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

913 SOLEDAD WAY, THE VILLAGES, FL, 32159

Community: The Villages®

Pelican Bay Daytona Beach

149 BLACK DUCK CIR, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32119

$219,990

2 beds

2 baths

1,075 sq ft

House

149 BLACK DUCK CIR, DAYTONA BEACH, FL, 3...

Community: Pelican Bay Daytona Beach

The Villages®

$412,990

3 beds

2 baths

1,647 sq ft

Villa

2467 ROGERS RD, THE VILLAGES, FL, 32163

House

2415 MORVEN PARK WAY, THE VILLAGES, FL, ...

5007 BELTED KINGFISHER DR, OXFORD, FL, 3...

Community: Lakeside Landings

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Questions? Call us: (888) 625-4885

New The Villages®

718 SHELTON ST, THE VILLAGES, FL, 32163, The Villages, FL 32163

$325,000

3 beds

2 baths

1,607 sq ft

House

718 SHELTON ST, THE VILLAGES, FL, 32163

Community: The Villages®

Solivita

161 CAPE FLORIDA DR, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759

$285,000

2 beds

2 baths

1,491 sq ft

House

161 CAPE FLORIDA DR, KISSIMMEE, FL, 3475...

Community: Solivita

Carmel Condominium

1420 HUNTINGTON LN 2502, ROCKLEDGE, FL, ..., Rockledge, FL 32955

$125,000

2 beds

2 baths

1,008 sq ft

Condo

1420 HUNTINGTON LN 2502, ROCKLEDGE, FL, ...

Community: Carmel Condominium

New Grand Haven

30 LAKESIDE DR, PALM COAST, FL, 32137, Palm Coast, FL 32137

$650,000

3 beds

3 baths

2,246 sq ft

House

30 LAKESIDE DR, PALM COAST, FL, 32137

Community: Grand Haven

Plantation at Leesburg

5042 DESOTO WAY, LEESBURG, FL, 34748, Leesburg, FL 34748

$205,000

2 beds

2 baths

1,326 sq ft

House

5042 DESOTO WAY, LEESBURG, FL, 34748

Community: Plantation at Leesburg

The Villages®

$262,900

2 beds

2 baths

979 sq ft

Villa

2389 TIFFANY TER, THE VILLAGES, FL, 3216...

Community: The Villages®

The Villages®

$199,000

2 beds

2 baths

1,144 sq ft

Manufactured Home

912 ORCHID ST, THE VILLAGES, FL, 32159

Community: The Villages®

The Villages®

$360,000

3 beds

2 baths

1,407 sq ft

Villa

610 DANBURY ST, THE VILLAGES, FL, 32162

Community: The Villages®

The Villages®

$1,775,000

3 beds

3 baths

3,100 sq ft

House

664 TERNBERRY FOREST DR, THE VILLAGES, F...

Community: The Villages®

Venetian Bay

3361 STEFANO ST, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168

$525,000

3 beds

3 baths

2,136 sq ft

House

3361 STEFANO ST, NEW SMYRNA BEACH, FL, 3...

Community: Venetian Bay

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

Questions? Call us: (888) 625-4885

The Villages®

$269,000

2 beds

2 baths

1,383 sq ft

House

518 ALCAZAR CT, THE VILLAGES, FL, 32159

Community: The Villages®

Solivita

582 SAN JOAQUIN RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$369,900

3 beds

2 baths

1,730 sq ft

House

582 SAN JOAQUIN RD, KISSIMMEE, FL, 34759

Community: Solivita

The Villages®

$275,000

2 beds

2 baths

1,150 sq ft

House

2003 CORDERO CT, THE VILLAGES, FL, 32159

Community: The Villages®

Stonecrest

12321 SE 176TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491

$329,000

3 beds

2 baths

1,815 sq ft

House

12321 SE 176TH LOOP, SUMMERFIELD, FL, 34...

Community: Stonecrest

Arlington Ridge

26712 AUGUSTA SPRINGS CIR, LEESBURG, FL,..., Leesburg, FL 34748

$384,900

2 beds

2 baths

2,211 sq ft

House

26712 AUGUSTA SPRINGS CIR, LEESBURG, FL,...

Community: Arlington Ridge

Plantation Bay Golf & Country Club

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

$625,000

3 beds

3 baths

2,073 sq ft

House

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

Community: Plantation Bay Golf & Country Club

Latitude Margaritaville

786 JOLLYMON WAY, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124

$729,900

3 beds

3 baths

2,392 sq ft

House

786 JOLLYMON WAY, DAYTONA BEACH, FL, 321...

Community: Latitude Margaritaville

Lakes at Laurel Highlands

2795 GRANDBURY GROVE RD, LAKELAND, FL, 3..., Lakeland, FL 33811

$329,000

3 beds

2 baths

1,769 sq ft

House

2795 GRANDBURY GROVE RD, LAKELAND, FL, 3...

Community: Lakes at Laurel Highlands

Heritage Landings

$329,000

3 beds

2 baths

1,769 sq ft

House

2795 GRANDBURY GROVE RD, LAKELAND, FL, 3...

Community: Heritage Landings

The Villages®

$175,900

2 beds

2 baths

1,036 sq ft

Manufactured Home

902 ROSE LN, THE VILLAGES, FL, 32159

House

32942 RAMBLING OAKS CT, LEESBURG, FL, 34...

Community: Pennbrooke Fairways

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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

2,000 sq ft

House

3 beds

2 baths

1,649 sq ft

House

3 beds

2 baths

1,982 sq ft

House

2 beds

2 baths

1,075 sq ft

House

3 beds

2 baths

1,647 sq ft

Villa

3 beds

2 baths

1,537 sq ft

Villa

3 beds

2 baths

2,322 sq ft

House

2 beds

2 baths

1,382 sq ft

House

2 beds

2 baths

1,161 sq ft

House

3 beds

3 baths

2,033 sq ft

House

2 beds

2 baths

1,182 sq ft

Villa

3 beds

2 baths

2,057 sq ft

House

3 beds

2 baths

1,910 sq ft

House

3 beds

2 baths

2,046 sq ft

House

3 beds

2 baths

2,352 sq ft

House

3 beds

2 baths

1,607 sq ft

House

2 beds

2 baths

1,491 sq ft

House

2 beds

2 baths

1,008 sq ft

Condo

3 beds

3 baths

2,246 sq ft

House

2 beds