Key West Condos for Sale - Condominiums, Florida Keys Real Estate

Located in the prestigious Truman Annex community, this town home in The Foundry is the perfect getaway offering the perfect blend of luxury, comfort, and convenience. This beautifully designed 2-bedroom, 2.5-bathroom home enjoys a highly desirable location with easy access to Key Wests vibrant Old Town, while maintaining privacy and security within a gated community.As you step inside the spacious open-concept living area you will find 11 foot high ceilings, impact rated windows and glass doors that bathe the interior with natural light, and updated finishes throughout. The kitchen has been recently updated with all stainless steel appliances. Moving up stairs, the master bedroom is a private sanctuary featuring an ensuite bathroom. A private balcony off the master suite offers a peaceful retreat to enjoy the island breeze. The guest bedroom is up one more floor and is equally inviting with its own ensuite bathroom ensuring privacy and comfort for visitors. Stand out features of this town home include its street facing orientation, not something all homes in The Foundry have. The town home also has its own carport with additional storage above- a highly convenient feature few have and holds a value in excess of $75,000. Finally, The Foundry has its own pool, reserved for use by only Foundry owners and their guests.With a strong rental history and a Truman Annex Special Transient License, this home is an excellent investment opportunity. The license allows for short-term rentals with restrictions, providing flexibility and a steady stream of income when the property is not in use.Whether youre seeking a full-time residence, a seasonal escape, or a profitable rental investment, this townhome provides the ultimate opportunity to experience the best of Key West living.

For the first time, the Key West home of famed landscape architect and Martha Stewart co-star Fernando Wong is available. Welcome to your dream townhouse nestled in the heart of the exclusive Truman Annex, just steps away from the restaurants, shops and bars on Duval Street. This professionally decorated 2-bedroom, 2.5-bathroom townhouse offers the perfect blend of modern comfort and island charm. As you step inside, youll be greeted by a light-filled open floor plan, featuring a charming living and dining area with tasteful furnishings and a well-appointed kitchen with new appliances. The home features furniture and lighting from Brown Jordan, Ralph Lauren, and Serna & Lilly. Recent renovations include all-new ceiling lights and stylish Legrande light switches and outlets. You will also love the new wood doors, renovated bathrooms, and a recently installed lush jungle landscape. The three beautiful outdoor areas and a strong rental history make this delightful vacation house a once-in-a-lifetime opportunity.

Old Town Key West elevated two-story duplex on a quiet lane just a half block from the X Flood zone. This duplex already has Condo documents in place but is being sold together. Each unit features 2 bedrooms, 1 bathroom, and inviting living spaces with lots of light and high ceilings, ideal for comfortable island living. Enjoy the convenience of living only 3 blocks to Duval St but having the tranquility of lane living. The downstairs unit has a breezy front porch perfect for morning coffee, and a spacious back deck, ready for outdoor entertaining. Whether youre seeking investment income, a multi-generational home, or live in one and rent the other, this property delivers.

This beautifully updated 3 story Foundry townhome in the exclusive gated Truman Annex community is a dream come true! The floor to ceiling windows and doors at the entry allow sunshine to filter into the main floor living space creating a bright and airy space. The main floor has 11 foot ceilings and double French doors that open to the private front courtyard and porch. The main living space has an open floor plan and the kitchen features stainless steel appliances. The microwave and dishwasher were installed new in 2024. The half bath is located on the first floor for convenience. Make your way up the stairs to the primary suite, located on the second floor with an en suite bath and walk in shower, along with a private balcony. The washer and dryer are located on this floor and were installed new in 2024. The floor to ceiling French doors and windows allows light to encompass the space. The guest suite is located on the third floor with an en suite bath and shower tub combo. The wall to wall windows allow natural light to flood the room. This home has a designated off street parking spot for 1 vehicle located just out front of the private courtyard. The Foundry swimming pool is a short walk. This townhome is just down the block from Trumans Little White House, and is an easy walk or bicycle ride to Ft. Zachary Taylor Park, The Coffee Butler Amphitheater and the Truman Waterfront, as well as the world famous Mallory Square and Duval St. The sale comes with a special use Truman Annex transient license with restrictions. This home is currently an active luxury vacation rental with rentals on the books into 2025 making an easy transition for buyers wanting use this as an investment property.

