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

7545 LAUREATE BLVD UNIT 7202, ORLANDO, F...

House

5337 HOGAN LN, WINTER HAVEN, FL, 33884

Community: Lake Ashton

Pelican Bay Daytona Beach

224 BOB WHITE CT 2240, DAYTONA BEACH, FL..., Daytona Beach, FL 32119

$240,000

3 beds

3 baths

1,668 sq ft

Townhouse

224 BOB WHITE CT 2240, DAYTONA BEACH, FL...

Community: Pelican Bay Daytona Beach

Del Webb Sunbridge

6212 CITRUS GROVE CT, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34771

$749,665

4 beds

3 baths

2,842 sq ft

House

6212 CITRUS GROVE CT, SAINT CLOUD, FL, 3...

Community: Del Webb Sunbridge

Del Webb Sunbridge

6456 SHIMMERING SHORES LN, SAINT CLOUD, ..., Saint Cloud, FL 34771

$474,961

2 beds

2 baths

1,405 sq ft

House

6456 SHIMMERING SHORES LN, SAINT CLOUD, ...

Community: Del Webb Sunbridge

Lakeside Landings

5129 JAREDS LANDING WAY, OXFORD, FL, 344..., Oxford, FL 34484

$499,000

3 beds

2 baths

2,296 sq ft

House

5129 JAREDS LANDING WAY, OXFORD, FL, 344...

Community: Lakeside Landings

Del Webb Orlando

329 ALICANTE CT, DAVENPORT, FL, 33837, Davenport, FL 33837

$415,000

3 beds

2 baths

2,000 sq ft

House

329 ALICANTE CT, DAVENPORT, FL, 33837

Community: Del Webb Orlando

Del Webb at Viera

3113 TIDEPOOL PL, MELBOURNE, FL, 32940, Melbourne, FL 32940

$689,900

3 beds

2 baths

1,655 sq ft

House

3113 TIDEPOOL PL, MELBOURNE, FL, 32940

Community: Del Webb at Viera

Cresswind at Victoria Gardens

1612 LINCOLNSHIRE DR, DELAND, FL, 32724, Deland, FL 32724

$399,000

3 beds

2 baths

1,905 sq ft

House

1612 LINCOLNSHIRE DR, DELAND, FL, 32724

Community: Cresswind at Victoria Gardens

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

Questions? Call us: (888) 625-4885

Spruce Creek Country Club

13536 SE 97TH TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491

$419,000

3 beds

2 baths

1,936 sq ft

House

13536 SE 97TH TERRACE RD, SUMMERFIELD, F...

Community: Spruce Creek Country Club

Plantation at Leesburg

4242 LEAFWAY CIR, LEESBURG, FL, 34748, Leesburg, FL 34748

$410,000

2 beds

2 baths

2,297 sq ft

House

4242 LEAFWAY CIR, LEESBURG, FL, 34748

Community: Plantation at Leesburg

Solivita

680 PORTOFINO DR, POINCIANA, FL, 34759, Poinciana, FL 34759

$324,785

3 beds

2 baths

1,813 sq ft

House

680 PORTOFINO DR, POINCIANA, FL, 34759

Community: Solivita

Summit Greens

2817 FALCON RDG, CLERMONT, FL, 34711, Clermont, FL 34711

$429,000

3 beds

3 baths

2,300 sq ft

House

2817 FALCON RDG, CLERMONT, FL, 34711

Community: Summit Greens

Solivita

432 GRAND CANAL DR, POINCIANA, FL, 34759, Poinciana, FL 34759

$268,000

2 beds

2 baths

1,507 sq ft

House

432 GRAND CANAL DR, POINCIANA, FL, 34759

Community: Solivita

Oakview

$226,650

2 beds

2 baths

1,438 sq ft

House

1518 OAKVIEW CIR, WINTER HAVEN, FL, 3388...

Community: Oakview

Latitude Margaritaville

148 GYPSY PALACE LN, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124

$429,900

2 beds

2 baths

1,378 sq ft

House

148 GYPSY PALACE LN, DAYTONA BEACH, FL, ...

Community: Latitude Margaritaville

The Villages®

$384,247

3 beds

2 baths

1,587 sq ft

House

1675 WESTMINSTER CT, THE VILLAGES, FL, 3...

