Mid Town Homes

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  $250,000

  • Land
  • 0.02 Acre
  • $12,500,000 per Acre

  1801 N Roosevelt Blvd, Key West, FL 33040

  LIVE IN PARADISE AFFORDABLE LIVEABOARD Houseboat & Slip (Package) at Garrison Bight Marina (Houseboat Row). It's a Leasehold to the City of Key West and with the Transfer of Title to your name. NO RENTALS, VRBO/AIRBNB! This community is Historic. It's a TRUE KEY WEST LIFESTYLE... CASH ONLY! If your ready to enjoy life and have a crash pad in the Florida Keys, then come and see this one.

  

  Annie Rivera

  Berkshire Hathaway Florida Realty

  (645) 225-2030

  1801 N Roosevelt Blvd, Key West, FL 33040
• Explore Mid Town

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  /18

  $4,400 per month

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft
  • Property for Rent

  1916 Staples Ave, Key West, FL 33040

  ANNUAL RENTAL! Available April 1st. The perfect Key West classic cottage with all the modern features! Perfectly located just short bike ride to Old Town or distance to the island's major shopping centers. Gated entry and fenced in. Large storage area in backyard, Gas BBQ grill for cookouts and sundeck. Has Washer/dryer in rear utility room. Nicely appointed interior fully furnished with a

  

  Christian Loffreno

  Loffreno Real Estate

  (786) 244-6868

  1916 Staples Ave, Key West, FL 33040
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  /10

  $560,000 Sold Dec 26, 2025

  2433 Linda Ave, Key West, FL 33040

  • 3 Beds
  • 2 Baths
  • 2,099 Sq Ft
  • Built 1953

  Last Sold Summary

  • 7% Below List Price
  • $267/SF
  • 96 Days On Market

  Last Listing Agent Walt Lee Berkshire Hathaway HomeServices Knight & Gardner Realty

  2433 Linda Ave, Key West, FL 33040
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  /17

  Est $995,117 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,099 Sq Ft

  1901 S Roosevelt Blvd Unit 402, Key West, FL 33040

  1901 S Roosevelt Blvd Unit 402, Key West, FL 33040
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  $3,695,000 Open House 3/14

  • 5 Beds
  • 6 Baths
  • 2,033 Sq Ft

  1230 South St, Key West, FL 33040

  1230 South Street stands as one of the most exquisite historic renovations ever completed in Key West where architectural heritage, artisanal craftsmanship, and refined island living converge in one of the city's most coveted neighborhoods.This five-bedroom, five-and-a-half-bath estate is a celebration of authenticity and modern luxury. Every detail, from the extensive use of original Dade County

  

  Damian Vantriglia

  Berkshire Hathaway HomeServices Knight & Gardner Realty

  (786) 840-2961

  1230 South St, Key West, FL 33040
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  /14

  $4,000 per month

  • 2 Beds
  • 1 Bath
  • 612 Sq Ft
  • Condo for Rent

  2513 Staples Ave Unit B, Key West, FL 33040

  Property Id: 1836419This is the rear unit in a super cute ground level duplex in midtown. 2 bed/1 bath. One off-street parking spot. Shared yard. In unit laundry. Updated appliances. Clean and easy to maintain. Utilities and exterior maintenance included. Great for roommates or small families. Current renters are active military and are being redeployed elsewhere.

  2513 Staples Ave Unit B, Key West, FL 33040
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  /25

  $685,000 Sold Jun 10, 2025

  2601 S Roosevelt Blvd Unit 603 A, Key West, FL 33040

  • 1 Bed
  • 1 Bath
  • 754 Sq Ft
  • Built 1967

  Last Sold Summary

  • 10% Below List Price
  • $908/SF
  • 25 Days On Market

  Current Estimated Value $701,952

  Last Listing Agent Tom Mclaughlin Coldwell Banker Schmitt Real Estate Co. (KW)

  2601 S Roosevelt Blvd Unit 603 A, Key West, FL 33040
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  /12

  Est $764,050 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,180 Sq Ft

  2508 Patterson Ave, Key West, FL 33040

  2508 Patterson Ave, Key West, FL 33040
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  /40

  $1,575,000

  • 3 Beds
  • 2 Baths
  • 1,395 Sq Ft

  1901 S Roosevelt Blvd Unit 401, Key West, FL 33040

  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 from world-famous Smathers Beach, this spacious 3-bedroom, 2-bath condo blends coastal luxury with unbeatable island convenience.Inside, expansive living spaces open to large windows and glass doors showcasing ocean views and

  

