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Winter Haven, FL Homes for Sale — Page 25 | Realty.com

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3 beds New construction With a pool

Homes for Sale in Winter Haven, FL

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23 of 775 Listings

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23 of 775 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Price Reduced56Active
$249,000
3 bd · 2 ba · 1,035 sqft
113 6th Jpv St, Winter Haven, FL
John Evans · CENTURY 21 BEGGINS ENTERPRISES
Price Reduced28Active
$265,000
2 bd · 1 ba · 2,142 sqft
Address withheld · Winter Haven, FL
Marcia Rains - Nadal, Mrs · YELLOWFIN REALTY
Price Reduced45Active
$279,900
3 bd · 2 ba · 1,569 sqft
851 Vienna Dr, Winter Haven, FL
Regina Moran PA · LA ROSA REALTY PRESTIGE

Price Reduced25Active
$255,000
3 bd · 2 ba · 1,711 sqft
4140 Sophia Blvd, Winter Haven, FL
William Kilpatrick · KELLER WILLIAMS TAMPA CENTRAL
56Active
$195,000
2 bd · 2 ba · 1,008 sqft
4925 Cypress Gardens Rd #100, Winter Haven, FL
KATHY Devor · COLDWELL BANKER REALTY
Price Reduced37Active
$380,000
5 bd · 3 ba · 2,696 sqft
1328 Daisy Field Dr, Winter Haven, FL
David Small · KELLER WILLIAMS REALTY SMART 1
55Active
$146,000
2 bd · 2 ba · 1,107 sqft
6473 Peppertree Path NE, Winter Haven, FL
Don Cleveland, JR · COLDWELL BANKER REALTY
Price Reduced11Active
$195,000
3 bd · 1 ba · 1,144 sqft
231 Avenue a NE, Winter Haven, FL
Michael Hochadel · BHHS FLORIDA PROPERTIES GROUP
Price Reduced59Active
$95,000
2 bd · 2 ba · 720 sqft
4173 Rolling Oaks Dr, Winter Haven, FL
KATHY Devor · COLDWELL BANKER REALTY
61Active
$429,500
4 bd · 4 ba · 2,766 sqft
139 Woden Way, Winter Haven, FL
Glenda Pruitt · FLORIDA HOME CHOICE REALTY
Open house Sat, Oct 17 · 10:00 AM75Active
$579,900
3 bd · 2 ba · 2,354 sqft
5268 Pebble Beach Blvd, Winter Haven, FL
Barb Wiechmann · ROOST REALTY GROUP LLC
Price Reduced62Active
$359,000
3 bd · 2 ba · 1,914 sqft
131 Ruby Lake Dr, Winter Haven, FL
CarLee Marchetti · STAR REALTY OF WINTER HAVEN
Price Reduced32Active
$247,990
3 bd · 2 ba · 1,432 sqft
961 Harold Pass, Winter Haven, FL
Marian Capriles Garcia · LPT REALTY, LLC
Price Reduced20Active
$254,900
3 bd · 2 ba · 1,437 sqft
204 Kingshill Ct SE, Winter Haven, FL
Robert Salmons · ENTERA REALTY LLC
Price Reduced65Active
$115,000
2 bd · 2 ba · 1,200 sqft
4155 Sprucewood St, Winter Haven, FL
KATHY Devor · COLDWELL BANKER REALTY
Price Reduced59Active
$257,000
3 bd · 2 ba · 1,292 sqft
542 Eagle Landing Boulevard, Winter Haven, FL
Carla Miro · CENTURY 21 WATSON & MYERS REALTY
Price Reduced54Active
$154,000
2 bd · 2 ba · 1,248 sqft
6309 Grove Pointe Dr SE, Winter Haven, FL
Sanda Andrews · GOOD COMPANY REALTY INC.
Price Reduced21Active
$168,000
2 bd · 3 ba · 1,184 sqft
2500 21st St NW #15, Winter Haven, FL
Adriana Sanchez · AROD PARTNERS REALTY
Price Reduced32Active
$293,899
4 bd · 3 ba · 1,764 sqft
1382 Salisbury Dr, Winter Haven, FL
Cathy Stripling · STACEY TOWNS REALTY LLC
86Active
$720,000
4 bd · 4 ba · 2,961 sqft
237 Mclean Point, Winter Haven, FL
Luis Perez Garcia · EXP Realty LLC
Price Reduced63Active
$139,900
2 bd · 2 ba · 1,056 sqft
6773 Brentwood Dr NE, Winter Haven, FL
KATHY Devor · COLDWELL BANKER REALTY
Price Reduced28Active
$151,000
2 bd · 2 ba · 1,144 sqft
6450 Hollyberry Ln NE, Winter Haven, FL
David Small · KELLER WILLIAMS REALTY SMART 1
Price ReducedOpen house Wed, Oct 7 · 12:00 PM18Active
$334,999
4 bd · 3 ba · 2,077 sqft
5347 Mickey Ave, Winter Haven, FL
Stephanie Morales, LLC · AXEN REALTY, LLC

1…24 25 26…33

Listing data & MLS disclosures

MIAMI REALTORS MLS: The multiple listing information is provided by MIAMI Association of Realtors® from a copyrighted compilation of listings. The compilation of listings and each individual listingare ©2026 MIAMI Association of Realtors®. All Rights Reserved.
The information provided is for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All properties are subject to prior sale or withdrawal. All information provided is deemed reliable but is not guaranteed accurate, and should be independently verified. Last Updated: 2026-04-04 00:01:06 UTC
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

MIAMI REALTORS MLS: The multiple listing information is provided by MIAMI Association of Realtors® from a copyrighted compilation of listings. The compilation of listings and each individual listingare ©2026 MIAMI Association of Realtors®. All Rights Reserved.
The information provided is for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All properties are subject to prior sale or withdrawal. All information provided is deemed reliable but is not guaranteed accurate, and should be independently verified. Last Updated: 2026-04-04 00:01:06 UTC
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)