$1,640,456Average Value$1,312Average Price per Sq Ft101Homes For Sale
History and contemporary culture collide in Old Town
Old Town is at the heart of Key West in more ways than one. This centrally located historic district serves as the city’s main shopping, dining and entertainment hub, home to boutiques, local businesses and a bubbly nightlife scene on Duval Street. Roosters and chickens, thought to be brought over from Cuba in the 1800s, roam the streets like squirrels in suburbia, catching the attention of tourists. For locals, though, they’re just part of the island’s charm and have become somewhat of an unofficial city mascot.
As the southernmost island in the U.S., Key West is beloved by many for its clear, turquoise waters reminiscent of the Caribbean Sea. “The ocean is a big draw, and it always has been. A lot of people who buy homes here enjoy the water in one way or another. They’ll have a boat or go out on the charters,” says Key West resident Lisa Lennon, a Realtor with Berkshire Hathaway HomeServices Knight & Gardner Realty. Charter boats take off from the historic seaport area, which is also home to the city's aquarium and maritime museums. Boat owners can dock at nearby Garrison Bight Marina or join the Key West Yacht Club.
Old Town tells the city’s story through historic sites like the 1848 Key West Lighthouse and the 1852 Basilica of St. Mary Star of the Sea, one of South Florida’s oldest Catholic parishes. Visitors come from all over the world to stay at one of Old Town’s many vacation rental properties, and residents may find themselves navigating around large groups of tourists during the island’s high season, December through April. But for those who call Key West home, whether for six months or the whole year, sharing the island lifestyle with visitors isn’t a burden. “There's a saying here that you might have seen on bumper stickers,” says Key West resident Mike Caron, a Realtor with Keller Williams Key West Compass Realty. “It’s called ‘One human family.’ And that’s basically what Key West is.”
Many small package and liquor stores can be found around Old Town.
The Key West Shell Warehouse is a great place in Old Town to grab some souvenirs.
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Bahama Village is known for its conch-style homes
Among Old Town’s historic homes is the Oldest House Museum, a traditional white Bahamian-style home built in 1829 that presents a perfectly preserved pocket of the island’s early years. Known locally as conch style, this architecture is typical across Old Town and stands out for its cozy front porches, wooden shutters and intricate trim. Nowhere is this style more prevalent than in the historic community of Bahama Village, a small pocket within Old Town where rows of conch homes have survived since the 1800s. “It’s now become the face of Key West,” Lennon says. Like many homes in the neighborhood, these properties sit on slightly raised platforms, which increase air circulation underneath to limit mold and water damage. Old Town is in the X-flood zone, meaning that its higher elevation makes it slightly less flood-prone than lower areas like Midtown. However, flood insurance and hurricane preparedness features like impact-resistant windows are highly recommended.
Homeowners in this historic district must maintain the home’s original exterior whenever possible. The Historic Architectural Review Commission reviews all renovation proposals. Interiors, however, are often fully updated with open floor plans and modern kitchens. Single-family homes priced under a million usually need significant repairs. Older renovated properties cost between $1 million and $2 million, while renovated three- and four-bedroom homes typically range from $2.5 million to $5 million. Select historic properties and larger homes licensed for transient rentals can top out around $8 million. To combat rising rent prices, the city is developing dedicated workforce housing units in Old Town, which Donnelly says are “so desperately needed here because the apartment situation for workers is so expensive.”
Old Town Key West offers sections with smaller homes many with wrap around porches.
The historic district of Key West is known as Old Town with many museums and historic landmarks.
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Snorkeling and swimming at Fort Zach Beach
Fort Zachary Taylor Historic State Park, home to one of the country’s largest pre-Civil War weapons collections, covers 54 acres at the island's tip. A rock jetty curls out into the ocean, protecting the famous white sand beach from the strongest cruise boat currents and offering ample room for snorkelers and scuba divers to explore the clear water. Picnic tables lie in the shade of towering Australian pine trees, offering a welcome respite from the sun. “The city tried to remove all the pines about 10 years ago because they’re not indigenous to the area. The community raised $100,000 and got an attorney to save the pines. Can you imagine this without any shade?” says Brenda Donnelly, broker and owner of Brenda Donnelly Real Estate and a 40-year resident of Key West. The state park requires a small admission fee, but many residents get annual passes.
