Prior to the development of Truman Annex which was a notable Naval base located in the center of Key West, now has many upscale homes and condos. This newly renovated 3-b...

Charming Home in the Meadows, Old Town, Key West. This beautiful completely renovated one bedroom cottage on Pearl Street is move in ready, and is being sold furnished. ...

Fully restored historic 3BD/3BA with 1,600 sq ft of total living space in the heart of Old Town, with pool, private guest cottage, and off-street parking, located in X fl...

Welcome to 1320 Eliza Street, a beautiful historic Key West home filled with Old World charm and character. Once serving as a local schoolhouse, this unique property sits...

Welcome to your private tropical retreat in the heart of Key West! Located on a quiet lane, just one block from Duval Street and a short walk to the Southernmost Point...

Welcome to serene lane living in the heart of Old Town. Enjoy a beautifully updated 2bd/1ba with soaring vaulted ceilings throughout. This shotgun style floor plan has b...

Steps From Duval. Worlds Away. Morning coffee on the wraparound porch. An afternoon swim beneath the waterfall. Dinner under the stars. At 813 Thomas Street, every day fe...

Quiet Old Town lane living in this historic cottage with guest house and off street parking. The main home consists of a 1bd/1ba with an additional sleeping loft and a s...

Quiet Old Town lane living in this historic cottage with guest house and off street parking. The main home consists of a 1bd/1ba with an additional sleeping loft and a s...

Turnkey Key West Investment Property with Transient Rental License! Located in the heart of Old Town, just steps from Duval Street, this charming 1-bedroom, 1.5-bathroom ...

View this property on Parade of Home Thursday 10/22 from 11am-3pm. Experience the charm of Key West living in this inviting two story residence offering three bedrooms an...

A RARE OLD TOWN FIND -- LOCATION, LIFESTYLE & INVESTMENT POTENTIAL! A MUST-SEE for the savvy investor, seasonal resident, or anyone dreaming of owning a piece of the K...

Historic Old Town Charm Meets Modern Luxury. Situated next to the iconic Key West Cemetery, this legal duplex sits proudly on the island's highest point, offering an unbe...

DUAL TRANSIENT LICENSES | A RARE DEPARTURE FROM THE ORDINARY While most Old Town properties embrace tropical pastels and wooden shutters, this exceptional compound stands...

Charming Old Town Key West Cottage with Private Pool & Rooftop Deck Welcome to 1116 Eaton Street, Key West, Florida 33040--a charming 2-bedroom, 1-bathroom single-fami...

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 interio...

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 fea...

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 fro...

View this property on the Parade of Homes Thursday 10/22 from 11am-3pm. Enjoy Old Town Key West living just two blocks from Duval Street at 615 Amelia Street. This two-be...

KEY WEST LIFESTYLE !!!!!! Prime Old Town Duplex Just Two Blocks Off Duval. (each unit also available for sale ) Exceptional investment and island living opportunity in th...

New construction, Elevated 3BD/3.5BA with heated pool and gated off-street parking on coveted Olivia Street. The Twins on Olivia is a Key West landmark reborn. The ori...

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 life...

The Autograph House is a newly built, architect-designed luxury property in the heart of Old Town Key West, ideally positioned just one block from Duval Street and the is...

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 ...

A rare opportunity in the heart of Old Town Key West's coveted Seaport neighborhood, this exceptional multi-residence property combines the charm and architectural charac...

644 William Street The property being sold is 644 William Street. The current property record/card reflects both 644 and 646 William Street, although the property bein...

Opportunity meets location in the heart of Key West's increasingly sought-after Bahama Village. Situated on a generously sized lot, 316 Virginia Street offers an exciting...

Built in 1899, 418 Amelia Street is where Key West history, privacy, and the perfect location converge. Behind classic wood siding and Bahama shutters, this two-bedroom, ...

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 li...

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...

Experience the charm and ideal location that make Old Town Key West so special. Located in the desirable X Flood Zone, this two-bedroom, two-bath home offers an inviting ...

Highly Desirable First-Floor Shipyard Condo in Truman Annex. Experience the best of Key West living in this beautifully refreshed first-floor 2-bedroom, 1-bath condo in t...

1 bedrooms and 1 bathrooms, you are going to enjoy the 626 sqft that composes this Condominium. Nested in an enjoyable neighborhood (the Meadows), and minutes from local...

