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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
Classic Key West charm and sophistication abound, with traditional grace yet modern conveniences, this wasn't just a simple remodel. This was a carefully thought out, com...
- 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 7.0% cap rate with a soli...
- 2 Baths
- 620701 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. This renovated one bed...
- 1 Beds
- 1 Baths
- 620692 MLS
The time is now to jump into The Key West Commercial investment opportunity in the Heart of Duval Street. This is perfect for you, a fully leased commercial condo to a...
- 1 Baths
- 620599 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
Old Town 'Diamond in the Rough' near Bay View Park with the highly coveted Off-Street parking. Unique opportunity to acquire a corner lot of over 4,500 sq ft in quiet Old...
- 3 Beds
- 2 Baths
- 620547 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
Limited time buyer incentive - as an added bonus, the sale now includes a low-mile 2021 Jeep Wrangler Sahara Convertible--giving you the complete Key West lifestyle with ...
- 3 Beds
- 4 Baths
- 620437 MLS
First Time on the Market in 26 Years! Just 79 steps from Duval Street, this extraordinary Historic Victorian estate presents a rare opportunity to own one of Key West's m...
- 5 Beds
- 5 Baths
- 620434 MLS
A welcoming covered front porch sets the tone for this exceptional townhome, offering the perfect place to enjoy your morning coffee or unwind with an evening cocktail wh...
- 3 Beds
- 3 Baths
- 620423 MLS
Tucked into the heart of Old Town Key West, this beautifully renovated duplex offers two distinct 1-bedroom, 1-bath residences, each finished with a refined European styl...
- 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
Welcome home! Charming Old Town Key West Cottage with Off-Street Parking. Situated on a desirable corner lot in Old Town, this 2-bedroom, 1-bath conch cottage offers t...
- 2 Beds
- 1 Baths
- 620334 MLS
Rare opportunity to Lease a turnkey Restaurant and Bar in the heart of downtown Key West. Property sits just 1/2 Block off Duval St., Greene St. and Caroline Streets at ...
- 13 Baths
- 620313 MLS
Lowest price commercial retail space in Old Town! This commercial condominium positioned along high-visibility Truman Avenue, offers an 8% CAP RATE and exceptional exposu...
- 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
TRANSIENT LICENCE RECEIVERSHIP ZONE! Welcome to your slice of paradise in Key West! This charming 2-bedroom, 2-bathroom condo located just steps from Duval Street offe...
- 2 Beds
- 2 Baths
- 620157 MLS
Where Prohibition-Era Legend Meets Modern Key West Hospitality. Historic Key West Boutique Inn on Duval Street | 7 Licensed Transient Accommodations. A rare opportunity t...
- 7 Beds
- 8 Baths
- 620044 MLS
Hidden away on one of Old Town's most storied streets, 1016 Varela St. Rear is the kind of Key West address that feels like a private discovery. Originally constructed i...
- 3 Beds
- 3 Baths
- 619952 MLS
Prime Old Town Key West Location with 55 ft of Truman Avenue Frontage and Fantastic Off Street Parking. The property currently consists of four licensed rental apart...
- 5 Beds
- 4 Baths
- 619930 MLS
FOUR UNIT Property in a Prime Old Town Key West Location with LOTS of OPTIONS! 1104 Truman Avenue is a legal four-unit property with multiple use possibilities. Gener...
- 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
Successful and profitable 20 seat seafood restaurant. One of the top 10 seafood restaurants with 4.7 star rating. Tremendous tourist and foot traffic in the immediate ar...
- 1 Baths
- 619163 MLS
Legal duplex in the heart of Old Town Key West offering flexibility for investors or owner-occupants alike. Each residence features a private entrance, in-unit laundry, e...
- 2 Beds
- 4 Baths
- 619087 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
LEGAL DUPLEX with INVESTMENT OPPORTUNITY. Located in the Old Town Key West neighborhood in the X Flood zone, this historic property presents many opportunities. Incr...
- 3 Beds
- 2 Baths
- 618878 MLS
Discover a seamless blend of historic character and modern refinement at 1209 Packer Street, a distinctive Old Town residence that quietly impresses from the moment you s...
- 4 Beds
- 4 Baths
- 618235 MLS
3 bedroom single-family home offering the opportunity to add a second bathroom within the existing roofline. Relax on the covered front porch and enjoy the Key West lifes...
- 3 Beds
- 1 Baths
- 618808 MLS
Don't miss this TRANSIENT licensed condo just steps away from the famous Duval Street. This second floor 1 bedroom 1 bath unit with 14ft high ceilings is being offered tu...
- 1 Beds
- 1 Baths
- 617074 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
A fantastic renovation of a classic Old Town Key West property, blending timeless charm with modern upgrades. First Impressions are made with a wonderful front porch gree...
- 3 Beds
- 3 Baths
- 618608 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
*** REAL POSSIBILITY FOR 2ND BATH, CALL LISTING AGENT. *** Secret Garden Cigar Maker's Cottage in Old Town 🌴 Tucked behind a private gate on a quiet section of ...
- 2 Beds
- 1 Baths
- 618516 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
This performing vacation rental sold as shown is a beautiful property which exudes a sense of warmth and character from the moment you set eyes on it. As you approach th...
- 2 Beds
- 1 Baths
- 618467 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
Old Town First floor 2 Bedroom, 2 Bath condo, pool side!. Great Old Town location, close to Restaurants, '' Walk on White' , Grocery store, and a short walk or bicycle ri...
- 2 Beds
- 2 Baths
- 618456 MLS
Tucked away in the heart of Old-Town Key West! Welcome to 1075 R10 Duval Street offers the perfect blend of privacy, island charm, and effortless living. This thoughtf...
- 2 Beds
- 3 Baths
- 618751 MLS
This property presents an outstanding investment opportunity or an ideal space for a restaurant owner. Located in the heart of Key West's bustling commercial corridor, it...
- 2 Baths
- 616037 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
Real Estate offering only, business and liquor license not included. Prime corner location with great visibility on Truman Ave. HNC -1 Zoning allows many Commercial Use...
- 2 Baths
- 617611 MLS
Buy a Bar & Liquor Store in Key West! Dons' Place is the opportunity to purchase an Iconic and Landmark Indoor and Outdoor Bar & a Liquor Store with a Drive Through! Thi...
- 2 Baths
- 614149 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
- 618409 MLS
Income producing Duplex in Old Town Key West! The Owner prefer to hold the financed note for a new owner. Fully renovated offering strong income potential and turnkey co...
- 3 Beds
- 3 Baths
- 618760 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