The interactive Florida Keys Eco-Discovery Center marks the beginning of Truman Waterfront Park, a renovated 33-acre green space with a popular shaded playground and splash pad surrounded by landscaped lawns. The park hosts a weekly farmers market on Thursday afternoon and is a popular spot to watch the sunset away from the bustle of Mallory Square, which is known for its nightly sunset celebrations. In addition to a few pocket parks and playgrounds, residents can use the basketball court at Frederick Douglass Gym and the outdoor pool and playground at Martin Luther King Jr. Community Center.
The Key West Lighthouse stands tall in Old Town and serves as a museum today.
The Beach at ack Taylor Historic State Park is a great place to cool off.
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Dining in Hemingway’s footsteps at Blue Heaven
Most restaurants sit north of Truman Avenue, creating a walkable culinary web. There are plenty of spots to grab fried conch fritters or stone crab when it's in season, and more than a dozen bakeries and eateries claiming to serve the best Key lime pie or Cuban coffee. Old Town Tavern & Beer Garden offers a diverse menu of international dishes, from traditional shepherd’s pie to homemade banh mi sandwiches. The iconic Blue Heaven pairs eye-catching art and rustic outdoor seating with gourmet ingredients and one of the tallest toasted meringue toppings available on a Key lime pie in the city. Before it was a restaurant, the property hosted boxing matches refereed by Ernest Hemingway himself. Now, diners enjoy live music and happy hour in a tropical setting complete with island wildlife. “Talk about chickens,” Caron says. “They run right through while you’re eating.” Other local recommendations include Santiago’s Bodega, an upscale tapas spot with homemade sangria, and Moondog Café, a colorful, mural-filled bakery across the street from the historic Hemingway Home and Museum.
When the sun sets, Duval Street comes to life with a diverse sampling of music carried on the breeze between bars. Jazz clubs offer weekly swing dancing lessons; rounds of beer fly at Sloppy Joe’s Bar, one of Hemingway’s hangouts; connoisseurs sip from their glasses at wine bars like Vinos on Duval. When the sun rises, longstanding markets such as Fausto’s Food Palace, a family-owned staple since the 1920s, fulfill gourmet grocery needs. Larger stores like Publix and retailers like T.J. Maxx and Ross Dress for Less are about 3 miles north in New Town.
Blue Heaven serves breakfast, lunch and dinner with live music from 10-2 and 4 to close.
Six toed cats can be spotted in the Hemingway House Museum in old Town Key West.
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Local troupes perform at the Red Barn Theatre
With everything from studio galleries to museums, Old Town is the beating heart of art and culture in Key West. Local troupes practice and perform at the Red Barn Theatre, housed in a historic red brick carriage house from the late 1820s. As one of Florida’s oldest professional theaters, its stage has been graced by Tennessee Williams, Shel Silverstein and Tony Roberts. The Key West Theater hosts acts from around the globe, while the Tropic Cinema highlights independent and international films under its Art Deco marquee. While some museums mainly attract tourists, others, like the Key West Museum of Art & History at the Custom House, welcome neighbors for happy hours, bingo nights and special speakers hosted by the city’s Art and Historical Society. Plus, many museums offer free or discounted admission to locals on select days.
Old Town is littered with historic buildings such as the Strand Theater.
Many bars and restaurants in Old Town have live music to entertain their guests.
