Winter Park, FL 55+ active adult communities & homes for sale - Page 59

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

5017 E FOUNTAINWOOD DR, ST CLOUD, FL, 34...

Community: Twin Lakes

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Questions? Call us: (888) 625-4885

Cindy Certified

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

$475,000

2 baths

1,510 sq ft

Townhouse

830 ALDENHAM LN, ORMOND BEACH, FL, 32174

13811 SE 85TH CIR, SUMMERFIELD, FL, 3449...

Community: Spruce Creek Country Club

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Questions? Call us: (888) 625-4885

The Villages®

110 CHULA VISTA AVE, LADY LAKE, FL, 3215..., Lady Lake, FL 32159

$400,000

3 beds

2 baths

2,038 sq ft

House

110 CHULA VISTA AVE, LADY LAKE, FL, 3215...

Community: The Villages®

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

Highland Lakes

26627 RACQUET CIR, LEESBURG, FL, 34748, Leesburg, FL 34748

$219,000

2 beds

2 baths

1,120 sq ft

Villa

26627 RACQUET CIR, LEESBURG, FL, 34748

Community: Highland Lakes

The Country Club of Mount Dora

2040 PARK FOREST BLVD, MOUNT DORA, FL, 3..., Mount Dora, FL 32757

$700,000

3 beds

3 baths

3,174 sq ft

House

2040 PARK FOREST BLVD, MOUNT DORA, FL, 3...

Community: The Country Club of Mount Dora

Del Webb Orlando

112 CASTELLON CT, DAVENPORT, FL, 33837, Davenport, FL 33837

$419,900

2 beds

2 baths

1,961 sq ft

House

112 CASTELLON CT, DAVENPORT, FL, 33837

Community: Del Webb Orlando

Cindy Certified

5256 MEADOW SONG DR, OKAHUMPKA, FL, 3476..., Okahumpka, FL 34762

$375,000

4 beds

2 baths

1,928 sq ft

19313 LOCHSIDE LN, MOUNT DORA, FL, 32757

Plantation Bay Golf & Country Club

732 ALDENHAM LN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$347,900

2 beds

2 baths

1,510 sq ft

Townhouse

732 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

Cresswind at Victoria Gardens

261 OLD MOSS CIR, DELAND, FL, 32724, Deland, FL 32724

$559,000

3 beds

3 baths

2,804 sq ft

House

261 OLD MOSS CIR, DELAND, FL, 32724

Community: Cresswind at Victoria Gardens

Trilogy® Orlando

184 CREPE MYRTLE DR, GROVELAND, FL, 3473..., Groveland, FL 34736

$519,000

4 beds

3 baths

3,044 sq ft

House

184 CREPE MYRTLE DR, GROVELAND, FL, 3473...

Community: Trilogy® Orlando

Arlington Ridge

26645 MANASSAS DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$450,000

3 beds

2 baths

2,236 sq ft

House

26645 MANASSAS DR, LEESBURG, FL, 34748

Community: Arlington Ridge

The Villages®

$270,000

2 beds

2 baths

1,160 sq ft

Villa

17403 SE 77TH SYCAMORE AVE, THE VILLAGES...

Community: The Villages®

The Villages®

108 N TIMBER TRL, WILDWOOD, FL, 34785, Wildwood, FL 34785

$119,900

2 beds

2 baths

1,232 sq ft

Manufactured Home

108 N TIMBER TRL, WILDWOOD, FL, 34785

Community: The Villages®

Cindy Certified

1727 SECOND ST, WINTER HAVEN, FL, 33881, Winter Haven, FL 33881

$260,000

3 beds

2 baths

1,470 sq ft

9230 SE 179TH WESLEY ST, THE VILLAGES, F...

Community: The Villages®

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Questions? Call us: (888) 625-4885

Plantation Bay Golf & Country Club

685 ALDENHAM LN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$599,999

4 beds

3 baths

2,496 sq ft

House

685 ALDENHAM LN, ORMOND BEACH, FL, 32174

Community: Plantation Bay Golf & Country Club

Gatherings of Lake Nona

7545 LAUREATE BLVD 7303, ORLANDO, FL, 32..., Orlando, FL 32827

$464,990

2 beds

2 baths

1,549 sq ft

Condo

7545 LAUREATE BLVD 7303, ORLANDO, FL, 32...

Community: Gatherings of Lake Nona

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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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2,698 homes

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Winter Park, FL 55+ active adult communities & homes for sale - Page 59

98 communities near Winter Park

2,698 homes near Winter Park

3 beds

2 baths

2,255 sq ft

House

3 beds

3 baths

2,006 sq ft

House

2 beds

2 baths

1,040 sq ft

House

2 beds

2 baths

1,644 sq ft

House

3 beds

2 baths

1,863 sq ft

House

4 beds

3 baths

1,974 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

3 beds

2 baths

1,684 sq ft

House

2 beds

2 baths

918 sq ft

Condo

3 beds

2 baths

1,703 sq ft

House

2 beds

2 baths

1,273 sq ft

House

3 beds

2 baths

1,713 sq ft

House

2 beds

2 baths

1,238 sq ft

Villa

3 beds

2 baths

1,823 sq ft

House

3 beds

2 baths

2,038 sq ft

House

4 beds

4 baths

3,324 sq ft

House

2 beds

2 baths

1,120 sq ft

Villa

3 beds