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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
Renovated 2b/2b beauty is close to the heart of Old Town Key West, yet far enough from the maddening crowd. Late-1800s Conch house with detached guest cottage were gutte...
- 2 Beds
- 2 Baths
- 620684 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
Located in the heart of downtown Key West's Historic Seaport, Conch Harbor Marina is one of the premier marina destinations in the Key West Bight. Slip 20 accommodates ve...
- 620580 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
Discover the timeless charm of Key West living at 1222 Florida Street, ideally positioned in the highly sought-after White Street Gallery District. Just a short stroll fr...
- 3 Beds
- 1 Baths
- 620399 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 500 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
An extraordinary opportunity to own one of Key West's most coveted addresses -- iconic Caroline Street in the Historic Seaport, just steps from Duval Street. Fully renova...
- 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
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...
- 3 Beds
- 2 Baths
- 620106 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
Welcome to 606 Grinnell Street located in the heart of Old Town Key West, this charming duplex offers the perfect blend of classic Key West character and flexible living ...
- 5 Beds
- 3 Baths
- 619947 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 ...
- 2 Baths
- 619902 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
- 619812 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
FLIP FLOPS INLCUDED! Some homes are just addresses. This one is a lifestyle. Tucked into the heart of Old Town Key West, this beautiful historic Conch home is wrapped in ...
- 4 Beds
- 2 Baths
- 619738 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
Welcome to 1025 Elgin Lane, an exquisite residence nestled in the heart of Key West's Historic Seaport District. This recently updated home seamlessly blends historic cha...
- 2 Beds
- 2 Baths
- 619610 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
Step into a residence that has captured the national spotlight. Recently honored as a Wall Street Journal ''House of the Week,'' 1017 Angela Street is a 118-year-old Old ...
- 3 Beds
- 4 Baths
- 619579 MLS
Historic Old Town Key West home offering character, a prime location, and strong potential for a buyer looking to add value. Originally built in 1908 and positioned on a ...
- 3 Beds
- 3 Baths
- 619554 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
Located in the heart of Old Town, 616 Eaton Street tells a story that spans more than a century. Built in 1911 and thoughtfully brought into the present day, with additio...
- 5 Beds
- 7 Baths
- 619282 MLS
DO NOT MISS YOUR CHANCE TO OWN YOUR OWN PIECE OF KEY WEST HISTORY!!!! Located in the heart of the Historic District, just steps to world famous Duval Street, 5 minutes...
- 3 Beds
- 2 Baths
- 619251 MLS
Tucked within the charm of Old Town Key West, this fully renovated historic Eyebrow home invites a lifestyle shaped by tropical surroundings, outdoor living, and close pr...
- 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
Tucked discreetly behind one of Old Town's most storied addresses, 419 Simonton Street C is a hidden gem insiders hope no one else discovers. Completed in 2026 as a brand...
- 2 Beds
- 3 Baths
- 618252 MLS
Invest in Key West with this legal Duplex which can be easily converted to a single family home! Step into a piece of Key West history with this light-filled historic hom...
- 4 Beds
- 2 Baths
- 616423 MLS
Located on the northside of Old Town only two blocks from the historic Key West Port, NYAH is walking distance from the main strip of bars and restaurants on Duval and ...
- 611315 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
Unmatched Old Town Opportunity! Location, Location, Location! This is your chance to own one of the most coveted properties in Old Town Key West—a truly unique home an...
- 3 Beds
- 1 Baths
- 615688 MLS
Extraordinary home in the historic district! Enjoy Key West living in the prized Old Town neighborhood with the perfect combination of all the top sought after attributes...
- 3 Beds
- 3 Baths
- 618823 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
Welcome to 524 Southard Street, an extraordinary luxury offering in the heart of Old Town Key West that blends upscale finishes, commercial versatility, & superior sustai...
- 3 Beds
- 3 Baths
- 617354 MLS
This is the one! Perfectly laid out two (2) bedroom and two (2) bathroom condo, with a den/office that could be an extra bedroom, in The Heart of Old Town Key West, with...
- 2 Beds
- 2 Baths
- 616479 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
Charming remodeled 1929 Old Town Key West home on iconic Margaret Street, offering privacy, new impact windows & doors, flooring and timeless island feel. Set back from t...
- 3 Beds
- 3 Baths
- 618170 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
Charming Old Town Key West home blending historic island style with comfortable modern living. This well-maintained three-bedroom, two-bath residence features beautiful h...
- 3 Beds
- 3 Baths
- 618311 MLS
Introducing The Twins on Olivia - a storied Key West treasure reborn. Once known locally as ''Olivia's Twins'' and documented on the 1892 Sanborn maps, this historic Old ...
- 3 Beds
- 4 Baths
- 616917 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
Discover unparalleled luxury in the heart of Old Town, Key West. Comprised of a main house and guest cottage, this newly built ''Smart'' property infuses casual islan...
- 6 Beds
- 7 Baths
- 617122 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
Nestled down a private and picturesque lane, this charming conch-style cottage offers the perfect blend of island charm and comfort. Featuring 3 bedrooms and 2 full baths...
- 3 Beds
- 2 Baths
- 616629 MLS
Private Old Town property with built-in income and exceptional flexibility. Ideally located near the Historic Seaport and Fausto's, this three-residence property is curre...
- 6 Beds
- 8 Baths
- 617710 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
**6%+ Cap Rate Opportunity ** Now offered at $2,490,000, this income producing Old Town property offers strong cash flow and immediate investor appeal. Located just st...
- 3 Beds
- 8 Baths
- 617030 MLS
Step into a piece of Old Town Key West history. Built in 1928, this storybook Old Town cottage captures everything to love about Key West including its timeless characte...
- 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
Invest in Key West with this Duplex which can be also easily used as a single family home! Step into a piece of Key West history with this move in ready, light-filled his...
- 4 Beds
- 2 Baths
- 616977 MLS
An UNBEATABLE LOCATION1 This light-filled, Old Town condo just one block to Duval Street! This home shines with 23 windows on two levels and relaxes with its easy, breez...
- 2 Beds
- 2 Baths
- 618827 MLS
Charming Old Town Retreat in X Flood Zone! Step into island living with this beautifully renovated 1-bedroom, 1.5-bath home, plus sleeping loft and cabana, in the heart ...
- 1 Beds
- 2 Baths
- 617909 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
Experience the ideal blend of historic charm and modern luxury in this fully renovated and expanded Key West residence, where no detail has been overlooked. Set on a quie...
- 4 Beds
- 5 Baths
- 616715 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
These properties rarely come on the market. Great opportunity to own an income producing Townhouse in the heart of Old Town Key West. This one bedroom Townhouse has a T...
- 1 Beds
- 1 Baths
- 618722 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
Rare opportunity on desirable Aronovitz Lane in the heart of Key West! This unique offering includes two properties being sold together, creating exceptional flexibility ...
- 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
