Winter Park, FL 55+ active adult communities & homes for sale - Page 9

2,259 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

4.7 rating (18 reviews)

Solivita

$300ks - $700ks

Solivita, Kissimmee, FL

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

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

Venetian Bay

$300ks - $1Ms

Venetian Bay, New Smyrna Beach, FL

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

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Questions? Call us: (888) 625-4885

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

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)

Lake Ashton

$200ks - $500ks

Lake Ashton, Lake Wales, FL

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

Grand Haven

$200ks - $800ks

Grand Haven, Palm Coast, FL

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

Halifax Plantation

$300ks - $1Ms

Halifax Plantation, Ormond Beach, FL

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

5 rating (8 reviews)

Royal Highlands

$200ks - $400ks

Royal Highlands, Leesburg, FL

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

Pelican Bay Daytona Beach

$100ks - $600ks

Pelican Bay Daytona Beach, Daytona Beach, FL

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

3.8 rating (6 reviews)

Trilogy® Orlando

$200ks - $500ks

Trilogy® Orlando, Groveland, FL

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

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Questions? Call us: (888) 625-4885

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

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 (4 reviews)

Spruce Creek South

$100ks - $200ks

Spruce Creek South, Summerfield, FL

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

5 rating (1 reviews)

Cresswind at Victoria Gar...

$200ks - $500ks

Cresswind at Victoria Gar..., DeLand, FL

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

Breakaway Trails

$400ks - $800ks

Breakaway Trails, Ormond Beach, FL

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

5 rating (1 reviews)

Royal Harbor

$200ks - $800ks

Royal Harbor, Tavares, FL

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

1 rating (1 reviews)

Sullivan Ranch

$200ks - $500ks

Sullivan Ranch, Mount Dora, FL

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

4.8 rating (6 reviews)

Highland Lakes

$100ks - $200ks

Highland Lakes, Leesburg, FL

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

Summer Trees

$200ks - $400ks

Summer Trees, Port Orange, FL

Resale Only | 55+ age-restricted | Built 1976 - 2005 | 500 homes

5 rating (8 reviews)

Pennbrooke Fairways

<$100k - $300ks

Pennbrooke Fairways, Leesburg, FL

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

The Lakes at Harmony

$200ks - $400ks

The Lakes at Harmony, Harmony, FL

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

The Country Club of Mount...

$200ks - $1Ms

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

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

Foxwood Lake Estates

$100ks - $200ks

Foxwood Lake Estates, Lakeland, FL

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

5 rating (2 reviews)

Bridgewater at Viera

$300ks - $800ks

Bridgewater at Viera, Melbourne, FL

Resale Only | 55+ age-restricted | Built 2017 - 2023 | 870 homes

Gatherings of Lake Nona

$300ks - $400ks

Gatherings of Lake Nona, Orlando, FL

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

4.4 rating (16 reviews)

Del Webb Orlando

$200ks - $500ks

Del Webb Orlando, Davenport, FL

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

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

Scottish Highlands

$100ks - $200ks

Scottish Highlands, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1983 - 1992 | 653 homes

2107 GREENLAW CT, LEESBURG, FL, 34788

Community: Scottish Highlands

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Questions? Call us: (888) 625-4885

The Villages®

$599,500

3 beds

2 baths

2,044 sq ft

House

16815 SE 85TH BELKNAP AVE, THE VILLAGES,...

Community: The Villages®

The Savannahs

3984 CALADIUM CIR, WEST MELBOURNE, FL, 3..., West Melbourne, FL 32904

$439,900

4 beds

2 baths

2,050 sq ft

House

3984 CALADIUM CIR, WEST MELBOURNE, FL, 3...

Community: The Savannahs

Solivita

518 DAVINCI PASS, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$346,000

2 beds

2 baths

1,491 sq ft

House

518 DAVINCI PASS, KISSIMMEE, FL, 34759

Community: Solivita

The Villages®

$300,000

2 beds

2 baths

1,160 sq ft

Villa

16933 SE 94TH SUNNYBROOK CIR, THE VILLAG...

Community: The Villages®

Sandpiper Golf & Country Club

6121 KITTIWAKE DR, LAKELAND, FL, 33809, Lakeland, FL 33809

$248,000

2 beds

2 baths

1,135 sq ft

House

6121 KITTIWAKE DR, LAKELAND, FL, 33809

Community: Sandpiper Golf & Country Club

Lake Ashton

5337 HOGAN LN, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884

$355,000

3 beds

2 baths

1,833 sq ft

House

5337 HOGAN LN, WINTER HAVEN, FL, 33884

Community: Lake Ashton

The Villages®

$414,900

3 beds

2 baths

1,668 sq ft

House

640 MALLORY HILL DR, THE VILLAGES, FL, 3...

Community: The Villages®

Twin Lakes

2665 MEADOWEDGE LOOP, ST CLOUD, FL, 3477..., St Cloud, FL 34772

$549,700

3 beds

3 baths

2,362 sq ft

House

2665 MEADOWEDGE LOOP, ST CLOUD, FL, 3477...

Community: Twin Lakes

The Villages®

$307,900

2 beds

2 baths

1,156 sq ft

Villa

2348 RILEY RD, THE VILLAGES, FL, 32162

Community: The Villages®

Del Webb Sunbridge

2542 CLIFF WAY, ST CLOUD, FL, 34771, St Cloud, FL 34771

$329,000

2 beds

2 baths

1,584 sq ft

House

2542 CLIFF WAY, ST CLOUD, FL, 34771

Community: Del Webb Sunbridge

The Villages®

$2,750,000

3 beds

5 baths

5,904 sq ft

House

1792 LAKE MIONA DR, THE VILLAGES, FL, 32...

Community: The Villages®

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Questions? Call us: (888) 625-4885

