Winter Park, FL 55+ active adult communities & homes for sale - Page 50

2,698 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

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

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

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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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 (3 reviews)

Stonecrest

$200ks - $500ks

Stonecrest, Summerfield, FL

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

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.

5 rating (8 reviews)

Royal Highlands

$200ks - $400ks

Royal Highlands, Leesburg, FL

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

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)

Kings Ridge

$200ks - $400ks

Kings Ridge, Clermont, FL

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

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Questions? Call us: (888) 625-4885

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

Halifax Plantation

$300ks - $1Ms

Halifax Plantation, Ormond Beach, FL

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

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

5 rating (1 reviews)

Royal Harbor

$200ks - $800ks

Royal Harbor, Tavares, FL

Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 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 Country Club of Mount...

$200ks - $1Ms

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

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

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

Scottish Highlands

$100ks - $200ks

Scottish Highlands, Leesburg, FL

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

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Questions? Call us: (888) 625-4885

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)

Del Webb Sunbridge

$400ks - $800ks

Del Webb Sunbridge, St. Cloud, FL

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

Four Seasons at Orlando

$300ks - $600ks

Four Seasons at Orlando, Kissimmee, FL

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

Heritage - The Cottages o...

$300ks

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

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

Breakaway Trails

$400ks - $800ks

Breakaway Trails, Ormond Beach, FL

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

4.8 rating (6 reviews)

Highland Lakes

$100ks - $200ks

Highland Lakes, Leesburg, FL

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

Gatherings of Lake Nona

$300ks - $400ks

Gatherings of Lake Nona, Orlando, FL

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

Del Webb at Viera

$400ks - $1Ms

Del Webb at Viera, Melbourne, FL

New Construction | 55+ age-restricted | Built 2021 - present | 1,300 homes

Highland Fairways

$100ks - $300ks

Highland Fairways, Lakeland, FL

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

Lakeside Landings

$100ks - $300ks

Lakeside Landings, Oxford, FL

New and Resale | Age-targeted | Built 2005 - present | 700 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

1 rating (1 reviews)

Sullivan Ranch

$200ks - $500ks

Sullivan Ranch, Mount Dora, FL

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

1 2...3

Venetian Bay

3550 GRANDE TUSCANY WAY, NEW SMYRNA BEAC..., New Smyrna Beach, FL 32168

$799,900

4 beds

3 baths

2,592 sq ft

House

3550 GRANDE TUSCANY WAY, NEW SMYRNA BEAC...

Community: Venetian Bay

Cindy Certified

1138 SOLEWAY AVE, PALM BAY, FL, 32907, Palm Bay, FL 32907

$359,175

2 baths

1,148 sq ft

House

3561 COCHRAN ST, THE VILLAGES, FL, 32163

Community: The Villages®

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Questions? Call us: (888) 625-4885

The Villages®

$280,000

3 beds

2 baths

1,392 sq ft

House

9345 SE 177TH SIMONS LN, THE VILLAGES, F...

Community: The Villages®

The Villages®

$349,900

3 beds

2 baths

1,392 sq ft

House

1575 HOLLYBERRY PL, THE VILLAGES, FL, 32...

Community: The Villages®

Legacy of Leesburg

5351 AURORA DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$369,900

4 beds

4 baths

3,125 sq ft

House

5351 AURORA DR, LEESBURG, FL, 34748

Community: Legacy of Leesburg

Spruce Creek Country Club

12716 SE 91ST TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491

$399,000

3 beds

2 baths

2,128 sq ft

House

12716 SE 91ST TERRACE RD, SUMMERFIELD, F...

25 PEBBLE STONE LN, PALM COAST, FL, 3216...

Halifax Plantation

3319 NEWBLISS CIR, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174

$295,000

3 beds

2 baths

1,957 sq ft

House

3319 NEWBLISS CIR, ORMOND BEACH, FL, 321...

Community: Halifax Plantation

Kings Ridge

3605 WESTERHAM DR, CLERMONT, FL, 34711, Clermont, FL 34711

$316,500

3 beds

2 baths

1,572 sq ft

House

3605 WESTERHAM DR, CLERMONT, FL, 34711

Community: Kings Ridge

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

Questions? Call us: (888) 625-4885

Westhaven at Ovation - Townes Collection

12792 SUNSET WALK DR, WINTER GARDEN, FL,..., Winter Garden, FL 34787

$580,000

4 beds

3 baths

1,930 sq ft

Townhouse

12792 SUNSET WALK DR, WINTER GARDEN, FL,...

Community: Westhaven at Ovation - Townes Collection

The Villages®

$349,000

2 beds

2 baths

1,327 sq ft

Villa

587 AUDREY LN, THE VILLAGES, FL, 32162

Community: The Villages®

Del Webb Orlando

212 GRANADA LN, DAVENPORT, FL, 33837, Davenport, FL 33837

$403,900

3 beds

2 baths

1,568 sq ft

House

212 GRANADA LN, DAVENPORT, FL, 33837

Community: Del Webb Orlando

Alhambra Villas Condominiums

239 N HILL AVE 110, DELAND, FL, 32724, Deland, FL 32724

$190,000

2 beds

2 baths

1,091 sq ft

Condo

239 N HILL AVE 110, DELAND, FL, 32724

Community: Alhambra Villas Condominiums

Cindy Certified

1395 RILEY CIR, DELAND, FL, 32724, Deland, FL 32724

$349,900

3 beds

2 baths

1,511 sq ft

Community: The Villages®

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

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Westhaven at Ovation - Townes Collection

