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

2,487 homes near Winter Park

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4 rating (17 reviews)

The Villages®

<$100k - $1Ms

The Villages®, The Villages, FL

New and Resale | 55+ age-restricted | Built 1978 - present | 70,000 homes

4.7 rating (18 reviews)

Solivita

$100Ks - $600Ks

Solivita, Kissimmee, FL

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

3.6 rating (48 reviews)

Latitude Margaritaville

$300Ks - $900Ks

Latitude Margaritaville, Daytona Beach, FL

Resale Only | 55+ age-restricted | Built 2017 - 2025 | 3,900 homes

5 rating (1 reviews)

Plantation Bay Golf &...

$200Ks - $4Ms

Plantation Bay Golf &..., Ormond Beach, FL

New and Resale | Age-targeted | Built 1988 - present | 3,500 homes

4.5 rating (11 reviews)

Spruce Creek Country Club

$200Ks - $500Ks

Spruce Creek Country Club, Summerfield, FL

Resale Only | 55+ age-restricted | Built 1996 - 2007 | 3,250 homes

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5 rating (2 reviews)

Plantation at Leesburg

$100Ks - $500Ks

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

New and Resale | 55+ age-restricted | Built 1990 - present | 2,200 homes

5 rating (7 reviews)

Kings Ridge

$200Ks - $400Ks

Kings Ridge, Clermont, FL

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

Grand Haven

$300Ks - $1Ms

Grand Haven, Palm Coast, FL

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

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Pelican Bay Daytona Beach

$100Ks - $500Ks

Pelican Bay Daytona Beach, Daytona Beach, FL

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

4.7 rating (3 reviews)

Spruce Creek South

$100Ks - $300Ks

Spruce Creek South, Summerfield, FL

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

5 rating (1 reviews)

Cypress Lakes

$100Ks - $200Ks

Cypress Lakes, Lakeland, FL

Resale Only | 55+ age-restricted | Built 1987 - 2016 | 1,604 homes

5 rating (3 reviews)

Lake Ashton

$200Ks - $800Ks

Lake Ashton, Lake Wales, FL

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

Venetian Bay

$200Ks - $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)

Heritage Isle

$200Ks - $500Ks

Heritage Isle, Viera, FL

Resale Only | 55+ age-restricted | Built 2005 - 2017 | 1,500 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)

Royal Highlands

$200Ks - $500Ks

Royal Highlands, Leesburg, FL

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

5 rating (1 reviews)

Del Webb Sunbridge

$300Ks - $1Ms

Del Webb Sunbridge, St. Cloud, FL

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

5 rating (1 reviews)

VillageWalk at Lake Nona

$300Ks - $1Ms

VillageWalk at Lake Nona, Orlando, FL

Resale Only | Age-targeted | Built 2006 - 2016 | 1,300 homes

Del Webb at Viera

$300Ks - $800Ks

Del Webb at Viera, Melbourne, FL

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

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)

Sandpiper Golf & Coun...

$200Ks - $400Ks

Sandpiper Golf & Coun..., Lakeland, FL

New and Resale | 55+ age-restricted | Built 1985 - present | 1,193 homes

3.6 rating (5 reviews)

Heritage Hills

$200Ks - $500Ks

Heritage Hills, Clermont, FL

New and Resale | 55+ age-restricted | Built 2006 - present | 1,154 homes

5 rating (1 reviews)

Cresswind at Victoria Gar...

$300Ks - $600Ks

Cresswind at Victoria Gar..., DeLand, FL

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

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Questions? Call us: (888) 625-4885

Halifax Plantation

$200Ks - $700Ks

Halifax Plantation, Ormond Beach, FL

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

Breakaway Trails

$400Ks - $700Ks

Breakaway Trails, Ormond Beach, FL

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

4 rating (4 reviews)

Lakes of Mount Dora

$400Ks - $900Ks

Lakes of Mount Dora, Mount Dora, FL

New and Resale | 55+ age-restricted | Built 2006 - present | 950 homes

4 rating (2 reviews)

Harbor Hills Country Club

$200Ks - $1Ms

Harbor Hills Country Club, Lady Lake, FL

New and Resale | Age-targeted | Built 1989 - present | 940 homes

4.8 rating (6 reviews)

Highland Lakes

$100Ks - $300Ks

Highland Lakes, Leesburg, FL

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

4.4 rating (16 reviews)