  Emily Lombard

  Ocean Sotheby's International Realty

  (786) 952-5592

  1901 S Roosevelt Blvd Unit 401, Key West, FL 33040
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  /26

  $4,900 per month

  • 3 Beds
  • 2 Baths
  • 912 Sq Ft
  • Property for Rent

  2401 Patterson Ave Unit 101, Key West, FL 33040

  Spacious 3BD/2BA - Renovated First-Floor Duplex in MidtownThis fully renovated 3-bedroom, 2-bath apartment offers everything you need for comfortable long-term living in Key West's Midtown neighborhood. Located on the first floor of a freshly updated duplex, this home features a large open-concept living area and kitchen with all new appliances and high-end finishes. The unit includes a brand-new

  Jody Clark Key West Luxury Real Estate Inc (KW)

  2401 Patterson Ave Unit 101, Key West, FL 33040
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  /36

  $665,000 Sold Apr 07, 2025

  2027 Staples Ave, Key West, FL 33040

  • 2 Beds
  • 1 Bath
  • 784 Sq Ft
  • Built 1958

  Last Sold Summary

  • $848/SF
  • 0 Days On Market

  Current Estimated Value $829,951

  Last Listing Agent Jessica Forsythe eXp Realty LLC

  2027 Staples Ave, Key West, FL 33040
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  /37

  Est $2,260,124 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,581 Sq Ft

  1701 Laird St, Key West, FL 33040

  1701 Laird St, Key West, FL 33040
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  /43

  $1,424,999

  • 3 Beds
  • 2 Baths
  • 1,378 Sq Ft

  1712 Laird St, Key West, FL 33040

  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 Beach, Higgs Beach Park, the Key West Nature Preserve, White Street Pier, and the island's beloved Garden Club and dog park, this home places the best of the island lifestyle quite literally at your doorstep. Duval Street and the

  

  Matthew Sheehan

  Ocean Sotheby's International Realty

  (305) 902-5415

  1712 Laird St, Key West, FL 33040
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  /20

  $17,386 per month

  • 3 Beds
  • 2 Baths
  • Condo for Rent

  2623 Flagler Ave Unit ID1307035P, Key West, FL 33040

  The advertised rate of $17,387/month is the lowest available price, based on a 1 month(s) stay with a move-in date of June 7, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

  2623 Flagler Ave Unit ID1307035P, Key West, FL 33040
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  $1,675,000 Sold Jul 30, 2025

  2605 Gulfview Dr, Key West, FL 33040

  • 3 Beds
  • 3 Baths
  • 1,320 Sq Ft
  • Built 1999

  Last Sold Summary

  • 7% Below List Price
  • $1,269/SF
  • 116 Days On Market

  Current Estimated Value $1,722,600

  Last Listing Agent Paige Bethel Island Home Realty Inc.

  2605 Gulfview Dr, Key West, FL 33040
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  /7

  Est $732,704 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 980 Sq Ft

  2601 S 2601 Roosevelt Blvd Unit 302A, Key West, FL 33040

  2601 S 2601 Roosevelt Blvd Unit 302A, Key West, FL 33040
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  $1,700,000

  • 2 Beds
  • 2 Baths
  • 1,311 Sq Ft

  1800 Atlantic Blvd Unit 327C, Key West, FL 33040

  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 completely remodeled, stylish 2-bedroom, 2-bathroom condo encompassing approximately 1,311 sq ft of luxurious living space. Transient license and established management make this a rare turnkey investment opportunity offering both a

  

  Tommy Mack

  Coastal Collection Real Estate Inc.

  (786) 744-6462

  1800 Atlantic Blvd Unit 327C, Key West, FL 33040
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  $13,000 per month

  • 4 Beds
  • 4 Baths
  • Property for Rent

  2214 Seidenberg Ave, Key West, FL 33040

  Welcome to your luxurious oasis in Key West, where modern comfort meets tropical paradise. This stunning new construction home features four spacious bedrooms, each with an en suite bathroom. Lushly landscaped grounds, this 5,700 square foot property offers plenty of room to unwind and enjoy the beauty of the island.Imagine starting your day with a refreshing swim in the large, private, heated

  Paige Bethel Island Home Realty Inc.