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Island traditions include Hemingway Days, Key Lime Festival
Key West stays busy no matter the season, beginning the year with live music at the Mile 0 Fest and rounding out each December with a New Year’s Eve party at Mallory Square. In spring, Taste of Key West celebrates the city’s vibrant food culture. Come summer, locals look forward to the annual Key Lime Festival, which often coincides with the Fourth of July celebration and fireworks at Indigenous Park. Lobsterfest and Rum Fest are also summer highlights. But nothing compares to the turnout for Hemingway Days, a weeklong festival in July celebrating the famed author and late resident with lookalike contests, fishing challenges, street fairs and more. Fall brings the city’s renowned film fest and the annual Fantasy Fest, known for its energetic costume parties.
Key West High partners with the local college
Horace O’Bryant School, rated B on Niche, serves kindergarten through eighth grade students. Sections of the neighborhood are zoned for B-rated Gerald Adams Elementary School, about 4 miles away on Stock Island, but Monroe County’s choice enrollment system allows students to apply to any district school. B-plus-rated Key West High School offers dual enrollment courses with The College of the Florida Keys. The college also runs its own STEM-focused Academy Public Charter High School. Private schools in the area include Montessori Children’s School of Key West, which serves kindergarten through sixth grade, and The Basilica School of Saint Mary Star of the Sea, which recently reopened its high school program.
Key West High School is home to the fighting Conchs.
Gerald Adams Elementary Schools offers primary learning to students in the area.
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Old Town is pedestrian and bike-friendly
Old Town is a comfortable community for pedestrians and cyclists, with wide sidewalks, slow-moving traffic and ample bike racks. Car speed limits are low, especially on busy roads like Duval. But at 2 miles wide, the neighborhood is quick and easy to navigate. The Lower Keys Shuttle provides bus service throughout the city and offers routes to Marathon, 50 miles north. Key West International Airport is about 3 miles up the oceanside coast of the island.
Duval Street is the popular main street in Old Town with plenty of bars, eateries and retail.
Older homes built in the early 1900s are still prevalent around Old Town and Key West.
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The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
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to let others know what life in this neighborhood is like.
Crime and Safety
1 - Low Crime, 10 - High Crime
Old Town
US
Homicide
2
4
Sexual Assault
4
4
Assault with Weapon
4
4
Robbery
3
4
Burglary
5
4
Motor Vehicle Theft
5
4
Larceny
4
4
Crime Score
4
4
Source: WhatIsMyCrimeRisk.com
Old Town Demographics and Home Trends
On average, homes in Old Town, Key West sell after 113 days on the market compared to the national average of 53 days. The median sale price for homes in Old Town, Key West over the last 12 months is $1,435,277, up 20% from the median home sale price over the previous 12 months.
Centrally located in flood X zone of Old Town, this 2-bed, 2-bath townhouse is classic Key West charm at its best. The galley kitchen offers abundant cabinetry, granite countertops, and stainless-steel appliances. High ceilings with wood-finished crown molding add warmth and character throughout. The spacious primary suite showcases beautiful Dade County pine and a private en-suite bath. Central
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 the street, this three-bedroom, two-bath residence feels like a peaceful retreat while remaining close to Duval Street and the historic seaport. The outdoor living space features a beautiful pool and spa area surrounded by a
Sean FarrerColdwell Banker Schmitt Real Estate Co. (KW)
Welcome to your perfect Island Escape! Nestled in the heart of old town, this beautiful home is one you're sure to fall in love with. Featuring two off-street parking spaces and a private pool, it blends luxury, comfort, and convenience, perfect for both vacation getaways and year-round living. Inside, you'll find three spacious bedrooms and three modern bathrooms, designed to provide everything
Andy BirrellBerkshire Hathaway HomeServices Knight & Gardner Realty
Welcome to 524 Southard Street, an extraordinary luxury offering in the heart of Old Town Key West that blends upscale finishes, commercial versatility, & superior sustainable construction just steps from Duval Street. This fully renovated & Green-certified mixed-use property features 2,262 sq. ft. of refined interior space designed with modern industrial style & historic Key West character.
