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The buying timeline

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55 listings

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3 beds New construction With a pool

Waterfront Homes in Winter Haven, FL

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24 of 55 Listings

Map

24 of 55 Listings

Waterfront Homes in Winter Haven, FL — Page 2

55 listings

Waterfront Homes in Winter Haven, FL

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24 of 55 Listings

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Waterfront Homes in Winter Haven, FL

24 of 55 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Active

$149,900

2 bd · 2 ba · 1,190 sqft

700 Mirror Ter NW #511, Winter Haven, FL

David Small · KELLER WILLIAMS REALTY SMART 1

Price Reduced79Active

$520,000

4 bd · 4 ba · 2,118 sqft

1475 S Lake Howard Dr, Winter Haven, FL

Deanna Stone · THE STONES REAL ESTATE FIRM

52Active

$449,900

3 bd · 2 ba · 2,069 sqft

1061 Sawgrass Dr, Winter Haven, FL

Barb Wiechmann · ROOST REALTY GROUP LLC

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Price Reduced57Active

$310,000

3 bd · 2 ba · 2,109 sqft

3614 Plymouth Dr, Winter Haven, FL

Andrew Duncan · LPT REALTY LLC

Price Reduced23Active

$449,000

2 bd · 3 ba · 965 sqft

1620 17th St NW, Winter Haven, FL

Kimberly Saddler · LA ROSA REALTY PRESTIGE

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.

40Active

$119,000

2 bd · 2 ba · 1,190 sqft

700 Mirror Ter NW #506, Winter Haven, FL

Chris Goode · JUDY B CLEAVES PROPERTIES INC

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

21Active

$258,000

3 bd · 2 ba · 1,259 sqft

151 1st St, Winter Haven, FL

Milli Collins · MILLI REAL ESTATE SERVICES LLC

40Active

$164,900

2 bd · 2 ba · 1,351 sqft

700 Mirror Ter NW #507, Winter Haven, FL

Scott Kline · KLINE REAL ESTATE SERVICES

67Active

$1,195,000

5 bd · 6 ba · 3,235 sqft

250 Brigham Rd NW, Winter Haven, FL

David Small · KELLER WILLIAMS REALTY SMART 1

Price Reduced39Active

$299,900

4 bd · 3 ba · 2,526 sqft

5780 Lakeside Landings Blvd, Winter Haven, FL

Harley Holmes · KELLER WILLIAMS REALTY SMART 1

22Active

$169,500

2 bd · 2 ba · 1,252 sqft

702 Country Ln NE #702, Winter Haven, FL

Glenda Pruitt · FLORIDA HOME CHOICE REALTY

Price Reduced48Active

$290,000

3 bd · 2 ba · 1,711 sqft

6194 Grey Heron Dr, Winter Haven, FL

Amalia Lucena · TRUE FLORIDA REALTY LLC

38Active

$450,000

4 bd · 3 ba · 2,829 sqft

2734 Rochelle Dr, Winter Haven, FL

Roberta San Juan · GATAP REALTY

Price Reduced41Active

$299,900

3 bd · 2 ba · 1,728 sqft

136 Lake Ring Dr, Winter Haven, FL

Lamanda Jones · CENTURY 21 WATSON & MYERS REALTY

Price Reduced50Active

$410,000

3 bd · 3 ba · 1,828 sqft

900 Lake Jessie Dr, Winter Haven, FL

Patricia De Graaff, LLC · RE/MAX HERITAGE PROFESSIONALS

25Active

$125,000

2 bd · 2 ba · 960 sqft

1700 6th St NW #B23, Winter Haven, FL

Jean Julme · CENTRIC REALTY SERVICES LLC

47Active

$279,900

3 bd · 3 ba · 2,004 sqft

1502 NE Buckeye Rd NE #2, Winter Haven, FL

Joe Kuruvila · KURUVILA REALTY ASSOCIATES LLC

Price Reduced45Active

$284,950

3 bd · 2 ba · 1,517 sqft

265 Lake Thomas Dr, Winter Haven, FL

Angie Reynolds · PORCHLIGHT HOMES LLC

Price Reduced52Active

$450,000

4 bd · 2 ba · 2,385 sqft

183 Lake Thomas, Winter Haven, FL

Lucy Martinez · KELLER WILLIAMS REALTY SMART 1

Price Reduced42Active

$200,000

2 bd · 2 ba · 1,790 sqft

6825 S Lake Henry Dr NE, Winter Haven, FL

Patricia De Graaff, LLC · RE/MAX HERITAGE PROFESSIONALS

Price Reduced47Active

$660,000

4 bd · 3 ba · 2,790 sqft

124 Pangola Dr, Winter Haven, FL

Kelley Blackburn · COLDWELL BANKER REALTY

Price Reduced98Active

$649,900

4 bd · 3 ba · 2,397 sqft

3050 Crump Rd, Winter Haven, FL

Lisa Matheny · ENGEL & VOELKERS LAKELAND

1 2 3

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

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

Explore Winter Haven homes

By price

Homes Under $100K
Homes Under $200K
Homes Under $300K
Homes Under $400K

By bedrooms

2 Bedroom Homes
3 Bedroom Homes
4 Bedroom Homes
5 Bedroom Homes

By type

Single-Family Homes
Condos
Manufactured Homes

By feature

New Construction Homes
Homes with a Pool
Waterfront Homes
Foreclosures & Short Sales
55+ Community Homes

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.

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

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.