Community: The Villages®

Del Webb at Viera

8528 ROCARD CT, MELBOURNE, FL, 32940, Melbourne, FL 32940

$684,076

3 beds

3 baths

2,122 sq ft

House

8528 ROCARD CT, MELBOURNE, FL, 32940

Community: Del Webb at Viera

High Vista at Ridgewood Lakes

106 MOSSY OAK DR, DAVENPORT, FL, 33837, Davenport, FL 33837

$360,000

3 beds

2 baths

1,797 sq ft

House

106 MOSSY OAK DR, DAVENPORT, FL, 33837

Community: High Vista at Ridgewood Lakes

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

Questions? Call us: (888) 625-4885

The Villages®

$359,000

3 beds

2 baths

1,872 sq ft

House

1307 GALINDO PL, THE VILLAGES, FL, 32159

Community: The Villages®

Legacy of Leesburg

27121 GREENFLY ORCHID LN, LEESBURG, FL, ..., Leesburg, FL 34748

$275,000

3 beds

2 baths

1,478 sq ft

House

27121 GREENFLY ORCHID LN, LEESBURG, FL, ...

Community: Legacy of Leesburg

Harbor Hills Country Club

5556 GROVE MNR, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$320,000

3 beds

2 baths

1,525 sq ft

House

5556 GROVE MNR, LADY LAKE, FL, 32159

Community: Harbor Hills Country Club

Trilogy® Orlando

228 BAYOU BEND RD, GROVELAND, FL, 34736, Groveland, FL 34736

$455,000

2 beds

2 baths

2,197 sq ft

House

228 BAYOU BEND RD, GROVELAND, FL, 34736

Community: Trilogy® Orlando

The Villages®

$287,000

2 beds

2 baths

1,156 sq ft

Villa

2552 MARIEL WAY, THE VILLAGES, FL, 32162

Community: The Villages®

Plantation Bay Golf & Country Club

45 MAGNOLIA DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$262,800

2 beds

2 baths

1,300 sq ft

Condo

45 MAGNOLIA DR, ORMOND BEACH, FL, 32174

Community: Plantation Bay Golf & Country Club

Summit Greens

$370,000

2 beds

2 baths

1,731 sq ft

House

793 SUMMIT GREENS BLVD, CLERMONT, FL, 34...

Community: Summit Greens

The Villages®

$349,900

2 beds

2 baths

1,187 sq ft

House

1083 JACKSON ST, THE VILLAGES, FL, 32162

Community: The Villages®

The Villages®

5371 WARM SPRINGS AVE, WILDWOOD, FL, 347..., Wildwood, FL 34785

$275,000

2 beds

1 baths

696 sq ft

House

5371 WARM SPRINGS AVE, WILDWOOD, FL, 347...

Community: The Villages®

Highland Lakes

26104 NEWCOMBE CIR, LEESBURG, FL, 34748, Leesburg, FL 34748

$245,000

2 beds

2 baths

1,124 sq ft

House

26104 NEWCOMBE CIR, LEESBURG, FL, 34748

Condo

5368 COMPASS PT # 202, OXFORD, FL, 34484

Community: Lakeside Landings

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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

2 beds

2 baths

1,557 sq ft

Villa

3 beds

2 baths

1,559 sq ft

Villa

2 beds

2 baths

1,368 sq ft

Condo

2 beds

2 baths

1,368 sq ft

Condo

3 beds

2 baths

1,805 sq ft

Condo

2 beds

2 baths

1,549 sq ft

Condo

2 beds

2 baths

1,240 sq ft

House

3 beds

2 baths

1,833 sq ft

House

3 beds

3 baths

1,668 sq ft

Townhouse

4 beds

3 baths

2,842 sq ft

House

2 beds

2 baths

1,405 sq ft

House

3 beds

2 baths

2,296 sq ft

House

3 beds

2 baths

2,000 sq ft

House

3 beds

2 baths

1,655 sq ft

House

3 beds

2 baths

1,905 sq ft

House

3 beds

2 baths

1,936 sq ft

House

2 beds

2 baths

2,297 sq ft

House

3 beds

2 baths

1,813 sq ft

House

3 beds

3 baths

2,300 sq ft

House

2 beds