Mid Town Homes

/34
$5,195,000
- 5 Beds
- 6 Baths
- 3,597 Sq Ft
18 Hilton Haven Rd, Key West, FL 33040

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 unique private Key West Street with everything from a luxury resort and high-end properties to houseboats. This spectacular residence is a true gem facing both South and North. On the south side, enjoy sweeping decks, a waterfront

The Behmke Group Keller Williams Key West Compass Realty

18 Hilton Haven Rd, Key West, FL 33040
/3
$1,210,000 Sold Mar 24, 2025

1605 Catherine St, Key West, FL 33040
- 3 Beds
- 2 Baths
- 1,593 Sq Ft
- Built 1952
Last Sold Summary
- 2% Above List Price
- $760/SF
- 15 Days On Market
Current Estimated Value $1,250,200

Last Listing Agent Vic Musmanno Coldwell Banker Schmitt Real Estate Co. (KW)

1605 Catherine St, Key West, FL 33040

/20
Est $968,635 Not Listed For Sale

2601 S Roosevelt Blvd Unit 401, Key West, FL 33040
- 2 Beds
- 1 Bath
- 920 Sq Ft
- Built 1964
2601 S Roosevelt Blvd Unit 401, Key West, FL 33040

Last Sold Summary
- 9% Above List Price
- $1,152/SF
- 63 Days On Market
Last Sold Price $1,060,000

Last Listing Agent Moe Smyth Island Life Realty Experts

/20
$4,920,000
- 24 Beds
- 12 Baths
- 9,000 Sq Ft
1819 Atlantic Blvd, Key West, FL 33040

PRIME OPPORTUNITY! 1819 Atlantic Blvd, 1719/21 Josephine St, 1723/25 Josephine St, 1821 Atlantic Blvd & 1823 Atlantic Blvd. EMPLOYEE HOUSING, DEVELOPERS, CONDO CONVERSION! 3 FOURPLEXES 12 units offering 9,000 sq ft of Floor Living Area, and 2 vacant lots for a total of 23,340 sq ft of land. All 12 units are each a 2/1, for a total of 24 bedrooms and 12 baths. Buyer to verify with the governing

Jeffrey Dunaway Key West Realty, LLC (KW)

1819 Atlantic Blvd, Key West, FL 33040
/32
$995,000 Sold Aug 05, 2025

1621 Rose St Unit 2, Key West, FL 33040
- 3 Beds
- 3 Baths
- 1,439 Sq Ft
- Built 2008
Last Sold Summary
- 13% Below List Price
- $691/SF
- 131 Days On Market
Current Estimated Value $974,290

Last Listing Agent Mike Caron Keller Williams Key West Compass Realty

1621 Rose St Unit 2, Key West, FL 33040

/23
Est $600,567 Not Listed For Sale

2601 S Roosevelt Blvd Unit 208, Key West, FL 33040
- 1 Bed
- 1 Bath
- 754 Sq Ft
- Built 1967
2601 S Roosevelt Blvd Unit 208, Key West, FL 33040

Last Sold Summary
- 4% Above List Price
- $763/SF
- 164 Days On Market
Last Sold Price $575,000

Last Listing Agent Patricia McGrath Keller Williams Key West Compass Realty

/43
$2,495,000 Pending
- 4 Beds
- 6 Baths
- 3,118 Sq Ft
1616 Atlantic Blvd Unit 15, Key West, FL 33040

Welcome to Casa Caselles, where contemporary elegance and coastal serenity harmonize in this spacious breathtaking residence. Located in an exclusive gated enclave of just 19 town homes,this 4 bedroom, plus office, 5.5-bath masterpiece blends modern luxury with timeless charm and boasts an oceanfront pool to elevate your lifestyle.Spanning three levels of artfully designed space, this home

Elizabeth Chamberlain Truman & Co. (KW)

1616 Atlantic Blvd Unit 15, Key West, FL 33040
/25
$760,000 Sold Jun 26, 2025

2420 Patterson Ave Unit B, Key West, FL 33040
- 2 Beds
- 3 Baths
- 1,504 Sq Ft
- Built 2012
Last Sold Summary
- 9% Below List Price
- $505/SF
- 139 Days On Market
Current Estimated Value $788,295