Del Webb Orlando

$300Ks - $400Ks

Del Webb Orlando, Davenport, FL

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

5 rating (2 reviews)

Bridgewater at Viera

$300Ks - $600Ks

Bridgewater at Viera, Melbourne, FL

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

4.1 rating (9 reviews)

Indian River Colony Club

$200Ks - $400Ks

Indian River Colony Club, Melbourne, FL

New and Resale | 55+ age-restricted | Built 1986 - present | 777 homes

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Questions? Call us: (888) 625-4885

3.9 rating (7 reviews)

Summit Greens

$300Ks - $400Ks

Summit Greens, Clermont, FL

Resale Only | 55+ age-restricted | Built 2001 - 2019 | 769 homes

5 rating (1 reviews)

Royal Harbor

$200Ks - $400Ks

Royal Harbor, Tavares, FL

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

Lakeside Landings

$200Ks - $500Ks

Lakeside Landings, Oxford, FL

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

1 rating (1 reviews)

Sullivan Ranch

$300Ks - $600Ks

Sullivan Ranch, Mount Dora, FL

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

Highland Fairways

$100Ks - $300Ks

Highland Fairways, Lakeland, FL

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

17860 SE 89TH NATCHEZ AVE, THE VILLAGES,...

Community: The Villages®

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Questions? Call us: (888) 625-4885

The Villages®

$589,000

2 beds

2 baths

1,522 sq ft

House

1302 LOPEZ LN, THE VILLAGES, FL, 32159

Community: The Villages®

The Villages®

$159,000

2 beds

1 baths

828 sq ft

Manufactured Home

610 TARRSON BLVD, THE VILLAGES, FL, 3215...

Community: The Villages®

The Villages®

$629,900

3 beds

3 baths

2,400 sq ft

House

1371 OWL DR, THE VILLAGES, FL, 32163

Community: The Villages®

Cresswind at Victoria Gardens

600 GARDEN CLUB DR, DELAND, FL, 32724, Deland, FL 32724

$554,900

4 beds

3 baths

2,569 sq ft

House

600 GARDEN CLUB DR, DELAND, FL, 32724

Community: Cresswind at Victoria Gardens

Legacy of Leesburg

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

$464,900

4 beds

5 baths

3,125 sq ft

House

5351 AURORA DR, LEESBURG, FL, 34748

Community: Legacy of Leesburg

Venetian Bay

505 VENETIAN PALMS BLVD, NEW SMYRNA BEAC..., New Smyrna Beach, FL 32168

$347,500

3 beds

3 baths

1,758 sq ft

House

505 VENETIAN PALMS BLVD, NEW SMYRNA BEAC...

Community: Venetian Bay

Lake Ashton

4331 ASHTON CLUB DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859

$295,900

3 beds

2 baths

1,457 sq ft

House

4331 ASHTON CLUB DR, LAKE WALES, FL, 338...

Community: Lake Ashton

Stonecrest

17782 SE 113TH TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491

$279,000

2 beds

2 baths

1,234 sq ft

Villa

17782 SE 113TH TER, SUMMERFIELD, FL, 344...

Community: Stonecrest

Lakes of Mount Dora

2435 PAWTUCKET PASS, MOUNT DORA, FL, 327..., Mount Dora, FL 32757

$565,000

3 beds

2 baths

2,080 sq ft

House

2435 PAWTUCKET PASS, MOUNT DORA, FL, 327...

Community: Lakes of Mount Dora

The Villages®

$259,000

2 beds

2 baths

1,066 sq ft

House

1410 SANCHEZ CT, THE VILLAGES, FL, 32159

House

6 FOX LAIR CT, ORMOND BEACH, FL, 32174

3457 CARRABELLE CT, THE VILLAGES, FL, 32...

Community: The Villages®

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Alhambra Villas Condominiums

