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
Winter Haven, FL Homes for Sale — Page 7 | Realty.com
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

1,549 listings
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
3 bedsNew constructionWith a pool

Homes for Sale in Winter Haven, FL

Homes for Sale in Winter Haven, FL

Hide Map
24 of 1,549 Listings
Map

Homes for Sale in Winter Haven, FL

24 of 1,549 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas
  1. 231 Hayley Street — photo29Active

    $319,999

    4 bd · 3 ba · 1,933 sqft

    231 Hayley Street, Winter Haven, FL

    Vilmari Caraballo · RE/MAX ASSURED

  2. 3708 Coffman Drive — photo47Active

    $235,000

    4 bd · 2 ba · 1,359 sqft

    3708 Coffman Drive, Winter Haven, FL

    Kamilla Pagotto · CENTURY 21 EDGE

  3. 231 Hayley St — photo29Active

    $319,999

    4 bd · 3 ba · 1,933 sqft

    231 Hayley St, Winter Haven, FL

    Vilmari Caraballo · RE/MAX ASSURED

  4. 742 Santa Maria Dr — photo59Active

    $409,900

    3 bd · 3 ba · 2,592 sqft

    742 Santa Maria Dr, Winter Haven, FL

    Rick Hemenway · CROSBY & ASSOCIATES, INC.

  5. 256 Krenson Bay Loop — photo30Active

    $290,000

    3 bd · 2 ba · 1,720 sqft

    256 Krenson Bay Loop, Winter Haven, FL

    Ingrid Santaliz · MARK SPAIN REAL ESTATE

  6. 1825 34th Street NW — photo48Active

    $209,000

    3 bd · 1 ba · 1,498 sqft

    1825 34th Street NW, Winter Haven, FL

    Dennis Romero Osorio · WEICHERT REALTORS HALLMARK PRO

  7. 9513 Waterford Oaks Blvd — photo66Active

    $750,000

    5 bd · 4 ba · 3,611 sqft

    9513 Waterford Oaks Blvd, Winter Haven, FL

    David Small · KELLER WILLIAMS REALTY SMART 1

  8. 742 Santa Maria Drive — photo59Active

    $409,900

    3 bd · 3 ba · 2,592 sqft

    742 Santa Maria Drive, Winter Haven, FL

    Rick Hemenway · CROSBY & ASSOCIATES, INC.

  9. 9513 Waterford Oaks Boulevard — photo66Active

    $750,000

    5 bd · 4 ba · 3,611 sqft

    9513 Waterford Oaks Boulevard, Winter Haven, FL

    David Small · KELLER WILLIAMS REALTY SMART 1

  10. 3708 Coffman Dr — photoPrice Reduced47Active

    $225,000

    4 bd · 2 ba · 1,359 sqft

    3708 Coffman Dr, Winter Haven, FL

    Kevin Johnson · CENTURY 21 EDGE

  11. 855 Killearn Blvd — photoPrice Reduced20Active

    $255,200

    3 bd · 2 ba · 1,449 sqft

    855 Killearn Blvd, Winter Haven, FL

    Blake Keathley · EVERYSTATE INC.

  12. 923 W Lake Cannon Drive NW — photo11Active

    $240,000

    3 bd · 2 ba · 1,375 sqft

    923 W Lake Cannon Drive NW, Winter Haven, FL

    Barbara Mollanazar · RE/MAX ALLIANCE GROUP

  13. 855 Killearn Boulevard — photo20Active

    $259,000

    3 bd · 2 ba · 1,449 sqft

    855 Killearn Boulevard, Winter Haven, FL

    Blake Keathley · EVERYSTATE INC.

