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Winter Haven, FL Homes for Sale — Page 19 | 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 767 Listings

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24 of 767 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Price Reduced54Active
$370,000
4 bd · 3 ba · 2,413 sqft
306 Terranova Blvd, Winter Haven, FL
Andrew Duncan · LPT REALTY LLC
Price Reduced12Active
$261,000
3 bd · 2 ba · 1,264 sqft
2121 Greenway Dr, Winter Haven, FL
Julie Tressler · TCAT REALTY SERVICES INC
15Active
$260,000
3 bd · 2 ba · 1,732 sqft
3180 Country Club Circle, Winter Haven, FL
Jon McCall · Dalton Wade Inc

Price Reduced15Active
$329,900
4 bd · 4 ba · 2,227 sqft
2820 San Marco Way E, Winter Haven, FL
George Lindsey, III · CAMBRIDGE REALTY OF CENTRAL FL
Price Reduced66Active
$405,000
5 bd · 2 ba · 2,992 sqft
199 8th St SE, Winter Haven, FL
Jenn Gibbs · SKYBROOK REALTY & ASSOCIATES, INC.
Price Reduced57Active
$310,000
3 bd · 2 ba · 2,109 sqft
3614 Plymouth Dr, Winter Haven, FL
Andrew Duncan · LPT REALTY LLC
Price Reduced9Active
$195,000
4 bd · 2 ba · 1,450 sqft
108 Edgewater Dr, Winter Haven, FL
Martineau Dimanche · INTELLIGENCE CHOICE REALTY LLC
9Active
$200,000
5 bd · 2 ba · 1,700 sqft
1605 36th St NW, Winter Haven, FL
Martineau Dimanche · INTELLIGENCE CHOICE REALTY LLC
64Active
$140,000
2 bd · 2 ba · 1,344 sqft
4146 Sprucewood St, Winter Haven, FL
KATHY Devor · COLDWELL BANKER REALTY
Price Reduced33Active
$229,000
2 bd · 2 ba · 1,395 sqft
664 Clubhouse Rd, Winter Haven, FL
Eileen Belanger · CENTURY 21 MYERS REALTY LAKE WALES
Price Reduced38Active
$178,490
2 bd · 3 ba · 1,334 sqft
2500 21st St NW #22, Winter Haven, FL
David Small · KELLER WILLIAMS REALTY SMART 1
8Active
$350,000
3 bd · 2 ba · 1,322 sqft
0 38th St NW, Winter Haven, FL
Heather Spinosa · MIHARA & ASSOCIATES INC.
Price Reduced23Active
$449,000
2 bd · 3 ba · 965 sqft
1620 17th St NW, Winter Haven, FL
Kimberly Saddler · LA ROSA REALTY PRESTIGE
10Active
$350,000
3 bd · 2 ba · 1,327 sqft
0 38th St NW, Winter Haven, FL
Heather Spinosa · MIHARA & ASSOCIATES INC.
8Active
$350,000
3 bd · 2 ba · 1,322 sqft
0 38th St NW, Winter Haven, FL
Heather Spinosa · MIHARA & ASSOCIATES INC.
8Active
$350,000
3 bd · 2 ba · 1,322 sqft
0 38th St NW, Winter Haven, FL
Heather Spinosa · MIHARA & ASSOCIATES INC.
Open house Sat, Oct 10 · 1:00 PM18Active
$340,000
4 bd · 2 ba · 1,828 sqft
937 Cattleman St, Winter Haven, FL
Isabelle Maye · BHHS FLORIDA PROPERTIES GROUP
31Active
$200,999
2 bd · 1 ba · 968 sqft
1101 28th St NW, Winter Haven, FL
Yulimar Machado · OUTLET REALTY
8Active
$189,000
3 bd · 1 ba · 744 sqft
345 Avenue P NE, Winter Haven, FL
Ivette Graves · RODRIGUEZ PROPERTY MANAGEMENT
Price Reduced23Active
$239,000
3 bd · 2 ba · 1,369 sqft
3430 Fox Ridge St, Winter Haven, FL
Blanca Armada · REMAX PREMIER PROPERTIES
Price Reduced7Active
$279,000
4 bd · 2 ba · 1,607 sqft
3960 Giorgio Dr, Winter Haven, FL
Bryan Sumner · MERITAGE HOMES OF FL REALTY
Price Reduced25Active
$199,000
2 bd · 2 ba · 1,090 sqft
105 Laurel Cove Way #105, Winter Haven, FL
Chip Fortenberry, III · CROSBY & ASSOCIATES, INC.
Price Reduced30Active
$272,990
3 bd · 2 ba · 1,698 sqft
136 Krenson Bay Loop, Winter Haven, FL
Lisa Manzo · WIN-WIN REAL ESTATE SERVICES LLC
Price Reduced35Active
$304,990
4 bd · 2 ba · 1,758 sqft
300 Meredith Blvd, Winter Haven, FL
Nancy Pruitt, PA · OLYMPUS EXECUTIVE REALTY INC

1…18 19 20…32

Listing data & MLS disclosures

Hernando County Association of REALTORS: Copyright 2026 of Hernando County AOR MLS. All rights reserved. IDX Data is provided exclusively for consumers’ personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that data is deemed reliable but is not guaranteed accurate by the Hernando County AOR MLS. Last Updated: 2026-06-22 16:39:53 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

Hernando County Association of REALTORS: Copyright 2026 of Hernando County AOR MLS. All rights reserved. IDX Data is provided exclusively for consumers’ personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that data is deemed reliable but is not guaranteed accurate by the Hernando County AOR MLS. Last Updated: 2026-06-22 16:39:53 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 (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

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)

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.