183 N HILL AVE # 90, DELAND, FL, 32724, Deland, FL 32724

$179,500

2 beds

2 baths

979 sq ft

Condo

183 N HILL AVE # 90, DELAND, FL, 32724

Community: Alhambra Villas Condominiums

Arlington Ridge

26694 OTTER CREEK LN, LEESBURG, FL, 3474..., Leesburg, FL 34748

$499,000

3 beds

3 baths

2,399 sq ft

House

26694 OTTER CREEK LN, LEESBURG, FL, 3474...

Community: Arlington Ridge

The Villages®

$279,000

2 beds

2 baths

1,188 sq ft

Villa

3604 CAMBRIA CIR, THE VILLAGES, FL, 3216...

Community: The Villages®

Highland Lakes

26736 CASH CT, LEESBURG, FL, 34748, Leesburg, FL 34748

$215,000

2 beds

2 baths

1,293 sq ft

Villa

26736 CASH CT, LEESBURG, FL, 34748

Community: Highland Lakes

Royal Highlands

4528 GLEN COE ST, LEESBURG, FL, 34748, Leesburg, FL 34748

$410,000

2 beds

2 baths

2,200 sq ft

House

4528 GLEN COE ST, LEESBURG, FL, 34748

Community: Royal Highlands

Huntington at Hunter's Ridge

3 HAWK ROOST CT, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$353,000

2 beds

2 baths

1,593 sq ft

House

3 HAWK ROOST CT, ORMOND BEACH, FL, 32174

Community: Huntington at Hunter's Ridge

Plantation Bay Golf & Country Club

823 CREEKWOOD DR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174

$575,000

3 beds

2 baths

1,762 sq ft

House

823 CREEKWOOD DR, ORMOND BEACH, FL, 3217...

Community: Plantation Bay Golf & Country Club

The Villages®

$285,900

2 beds

2 baths

1,358 sq ft

Villa

17324 SE 82ND PECAN TER, THE VILLAGES, F...

Community: The Villages®

Enclave at VillageWalk

11675 SAVONA WAY, ORLANDO, FL, 32827, Orlando, FL 32827

$1,435,000

4 beds

5 baths

4,622 sq ft

House

11675 SAVONA WAY, ORLANDO, FL, 32827

Community: Enclave at VillageWalk

The Villages®

$367,500

3 beds

2 baths

1,924 sq ft

House

710 ANTONIA LN, THE VILLAGES, FL, 32159

Community: The Villages®

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

Questions? Call us: (888) 625-4885

The Villages®

$235,000

2 beds

2 baths

1,156 sq ft

Villa

3536 ROANOKE ST, THE VILLAGES, FL, 32162

Community: The Villages®

Summit Greens

2822 FALCON RDG, CLERMONT, FL, 34711, Clermont, FL 34711

$450,000

3 beds

3 baths

2,506 sq ft

House

2822 FALCON RDG, CLERMONT, FL, 34711

Community: Summit Greens

Vienna Square

$225,000

2 beds

2 baths

1,231 sq ft

Villa

1561 VIENNA SQUARE DR, WINTER HAVEN, FL,...

Community: Vienna Square

The Villages®

$350,900

3 beds

2 baths

1,531 sq ft

House

3500 COUNTRYSIDE PATH, THE VILLAGES, FL,...

Community: The Villages®

Lakes of Mount Dora

8252 BRIDGEPORT BAY CIR, MOUNT DORA, FL,..., Mount Dora, FL 32757

$385,000

3 beds

2 baths

1,473 sq ft

House

8252 BRIDGEPORT BAY CIR, MOUNT DORA, FL,...

Community: Lakes of Mount Dora

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2,487 homes near Winter Park

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

90 communities near Winter Park

2,487 homes near Winter Park

3 beds

3 baths

2,402 sq ft

House

3 beds

2 baths

1,527 sq ft

House

3 beds

2 baths

2,120 sq ft

House

4 beds

3 baths

2,321 sq ft

House

3 beds

2 baths

1,625 sq ft

House

2 beds

2 baths

1,522 sq ft

House

2 beds

1 baths

828 sq ft

Manufactured Home

3 beds

3 baths

2,400 sq ft

House

4 beds

3 baths

2,569 sq ft

House

4 beds

5 baths

3,125 sq ft

House

3 beds

3 baths

1,758 sq ft

House

3 beds

2 baths

1,457 sq ft

House

2 beds

2 baths

1,234 sq ft

Villa

3 beds

2 baths

2,080 sq ft

House

2 beds

2 baths

1,066 sq ft

House

3 beds

2 baths

1,904 sq ft

House

5 beds

3 baths

2,909 sq ft

House

3 beds

2 baths

1,909 sq ft

House

3 beds

2 baths

2,027 sq ft

House

2 beds