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Old Town - North of Truman Homes for Sale
If you want to live just steps from the beating heart of Downtown Key West, the Old Town historical district is the place for you. Old Town encompasses the majority of the island’s tourist attractions and its central business district, in addition to epitomizing the rich historical charm of the area. Comprised of the western half of Key West, Old Town is also home to the largest collection of vintage wooden structures on the National Register of Historic Places. In fact, within this one-of-a-kind community, there are more than 3,000 wooden buildings that were constructed between 1886 and 1912. Many of these homes have horizontal wood siding painted in pastel colors, peaked metal roofs, side-hinged louvered shutters, and covered porches.
Old Town is bounded by Mallory Square, the Atlantic Ocean, and South, White, Whitehead, and Emma Streets. It is divided into Old Town North, which is bordered by The Meadows, Old Town South, and Truman Annex, and Old Town South is bordered by The Meadows, Old Town North, Casa Marina, and Midtown West. Within Old Town North you’ll find a number of the area’s most popular restaurants, among them Half Shell Raw Bar, Mangia Mangia Pasta Cafe, and BO’s Fish Wagon. In Old Town South popular destinations include Camille’s restaurant, Fausto’s Food Palace, El Siboney restaurant, and Bay View Park. Other Old Town attractions include Fort Zachary Taylor, Ernest Hemingway Home and Museum, Key West Butterfly Conservatory, Key West Aquarium, Mel Fisher Maritime Heritage Museum and Old Town Trolley Tours.
Because of its gorgeous location, rich historic charm, and spectacular amenities, the highly-walkable community of Old Town is one of the most sought-after addresses in Key West. Because early on the community recognized the aesthetic and architectural value of the Old Town neighborhood, the renovation and preservation efforts have been in full swing since the 1950s. Homes in Old Town Key West include cottages, bungalows, homes in the Classic Revival style, and Queen Anne Victorian mansions. Because of the popularity of this historic area, homes for sale here tend to be expensive but are worth every cent because of the multitude of amenities and attractions. If you would like to learn more about Old Town Key West real estate, please allow us to assist you and contact us today.
Old Town North of Truman Newest Listings
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...
- 3 Beds
- 3 Baths
- 621758 MLS
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...
- 2 Beds
- 1 Baths
- 621705 MLS
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...
- 2 Beds
- 1 Baths
- 621685 MLS
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...
- 2 Beds
- 2 Baths
- 621684 MLS
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 ...
- 1 Beds
- 2 Baths
- 621683 MLS
A rare opportunity to acquire two established and complimentary hospitality businesses operating side by side in one of Key West's most desirable and recognizable Old Tow...
- 3 Baths
- 621681 MLS
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...
- 5 Beds
- 4 Baths
- 621640 MLS
Turnkey Restaurant Opportunity - Prime Old Town Key West Location! Excellent opportunity to take over a fully equipped restaurant in the heart of Old Town Key West! Idea...
- 2 Baths
- 621634 MLS
DUAL TRANSIENT LICENSES | A RARE DEPARTURE FROM THE ORDINARY While most Old Town properties embrace tropical pastels and wooden shutters, this exceptional compound stands...
- 4 Beds
- 4 Baths
- 621632 MLS
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...
- 2 Beds
- 1 Baths
- 621609 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,...
- 4 Beds
- 4 Baths
- 621522 MLS
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...
- 3 Beds
- 4 Baths
- 621485 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 life...
- 2 Beds
- 3 Baths
- 621479 MLS
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...
- 6 Beds
- 7 Baths
- 621466 MLS
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...
- 7 Beds
- 9 Baths
- 621458 MLS
This Commercial Residential mixed use building offers an excellent investment or owner operator opportunity. A prime location 513 Truman has excellent visibility with hea...
- 2 Beds
- 6 Baths
- 621449 MLS
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...
- 3 Beds
- 2 Baths
- 621406 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 li...
- 3 Beds
- 3 Baths
- 621356 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, qui...
- 2 Beds
- 1 Baths
- 621278 MLS
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...
- 3 Beds
- 2 Baths
- 621273 MLS
Located off the 500 block of Duval Street. High traffic location on Appelrouth Lane between Duval Street and Whitehead Street. This is real estate only. Business is not f...
- 1 Baths
- 621247 MLS
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...
- 3 Beds
- 2 Baths
- 621237 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 unforgett...
- 6 Beds
- 7 Baths
- 621215 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 t...
- 2 Beds
- 3 Baths
- 621199 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 licens...
- 1 Beds
- 1 Baths
- 621189 MLS
Discover one of Old Towns true hidden gems at Andrews Inn, a turnkey six-unit B&B offering an exceptional blend of privacy, iconic island charm, and income potential. Tuc...
- 6 Beds
- 6 Baths
- 621143 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...
- 3 Beds
- 2 Baths
- 621061 MLS
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...
- 3 Beds
- 2 Baths
- 620987 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 span...
- 4 Beds
- 4 Baths
- 620913 MLS
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...
- 3 Beds
- 1 Baths
- 620880 MLS
An exceptional opportunity to own one of Old Town Key West's most recognizable mixed-use investment properties. Perfectly positioned at the prominent corner of Whitehead ...
- 3 Beds
- 5 Baths
- 620614 MLS
''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...
- 1 Beds
- 1 Baths
- 620493 MLS
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...
- 3 Beds
- 3 Baths
- 620343 MLS
701 Simonton Street offers a standout commercial presence in the heart of Old Town Key West, positioned on the highly visible corner of Simonton and Angela Streets. This ...
