Search for Homes in Mid Town East

Mid Town East - Key West

Mid-town is comprised of White Street from Truman Avenue (which becomes North Roosevelt Blvd. at Eisenhower Dr.) to Atlantic Blvd. running North to 8th Street just south of “The Flagler Ave. Canal”. Realtors have divided this large area into Mid-town East and Mid-town West. Mid-town West would be the lower part of this neighborhood where the architecture more closely resembles that of Old Town and The Meadows Conch Houses. Mid-town East would be north of George St. to 8th St.

Mid-town is traditionally home to long-time residents, families with children and renters. As the name implies, it is located in the middle of the island so it is close to downtown and Old Town as well as schools, grocery stores, banks, offices, shopping centers and sports complexes.

The island’s only high school, Key West High School (Go Conchs!), Horace O’Bryant (HOB) K-8 School, May Sands Montessori Charter Elementary School, Grace Lutheran Elementary School and The Key West Preschool Co-op are the schools within Mid-town.

Mid-town is a great area, especially for the first time home-buyer wishing to have their piece of paradise in the heart of Key West.

New Listings in Mid Town East

1901 S Roosevelt Blvd N Unit 208 N, Key West
$880,000
3 Beds ⋅ 2 Baths ⋅ 621608 MLS
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 second-floor end unit at La Brisa North adds privacy and offers a rare 3 bedroom & 2 bathroom floor-plan. 1,384 sqft, impact windows/doors, newer kitchen appliances, an in-unit washer and dryer, and tile floors throughout. Dedicated covered parking space with a storage closet in the carport. The HOA dues cover building insurances, a newly resurfaced pool (open 24 hours), hot tub, dry saunas, tennis and pickleball courts, an EV charging station, and car wash station. All assessments are paid in full. Pets and rentals allowed with restrictions.

1901 S Roosevelt Blvd N Unit 208 N, Key West
5 Mccoy Cir Unit # 5, Key West
$1,350,000
2 Beds ⋅ 3 Baths ⋅ 621523 MLS
DEEDED BOAT SLIP ON ISLAND! A standout waterfront opportunity in Key West, 5 McCoy Cir #5 offers the kind of coastal living that is hard to find: a townhome with a deeded boat slip, open water views, ample parking, and direct sightlines to your slip from the balcony. From the moment you enter, the unobstructed water views set the tone, creating a bright and relaxed setting across every level of the home. Designed for easy living, this 1,387 sq. ft. townhome features a smart three-level layout with generous storage, covered parking, and multiple outdoor spaces. The main living level includes an open kitchen and living area with a convenient half bath, all positioned to take full advantage of the wide water views. Step out to the large balcony and enjoy a front-row view of your boat slip, the surrounding water, and the open horizon beyond. The top floor offers two bedrooms, each with its own ensuite bathroom, creating comfortable private spaces with a clean and functional layout. Below, the covered garage area provides ample storage for boating gear, fishing equipment, bikes, tools, and everyday essentials. Plenty of storage to store your fresh catch, stone crabs, drinks, and supplies after a day on the water. The deeded boat slip is a true highlight, offering the ability to walk directly to your boat and enjoy the water with ease. The slip can comfortably fit a 25-foot boat with dual engines, making this a special option for those who value direct water access. A private patio adds another outdoor area to relax, rinse off, or organize gear before and after time on the boat. With dedicated parking, plenty of storage options, open water views from every level, and HOA coverage that includes insurance, this property brings together convenience, function, and the Key West waterfront lifestyle in one remarkable property. Come check it out by land or by boat -- pull up to the slip and we'll give you a tour!

5 Mccoy Cir Unit # 5, Key West
2911 Seidenberg Ave, Key West
$1,195,000
3 Beds ⋅ 2 Baths ⋅ 621482 MLS
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 inside to a spacious, open-concept living area designed for both relaxing and entertaining. The true highlight is the private backyard oasis -- featuring a sparkling pool surrounded by fresh tropical landscaping, an expansive deck, and plenty of room for outdoor dining and lounging. Whether hosting guests or enjoying a quiet evening under the palms, this outdoor retreat feels like your own private paradise. Recent renovations provide peace of mind, including new impact windows and doors, Hardie board siding, and other thoughtful upgrades. Off-street parking adds everyday convenience. Perfectly located in the desirable MidTown neighborhood, this home keeps you close to shopping, dining, and all the best of Key West living. Don't miss this opportunity to own a beautifully updated slice of paradise in Key West -- schedule your private showing today!

2911 Seidenberg Ave, Key West
5 Hilton Haven Dr, Key West
$1,695,000
4 Beds ⋅ 5 Baths ⋅ 621480 MLS
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 opportunity for a buyer with a vision. The 4-bedroom, 4.5 bath, 2,027 sq. ft. home that is currently divided into 4 separate units in need of extensive repair. Or this home could be a good candidate for rebuilding as your single-family dream home with a pool, separate pool house, and 60' of dockage. Tucked away on one of Key West's few private drives, the home enjoys limited traffic and added privacy. Equipped with 2 electric meters and 9,058 sq. ft. lot, this property offers options and flexibility for bringing your vision to life.

