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

Save search

Map layers

Safety

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 | 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

776 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 776 Listings
Map

Homes for Sale in Winter Haven, FL

24 of 776 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas
  1. 1075 8th St NW — photo52Active

    $480,000

    4 bd · 3 ba · 1,985 sqft

    1075 8th St NW, Winter Haven, FL

    Jim Knetsch · LPT REALTY, LLC

  2. 193 E Sweet Cir — photoNew19Active

    $110,000

    2 bd · 2 ba · 1,300 sqft

    193 E Sweet Cir, Winter Haven, FL

    Darlene Bice · TOWN & COUNTRY REAL ESTATE

  3. 6216 Pinehurst Loop — photoNewOpen house Sat, Oct 10 · 10:00 AM68Active

    $429,000

    3 bd · 2 ba · 2,045 sqft

    6216 Pinehurst Loop, Winter Haven, FL

    Lori Raath · LAKE ASHTON REALTY INC.

  4. 218 6th Jpv St — photoNew25Active

    $255,000

    3 bd · 2 ba · 1,228 sqft

    218 6th Jpv St, Winter Haven, FL

    Renee Butler · BROKERS REALTY OF CENTRAL FLOR

  5. 10 Lychee Dr — photo36Active

    $130,000

    1 bd · 2 ba · 720 sqft

    10 Lychee Dr, Winter Haven, FL

    Nicole Curtin · 54 REALTY LLC

  6. 217 Grove Ridge Dr — photo39Active

    $160,000

    2 bd · 2 ba · 1,344 sqft

    217 Grove Ridge Dr, Winter Haven, FL

    Maria Guillen-Hug · LA ROSA REALTY PRESTIGE

  7. 1331 Haines Dr — photo36Active

    $249,000

    3 bd · 2 ba · 1,471 sqft

    1331 Haines Dr, Winter Haven, FL

    David Small · KELLER WILLIAMS REALTY SMART 1

  8. 2426 6th St NE — photoNew46Active

    $240,000

    3 bd · 2 ba · 1,447 sqft

    2426 6th St NE, Winter Haven, FL

    Frankie Eizere · RE/MAX HERITAGE PROFESSIONALS

  9. 1097 Carefree Cove Dr — photoNewOpen house Sat, Oct 17 · 11:00 AM50Active

    $319,900

    3 bd · 2 ba · 1,484 sqft

    1097 Carefree Cove Dr, Winter Haven, FL

    Frankie Eizere · RE/MAX HERITAGE PROFESSIONALS

  10. 200 El Camino #106 — photoNew27Active

    $79,000

    1 bd · 1 ba · 1,078 sqft

    200 El Camino #106, Winter Haven, FL

    Cynthia Cole · FLORIDA REALTY MARKETPLACE

  11. 1044 Luke Ave — photoNew26Active

    $309,990

    4 bd · 2 ba · 1,758 sqft

    1044 Luke Ave, Winter Haven, FL

    Nancy Pruitt, PA · OLYMPUS EXECUTIVE REALTY INC

  12. 1048 Luke Ave — photoNew1Active

    $314,990

    4 bd · 2 ba · 1,938 sqft

    1048 Luke Ave, Winter Haven, FL

    Nancy Pruitt, PA · OLYMPUS EXECUTIVE REALTY INC

  13. 1056 Luke Ave — photoNew1Active

    $309,990

    4 bd · 2 ba · 1,938 sqft

    1056 Luke Ave, Winter Haven, FL

    Nancy Pruitt, PA · OLYMPUS EXECUTIVE REALTY INC

  14. 200 El Camino Dr #102 — photo35Active

    $97,000

    2 bd · 2 ba · 1,378 sqft

    200 El Camino Dr #102, Winter Haven, FL

    Dawn Perkins · LEGACY REAL ESTATE CENTER INC

  15. 5288 Green Dr — photoNew64Active

    $314,000

    3 bd · 2 ba · 1,847 sqft

    5288 Green Dr, Winter Haven, FL

    Pat Pearson · VIEWPOINT VALUE REALTY

  16. 714 Avenue O SE — photoNew33Active

    $359,900

    5 bd · 2 ba · 2,104 sqft

    714 Avenue O SE, Winter Haven, FL

    Ileana Perez · HOUWZER INC

  17. 104 13th St SE — photoNew21Active

    $200,000

    2 bd · 2 ba · 1,776 sqft

    104 13th St SE, Winter Haven, FL

    Chuck Ferdinandsen · CHARLES RUTENBERG REALTY ORLANDO

  18. 988 Cambridge Dr — photoNew27Active

    $299,900

    4 bd · 2 ba · 1,867 sqft

    988 Cambridge Dr, Winter Haven, FL

    Adrian Alanis Arredondo · THE ORANGE REAL ESTATE GROUP

  19. 2352 Isle Royale Ct SE — photoNew48Active

    $217,000

    2 bd · 3 ba · 1,281 sqft

    2352 Isle Royale Ct SE, Winter Haven, FL

    Michelle Armbruster · LOCKHART & ASSOCIATES INC

  20. 5101 Magnolia Preserve Blvd — photo52Active

    $259,900

    3 bd · 3 ba · 1,394 sqft

    5101 Magnolia Preserve Blvd, Winter Haven, FL

    Manny Quiros · RE/MAX HERITAGE PROFESSIONALS

  21. 1841 5th St SE — photo70Active

    $339,000

    3 bd · 2 ba · 1,917 sqft

    1841 5th St SE, Winter Haven, FL

    Juan Jose JR Sanchez, PA · KELLER WILLIAMS REALTY AT THE LAKES

  22. 575 Saint Andrews Rd — photo34Active

    $286,000

    2 bd · 2 ba · 1,429 sqft

    575 Saint Andrews Rd, Winter Haven, FL

    Elaine Sanders · HOUSE OF GLASS REAL ESTATE PM

  23. 842 Avenue N SW — photo18Active

    $175,000

    3 bd · 1 ba · 1,056 sqft

    842 Avenue N SW, Winter Haven, FL

    Brooke Madden · KELLER WILLIAMS TAMPA CENTRAL

  24. 10 W Lake Hamilton Cir — photo36Active

    $485,000

    4 bd · 2 ba · 2,400 sqft

    10 W Lake Hamilton Cir, Winter Haven, FL

    John Keller, III · JACK KELLER INC

12…33

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
  • Townhomes
  • Condos
  • Manufactured Homes

By feature

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.
  • New Construction Homes
  • Homes with a Pool
  • Waterfront Homes
  • Foreclosures & Short Sales
  • 55+ Community Homes
  • Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #BK3453168

    Call Thomas

    Nearby areas

    ZIP codes

    • 34747 (1,178)
    • 34746 (827)
    • 33837 (725)
    • 33896 (566)
    • 33844 (561)
    • 34759 (486)
    • 33897 (450)
    • 33884 (339)

    Cities

    • Kissimmee (2,905)
    • Davenport (1,715)
    • Lakeland (1,148)
    • Haines City (558)
    • Orlando (476)
    • Lake Wales (403)
    • Auburndale (247)
    • Winter Garden (241)

    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.