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Mid Town Homes for Sale

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.

More Key West Real Estate for sale

  • 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.

Mid Town Homes for Sale

2601 S Roosevelt Blvd Unit 610A, Key West image
2601 S Roosevelt Blvd Unit 610A, Key West $995,000

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...

  • 3 Beds
  • 2 Baths
  • 621777 MLS
1607 Sunshine Dr, Key West image
1607 Sunshine Dr, Key West $1,929,000

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...

  • 3 Beds
  • 3 Baths
  • 621721 MLS
18 Hilton Haven Road, Key West image
18 Hilton Haven Road, Key West $5,195,000

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...

  • 5 Beds
  • 6 Baths
  • 621709 MLS
1616 Atlantic Blvd Unit APT 18, Key West image
1616 Atlantic Blvd Unit APT 18, Key West $1,449,000

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, ...

  • 2 Beds
  • 3 Baths
  • 621689 MLS
1809 Seidenberg Ave, Key West image
1809 Seidenberg Ave, Key West $1,650,000

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 ...

  • 3 Beds
  • 2 Baths
  • 621680 MLS
1618 South Street, Key West image
1618 South Street, Key West $4,400,000

BRAND NEW CONSTRUCTION MIDTOWN WEST Meticulously crafted by a local luxury builder, this exceptional new 4 bedroom 3 bath residence combines superior construction, th...

  • 4 Beds
  • 3 Baths
  • 621671 MLS
2309 Flagler Ave, Key West image
2309 Flagler Ave, Key West $999,000

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...

  • 3 Beds
  • 2 Baths
  • 621670 MLS
1703 South Street, Key West image
1703 South Street, Key West $1,599,000

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...

  • 3 Beds
  • 2 Baths
  • 621633 MLS
1901 S Roosevelt Blvd N Unit 208 N, Key West image
1901 S Roosevelt Blvd N Unit 208 N, Key West $880,000

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...

  • 3 Beds
  • 2 Baths
  • 621608 MLS
1500 Seminary St Unit APT 2D, Key West image
1500 Seminary St Unit APT 2D, Key West $515,000

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...

  • 1 Beds
  • 1 Baths
  • 621586 MLS
5 Mccoy Cir Unit # 5, Key West image
5 Mccoy Cir Unit # 5, Key West $1,350,000

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...

  • 2 Beds
  • 3 Baths
  • 621523 MLS
1221 Ashby St, Key West image
1221 Ashby St, Key West $1,399,000

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...

  • 3 Beds
  • 3 Baths
  • 621518 MLS
1423 Rose St, Key West image
1423 Rose St, Key West $1,895,000

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...

  • 4 Beds
  • 4 Baths
  • 621516 MLS
2911 Seidenberg Ave, Key West image
2911 Seidenberg Ave, Key West $1,100,000 ▼

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...

  • 3 Beds
  • 2 Baths
  • 621482 MLS
5 Hilton Haven Dr, Key West image
5 Hilton Haven Dr, Key West $1,595,000 ▼

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...

  • 4 Beds
  • 5 Baths
  • 621480 MLS
1401 Atlantic Blvd, Key West image
1401 Atlantic Blvd, Key West $3,295,000 ▼

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 ...

  • 5 Beds
  • 4 Baths
  • 621476 MLS
2506 Seidenberg Ave, Key West image
2506 Seidenberg Ave, Key West $799,000

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...

  • 3 Beds
  • 3 Baths
  • 621467 MLS
1614 Washington St, Key West image
1614 Washington St, Key West $4,300,000

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...

  • 4 Beds
  • 5 Baths
  • 621463 MLS
1716 Laird St, Key West image
1716 Laird St, Key West $2,195,000

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...

  • 3 Beds
  • 2 Baths
  • 621461 MLS
1901 S Roosevelt Blvd Unit N104, Key West image
1901 S Roosevelt Blvd Unit N104, Key West $849,000

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...

  • 2 Beds
  • 2 Baths
  • 621436 MLS
1500 Atlantic Blvd Unit 414, Key West image
1500 Atlantic Blvd Unit 414, Key West $2,650,000

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...

  • 3 Beds
  • 2 Baths
  • 621379 MLS
2519 Staples Ave, Key West image
2519 Staples Ave, Key West $1,487,000 ▼

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...

  • 4 Beds
  • 4 Baths
  • 621374 MLS
2623 Gulfview Dr, Key West image
2623 Gulfview Dr, Key West $2,400,000

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...

  • 3 Beds
  • 3 Baths
  • 621218 MLS
1300 Seminary St, Key West image
1300 Seminary St, Key West $2,250,000

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...

