Midtown Key West offers a balance of convenience and comfort, with single-family homes on quiet streets just minutes from both Old Town and New Town. This centrally located neighborhood is popular with full-time residents seeking a more local feel while staying close to everything the island has to offer.
Old Town Key West – Historic charm, walkability, and classic conch homes
Casa Marina District – Upscale and residential, near beaches
New Town Key West – Suburban-style homes, shopping, and schools
Beyond the Island: Homes in the Keys Near Key West – Including Stock Island, Key West Golf Club, Key Haven, Rockland Key, Shark Key, Geiger Key, Big Coppitt, and more
Browse homes for sale in Midtown Key West, including a variety of mid-century and updated residential properties.
This stunning 3 bedroom penthouse condo overlooks the ocean, pool, and has a bird's eye view of the Gulf. Brilliant white, crisp kitchen with updated appliances and sma...
Tropical outdoor living meets the comfort of newer construction at 1607 Sunshine Drive! Built in 2014 this 3 bedroom 3 bath home offers a wonderful combination of privacy...
Double waterfront MM 2 in Key West. Presenting a rare opportunity to acquire a distinguished single-family waterfront home on highly desired Hilton Haven Drive, a truly u...
Discover the charm of coastal living at Casa Caselles, an exclusive 19-residence gated community nestled along the Atlantic Ocean in Key West. This inviting two-bedroom, ...
Welcome to 1809 Seidenberg nestled in Mid Town Key West with one of the larger pools on the island. The open floor plan with an entire wall of pocket sliders provide the ...
BRAND NEW CONSTRUCTION MIDTOWN WEST Meticulously crafted by a local luxury builder, this exceptional new 4 bedroom 3 bath residence combines superior construction, th...
Nestled within a private tropical oasis on a 7,500-square-foot lot, this charming Mid-Century Modern home offers the perfect blend of architectural character and island l...
Nestled in a tranquil ,established neighborhood ,this property offers an opportunity for those looking to enjoy the charm of an existing home or envision something entire...
Beach Living | 3-Bedroom End Unit | Salt Pond Views | Gated Community Cross the street to Smathers Beach, then come home to an open balcony over the salt ponds. This sec...
Close to Duval Street but away from the hubbub, this immaculately presented one bedroom condo is just a few blocks from Smathers Beach and vibrant White Street with its r...
BOAT SLIP INCLUDED WITH OWNERSHIP! A standout waterfront opportunity in Key West, 5 McCoy Cir #5 offers the coastal lifestyle you've been looking for: a townhome-style...
Situated on a spacious corner lot in desirable Midtown West, 1221 Ashby Street offers the perfect blend of comfort, privacy, and island living. The main residence feature...
Ideally located just two blocks from the beach, this beautifully renovated Key West residence blends island living, modern comfort, and plenty of space to make it your ow...
Welcome to your dream home in the heart of Key West's MidTown! This beautifully updated 3-bedroom, 2-bathroom residence blends modern comfort with island charm. Step insi...
LOCATION! Situated on Garrison Bight, across the canal from the Key West Yacht Club, 5 Hilton Haven Dr. provides the best boating access on Key West. Tremendous opportuni...
Discover the perfect blend of transient investment potential and coastal charm on Atlantic Boulevard. Just steps from the beach, this exceptional property offers a truly ...
Welcome to 2506 Seidenberg Avenue, a spacious 3-bedroom, 3-bath home offering 1,922 square feet of living space in the heart of Midtown Key West. Framed by tropical lands...
There is a certain rhythm to life in Key West. Mornings begin outside, friends have a way of staying longer than planned, and some of the best evenings never make it past...
Completed in 2025, this brand-new, elevated two-story home rises above the surrounding homes and is built above flood level. Excellent location close to the beach. Catego...
Coastal Living at Its Finest - 2-Bedroom Condo at La Brisa ! Wake up to ocean breezes in this beautifully appointed 2-bedroom, 2-bathroom condo located just steps from Sm...
