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

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

Heritage Isle

3541 FUNSTON CIR, MELBOURNE, FL, 32940, Melbourne, FL 32940

$319,000

2 beds

2 baths

1,407 sq ft

Townhouse

3541 FUNSTON CIR, MELBOURNE, FL, 32940

Community: Heritage Isle

Venetian Bay

3606 MARIBELLA DR, NEW SMYRNA BEACH, FL,..., New Smyrna Beach, FL 32168

$769,900

3 beds

3 baths

2,460 sq ft

House

3606 MARIBELLA DR, NEW SMYRNA BEACH, FL,...

Community: Venetian Bay

Bridgewater at Viera

1972 GREAT BELT CIR, MELBOURNE, FL, 3294..., Melbourne, FL 32940

$434,900

2 beds

2 baths

1,903 sq ft

House

1972 GREAT BELT CIR, MELBOURNE, FL, 3294...

Community: Bridgewater at Viera

Pelican Bay Daytona Beach

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

$200,000

2 beds

2 baths

1,165 sq ft

Condo

102 BOB WHITE CT # 102C, DAYTONA BEACH, ...

Community: Pelican Bay Daytona Beach

The Villages®

$265,900

1 beds

1 baths

875 sq ft

Villa

420 CANTERBURY CT, THE VILLAGES, FL, 321...

Community: The Villages®

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Questions? Call us: (888) 625-4885

Lakes at Laurel Highlands

2043 BLUE HIGHLANDS DR, LAKELAND, FL, 33..., Lakeland, FL 33811

$342,000

4 beds

2 baths

1,867 sq ft

House

2043 BLUE HIGHLANDS DR, LAKELAND, FL, 33...

Community: Lakes at Laurel Highlands

Solivita

759 LARGO PASS, POINCIANA, FL, 34759, Poinciana, FL 34759

$380,999

2 beds

2 baths

2,038 sq ft

House

759 LARGO PASS, POINCIANA, FL, 34759

3305 BALTIC SEA BLVD, TAVARES, FL, 32778

Community: Royal Harbor

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Venetian Bay

706 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168

$399,990

3 beds

3 baths

2,125 sq ft

House

706 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ...

