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

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

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

1812 CHANCEY WAY, THE VILLAGES, FL, 3216...

House

89 CROOKED PINE RD, PORT ORANGE, FL, 321...

Community: Summer Trees

Alamanda Key

608 LORELEI AVE, MELBOURNE, FL, 32901, Melbourne, FL 32901

$330,000

2 beds

2 baths

1,652 sq ft

House

608 LORELEI AVE, MELBOURNE, FL, 32901

Community: Alamanda Key

The Villages®

21204 SANDALWOOD DR # 21-204, WILDWOOD, ..., Wildwood, FL 34785

$135,000

2 beds

2 baths

1,110 sq ft

Condo

21204 SANDALWOOD DR # 21-204, WILDWOOD, ...

Community: The Villages®

Venetian Bay

3009 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168

$321,000

3 beds

3 baths

1,614 sq ft

Townhouse

3009 MELETO BLVD, NEW SMYRNA BEACH, FL, ...

Community: Venetian Bay

Arlington Ridge

$335,000

3 beds

2 baths

1,824 sq ft

House

4314 ARLINGTON RIDGE BLVD, LEESBURG, FL,...

Community: Arlington Ridge

Harbor Hills Country Club

6152 TOPSAIL RD, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$324,000

2 beds

2 baths

1,552 sq ft

House

6152 TOPSAIL RD, LADY LAKE, FL, 32159

Community: Harbor Hills Country Club

Spruce Creek Country Club

13235 SE 97TH TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491

$365,000

2 beds

2 baths

2,149 sq ft

House

13235 SE 97TH TERRACE RD, SUMMERFIELD, F...

Community: Spruce Creek Country Club

Spruce Creek Country Club

9025 SE 136TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491

$350,000

3 beds

2 baths

2,251 sq ft

House

9025 SE 136TH LOOP, SUMMERFIELD, FL, 344...

Community: Spruce Creek Country Club

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

Questions? Call us: (888) 625-4885

Breakaway Trails

8 WILD CREEK WAY, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174

$773,900

5 beds

4 baths

3,367 sq ft

House

8 WILD CREEK WAY, ORMOND BEACH, FL, 3217...

Community: Breakaway Trails

Indian River Colony Club

1419 PATRIOT DR, MELBOURNE, FL, 32940, Melbourne, FL 32940

$379,000

3 beds

3 baths

2,368 sq ft

House

1419 PATRIOT DR, MELBOURNE, FL, 32940

Community: Indian River Colony Club

Carillon Lakes

3102 BELLFLOWER WAY, LAKELAND, FL, 33811, Lakeland, FL 33811

$299,000

3 beds

2 baths

1,434 sq ft

House

3102 BELLFLOWER WAY, LAKELAND, FL, 33811

Community: Carillon Lakes

Four Seasons at Orlando

7632 SAND PIERRE CT, KISSIMMEE, FL, 3474..., Kissimmee, FL 34747

$319,900

2 beds

2 baths

1,437 sq ft

Villa

7632 SAND PIERRE CT, KISSIMMEE, FL, 3474...

Community: Four Seasons at Orlando

The Villages®

$650,000

3 beds

2 baths

1,944 sq ft

House

904 MAYNARD PATH, THE VILLAGES, FL, 3216...

Community: The Villages®

Plantation Bay Golf & Country Club

673 ELK RIVER DR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174

$485,000

3 beds

2 baths

2,271 sq ft

House

673 ELK RIVER DR, ORMOND BEACH, FL, 3217...

Community: Plantation Bay Golf & Country Club

Plantation Bay Golf & Country Club

27 BAY CT, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$649,999

3 beds

2 baths

2,101 sq ft

House

27 BAY CT, ORMOND BEACH, FL, 32174

Community: Plantation Bay Golf & Country Club

Summer Trees

79 CYPRESS POND RD # 79, PORT ORANGE, FL..., Port Orange, FL 32128

$227,000

2 beds

2 baths

888 sq ft

Condo

79 CYPRESS POND RD # 79, PORT ORANGE, FL...

Community: Summer Trees

Summer Trees

79 CYPRESS POND RD, PORT ORANGE, FL, 321..., Port Orange, FL 32128

$227,000

2 beds

2 baths

1,300 sq ft

House

79 CYPRESS POND RD, PORT ORANGE, FL, 321...

Community: Summer Trees

Highland Lakes

26616 RACQUET CIR, LEESBURG, FL, 34748, Leesburg, FL 34748

$255,000

2 beds

2 baths

1,269 sq ft

House

26616 RACQUET CIR, LEESBURG, FL, 34748

House

654 POINSETT CT, THE VILLAGES, FL, 32162

Community: The Villages®

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

Questions? Call us: (888) 625-4885

Royal Harbor

5676 GULF STREAM ST, TAVARES, FL, 32778, Tavares, FL 32778

$359,000

4 beds

3 baths

1,915 sq ft

House

5676 GULF STREAM ST, TAVARES, FL, 32778

Community: Royal Harbor

New Del Webb Minneola

1175 CROWNING RIDGE WAY, MINNEOLA, FL, 3..., Minneola, FL 34715

$454,050

2 beds

2 baths

1,405 sq ft

House

1175 CROWNING RIDGE WAY, MINNEOLA, FL, 3...

Community: Del Webb Minneola

New Ridgehaven

167 PARKHAVEN DR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174

$310,990

3 beds

2 baths

1,454 sq ft

House

167 PARKHAVEN DR, ORMOND BEACH, FL, 3217...

Community: Ridgehaven

Halifax Plantation

1480 KILRUSH DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$664,000

4 beds

3 baths

2,788 sq ft

House

1480 KILRUSH DR, ORMOND BEACH, FL, 32174

Community: Halifax Plantation

Spruce Creek South

17562 SE 106TH AVE, SUMMERFIELD, FL, 344..., Summerfield, FL 34491

$249,000

2 beds

2 baths

1,488 sq ft

House

17562 SE 106TH AVE, SUMMERFIELD, FL, 344...

Community: Spruce Creek South

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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

1,144 sq ft

Manufactured Home

2 beds

2 baths

1,156 sq ft

House

3 beds

2 baths

1,888 sq ft

House

2 beds

2 baths

1,856 sq ft

House

3 beds

2 baths

1,483 sq ft

House

2 beds

2 baths

1,383 sq ft

House

2 beds

2 baths

1,156 sq ft

Villa

2 beds

2 baths

1,010 sq ft

House

2 beds

2 baths

1,652 sq ft

House

2 beds

2 baths

1,110 sq ft

Condo

3 beds

3 baths

1,614 sq ft

Townhouse

3 beds

2 baths

1,824 sq ft

House

2 beds

2 baths

1,552 sq ft

House

2 beds

2 baths

2,149 sq ft

House

3 beds

2 baths

2,251 sq ft

House

5 beds

4 baths

3,367 sq ft

House

3 beds

3 baths

2,368 sq ft

House

3 beds

2 baths

1,434 sq ft

House

2 beds

2 baths

1,437 sq ft

Villa

3 beds