inviting guest rooms and a full bath. Two additional bedrooms currently serve as offices, each with en suite baths and private entrances, ideal for guest suites, studios, or remote workspaces (one includes a kitchenette). A climate-controlled standalone workshop offers a perfect space for projects, hobbies, or extra storage. Designed for both resilience and comfort, the home includes impact-rated doors and windows, a 30 KW Cummins diesel generator with 500-gallon fuel tank, smart home automation for lighting and shades, and off-street parking for two vehicles.

411 Louisa St, Key West
3228 Eagle Ave, Key West
$520,000
2 Beds ⋅ 2 Baths ⋅ 621140 MLS
Here is your opportunity to own a piece of paradise in Key West! This inviting home offers a great opportunity to start living in one of the most unique destinations in the Florida Keys. Inside, you'll find wood flooring throughout and comfortable living spaces filled with plenty of natural light. The recently remodeled kitchen is well positioned as the heart of the home and connects to the surrounding living area for everyday living and entertaining. Upstairs are two spacious bedrooms, each with large sliding glass doors that open to an inviting second-floor balcony--a great spot to enjoy your morning coffee or relax at the end of the day. Outside, the fully fenced property provides privacy and a great space for pets, entertaining, or simply spending time outdoors. Come see the possibilities and discover your own place in Key West!

3228 Eagle Ave, Key West
11 Sunset, Key West
$9,495,000
3 Beds ⋅ 3 Baths ⋅ 621128 MLS
Rare Opportunity: The Only Home For Sale on Crescent Beach, Sunset Key Welcome to 11 Sunset Key Drive -- a fully renovated retreat on the most exclusive private island in the Florida Keys, and the only property currently available on Crescent Beach. Accessible exclusively by private ferry, Sunset Key offers a rare combination of true seclusion and effortless proximity to Old Town Key West, just minutes away. Completely renovated in 2018 with over $1.7 million invested, this 3-bedroom, 2.5-bath, close to 3,000-square-foot home was rebuilt for easy island living: hurricane-impact doors and windows, an updated roof, all-new electrical and white oak engineered wood flooring, a new interior fire suppression sprinkler system, and a full exterior and interior repaint. The kitchen centers on a Sub-Zero refrigerator, new stainless appliances, new countertops and custom cabinetry, while the private pool/spa was rebuilt down to the plumbing with new handcrafted and hand painted tile, equipment, heater, LED lighting and all app-controlled. Fully furnished by Restoration Hardware and ready to move into exactly as it is. Ownership here includes access to an oceanfront restaurant, full-service spa, fitness center, tennis courts, and private beaches -- all steps from the front door. Sunset Key holds only a handful of homes, and Crescent Beach holds fewer still. Schedule your private showing today. See you soon!!!

11 Sunset, Key West
1422 Catherine St, Key West
$789,000
2 Beds ⋅ 2 Baths ⋅ 621112 MLS
Welcome to 1422 Catherine Street in The Heart of Key West. Two structures with a total of two (2) bedrooms and two (2) bathrooms. The front structure is a one (1) bedroom and one (1) bathroom and the back structure is also a one (1) bedroom and one (1) bathroom. The front structure has just recently gone through a major improvement, totally redone foundation with concrete, new floors and totally updated. Outdoors is a perfect courtyard for dining under the stars or just hanging out and solving all the world's problems. There are also washer and dryer hook ups and an outdoor shower. This home is perfect for full time residents, second home or a great rental property. Call today for your private showing!

1422 Catherine St, Key West
812 Carsten Ln, Key West
$2,599,000
3 Beds ⋅ 2 Baths ⋅ 621061 MLS
Welcome to a stunning transformation of a perfectly located Old Town home. Restored from the ground up to create a single level dream home totaling 3bd/2ba overlooking a beautiful pool and patio. Enjoy an open floor plan where the kitchen is truly the heart of the home complete with top of the line stainless Thermador appliances, quartz countertops and timeless cabinetry with a central island perfect for entertaining! Matching custom cabinetry extends into the quaint living room space offering thoughtful built in storage and a beautiful entertainment backdrop. Reclaimed Dade County pine has been lovingly restored into an accent wall rich with history and elegance. Vaulted ceilings finished in grasscloth and wood beams are found in every room of this home. Enjoy 2 spacious ensuite luxury bathrooms and a gorgeous poolside outdoor shower. Low maintenance composite decking surrounds the home and pool area that accommodates dining and lounging in or out of the pool with a sun shelf and waterfall. Lets not forget the darling covered front porch that welcomes you to this quiet lane cottage also offering off street parking. Carsten Lane is a one way driving lane stretching only one block located in the heart of Old Town known for its peaceful and private setting!

812 Carsten Ln, Key West
2809 Flagler Ave, Key West
$999,000
4 Beds ⋅ 2 Baths ⋅ 621054 MLS
2809 Flagler Ave -2,274 Square Feet of Space, Priced to Move Rarely does a home this size come up in Key West at this price point. At 2,274 square feet, this 4-bedroom, 2-bathroom residence offers significantly more room than the typical Old Town or Mid Town property -- and it's priced well below what comparable square footage commands elsewhere in the 33040 zip code. Originally built in 1953, the home received a two-story addition in 2002 that expanded both living space and functionality, giving it a layout that feels far more generous than its neighbors. Inside, 3/4-inch red oak flooring runs throughout, and every bedroom includes its own closet for real storage -- not an afterthought. A spacious office/flex room adds even more usable square footage, ideal as a home office, guest space, or additional living area. A dedicated laundry room and a large pantry/storage area off the carport round out the practical extras that are hard to find in homes half this size.

