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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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

11092 SE 174TH LOOP, SUMMERFIELD, FL, 34...

Community: Stonecrest

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Stonecrest

17471 SE 110TH TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491

$374,000

3 beds

2 baths

2,020 sq ft

House

17471 SE 110TH TER, SUMMERFIELD, FL, 344...

Community: Stonecrest

Plantation Bay Golf & Country Club

665 SOUTHLAKE DR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174

$780,000

4 beds

3 baths

2,601 sq ft

House

665 SOUTHLAKE DR, ORMOND BEACH, FL, 3217...

Community: Plantation Bay Golf & Country Club

Plantation Bay Golf & Country Club

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

$359,000

2 beds

2 baths

1,510 sq ft

Townhouse

820 ALDENHAM LN, ORMOND BEACH, FL, 32174

7177 SE 172ND HAZELWOOD LOOP, THE VILLAG...

Community: The Villages®

Heritage Isle

6908 MCGRADY DR, MELBOURNE, FL, 32940, Melbourne, FL 32940

$489,000

4 beds

3 baths

2,064 sq ft

House

6908 MCGRADY DR, MELBOURNE, FL, 32940

Community: Heritage Isle

The Villages®

$500,000

4 beds

3 baths

2,202 sq ft

House

164 PALERMO PL, THE VILLAGES, FL, 32159

Community: The Villages®

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The Villages®

$285,000

2 beds

2 baths

1,248 sq ft

House

1815 KAUFMAN CIR, THE VILLAGES, FL, 3215...

Community: The Villages®

The Villages®

$416,000

3 beds

2 baths

1,667 sq ft

House

560 SMITHFIELD PL, THE VILLAGES, FL, 321...

Community: The Villages®

The Villages®

$365,000

2 beds

2 baths

1,152 sq ft

Villa

3627 FULCRUM PL, THE VILLAGES, FL, 32163

Community: The Villages®

The Villages®

$360,000

3 beds

2 baths

1,407 sq ft

Villa

852 SAPPHIRE PL, THE VILLAGES, FL, 32163

Community: The Villages®

Esplanade at Highland Ranch

1343 ZEEK RIDGE ST, CLERMONT, FL, 34715, Clermont, FL 34715

$635,000

3 beds

3 baths

2,449 sq ft

House

1343 ZEEK RIDGE ST, CLERMONT, FL, 34715

Community: Esplanade at Highland Ranch

Solivita

537 MONTAGE LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$549,900

3 beds

3 baths

2,441 sq ft

House

537 MONTAGE LN, KISSIMMEE, FL, 34759

Community: Solivita

Spruce Creek Country Club

12895 SE 91ST TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491

$495,000

2 beds

3 baths

2,559 sq ft

House

12895 SE 91ST TERRACE RD, SUMMERFIELD, F...

Community: Spruce Creek Country Club

The Villages®

$499,000

3 beds

2 baths

1,927 sq ft

House

2739 MIDLAND TER, THE VILLAGES, FL, 3216...

Community: The Villages®

Plantation Bay Golf & Country Club

1240 HAMPSTEAD LN, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174

$584,500

4 beds

2 baths

2,436 sq ft

House

1240 HAMPSTEAD LN, ORMOND BEACH, FL, 321...

Community: Plantation Bay Golf & Country Club

Heritage Isle

3122 GRAYSON DR, MELBOURNE, FL, 32940, Melbourne, FL 32940

$420,000

3 beds

2 baths

1,992 sq ft

House

3122 GRAYSON DR, MELBOURNE, FL, 32940

Community: Heritage Isle

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

Questions? Call us: (888) 625-4885

Pelican Bay Daytona Beach

105 MARBLED GODWIT CT, DAYTONA BEACH, FL..., Daytona Beach, FL 32119

$395,000

3 beds

2 baths

