Winter Park, FL 55+ active adult communities & homes for sale

2,414 homes near Winter Park

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4 rating (17 reviews)

The Villages®

$100ks - $1Ms

The Villages®, The Villages, FL

New and Resale | 55+ age-restricted | Built 1978 - present | 70,000 homes

4.7 rating (18 reviews)

Solivita

$300ks - $700ks

Solivita, Kissimmee, FL

New and Resale | 55+ age-restricted | Built 2000 - present | 5,900 homes

4.5 rating (11 reviews)

Spruce Creek Country Club

$100ks - $400ks

Spruce Creek Country Club, Summerfield, FL

Resale Only | 55+ age-restricted | Built 1996 - 2007 | 3,250 homes

5 rating (2 reviews)

Plantation at Leesburg

$100ks - $300ks

Plantation at Leesburg, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1987 - 2008 | 2,820 homes

3.6 rating (48 reviews)

Latitude Margaritaville

$300ks - $800ks

Latitude Margaritaville, Daytona Beach, FL

Resale Only | 55+ age-restricted | Built 2017 - 2025 | 3,900 homes

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5 rating (1 reviews)

Plantation Bay Golf &...

$400ks - $2Ms

Plantation Bay Golf &..., Ormond Beach, FL

New and Resale | Age-targeted | Built 1988 - present | 3,500 homes

Venetian Bay

$300ks - $1Ms

Venetian Bay, New Smyrna Beach, FL

New and Resale | Age-targeted | Built 2004 - present | 1,561 homes

5 rating (3 reviews)

Lake Ashton

$200ks - $500ks

Lake Ashton, Lake Wales, FL

Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 homes

5 rating (3 reviews)

Stonecrest

$200ks - $500ks

Stonecrest, Summerfield, FL

Resale Only | 55+ age-restricted | Built 1990 - 2024 | 2,224 homes

Grand Haven

$200ks - $800ks

Grand Haven, Palm Coast, FL

New and Resale | Age-targeted | Built 1997 - present | 1,901 homes

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2.8 rating (6 reviews)

Arlington Ridge

$200ks - $500ks

Arlington Ridge, Leesburg, FL

New and Resale | 55+ age-restricted | Built 2005 - present | 629 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 (3 reviews)

Twin Lakes

$200ks - $600ks

Twin Lakes, St. Cloud, FL

New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes

5 rating (8 reviews)

Royal Highlands

$200ks - $400ks

Royal Highlands, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 homes

5 rating (7 reviews)

Kings Ridge

$200ks - $400ks

Kings Ridge, Clermont, FL

Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 homes

3.8 rating (4 reviews)

Spruce Creek South

$100ks - $200ks

Spruce Creek South, Summerfield, FL

Resale Only | 55+ age-restricted | Built 1989 - 1995 | 1,650 homes

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Questions? Call us: (888) 625-4885

Pelican Bay Daytona Beach

$100ks - $600ks

Pelican Bay Daytona Beach, Daytona Beach, FL

Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 homes

Halifax Plantation

$300ks - $1Ms

Halifax Plantation, Ormond Beach, FL

New and Resale | Age-targeted | Built 1980 - present | 1,000 homes

5 rating (1 reviews)

Sandpiper Golf & Coun...

$100ks - $300ks

Sandpiper Golf & Coun..., Lakeland, FL

New and Resale | 55+ age-restricted | Built 1985 - present | 1,193 homes

4 rating (4 reviews)

Lakes of Mount Dora

$300ks - $1Ms

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

$300ks - $900ks

Harbor Hills Country Club, Lady Lake, FL

New and Resale | Age-targeted | Built 1989 - present | 940 homes

3.6 rating (5 reviews)

Heritage Hills

$200ks - $400ks

Heritage Hills, Clermont, FL

New and Resale | 55+ age-restricted | Built 2006 - present | 1,154 homes

5 rating (1 reviews)

Del Webb Sunbridge

$400ks - $800ks

Del Webb Sunbridge, St. Cloud, FL

New and Resale | 55+ age-restricted | Built 2019 - present | 1,300 homes

5 rating (1 reviews)

Cresswind at Victoria Gar...