Discover a rare investment and lifestyle opportunity at 'Zen Villa,' a prestigious compound anchored in the coveted X-Flood Zone of Old Town, Key West. Spanning a spacious 5,891 SF lot, this unique offering encompasses three distinct residences: the luxurious main estate at 400 Aronovitz Lane and two charming, income-generating cottages at 621 and 623 Whitehead Street.The main residence is a
This gorgeous two-cottage property is located at the top of Solares Hill in the heart of Old Town Key West and offers exceptional flexibility along with strong rental and income potential. The lovely main house sits at the front of the property and features a main-floor primary bedroom and bath, an open living and dining area with vaulted ceilings, and central air. Stairs lead to a second bedroom
Step into timeless Key West charm at 206 Truman Avenue, a classic Conch cottage rooted in Key West's Bahama Village neighborhood soaked in tradition and nestled in the heart of Old Town. This historic residence effortlessly blends character and comfort, offering original architectural details, Dade County pine, and breezy porches that whisper stories of the island's rich past.Situated on a
Discover the timeless charm of this beautifully remodeled historic home located in Old Town, Key West. This fully furnished 3 bedroom, 2.5 bath property boasts lovingly restored Dade County Pine, and combines classic craftsmanship with modern comforts. 1211 Knowles Ln features a 300 sq.ft. loft currently used as a 3rd bedroom, office and storage ! Both front and side porches invite you to relax
Charming Key West Cottage with Pool, Rooftop Deck & Prime Old Town Location.Discover the ultimate island lifestyle in this lovely Key West cottage located in the vibrant heart of Old Town. Perfectly sized for effortless living, this beautifully maintained home offers all the charm, comfort, and convenience you could dream of--without the hassle of high-maintenance upkeep.From the moment you
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 step inside. Drawing inspiration from the rich architectural tapestry of Key West, this home thoughtfully weaves together Old Key West charm, Cuban mosaic tile accents, and contemporary finishes to create an atmosphere that feels
Welcome to Old Key West luxury living in this beautifully appointed 2-bedroom, 2-bathroom condo, ideally located in an X flood zone. This residence features hardwood floors, high ceilings, crown molding, granite countertops, and stainless steel appliances, creating a refined yet relaxed island aesthetic. The open-concept layout flows effortlessly for everyday living and entertaining, while the
Privacy. Seclusion. Serenity. Tucked away at the end of a quiet lane, 610 Griffin Lane is a rare Old Town retreat--an intimate, multi-structure compound that feels worlds away from the everyday.Set on an oversized lot nearly twice the size of most in the area, the property unfolds like a private estate. The beautifully renovated two-bedroom, two-bath main residence offers effortless comfort and
Nestled on a charming street in the heart of Old Town Key West, 1115 Varela Street is the renovation project that you have been waiting for. This historic treasure would be a perfect project for an investor, developer or anyone looking to restore a historic Key West gem. Currently configured as a 3BD/2BA with a large outside deck and an ideal positioned detached unfinished utility shed. The lot
Location, Location, Location! A renovation project that will increase the value of your investment exponentially! This home is located between the Southernmost Point and the Hemingway House in the world-renowned City of Key West Florida. Besides the excellent location, this home has concrete fences, a concrete gated entry from Whitehead Street, a nice sized rear deck/patio, front sitting/garden
Step outside to your own slice of paradise - a private oasis that beckons you to unwind and rejuvenate. The sparkling pool, adorned with stunning blue mosaic tiles, creates a mesmerizing focal point, while the soothing sound of its waterfall feature transports you to a world of tranquility. Surrounding the pool, a spacious deck provides the perfect setting for sunbathing, alfresco dining, or
Discover your place in the heart of Key West's most historic and vibrant neighborhood. The Lofts at Bahama Village offers affordable housing options designed for locals, where homeownership and rental opportunities meet the warmth of a close-knit community.Live steps away from iconic Key West landmarks, while enjoying the charm and cultural heritage that make Bahama Village truly one of a