Community: Venetian Bay

Spruce Creek Country Club

9019 SE 120TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491

$444,900

3 beds

2 baths

2,419 sq ft

House

9019 SE 120TH LOOP, SUMMERFIELD, FL, 344...

Community: Spruce Creek Country Club

Alhambra Villas Condominiums

151 N HILL AVE # 100, DELAND, FL, 32724, Deland, FL 32724

$165,000

2 beds

2 baths

979 sq ft

Condo

151 N HILL AVE # 100, DELAND, FL, 32724

Community: Alhambra Villas Condominiums

The Villages®

$365,900

3 beds

2 baths

1,475 sq ft

House

16850 SE 86TH DEPTFORD CT, THE VILLAGES,...

Community: The Villages®

Pelican Bay Daytona Beach

236 GULL DR, DAYTONA BEACH, FL, 32119, Daytona Beach, FL 32119

$315,000

2 beds

2 baths

2,100 sq ft

House

236 GULL DR, DAYTONA BEACH, FL, 32119

Community: Pelican Bay Daytona Beach

The Lakes at Harmony

7480 WING SPAN WAY, HARMONY, FL, 34773, Harmony, FL 34773

$540,000

5 beds

4 baths

2,717 sq ft

House

7480 WING SPAN WAY, HARMONY, FL, 34773

Community: The Lakes at Harmony

Spruce Creek Country Club

12150 SE 91ST TER, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$349,000

2 beds

2 baths

1,870 sq ft

House

12150 SE 91ST TER, SUMMERFIELD, FL, 3449...

Community: Spruce Creek Country Club

Enclave at VillageWalk

11741 SAVONA WAY, ORLANDO, FL, 32827, Orlando, FL 32827

$1,100,000

4 beds

4 baths

3,197 sq ft

House

11741 SAVONA WAY, ORLANDO, FL, 32827

Community: Enclave at VillageWalk

Spruce Creek Country Club

12592 SE 97TH TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491

$475,000

3 beds

2 baths

2,413 sq ft

House

12592 SE 97TH TERRACE RD, SUMMERFIELD, F...

Community: Spruce Creek Country Club

Grand Haven

455 RIVERFRONT DR UNIT A303, PALM COAST,..., Palm Coast, FL 32137

$799,000

3 beds

2 baths

1,760 sq ft

Condo

455 RIVERFRONT DR UNIT A303, PALM COAST,...

Community: Grand Haven

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Pennbrooke Fairways

32676 OAK PARK DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$270,000

3 beds

2 baths

1,709 sq ft

House

32676 OAK PARK DR, LEESBURG, FL, 34748

Community: Pennbrooke Fairways

The Villages®

1717 LILLY LN, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$255,000

2 beds

2 baths

1,856 sq ft

Manufactured Home

1717 LILLY LN, LADY LAKE, FL, 32159

Community: The Villages®

The Villages®

1222 ZAPATA PL, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$185,000

2 beds

1 baths

936 sq ft

Manufactured Home

1222 ZAPATA PL, LADY LAKE, FL, 32159

Community: The Villages®

The Savannahs

4174 CALADIUM CIR, WEST MELBOURNE, FL, 3..., West Melbourne, FL 32904

$409,000

3 beds

2 baths

1,812 sq ft

House

4174 CALADIUM CIR, WEST MELBOURNE, FL, 3...

Community: The Savannahs

Alamanda Key

$485,000

3 beds

2 baths

1,782 sq ft

House

3790 ALAMANDA KEY DR, MELBOURNE, FL, 329...

Community: Alamanda Key

Venetian Bay

424 LUNA BELLA LN 432, NEW SMYRNA BEACH,..., New Smyrna Beach, FL 32168

$319,900

3 beds

2 baths

1,753 sq ft

Condo

424 LUNA BELLA LN 432, NEW SMYRNA BEACH,...

Community: Venetian Bay

Spruce Creek South

17728 SE 97TH AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$220,000

2 beds

2 baths

1,550 sq ft

House

17728 SE 97TH AVE, SUMMERFIELD, FL, 3449...

Community: Spruce Creek South

The Villages®

$409,000

3 beds

2 baths

1,512 sq ft

House

849 YEMASSEE LOOP, THE VILLAGES, FL, 321...

Community: The Villages®

Solivita

201 LARGO DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$444,000

2 beds

2 baths

2,419 sq ft

House

201 LARGO DR, KISSIMMEE, FL, 34759

Community: Solivita

Plantation at Leesburg

25533 BELLE HELENE, LEESBURG, FL, 34748, Leesburg, FL 34748

$225,000

2 beds

2 baths

1,352 sq ft

Manufactured Home

25533 BELLE HELENE, LEESBURG, FL, 34748

House

221 ISLAND BREEZE AVE, DAYTONA BEACH, FL...

Community: Latitude Margaritaville

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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

1,407 sq ft

Townhouse

3 beds

3 baths

2,460 sq ft

House

2 beds

2 baths

1,903 sq ft

House

2 beds

2 baths

1,165 sq ft

Condo

1 beds

1 baths

875 sq ft

Villa

4 beds

2 baths

1,867 sq ft

House

2 beds

2 baths

2,038 sq ft

House

4 beds

3 baths

2,421 sq ft

House

3 beds

2 baths

1,860 sq ft

House

3 beds

2 baths

2,037 sq ft

House

3 beds

2 baths

1,816 sq ft

House

3 beds

2 baths

1,851 sq ft

House

3 beds

2 baths

1,613 sq ft

House

3 beds

2 baths

1,773 sq ft

House

3 beds

3 baths

2,108 sq ft

House

3 beds

3 baths

2,125 sq ft

House

3 beds

2 baths

2,419 sq ft

House

2 beds

2 baths

979 sq ft

Condo

3 beds

2 baths

1,475 sq ft

House

2 beds