Last Listing Agent Matthew Sheehan Ocean Sotheby's International Realty

2420 Patterson Ave Unit B, Key West, FL 33040

/2
Est $1,535,244 Not Listed For Sale

1609 Seminary St, Key West, FL 33040
- 4 Beds
- 3 Baths
- 1,513 Sq Ft
- Built 1953
1609 Seminary St, Key West, FL 33040

Last Sold Summary
- 5% Below List Price
- $1,071/SF
Last Sold Price $1,620,000

Last Listing Agent Sean Farrer Coldwell Banker Schmitt Real Estate Co. (KW)

/45
$1,170,000
- 3 Beds
- 2 Baths
- 1,221 Sq Ft
2601 S Roosevelt Blvd Unit 610B, Key West, FL 33040

Penthouse condo with panoramic views of Ocean, Beach, Gulf, Pools and beyond. Well maintained with cherry kitchen cabinets, granite counters, and newer appliances. All new AC, hurricane & soundproof windows, doors and sliders. Complex is lushly landscaped with 2 pools, 2 tennis courts and 8 acres of gorgeous plantings, Directly across the street from Smather;s Beach on the newly named ''Jimmy

Patricia McGrath Keller Williams Key West Compass Realty

2601 S Roosevelt Blvd Unit 610B, Key West, FL 33040
/10
$3,000,000 Sold Nov 03, 2025

1716 Bertha St, Key West, FL 33040
- 16 Beds
- 8 Baths
- 6,000 Sq Ft
- Built 1969
Last Sold Summary
- 14% Below List Price
- $500/SF
- 279 Days On Market
Current Estimated Value $2,645,419

Last Listing Agent Jeffrey Dunaway Key West Realty, LLC (KW)

1716 Bertha St, Key West, FL 33040

/38
Est $985,653 Not Listed For Sale

32 Hilton Haven Rd Unit 2, Key West, FL 33040
- 2 Beds
- 2 Baths
- 888 Sq Ft
- Built 2002
32 Hilton Haven Rd Unit 2, Key West, FL 33040

Last Sold Summary
- 10% Above List Price
- $1,239/SF
- 11 Days On Market
Last Sold Price $1,100,000

Last Listing Agent Dan Serban Key West Luxury Real Estate Inc (KW)

/28
$549,000
- 1 Bed
- 1 Bath
- 754 Sq Ft
2601 S Roosevelt Blvd Unit 608, Key West, FL 33040

Only steps away from our island's largest and most serene sandy beach, this top-floor unit offers an unbeatable location for swimming, snorkeling, bicycling and beach walks. Enjoy stunning ocean and pool views from your private balcony and soak in that coveted west-facing Key West sunset every day. The bright and airy open floor plan is move-in ready, featuring impact windows and doors, along

Sean Farrer Coldwell Banker Schmitt Real Estate Co. (KW)

2601 S Roosevelt Blvd Unit 608, Key West, FL 33040
/22
$610,000 Sold Nov 03, 2025

2500 Harris Ave, Key West, FL 33040
- 2 Beds
- 1 Bath
- 810 Sq Ft
- Built 1948
Last Sold Summary
- 3% Below List Price
- $753/SF
- 6 Days On Market
Current Estimated Value $601,274

Last Listing Agent Francesca Santiago Keller Williams Realty Professionals (KW)

2500 Harris Ave, Key West, FL 33040

/29
Est $1,407,483 Not Listed For Sale

1500 Atlantic Blvd Unit 213, Key West, FL 33040
- 2 Beds
- 2 Baths
- 1,531 Sq Ft
- Built 1986
1500 Atlantic Blvd Unit 213, Key West, FL 33040

Last Sold Summary
- 1% Above List Price
- $914/SF
- 346 Days On Market
Last Sold Price $1,400,000

Last Listing Agent Team Kaufelt Truman & Co. (KW)

/45
$3,999,000 Open Sun 12PM - 3PM
- 4 Beds
- 6 Baths
- 3,400 Sq Ft
1314 Johnson St, Key West, FL 33040

