Realty.com
Buy

Start here

  • Homes for sale by state
  • Home buying tips
  • Before you start looking
  • The buying timeline

Afford it

  • Today's mortgage rates
  • Mortgage calculator
  • How much can I afford?
  • Get pre-approved

Make the deal

  • Writing a winning offer
  • Inspections & appraisals
  • Closing costs, itemized
  • Find a buyer's agent
Sell

Selling Options

  • What's my home worth?
  • Compare selling options
  • Get an instant cash offer
  • Buy before you sell

Resources

  • How selling works
  • When should I sell?
  • Home selling tips
  • Pricing your home
  • What's worth fixing first
  • Find a seller's agent
Home Loans
Find an Agent
Save searchAdvertiseSign In
Saved homesSaved searchesYour toursYour inquiriesRecently viewedAccount settings

Registered offenders on the map

Save search

Registered offenders on the map

Safety & registry resources

Review official public-safety information for any area from these government sources:

  • U.S. Dept. of Justice National Sex Offender Public Website (NSOPW)
  • FBI: state sex-offender registry directory
Realty.com
Buy

Start here

  • Homes for sale by state
  • Home buying tips
  • Before you start looking
  • The buying timeline

Afford it

  • Today's mortgage rates
  • Mortgage calculator
  • How much can I afford?
  • Get pre-approved

Make the deal

  • Writing a winning offer
  • Inspections & appraisals
  • Closing costs, itemized
  • Find a buyer's agent
Save searchAdvertiseSign In
Saved homesSaved searchesYour toursYour inquiriesRecently viewedAccount settings
  • Rentals
  • Commercial

Registered offenders on the map

Sell

Selling Options

  • What's my home worth?
  • Compare selling options
  • Get an instant cash offer
  • Buy before you sell

Resources

  • How selling works
  • When should I sell?
  • Home selling tips
  • Pricing your home
  • What's worth fixing first
  • Find a seller's agent
Home Loans
Find an Agent
Save search
Homes with a Pool in Key West, FL — Page 5
145 listings

Homes with a Pool in Key West, FL

Homes with a Pool in Key West, FL

Hide Map
24 of 145 Listings
Map

Homes with a Pool in Key West, FL

24 of 145 Listings

  1. 1620 Jamaica Drive — photoPrice Reduced

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas
30
Active

$1,975,000

4 bd · 3 ba · 2,080 sqft

1620 Jamaica Drive, Key West, FL

Bascom L Grooms · Bascom Grooms Real Estate (KW)

  • 3312 Northside Drive 202 — photoPrice Reduced22Active

    $429,900

    2 bd · 2 ba · 792 sqft

    3312 Northside Drive 202, Key West, FL

    Danica Watkins · Keller Williams Key West Compass Realty

  • 1401 Simonton Street #11 — photo17Active

    $1,250,000

    2 bd · 2 ba · 958 sqft

    1401 Simonton Street #11, Key West, FL

    Ralph J Sanchez · Century 21 All Keys Inc (KW)

  • 1613 Trinidad Drive — photo38Active

    $1,285,000

    3 bd · 2 ba · 1,380 sqft

    1613 Trinidad Drive, Key West, FL

    Shirley Carey · Berkshire Hathaway HomeServices Knight & Gardner Realty

  • 2924 Riviera Drive — photo56Active

    $2,549,000

    3 bd · 4 ba · 2,469 sqft

    2924 Riviera Drive, Key West, FL

    Walt Lee · Berkshire Hathaway HomeServices Knight & Gardner Realty

  • 401 Emma Street Apt H — photo54Active

    $2,999,500

    2 bd · 2 ba · 1,770 sqft

    401 Emma Street Apt H, Key West, FL

    Ralph J Sanchez · Century 21 All Keys Inc (KW)

  • 3314 Northside Drive 13 & 13a — photo9Active

    $675,000

    3 bd · 3 ba · 1,358 sqft

    3314 Northside Drive 13 & 13a, Key West, FL

    Will Langley · Berkshire Hathaway HomeServices Knight & Gardner Realty

  • 1513 Pine Street — photo52Active

    $1,899,000

    2 bd · 3 ba · 1,717 sqft

    1513 Pine Street, Key West, FL

    Jennifer M Newman · Truman & Co. (KW)

  • 1501 Georgia Street — photoPrice Reduced50Active

    $3,599,000

    4 bd · 5 ba · 2,810 sqft

    1501 Georgia Street, Key West, FL

    The Spottswood Team · Truman & Co. (KW)

  • 319 Grinnell Street — photoPrice Reduced61Active

    $2,395,000

    3 bd · 2 ba · 1,456 sqft

    319 Grinnell Street, Key West, FL

    Darrin N Smith · Key West Luxury Real Estate Inc (KW)

  • 3930 S Roosevelt Boulevard S205 — photoPrice Reduced33Active

    $559,000

    3 bd · 2 ba · 1,071 sqft

    3930 S Roosevelt Boulevard S205, Key West, FL

    Vic Musmanno · Coldwell Banker Schmitt Real Estate Co. (KW)

  • 906 Johnson Street — photoPrice Reduced65Active

    $5,500,000

    6 bd · 6 ba · 3,751 sqft

    906 Johnson Street, Key West, FL

    Regan Enouen · Truman & Co. (KW)

