Winter Park, FL 55+ active adult communities & homes for sale - Page 52

2,702 homes near Winter Park

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4 rating (17 reviews)

The Villages®

$100ks - $1Ms

The Villages®, The Villages, FL

New and Resale | 55+ age-restricted | Built 1978 - present | 70,000 homes

Venetian Bay

$300ks - $1Ms

Venetian Bay, New Smyrna Beach, FL

New and Resale | Age-targeted | Built 2004 - present | 1,561 homes

4.5 rating (11 reviews)

Spruce Creek Country Club

$100ks - $400ks

Spruce Creek Country Club, Summerfield, FL

Resale Only | 55+ age-restricted | Built 1996 - 2007 | 3,250 homes

5 rating (2 reviews)

Plantation at Leesburg

$100ks - $300ks

Plantation at Leesburg, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1987 - 2008 | 2,820 homes

3.6 rating (48 reviews)

Latitude Margaritaville

$300ks - $800ks

Latitude Margaritaville, Daytona Beach, FL

Resale Only | 55+ age-restricted | Built 2017 - 2025 | 3,900 homes

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4.7 rating (18 reviews)

Solivita

$300ks - $700ks

Solivita, Kissimmee, FL

New and Resale | 55+ age-restricted | Built 2000 - present | 5,900 homes

5 rating (1 reviews)

Plantation Bay Golf &...

$400ks - $2Ms

Plantation Bay Golf &..., Ormond Beach, FL

New and Resale | Age-targeted | Built 1988 - present | 3,500 homes

5 rating (3 reviews)

Stonecrest

$200ks - $500ks

Stonecrest, Summerfield, FL

Resale Only | 55+ age-restricted | Built 1990 - 2024 | 2,224 homes

5 rating (3 reviews)

Twin Lakes

$200ks - $600ks

Twin Lakes, St. Cloud, FL

New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes

Pelican Bay Daytona Beach

$100ks - $600ks

Pelican Bay Daytona Beach, Daytona Beach, FL

Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 homes

Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.

Grand Haven

$200ks - $800ks

Grand Haven, Palm Coast, FL

New and Resale | Age-targeted | Built 1997 - present | 1,901 homes

5 rating (7 reviews)

Kings Ridge

$200ks - $400ks

Kings Ridge, Clermont, FL

Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 homes

3.8 rating (6 reviews)

Trilogy® Orlando

$200ks - $500ks

Trilogy® Orlando, Groveland, FL

Resale Only | 55+ age-restricted | Built 2005 - 2022 | 1,500 homes

5 rating (8 reviews)

Royal Highlands

$200ks - $400ks

Royal Highlands, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 homes

5 rating (3 reviews)

Lake Ashton

$200ks - $500ks

Lake Ashton, Lake Wales, FL

Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 homes

3.8 rating (4 reviews)

Spruce Creek South

$100ks - $200ks

Spruce Creek South, Summerfield, FL

Resale Only | 55+ age-restricted | Built 1989 - 1995 | 1,650 homes

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Questions? Call us: (888) 625-4885

4 rating (4 reviews)

Lakes of Mount Dora

$300ks - $900ks

Lakes of Mount Dora, Mount Dora, FL

New and Resale | 55+ age-restricted | Built 2006 - present | 950 homes

5 rating (1 reviews)

Sandpiper Golf & Coun...

$100ks - $300ks

Sandpiper Golf & Coun..., Lakeland, FL

New and Resale | 55+ age-restricted | Built 1985 - present | 1,193 homes

2.8 rating (6 reviews)

Arlington Ridge

$200ks - $500ks

Arlington Ridge, Leesburg, FL

New and Resale | 55+ age-restricted | Built 2005 - present | 629 homes

Halifax Plantation

$300ks - $1Ms

Halifax Plantation, Ormond Beach, FL

New and Resale | Age-targeted | Built 1980 - present | 1,000 homes

4 rating (2 reviews)

Harbor Hills Country Club

$300ks - $900ks

Harbor Hills Country Club, Lady Lake, FL

New and Resale | Age-targeted | Built 1989 - present | 940 homes

3.6 rating (5 reviews)

Heritage Hills

$200ks - $400ks

Heritage Hills, Clermont, FL

New and Resale | 55+ age-restricted | Built 2006 - present | 1,154 homes

5 rating (1 reviews)

Cresswind at Victoria Gar...

$300ks - $500ks

Cresswind at Victoria Gar..., DeLand, FL

Resale Only | 55+ age-restricted | Built 2001 - 2022 | 1,070 homes

The Country Club of Mount...

