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

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 (2 reviews)

Heritage Isle

$200Ks - $500Ks

Heritage Isle, Viera, FL

Resale Only | 55+ age-restricted | Built 2005 - 2017 | 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

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 (1 reviews)

VillageWalk at Lake Nona

$300Ks - $1Ms

VillageWalk at Lake Nona, Orlando, FL

Resale Only | Age-targeted | Built 2006 - 2016 | 1,300 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 (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 - $600Ks

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

1 2...3

The Villages®

$240,000

2 beds

2 baths

1,248 sq ft

Manufactured Home

518 SAINT ANDREWS BLVD, THE VILLAGES, FL...

Community: The Villages®

Breakaway Trails

180 BLACK HICKORY WAY, ORMOND BEACH, FL,..., Ormond Beach, FL 32174

$505,000

3 beds

2 baths

1,983 sq ft

House

180 BLACK HICKORY WAY, ORMOND BEACH, FL,...

Community: Breakaway Trails

Alhambra Villas Condominiums

239 N HILL AVE # 110, DELAND, FL, 32724, Deland, FL 32724

$199,000

2 beds

2 baths

1,091 sq ft

Condo

239 N HILL AVE # 110, DELAND, FL, 32724

Community: Alhambra Villas Condominiums

The Villages®

19201 SANDALWOOD DR # 19201, WILDWOOD, F..., Wildwood, FL 34785

$115,000

1 beds

1 baths

872 sq ft

Condo

19201 SANDALWOOD DR # 19201, WILDWOOD, F...

Community: The Villages®

Pelican Bay Daytona Beach

102 BOB WHITE CT C, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32119

$200,000

2 beds

2 baths

1,165 sq ft

House

102 BOB WHITE CT C, DAYTONA BEACH, FL, 3...

House

4239 DESKIN LN, THE VILLAGES, FL, 32163

Community: The Villages®

The Timbers at Everlands

1443 BLESSED ISLES DR NW, PALM BAY, FL, ..., Palm Bay, FL 32907

$493,145

4 beds

3 baths

2,638 sq ft

House

1443 BLESSED ISLES DR NW, PALM BAY, FL, ...

Community: The Timbers at Everlands

The Timbers at Everlands

1444 BLESSED ISLES DR NW, PALM BAY, FL, ..., Palm Bay, FL 32907

$472,983

3 beds

3 baths

2,583 sq ft

House

1444 BLESSED ISLES DR NW, PALM BAY, FL, ...

Community: The Timbers at Everlands

Latitude Margaritaville

546 MARGARITAVILLE AVE, DAYTONA BEACH, F..., Daytona Beach, FL 32124

$529,000

2 beds

2 baths

1,848 sq ft

House

546 MARGARITAVILLE AVE, DAYTONA BEACH, F...

Community: Latitude Margaritaville

Highland Fairways

2259 GRAND CYPRESS DR, LAKELAND, FL, 338..., Lakeland, FL 33810

$284,000

3 beds

2 baths

1,665 sq ft

House

2259 GRAND CYPRESS DR, LAKELAND, FL, 338...

Community: Highland Fairways

Pennbrooke Fairways

32512 OAK PARK DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$234,000

3 beds

2 baths

1,312 sq ft

House

32512 OAK PARK DR, LEESBURG, FL, 34748

Community: Pennbrooke Fairways

The Villages®

$269,900

2 beds

2 baths

1,186 sq ft

Villa

16966 SE 94TH SUNNYBROOK CIR, THE VILLAG...

House

2202 LANDREA LOOP, THE VILLAGES, FL, 321...

Community: The Villages®

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

Questions? Call us: (888) 625-4885

Scottish Highlands

1416 ORKNEY DR, LEESBURG, FL, 34788, Leesburg, FL 34788

$174,900

2 beds

2 baths

1,736 sq ft

House

1416 ORKNEY DR, LEESBURG, FL, 34788

Community: Scottish Highlands

Venetian Bay

3418 LEONARDO LN, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168

$625,250

3 beds

2 baths

1,912 sq ft

House

3418 LEONARDO LN, NEW SMYRNA BEACH, FL, ...

Community: Venetian Bay

Solivita

200 GRAND CANAL DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$209,000

2 beds

2 baths

1,388 sq ft

House

200 GRAND CANAL DR, KISSIMMEE, FL, 34759

Community: Solivita

Solivita

506 TAPATIO LN, POINCIANA, FL, 34759, Poinciana, FL 34759

$549,000

3 beds

3 baths

2,509 sq ft

House

506 TAPATIO LN, POINCIANA, FL, 34759

Community: Solivita

Royal Harbor

3592 TROPICAL SEAS LOOP, TAVARES, FL, 32..., Tavares, FL 32778

$329,000

2 beds

2 baths

1,452 sq ft

House

3592 TROPICAL SEAS LOOP, TAVARES, FL, 32...

Community: Royal Harbor

Royal Harbor

5740 BOUNTY CIR, TAVARES, FL, 32778, Tavares, FL 32778

$499,900

4 beds

3 baths

3,136 sq ft

House

5740 BOUNTY CIR, TAVARES, FL, 32778

Community: Royal Harbor

Lakeside Landings

10063 LAKE MIONA WAY, OXFORD, FL, 34484, Oxford, FL 34484

$439,800

3 beds

2 baths

2,066 sq ft

House

10063 LAKE MIONA WAY, OXFORD, FL, 34484

Community: Lakeside Landings

The Villages®

$926,000

3 beds

2 baths

2,465 sq ft

House

859 CHAPMAN LOOP, THE VILLAGES, FL, 3216...

Community: The Villages®

Stonecrest

10864 SE 171ST STREET RD, SUMMERFIELD, F..., Summerfield, FL 34491

$365,000

3 beds

2 baths

1,736 sq ft

House

10864 SE 171ST STREET RD, SUMMERFIELD, F...

Community: Stonecrest

The Villages®

$315,000

3 beds

2 baths

1,520 sq ft

House

3001 SAINT THOMAS LN, THE VILLAGES, FL, ...

House

17243 SE 116TH COURT RD, SUMMERFIELD, FL...

Community: Stonecrest

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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

1,248 sq ft

Manufactured Home

3 beds

2 baths

1,983 sq ft

House

2 beds

2 baths

1,091 sq ft

Condo

1 beds

1 baths

872 sq ft

Condo

2 beds

2 baths

1,165 sq ft

House

2 beds

2 baths

1,309 sq ft

House

2 beds

2 baths

1,158 sq ft

House

2 beds

2 baths

1,281 sq ft

Condo

3 beds

2 baths

1,925 sq ft

House

4 beds

3 baths

2,638 sq ft

House

3 beds

3 baths

2,583 sq ft

House

2 beds

2 baths

1,848 sq ft

House

3 beds

2 baths

1,665 sq ft

House

3 beds

2 baths

1,312 sq ft

House

2 beds

2 baths

1,186 sq ft

Villa

3 beds

2 baths

1,922 sq ft

House

3 beds

2 baths

2,236 sq ft

House

2 beds

2 baths

1,579 sq ft

House

3 beds

2 baths

1,769 sq ft

Villa

2 beds