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Winter Haven, FL Homes for Sale — Page 18 | 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 768 Listings

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24 of 768 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Price Reduced35Active
$222,000
2 bd · 1 ba · 1,199 sqft
1365 Sheridan St SW, Winter Haven, FL
Tina Ford · BERRY REALTY & APPRAISAL SERVICES PA
Price Reduced19Active
$229,900
3 bd · 2 ba · 1,253 sqft
2865 Whispering Trails Dr, Winter Haven, FL
Robert Salmons · ENTERA REALTY LLC
Price Reduced30Active
$316,380
4 bd · 3 ba · 2,039 sqft
5445 San Pietro Dr, Winter Haven, FL
Michael Human · CASA FRESCA REALTY

Price Reduced25Active
$239,900
3 bd · 2 ba · 1,580 sqft
715 Avenue B SW, Winter Haven, FL
Benjamin Crane · CITARELLI REALTY GROUP LLC
Price Reduced38Active
$255,000
3 bd · 2 ba · 1,652 sqft
415 8th St NE, Winter Haven, FL
Amanda Plowden · COLDWELL BANKER REALTY
Price Reduced36Active
$249,000
3 bd · 2 ba · 1,122 sqft
820 26th St NW, Winter Haven, FL
Sonya Duke · 241 REAL ESTATE LLC
Price Reduced16Active
$220,000
2 bd · 1 ba · 1,137 sqft
1405 28th St NW, Winter Haven, FL
Matthew Hazlett · EXP REALTY LLC
Price Reduced19Active
$249,900
3 bd · 2 ba · 1,406 sqft
406 Lake Daisy Dr, Winter Haven, FL
Robert Salmons · ENTERA REALTY LLC
5Active
$329,900
4 bd · 3 ba · 1,896 sqft
1642 Teagan Ln, Winter Haven, FL
Steven Koleno · BEYCOME OF FLORIDA LLC
56Active
$215,000
3 bd · 3 ba · 1,549 sqft
2216 Starboard, Winter Haven, FL
Bree Allison · KELLER WILLIAMS TAMPA CENTRAL
Price Reduced65Active
$574,900
4 bd · 3 ba · 2,916 sqft
1801 Sandhill Ln, Winter Haven, FL
Emily Cassidy · LAND SOURCE REALTY, LLC
Price Reduced35Active
$334,900
5 bd · 3 ba · 2,696 sqft
321 Alexzander Way, Winter Haven, FL
Joshua Nogowski · TAH FLORIDA LLC
29Active
$318,000
4 bd · 2 ba · 1,654 sqft
5148 Magnolia Preserve Blvd, Winter Haven, FL
Teneke Outing · LA ROSA REALTY CENTRAL FLORIDA LLC
Price Reduced29Active
$249,900
3 bd · 2 ba · 1,495 sqft
5308 Green Dr, Winter Haven, FL
Misty McCracken · FATHOM REALTY FL LLC
52Active
$449,900
3 bd · 2 ba · 2,069 sqft
1061 Sawgrass Dr, Winter Haven, FL
Barb Wiechmann · ROOST REALTY GROUP LLC
Price Reduced57Active
$110,000
2 bd · 2 ba · 1,056 sqft
4242 Cedarwood St, Winter Haven, FL
KATHY Devor · COLDWELL BANKER REALTY
21Active
$299,000
3 bd · 2 ba · 1,540 sqft
1104 Tyler Loop, Winter Haven, FL
Nick Whitehouse · RE/MAX PRIME PROPERTIES
Price Reduced39Active
$649,900
4 bd · 3 ba · 3,155 sqft
815 Lake Ned Rd, Winter Haven, FL
Barry Macchione · REMAX EXPERTS
34Active
$339,900
4 bd · 2 ba · 1,720 sqft
1738 Hummingbird Rd, Winter Haven, FL
Stephen Cline · DR HORTON REALTY OF CENTRAL FLORIDA LLC
Price Reduced55Active
$385,000
4 bd · 3 ba · 2,356 sqft
136 Lake Mariam Rd SE, Winter Haven, FL
Jill Baird, LLC · KELLER WILLIAMS ADVANTAGE III
32Active
$320,000
5 bd · 3 ba · 2,254 sqft
1454 Austin St, Winter Haven, FL
Carla Moreno Pineda · DALTON WADE INC
18Active
$92,000
2 bd · 2 ba · 840 sqft
1700 6th St NW #C21, Winter Haven, FL
Don Jerue · KELLER WILLIAMS REALTY SMART 1
Price Reduced19Active
$229,500
3 bd · 2 ba · 1,328 sqft
622 Crystals Blvd, Winter Haven, FL
Harrison Perez Collazo · CAISSA REALTY INVESTMENT INC
Price Reduced27Active
$226,990
3 bd · 3 ba · 1,423 sqft
3025 Captain Jax Way, Winter Haven, FL
Ben Goldstein · LENNAR REALTY

1…17 18 19…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.

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.

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)

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)