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

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

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

790 CARMEL LN, POINCIANA, FL, 34759

Manufactured Home

1576 LONGBOW DR, LAKELAND, FL, 33810

Community: Foxwood Lake Estates

The Savannahs

4156 CATGRASS LN, WEST MELBOURNE, FL, 32..., West Melbourne, FL 32904

$430,000

3 beds

2 baths

1,812 sq ft

House

4156 CATGRASS LN, WEST MELBOURNE, FL, 32...

Community: The Savannahs

Solivita

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

$244,900

2 beds

2 baths

1,240 sq ft

House

156 GRAND CANAL DR, POINCIANA, FL, 34759

Community: Solivita

The Villages®

$169,900

2 beds

1 baths

936 sq ft

Manufactured Home

622 JENNIFER DR, THE VILLAGES, FL, 32159

Community: The Villages®

Del Webb Sunbridge

2587 CLIFF WAY, SAINT CLOUD, FL, 34771, Saint Cloud, FL 34771

$420,000

2 beds

2 baths

1,401 sq ft

House

2587 CLIFF WAY, SAINT CLOUD, FL, 34771

House

610 FANNICH CT, LEESBURG, FL, 34788

Community: Scottish Highlands

Halifax Plantation

3242 BAILEY ANN DR, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174

$348,000

3 beds

2 baths

2,301 sq ft

House

3242 BAILEY ANN DR, ORMOND BEACH, FL, 32...

Community: Halifax Plantation

Breakaway Trails

94 SHADOWCREEK WAY, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174

$650,000

4 beds

3 baths

3,261 sq ft

House

94 SHADOWCREEK WAY, ORMOND BEACH, FL, 32...

Community: Breakaway Trails

Latitude Margaritaville

220 SAND BAR LN, DAYTONA BEACH, FL, 3212..., Daytona Beach, FL 32124

$479,500

2 beds

2 baths

1,771 sq ft

House

220 SAND BAR LN, DAYTONA BEACH, FL, 3212...

Community: Latitude Margaritaville

Trilogy® Orlando

815 HIDDEN MOSS DR, GROVELAND, FL, 34736, Groveland, FL 34736

$450,000

2 beds

3 baths

2,339 sq ft

House

815 HIDDEN MOSS DR, GROVELAND, FL, 34736

Community: Trilogy® Orlando

Latitude Margaritaville

472 LANDSHARK BLVD, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124

$419,900

2 beds

2 baths

1,464 sq ft

House

472 LANDSHARK BLVD, DAYTONA BEACH, FL, 3...

Community: Latitude Margaritaville

Arlington Ridge

27121 WHITE PLAINS WAY, LEESBURG, FL, 34..., Leesburg, FL 34748

$275,000

2 beds

2 baths

1,418 sq ft

Villa

27121 WHITE PLAINS WAY, LEESBURG, FL, 34...

Community: Arlington Ridge

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

Questions? Call us: (888) 625-4885

The Villages®

$328,000

3 beds

2 baths

1,752 sq ft

House

9161 SE 169TH BENTLEY ST, THE VILLAGES, ...

Community: The Villages®

Stonecrest

17083 SE 115TH TERRACE RD, SUMMERFIELD, ..., Summerfield, FL 34491

$330,000

3 beds

2 baths

1,782 sq ft

House

17083 SE 115TH TERRACE RD, SUMMERFIELD, ...

Community: Stonecrest

Sandpiper Golf & Country Club

6253 SANDPIPERS DR, LAKELAND, FL, 33809, Lakeland, FL 33809

$259,900

2 beds

2 baths

976 sq ft

House

6253 SANDPIPERS DR, LAKELAND, FL, 33809

Community: Sandpiper Golf & Country Club

The Timbers at Everlands

853 ANTIBES CT NW, PALM BAY, FL, 32907, Palm Bay, FL 32907

$444,950

3 beds

3 baths

2,182 sq ft

House

853 ANTIBES CT NW, PALM BAY, FL, 32907

Community: The Timbers at Everlands

Spruce Creek Country Club

12947 SE 97TH TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491

$410,000

3 beds

2 baths

2,126 sq ft

House

12947 SE 97TH TERRACE RD, SUMMERFIELD, F...

Community: Spruce Creek Country Club

The Timbers at Everlands

2223 ANTARUS DR NW, PALM BAY, FL, 32907, Palm Bay, FL 32907

$364,950

3 beds

4 baths

1,710 sq ft

House

2223 ANTARUS DR NW, PALM BAY, FL, 32907

Community: The Timbers at Everlands

Halifax Plantation

3145 CONNEMARA DR, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174

$409,000

3 beds

3 baths

2,384 sq ft

House

3145 CONNEMARA DR, ORMOND BEACH, FL, 321...

Community: Halifax Plantation

Halifax Plantation

3217 BAILEY ANN DR, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174

$348,000

3 beds

2 baths

1,695 sq ft

House

3217 BAILEY ANN DR, ORMOND BEACH, FL, 32...

Community: Halifax Plantation

The Villages®

$385,000

3 beds

2 baths

1,558 sq ft

House

937 KAUSKA WAY, THE VILLAGES, FL, 32163

Community: The Villages®

The Villages®

$339,900

2 beds

2 baths

1,206 sq ft

House

2845 CHARITY LOOP, THE VILLAGES, FL, 321...

House

17733 SE 95TH CIR, SUMMERFIELD, FL, 3449...

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

1,722 sq ft

Condo

2 beds

2 baths

1,143 sq ft

House

2 beds

2 baths

1,713 sq ft

House

2 beds

2 baths

3,034 sq ft

House

4 beds

3 baths

2,430 sq ft

House

2 beds

2 baths

1,045 sq ft

House

2 beds

2 baths

1,224 sq ft

Manufactured Home

3 beds

2 baths

2,001 sq ft

House

3 beds

2 baths

1,892 sq ft

House

2 beds

2 baths

2,064 sq ft

House

3 beds

2 baths

1,152 sq ft

Manufactured Home

3 beds

2 baths

1,812 sq ft

House

2 beds

2 baths

1,240 sq ft

House

2 beds

1 baths

936 sq ft

Manufactured Home

2 beds

2 baths

1,401 sq ft

House

2 beds

2 baths

1,356 sq ft

Villa

2 beds

2 baths

1,799 sq ft

House

2 beds

2 baths

1,637 sq ft

House

2 beds

2 baths

1,182 sq ft

House

3 beds