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

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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 - $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

Traditions at Lake Ruby

3998 BEDFORD AVE, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884

$464,900

4 beds

3 baths

2,277 sq ft

House

3998 BEDFORD AVE, WINTER HAVEN, FL, 3388...

Community: Traditions at Lake Ruby

Del Webb Sunbridge

3112 RANGER DR, SAINT CLOUD, FL, 34771, Saint Cloud, FL 34771

$612,000

5 beds

4 baths

2,995 sq ft

House

3112 RANGER DR, SAINT CLOUD, FL, 34771

777 VINEYARD WAY, POINCIANA, FL, 34759

House

458 JUNGLE PLUM WAY, THE VILLAGES, FL, 3...

Community: The Villages®

Heritage Isle

2981 ANZA ST, MELBOURNE, FL, 32940, Melbourne, FL 32940

$450,000

3 beds

2 baths

1,779 sq ft

House

2981 ANZA ST, MELBOURNE, FL, 32940

Community: Heritage Isle

Esplanade at Highland Ranch

1023 TIMBERVALE TRL, CLERMONT, FL, 34715, Clermont, FL 34715

$529,995

3 beds

3 baths

2,287 sq ft

House

1023 TIMBERVALE TRL, CLERMONT, FL, 34715

Community: Esplanade at Highland Ranch

Cresswind at Victoria Gardens

404 TISBURY CT, DELAND, FL, 32724, Deland, FL 32724

$359,000

2 beds

2 baths

1,512 sq ft

House

404 TISBURY CT, DELAND, FL, 32724

Community: Cresswind at Victoria Gardens

The Villages®

1025 AVALON AVE, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$330,000

2 beds

2 baths

1,268 sq ft

Villa

1025 AVALON AVE, LADY LAKE, FL, 32159

Community: The Villages®

Harbor Hills Country Club

39023 GRIFFIN LNDG, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$564,900

3 beds

3 baths

2,833 sq ft

House

39023 GRIFFIN LNDG, LADY LAKE, FL, 32159

Community: Harbor Hills Country Club

Ridgehaven

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

$289,935

3 beds

2 baths

1,454 sq ft

House

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

Community: Ridgehaven

The Villages®

1725 HILTON HEAD BLVD, LADY LAKE, FL, 32..., Lady Lake, FL 32159

$174,000

2 beds

2 baths

1,092 sq ft

Manufactured Home

1725 HILTON HEAD BLVD, LADY LAKE, FL, 32...

Community: The Villages®

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

Questions? Call us: (888) 625-4885

VillageWalk at Lake Nona

12232 PESCARA LN, ORLANDO, FL, 32827, Orlando, FL 32827

$469,900

3 beds

2 baths

1,708 sq ft

Villa

12232 PESCARA LN, ORLANDO, FL, 32827

Community: VillageWalk at Lake Nona

Sullivan Ranch

30021 DONNINGTON LOOP, MOUNT DORA, FL, 3..., Mount Dora, FL 32757

$450,000

4 beds

2 baths

2,164 sq ft

House

30021 DONNINGTON LOOP, MOUNT DORA, FL, 3...

Community: Sullivan Ranch

Sullivan Ranch

21612 BELGIAN CT, MOUNT DORA, FL, 32757, Mount Dora, FL 32757

$315,000

3 beds

2 baths

1,663 sq ft

House

21612 BELGIAN CT, MOUNT DORA, FL, 32757

Community: Sullivan Ranch

Spruce Creek South

17831 SE 96TH AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$214,999

2 beds

2 baths

1,118 sq ft

House

17831 SE 96TH AVE, SUMMERFIELD, FL, 3449...

Community: Spruce Creek South

Royal Harbor

5446 SEA LEOPARD ST, TAVARES, FL, 32778, Tavares, FL 32778

$359,000

2 beds

2 baths

1,848 sq ft

House

5446 SEA LEOPARD ST, TAVARES, FL, 32778

Community: Royal Harbor

Arlington Ridge

26931 CAMERONS RUN, LEESBURG, FL, 34748, Leesburg, FL 34748

$389,000

3 beds

2 baths

1,832 sq ft

House

26931 CAMERONS RUN, LEESBURG, FL, 34748

Community: Arlington Ridge

Spruce Creek Country Club

13195 SE 93RD CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$389,000

3 beds

3 baths

2,266 sq ft