  2214 Seidenberg Ave, Key West, FL 33040
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  $812,000 Sold May 12, 2025

  2021 Harris Ave, Key West, FL 33040

  • 3 Beds
  • 1 Bath
  • 1,028 Sq Ft
  • Built 1958

  Last Sold Summary

  • 2% Above List Price
  • $790/SF
  • 16 Days On Market

  Current Estimated Value $829,181

  Last Listing Agent Jimmy Lane Island Life Realty Experts

  2021 Harris Ave, Key West, FL 33040
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  /22

  Est $964,624 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 980 Sq Ft

  2601 S 2601 Roosevelt Blvd Unit 401B, Key West, FL 33040

  2601 S 2601 Roosevelt Blvd Unit 401B, Key West, FL 33040
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  $2,250,000

  • 3 Beds
  • 3 Baths
  • 1,690 Sq Ft

  1503 Johnson St, Key West, FL 33040

  Welcome to 1503 Johnson St, a luxurious Key West retreat now offered for sale--a turnkey residence that truly embodies style, comfort, and effortless island living. This elegant three-bedroom, three-bathroom furnished home is situated on a fully fenced corner lot, offering exceptional privacy while keeping you close to everything the island has to offer. Located just four blocks from the Atlantic

  

  Leslie Howard

  Coldwell Banker Schmitt Real Estate Co. (KW)

  (877) 692-1660

  1503 Johnson St, Key West, FL 33040
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  $7,000 per month

  • 4 Beds
  • 2 Baths
  • 1,900 Sq Ft
  • House for Rent

  1330 3rd St, Key West, FL 33040

  Property Id: 2292938Move-in ready Key West living! Close to shopping, schools, beaches and Old Town.Property Highlights•Spacious 4 bedrooms / 2 bathrooms•~1,900 sq ft•Fenced yard with covered porch•Pet-friendly with deposit•Annual lease - $7,000 per month•Utilities not included•Credit/Background Check This home combines comfort, space, and

  1330 3rd St, Key West, FL 33040
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  $899,000 Sold Aug 15, 2025

  2212 Fogarty Ave, Key West, FL 33040

  • 4 Beds
  • 3 Baths
  • 1,826 Sq Ft
  • Built 1954

  Last Sold Summary

  • $492/SF
  • 5 Days On Market

  Current Estimated Value $934,220

  Last Listing Agent Bobby Baker Brightwild Real Estate

  2212 Fogarty Ave, Key West, FL 33040
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  /16

  Est $729,027 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 980 Sq Ft

  2601 S 2601 Roosevelt Blvd Unit 506A, Key West, FL 33040

  2601 S 2601 Roosevelt Blvd Unit 506A, Key West, FL 33040
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  $1,395,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,668 Sq Ft

  1719 Atlantic Blvd, Key West, FL 33040

  Location, Location, Location. Just a stones throw away from the Atlantic Ocean. Gorgeous 3BR/2B with bonus room/home office. Updated open floor plan with stunning kitchen and baths. NEW landscaping & turf, HVAC (2025) flooring, paint, Tesla charger & fans. Parking for 2 private driveway and tons of street parking. Property sits behind a privacy wall and encompasses an entire block with a heated

  

  Michelle Howerton

  Brenda Donnelly Real Estate LLC

  (786) 755-1893

  1719 Atlantic Blvd, Key West, FL 33040
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  /20

  $4,732 per month

  • 3 Beds
  • 2 Baths
  • 1,399 Sq Ft
  • Condo for Rent

  2026 Seidenberg Ave Unit ID1297830P, Key West, FL 33040

  The advertised rate of $4,732/month is the lowest available price, based on a 1 month(s) stay with a move-in date of June 3, 2027.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

  2026 Seidenberg Ave Unit ID1297830P, Key West, FL 33040
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  $925,000 Sold Mar 06, 2025

  1711 von Phister St, Key West, FL 33040

  • 3 Beds
  • 2 Baths
  • 1,170 Sq Ft
  • Built 1943

  Last Sold Summary

  • 12% Below List Price
  • $791/SF
  • 141 Days On Market

  Current Estimated Value $973,416

  Last Listing Agent Bascom Grooms Bascom Grooms Real Estate (KW)

  1711 von Phister St, Key West, FL 33040
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  /24

  Est $806,709 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,221 Sq Ft

  2601 S 2601 Roosevelt Blvd Unit 221C, Key West, FL 33040

  2601 S 2601 Roosevelt Blvd Unit 221C, Key West, FL 33040
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  /36

  $949,000

  • 4 Beds
  • 3 Baths
  • 1,400 Sq Ft

  2524 Patterson Ave, Key West, FL 33040

  Discover the charm and practicality of 2524 Patterson Dr., a delightful Conch-style Key West pool home tucked away in sought-after Mid Town. Set on a generous 5,000 sq ft corner lot with lush mature trees, this home offers rare outdoor privacy, highlighted by a sparkling private pool and fully fenced backyard oasis. Large glass doors in the living room and primary suite invite in natural light