Spacious 3-bedroom, 2-bath apartment located at 1110 White Street in Key West. Rent is $4,000 per month. Water, trash, and sewage are included; tenant is responsible for electricity.This unit is ideally situated steps from downtown, with a convenience store, Faustos Supermarket, and a pizza shop located right below the building. Enjoy easy island living with an approximately 10-minute walk to the
Experience the allure of this luxurious 2,000+ square foot penthouse, The Maloney, which occupies the entire second story of a historic red brick building at the corner of Fleming and Simonton. Originally constructed in 1908 as Key West's first pharmacy, this building now features two penthouse units and a first-floor boutique. The Maloney is available exclusively for monthly rentals, requiring a
Long term or short term rental, 4 bedroom, 2-bathroom furnished apartment is conveniently located just steps away from Duval Street, Mile Marker 0, and within walking distance to the Southernmost Point, Fort Zachary Taylor Historic State Park. The apartment boasts Beautiful bathrooms with walk-in showers, spacious kitchens equipped with upgraded stainless steel appliances, a stunning waterfall
Casa Azul is a luxurious modern cottage featuring an open-concept living area that is bathed in natural sunlight. Enjoy a dip in the heated saltwater plunge pool with a waterfall feature and night lighting. Located in Old Town Key West, just two blocks from Duval Street, this pet-friendly home offers private parking and is perfect for your next extended stay.Casa Azul perfectly blends comfort
Beautifully renovated Old Town second floor condo, furnished. High ceilings, freshly painted, and a wonderful front porch to relax on. Walk or Bike to everything Old Town, local restaurants, steps to Sandy's Cafe for your morning cuban coffee, Walk on White event, food store, and more! This unit has a beautiful kitchen with a dish washer, an in unit washer and dryer, and access to a shared pool.
Elaine CoyleKeller Williams Key West Compass Realty
Feel at home in this bright, modern 2-bedroom, 2-bath second-floor condo, ideal for comfortable long-term stays in Key West.Fully renovated in Summer 2024, the condo features an open-concept living area and a modern kitchen with new countertops, stainless steel appliances, and all home cooking essentials. Outside, relax by the shared heated pool or unwind in the grill and lounge area
Meticulously renovated 1866 Conch Revival perched atop Solaris Hill in the heart of Old Town and Steps from Old Town's vibrant culture, dining, and entertainment. This historic gem blends rich heritage with contemporary comforts offering an open Floor plan, 2 primary bedroom options (one on first level), cocktail pool, hammock porch and more! Step into the foyer at the corner of Southard & Love,
"Lil Bit" is a rare find in the historic Bahama Village neighborhood. This classic "conch" home is modern and renovated to have an elevated feel but retains the charm and character of old Key West. Perfect for a couple or visitors looking for a monthly stay, this home is equipped with everything you need. While it is a "Lil Bit," the space feels large, open, and fresh, and is a short walk to Fort
Southernmost View is a modern and luxurious waterfront home located in a private seven-home gated community, just steps from the beach and the Southernmost Point of the continental USA. Enjoy turquoise blue waters from the rooftop sundeck, perfect for tanning, reading, and sipping your morning coffee. Relax under the southernmost stars or watch the sunset over the horizon.This upscale beach
Lovely upstairs loft style apartment available now for LONG TERM.Located in upper old town Key West, near Bayview Park. Apartment is completely furnished, private full size W/D, gas range, large tiled shower, and covered deck for tropical outside living! All utilities and internet are included in rent! First and last mo rent required to move in. Property is very well maintained, and
Newly Renovated Townhome in Prime Old Town Key West located just 3 blocks from the beach! Experience the best of island living in this beautifully renovated 2-bedroom, 1.5-bath end-unit townhouse, perfectly situated in one of Key West's most sought-after neighborhoods. Features include a stunning new kitchen with quartz countertops, custom cabinetry, stainless steel appliances, and a handcrafted
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