Beautiful, comfortable, spacious condominium in historic Delancey Hall. Located on a premier Old Town street a few short blocks from the Key West Seaport and Duval Street (and in the X-flood zone), this condo offers the historic features youd expect from a pedigreed Key West house -- Dade County Pine, crown molding, shutters, wide front porch -- combined with the modern features you need, seamlessly integrated to give you the quintessential Key West experience. Whip up a tasty breakfast in the light-filled kitchen and enjoy it on your large private deck leading to your outdoor shower and the shared pool, or take an easy stroll to Harpoon Harrys or Sarabeths for a little morning pampering. With ample storage and even the option for a one-bedroom lockout, this home serves as the perfect retreat or vacation rental investment property. Its Key West living at its best -- make it yours! (Photos coming soon!)

This stunning 5 bedroom condo boasts panoramic ocean views that will take your breath away. Expansive floor plan that was originally two separate condos are now harmoniously combined into one luxurious corner unit. The south facing position offers the perfect vantage point to soak up the Atlantic Oceans beauty and Smathers Beachs glistening white sands. The living room and dining room take full advantage of the encompassing view. Open the sliding glass door to capture the sea breeze, or step out on one of your two balconies to relax and soak up the sun. A well-equipped galley-style kitchen is a chefs dream, complete with a breakfast bar, granite countertop with mosaic tile backsplash, soft close cherrywood cabinets combined with ample storage, and stainless steel appliances. Five bedrooms are beautifully appointed, four capture ocean views and all have comfortable pergo flooring with lots of natural light. Two well-designed, streamlined bathrooms with glass enclosures for the tub and shower lend a touch of luxury. Take advantage of two separate entrances, one that steps into the main living area and the second that leads invitingly through the bedroom wing. Five separate mini split AC units, a tankless hot water system, 2 heat pumps, 200-amp electrical service all contribute to the homes functionality and convenience. Ensuring both style and security are plantation shutters on the interior and crank-style storm shutters for all windows on the exterior. Recessed LED ceiling lights, crown molding, 7-inch baseboard molding, and tray ceilings throughout add an elegant touch. Key West by the Sea is nestled on nine acres of beautifully manicured property that is gated secure and is an effortless stroll to the beach and mere minutes away from the world-famous Duval Street. Residents can access a sparkling lap pool, a heated pool, two tennis courts, and bocci ball courts for year-round enjoyment.

Situated along the beautiful Key West coastline with exquisite oceanfront views, The Key West Beach Club epitomizes elegant living. Claiming sweeping views of the Atlantic Ocean, these residential condominiums are a peaceful and private enclave designed to exist in perfect harmony with their beautiful natural setting. Beach Club #213 is a freshly painted 2 bedroom, 2 bathroom residence featuring 1,531 square feet of indoor living space and a private beach front balcony offering 300 square feet of covered outdoor living space. Highlights include an open floor plan, stainless appliances, and the opportunity to enjoy an easy island lifestyle in one of Key Wests most coveted communities. The Primary bedroom features ocean views, glass sliders that open to the private balcony and outdoor seating area, a walk-in closet, and an en suite with Jacuzzi tub. Unmatched amenities include 2 oceanfront swimming pools, tennis courts, gated entry, covered parking and a storage unit. The Key West nature preserve, White Street Pier, and the islands best beaches, restaurants, and shopping are all within walking or biking distance. Very easy to show!

Escape to Paradise in this Turnkey Truman Annex Villa! Nestled within the exclusive gates of Porter Court at Truman Annex, this exquisite 2-bedroom, 2.5-bathroom villa at 406 Porter Lane offers the quintessential Key West lifestyle. Immerse yourself in tropical elegance with palm tree and bird motifs adorning the furnishings. The spacious interior living area flows seamlessly through French doors onto a sprawling private deck, perfect for al fresco dining and relaxation. A bay window frames the inviting indoor dining area, while the gourmet kitchen boasts top-of-the-line appliances to satisfy any chef. A convenient powder room completes the first floor. Upstairs, the primary suite features a generous closet and an en-suite bathroom with a tub/shower combination. The second bedroom offers ample storage with double closets and easy access to a full hall bathroom. Beyond your private oasis, enjoy resort-style living with access to a sparkling community pool, a soothing Jacuzzi spa, and ample lounging space. For beach lovers, the pristine sands of Fort Zachary Taylor Park are just steps away. Offered fully furnished, this turnkey villa is ready for you to start living your island dream!