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 783-4986

  2524 Patterson Ave, Key West, FL 33040
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  /28

  $4,700 per month

  • 2 Beds
  • 1.5 Baths
  • 850 Sq Ft
  • House for Rent

  2005 Fogarty Ave, Key West, FL 33040

  PRICE REDUCED! This Quintessential “Keysie” home is truly something special. Situated in a quiet, family friendly, local neighborhood, this Cozy 2 bedroom, 1 bath “plus”, includes an additional private outdoor shower in a tropical setting! FULLY furnished/turn key with all living essentials, complete renovation in Spring 2025. Includes laundry room as well as large tranquil backyard with lush

  2005 Fogarty Ave, Key West, FL 33040
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  $1,340,000 Sold Jul 09, 2025

  1911 Fogarty Ave, Key West, FL 33040

  • 2 Beds
  • 2 Baths
  • 1,195 Sq Ft
  • Built 1953

  Last Sold Summary

  • 8% Below List Price
  • $1,121/SF
  • 14 Days On Market

  Current Estimated Value $1,334,257

  Last Listing Agent Brenda Donnelly Brenda Donnelly Real Estate LLC

  1911 Fogarty Ave, Key West, FL 33040
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  /25

  Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,268 Sq Ft

  1220 Seminary St, Key West, FL 33040

  1220 Seminary St, Key West, FL 33040
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  /61

  $1,499,000

  • 7 Beds
  • 4 Baths
  • 2,699 Sq Ft

  1614 Dennis St, Key West, FL 33040

  1614 Dennis St is a rare income-producing triplex offering strong cash flow and flexible use in the heart of Key West. Generating over $125,000 annually in rental income, this well-configured property features three separate units, each with its own washer and dryer, making it highly desirable for long-term tenants and employee housing.The layout includes two spacious 2-bedroom / 1-bath units and

  

  Matthew Sheehan

  Ocean Sotheby's International Realty

  (855) 916-7690

  1614 Dennis St, Key West, FL 33040
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  /10

  $4,500 per month

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • House for Rent

  14 Hilton Haven Rd, Key West, FL 33040

  Quiet street, completely furnished two bedroom one bath available May 1st.Located in New Town, near Key West Yacht ClubCan be rented for 1 year or 9 months

  14 Hilton Haven Rd, Key West, FL 33040
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  $2,450,000 Sold Feb 03, 2026

  1526 Washington St, Key West, FL 33040

  • 3 Beds
  • 3 Baths
  • 2,042 Sq Ft
  • Built 1953

  Last Sold Summary

  • $1,200/SF
  • 1 Day On Market

  Last Listing Agent Dustan Carpenter Berkshire Hathaway HomeServices Knight & Gardner Realty

  1526 Washington St, Key West, FL 33040
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  /24

  Est $832,342 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,594 Sq Ft

  2421 Fogarty Ave Unit 1 &2, Key West, FL 33040

  2421 Fogarty Ave Unit 1 &2, Key West, FL 33040
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  /46

  $1,395,000

  • 4 Beds
  • 3 Baths
  • 1,578 Sq Ft

  2105 Fogarty Ave, Key West, FL 33040

  Discover the charm of 2105 Fogarty Ave--an inviting Key West gem that blends character, comfort, and an ideal island lifestyle. From the moment you step inside, you'll find bright, welcoming spaces filled with personality and warmth. Each room offers thoughtful details and natural light, creating an atmosphere that feels instantly like home.Enjoy the lush, sun-filled garden--a private outdoor

  

  Darrin Smith

  Key West Luxury Real Estate Inc (KW)

  (786) 432-5835

  2105 Fogarty Ave, Key West, FL 33040
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  /10

  $2,800 per month

  • 2 Beds
  • 1 Bath
  • 710 Sq Ft
  • Condo for Rent

  1220 3rd St Unit UP, Key West, FL 33040

  Discover your perfect living space in the heart of new-town Key West. This charming 2-bedroom, 1-bathroom apartment in a quaint 4-plex offers both comfort and convenience. Situated on the upper level, this unit boasts a brand-new deck, perfect for enjoying warm island breezes and outdoor relaxation.Step inside to a spacious living room adorned with high ceilings that create an open and

  1220 3rd St Unit UP, Key West, FL 33040
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  $975,000 Sold Jul 30, 2025

  2418 Linda Ave, Key West, FL 33040

  • 3 Beds
  • 2 Baths
  • 1,613 Sq Ft
  • Built 1953

  Last Sold Summary

  • 19% Below List Price
  • $604/SF
  • 85 Days On Market

  Current Estimated Value $997,625

  Last Listing Agent Tonya Cabanas Truman & Co. (KW)

  2418 Linda Ave, Key West, FL 33040
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  /28

  Est $1,329,498 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,339 Sq Ft

  1800 Atlantic Blvd Unit 420C, Key West, FL 33040

  1800 Atlantic Blvd Unit 420C, Key West, FL 33040

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