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, qui...

Old Town charm in the heart of Key West! This two-story Conch-style residence offers an exceptional opportunity to enjoy island living in the highly desirable Old Town Hi...

Tucked away on a quiet lane just off Frances Street, this charming historic cottage offers the character and location that make Old Town Key West so special. This three-b...

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 unforgett...

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 t...

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 licens...

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 di...

514 Emma is a wonderful single-family home located in Truman Annex. The first floor features a large, updated chef's kitchen with double wall ovens, double refrigerator/f...

Positioned in the coveted X flood zone, this 2-bedroom, 2-bathroom townhome perfectly blends Old Town charm with modern convenience. As one of only two units in an exclus...

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 i...

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) bed...

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...

Welcome to 1105 Olivia Street, where historic Old Town character meets modern convenience in one beautifully renovated, easy-to-maintain cottage. No condo fees, no shared...

Charming Historic Old Town Key West Home, Ready for Its Next Chapter! Here's an opportunity for the buyer who sees possibility where others see a project. This 3-bedro...

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-y...

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 span...

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 beauti...

Steeped in Key West history and unlike anything else available in Old Town, 511 Tabby Lane presents an opportunity to own one of the island's most extraordinary propertie...

Turnkey Old Town Key West condo! 2 Bedrooms/2 Full Baths/ Fully Furnished/Pool-side/Rentals through March 2027! Welcome to your turnkey piece of Old Town Key West. This ...

A distinguished offering on one of Key West's most coveted private island enclaves, 32 Sunset Key Drive embodies the ease, elegance, and exclusivity of waterfront living....

PRICE IMPROVEMENT- Classic Key West charm and sophistication abound, with traditional grace yet modern conveniences, this wasn't just a simple remodel. This was a carefu...

TRANSIENT LICENSE TRANSFER RECEIVER ZONE!!!! A rare opportunity to own one of Key West's most captivating waterfront properties, where history, character, and endless po...

Experience the best of Old Town Key West in this beautifully updated 3-bedroom, 2-bath home offering the ease of single-level living. Inside, you'll find hardwood floor...

''Seaport Sanctuary'' Located within the Land's End compound steps away from the Historic Key West Seaport and Harbor Walk. This 1 bedroom 1 bath conch cottage features a...

Unbeatable Old Town Location only 3 properties to Duval Street! Live extraordinary in this Historic Victorian estate right in the middle of everything! 416 Fleming is a r...

View this property on Parade of Home Thursday 10/22 from 11am-3pm. Tucked into the heart of Old Town Key West, this beautifully renovated duplex offers two distinct 1-bed...

High Income-Producing Transient Licensed Gem in the Heart of Old Town Key West! Rare opportunity to own a highly sought-after transient licensed vacation rental in one of...

First time offered in more than 25 years, this beloved Old Town address presents a rare opportunity to own a complete compound on one of Key West's most private and premi...

Freshly relaunched and ready for its next chapter, this beautifully maintained 2-bedroom, 1-bath condo in Shipyard offers the Key West lifestyle everyone is looking for: ...

Caroline Street, steps from the Historic Seaport. This is the Key West people picture before they ever get here. Built in the late 1800s as a cigar factory, when Key W...

Discover your ideal pied-à-terre in the heart of Key West! This charming 1-bedroom, 1-bathroom apartment on Olivia Street offers a perfect blend of comfort and convenienc...

Embrace the enchantment of Old Key West Charm in this Beautifully Updated Historic Conch 3 Bedroom-2 Bath Home, featuring a Tropical Landscaped community Pool creating ul...

*** BEST PRICED 2/2 CONDO IN OLD TOWN *** Lionsgate community, heart of Old Town, one of Key West's most coveted small communities, known for its heated saltwater pool, l...

Tucked into the heart of Old Town, this beautifully restored residence pairs Key West's historic character with thoughtful modern updates--all just one block off Duval St...

Prime Multi Unit property in Old Town. Six legal apartments with 6 off street parking spaces is rarely available. There is a total of 10 bedrooms and 6 baths, divided i...

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...

LOTS OF OPTIONS! Prime Old Town Key West Location with Off Street Parking. A variety of uses; long-term rentals, monthly vacation rentals, employee housing, or mixed-u...