$200ks - $1Ms

The Country Club of Mount..., Mount Dora, FL

Resale Only | Age-targeted | Built 1991 - 2005 | 827 homes

Highland Fairways

$100ks - $300ks

Highland Fairways, Lakeland, FL

Resale Only | 55+ age-restricted | Built 1983 - 1998 | 660 homes

Breakaway Trails

$400ks - $800ks

Breakaway Trails, Ormond Beach, FL

New and Resale | Age-targeted | Built 1985 - present | 976 homes

5 rating (1 reviews)

Royal Harbor

$200ks - $800ks

Royal Harbor, Tavares, FL

Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 homes

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Questions? Call us: (888) 625-4885

5 rating (8 reviews)

Pennbrooke Fairways

<$100k - $300ks

Pennbrooke Fairways, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 homes

5 rating (1 reviews)

Del Webb Sunbridge

$400ks - $800ks

Del Webb Sunbridge, St. Cloud, FL

New and Resale | 55+ age-restricted | Built 2019 - present | 1,300 homes

Heritage - The Cottages o...

$300ks

Heritage - The Cottages o..., Okahumpka, FL

New Construction | 55+ age-restricted | Built 2022 - present | 179 homes

Gatherings of Lake Nona

$300ks - $400ks

Gatherings of Lake Nona, Orlando, FL

New and Resale | 55+ age-restricted | Built 2017 - present | 216 homes

4.8 rating (6 reviews)

Highland Lakes

$100ks - $200ks

Highland Lakes, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes

1 rating (1 reviews)

Sullivan Ranch

$200ks - $500ks

Sullivan Ranch, Mount Dora, FL

Resale Only | 55+ age-restricted | Built 2005 - 2020 | 692 homes

4.4 rating (16 reviews)

Del Webb Orlando

$200ks - $500ks

Del Webb Orlando, Davenport, FL

Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes

Foxwood Lake Estates

$100ks - $200ks

Foxwood Lake Estates, Lakeland, FL

Resale Only | 55+ age-restricted | Built 1982 - 1987 | 545 homes

5 rating (1 reviews)

Legacy of Leesburg

$200ks - $400ks

Legacy of Leesburg, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1999 - 2017 | 1,000 homes

5 rating (1 reviews)

VillageWalk at Lake Nona

$300ks - $700ks

VillageWalk at Lake Nona, Orlando, FL

Resale Only | Age-targeted | Built 2006 - 2016 | 1,300 homes

The Timbers at Everlands

$200ks - $500ks

The Timbers at Everlands, Palm Bay, FL

New Construction | 55+ age-restricted | Built 2023 - present | 450 homes

Want to learn more about 55+ communities in Winter Park? 55places can help!

Questions? Call us: (888) 625-4885

The Lakes at Harmony

$200ks - $400ks

The Lakes at Harmony, Harmony, FL

New and Resale | 55+ age-restricted | Built 2016 - present | 400 homes

Colonnades

$100ks - $200ks

Colonnades, Lakeland, FL

Resale Only | 55+ age-restricted | Built 1985 - 1994 | 360 homes

3859 SANIBEL ST, CLERMONT, FL, 34711

Community: Heritage Hills

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Questions? Call us: (888) 625-4885

Heritage Hills

3752 QUAINT LN, CLERMONT, FL, 34711, Clermont, FL 34711

$399,900

3 beds

3 baths

2,006 sq ft

House

3752 QUAINT LN, CLERMONT, FL, 34711

Community: Heritage Hills

The Villages®

$795,000

3 beds

2 baths

2,061 sq ft

House

5495 HAWKINS DR, THE VILLAGES, FL, 32163

Community: The Villages®

Cindy Certified

21 POSTMAN LN, PALM COAST, FL, 32164, Palm Coast, FL 32164

$391,971

4 beds

2 baths

1,873 sq ft

830 ALDENHAM LN, ORMOND BEACH, FL, 32174

Community: Plantation Bay Golf & Country Club

Want to learn more about 55+ communities in Winter Park? 55places can help!

