Winter Park, FL 55+ active adult communities & homes for sale - Page 15

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

3164 NAMASTE DR, CLERMONT, FL, 34714

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Cindy Certified

1636 WILSON PRAIRIE CIR, GROVELAND, FL, ..., Groveland, FL 34736

$465,000

2 baths

1,894 sq ft

House

209 LONG WAVE WAY, GROVELAND, FL, 34736

Cindy Certified

370 FREE RANGE DR, GROVELAND, FL, 34736, Groveland, FL 34736

$472,990

4 beds

3 baths

1,894 sq ft

House

370 FREE RANGE DR, GROVELAND, FL, 34736

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

Questions? Call us: (888) 625-4885

Cindy Certified

2393 PANORAMIC CIR, APOPKA, FL, 32703, Apopka, FL 32703

$560,000

4 beds

3 baths

2,510 sq ft

House

2393 PANORAMIC CIR, APOPKA, FL, 32703

The Villages®

$439,000

3 beds

2 baths

1,617 sq ft

Villa

1068 BECKER AVE, THE VILLAGES, FL, 32163

Community: The Villages®

Cindy Certified

3019 SANCTUARY DR, CLERMONT, FL, 34714, Clermont, FL 34714

$499,999

2 baths

1,806 sq ft

House

61 PRATTWOOD LN, PALM COAST, FL, 32164

Cindy Certified

2938 SCARLETT DR, ST CLOUD, FL, 34772, St Cloud, FL 34772

$430,000

4 beds

3 baths

1,854 sq ft

House

2938 SCARLETT DR, ST CLOUD, FL, 34772

Spruce Creek Country Club

9605 SE 136TH PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491

$389,900

3 beds

2 baths

2,335 sq ft

House

9605 SE 136TH PL, SUMMERFIELD, FL, 34491

Community: Spruce Creek Country Club

Cindy Certified

6072 BALANCE WAY, CLERMONT, FL, 34714, Clermont, FL 34714

$449,990

4 beds

3 baths

1,823 sq ft

House

6072 BALANCE WAY, CLERMONT, FL, 34714

Venetian Bay

110 PORTOFINO BLVD, NEW SMYRNA BEACH, FL..., New Smyrna Beach, FL 32168

$1,100,000

3 beds

3 baths

2,669 sq ft

House

110 PORTOFINO BLVD, NEW SMYRNA BEACH, FL...

Community: Venetian Bay

Cindy Certified

6183 GREY HERON DR, WINTER HAVEN, FL, 33..., Winter Haven, FL 33881

$339,999

5 beds

4 baths

1,872 sq ft

House

6183 GREY HERON DR, WINTER HAVEN, FL, 33...

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

Questions? Call us: (888) 625-4885

Plantation at Leesburg

24215 BELLE MEDE DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$417,500

3 beds

3 baths

2,755 sq ft

House

24215 BELLE MEDE DR, LEESBURG, FL, 34748

Community: Plantation at Leesburg

Legacy of Leesburg

27303 GINGERBREAD PL, LEESBURG, FL, 3474..., Leesburg, FL 34748

$388,790

3 beds

3 baths

2,287 sq ft

House

27303 GINGERBREAD PL, LEESBURG, FL, 3474...

Community: Legacy of Leesburg

The Villages®

$1,400,000

3 beds

2 baths

3,478 sq ft

House

1793 HARTFORD PATH, THE VILLAGES, FL, 32...

Community: The Villages®

Sullivan Ranch

30412 TOKARA TER, MOUNT DORA, FL, 32757, Mount Dora, FL 32757

$630,000

4 beds

3 baths

3,886 sq ft

House

30412 TOKARA TER, MOUNT DORA, FL, 32757

Community: Sullivan Ranch

Tohoqua Reserve

2723 SUMMER RETREAT LN, KISSIMMEE, FL, 3..., Kissimmee, FL 34744

$308,000

2 beds

2 baths

1,559 sq ft

Villa

2723 SUMMER RETREAT LN, KISSIMMEE, FL, 3...

Community: Tohoqua Reserve

The Villages®

1314 TEAKWOOD LN, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$134,900

2 beds

1 baths

720 sq ft

Mobile Home

1314 TEAKWOOD LN, LADY LAKE, FL, 32159

5825 FLINT LOOP, THE VILLAGES, FL, 32163

Community: The Villages®

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

Questions? Call us: (888) 625-4885

The Villages®

$319,900

3 beds

2 baths

1,404 sq ft

House

7169 SE 172ND HAZELWOOD LOOP, THE VILLAG...

Community: The Villages®

Arlington Ridge

4400 BEDFORD WAY, LEESBURG, FL, 34748, Leesburg, FL 34748

$294,900

2 beds

2 baths

1,632 sq ft

Villa

4400 BEDFORD WAY, LEESBURG, FL, 34748

Community: Arlington Ridge

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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 15

98 communities near Winter Park

2,698 homes near Winter Park

3 beds

2 baths

1,856 sq ft

House

3 beds

2 baths

1,868 sq ft

House

2 beds

2 baths

1,968 sq ft

House

3 beds

3 baths

2,006 sq ft

House

4 beds

2 baths

2,532 sq ft

House

3 beds

2 baths

1,983 sq ft

House

3 beds

2 baths

1,641 sq ft

House

2 beds

2 baths

1,288 sq ft

House

2 beds

2 baths

1,556 sq ft

House

2 beds

2 baths

1,646 sq ft

House

3 beds

2 baths

2,151 sq ft

House

2 beds

2 baths

1,574 sq ft

House

1 beds

1 baths

837 sq ft

House

2 beds

2 baths

1,290 sq ft

Villa

4 beds

2 baths

1,894 sq ft

House

4 beds

3 baths

1,894 sq ft

House

4 beds

3 baths

2,510 sq ft

House

3 beds

2 baths

1,617 sq ft

Villa

4 beds

2 baths

1,983 sq ft

House

2 beds