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.
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...
Owner Financing Available - Flexible Terms! Rare opportunity in Midtown Key West! This cleared and vacant 75x100 lot--a true rarity on the island--is ready for your drea...
1706 Seminary Street delivers the space, flexibility, and outdoor lifestyle that can be surprisingly difficult to find in Key West. Set behind a new privacy fence on an e...
Tucked into the leafy heart of Midtown, just a quick bike ride from Smathers Beach, Higgs Beach and the energy of downtown, 1708 South St. offers something increasingly r...
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 with adjoining commercial lot for sale. Duplex has 1,342 square feet of living space on a 2,841 sq ft lot with 2 two bedroom one units generating $74,400.00 annual...
Duplex with adjoining commercial lot for sale. Duplex has 1,342 square feet of living space on a 2,841 sq ft lot with 2 two bedroom one units generating $74,400.00 annual...
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 ...
Welcome to Your Own Slice of Paradise! Pack your flip flops and leave your worries at the door! This enchanting Key West gem is ready to make your island dreams a reality...
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...
Turnkey luxury retreat in Midtown Key West, 4 blocks from the Atlantic. Fully fenced corner lot with fresh exterior paint and mature tropical landscaping. 3 bed/3 bath sp...
1627 Johnson St. -- A Legacy of Design, A Life Fully Lived. Some homes reveal themselves slowly -- and this is one of them. Designed by the late Michael Ingram, one of K...
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...
**Low Insurances totaling $4300/year** Furnished and move in ready, this beautifully appointed Midtown Key West half townhouse offers the perfect blend of comfort and is...
TRANSIENT investment opportunity awaits. Spacious 2bd/2ba situated in the centrally located waterfront community of 1800 Atlantic. Large covered balcony overlooks a lush ...
Improved $40,000 Lower Price for an Amazing Full Ocean View, Top Floor Unit! Presumably the best view in the preferred South Wing of La Brisa Condominiums, enjoy a panora...
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...
If you've been searching for a move-in ready slice of Key West in the heart of Midtown, 1825 Venetia Street delivers. This renovated 2-bedroom, 1-bath concrete block home...
Experience the quintessential island lifestyle in this stunning waterfront townhome at Flagler's Landing, where Gulf views meet the convenience of a central Key West loca...
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'...
A premier transient investment opportunity and a genuinely enchanting way of living meet on Atlantic Boulevard! The Atlantis House is a property with heart and soul. Just...
A premier transient investment opportunity and a genuinely enchanting way of living meet on Atlantic Boulevard! The Atlantis House is a property with heart and soul. Just...
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...
Endless possiblities! Three units to rent for the investor or live in one and produce income from the other units. Downstairs you have a 3/1.5 with an open floor plan a...
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...
MOTIVATED SELLER | There is a reason so many locals dream about living on Von Phister Street. The mature trees create shade across the wide streets, the neighborhood feel...
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...
Duplex with Solid Income - $91,800/Year This income-producing duplex offers two spacious units, each featuring 3 bedrooms and 1 bathroom--an ideal setup for steady, long...
Right in the heart of Key West, this income-producing triplex is the kind of property investors are always asking for--strong numbers, solid layout, and a location that n...
Substantial price improvement. Motivated seller. This well-maintained 2-bedroom condo has just hit the market and is truly priced to sell. Offered turnkey and newly fur...
First time ever on the market! This is an excellent opportunity to own a charming single-family home in Key West. Lovingly maintained and custom-built for the current own...
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...
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...
MOTIVATED SELLER! The perfect Key West starter home. This charming CBS single-family residence is situated in Midtown. The interior shines with recent upgrades, including...
Architect-designed and purpose-built for modern island living, 1614 Washington Street delivers a rare combination of durability, intelligence, and refined restraint. This...
Welcome to your ideal island escape at 1607 Sunshine Drive in vibrant Key West, FL! This newer-construction 2014 single-family home offers the modern coastal lifestyle yo...
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...
Pool. Space. Privacy. -- Rare Double Lot Living in Key West 1719 Laird Street offers the space and upgrades buyers search for but rarely find in Key West. Set on an over...
Spectacular sunrise 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 constructio...
Don't miss this rare opportunity to own a legal duplex on a spacious 10,000 SqFt corner lot! The main residence, solid CBS construction, offers 2 bedrooms, 2 bathrooms, a...
Licensed for nightly Rentals! On average 120k/yr. Introducing an exquisite offering at one of Key West's sought-after waterfront resorts, 1800 Atlantic Blvd. A completel...
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...
SELLER FINANCING AVAILABLE! Seller willing to negotiate terms for owner financing while you develop this parcel. Options are open as Seller wants to move this property...
Located in a charming midtown neighborhood sits this beautifully renovated 4BD/2.5BA Key West home with just over 2,000sf of living space. Upon entering the home you will...
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...
30 foot pool, 3 bedroom, 2 bath home on a large, beautifully landscaped lot in Midtown West, Key West. Now $1.143m. Four blocks from the beach, 1713 Rose is nestled away ...
This is the one you've been waiting for! Unlike any other 2 bed listing available in Casa Caselles, this exceptional oceanfront home has been completely reimagined from t...
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/...
Welcome to 1718 United Street, a beautifully renovated home in the heart of Key West offering modern comfort with timeless island charm. This spacious residence features ...
EXCELLENT OPPORTUNITY! EXCELLENT LOCATION! This duplex offers several terrific options for the buyer -- from building a brand new home in a prime location to a top to ...
Renovated Midtown Key West Home | 2BR/2BA | 1,118 SF | Taken to Studs in 2021 | Off-Street Parking | Private Yard with Hot Tub. Just 5 Blocks to the Atlantic Ocean and be...
This Residential Duplex can be purchased alone or with adjacent property located at 1610 Laird. Street. Owner financing possible. Long term rentals are in place with grea...
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...
Welcome to 2016 Fogarty Avenue in Midtown Key West -- a charming 2-bedroom, 1-bath wood-frame home situated on a full 5,000 sq. ft. lot in one of the island's up-and-comi...
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...
Spacious and well-designed 3-bedroom, 2-bathroom home offering a flexible and functional floor plan perfect for today's lifestyle. The main level features an open kitchen...
Located in the heart of Key West, 1712 Laird Street offers a rare blend of central convenience and residential tranquility. Positioned within a short stroll of Smathers B...
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...
Opportunity awaits in the heart of Midtown Key West! This rare double-lot offering includes two side-by-side parcels with endless potential for redevelopment or renovatio...
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 ...
Welcome to 1720 United Street — a rare opportunity to own a spacious, build-ready lot in one of Key West's most desirable residential neighborhoods. Surrounded by mature ...
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...
This property can also be purchased along with the adjacent property 1612 Laird. Owner financing possible. Three bedrooms with room for expansion along with a guest room...
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