  • 3 Beds
  • 4 Baths
  • 621172 MLS
1427 Washington St, Key West image
1427 Washington St, Key West $2,525,000

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 ...

  • 4 Beds
  • 3 Baths
  • 621162 MLS
1800 Atlantic Blvd Unit 325C, Key West image
1800 Atlantic Blvd Unit 325C, Key West $995,000

Exquisite, turnkey resort living awaits in this fully furnished 2-bedroom, 2-bathroom oceanfront condominium, offering an effortless transition into Key West luxury just ...

  • 2 Beds
  • 2 Baths
  • 621152 MLS
1300 Ashby St, Key West image
1300 Ashby St, Key West $1,350,000

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...

  • 4 Beds
  • 2 Baths
  • 621134 MLS
1724 Rose St, Key West image
1724 Rose St, Key West $1,490,000

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...

  • 5 Beds
  • 4 Baths
  • 621031 MLS
2012 Roosevelt Dr, Key West image
2012 Roosevelt Dr, Key West $900,000 ▼

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 ...

  • 3 Beds
  • 2 Baths
  • 621028 MLS
1332 Seminary St Unit 103, Key West image
1332 Seminary St Unit 103, Key West $575,000

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...

  • 2 Beds
  • 1 Baths
  • 620957 MLS
2309 Patterson Ave, Key West image
2309 Patterson Ave, Key West $995,000

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...

  • 3 Beds
  • 3 Baths
  • 620923 MLS
1901 S Roosevelt Blvd Unit 407N, Key West image
1901 S Roosevelt Blvd Unit 407N, Key West $625,000

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...

  • 1 Beds
  • 1 Baths
  • 620905 MLS
1500 Atlantic Blvd Unit 308, Key West image
1500 Atlantic Blvd Unit 308, Key West $4,499,999

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...

  • 3 Beds
  • 3 Baths
  • 620745 MLS
1616 Atlantic Blvd Unit 11, Key West image
1616 Atlantic Blvd Unit 11, Key West $4,995,000

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...

  • 4 Beds
  • 5 Baths
  • 620618 MLS
1503 Atlantic Blvd, Key West image
1503 Atlantic Blvd, Key West $1,095,000 ▼

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, ...

  • 4 Beds
  • 5 Baths
  • 620612 MLS
1421-1425 2nd St, Key West image
1421-1425 2nd St, Key West $799,000 ▼

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...

  • 4 Beds
  • 2 Baths
  • 620461 MLS
1500 5th St, Key West image
1500 5th St, Key West $979,000

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...

  • 4 Beds
  • 2 Baths
  • 620453 MLS
1800 Atlantic Blvd Unit 218B, Key West image
1800 Atlantic Blvd Unit 218B, Key West $950,000

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...

  • 2 Beds
  • 2 Baths
  • 620451 MLS
2313 Fogarty Ave, Key West image
2313 Fogarty Ave, Key West $1,385,000 ▼

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 ...

  • 3 Beds
  • 2 Baths
  • 620448 MLS
2005 Fogarty Ave, Key West image
2005 Fogarty Ave, Key West $745,000 ▼

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 ...

  • 3 Beds
  • 2 Baths
  • 620436 MLS
2317 Fogarty Ave, Key West image
2317 Fogarty Ave, Key West $889,000 ▼

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...

  • 3 Beds
  • 2 Baths
  • 620435 MLS
1523 Seminary St, Key West image
1523 Seminary St, Key West $1,799,765

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...

  • 3 Beds
  • 3 Baths
  • 620197 MLS
1901 S Roosevelt Blvd Unit 401S, Key West image
1901 S Roosevelt Blvd Unit 401S, Key West $890,000 ▼

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...

  • 2 Beds
  • 2 Baths
  • 620086 MLS
1911 Seidenberg Ave, Key West image
1911 Seidenberg Ave, Key West $1,250,000

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...

  • 2 Beds
  • 2 Baths
  • 620075 MLS
9 Mccoy Cir Unit 9, Key West image
9 Mccoy Cir Unit 9, Key West $1,249,000 ▼

Sweeping Gulf views. Private deeded boat dockage. Effortless Key West elegance. Situated in the coveted enclave of Flagler's Landing, this elevated waterfront residence ...

  • 2 Beds
  • 2 Baths
  • 620045 MLS
2116 Fogarty Ave, Key West image
2116 Fogarty Ave, Key West $1,249,000

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'...

  • 3 Beds
  • 2 Baths
  • 620013 MLS
1504 Flagler Ave, Key West image
1504 Flagler Ave, Key West $1,499,999 ▼

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 ...