Tucked into one of Old Town's most peaceful and charming pockets, this unique multi-unit property offers the perfect blend of classic Key West character and flexible livi...

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...

Tucked into one of Old Town's most peaceful and charming pockets, this unique multi-unit property offers the perfect blend of classic Key West character and flexible livi...

Tucked away on a quiet private lane, this charming classic Key West cottage offers the perfect blend of historic character and modern comfort. Thoughtfully renovated, the...

Welcome to 214 Eanes Lane, a classic Key West property offering flexibility, character, and exceptional investment potential in a prime Old Town location. Located in an X...

Discreetly tucked within the storybook streets of the coveted Meadows, this enchanting Key West residence is a rare expression of timeless elegance and island sophisticat...

On a quiet lane in Old Town, this classic Conch home offers a setting where life feels just a little slower and a lot more enjoyable. From the moment you step inside, the...

Tucked away in the Historic Seaport District, this unique three-bedroom, two-and-a-half-bath condo offers privacy, charm, and flexibility in an exceptional location. Set ...

Tucked within the charm of Old Town Key West, this historic Eyebrow home invites a lifestyle shaped by tropical surroundings, outdoor living, and close proximity to the i...

President's Walk townhome in the Truman Annex. This is a two-bedroom, 2.5-bathroom unit that also includes a deeded carport. It is a great location close to the communit...

This two-bedroom, two-bathroom condominium residence at Santa Maria Suites Resort offers both personal use and strong rental income potential. One of the resort's limited...

Beautifully updated and styled with plush new interior designed furnishings, 401 Emma Street Unit H is a vacation rental townhome that has BOTH Ocean and Harbor views in ...

A little Key West retreat with a lot to love. Tucked away in the highly desirable Meadows neighborhood of Old Town, this charming ground-level one-bedroom, one-bath condo...

Located in one of Key West's newer developments at The Captains House in Bahama Village, this second floor, single level condo blends crisp renovation with classic island...

1014 Truman Avenue - Modern Island Elegance in the Heart of Key West Welcome to a Key West retreat where modern design meets the island's laid-back charm. This immaculate...

Location, Location, Location! A renovation project that will increase the value of your investment exponentially! This home is located between the Southernmost Point and...

Nestled in an X flood zone in Old Town , this lovely conch cottage has been well cared for, meticulously maintained and lightly used as a seasonal getaway. The two-bed...

Unique and extraordinary triple (3) lot property located in Old Town, Key West! Currently featuring a two-story home with 2 bedrooms and 2 bathrooms, and an in-ground poo...

103 Front Street is a one of a kind masterpiece of architectural design and modern aesthetic. Built in the early 1900s, this imposing structure has been thouroughly resto...

Unique opportunity to renovate this historic Old Town eyebrow home on a quiet, one-way, block of Elizabeth Street. Situated on a 3038 Sq.ft. lot there is ample space for ...

Excellent opportunity whether looking for a private residence or an investment. This home will not disappoint. Artfully renovated very spacious three story . Plenty of...

Timeless Old Town Charm! Discover the timeless appeal of this beautifully remodeled historic home located in the heart of Old Town, Key West. Offered fully furnished, th...

Rare opportunity to acquire SEVEN units in the X-Flood Zone in Old Town Key West. That's correct, seven market rate units! That's less than $272K per unit! Renovations in...

Heart of Old Town Key West. Very rare FULLY RENTED income producing mixed-use property. 2/2 residential, office plus a detached restaurant. Seller financing is available ...

This rare Key West treasure hasn't changed hands in over a century, and it sits on the most coveted block in Old Town. A true time capsule waiting to be revived, it's the...

One Bedroom / One bathroom PLUS super cool Sleeping Loft! THIS is it! Step into a piece of Old Town Key West history. Built in 1928, this storybook Old Town cottage capt...

**31 photos have been virtually staged and enhanced to assist buyers in visualizing design and decor options for this home.** Casa Sapodilla introduces itself with the k...

This show-stopping luxury condo delivers a rare blend of historic charm with a fully renovated interior that was just completed a few years ago. The first level features ...

Built in 2008, this stunning 3-bedroom, 3.5-bath pool home perfectly blends the timeless character of classic Key West architecture with the comfort and convenience of mo...

Traditional key West home impeccably maintained, boasts three bedrooms, three full baths with plenty of closets throughout the home. Large private lot with a heated poo...