Key West Real Estate

Key West Real Estate

Welcome to the enchanting island of Key West, Florida, a vibrant gem nestled in Monroe County at the southernmost tip of the continental United States. Known for its stunning sunsets, rich history, and laid-back atmosphere, Key West offers a unique blend of tropical beauty and eclectic charm that captivates residents and visitors alike.

With its warm, sunny climate year-round, Key West is a paradise for outdoor enthusiasts. Dive into the crystal-clear waters of the Atlantic Ocean, explore the vibrant coral reefs, or enjoy a leisurely day on the beach soaking up the sun. The island's lush landscapes and palm-fringed streets create a picturesque backdrop for a variety of activities, from sailing and fishing to biking and walking along the scenic waterfront.

Key West is also steeped in history, with its well-preserved architecture and colorful conch houses that tell the story of its storied past. Stroll through the historic district to discover landmarks like the Ernest Hemingway Home and Museum or the iconic Southernmost Point Buoy, where you can snap a photo to commemorate your visit. The lively arts scene, bustling nightlife, and delectable dining options—from fresh seafood to Caribbean cuisine—further enhance the island's allure.

Whether you're looking to invest in a vacation home, a rental property, or a permanent residence, Key West's real estate market offers a diverse array of options to fit every lifestyle. Experience the magic of island living in Key West, where every day feels like a vacation, and the community welcomes you with open arms. Discover your piece of paradise today!

Newest Listings in Key West

1318 Duncan St Unit APT 3, Key West
$544,900
1 Beds ⋅ 1 Baths ⋅ 621579 MLS
Great opportunity to own your own home or have an excellent source of rental income. Currently the least expensive detached residence in Key West. Freshly painted interior and new AC. This renovated one bedroom condo cottage overlooking the large communal pool is just one block to vibrant White St with its cafes and restaurants, gourmet food stores, galleries and yoga studios. A short walk or bike ride to the beaches and the heart of Old Town, the Historic Seaport and Duval Street.....The compound has a large pool shared with only 3 other condos. There are lovely landscaped communal areas with fruit trees, sun decks, lounge chairs and outdoor dining areas.....Recent improvements to the home include a metal roof, impact windows plus additional storm shutters. The condo has one bedroom, a full bath with shower above, full kitchen and double doors leading to the pool and patio area.

1318 Duncan St Unit APT 3, Key West
1011 Whitehead St, Key West
$3,795,000
3 Beds ⋅ 5 Baths ⋅ 621561 MLS
Rare Old Town mixed-use opportunity at 1011 Whitehead Street, just steps from Duval Street, the Key West Lighthouse and the Hemingway Home. This historic property features three beautifully updated, furnished one-bedroom residences, each with its own kitchen and transient rental license, allowing the units to be rented individually or together. Private patios and balconies add classic Key West charm, while a street-level commercial storefront provides an additional income-producing component. With three valuable transient licenses, flexible use and an iconic walkable location, this is a unique opportunity to own a distinctive piece of Key West.

1011 Whitehead St, Key West
1311 Truman Ave, Key West
$6,449,000
7 Beds ⋅ 8 Baths ⋅ 621544 MLS
Some Key West homes are historic because they are old. 1311 Truman Avenue is historic because of who built it, who gathered within its walls, and who saved it. Its front door came from the Old Southernmost House. Past it, Dade County pine flows through every room, chandeliers light high ceilings on both floors, and the original staircase still rises where it has stood for more than a century. A second staircase toward the rear, also original to the house, recalls the scale on which it was built. Outside, sweeping double-story porches wrap the Victorian-influenced home, set on a third of an acre. The house was built at the turn of the twentieth century by Benjamin Douglas Trevor and his wife, Mary Fogarty Trevor. Mr. Trevor founded Key West's first Steam Laundry and in 1903 became Mayor of Key West. In the decades that followed, the house became home to the Key West Woman's Club and later served as a church. In 1975 two prominent local antique dealers purchased it and returned it to its original glory, and their work received the first award for an excellent restoration given by the Old Island Restoration Foundation. That restoration still defines the house. The original windows remain, along with the moldings and trim, and verandas open to the grounds from both floors. A large covered porch offers room for both dining and living, with views over the refinished pool and the guest cottage. Over the past decade, the current owners have carried that stewardship forward. A magnificent tropical garden and a stunning pool now grace the 14,490-square-foot lot. Every bathroom has been updated and finished in a fine selection of marble, granite, and quartz, and the kitchen and appliances have been updated, bringing modern comfort to a house whose history remains its defining feature. Built by a mayor, gathered in by the Woman's Club, and saved by the restoration that set the standard for Old Town, 1311 Truman Avenue is ready for the next chapter of its story.

1311 Truman Ave, Key West
809 Fleming St, Key West
$1,795,000
4 Beds ⋅ 3 Baths ⋅ 621528 MLS
This charming Legal Duplex located historical Old Town district with 2 COVERED CAR PARKING in your own backyard. 2 bed 2 bath downstairs and 2 bed 1 bath upstairs. Fantastic Front Porch and Upstairs Balcony. Just Blocks away from DUVAL street .