  14. 1020 Lena Run Court — photo44Active

    $598,000

    5 bd · 3 ba · 3,068 sqft

    1020 Lena Run Court, Winter Haven, FL

    Sarah Garner · COLDWELL BANKER REALTY

  15. 923 W Lake Cannon Dr NW — photo11Active

    $240,000

    3 bd · 2 ba · 1,375 sqft

    923 W Lake Cannon Dr NW, Winter Haven, FL

    Barbara Mollanazar · RE/MAX ALLIANCE GROUP

  16. 809 Magnolia Place — photo36Active

    $235,000

    2 bd · 2 ba · 1,308 sqft

    809 Magnolia Place, Winter Haven, FL

    Laurie Nock · LPT REALTY, LLC

  17. 464 Fish Hawk Drive — photoPrice Reduced35Active

    $449,489

    6 bd · 5 ba · 3,920 sqft

    464 Fish Hawk Drive, Winter Haven, FL

    John Dannel · CFRP REALTY LLC

  18. 3785 Giorgio Dr — photo20Active

    $293,000

    4 bd · 2 ba · 1,978 sqft

    3785 Giorgio Dr, Winter Haven, FL

    Laura Petersen · YOUR HOME SOLD GUARANTEED REALTY

  19. 3541 Raleigh Dr — photo56Active

    $350,000

    3 bd · 3 ba · 2,006 sqft

    3541 Raleigh Dr, Winter Haven, FL

    Eileen Belanger · CENTURY 21 MYERS REALTY LAKE WALES

  20. 3785 Giorgio Drive — photo20Active

    $293,000

    4 bd · 2 ba · 1,978 sqft

    3785 Giorgio Drive, Winter Haven, FL

    Laura Petersen · YOUR HOME SOLD GUARANTEED REALTY

  21. 5325 Snead Drive — photo99Active

    $364,500

    3 bd · 2 ba · 1,833 sqft

    5325 Snead Drive, Winter Haven, FL

    Francis Alvarez Lopez · LA ROSA REALTY LLC

  22. 3541 Raleigh Drive — photo56Active

    $350,000

    3 bd · 3 ba · 2,006 sqft

    3541 Raleigh Drive, Winter Haven, FL

    Eileen Belanger · CENTURY 21 MYERS REALTY LAKE WALES

  23. 352 Lake Daisy Circle — photo31Active

    $259,900

    3 bd · 2 ba · 1,266 sqft

    352 Lake Daisy Circle, Winter Haven, FL

    Dawn Justice · CHARLES RUTENBERG REALTY INC

  24. 464 Fish Hawk Dr — photoPrice Reduced35Active

    $449,489

    6 bd · 5 ba · 3,920 sqft

    464 Fish Hawk Dr, Winter Haven, FL

    John Dannel · CFRP REALTY LLC

1…678…65

Explore Winter Haven homes

By price

  • Homes Under $100K
  • Homes Under $200K
  • Homes Under $300K
  • Homes Under $400K

By bedrooms

  • 2 Bedroom Homes
  • 3 Bedroom Homes
  • 4 Bedroom Homes
  • 5 Bedroom Homes

By type

  • Single-Family Homes
  • Condos
  • Manufactured Homes

By feature

  • New Construction Homes
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

Listing data & MLS disclosures

Stellar MLS
Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Listing information is provided for consumers? personal, non-commercial use, solely to identify prospective properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Information deemed reliable but not guaranteed. Copyright © 2026 MLS GRID. All Rights Reserved.
  • Homes with a Pool
  • Waterfront Homes
  • Open Houses
  • Foreclosures & Short Sales
  • 55+ Community Homes
  • Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #BK3453168

    Call Thomas

    Winter Haven, FL community profile

    Population
    58,351
    Median income
    $56,564
    Housing units
    26,800
    People per sq. mi.
    605.3
    Area
    96.4 sq. mi.

    Source: HJN community data

    Winter Haven housing market

    September 2026 · This period is still settling

    Winter Haven 12-month median sale price trend

    Selling at 99.7% of asking price

    Sales here are closing essentially at asking. MLS · 137 sales · as of Sep 30, 2026

    Homes that sold · County records, as of Sep 18, 2026

    Median sale price
    $270,000$207,500–$329,495 typical range
    Price per sq. ft.
    $161
    Sales
    135
    Paid in cash
    36.3%

    Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

    Median list price
    $294,400
    Homes for sale
    762
    Median days on market
    48 days

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

    Year-over-year
    -18.2%

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

    Median home size
    1,632 sq. ft.

    Nearby areas

    ZIP codes

    • 34747 (2,310)
    • 34746 (1,665)
    • 33837 (1,454)
    • 33896 (1,129)
    • 33844 (1,103)
    • 34759 (925)
    • 33897 (895)
    • 33884 (687)

    Cities

    • Kissimmee (2,913)
    • KISSIMMEE (2,856)
    • DAVENPORT (1,727)
    • Davenport (1,708)
    • Lakeland (1,157)
    • LAKELAND (1,121)
    • HAINES CITY (550)
    • Haines City (549)