13861 EASDALE ALY, WINTER GARDEN, FL, 34..., Winter Garden, FL 34787

$499,000

4 beds

3 baths

2,031 sq ft

Townhouse

13861 EASDALE ALY, WINTER GARDEN, FL, 34...

Community: Westhaven at Ovation - Townes Collection

Westhaven at Ovation - Townes Collection

12808 SUNSET WALK DR, WINTER GARDEN, FL,..., Winter Garden, FL 34787

$539,000

4 beds

3 baths

1,897 sq ft

Townhouse

12808 SUNSET WALK DR, WINTER GARDEN, FL,...

Community: Westhaven at Ovation - Townes Collection

Indian River Colony Club

1531 TIPPICANOE CT, MELBOURNE, FL, 32940, Melbourne, FL 32940

$335,000

4 beds

3 baths

2,235 sq ft

House

1531 TIPPICANOE CT, MELBOURNE, FL, 32940

Community: Indian River Colony Club

The Villages®

$587,500

3 beds

2 baths

1,927 sq ft

House

1718 MEANS LN, THE VILLAGES, FL, 32162

Community: The Villages®

VillageWalk at Lake Nona

11800 ZELKOVA LN, ORLANDO, FL, 32827, Orlando, FL 32827

$715,000

3 beds

2 baths

2,005 sq ft

House

11800 ZELKOVA LN, ORLANDO, FL, 32827

Community: VillageWalk at Lake Nona

Legacy of Leesburg

27326 ORCHID GLADE ST, LEESBURG, FL, 347..., Leesburg, FL 34748

$290,000

3 beds

2 baths

1,480 sq ft

House

27326 ORCHID GLADE ST, LEESBURG, FL, 347...

Community: Legacy of Leesburg

The Villages®

116 CYPRESS RD, WILDWOOD, FL, 34785, Wildwood, FL 34785

$145,000

2 beds

2 baths

1,040 sq ft

Manufactured Home

116 CYPRESS RD, WILDWOOD, FL, 34785

Community: The Villages®

Cindy Certified

365 JYOTI DR, DAVENPORT, FL, 33837, Davenport, FL 33837

$330,000

4 beds

2 baths

1,821 sq ft

House

365 JYOTI DR, DAVENPORT, FL, 33837

Royal Harbor

5052 CHINA SEA DR, TAVARES, FL, 32778, Tavares, FL 32778

$313,000

3 beds

2 baths

1,613 sq ft

House

5052 CHINA SEA DR, TAVARES, FL, 32778

Community: Royal Harbor

Cindy Certified

1522 LAS PALMAS ST, LAKELAND, FL, 33810, Lakeland, FL 33810

$317,990

4 beds

2 baths

1,665 sq ft

House

1522 LAS PALMAS ST, LAKELAND, FL, 33810

Cindy Certified

988 VINEYARD RIDGE RD, MINNEOLA, FL, 347..., Minneola, FL 34715

$469,900

4 beds

2 baths

2,215 sq ft

House

988 VINEYARD RIDGE RD, MINNEOLA, FL, 347...

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

Questions? Call us: (888) 625-4885

Pennbrooke Fairways

420 GLEN ARBOR LN, LEESBURG, FL, 34748, Leesburg, FL 34748

$254,000

2 beds

2 baths

1,559 sq ft

Villa

420 GLEN ARBOR LN, LEESBURG, FL, 34748

Community: Pennbrooke Fairways

Cindy Certified

1013 SADIE RIDGE RD, CLERMONT, FL, 34715, Clermont, FL 34715

$444,500

4 beds

2 baths

1,846 sq ft

House

1013 SADIE RIDGE RD, CLERMONT, FL, 34715

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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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2,698 homes

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Winter Park, FL 55+ active adult communities & homes for sale - Page 50

98 communities near Winter Park

2,698 homes near Winter Park

4 beds

3 baths

2,592 sq ft

House

4 beds

2 baths

1,820 sq ft

House

2 beds

2 baths

1,530 sq ft

House

3 beds

2 baths

1,607 sq ft

House

2 beds

2 baths

1,148 sq ft

House

3 beds

2 baths

1,392 sq ft

House

3 beds

2 baths

1,392 sq ft

House

4 beds

4 baths

3,125 sq ft

House

3 beds

2 baths

2,128 sq ft

House

2 beds

2 baths

1,308 sq ft

House

3 beds

3 baths

1,995 sq ft

House

3 beds

2 baths

1,390 sq ft

House

2 beds

2 baths

1,908 sq ft

House

4 beds

2 baths

2,067 sq ft

House

3 beds

2 baths

1,957 sq ft

House

3 beds

2 baths

1,572 sq ft

House

4 beds

3 baths

1,930 sq ft

Townhouse

2 beds

2 baths

1,327 sq ft

Villa

3 beds

2 baths

1,568 sq ft

House

2 beds