809 Fleming St, Key West
3728 Flagler Ave, Key West
$3,700,000
5 Beds ⋅ 5 Baths ⋅ 621515 MLS
This home has everything you need to enjoy the Key West lifestyle! With approximately 3,000 sq. ft. of living space and a 6-foot privacy fence surrounding the large property, there's plenty of room to entertain both inside and out. The kitchen features Sub-Zero and KitchenAid appliances and flows right into the main living area, making it perfect for everyday living and entertaining. The home also offers a full laundry room plus a bonus mudroom for extra storage and convenience. Outside is where this home really shines! Enjoy a covered deck area, large heated pool, and boating canal with a 30,000-lb. boat lift and ice machine. You're just minutes from the channel--no idling 1-2 miles down the canal like with many other homes. There's also covered parking and a garage with plenty of room to store all your toys. Best of all, this home is being sold turnkey and even includes a golf cart! Come see what sets this home apart from anything else on the market!

3728 Flagler Ave, Key West
5 Mccoy Cir Unit # 5, Key West
$1,350,000
2 Beds ⋅ 3 Baths ⋅ 621523 MLS
DEEDED BOAT SLIP ON ISLAND! A standout waterfront opportunity in Key West, 5 McCoy Cir #5 offers the kind of coastal living that is hard to find: a townhome with a deeded boat slip, open water views, ample parking, and direct sightlines to your slip from the balcony. From the moment you enter, the unobstructed water views set the tone, creating a bright and relaxed setting across every level of the home. Designed for easy living, this 1,387 sq. ft. townhome features a smart three-level layout with generous storage, covered parking, and multiple outdoor spaces. The main living level includes an open kitchen and living area with a convenient half bath, all positioned to take full advantage of the wide water views. Step out to the large balcony and enjoy a front-row view of your boat slip, the surrounding water, and the open horizon beyond. The top floor offers two bedrooms, each with its own ensuite bathroom, creating comfortable private spaces with a clean and functional layout. Below, the covered garage area provides ample storage for boating gear, fishing equipment, bikes, tools, and everyday essentials. Plenty of storage to store your fresh catch, stone crabs, drinks, and supplies after a day on the water. The deeded boat slip is a true highlight, offering the ability to walk directly to your boat and enjoy the water with ease. The slip can comfortably fit a 25-foot boat with dual engines, making this a special option for those who value direct water access. A private patio adds another outdoor area to relax, rinse off, or organize gear before and after time on the boat. With dedicated parking, plenty of storage options, open water views from every level, and HOA coverage that includes insurance, this property brings together convenience, function, and the Key West waterfront lifestyle in one remarkable property. Come check it out by land or by boat -- pull up to the slip and we'll give you a tour!

5 Mccoy Cir Unit # 5, Key West
1501 Truman Ave, Key West
$3,750,000
4 Beds ⋅ 4 Baths ⋅ 621522 MLS
Exceptional Key West Investment Opportunity with 3 Transient Licenses. The property consists of four private one bedrooms, one bath units, each featuring its own kitchen, living area, bedroom, and full bathroom. Most importantly, three of the four units benefit from transient rental licenses allowing nightly rentals, an increasingly rare and valuable asset in the Key West market. The fourth unit is currently rented monthly. Guests enjoy a shared private courtyard with a swimming pool, creating an inviting tropical setting and a desirable amenity for vacation renters. The property also offers three parking spaces, an added convenience in Key West. Renovated in 2018, the units blend classic Key West character with modern updates. Features include Dade County pine, engineered wood flooring, granite countertops, updated kitchen cabinetry and appliances, along with updated plumbing and electrical systems. Each unit is designed to operate independently, making the property well suited for continued use as an income producing investment.

1501 Truman Ave, Key West
1100 Johnson St, Key West
$5,200,000
4 Beds ⋅ 3 Baths ⋅ 621521 MLS
Where Casa Marina Charm Meets Modern Island Living. Set on an expansive 10,000 sq. ft corner lot in prestigious Casa Marina, one of Key West's most sought-after neighborhoods, this fully renovated 4-bedroom, 3-bath residence offers nearly 2,100 sq. ft of thoughtfully designed living space just moments from the Atlantic shoreline and the charm of Old Town. A comprehensive 2020 renovation transformed the home from top to bottom, delivering vaulted ceilings, energy-efficient LED lighting, and all-new hurricane-rated impact windows and doors that fill the interior with natural light. The open floor plan flows effortlessly between living, dining, and kitchen spaces, making it ideal for both everyday living and entertaining. At the heart of the home, the chef's kitchen features top-of-the-line Dacor appliances and custom bespoke cabinetry. The private primary suite is tucked at the rear of the home with an ensuite bath and sliding glass doors that open directly to the lanai. Each additional bedroom includes built-in closets, offering comfort and flexibility for guests or a home office. Outdoors, a custom heated in-ground pool with a soothing water feature is surrounded by elegant travertine decking and a spacious covered patio, creating a private tropical retreat for relaxing or hosting under the Key West sky. The low-maintenance front yard features artificial turf and landscape lighting that showcases the tropical foliage after dark. Peace of mind comes standard with a whole-house generator, 2-zone central A/C with linear vents, and a new standing seam metal roof that may qualify for wind insurance credits. A rare one-car garage and ample off-street parking complete this exceptional Casa Marina offering.

