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

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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 - $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

309 STONINGTON WAY, DELAND, FL, 32724

Community: Cresswind at Victoria Gardens

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Questions? Call us: (888) 625-4885

Del Webb Orlando

710 ASTURIAS RD, DAVENPORT, FL, 33837, Davenport, FL 33837

$450,000

2 beds

2 baths

2,080 sq ft

House

710 ASTURIAS RD, DAVENPORT, FL, 33837

Community: Del Webb Orlando

Venetian Bay

3057 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168

$309,900

3 beds

3 baths

1,614 sq ft

Townhouse

3057 MELETO BLVD, NEW SMYRNA BEACH, FL, ...

Community: Venetian Bay

The Villages®

$425,000

3 beds

2 baths

1,931 sq ft

House

17270 SE 94TH COULTS CIR, THE VILLAGES, ...

Community: The Villages®

The Villages®

$510,000

3 beds

2 baths

1,995 sq ft

House

16822 SE 80TH BELLAVISTA CIR, THE VILLAG...

Community: The Villages®

The Villages®

$409,000

2 beds

2 baths

1,094 sq ft

Villa

1314 LAJOLLA CIR, THE VILLAGES, FL, 3215...

Community: The Villages®

Pennbrooke Fairways

32752 TIMBERWOOD DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$329,900

3 beds

2 baths

1,940 sq ft

House

32752 TIMBERWOOD DR, LEESBURG, FL, 34748

Community: Pennbrooke Fairways

Del Webb Orlando

145 DEL SOL AVE, DAVENPORT, FL, 33837, Davenport, FL 33837

$439,900

3 beds

2 baths

1,972 sq ft

House

145 DEL SOL AVE, DAVENPORT, FL, 33837

Community: Del Webb Orlando

Legacy of Leesburg

27123 NOSTALGIA DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$299,900

3 beds

2 baths

1,477 sq ft

House

27123 NOSTALGIA DR, LEESBURG, FL, 34748

Community: Legacy of Leesburg

Plantation Bay Golf & Country Club

680 ELK RIVER DR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174

$489,900

3 beds

2 baths

1,678 sq ft

House

680 ELK RIVER DR, ORMOND BEACH, FL, 3217...

Community: Plantation Bay Golf & Country Club

Spruce Creek Country Club

12855 SE 92ND COURT RD, SUMMERFIELD, FL,..., Summerfield, FL 34491

$363,000

2 beds

2 baths

1,995 sq ft

House

12855 SE 92ND COURT RD, SUMMERFIELD, FL,...

Community: Spruce Creek Country Club

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Questions? Call us: (888) 625-4885