Questions? Call us: (888) 625-4885

Latitude Margaritaville

852 CORAL REEF WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124

$539,000

2 beds

3 baths

1,748 sq ft

House

852 CORAL REEF WAY, DAYTONA BEACH, FL, 3...

Community: Latitude Margaritaville

Trilogy® Orlando

108 MIST FLOWER LN, GROVELAND, FL, 34736, Groveland, FL 34736

$440,000

2 beds

2 baths

1,900 sq ft

House

108 MIST FLOWER LN, GROVELAND, FL, 34736

Community: Trilogy® Orlando

Summit Chase Villas

12449 ORANGEWOOD CIR 17, TAVARES, FL, 32..., Tavares, FL 32778

$174,900

2 beds

2 baths

918 sq ft

Condo

12449 ORANGEWOOD CIR 17, TAVARES, FL, 32...

Community: Summit Chase Villas

Summit Greens

2197 CALEDONIAN ST, CLERMONT, FL, 34711, Clermont, FL 34711

$334,900

3 beds

2 baths

1,703 sq ft

House

2197 CALEDONIAN ST, CLERMONT, FL, 34711

Community: Summit Greens

Lake Henry Estates

558 PINNACLE DR, HAINES CITY, FL, 33844, Haines City, FL 33844

$253,000

2 beds

2 baths

1,273 sq ft

House

558 PINNACLE DR, HAINES CITY, FL, 33844

Community: Lake Henry Estates

Kings Ridge

3828 AVON CT, CLERMONT, FL, 34711, Clermont, FL 34711

$395,000

3 beds

2 baths

2,026 sq ft

House

3828 AVON CT, CLERMONT, FL, 34711

Community: Kings Ridge

Arlington Ridge

27118 ROANOKE DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$364,900

3 beds

2 baths

1,713 sq ft

House

27118 ROANOKE DR, LEESBURG, FL, 34748

Community: Arlington Ridge

Spruce Creek Country Club

14160 SE 85TH AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$225,000

2 beds

2 baths

1,238 sq ft

Villa

14160 SE 85TH AVE, SUMMERFIELD, FL, 3449...

Community: Spruce Creek Country Club

Stonecrest

17867 SE 115TH CIR, SUMMERFIELD, FL, 344..., Summerfield, FL 34491

$299,000

3 beds

2 baths

1,597 sq ft

House

17867 SE 115TH CIR, SUMMERFIELD, FL, 344...

Community: Stonecrest

Cindy Certified

378 HAMMOCK OAKS BLVD, LADY LAKE, FL, 32..., Lady Lake, FL 32159

$297,990

3 beds

2 baths

1,549 sq ft

House

378 HAMMOCK OAKS BLVD, LADY LAKE, FL, 32...

The Villages®

$268,000

2 beds

2 baths

1,160 sq ft

Villa

17431 SE 93RD RETFORD TER, THE VILLAGES,...

Community: The Villages®

Want to learn more about 55+ communities in Winter Park? 55places can help!

Questions? Call us: (888) 625-4885

Solivita

1309 LOMBARDI CT, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$280,000

2 beds

2 baths

1,366 sq ft

House

1309 LOMBARDI CT, KISSIMMEE, FL, 34759

Community: Solivita

Cindy Certified

3030 RUBY FALLS DR, DELAND, FL, 32727, Deland, FL 32727

$325,000

2 baths

2,134 sq ft

House

41 PINE CIR, PALM COAST, FL, 32164

Want to learn more about 55+ communities in Winter Park? 55places can help!

Questions? Call us: (888) 625-4885

Halifax Plantation

4105 PIUTE LN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$1,174,900

4 beds

4 baths

3,324 sq ft

House

4105 PIUTE LN, ORMOND BEACH, FL, 32174

Community: Halifax Plantation

The Villages®

508 SAINT ANDREWS BLVD, LADY LAKE, FL, 3..., Lady Lake, FL 32159

$253,900

2 beds

2 baths

1,532 sq ft

Manufactured Home

508 SAINT ANDREWS BLVD, LADY LAKE, FL, 3...

Community: The Villages®

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Frequently Asked Questions

What size 55+ communities are there in Winter Park?

In Winter Park, there is 1 small community with less than 500 homes.

How many homes are there in the smallest, largest, and average 55+ communities in Winter Park?

The smallest 55+ community in Winter Park has 178 homes, the largest has 178 homes, and the average community consists of 178 homes.

Are there new 55+ homes available in Winter Park?

Yes, there is new 55+ home available in Winter Park. The most recent community started in Winter Park include Rosalia Winter Park. There is also 1 community in Winter Park that offers new construction homes, including Rosalia Winter Park.

Are there gated 55+ communities in Winter Park?

Yes, there is gated 55+ community in Winter Park. The only 55+ community in Winter Park is gated. For instance, Rosalia Winter Park is a gated community with 178 homes.

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2,702 homes

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Winter Park, FL 55+ active adult communities & homes for sale - Page 52

98 communities near Winter Park

2,702 homes near Winter Park

2 beds

2 baths

1,289 sq ft

House

3 beds

2 baths

2,255 sq ft

House

3 beds

2 baths

1,910 sq ft

House

2 beds

2 baths

1,102 sq ft

Villa

3 beds

3 baths

2,554 sq ft

House

3 beds

3 baths

2,006 sq ft

House

3 beds

2 baths

2,061 sq ft

House

4 beds

2 baths

1,873 sq ft

House

3 beds

2 baths

1,684 sq ft

Villa

2 beds

2 baths

1,040 sq ft

House

2 beds

2 baths

1,144 sq ft

Modular

2 beds

2 baths

1,644 sq ft

House

3 beds

2 baths

1,863 sq ft

House

3 beds

2 baths

1,550 sq ft

House

2 beds

2 baths

1,306 sq ft

House

2 beds

2 baths

1,510 sq ft

Townhouse

2 beds

3 baths

1,748 sq ft

House

2 beds

2 baths

1,900 sq ft

House

2 beds

2 baths

918 sq ft

Condo

3 beds