55+ Community Homes in Winter Haven, FL

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24 of 125 Listings

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24 of 125 Listings

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125 listings

55+ Community Homes in Winter Haven, FL

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24 of 125 Listings

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55+ Community Homes in Winter Haven, FL

24 of 125 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

New66

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Active

$310,000

3 bd · 2 ba · 1,680 sqft

5344 Nicklaus Dr, Winter Haven, FL

Lori Raath · LAKE ASHTON REALTY INC.

New17Active

$249,900

2 bd · 2 ba · 1,719 sqft

4035 Carteret Dr, Winter Haven, FL

Bryan Rhoads · LKV REALTY, LLC

72Active

$434,700

3 bd · 2 ba · 2,312 sqft

1321 Oakmont Dr, Winter Haven, FL

Lori Raath · LAKE ASHTON REALTY INC.

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

35Active

$149,900

3 bd · 3 ba · 1,622 sqft

100 El Camino Dr #301, Winter Haven, FL

Craig Burke · CRAIG BURKE REAL ESTATE GROUP, LLC

90Active

$279,900

3 bd · 2 ba · 1,495 sqft

5281 Pebble Beach Blvd, Winter Haven, FL

Brad Kirwan · GLOBAL LIFESTYLE LLC

75Active

$449,900

3 bd · 2 ba · 2,354 sqft

4064 Phoenician Way, Winter Haven, FL

Lori Raath · LAKE ASHTON REALTY INC.

34Active

$190,500

2 bd · 2 ba · 1,231 sqft

1631 Linz Ct, Winter Haven, FL

Pat Pearson · VIEWPOINT VALUE REALTY

53Active

$349,001

2 bd · 2 ba · 1,888 sqft

4075 Bedford Ave, Winter Haven, FL

Eileen Belanger · CENTURY 21 MYERS REALTY LAKE WALES

56Active

$350,000

3 bd · 3 ba · 2,006 sqft

3541 Raleigh Dr, Winter Haven, FL

Eileen Belanger · CENTURY 21 MYERS REALTY LAKE WALES

Price Reduced99Active

$359,500

3 bd · 2 ba · 1,833 sqft

5325 Snead Dr, Winter Haven, FL

Francis Alvarez Lopez · LA ROSA REALTY LLC

32Active

$165,000

2 bd · 2 ba · 1,014 sqft

6204 Knotty Pine Dr SE, Winter Haven, FL

Susan Brown · COLDWELL BANKER REALTY

34Active

$79,500

2 bd · 2 ba · 989 sqft

97 Parson Dr, Winter Haven, FL

Chris Cain · MOSAIC SERVICES LLC

35Active

$215,000

2 bd · 2 ba · 1,143 sqft

6364 Lolly Bay Loop NE, Winter Haven, FL

Daniel Betancourt · EXP REALTY LLC

Open house Sat, Oct 17 · 10:00 AM90Active

$549,999

3 bd · 3 ba · 2,682 sqft

6136 Pebble Beach Blvd, Winter Haven, FL

Lori Raath · LAKE ASHTON REALTY INC.

Price Reduced39Active

$98,500

2 bd · 2 ba · 1,347 sqft

1776 6th St NW #304, Winter Haven, FL

Chris Goode · JUDY B CLEAVES PROPERTIES INC

27Active

$184,900

2 bd · 2 ba · 1,436 sqft

2215 Starboard Dr #29, Winter Haven, FL

Scott Kline · KLINE REAL ESTATE SERVICES

32Active

$145,000

3 bd · 2 ba · 1,226 sqft

333 Lake Howard Dr NW #204D, Winter Haven, FL

Milena Phan · UNITED REAL ESTATE PREFERRED

41Active

$175,000

2 bd · 2 ba · 1,340 sqft

6107 Grand Oaks Dr SE, Winter Haven, FL

Anita Lowe · LOCKHART & ASSOCIATES INC

44Active

$134,990

1 bd · 1 ba · 481 sqft

7060 Fairview Village Cir, Winter Haven, FL

AJ Alvarez · LPT REALTY, LLC

25Active

$152,000

2 bd · 2 ba · 1,144 sqft

6455 Hollyberry Ln NE, Winter Haven, FL

Harrison Perez Collazo · CAISSA REALTY INVESTMENT INC

Price Reduced12Active

$99,000

2 bd · 2 ba · 1,030 sqft

333 Lake Howard Dr NW #302B, Winter Haven, FL

Karen Myers · UNITED REALTY GROUP INC

52Active

$198,000

2 bd · 2 ba · 1,856 sqft

6627 Westchester Dr NE, Winter Haven, FL

Patricia De Graaff, LLC · RE/MAX HERITAGE PROFESSIONALS

40Active

$220,000

2 bd · 2 ba · 1,664 sqft

6600 Scenic Point Dr SE, Winter Haven, FL

Anita Lowe · LOCKHART & ASSOCIATES INC

35Active

$179,000

2 bd · 2 ba · 1,248 sqft

6458 Hollyberry Ln NE, Winter Haven, FL

Harrison Perez Collazo · CAISSA REALTY INVESTMENT INC

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 100.0% of asking price

Sales here are closing essentially at asking. MLS · 118 sales · as of Sep 29, 2026

Homes that sold · County records, as of Sep 15, 2026

Median sale price: $266,900$198,500–$329,995 typical range
Price per sq. ft.: $160
Sales: 111
Paid in cash: 38.7%

Homes on the market · MLS, as of Sep 27, 2026–Sep 29, 2026

Median list price: $294,400
Homes for sale: 762
Median days on market: 49 days

Price trend · Assessor repeat sales, as of Sep 30, 2026

Year-over-year: -20.9%

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

Explore Winter Haven homes

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 100.0% of asking price

Sales here are closing essentially at asking. MLS · 118 sales · as of Sep 29, 2026

Homes that sold · County records, as of Sep 15, 2026

Median sale price: $266,900$198,500–$329,995 typical range
Price per sq. ft.: $160
Sales: 111
Paid in cash: 38.7%

Homes on the market · MLS, as of Sep 27, 2026–Sep 29, 2026

Median list price: $294,400
Homes for sale: 762
Median days on market: 49 days

Price trend · Assessor repeat sales, as of Sep 30, 2026

Year-over-year: -20.9%

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.

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Your local brokerage

Your local brokerage

Your local brokerage

Listing data & MLS disclosures

Winter Haven housing market

Homes that sold · County records, as of Sep 15, 2026

Homes on the market · MLS, as of Sep 27, 2026–Sep 29, 2026

Price trend · Assessor repeat sales, as of Sep 30, 2026

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 11, 2026

Winter Haven, FL community profile

Explore Winter Haven homes

Your local brokerage

Listing data & MLS disclosures

Winter Haven, FL community profile

Winter Haven housing market

Homes that sold · County records, as of Sep 15, 2026

Homes on the market · MLS, as of Sep 27, 2026–Sep 29, 2026

Price trend · Assessor repeat sales, as of Sep 30, 2026

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 11, 2026