Spruce Creek Country Club

13885 DEL WEBB BLVD, SUMMERFIELD, FL, 34..., Summerfield, FL 34491

$410,000

3 beds

2 baths

2,213 sq ft

House

13885 DEL WEBB BLVD, SUMMERFIELD, FL, 34...

Community: Spruce Creek Country Club

The Villages®

$689,000

3 beds

3 baths

2,478 sq ft

House

8690 SE 173RD WISTERIA ST, THE VILLAGES,...

Community: The Villages®

The Villages®

$375,000

2 beds

2 baths

1,210 sq ft

Villa

1135 EASLEY WAY, THE VILLAGES, FL, 32162

Community: The Villages®

Trilogy® Orlando

135 CREPE MYRTLE DR, GROVELAND, FL, 3473..., Groveland, FL 34736

$365,000

3 beds

2 baths

1,651 sq ft

House

135 CREPE MYRTLE DR, GROVELAND, FL, 3473...

Community: Trilogy® Orlando

The Villages®

$297,400

2 beds

2 baths

1,156 sq ft

House

3243 MANSFIELD ST, THE VILLAGES, FL, 321...

Community: The Villages®

The Villages®

$895,000

3 beds

2 baths

3,466 sq ft

House

2935 CEDAR GROVE LOOP, THE VILLAGES, FL,...

Community: The Villages®

The Villages®

$815,000

3 beds

2 baths

2,060 sq ft

House

987 FREDERICK TER, THE VILLAGES, FL, 321...

Community: The Villages®

The Villages®

$299,900

2 beds

2 baths

1,818 sq ft

House

318 DEL MAR DR, THE VILLAGES, FL, 32159

Community: The Villages®

Spruce Creek South

9509 SE 173RD LN, SUMMERFIELD, FL, 34491, Summerfield, FL 34491

$227,900

2 beds

2 baths

1,248 sq ft

House

9509 SE 173RD LN, SUMMERFIELD, FL, 34491

Community: Spruce Creek South

The Villages®

$379,000

3 beds

2 baths

1,527 sq ft

House

17453 SE 76TH FLINTLOCK TER, THE VILLAGE...

Community: The Villages®

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Spruce Creek South

10035 SE 175TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$239,000

2 beds

2 baths

1,359 sq ft

Villa

10035 SE 175TH ST, SUMMERFIELD, FL, 3449...

Community: Spruce Creek South

The Villages®

$698,000

3 beds

2 baths

2,579 sq ft

House

1865 CLAVERTON ST, THE VILLAGES, FL, 321...

Community: The Villages®

Halifax Plantation

2967 ARRANMORE DR, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174

$739,000

4 beds

4 baths

3,221 sq ft

House

2967 ARRANMORE DR, ORMOND BEACH, FL, 321...

Community: Halifax Plantation

The Villages®

$319,000

3 beds

2 baths

1,512 sq ft

House

7168 SE 173RD ARLINGTON LOOP, THE VILLAG...

Community: The Villages®

Four Seasons at Orlando

2160 ANTILLES CLUB DR, KISSIMMEE, FL, 34..., Kissimmee, FL 34747

$379,990

2 beds

2 baths

1,778 sq ft

House

2160 ANTILLES CLUB DR, KISSIMMEE, FL, 34...

Community: Four Seasons at Orlando

Pelican Bay Daytona Beach

144 GREBE CT, DAYTONA BEACH, FL, 32119, Daytona Beach, FL 32119

$300,000

2 beds

2 baths

1,700 sq ft

House

144 GREBE CT, DAYTONA BEACH, FL, 32119

Community: Pelican Bay Daytona Beach

Cresswind at Victoria Gardens

1128 HERON POINT WAY, DELAND, FL, 32724, Deland, FL 32724

$577,500

2 beds

3 baths

2,670 sq ft

House

1128 HERON POINT WAY, DELAND, FL, 32724

Community: Cresswind at Victoria Gardens

The Villages®

$629,000

3 beds

3 baths

1,905 sq ft

House

555 RANDALL RD, THE VILLAGES, FL, 32163

Community: The Villages®

Stonecrest

17424 SE 111TH AVE, SUMMERFIELD, FL, 344..., Summerfield, FL 34491

$304,900

3 beds

2 baths

1,446 sq ft

House

17424 SE 111TH AVE, SUMMERFIELD, FL, 344...

Community: Stonecrest

Highland Fairways

1836 PRAIRIE DUNES CIR, LAKELAND, FL, 33..., Lakeland, FL 33810

$245,000

2 beds

2 baths

1,545 sq ft

House

1836 PRAIRIE DUNES CIR, LAKELAND, FL, 33...

House

17789 SE 113TH TER, SUMMERFIELD, FL, 344...

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

3 beds

2 baths

1,898 sq ft

House

2 beds

2 baths

1,198 sq ft

Villa

3 beds

2 baths

1,905 sq ft

House

3 beds

2 baths

2,182 sq ft

House

3 beds

2 baths

1,480 sq ft

House

2 beds

2 baths

2,080 sq ft

House

3 beds

3 baths

1,614 sq ft

Townhouse

3 beds

2 baths

1,931 sq ft

House

3 beds

2 baths

1,995 sq ft

House

2 beds

2 baths

1,094 sq ft

Villa

3 beds

2 baths

1,940 sq ft

House

3 beds

2 baths

1,972 sq ft

House

3 beds

2 baths

1,477 sq ft

House

3 beds

2 baths

1,678 sq ft

House

2 beds

2 baths

1,995 sq ft

House

3 beds

2 baths

2,213 sq ft

House

3 beds

3 baths

2,478 sq ft

House

2 beds

2 baths

1,210 sq ft

Villa

3 beds

2 baths

1,651 sq ft

House

2 beds