  • 919-921 Thomas Street — photoPrice Reduced91Active

    $3,750,000

    7 bd · 8 ba · 3,015 sqft

    919-921 Thomas Street, Key West, FL

    Rick L Lively · Coldwell Banker Schmitt Real Estate Co. (KW)

  • 709 Eaton Street — photoPrice Reduced37Active

    $4,695,000

    4 bd · 5 ba · 2,716 sqft

    709 Eaton Street, Key West, FL

    Will Langley · Berkshire Hathaway HomeServices Knight & Gardner Realty

  • 1901 S Roosevelt Boulevard 202 W — photoPrice Reduced36Active

    $1,190,000

    2 bd · 2 ba · 1,099 sqft

    1901 S Roosevelt Boulevard 202 W, Key West, FL

    Robert J Donahue · Key West Luxury Real Estate Inc (KW)

  • 123 Golf Club Drive — photo33Active

    $669,000

    2 bd · 2 ba · 780 sqft

    123 Golf Club Drive, Key West, FL

    Robert J Donahue · Key West Luxury Real Estate Inc (KW)

  • 2601 S Roosevelt Boulevard 304C — photoPrice Reduced21Active

    $799,000

    3 bd · 2 ba · 1,221 sqft

    2601 S Roosevelt Boulevard 304C, Key West, FL

    Andrea Leskova Otava · Last Key Realty, Inc (KW)

  • 202 Golf Club Drive — photoPrice Reduced23Active

    $799,000

    2 bd · 3 ba · 1,120 sqft

    202 Golf Club Drive, Key West, FL

    The Behmke Group · Keller Williams Key West Compass Realty

  • 2601 S Roosevelt Boulevard 204a — photoPrice Reduced26Active

    $599,000

    1 bd · 1 ba · 754 sqft

    2601 S Roosevelt Boulevard 204a, Key West, FL

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

  • 1901 S Roosevelt Boulevard 401E — photoPrice Reduced40Active

    $1,425,000

    3 bd · 2 ba · 1,395 sqft

    1901 S Roosevelt Boulevard 401E, Key West, FL

    Emily Lombard · Ocean Sotheby's International Realty

  • 815 Pearl Street 2 — photoPrice Reduced27Active

    $575,000

    1 bd · 1 ba · 546 sqft

    815 Pearl Street 2, Key West, FL

    Tracey Gardiner · Realty ONE Group Destination

  • 1203 Newton Street 1 — photo25Active

    $699,000

    1 bd · 1 ba · 427 sqft

    1203 Newton Street 1, Key West, FL

    Wendy L Zintsmaster · Truman & Co. (KW)

  • 2613 Gulfview Drive — photo36Active

    $1,549,000

    3 bd · 3 ba · 1,320 sqft

    2613 Gulfview Drive, Key West, FL

    Cardenas & Krug Team · Coastal Collection Real Estate Inc.

  • 48 Merganser Lane — photoPrice Reduced30Active

    $619,000

    2 bd · 2 ba · 780 sqft

    48 Merganser Lane, Key West, FL

    Jose Wenzel, PA · Preferred Properties (KW)

  • 1…4567
    Realty.com

    L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

    Equal Housing OpportunityEqual Housing Lender

    The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

    © 2026 Realty.com. All rights reserved.·Privacy·Terms·California Privacy Rights·Accessibility·Licensing

    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #BK3453168

    Call Thomas

    Listing data & MLS disclosures

    Key West Association of REALTORS
    The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of The Key West Association of REALTORS®. MLS Real Estate listings held by brokerage firms other than this broker are marked with the MLS logo and detailed information about them includes the name of the listing broker's office. The properties displayed may not be all of the properties in the MLS's database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Properties listed by Brokers other than this Broker are marked with either the listing Broker's logo or name or the MLS name or a logo provided by the MLS. Detailed information about such properties includes the name of the listing Brokers. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user. The Florida Association of Realtors and its cooperating MLSs do not create, control or review the property data displayed herein and take no responsibility for the content of such records. Federal law prohibits discrimination on the basis of race, color, religion, sex, handicap, familial status or national origin in the sale, rental or financing of housing. Information deemed reliable but not guaranteed. Copyright ©2026 The Key West Association of REALTORS®. All Rights Reserved.

    Key West, FL community profile

    Population
    25,696
    Median income
    $84,673
    Housing units
    14,524
    People per sq. mi.
    179.2
    Area
    143.4 sq. mi.

    Source: HJN community data

    Key West housing market

    September 2026 · This period is still settling

    Key West 12-month median sale price trend

    Selling at 94.9% of asking price

    Buyers here are paying below asking. MLS · 30 sales · as of Sep 25, 2026

    Homes that sold · County records, as of Sep 17, 2026

    Median sale price
    $1,150,000$807,500–$1,650,000 typical range
    Price per sq. ft.
    $756
    Sales
    23
    Paid in cash
    52.2%

    Homes on the market · MLS, as of Sep 25, 2026–Sep 27, 2026

    Median list price
    $1,100,000
    Homes for sale
    285
    Median days on market
    83 days

    Price trend · Assessor repeat sales, as of Sep 30, 2026

    Year-over-year
    22.2%

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 11, 2026

    Median home size
    1,400 sq. ft.