1100 Johnson St, Key West
6415 2nd Ter, Key West
$749,000
4 Beds ⋅ 2 Baths ⋅ 621519 MLS
Updated CBS Duplex on Oversized Stock Island Lot - Ready Now Opportunity is knocking on Stock Island! This well-maintained CBS duplex offers 4 bedrooms and 2 bathrooms on a generously sized lot, with abundant room to park and store vehicles, boats, trailers, and work equipment, a rare find this close to Key West. Both kitchens and both bathrooms have been tastefully updated, so you can move in or rent out without lifting a finger. Solid concrete block construction provides durability and peace of mind in the Keys climate. The yard is a true blank canvas, ready for your vision, whether that's a garden retreat, outdoor entertaining space, or added storage. Live in one side and rent the other, or add a strong income property to your portfolio. Available for immediate occupancy. Just minutes from Key West dining, marinas, and amenities.

6415 2nd Ter, Key West
1221 Ashby St, Key West
$1,399,000
3 Beds ⋅ 3 Baths ⋅ 621518 MLS
Situated on a spacious corner lot in desirable Midtown West, 1221 Ashby Street offers the perfect blend of comfort, privacy, and island living. The main residence features 2 bedrooms, 2 bathrooms, and inviting living spaces, while a separate 1-bedroom, 1-bathroom poolside cottage provides additional flexibility for guests or extended family. Together, the two structures offer 1,374 square feet of living space. The oversized outdoor area is designed for enjoying the Key West lifestyle, featuring a large swimming pool, spacious decking, lounge chairs, umbrellas, and an outdoor dining area ideal for entertaining. Covered off-street parking adds convenience to this property's many desirable features. Recently updated and ready for its next owner, this property offers a fantastic opportunity to enjoy island living just minutes from Key West's famous restaurants, bars, and attractions.

1221 Ashby St, Key West
1423 Rose St, Key West
$1,895,000
4 Beds ⋅ 4 Baths ⋅ 621516 MLS
Ideally located just two blocks from the beach, this beautifully renovated Key West residence blends island living, modern comfort, and plenty of space to make it your own. Set on an expansive 6,000-square-foot corner lot, the home offers more than 2,200 square feet of living space in one of Key West's most desirable residential neighborhoods. Walk to the beach and iconic White Street Pier, along with nearby pickleball courts, playgrounds, the weekly artisan market, Bayview Park, and Fausto's Food Palace. Local favorites including Salute! On The Beach and Louie's Backyard are also just minutes away. At the heart of the home is a brand-new kitchen featuring custom cabinetry, stainless steel appliances, quartz countertops, and a fresh, sophisticated finish. Thoughtful renovations throughout provide a beautifully updated foundation while leaving room for the next owners to add their own personal style. Major improvements include a new roof, impact-rated windows and doors, updated HVAC, lighting, interior and exterior paint, water heater, and other essential systems--offering peace of mind with many of the home's major components already addressed. The property also has no history of flooding, an especially valuable feature for island living. Outside, the oversized corner lot offers exceptional potential to create a private Key West retreat, with ample room for a pool, tropical landscaping, and outdoor entertaining areas. Ample street parking is available, along with off-street parking suitable for a small sedan or golf cart. With more than 2,200 square feet of living space, a substantial corner lot, extensive improvements, and an exceptional location just two blocks from the Atlantic, this Rose Street residence presents a rare opportunity to create your own piece of Key West paradise.

1423 Rose St, Key West
615 Amelia St, Key West
$1,699,000
2 Beds ⋅ 3 Baths ⋅ 621509 MLS
Enjoy Old Town Key West living just two blocks from Duval Street at 615 Amelia Street. This two-bedroom, two-and-a-half-bath single family home offers inviting indoor and outdoor spaces centered around a tropical pool courtyard. The open living and dining area features wide sliding glass doors leading to a covered deck, creating an easy flow for relaxing or entertaining. Beyond the deck, lush landscaping surrounds the pool and patio, with space for outdoor dining and lounging. The kitchen offers white cabinetry, ample storage, and a windowed breakfast nook, while a vaulted ceiling gives one of the bedrooms an airy feel. The roof and windows were upgraded in 2024. Located in Flood Zone X, annual insurance costs are approximately $6,407. From morning coffee on the deck to afternoons beside the pool, this home brings together comfortable living and a convenient Old Town location.

615 Amelia St, Key West
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