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Winter Haven, FL Homes for Sale — Page 20 | 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 766 Listings

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24 of 766 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Price Reduced40Active
$220,000
3 bd · 2 ba · 1,651 sqft
381 San Jose Dr, Winter Haven, FL
Patricia De Graaff, LLC · RE/MAX HERITAGE PROFESSIONALS
Price Reduced15Active
$265,000
4 bd · 2 ba · 1,675 sqft
3357 Timberline Rd W, Winter Haven, FL
Steven Koleno · BEYCOME OF FLORIDA LLC
Price Reduced10Active
$322,750
3 bd · 2 ba · 1,734 sqft
2748 San Marco Way, Winter Haven, FL
Osvaldo Junior · WRA BUSINESS & REAL ESTATE

28Active
$400,000
2 bd · 2 ba · 1,120 sqft
1549 Drexel Ave NE, Winter Haven, FL
Michael Brenner · CENTURY 21 MYERS REALTY
51Active
$245,000
3 bd · 2 ba · 1,464 sqft
1912 Carnostie Rd, Winter Haven, FL
Renee Butler · BROKERS REALTY OF CENTRAL FLOR
Price Reduced36Active
$165,000
3 bd · 2 ba · 1,306 sqft
124 Center St, Winter Haven, FL
Stephen Novak · LIVE FLORIDA REALTY
38Active
$286,900
3 bd · 2 ba · 1,725 sqft
3184 Royal Tern Dr, Winter Haven, FL
Sara Avellaneda · OPULENT REALTY INTERNATIONAL
Price Reduced25Active
$278,900
3 bd · 2 ba · 1,504 sqft
4129 Giorgio Dr, Winter Haven, FL
Stephen Cline · DR HORTON REALTY OF CENTRAL FLORIDA LLC
35Active
$249,900
3 bd · 2 ba · 1,232 sqft
2456 Bates Ave SW, Winter Haven, FL
J. Michael Nolen, JR · COLDWELL BANKER REALTY
Price Reduced44Active
$415,000
3 bd · 2 ba · 1,927 sqft
4840 Old Lucerne Park Rd, Winter Haven, FL
Cheryl Bossarte · POLK REAL ESTATE LLC
74Active
$124,900
2 bd · 2 ba · 1,403 sqft
4158 Rolling Oaks Dr, Winter Haven, FL
KATHY Devor · COLDWELL BANKER REALTY
Price Reduced21Active
$294,999
3 bd · 2 ba · 1,951 sqft
265 Majestic Gardens Ln, Winter Haven, FL
Andrew Fearn · BHHS FLORIDA PROPERTIES GROUP
21Active
$258,000
3 bd · 2 ba · 1,259 sqft
151 1st St, Winter Haven, FL
Milli Collins · MILLI REAL ESTATE SERVICES LLC
Price Reduced24Active
$379,900
4 bd · 2 ba · 1,960 sqft
301 Terranova Blvd, Winter Haven, FL
Rosa Nieves · LA ROSA REALTY KISSIMMEE
67Active
$129,000
2 bd · 2 ba · 1,344 sqft
4132 Sprucewood St, Winter Haven, FL
KATHY Devor · COLDWELL BANKER REALTY
Price Reduced29Active
$172,500
2 bd · 2 ba · 1,398 sqft
1026 Medinah Dr, Winter Haven, FL
Steven Smith, PA · LOCKHART & ASSOCIATES INC
52Active
$589,500
5 bd · 5 ba · 2,626 sqft
1302 Lake Elbert Dr SE, Winter Haven, FL
Russ Yerton · ELEVATE REAL ESTATE BROKERS
25Active
$149,900
1 bd · 1 ba · 666 sqft
2049 San Marcos Dr SE #127, Winter Haven, FL
Daniel Hut · HUT REALTY, LLC
Price Reduced20Active
$229,900
3 bd · 1 ba · 1,064 sqft
217 4th Jpv St, Winter Haven, FL
Tiffany Steck · BHHS FLORIDA PROPERTIES GROUP
Price Reduced57Active
$519,990
5 bd · 3 ba · 2,653 sqft
445 Talamone Dr, Winter Haven, FL
Jimmy Aguilar · 3D TEAM REALTY LLC
Price Reduced30Active
$299,900
3 bd · 3 ba · 1,892 sqft
6 Golfview Cir NE, Winter Haven, FL
Keith St. Onge · LA ROSA REALTY PRESTIGE
Price Reduced19Active
$294,900
4 bd · 2 ba · 1,851 sqft
996 Summer Glen Dr, Winter Haven, FL
Robert Salmons · ENTERA REALTY LLC
Price Reduced24Active
$349,950
3 bd · 2 ba · 1,467 sqft
3038 Thornhill Rd, Winter Haven, FL
Angie Reynolds · PORCHLIGHT HOMES LLC
32Active
$99,000
3 bd · 2 ba · 1,226 sqft
333 Lake Howard Dr NW #314D, Winter Haven, FL
Justin Cans · IMPACT REALTY TAMPA BAY

1…19 20 21…32

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 (1,176)
34746 (827)
33837 (722)
33896 (567)
33844 (557)
34759 (482)
33897 (446)
33884 (339)

Cities

Kissimmee (2,908)
Davenport (1,709)
Lakeland (1,148)
Haines City (555)
Lake Wales (403)
Auburndale (249)
Orlando (158)
Lake Alfred (139)

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 (1,176)
34746 (827)
33837 (722)
33896 (567)
33844 (557)
34759 (482)
33897 (446)
33884 (339)

Cities

Kissimmee (2,908)
Davenport (1,709)
Lakeland (1,148)
Haines City (555)
Lake Wales (403)
Auburndale (249)
Orlando (158)
Lake Alfred (139)