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Winter Haven, FL Homes for Sale | 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 795 Listings

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24 of 795 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

New42Active
$285,000
3 bd · 2 ba · 1,432 sqft
668 Reggie Rd, Winter Haven, FL
Kenny Medina · LPT REALTY, LLC
New71Active
$165,500
2 bd · 2 ba · 1,176 sqft
6733 Kensington Dr NE, Winter Haven, FL
Cynthia Cole · FLORIDA REALTY MARKETPLACE
New42Active
$380,000
3 bd · 2 ba · 1,020 sqft
417 Avenue G SE, Winter Haven, FL
Arlin De Leon, PA · LA ROSA REALTY KISSIMMEE

New37Active
$459,000
4 bd · 2 ba · 2,069 sqft
114 Belmont Dr, Winter Haven, FL
Mark Bouchard · MLB FREEDOM DESTINATIONS
New64Active
$249,900
3 bd · 2 ba · 1,140 sqft
240 Westwood Ave, Winter Haven, FL
Nicole Silva · RE/MAX COLLECTIVE
New33Active
$225,000
3 bd · 2 ba · 1,245 sqft
125 Whittier Ln, Winter Haven, FL
Lori Roberts · GOLD HEART REALTY LLC
New87Active
$1,295,000
3 bd · 3 ba · 2,375 sqft
1921 Manor Cir SE, Winter Haven, FL
Dee Norris · NEXTHOME NORRIS & COMPANY REAL
New42Active
$289,000
4 bd · 2 ba · 1,851 sqft
138 Grove Branch Rd, Winter Haven, FL
Michael Stone · THE STONES REAL ESTATE FIRM
New1Active
$319,999
4 bd · 3 ba · 2,039 sqft
5365 San Pietro Dr, Winter Haven, FL
Michael Human · CASA FRESCA REALTY
New15Active
$294,990
5 bd · 3 ba · 2,112 sqft
6245 Botticella Blvd, Winter Haven, FL
Ben Goldstein · LENNAR REALTY
New22Active
$278,000
4 bd · 2 ba · 1,830 sqft
703 Avenue L SE, Winter Haven, FL
Sandra Wyhnanskyj, PA · OLYMPUS EXECUTIVE REALTY INC
New1Active
$364,745
5 bd · 3 ba · 2,470 sqft
1759 Vanilla St, Winter Haven, FL
Michael Human · CASA FRESCA REALTY
New1Active
$410,620
4 bd · 3 ba · 2,292 sqft
1764 Vanilla St, Winter Haven, FL
Michael Human · CASA FRESCA REALTY
New1Active
$333,090
4 bd · 3 ba · 2,039 sqft
1767 Vanilla St, Winter Haven, FL
Michael Human · CASA FRESCA REALTY
New31Active
$428,000
5 bd · 3 ba · 2,549 sqft
219 Terranova Blvd, Winter Haven, FL
Dwight Head · ALLSTATE REALTY SERVICES
72Active
$399,999
4 bd · 4 ba · 2,960 sqft
1217 Michelangelo Ln, Winter Haven, FL
Jocelyne Yanez · HOMESMART
New25Active
$515,000
5 bd · 3 ba · 2,685 sqft
2022 Kapree Ct, Winter Haven, FL
Jerome Baker · BAKER REAL ESTATE PRO. GR LLC
New48Active
$319,990
4 bd · 2 ba · 2,004 sqft
1127 Seedorf Dr, Winter Haven, FL
Juan Acevedo · FORTUNE INTERNATIONAL REALTY
New30Active
$337,500
3 bd · 2 ba · 2,034 sqft
1400 Avenue D NE, Winter Haven, FL
Glenda Pruitt · FLORIDA HOME CHOICE REALTY
New42Active
$279,900
3 bd · 2 ba · 1,556 sqft
420 Hillcrest Dr SE, Winter Haven, FL
Raymond Thomas · STAR BAY REALTY CORP.
New49Active
$327,700
4 bd · 2 ba · 1,830 sqft
221 Avenue P NW, Winter Haven, FL
Madeline Rivera · INNOVATION GROUP REALTY LLC
19Active
$380,000
4 bd · 3 ba · 2,509 sqft
1652 Lemon Ave, Winter Haven, FL
Danny Chandler, Jr · COLDWELL BANKER REALTY
New65Active
$559,900
4 bd · 3 ba · 2,775 sqft
7380 Bent Grass Dr, Winter Haven, FL
Twanna Dewdney · LA ROSA REALTY PRESTIGE
New21Active
$130,000
3 bd · 2 ba · 1,678 sqft
1406 Meadow Dr NE, Winter Haven, FL
Cesar Estrada, PA · EXP REALTY LLC

1 2…34

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 99.9% of asking price

Sales here are closing essentially at asking. MLS · 138 sales · as of Sep 30, 2026

Homes that sold · County records, as of Sep 28, 2026

Median sale price: $270,000$196,000–$334,500 typical range
Price per sq. ft.: $160
Sales: 175
Paid in cash: 37.7%

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: 42 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.

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 99.9% of asking price

Sales here are closing essentially at asking. MLS · 138 sales · as of Sep 30, 2026

Homes that sold · County records, as of Sep 28, 2026

Median sale price: $270,000$196,000–$334,500 typical range
Price per sq. ft.: $160
Sales: 175
Paid in cash: 37.7%

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: 42 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.

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Homes with a Pool

Waterfront Homes

Foreclosures & Short Sales

55+ Community Homes

Nearby areas

ZIP codes

34747 (1,216)
34746 (841)
33837 (754)
33896 (573)
33844 (570)
34759 (484)
33897 (443)
33884 (347)

Cities

Kissimmee (2,966)
Davenport (1,742)
Lakeland (1,159)
Haines City (567)
Lake Wales (409)

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Nearby areas

ZIP codes

34747 (1,216)
34746 (841)
33837 (754)
33896 (573)
33844 (570)
34759 (484)
33897 (443)
33884 (347)

Cities

Kissimmee (2,966)
Davenport (1,742)
Lakeland (1,159)
Haines City (567)
Lake Wales (409)

Orlando (339)

Auburndale (252)

Winter Garden (203)