2,568 sq ft

House

105 MARBLED GODWIT CT, DAYTONA BEACH, FL...

Community: Pelican Bay Daytona Beach

The Villages®

632 DELGADO AVE, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$399,900

2 beds

2 baths

1,139 sq ft

Villa

632 DELGADO AVE, LADY LAKE, FL, 32159

Community: The Villages®

The Villages®

$375,000

3 beds

2 baths

1,851 sq ft

House

2450 MERIDA CIR, THE VILLAGES, FL, 32162

Community: The Villages®

Solivita

1824 PELICAN HILL WAY, POINCIANA, FL, 34..., Poinciana, FL 34759

$266,500

2 beds

2 baths

1,515 sq ft

House

1824 PELICAN HILL WAY, POINCIANA, FL, 34...

Community: Solivita

The Villages®

$380,000

3 beds

2 baths

1,918 sq ft

House

8294 SE 177TH WINTERTHUR LOOP, THE VILLA...

Community: The Villages®

The Villages®

$400,000

3 beds

2 baths

2,000 sq ft

House

17722 SE 81ST TIMBERWOOD TER, THE VILLAG...

Community: The Villages®

The Villages®

$324,900

3 beds

2 baths

1,392 sq ft

House

289 ZINGALE LN, THE VILLAGES, FL, 32163

Community: The Villages®

The Villages®

12406 NE 50TH VW, OXFORD, FL, 34484, Oxford, FL 34484

$285,000

4 beds

4 baths

2,096 sq ft

House

12406 NE 50TH VW, OXFORD, FL, 34484

Community: The Villages®

Kings Ridge

3706 DOUNE WAY, CLERMONT, FL, 34711, Clermont, FL 34711

$325,000

2 beds

2 baths

1,466 sq ft

House

3706 DOUNE WAY, CLERMONT, FL, 34711

Community: Kings Ridge

Lake Ashton

5201 GREEN DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884

$374,500

3 beds

2 baths

1,845 sq ft

House

5201 GREEN DR, WINTER HAVEN, FL, 33884

Community: Lake Ashton

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

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The Villages®

$309,000

2 beds

2 baths

1,383 sq ft

House

1201 DE LA FUENTE CT, THE VILLAGES, FL, ...

Community: The Villages®

The Villages®

$215,000

1 beds

1 baths

920 sq ft

House

718 VILLITA LN, THE VILLAGES, FL, 32159

Community: The Villages®

Plantation at Leesburg

5305 INGLESIDE, LEESBURG, FL, 34748, Leesburg, FL 34748

$179,900

2 beds

2 baths

1,220 sq ft

Manufactured Home

5305 INGLESIDE, LEESBURG, FL, 34748

Community: Plantation at Leesburg

Legacy of Leesburg

5714 CELEBRATION WAY, LEESBURG, FL, 3474..., Leesburg, FL 34748

$295,000

3 beds

2 baths

1,632 sq ft

House

5714 CELEBRATION WAY, LEESBURG, FL, 3474...

Community: Legacy of Leesburg

The Villages®

$369,900

3 beds

2 baths

2,145 sq ft

House

2461 MERIDA CIR, THE VILLAGES, FL, 32162

Community: The Villages®

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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

2 baths

1,392 sq ft

House

3 beds

2 baths

1,488 sq ft

House

2 beds

2 baths

1,308 sq ft

House

2 beds

2 baths

1,248 sq ft

Manufactured Home

3 beds

3 baths

2,071 sq ft

House

3 beds

2 baths

2,020 sq ft

House

4 beds

3 baths

2,601 sq ft

House

2 beds

2 baths

1,510 sq ft

Townhouse

5 beds

5 baths

4,840 sq ft

House

2 beds

2 baths

1,186 sq ft

Villa

2 beds

2 baths

2,077 sq ft

House

3 beds

2 baths

2,403 sq ft

House

3 beds

2 baths

1,918 sq ft

House

4 beds

3 baths

2,064 sq ft

House

4 beds

3 baths

2,202 sq ft

House

2 beds

2 baths

1,248 sq ft

House

3 beds

2 baths

1,667 sq ft

House

2 beds

2 baths

1,152 sq ft

Villa

3 beds

2 baths

1,407 sq ft

Villa

3 beds