2809 Flagler Ave, Key West
193 Golf Club Dr, Key West
$1,500,000
4 Beds ⋅ 3 Baths ⋅ 620988 MLS
Located within the private Sanctuary enclave of the Key West Golf Club, this 4-bedroom, 3-bath residence offers rare privacy, coveted west-facing sunset exposure, and direct frontage along the 18th hole of the Rees Jones-designed course, all within the City of Key West. With approximately only 10 homes in the entire Key West Golf Club community offering 1,800 square feet or more of living space, opportunities at this size are exceptionally limited and rarely come to market. Inside, new tile flooring runs throughout, complementing a bright, open floor plan designed for effortless everyday living and relaxed entertaining. Expansive living and dining areas are filled with natural light and transition seamlessly to the outdoor space, where a private pool overlooks manicured fairways and wide-open skies. The setting is tailor-made for sunset gatherings, evening swims, or simply unwinding as the sun drops over the course. The well-appointed kitchen remains connected to the main living areas, creating a functional and social heart of the home. Generously sized bedrooms provide flexibility for guests, family, or a dedicated home office. Upstairs, a private balcony captures elevated golf course views and dramatic western skies, offering a peaceful retreat that feels distinctly removed from the everyday. The double-gated Sanctuary adds an extra layer of privacy and security, while residents enjoy access to two community pools and a fitness center. The golf clubhouse is just a short walk away. Nearby dining and daily conveniences allow you to enjoy the island lifestyle without always heading downtown, while Old Town Key West remains just minutes away. Approximately 15 minutes from the historic district, this property delivers a rare balance of tranquil gated living and easy access to beaches, boating, dining, and the vibrant energy that defines Key West. A sunset-facing golf course residence of this size, in this setting doesn't come around often!

193 Golf Club Dr, Key West
530 Catherine St, Key West
$3,700,000
3 Beds ⋅ 4 Baths ⋅ 620985 MLS
Awarded the Florida Keys Preservation Star, this meticulously restored single-family home offers an enchanting blend of historic Key West charm, modern luxury, and high-yield investment potential. Holding a coveted TRANSIENT LICENSE allowing profitable nightly rentals, this turnkey Old Town sanctuary sits just a half-block from world-famous Duval Street while enjoying a prime position near boutique shops, fine dining, and the Southernmost Point. Step inside through iconic yellow doors into a bright, sunny retreat defined by historic Dade County pine walls, gingerbread balustrade details, high soaring ceilings, and rich natural light. The main level flows into an open-concept living area and a sleek white kitchen equipped with stainless steel appliances, ample prep space, and an oversized island with seating for six--perfect for gathering family and friends. Designed for indoor-outdoor living, double sliders spill out to a well-appointed, covered lanai featuring a large outdoor TV and a rare air-conditioned half bath. Beyond the lanai lies a private tropical oasis enveloped by lush palm trees and fencing. Take a refreshing dip in the 8' x 14' heated pool with its soothing water feature, lounge in the sunshine on the deck, or host alfresco dinners using the gas grill. The interior layout offers total comfort and privacy for guests. The main floor houses two king-bedroom suites complete with walk-in showers, including one with direct access to the poolside sanctuary. Tucked upstairs for added seclusion, the third ensuite bedroom features a queen bed, vaulted ceilings, and sunny exposure. Completely renovated with impact windows, and dedicated off-street parking, this property is designed for effortless ownership. Whether retained as a high-performing vacation rental with proven revenue projections or enjoyed as a private island getaway, this home offers a rare chance to own a piece of Key West paradise.

530 Catherine St, Key West
30 Kingfisher Ln, Key West
$649,000
2 Beds ⋅ 2 Baths ⋅ 620917 MLS
Beautiful ''Bungalow'' style townhome in the highly sought after Key West Golf Club. Professionally landscaped yard and new paver walkway with landscape lighting and irrigation system invites you into this fully furnished 2 bedroom and 1.5 bath home with quartz countertops, stainless appliances and brand new 2026 central A/C. Relax on the screened in porch over looking the fairway of the Rees-Jones designed 18 hole Golf Course. KWGC community includes 2 heated swimming pools, fitness center, butterfly gardens and 24 hour gated security.

30 Kingfisher Ln, Key West
119 Simonton St, Key West
$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
1116 Truman Ave Unit A, Key West
$995,000
2 Beds ⋅ 2 Baths ⋅ 620885 MLS
Completely remodeled to the studs in 2024, this exceptional Key West condo is truly turn-key and move in ready. The home has been meticulously maintained and shows beautifully in every detail. Everything in the unit is new, from the finishes and fixtures to the systems. Central air conditioning and a security alarm are already in place for immediate comfort and peace of mind. This 953 sq. ft.unit features an oversized primary bedroom with a true walk-in closet, a spa inspired -large shower with a waterfall showerhead, and high-end details throughout. An additional 195 sq ft covered front porch expands the living space and is protected by premium motorized electronic screens that raise and lower at the touch of a remote-a significant high end upgrade. Located in a desirable three-unit condo association, the HOA fee covers exterior insurance and water, keeping ownership simple and predictable.. Enjoy classic Key West living with lush tropical landscaping including bamboo and a private heated pool. Super clean, super nice, and ready for immediate occupancy.

1116 Truman Ave Unit A, Key West

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