  • 7 Beds
  • 5 Baths
  • 619911 MLS
1800 Atlantic Blvd Unit 427C, Key West image
1800 Atlantic Blvd Unit 427C, Key West $1,025,000

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. ...

  • 2 Beds
  • 2 Baths
  • 619778 MLS
1911 Seidenberg Ave, Key West image
1911 Seidenberg Ave, Key West $1,250,000

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...

  • 2 Beds
  • 2 Baths
  • 619758 MLS
1701 Laird St, Key West image
1701 Laird St, Key West $2,900,000

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...

  • 2 Beds
  • 2 Baths
  • 619715 MLS
1320 South Street, Key West image
1320 South Street, Key West $2,895,000

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...

  • 4 Beds
  • 5 Baths
  • 619665 MLS
1220 Georgia St, Key West image
1220 Georgia St, Key West $1,899,000 ▼

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...

  • 4 Beds
  • 3 Baths
  • 619619 MLS
1501 White St, Key West image
1501 White St, Key West $2,880,000 ▼

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...

  • 4 Beds
  • 3 Baths
  • 619469 MLS
1320 6th St, Key West image
1320 6th St, Key West $2,200,000

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...

  • 5 Beds
  • 4 Baths
  • 619406 MLS
1524 5th St, Key West image
1524 5th St, Key West $919,000 ▼

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...

  • 4 Beds
  • 3 Baths
  • 619376 MLS
1901 S Roosevelt Blvd Unit 202 W, Key West image
1901 S Roosevelt Blvd Unit 202 W, Key West $1,190,000 ▼

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...

  • 2 Beds
  • 2 Baths
  • 618408 MLS
2016 Roosevelt Dr, Key West image
2016 Roosevelt Dr, Key West $1,300,000

Builder/Contractors Dream ! Rare 4 unit new development opportunity, 7,000 square ft lot available in Midtown Key West.

  • 7 Beds
  • 5 Baths
  • 618731 MLS
1501 Florida St, Key West image
1501 Florida St, Key West $2,595,000 ▼

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...

  • 4 Beds
  • 3 Baths
  • 614088 MLS
1719 Laird St, Key West image
1719 Laird St, Key West $1,850,000 ▼

**Key West Pool Home on a Double Lot -- 4 Bedroom, 3 Bathroom CBS, Parking for 4** ALL THE STUFF! 1719 Laird Stre...

  • 4 Beds
  • 3 Baths
  • 616978 MLS
2601 S Roosevelt Blvd Unit 406A, Key West image
2601 S Roosevelt Blvd Unit 406A, Key West $928,000 ▼

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...

  • 2 Beds
  • 2 Baths
  • 617688 MLS
1229 5th St, Key West image
1229 5th St, Key West $1,899,000

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...

  • 6 Beds
  • 3 Baths
  • 611164 MLS
2601 S Roosevelt Blvd Unit 204A, Key West image
2601 S Roosevelt Blvd Unit 204A, Key West $599,000 ▼

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...

  • 1 Beds
  • 1 Baths
  • 618286 MLS
1505 Johnson St, Key West image
1505 Johnson St, Key West $1,449,000 ▼

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/...

  • 3 Beds
  • 3 Baths
  • 617589 MLS
1432 Eliza St, Key West image
1432 Eliza St, Key West $799,000 ▼

EXCELLENT OPPORTUNITY! EXCELLENT LOCATION! OWNER FINANCING AVAILABLE! This duplex offers several terrific options for the buyer -- from building a brand new single...

  • 5 Beds
  • 2 Baths
  • 618514 MLS
1521 Rose St, Key West image
1521 Rose St, Key West $798,000

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...

  • 2 Beds
  • 1 Baths
  • 608965 MLS
1609 United St, Key West image
1609 United St, Key West $2,199,000

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...

  • 6 Beds
  • 5 Baths
  • 617882 MLS
1901 S Roosevelt Blvd Unit 401E, Key West image
1901 S Roosevelt Blvd Unit 401E, Key West $1,425,000 ▼

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...

  • 3 Beds
  • 2 Baths
  • 618248 MLS
2613 Gulfview Dr, Key West image
2613 Gulfview Dr, Key West $1,549,000

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 ...

  • 3 Beds
  • 3 Baths
  • 618065 MLS
1501 Georgia St, Key West image
1501 Georgia St, Key West $3,599,000 ▼

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...

  • 4 Beds
  • 5 Baths
  • 618829 MLS
2322-2324 Seidenberg Ave, Key West image
2322-2324 Seidenberg Ave, Key West $2,000,000 ▼

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...

  • 8 Beds
  • 4 Baths
  • 610098 MLS

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