5 Hilton Haven Dr, Key West
2506 Seidenberg Ave, Key West
$799,000
3 Beds ⋅ 3 Baths ⋅ 621467 MLS
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 landscaping and a classic white picket fence, this home offers plenty of space and a flexible layout for comfortable island living. The main living area flows into a large eat-in kitchen featuring abundant cabinetry, stainless steel appliances, generous counter space, and plenty of room for dining and entertaining. Three bedrooms and three full baths provide ample accommodations, while additional living space at the rear of the property offers added flexibility for guests, a home office, den, or private retreat. A garage provides valuable parking and storage. Centrally located just minutes from Old Town, beaches, shopping, dining, and all that Key West has to offer. With nearly 2,000 square feet, versatile additional living space, a garage, and a convenient Midtown location, 2506 Seidenberg Avenue presents a unique opportunity to make a Key West home your own. Owner financing may be available.

2506 Seidenberg Ave, Key West
1901 S Roosevelt Blvd Unit N104, Key West
$849,000
2 Beds ⋅ 2 Baths ⋅ 621436 MLS
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 Smathers beach. Situated directly across the street from the shoreline, this bright and airy residence offers the perfect blend of comfort, convenience, and coastal charm. Inside, you'll find a spacious open-concept living and dining area filled with natural light, a modern kitchen , and two generously sized bedrooms with ample closet space. The primary suite features a private en-suite bathroom, while the second bedroom is ideal for guests or a home office. Relax on your private balcony with peaceful Salt Pond views, or take a short stroll across the street to sink your toes in the sand. This condo also offers amenities such as assigned parking, in-unit laundry, and access to a community pool, tennis courts and clubhouse. Perfect as a primary residence, weekend retreat, or investment property--this is beachside living made easy! Call for your private tour today !

1901 S Roosevelt Blvd Unit N104, Key West
2519 Staples Ave, Key West
$1,575,000
4 Beds ⋅ 4 Baths ⋅ 621374 MLS
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 bicyclable and desirable streets in Midtown. Recently completed renovations offer the opportunity to be the first to live in this thoughtfully rethought home, where modern upgrades meet relaxed island living. Spanning approximately 2,100 sq ft, the property features 4 bedrooms and 3.5 bathrooms, with a layout designed for both comfort and functionality. The primary suite serves as a private retreat, complete with direct access to the backyard, a spacious walk-in closet, and a beautifully appointed ensuite bathroom. Outdoor living is where this home truly stands out. A newly installed pool with elegant deck jets creates a serene, resort-style setting, fully enclosed for privacy. The new addition of a bright and airy pool room offers a seamless indoor-outdoor flow- perfect for entertaining or unwinding. There is a separate sitting and dining area for eating and lounging el fresco. Beautiful mature fruit trees provide shade and produce fruit annually. Additional upgrades include all impact windows and doors, providing peace of mind and energy efficiency throughout. New sewer and plumbing pipes to the road. New electrical and a new water heater. There is plenty of parking for a boat, a truck, a golf cart and a car. Properties offering this combination of lot size, location, and new construction-level renovations are exceptionally rare in Key West. Whether you're seeking a full-time residence, a family home, or a vacation retreat, this property delivers. House is being offered fully furnished minus personal items, art, and rugs. A true standout opportunity in Midtown, don't miss it!

2519 Staples Ave, Key West
2623 Gulfview Dr, Key West
$2,400,000
3 Beds ⋅ 3 Baths ⋅ 621218 MLS
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 waterfront lifestyle and just minutes from world-famous Duval Street and all that Key West has to offer. This move-in-ready 3-bedroom, 2.5-bath home welcomes you with classic Key West architecture, lush tropical surroundings, and inviting indoor and outdoor living spaces. The kitchen features granite countertops, stainless steel appliances, and ample cabinetry. Step outside to your own private tropical retreat, where a sparkling pool surrounded by composite decking creates the perfect setting for relaxing, entertaining, and enjoying the year-round Florida Keys sunshine. Beyond the pool, your private dock opens the door to endless adventures. Spend the afternoon fishing, set out on your personal watercraft, paddleboard or kayak, or simply unwind and watch another spectacular Key West sunset from your own backyard. A covered carport and the privacy of a gated community complete this island home. Whether you're searching for a full-time residence, your own Key West getaway, or investment opportunity with luxury vacation rental potential in this highly sought-after community, Gulfview Pointe offers an exceptional opportunity. Opportunities like this don't come around often--invest in your dream home and start living the Key West waterfront lifestyle you've been dreaming of. Call today to schedule your private showing!

2623 Gulfview Dr, Key West
2012 Roosevelt Dr, Key West
$900,000
3 Beds ⋅ 2 Baths ⋅ 621028 MLS
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 find spacious bedrooms, ample storage and plenty of square footage for comfortable living. Enjoy a private outdoor area with endless possibilities for relaxing, entertaining or creating your own tropical retreat. Conveniently located near Old Town Key West, marinas, shopping, dining and all that Key West has to offer. This Home has no HOA Fees and enough space to store a boat and trailer. The Square Footage , Location and Price make it an Excellent Value!

2012 Roosevelt Dr, Key West
2001 Flagler Ave, Key West
$299,000
620958 MLS
2,244 square foot commercial zoned lot would be ideal for one or more food vendor trucks, with excellent visibility and heavy traffic. Make an offer today!

2001 Flagler Ave, Key West
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