House

13195 SE 93RD CIR, SUMMERFIELD, FL, 3449...

Community: Spruce Creek Country Club

Pelican Bay Daytona Beach

104 SHEARWATER WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32119

$300,000

3 beds

3 baths

2,107 sq ft

Villa

104 SHEARWATER WAY, DAYTONA BEACH, FL, 3...

Community: Pelican Bay Daytona Beach

Plantation Bay Golf & Country Club

18 TREETOP CIR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$330,000

2 beds

3 baths

2,828 sq ft

House

18 TREETOP CIR, ORMOND BEACH, FL, 32174

Community: Plantation Bay Golf & Country Club

Colonnades

4904 GOLDENVIEW LN, LAKELAND, FL, 33811, Lakeland, FL 33811

$240,000

2 beds

2 baths

1,523 sq ft

House

4904 GOLDENVIEW LN, LAKELAND, FL, 33811

Community: Colonnades

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

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Plantation at Leesburg

25273 LOST OAK CIR, LEESBURG, FL, 34748, Leesburg, FL 34748

$310,000

3 beds

2 baths

1,702 sq ft

House

25273 LOST OAK CIR, LEESBURG, FL, 34748

Community: Plantation at Leesburg

The Villages®

$350,000

3 beds

2 baths

1,632 sq ft

House

828 SILVER OAK AVE, THE VILLAGES, FL, 32...

Community: The Villages®

Traditions at Lake Ruby

3020 CANEEL ST, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884

$219,900

2 beds

2 baths

1,521 sq ft

Villa

3020 CANEEL ST, WINTER HAVEN, FL, 33884

Community: Traditions at Lake Ruby

Lake Ashton

2204 ASHTON PALMS DR # 2204, LAKE WALES,..., Lake Wales, FL 33859

$250,000

3 beds

2 baths

1,362 sq ft

Condo

2204 ASHTON PALMS DR # 2204, LAKE WALES,...

Community: Lake Ashton

The Villages®

$309,500

2 beds

2 baths

1,516 sq ft

House

17700 SE 92ND GRANTHAM TER, THE VILLAGES...

Community: The Villages®

The Villages®

$362,750

3 beds

2 baths

1,631 sq ft

House

4634 RAMSELL RD, THE VILLAGES, FL, 32163

Community: The Villages®

The Villages®

$399,900

3 beds

2 baths

1,733 sq ft

Villa

17720 SE 84TH PEYTON CT, THE VILLAGES, F...

Community: The Villages®

Grand Haven

10 S WATERVIEW DR, PALM COAST, FL, 32137, Palm Coast, FL 32137

$819,000

3 beds

3 baths

2,643 sq ft

House

10 S WATERVIEW DR, PALM COAST, FL, 32137

Community: Grand Haven

Spruce Creek Country Club

13660 SE 90TH TER, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$399,900

2 beds

2 baths

2,109 sq ft

House

13660 SE 90TH TER, SUMMERFIELD, FL, 3449...

Community: Spruce Creek Country Club

Legacy of Leesburg

5107 AURORA DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$317,000

3 beds

2 baths

1,658 sq ft

House

5107 AURORA DR, LEESBURG, FL, 34748

Community: Legacy of Leesburg

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10 CARRIAGE CREEK WAY, ORMOND BEACH, FL,...

Community: Breakaway Trails

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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

4 beds

3 baths

2,277 sq ft

House

5 beds

4 baths

2,995 sq ft

House

4 beds

4 baths

2,308 sq ft

House

3 beds

4 baths

2,542 sq ft

House

2 beds

2 baths

1,392 sq ft

House

2 beds

2 baths

1,530 sq ft

House

2 beds

2 baths

1,151 sq ft

Villa

3 beds

2 baths

1,830 sq ft

House

3 beds

2 baths

1,779 sq ft

House

3 beds

3 baths

2,287 sq ft

House

2 beds

2 baths

1,512 sq ft

House

2 beds

2 baths

1,268 sq ft

Villa

3 beds

3 baths

2,833 sq ft

House

3 beds

2 baths

1,454 sq ft

House

2 beds

2 baths

1,092 sq ft

Manufactured Home

3 beds

2 baths

1,708 sq ft

Villa

4 beds

2 baths

2,164 sq ft

House

3 beds

2 baths

1,663 sq ft

House

2 beds

2 baths

1,118 sq ft

House

2 beds