The wait for perfection has concluded at 1314 Johnson Street. Brand new and never lived in, this pristine masterpiece is where architectural integrity meets the effortless spirit of the Key West lifestyle. Situated just two blocks from the iconic Casa Marina Resort and the beautiful sands of Higgs Beach, this residence offers a rare combination of 3,400 square feet of sophisticated interior

Brenda Donnelly Brenda Donnelly Real Estate LLC

1314 Johnson St, Key West, FL 33040
/3
$750,000 Sold Dec 12, 2025

2111 Flagler Ave, Key West, FL 33040
- 3 Beds
- 3 Baths
- 1,514 Sq Ft
- Built 1958
Last Sold Summary
- 6% Below List Price
- $495/SF
- 23 Days On Market
Current Estimated Value $750,612

Last Listing Agent The Behmke Group Keller Williams Key West Compass Realty

2111 Flagler Ave, Key West, FL 33040

/40
Est $702,873 Not Listed For Sale

2601 S Roosevelt Blvd Unit 117, Key West, FL 33040
- 3 Beds
- 2 Baths
- 1,221 Sq Ft
- Built 1967
2601 S Roosevelt Blvd Unit 117, Key West, FL 33040

Last Sold Summary
- 4% Above List Price
- $553/SF
- 277 Days On Market
Last Sold Price $675,000

Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

/46
$1,495,000
- 3 Beds
- 2 Baths
- 1,559 Sq Ft
1720 Patricia St, Key West, FL 33040

Perfect Home in the Heart of Key West - Renovated with Pool Near BeachIdeally located in the heart of Key West, this recently renovated three-bedroom, two-bath home is just a short stroll to Higgs Beach, White Street Pier, nearby parks, and popular tennis and bocce courts. It's a fantastic opportunity to own a move-in ready home in one of Key West's most desirable neighborhoods.Inside, the

Richard Haskins Buy The Keys

1720 Patricia St, Key West, FL 33040
/27
$625,000 Sold Jul 25, 2025

1702 Bertha St, Key West, FL 33040
- 3 Beds
- 1 Bath
- 990 Sq Ft
- Built 1963
Last Sold Summary
- 7% Below List Price
- $631/SF
- 62 Days On Market
Current Estimated Value $641,298

Last Listing Agent Jimmy Lane Island Life Realty Experts

1702 Bertha St, Key West, FL 33040

/29
Est $898,504 Not Listed For Sale

2601 S Roosevelt Blvd Unit 602, Key West, FL 33040
- 2 Beds
- 2 Baths
- 980 Sq Ft
- Built 1967
2601 S Roosevelt Blvd Unit 602, Key West, FL 33040

Last Sold Summary
- 10% Above List Price
- $832/SF
- 360 Days On Market
Last Sold Price $815,000

Last Listing Agent Patricia McGrath Keller Williams Key West Compass Realty

/31
$3,495,000 Under Contract
- 4 Beds
- 5 Baths
- 2,628 Sq Ft
1610 South St, Key West, FL 33040

This British designer has spent over twenty years crafting contemporary properties in a luxurious Caribbean setting. Well-known for attention to detail and a commitment to sourcing the finest materials, this builder's constructions are exceptional. The spacious living room effortlessly merges with the outdoors upon opening the storm-proof sliding doors, creating a seamless transition between

Rob Severin Rob Severin Real Estate Co

1610 South St, Key West, FL 33040
/51
$1,200,000 Sold Aug 14, 2025

1501 Rose St, Key West, FL 33040
- 2 Beds
- 2 Baths
- 1,433 Sq Ft
- Built 1953
Last Sold Summary
- 11% Below List Price
- $837/SF
- 92 Days On Market
Current Estimated Value $1,185,035

Last Listing Agent Jimmy Lane Island Life Realty Experts

1501 Rose St, Key West, FL 33040

/31
Est $920,215 Not Listed For Sale

1901 S Roosevelt Blvd Unit 308S, Key West, FL 33040
- 2 Beds
- 2 Baths
- 1,099 Sq Ft
- Built 1995
1901 S Roosevelt Blvd Unit 308S, Key West, FL 33040

Last Sold Summary
- 9% Below List Price
- $919/SF
- 38 Days On Market
Last Sold Price $1,010,000

Last Listing Agent Vic Musmanno Coldwell Banker Schmitt Real Estate Co. (KW)