Life is BETTER at the Beach! Enjoy penthouse style living with panoramic ocean views from this two story oceanfront condo! This waterfront setting is simply serene, pea...
Welcome to 2519 Staples Avenue, a fully reimagined residence in the heart of Midtown Key West, set on a rare 10,000 sq ft corner lot along one of the area's most bicyclab...
Welcome to your waterfront escape in Key West. Located within a gated community, Gulfview Pointe offers the perfect blend of island charm, comfort, and an exceptional wat...
If you are seeking a private tropical backyard oasis look no further. This charming 2 story home is situated on a corner parcel in a quiet and peaceful mid town neighborh...
Set on a quiet, tree-lined block in one of Key West's most sought-after residential pockets, this thoughtfully reimagined 4BD/3BA residence offers just over 2,000 square ...
Exquisite, turnkey resort living awaits in this fully furnished 2-bedroom, 2-bathroom oceanfront condominium, offering an effortless transition into Key West luxury just ...
Your place in Key West awaits. Located in Midtown, just minutes from the energy of Duval Street, this updated two-unit property offers the flexibility to live here, escap...
Welcome to 1724 Rose Street, a spacious single-family home on a generous corner lot in a quiet Midtown neighborhood, close to Key West's beautiful beaches. The main lev...
Centrally located and well-built, this spacious Key West townhome offers generous off-street parking with plenty of room for golf carts, an RV and guests. Inside, you'll ...
Charming Key West living in a fantastic central location! This inviting end-unit condo offers an easy, low-maintenance opportunity to own a piece of the island, whether y...
Get excited about this mid-town oasis. Behind the fence is a charming three-bedroom three bath residence with beautiful grounds, off-street parking, newer roof, impact g...
Positioned directly across South Roosevelt Boulevard from Smathers Beach, it blends high-end modern finishes with expansive views of Key West's tranquil salt ponds. Inter...
Located in the Beach Club, this reimagined residence offers a rare combination of luxury, privacy, and oceanfront living within one of Key West's premier & financially se...
Welcome to an extraordinary oceanfront residence in the exclusive Casa Caselles community, where two townhomes have been masterfully combined into one spectacular 4,224 s...
THIS IS THE PLAY. Big lot. Big upside. Atlantic Boulevard address. 1503 Atlantic Boulevard brings together the pieces that matter most in Key West: land, location, pool, ...
Duplex has 1,342 square feet of living space on a 2,841 square foot lot with 2 two bedroom one units generating $74,400.00 annually. Units have been recently renovated an...
When value matters, this solid concrete New Town home stands apart with one of the most compelling price-per-square-foot opportunities on the market. Substantial 4-bedroo...
Coastal Living at 1800 Atlantic - where everyday life is framed by ocean breezes and turquoise water. This highly sought-after oceanfront condominium community offers th...
There is almost nothing like this in Key West: a 2007-built home, raised from the ground up to modern standards. Rare, move-in ready, and free of the surprises that come ...
Charming Key West Cottage with large back yard and ROOM FOR A BIG POOL! Pack your flip flops and leave your worries at the door! This enchanting Key West gem is ready to ...
Welcome to 2317 Fogarty Avenue, a beautifully updated 3-bedroom, 2-bathroom home ideally located in the heart of Key West. Combining modern upgrades with island charm, th...
Discover the perfect blend of island charm, comfort, and versality in this exceptional Key West property featuring a main residence and a spacious guest house. The main h...
Major price improvement for an amazing full ocean view penthouse unit! Presumably the best view in the preferred South Wing of La Brisa Condominiums, enjoy a panoramic vi...
With only two owners in its history, this well-maintained two-story property presents a rare investment opportunity in Key West. Configured as a legal duplex with two sep...
Sweeping Gulf views. Private deeded boat dockage. Effortless Key West elegance. Situated in the coveted enclave of Flagler's Landing, this elevated waterfront residence ...
