Winter Park, FL 55+ active adult communities & homes for sale - Page 8

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

4.7 rating (18 reviews)

Solivita

$300ks - $700ks

Solivita, Kissimmee, FL

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

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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

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 (3 reviews)

Lake Ashton

$200ks - $500ks

Lake Ashton, Lake Wales, FL

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

5 rating (8 reviews)

Royal Highlands

$200ks - $400ks

Royal Highlands, Leesburg, FL

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

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

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Questions? Call us: (888) 625-4885

2.8 rating (6 reviews)

Arlington Ridge

$200ks - $500ks

Arlington Ridge, Leesburg, FL

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

Halifax Plantation

$300ks - $1Ms

Halifax Plantation, Ormond Beach, FL

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

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

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

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

The Country Club of Mount...

$200ks - $1Ms

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

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

Royal Harbor

$200ks - $800ks

Royal Harbor, Tavares, FL

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

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

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

Gatherings of Lake Nona

$300ks - $400ks

Gatherings of Lake Nona, Orlando, FL

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

Heritage - The Cottages o...

$300ks

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

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

The Timbers at Everlands

$200ks - $500ks

The Timbers at Everlands, Palm Bay, FL

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

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

Questions? Call us: (888) 625-4885

Four Seasons at Orlando

$300ks - $600ks

Four Seasons at Orlando, Kissimmee, FL

New Construction | 55+ age-restricted | Built 2017 - present | 557 homes

Colonnades

$100ks - $200ks

Colonnades, Lakeland, FL

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

32456 SEA LOCH LOOP, MOUNT DORA, FL, 327...

Highland Lakes

5606 ROSEWALL CIR, LEESBURG, FL, 34748, Leesburg, FL 34748

$307,500

3 beds

2 baths

2,040 sq ft

House

5606 ROSEWALL CIR, LEESBURG, FL, 34748

Community: Highland Lakes

Latitude Margaritaville

143 SALT SHAKER ST, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124

$464,900

2 beds

2 baths

1,563 sq ft

House

143 SALT SHAKER ST, DAYTONA BEACH, FL, 3...

House

8281 LAKE JAMES DR, LAKELAND, FL, 33810

Community: Lake James

Cindy Certified

60 PERROTTI LN, PALM COAST, FL, 32164, Palm Coast, FL 32164

$325,000

2 baths

1,592 sq ft

House

5105 HARBOUR DR, OXFORD, FL, 34484

Community: Lakeside Landings

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

Questions? Call us: (888) 625-4885

Esplanade at Highland Ranch

908 BRAEWOOD DR, CLERMONT, FL, 34715, Clermont, FL 34715

$633,000

3 beds

3 baths

2,396 sq ft

House

908 BRAEWOOD DR, CLERMONT, FL, 34715

Community: Esplanade at Highland Ranch

Spruce Creek South

9486 SE 173RD PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491

$239,400

2 beds

2 baths

1,008 sq ft

House

9486 SE 173RD PL, SUMMERFIELD, FL, 34491

Community: Spruce Creek South

Cindy Certified

132 BERGAMOT LOOP, DAVENPORT, FL, 33837, Davenport, FL 33837

$315,900

4 beds

2 baths

1,807 sq ft

5258 BEAR CORN RUN, PORT ORANGE, FL, 321...

The Villages®

$359,000

3 beds

2 baths

1,392 sq ft

Villa

1933 FIDDLEWOOD PL, THE VILLAGES, FL, 32...

Community: The Villages®

Esplanade at Highland Ranch

2666 STARGRASS CIR, CLERMONT, FL, 34715, Clermont, FL 34715

$535,000

2 beds

3 beds

2 baths

2,030 sq ft

House

478 DEL SOL AVE, DAVENPORT, FL, 33837

Villa

2339 SEBRING ST, THE VILLAGES, FL, 32162

Community: The Villages®

The Savannahs

4624 CALADIUM CIR, WEST MELBOURNE, FL, 3..., West Melbourne, FL 32904

$389,900

3 beds

2 baths

1,649 sq ft

House

4624 CALADIUM CIR, WEST MELBOURNE, FL, 3...

Community: The Savannahs

Cindy Certified

6444 MODERN DURAN DR, MELBOURNE, FL, 329..., Melbourne, FL 32940

$1,795,000

3 baths

2,366 sq ft

House

5561 MORANT BAY PATH, KISSIMMEE, FL, 347...

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

Questions? Call us: (888) 625-4885

Esplanade at Westview

4476 OCHOS RIOS PL, KISSIMMEE, FL, 34758, Kissimmee, FL 34758

$334,990

2 beds

2 baths

1,713 sq ft

House

4476 OCHOS RIOS PL, KISSIMMEE, FL, 34758

Community: Esplanade at Westview

The Villages®

$290,000

2 beds

2 baths

1,121 sq ft

Villa

746 ANGELITA AVE, THE VILLAGES, FL, 3215...

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.

Want more information about active adult communities around Winter Park?

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2,702 homes

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Winter Park, FL 55+ active adult communities & homes for sale - Page 8

98 communities near Winter Park

2,702 homes near Winter Park

2 beds

2 baths

1,813 sq ft

House

2 beds

2 baths

1,822 sq ft

House

4 beds

3 baths

1,790 sq ft

House

3 beds

2 baths

2,040 sq ft

House

2 beds

2 baths

1,563 sq ft

House

2 beds

2 baths

2,048 sq ft

House

2 beds

2 baths

1,309 sq ft

House

3 beds

2 baths

2,692 sq ft

House

2 beds

2 baths

1,186 sq ft

Villa

3 beds

2 baths

1,488 sq ft

House

3 beds

2 baths

1,774 sq ft

House

2 beds

2 baths

1,847 sq ft

House

4 beds

2 baths

1,862 sq ft

House

3 beds

2 baths

2,123 sq ft

House

3 beds

2 baths

1,945 sq ft

House

3 beds

2 baths

1,592 sq ft

House

3 beds

3 baths

2,396 sq ft

House

2 beds

2 baths

1,008 sq ft

House

4 beds

2 baths

1,807 sq ft

House

2 beds