Great opportunity to own a single level luxury two bedroom/two bath condo at the exclusive Santa Maria Resort in Old Town Key West. Just steps from Key Wests vibrant downtown scene, this Santa Maria condo also has beach access PLUS a transient rental license with tons of income producing possibilities. This is resort living at its best with beautiful pool and grounds, off street parking and restaurant on site. Make plans to see it today.

Escape to your own tropical haven at 1209 Grinnell Street. Nestled in an exclusive, gated community this updated and meticulously maintained rare end unit townhouse is set in the coveted X-flood zone and boasts impact windows and doors, turn-key furnishings, and access to a newly resurfaced and tiled serene heated community pool. Recently enhanced with fresh paint inside and out, lush new landscaping, and a state-of-the-art irrigation system, this home offers a low-maintenance slice of paradise. One of only seven homes in the highly desirable Grinnell Gardens, 1219 Grinnell features 2 bedrooms, 2.5 bathrooms, and a spacious, light-filled open layout. The cozy front porch of this home is the ideal spot for morning coffee, capturing the breezy island vibe while overlooking the pool and gardens. The main floor offers an inviting living space with Saltillo tile and recessed lighting, along with a half bath, dining area, and a sleek kitchen equipped with stainless steel appliances, Corian counters, and custom wood cabinetry. Adjacent is a dining area with lovely views of swaying palm trees, leading to your private fenced courtyard with direct access to your own assigned parking spot. The gated courtyard is perfect for sunset dining al fresco and entertaining all of your guests, complete with new decking and patio furniture. Upstairs, two spacious bedrooms await, complete with tiled floors and a convenient laundry closet. The primary ensuite bedroom features vaulted ceilings, a bath with a tub/shower combo, a spacious closet, and a large private porch for quiet relaxation. An additional loft provides extra storage or a cozy sleeping nook for guests. The second bedroom is bright and airy, paired with a hall bath that offers a tiled walk-in shower. Dont miss this chance to own a fully furnished, move-in ready island retreat that blends charm, privacy, convenience, and modern amenities in one of Key Wests most sought-after locations!

Second Floor Harbour Place Condo located in the historic Navy Administrative Building. Features high ceilings and tile floors throughout. One level living with 2 bedrooms and 2.5 Baths. Large primary bedroom ensuite with walk-in closet. The guest bedroom has French doors that open to the balcony with guest bathroom in the hall. Includes the special Truman Annex transient rental license.

Perfectly situated in the heart of Casa Marina! This 3-story townhome is being sold FULLY FURNISHED! Ideal for year round living or ready-to-go as a vacation rental!Recently renovated, open floor plan features a designer kitchen with custom Hansen & Bringle cabinets, quartz countertop, farm sink, Viking stove, refrigerator, dishwasher and custom-cut Carlisle Lumber pine floors. Two en suite bedrooms on the second floor along with washer & dryer. Professionally landscaped and lighted backyard with dip pool. New air conditioner unit in 2017. 3rd bedroom / bath on 3rd floor, with room for an office. This Townhome offers 1 dedicated parking space with lots of additional parking on street in quiet neighborhood but steps away from downtown Key West. Front and back porches on 1st and 2nd floor. Call listing for a showing!

Condo living with hotel caliber amenities, this first floor Beachside Condominium unit has it all. 2BD/2.5BA, w/ lockout & 2 transient licenses for optimal rental potential. Owners can live in this magnificent condo year round or part of the year & rent it when not in town. Beautifully appointed w/ gourmet kitchen, marble floors, fully furnished & stylishly decorated. All doors & windows are designed to exceed building codes & rated for 175 mph winds. On-site resort amenities include private beach, heated waterfront pool, spa, poolside bar/grill, valet parking, concierge, on-site management company, gourmet restaurant & the islands largest conference center.

Condo living with hotel caliber amenities, this 3rd floor Beachside Condominium unit has it all. 2BD/2.5BA, w/ lockout & 2 transient licenses for optimal rental potential. Owners can live in this magnificent condo year round or part of the year & rent it when not in town. Beautifully appointed w/gourmet kitchen, marble floors, fully furnished & stylishly decorated. All doors/windows are designed to exceed building codes & rated for 175 mph winds. On-site resort amenities include private beach, heated waterfront pool, spa, poolside bar/grill, valet parking, concierge, on-site management company, gourmet restaurant & the islands largest conference center.