/41
$989,000
- 2 Beds
- 2 Baths
- 1,118 Sq Ft
1606 Flagler Ave, Key West, FL 33040

Modern Coastal Living Near Key West Beaches - Renovated 2BD/2BA, Impact Windows, Private Outdoor Oasis & Off-Street ParkingBeautifully renovated single-story 2BD/2BA home in Midtown Key West, just minutes to the beach and Edward B. Knight Pier. Features include an open-concept living area, updated kitchen with stainless appliances, beverage bar, and mobile island. The primary suite offers two

Dustan Carpenter Berkshire Hathaway HomeServices Knight & Gardner Realty

1606 Flagler Ave, Key West, FL 33040
/28
$3,280,000 Sold Mar 20, 2025

719 Eisenhower Dr Unit 7, Key West, FL 33040
- 5 Beds
- 4 Baths
- 3,417 Sq Ft
- Built 2008
Last Sold Summary
- 22% Below List Price
- $960/SF
- 136 Days On Market
Current Estimated Value $3,223,443

Last Listing Agent Claude Gardner Berkshire Hathaway HomeServices Knight & Gardner Realty

719 Eisenhower Dr Unit 7, Key West, FL 33040

/15
Est $1,106,424 Not Listed For Sale

1901 S Roosevelt Blvd Unit 103S, Key West, FL 33040
- 2 Beds
- 2 Baths
- 1,099 Sq Ft
- Built 1995
1901 S Roosevelt Blvd Unit 103S, Key West, FL 33040

Last Sold Summary
- 8% Below List Price
- $1,092/SF
- 3 Days On Market
Last Sold Price $1,200,000

Last Listing Agent Joanne Tarantino Berkshire Hathaway HomeServices Knight & Gardner Realty

/53
$2,100,000
- 8 Beds
- 4 Baths
- 750 Sq Ft
2322 Seidenberg Ave, Key West, FL 33040

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 ) individual, 750 sq ft licensed units, with (4) separate legal descriptions, parcel numbers, insurance policies, & utilities meters. At one time, there were four individual loans on each of the units as well.**** The only

Raymond Capas Berkshire Hathaway HomeServices Knight & Gardner Realty

2322 Seidenberg Ave, Key West, FL 33040
/44
$2,400,000 Sold Apr 03, 2025

1500 Johnson St, Key West, FL 33040
- 4 Beds
- 4 Baths
- 1,884 Sq Ft
- Built 1954
Last Sold Summary
- 4% Below List Price
- $1,274/SF
- 53 Days On Market
Current Estimated Value $2,448,745

Last Listing Agent Tammy Stiles Berkshire Hathaway HomeServices Knight & Gardner Realty

1500 Johnson St, Key West, FL 33040

/2
Est $794,608 Not Listed For Sale

1901 S Roosevelt Blvd Unit 106W, Key West, FL 33040
- 2 Beds
- 2 Baths
- 1,099 Sq Ft
- Built 1996
1901 S Roosevelt Blvd Unit 106W, Key West, FL 33040

Last Sold Summary
- 3% Below List Price
- $746/SF
Last Sold Price $820,000

Last Listing Agent Dawn McComish Lokation Real Estate

/45
$955,000
- 3 Beds
- 2 Baths
- 1,515 Sq Ft
2012 Roosevelt Dr, Key West, FL 33040

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 with center island, ample cabinetry, and stainless appliances, flowing seamlessly into a bright family room. A separate living room and dedicated office provide additional space for work, relaxation, or entertaining.The first

Jaime Caballero Key West Vacation Properties & Realty, LLC (KW)

2012 Roosevelt Dr, Key West, FL 33040
/27
$1,875,000 Sold Nov 06, 2025

1311 Atlantic Dr, Key West, FL 33040
- 3 Beds
- 3 Baths
- 1,672 Sq Ft
- Built 2014
Last Sold Summary
- 4% Below List Price
- $1,121/SF
- 108 Days On Market
Current Estimated Value $1,834,725

Last Listing Agent Elizabeth Chamberlain Truman & Co. (KW)