Welcome to this beautifully renovated 3-bedroom, 2-bathroom home that perfectly blends modern finishes with warm, inviting living spaces. From the moment you arrive, you'...
Endless possiblities! Two units to rent for the investor or live in one and produce income from the other unit. Downstairs you have a 3/1.5 with an open floor plan and ...
This spacious two-bedroom, two-bath penthouse condo boasts a stunning balcony with ocean views, making it the perfect place to relax and enjoy the breathtaking scenery. ...
With only two owners in its history, this well-maintained two-story property presents a rare investment opportunity in Key West. Configured as a legal duplex with two sep...
Seclusion meets striking contemporary design in this elevated sanctuary, positioned just moments from Higgs Beach and White Street Pier. Behind a signature pivoting red g...
Built in 2008, this expansive 3,220 sq ft residence sits on a nearly 5,000 sq ft lot and offers the perfect blend of comfort, style, and location. Centrally situated, you...
Some homes invite you in, and others make you want to stay. 1220 Georgia Street does both. Tucked into a quiet pocket of Old Town on a corner lot, the home feels peacefu...
Key West Oasis - A Tropical Compound Steps from the Sea. House, Pool & Guest Retreat located near by Casa Marina and steps from Old Town. Welcome to your own private trop...
Two Parcels Included!!! Welcome to 1320 6th Street, a fantastic investment opportunity in a prime midtown Key West location. This property features three private units...
Welcome to your dream home in Midtown Key West! This 4-bedroom, 3-bathroom currently being used as a 3/2 with a mother-in-law suite. This property has endless possibiliti...
This rare TRANSIENTLY licensed condo is designed to embrace tropical luxury exuding natural light, open concept, practicality and privacy thus creating a serene and invit...
Builder/Contractors Dream ! Rare 4 unit new development opportunity, 7,000 square ft lot available in Midtown Key West.
Price Reduction. Excellent opportunity to purchase a luxurious, modern, and refined single-family home in one of the best neighborhoods in Key West. This 4bed/3bath compl...
**Key West Pool Home on a Double Lot -- 4 Bedroom, 3 Bathroom CBS, Parking for 4** ALL THE STUFF! 1719 Laird Stre...
2br/1.5ba - Ocean Views from this beautifully renovated Key West by The Sea condo on Smathers Beach. This 2-bedroom, 1.5-bath residence feels like new construction, featu...
Discover the essence of island living in this expansive 3,197sf, 6-bedroom, 3-bathroom home, perfectly positioned on a generous 9,500sf corner lot in the heart of Key Wes...
Wake up to breathtaking direct ocean views from this second-floor, 1-bedroom, 1-bath residence located in the desirable 'A' building at Key West by the Sea. This bright a...
POOL & POOL HOUSE COMPLETED! Opportunity awaits to create your perfect midtown home. This property consists of a partially updated main home totaling 1233 sq ft with 2bd/...
EXCELLENT OPPORTUNITY! EXCELLENT LOCATION! OWNER FINANCING AVAILABLE! This duplex offers several terrific options for the buyer -- from building a brand new single...
Tare Down You can build your dream house to your specifications just 4 houses to the beach. Close to the White Street pier. Walk to pickle ball and tennis courts. Higgs b...
This versatile 3-family property offers a rare blend of privacy & income potential. Designed as 3 distinct residences, each with a private entrance and it's own kitchen a...
Discover the rare opportunity to own a premier developer's unit in one of Key West's most desirable waterfront communities. Perfectly positioned just across the street fr...
Rare WATERFRONT home on the island of Key West, an incredible value priced well below the last comparable sale. Tucked behind the gates of the exclusive Gulf View Pointe ...
1501 Georgia Street is a masterclass in design. Conceived by local architect Rob Delaune and set within lush, museum worthy grounds by renowned landscape architect Raymon...
Development Opportunity. (4) townhouse unit complex situated on a heavily landscaped 10,000 sq ft parcel. Comprised of (2) side by side duplexes legally subdivided as ( 4...

Jim Signor: 305-394-4449