- 2 Baths
- 620342 MLS
Rare Duval Street lease opportunity in the heart of Old Town Key West. This approximately 635 SF street-front space offers exceptional visibility and direct frontage alon...
- 1 Baths
- 620233 MLS
Rare leasing opportunity in the heart of Old Town Key West. The property offers approximately 1,398 square feet, consisting of 1,078 square feet of ground-floor commercia...
- 1 Beds
- 2 Baths
- 620225 MLS
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...
- 4 Beds
- 5 Baths
- 620222 MLS
This large restaurant/bar in the heart of downtown Key West is presently rented for $18,000 NNN a month with over three years remaining on the lease. The location is exce...
- 2 Baths
- 620183 MLS
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...
- 3 Beds
- 2 Baths
- 620150 MLS
Ready to Build! Create your ideal home in Old Town Key West! This lot comes with a beneficial use designation and has received HARC approval for a new single-family resid...
- 620141 MLS
*** 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...
- 2 Beds
- 2 Baths
- 620130 MLS
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...
- 10 Beds
- 6 Baths
- 620102 MLS
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...
- 10 Beds
- 6 Baths
- 620101 MLS
Located within the quiet, gated security of Old Town Villas, this 3-bedroom, 3-bathroom townhome offers a sophisticated, low-maintenance island retreat just one block off...
- 3 Beds
- 3 Baths
- 619959 MLS
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...
- 7 Beds
- 5 Baths
- 619904 MLS
Hard to find small office space available in Old Town! Freshly updated professional offices 70 sf for $700+ per month. Join the friendly business environment at Key West ...
- 3 Baths
- 619902 MLS
326sf in Strip Center on Front Street across from Mallory Square, located on the busiest corner in Key West. Outstanding foot traffic from tourists, cruise ship passenge...
- 619760 MLS
Discover a rare blend of history, artistry, and luxury in this extraordinary residence at the celebrated William Fleming House--one of Old Town Key West's most iconic and...
- 2 Beds
- 3 Baths
- 619742 MLS
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...
- 7 Beds
- 5 Baths
- 619700 MLS
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...
- 3 Beds
- 2 Baths
- 619599 MLS
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...
- 4 Beds
- 4 Baths
- 619548 MLS
Old Town Professional Space available in excellent location on Truman Ave / US-1 directly across the street from the Harvey Government Complex. Four rooms comprising appr...
- 1 Baths
- 619434 MLS
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...
- 3 Beds
- 4 Baths
- 619404 MLS
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 ...
- 3 Beds
- 3 Baths
- 619306 MLS
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...
- 3 Beds
- 2 Baths
- 619235 MLS
425 Bahama Street presents an exceptional opportunity to own a revenue-generating parking lot in iconic Key West, Florida. This income-producing property offers existing ...
- 619200 MLS
Rare opportunity to acquire SEVEN units in the X-Flood Zone in Old Town Key West. That's correct, seven market rate units! Renovations in progress! Priced at less than $2...
- 7 Beds
- 6 Baths
- 615914 MLS
Rare Multi-Family Investment Opportunity in Old Town Key West. This unique property is comprised of eight updated one-bedroom, one-bathroom units. 2 buildings situated on...
- 8 Beds
- 8 Baths
- 618438 MLS
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 ...
- 3 Beds
- 3 Baths
- 618708 MLS
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...
- 7 Beds
- 6 Baths
- 615913 MLS
Introducing a prime investment opportunity at 718-720 Caroline Street, Key West, FL now offered at a 6.7% cap rate. This historic property boasts a 3,424 SF building with...
- 3 Baths
- 616452 MLS
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 ...
- 2 Beds
- 4 Baths
- 616727 MLS
Offices on Eaton Street located in downtown Key West. If you are looking for a small private office join the friendly business environment at Key West Theater catering to...
- 2 Baths
- 617942 MLS
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...
- 4 Beds
- 2 Baths
- 618211 MLS
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...
- 1 Beds
- 1 Baths
- 618122 MLS
**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...
- 4 Beds
- 6 Baths
- 617513 MLS
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...
- 3 Beds
- 4 Baths
- 616807 MLS
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 ...
- 4 Baths
- 616729 MLS
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...
- 3 Beds
- 3 Baths
- 613986 MLS
Introducing 319 Grinnell Street, a captivating residence in the heart of Key West's Historic Seaport, where charm and character abound. This beautifully framed Key West-s...
- 3 Beds
- 2 Baths
- 618819 MLS
Location, Location, Location! Old Town in X-Flood Zone on Solaris Hill with Off Street Parking! Quintessential conch cottage has a cozy front porch & has been in the same...
- 3 Beds
- 1 Baths
- 614442 MLS
TWO OLD TOWN PROPERTIES. ONE RARE OPPORTUNITY. Tucked away on desirable Aronovitz Lane in the heart of Key West, this unique offering combines an existing 2-bedroom, 1-ba...
- 2 Beds
- 1 Baths
- 618183 MLS
Prime Vacant Lot in Historic Old Town Key West - Rare Opportunity! Located in a vibrant community with rich history, this vacant lot offers endless possibilities for deve...
- 617699 MLS
Charming Single family home with multiple guest cottages in Historic Key West, Florida. Discover the allure of old historic Key West with this exceptional compound, per...
- 7 Beds
- 8 Baths
- 618468 MLS
Charming Multifamily Compound in Historic Key West, Florida. Discover the allure of old historic Key West with this exceptional multifamily compound, perfectly situated i...
- 7 Beds
- 8 Baths
- 617140 MLS
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