1311 Atlantic Dr, Key West, FL 33040

/2
Est $764,276 Not Listed For Sale

1901 S Roosevelt Blvd Unit 404, Key West, FL 33040
- 2 Beds
- 2 Baths
- 1,186 Sq Ft
- Built 1984
1901 S Roosevelt Blvd Unit 404, Key West, FL 33040

Last Sold Summary
- 19% Below List Price
- $793/SF
Last Sold Price $940,000

Last Listing Agent Vic Musmanno Coldwell Banker Schmitt Real Estate Co. (KW)

/25
$1,449,000
- 4 Beds
- 3 Baths
- 1,767 Sq Ft
1527 von Phister St, Key West, FL 33040

Centrally located in the heart of Key West, this beautifully restored traditional Conch-style home offers two legal units and exceptional versatility.The first-floor residence features two bedrooms and two bathrooms, a charming covered front porch, and thoughtfully updated interiors that maintain authentic island character. Upstairs, a bright and airy two-bedroom, one-bath home enjoys its own

Key West Luxury Finders Preferred Properties (KW)

1527 von Phister St, Key West, FL 33040
/30
$2,800,000 Sold Jan 29, 2026

1400 1st St, Key West, FL 33040
- 5 Beds
- 4 Baths
- 3,255 Sq Ft
- Built 2006
Last Sold Summary
- 6% Below List Price
- $860/SF
- 9 Days On Market
Current Estimated Value $2,964,139

Last Listing Agent Brenda Donnelly Brenda Donnelly Real Estate LLC

1400 1st St, Key West, FL 33040

/17
Est $995,117 Not Listed For Sale

1901 S Roosevelt Blvd Unit 402, Key West, FL 33040
- 2 Beds
- 2 Baths
- 1,099 Sq Ft
- Built 1995
1901 S Roosevelt Blvd Unit 402, Key West, FL 33040

Last Sold Summary
- 5% Below List Price
- $951/SF
- 4 Days On Market
Last Sold Price $1,045,000

Last Listing Agent Joanne Tarantino Berkshire Hathaway HomeServices Knight & Gardner Realty

/36
$2,365,000
- 4 Beds
- 3 Baths
- 2,000 Sq Ft
1716 Laird St, Key West, FL 33040

This brand new home is a beauty! Completed in 2025, this 2 story , Cat 5 home, with Impact windows and doors, Hardiboard siding , has 4 Bedrooms, 3 bathrooms, a large spacious Living/ Dining/ Kitchen occupying the majority of the First level, with a downstairs bedroom and bath. The second floor has 3 bedrooms and 2 baths. The outside - back yard is incredible, with about a 30 foot long chickee

Elaine Coyle Keller Williams Key West Compass Realty

1716 Laird St, Key West, FL 33040
/35
$1,000,000 Sold May 02, 2025

1709 Josephine St, Key West, FL 33040
- 2 Beds
- 2 Baths
- 1,189 Sq Ft
- Built 1969
Last Sold Summary
- 13% Below List Price
- $841/SF
- 7 Days On Market
Current Estimated Value $1,013,918

Last Listing Agent Andrea Otava Last Key Realty, Inc (KW)

1709 Josephine St, Key West, FL 33040

/36
Est $1,221,654 Not Listed For Sale

1901 S Roosevelt Blvd Unit 304, Key West, FL 33040
- 2 Beds
- 2 Baths
- 1,186 Sq Ft
- Built 1984
1901 S Roosevelt Blvd Unit 304, Key West, FL 33040

Last Sold Summary
- 13% Below List Price
- $1,180/SF
- 6 Days On Market
Last Sold Price $1,400,000

Last Listing Agent Joanne Tarantino Berkshire Hathaway HomeServices Knight & Gardner Realty

/41
$2,550,000 Under Contract
- 3 Beds
- 3 Baths
- 1,818 Sq Ft
1231 Washington St, Key West, FL 33040

Prime Mid-Town location - walk or bike to White Street pier, Tennis and Pickle ball, and Higgs Beach. Spanning over 1800 square feet, This home is easy one level living, completely fenced, has multiple off street parking spaces- covered and uncovered, and a remote control entrance gate for parking. The Main home has 2 bedrooms, 2 full bathrooms,, an additional private jetted tub area and an

Elaine Coyle Keller Williams Key West Compass Realty

1231 Washington St, Key West, FL 33040

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