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Old Town - South 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.
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Old Town South of Truman Newest Listings
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...
- 4 Beds
- 4 Baths
- 621742 MLS
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...
- 3 Beds
- 3 Baths
- 621735 MLS
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...
- 3 Beds
- 4 Baths
- 621679 MLS
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...
- 2 Beds
- 2 Baths
- 621668 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 interio...
- 1 Beds
- 1 Baths
- 621579 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 fea...
- 3 Beds
- 5 Baths
- 621561 MLS
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...
- 2 Beds
- 3 Baths
- 621509 MLS
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...
- 4 Beds
- 4 Baths
- 621502 MLS
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, ...
- 2 Beds
- 2 Baths
- 621361 MLS
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 ...
- 2 Beds
- 2 Baths
- 621345 MLS
Situated in Duval Square along Key West's Duval Street, this approximately 1,592 SqFt commercial property consists of two combined condominium units currently configured ...
- 3 Baths
- 621255 MLS
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...
- 5 Beds
- 5 Baths
- 621141 MLS
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...
- 2 Beds
- 2 Baths
- 621130 MLS
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...
- 2 Beds
- 2 Baths
- 621112 MLS
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...
- 3 Beds
- 4 Baths
- 620985 MLS
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...
- 2 Beds
- 2 Baths
- 620885 MLS
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 ...
- 2 Beds
- 2 Baths
- 620829 MLS
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...
- 3 Beds
- 3 Baths
- 620747 MLS
Rare chance to own a piece of the most iconic street in the Florida Keys. This turn-key commercial building at 1215 Duval Street is offered at a 7.04% cap rate with a sol...
- 3 Baths
- 620701 MLS
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...
- 3 Beds
- 2 Baths
- 620577 MLS
PRIME INVESTMENT OPPORTUNITY! 3 Commercial Condos on White Street in X Flood Zone. Newly formed condo building on busy Old Town Street in HNC-1 zoning - uses include prof...
- 3 Baths
- 620495 MLS
PRIME COMMERCIAL SPACE - Two combined commercial condos on White Street in X Flood Zone! These 2,061sf 1st floor units have been extensively updated and renovated with hu...
- 1 Baths
- 620494 MLS
PRIME OPPORTUNITY FOR OWNER/OPERATOR! Commercial condo available with over 1,300 sq. ft. centrally located in Old Town. This is an end unit and has a half bath, hurricane...
- 1 Baths
- 620484 MLS
Prime commercial space available with 892sf centrally located in Old Town. Unit has hurricane rated windows and doors, features one assigned parking spot and is located i...
- 1 Baths
- 620483 MLS
Newly formed commercial condo now available for sale on White Street in X Flood Zone! This 1,169sf 1st floor corner unit has been extensively updated and renovated with h...
- 1 Baths
- 620482 MLS
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...
- 5 Beds
- 5 Baths
- 620434 MLS
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...
- 2 Beds
- 2 Baths
- 620360 MLS
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...
- 2 Beds
- 2 Baths
- 620355 MLS
Lowest-Priced Commercial Retail Space in Old Town -- Offering an 8% CAP Rate. Positioned along high-visibility Truman Avenue, this commercial condominium delivers excepti...
- 1 Baths
- 620196 MLS
Prime retail leasing opportunity in the heart of Old Town Key West, just one block from Duval Street. This 805 SF storefront on Simonton Street benefits from exceptional ...
- 1 Baths
- 620194 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 Old Town Key West Location with Off Street Parking and 55 ft of Truman Avenue Frontage. The property currently consists of four licensed rental apartments; one ...
- 5 Beds
- 4 Baths
- 619930 MLS
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...
- 5 Beds
- 4 Baths
- 619927 MLS
1202 Simonton Street sits in the heart of Old Town, South of Truman, four blocks from the Southernmost Point. This corner has been home to some of Key West's most recogn...
- 619755 MLS
Turnkey boat charter and Airbnb business in Key West featuring a 42' Maxum cabin cruiser set up for short-term rental use, plus a 17' Angler (2023 Suzuki 140HP) and 22' H...
- 2 Baths
- 619435 MLS
The Blue Cat & Red Dog Too! For over 30 years the Blue Cat has served the Key West fur community. Boasting loyal customers worldwide, the Blue Cat features must have Key ...
- 1 Baths
- 619166 MLS
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...
- 2 Beds
- 2 Baths
- 619022 MLS
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...
- 2 Beds
- 2 Baths
- 618271 MLS
Location, Location, Location! A renovation project that will increase the value of your investment exponentially! This home is located between the Southernmost Point and...
- 2 Beds
- 1 Baths
- 611075 MLS
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...
- 2 Beds
- 1 Baths
- 618592 MLS
Boutique commercial, ground floor office condo for sale in Old Town at Seafoam Condominiums. Only one of two Commercial units in the building. This 665 sf. office is turn...
- 1 Beds
- 1 Baths
- 614786 MLS
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...
- 3 Beds
- 3 Baths
- 616089 MLS
Excellent opportunity whether looking for a private residence or an investment. This home will not disappoint. Artfully renovated very spacious three story . Plenty of...
- 3 Beds
- 3 Baths
- 610882 MLS
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...
- 3 Beds
- 3 Baths
- 618863 MLS
A rare opportunity to purchase one a transferable City of Key West Vendor's License. These licenses are limited in availability and allow the holder to engage in vendor o...
- 617315 MLS
Located at 521 United Street, the Southernmost Inn was originally built in the 1800s as a Francisco Marrero cigar factory. With much of the old cigar factory features res...
- 611311 MLS
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