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Winter Haven, FL Homes for Sale — Page 24 | Realty.com

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3 beds New construction With a pool

Homes for Sale in Winter Haven, FL

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24 of 774 Listings

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24 of 774 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Price Reduced37Active
$329,900
3 bd · 2 ba · 1,160 sqft
1558 Drexel Ave NE, Winter Haven, FL
David Small · KELLER WILLIAMS REALTY SMART 1
Price ReducedOpen house Sun, Oct 11 · 1:00 PM33Active
$724,999
5 bd · 5 ba · 3,703 sqft
2656 Wyndsor Oaks Way, Winter Haven, FL
Jonathan Minerick · HOMECOIN.COM
27Active
$246,900
3 bd · 1 ba · 1,174 sqft
218 Dennis Ave, Winter Haven, FL
Anne Halbert · LIVE FLORIDA REALTY

Price Reduced33Active
$603,000
3 bd · 2 ba · 2,100 sqft
12 Cherry Blossom Ln, Winter Haven, FL
Maribel Ramos, LLC · VESTI LLC
26Active
$279,000
4 bd · 3 ba · 2,368 sqft
884 Cambridge Dr, Winter Haven, FL
Dana Cates · FOUNDATION REALTY GROUP
Price Reduced29Active
$189,000
2 bd · 2 ba · 972 sqft
1213 8th St NW, Winter Haven, FL
Holly Patterson · KELLER WILLIAMS REALTY SMART
Price Reduced31Active
$165,000
3 bd · 1 ba · 912 sqft
300 Avenue V NE, Winter Haven, FL
Casandra Vann · KELLER WILLIAMS REALTY SMART
14Active
$179,000
3 bd · 1 ba · 768 sqft
306 Palmetto Ave NW, Winter Haven, FL
Hamid Dghirni · PREMIUM PROPERTIES R.E. SERVICE
Price Reduced42Active
$159,900
2 bd · 2 ba · 1,288 sqft
6114 Grand Oaks Dr SE, Winter Haven, FL
Kimberly Davis · CROSBY & ASSOCIATES, INC.
Price Reduced32Active
$299,900
3 bd · 2 ba · 1,764 sqft
202 Saint Lucie Rd, Winter Haven, FL
John Calhoun · CENTURY 21 WATSON & MYERS REALTY
Price Reduced32Active
$339,900
3 bd · 2 ba · 1,884 sqft
314 Terranova Blvd, Winter Haven, FL
Jeff Jones · MARK SPAIN REAL ESTATE
21Active
$386,990
4 bd · 3 ba · 2,797 sqft
1726 Upland Ln, Winter Haven, FL
Bill Maltbie · MALTBIE REALTY GROUP
Price Reduced20Active
$250,000
4 bd · 2 ba · 1,713 sqft
3732 Giorgio Dr, Winter Haven, FL
Yoja Mirabal · MY REALTY GROUP, LLC.
17Active
$392,175
4 bd · 3 ba · 2,551 sqft
1742 Upland Ln, Winter Haven, FL
Bill Maltbie · MALTBIE REALTY GROUP
Price Reduced32Active
$284,990
3 bd · 2 ba · 1,680 sqft
2747 San Marco Way, Winter Haven, FL
Vilmari Caraballo · RE/MAX ASSURED
Price Reduced20Active
$214,990
3 bd · 3 ba · 1,386 sqft
3056 Captain Jax Way, Winter Haven, FL
Ben Goldstein · LENNAR REALTY
Price Reduced30Active
$205,000
2 bd · 3 ba · 1,280 sqft
323 Orange Blossom Dr #323, Winter Haven, FL
Rick Hemenway · CROSBY & ASSOCIATES, INC.
68Active
$395,000
4 bd · 3 ba · 2,322 sqft
3890 Bedford Ave, Winter Haven, FL
Christie Weeks · DREAM REALTY GROUP
48Active
$289,900
3 bd · 2 ba · 1,674 sqft
3971 Cypress Lndg W, Winter Haven, FL
Kevin Tison · LPT REALTY, LLC
Price Reduced27Active
$309,000
4 bd · 2 ba · 1,992 sqft
4669 Osprey Way, Winter Haven, FL
Greg Owen · EASY REALTY
Price Reduced35Active
$251,900
3 bd · 2 ba · 1,506 sqft
909 Cambridge Dr, Winter Haven, FL
Mariel Espinal · AXEN REALTY, LLC
Price Reduced31Active
$364,900
5 bd · 3 ba · 2,244 sqft
1783 White Elephant Loop, Winter Haven, FL
Gayle Van Wagenen · LGI REALTY- FLORIDA, LLC
48Active
$145,000
2 bd · 2 ba · 1,000 sqft
447 Village Cir SW, Winter Haven, FL
KATHY Devor · COLDWELL BANKER REALTY
Price Reduced56Active
$249,000
3 bd · 2 ba · 1,035 sqft
113 6th Jpv St, Winter Haven, FL
John Evans · CENTURY 21 BEGGINS ENTERPRISES

1…23 24 25…33

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.

Winter Haven housing market

September 2026 · This period is still settling

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.

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

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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

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.

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.

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

New Construction Homes

Homes with a Pool

Waterfront Homes

Foreclosures & Short Sales

55+ Community Homes

Nearby areas

ZIP codes

34747 (2,308)
34746 (1,655)
33837 (1,450)
33896 (1,137)
33844 (1,103)
34759 (922)
33897 (894)
33884 (682)

Cities

Kissimmee (5,756)
Davenport (3,437)
Lakeland (2,278)
Haines City (1,100)
Lake Wales (766)
Auburndale (504)
Bartow (267)
Lake Alfred (266)

Your local brokerage

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

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 (2,308)
34746 (1,655)
33837 (1,450)
33896 (1,137)
33844 (1,103)
34759 (922)
33897 (894)
33884 (682)

Cities

Kissimmee (5,756)
Davenport (3,437)
Lakeland (2,278)
Haines City (1,100)
Lake Wales (766)
Auburndale (504)
Bartow (267)
Lake Alfred (266)