Excellent opportunity whether looking for a private residence or an investment. This condo will not disappoint. Artfully renovated very spacious three story . Plenty of outside area including private courtyard with a heated pool. Walk out the front door and just steps away from Duval st. and everything Key West has to offer. This is maintenance free living while it gives the feeling of a private residence. Assigned off street parking right in front of the unit. This property is being offered turnkey. Vacation Rental history available .This home has all hurricane impact windows and doors. making the unit noiseless.

This second-floor luxury condo is ideally situated just one block from the beach and the iconic Southernmost Point, offering the perfect balance of vacation living and income potential. As a high-demand rental property with an impressive occupancy rate, it presents an excellent opportunity for a 1031 exchange, especially with on-site management ensuring seamless service for guests.The propertys amenities elevate the experience--guests can unwind at the poolside open bar, where beer, wine, and soft drinks are served to enhance their stay. With prime proximity to renowned fine dining, vibrant Duval Street, and the beach just steps away, this condo is positioned to attract affluent vacationers looking for a premium experience.Whether youre seeking a luxurious getaway for yourself or an income-generating investment, this exceptional condo promises both lifestyle and return on investment.

Welcome to Key West Beach Club. This top floor condo includes 2 bedrooms, 3 baths, large living/dining room and gorgeous views of the Atlantic Ocean. Upstairs is an enormous possible 3rd bedroom/loft and private bath. The Beach Club offers exclusive access to two beachfront pools, a fitness center, tennis court and a secure covered parking garage. Call today for a private showing!

Development Opportunity. (4) townhouse unit complex situated on a heavily landscaped 10,000 sq ft parcel. Comprised of (2) side by side duplexes legally subdivided as ( 4 ) individual, 750 sq ft licensed units, with (4) separate legal descriptions, parcel numbers, insurance policies, & utilities meters. At one time, there were four individual loans on each of the units as well.**** The only common area is the roof over each duplex, the shared wall between the units and walkways between, and on either side of each of the (2) duplexes. **** Each unit has its own laundry room addition directly off the kitchens with separate exterior screen doors - - (4) pairs of new washers & dryers. Current below market rents for each 2 bedroom, 1 bathroom unit runs between $2,225 to $2,900 with the lower rents soon to be increased.***** Always operated as a successful rental property, the units were never sold off, which is definitely the Highest and Best use of the complex. Added value would be to install a lap pool/ patio area in the 100 wide back yard as a common use amenity. 2nd option - would be to provide a private pool area for each of the rear (2) units, giving each one half of the large rear yard, greatly increasing their sale value. Mature landscaping that has been well maintained surrounds the property and separates the units. Other valuable amenities are the over sized covered front porches with high open beamed ceilings offering additional square footage - and - valuable on site parking for 10 cars. The property has been continually well maintained - painted, new air conditioners & water heaters replaced when needed and blinds & curtain rods on all windows. All roof screws were replaced & new ones added to code standards. ***** Under Documents Tab, see the survey with legal descriptions for each unit, floor & site plan & aerial photo. (4) Windstorm, Flood, Fire & Liability policies in place. Call for additional information. Realtor owned.

This 2 bedroom, 2.5 bath Harbour Place condo is located on the first floor (2nd floor as parking is on ground level) The first-floor units have the largest decks with plenty of room for entertaining, relaxing and watching the sunsets and boats coming in out of the Key West harbor. The elevator is conveniently located, and the community pool is steps away. Covered parking. Conveniently located in Truman Annex, close to Mallory Square, Fort Zachery Taylor beach, and famous Duval Street. Includes the special Truman Annex transient rental license.

Luxury Waterfront Condo with Transient License - Key West, FL. More pictures and videos coming soon.This stunning 5-bedroom, 4-bathroom waterfront condo in Old Town Key West offers luxury and investment potential with a coveted transient nightly rental license. Enjoy breathtaking marina views from double balconies, a private pool, and a boat dock with deep water access. The home features an island kitchen, a two-car garage, and is built to Cat 5 standards with impact windows. Perfect as a personal retreat or income producing nightly rental. Dont miss this rare opportunity!