35$2,800,000
2 bd · 2 ba · 809 sqft
1009 Whitehead Street, Key West, FL
Brenda J Donnelly · Brenda Donnelly Real Estate LLC
Homes with a Pool in Key West, FL
Hide MapHomes with a Pool in Key West, FL
24 of 145 Listings
35$2,800,000
2 bd · 2 ba · 809 sqft
1009 Whitehead Street, Key West, FL
Brenda J Donnelly · Brenda Donnelly Real Estate LLC
Price Reduced43$2,499,000
4 bd · 5 ba · 2,160 sqft
1316 Royal Street 6, Key West, FL
Sean Farrer, P.A. · Coldwell Banker Schmitt Real Estate Co. (KW)
44$3,800,000
3 bd · 3 ba · 1,933 sqft
619 Ashe Street, Key West, FL
Brenda J Donnelly · Brenda Donnelly Real Estate LLC
27$865,000
2 bd · 1 ba · 646 sqft
204 Southard Street 5, Key West, FL
Stacy Stahl · Realty ONE Group Destination
Price Reduced36$3,495,000
4 bd · 5 ba · 2,250 sqft
710 Caroline Street, Key West, FL
Jesse Friedman · Real Broker, LLC
39$1,799,765
3 bd · 3 ba · 1,502 sqft
1523 Seminary Street, Key West, FL
Christine Eck'Art · Berkshire Hathaway HomeServices Knight & Gardner Realty
26$868,000
2 bd · 2 ba · 798 sqft
3625 Seaside Drive 25410, Key West, FL
Richard Haskins · Buy The Keys
Price Reduced10$3,495,000
4 bd · 3 ba · 2,604 sqft
1017 Washington Street, Key West, FL
Ralph J Sanchez · Century 21 All Keys Inc (KW)
38$1,799,000
3 bd · 3 ba · 1,456 sqft
2101 Harris Avenue, Key West, FL
The Spottswood Team · Truman & Co. (KW)
50$1,300,000
3 bd · 2 ba · 784 sqft
611 Grinnell Street 4, Key West, FL
Dan Cloud · Water Vista Realty, Inc.
33$839,000
2 bd · 2 ba · 944 sqft
1124 Olivia Street 321, Key West, FL
Juan Alberto Benitez · Keller Williams Key West Compass Realty
Price Reduced48$1,239,000
2 bd · 4 ba · 1,824 sqft
25 Seaside South Court, Key West, FL
Louis M Paez · Coldwell Banker Schmitt Real Estate Co. (KW)
Price Reduced44$979,000
2 bd · 2 ba · 838 sqft
3808 Duck Avenue, Key West, FL
Elaine S Coyle · Keller Williams Key West Compass Realty
Price Reduced29$890,000
2 bd · 2 ba · 1,099 sqft
1901 S Roosevelt Boulevard 401S, Key West, FL
Vic Musmanno · Coldwell Banker Schmitt Real Estate Co. (KW)
37$2,499,000
3 bd · 4 ba · 2,502 sqft
1511 17th Terrace, Key West, FL
Kelli A Houze · Berkshire Hathaway HomeServices Knight & Gardner Realty
Price Reduced63$1,375,000
2 bd · 2 ba · 1,387 sqft
9 McCoy Circle 9, Key West, FL
Karen Verri · Ocean Sotheby's International Realty
60$2,500,000
8 bd · 4 ba · 1,504 sqft
1409 Whalton Street, Key West, FL
Felipe Carmona · Carmona Realty Group, LLC
55$1,245,000
3 bd · 3 ba · 1,600 sqft
243 Golf Club Drive, Key West, FL
Jessica M Prescott · Coastal Collection Real Estate Inc.
Price Reduced52$889,000
3 bd · 2 ba · 1,221 sqft
2601 S Roosevelt Boulevard Apt 103C, Key West, FL
Natallie M Liz · Island Welcome Real Estate LLC
Price Reduced67$6,200,000
5 bd · 5 ba · 5,378 sqft
3750 Sunrise Lane, Key West, FL
Terri Spottswood · Truman & Co. (KW)
Price Reduced27$839,900
3 bd · 2 ba · 1,320 sqft
34 Golf Club Drive, Key West, FL
Jaime M Caballero · Key West Vacation Properties & Realty, LLC (KW)
Price Reduced51$3,400,000
3 bd · 3 ba · 2,691 sqft
141 Simonton Street, Key West, FL
Brenda J Donnelly · Brenda Donnelly Real Estate LLC
34$1,025,000
2 bd · 2 ba · 1,311 sqft
1800 Atlantic Boulevard 427C, Key West, FL
Tommy Mack · Coastal Collection Real Estate Inc.
Price Reduced35$2,399,000
2 bd · 3 ba · 1,550 sqft
800 Fleming Street Unit C1, Key West, FL
Elizabeth E Chamberlain · Truman & Co. (KW)
Key West Association of REALTORSSource: HJN community data
September 2026 · This period is still settling
Selling at 94.9% of asking price
Buyers here are paying below asking. MLS · 30 sales · as of Sep 25, 2026