The Villages®

$347,500

3 beds

2 baths

1,361 sq ft

House

6128 SKINNER ST, THE VILLAGES, FL, 32163

Community: The Villages®

Spruce Creek South

10358 SE 178 PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491

$214,900

2 beds

2 baths

1,260 sq ft

House

10358 SE 178 PL, SUMMERFIELD, FL, 34491

Community: Spruce Creek South

Latitude Margaritaville

213 CHEESEBURGER DR, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124

$517,900

2 beds

2 baths

1,681 sq ft

House

213 CHEESEBURGER DR, DAYTONA BEACH, FL, ...

Community: Latitude Margaritaville

Halifax Plantation

3645 CHRISTA CT, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$639,900

3 beds

2 baths

2,279 sq ft

House

3645 CHRISTA CT, ORMOND BEACH, FL, 32174

Community: Halifax Plantation

Grand Haven

6 SCARLET OAK CIR, PALM COAST, FL, 32137, Palm Coast, FL 32137

$829,000

3 beds

3 baths

2,465 sq ft

House

6 SCARLET OAK CIR, PALM COAST, FL, 32137

Community: Grand Haven

Gatherings of Lake Nona

7505 LAUREATE BLVD 2206, ORLANDO, FL, 32..., Orlando, FL 32827

$420,000

2 beds

2 baths

1,549 sq ft

Condo

7505 LAUREATE BLVD 2206, ORLANDO, FL, 32...

Community: Gatherings of Lake Nona

Grand Haven

15 TANGLEWOOD CT, PALM COAST, FL, 32137, Palm Coast, FL 32137

$429,000

3 beds

2 baths

1,508 sq ft

House

15 TANGLEWOOD CT, PALM COAST, FL, 32137

Community: Grand Haven

The Villages®

$655,000

3 beds

2 baths

2,533 sq ft

House

8755 SE 177TH GRASSMERE ST, THE VILLAGES...

Community: The Villages®

VillageWalk at Lake Nona

12077 ULETA LN, ORLANDO, FL, 32827, Orlando, FL 32827

$919,000

5 beds

4 baths

4,036 sq ft

House

12077 ULETA LN, ORLANDO, FL, 32827

Community: VillageWalk at Lake Nona

Gatherings of Lake Nona

7521 LAUREATE BLVD 5307, ORLANDO, FL, 32..., Orlando, FL 32827

$524,900

3 beds

2 baths

1,799 sq ft

Condo

7521 LAUREATE BLVD 5307, ORLANDO, FL, 32...

Community: Gatherings of Lake Nona

Halifax Plantation

3093 ADRIAN DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$699,990

4 beds

3 baths

2,100 sq ft

House

3093 ADRIAN DR, ORMOND BEACH, FL, 32174

House

5384 AURORA DR, LEESBURG, FL, 34748

Community: Legacy of Leesburg

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

Questions? Call us: (888) 625-4885

Baytree

$299,900

3 beds

3 baths

1,581 sq ft

Townhouse

136 BAYTREE BLVD, TAVARES, FL, 32778

Community: Baytree

Tohoqua Reserve

1974 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744

$450,000

3 beds

3 baths

2,175 sq ft

House

1974 SPRING SHOWER CIR, KISSIMMEE, FL, 3...

Community: Tohoqua Reserve

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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.

Want more information about active adult communities around Winter Park?

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2,259 homes

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Winter Park, FL 55+ active adult communities & homes for sale - Page 9

95 communities near Winter Park

2,259 homes near Winter Park

3 beds

2 baths

1,954 sq ft

House

2 beds

3 baths

2,163 sq ft

House

2 beds

2 baths

1,703 sq ft

House

3 beds

3 baths

2,212 sq ft

House

2 beds

2 baths

1,438 sq ft

House

3 beds

2 baths

2,044 sq ft

House

4 beds

2 baths

2,050 sq ft

House

2 beds

2 baths

1,491 sq ft

House

2 beds

2 baths

1,160 sq ft

Villa

2 beds

2 baths

1,135 sq ft

House

3 beds

2 baths

1,833 sq ft

House

3 beds

2 baths

1,668 sq ft

House

3 beds

3 baths

2,362 sq ft

House

2 beds

2 baths

1,156 sq ft

Villa

2 beds

2 baths

1,584 sq ft

House

3 beds

5 baths

5,904 sq ft

House

3 beds

2 baths

1,361 sq ft

House

2 beds

2 baths

1,260 sq ft

House

2 beds

2 baths

1,681 sq ft

House

3 beds