$200ks - $500ks

Cresswind at Victoria Gar..., DeLand, FL

Resale Only | 55+ age-restricted | Built 2001 - 2022 | 1,070 homes

Summer Trees

$200ks - $400ks

Summer Trees, Port Orange, FL

Resale Only | 55+ age-restricted | Built 1976 - 2005 | 500 homes

The Lakes at Harmony

$200ks - $400ks

The Lakes at Harmony, Harmony, FL

New and Resale | 55+ age-restricted | Built 2016 - present | 400 homes

5 rating (1 reviews)

Royal Harbor

$200ks - $800ks

Royal Harbor, Tavares, FL

Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 homes

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Questions? Call us: (888) 625-4885

5 rating (2 reviews)

Heritage Isle

$300ks - $500ks

Heritage Isle, Viera, FL

Resale Only | 55+ age-restricted | Built 2005 - 2017 | 1,500 homes

5 rating (8 reviews)

Pennbrooke Fairways

<$100k - $300ks

Pennbrooke Fairways, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 homes

Breakaway Trails

$400ks - $800ks

Breakaway Trails, Ormond Beach, FL

New and Resale | Age-targeted | Built 1985 - present | 976 homes

Four Seasons at Orlando

$300ks - $600ks

Four Seasons at Orlando, Kissimmee, FL

New Construction | 55+ age-restricted | Built 2017 - present | 557 homes

Ridgehaven

$300ks - $600ks

Ridgehaven, Ormond Beach, FL

New Construction | 55+ age-restricted

Scottish Highlands

$100ks - $200ks

Scottish Highlands, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1983 - 1992 | 653 homes

4.8 rating (6 reviews)

Highland Lakes

$100ks - $200ks

Highland Lakes, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes

1 rating (1 reviews)

Sullivan Ranch

$200ks - $500ks

Sullivan Ranch, Mount Dora, FL

Resale Only | 55+ age-restricted | Built 2005 - 2020 | 692 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

5 rating (1 reviews)

VillageWalk at Lake Nona

$300ks - $700ks

VillageWalk at Lake Nona, Orlando, FL

Resale Only | Age-targeted | Built 2006 - 2016 | 1,300 homes

Foxwood Lake Estates

$100ks - $200ks

Foxwood Lake Estates, Lakeland, FL

Resale Only | 55+ age-restricted | Built 1982 - 1987 | 545 homes

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

Questions? Call us: (888) 625-4885

4.4 rating (16 reviews)

Del Webb Orlando

$200ks - $500ks

Del Webb Orlando, Davenport, FL

Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes

5 rating (2 reviews)

Bridgewater at Viera

$300ks - $800ks

Bridgewater at Viera, Melbourne, FL

Resale Only | 55+ age-restricted | Built 2017 - 2023 | 870 homes

1033 OAK FOREST DR, THE VILLAGES, FL, 32...

House

2047 DUNSTER CT, THE VILLAGES, FL, 32162

Community: The Villages®

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Questions? Call us: (888) 625-4885

New The Villages®

1577 BLYTHEWOOD LOOP, THE VILLAGES, FL, ..., The Villages, FL 32162

$398,000

3 beds

2 baths

1,513 sq ft

House

1577 BLYTHEWOOD LOOP, THE VILLAGES, FL, ...

Community: The Villages®

New Kings Ridge

3525 ROLLINGBROOK ST, CLERMONT, FL, 3471..., Clermont, FL 34711

$328,900

2 beds

2 baths

1,548 sq ft

House

3525 ROLLINGBROOK ST, CLERMONT, FL, 3471...

Community: Kings Ridge

New Plantation at Leesburg

5000 SAWGRASS LAKE CIR, LEESBURG, FL, 34..., Leesburg, FL 34748

$284,900

2 beds

2 baths

1,775 sq ft

House

5000 SAWGRASS LAKE CIR, LEESBURG, FL, 34...

Community: Plantation at Leesburg

New Royal Harbor

2880 MEDITERRANEAN LOOP, TAVARES, FL, 32..., Tavares, FL 32778

$347,500

3 beds

2 baths

2,189 sq ft

House

2880 MEDITERRANEAN LOOP, TAVARES, FL, 32...

Community: Royal Harbor

New Royal Harbor

3257 BALTIC SEA BLVD, TAVARES, FL, 32778, Tavares, FL 32778

$392,000

3 beds

3 baths

2,012 sq ft

House

3257 BALTIC SEA BLVD, TAVARES, FL, 32778

Community: Royal Harbor

New The Villages®

418 FLOSSMOOR CT, THE VILLAGES, FL, 3216..., The Villages, FL 32162

$420,000

3 beds

2 baths

1,685 sq ft

Villa

418 FLOSSMOOR CT, THE VILLAGES, FL, 3216...

Community: The Villages®

New Plantation at Leesburg

5030 EL DESTINO DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$233,000

2 beds

2 baths

1,308 sq ft

House

5030 EL DESTINO DR, LEESBURG, FL, 34748

Community: Plantation at Leesburg

New Plantation Bay Golf & Country Club

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

$597,500

3 beds

2 baths

1,873 sq ft

House

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

766 PELICAN BAY DR, DAYTONA BEACH, FL, 3...

Community: Pelican Bay Daytona Beach

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

Questions? Call us: (888) 625-4885

New The Villages®

1344 AUGUSTINE DR, THE VILLAGES, FL, 321..., The Villages, FL 32159

$482,000

3 beds

2 baths

1,954 sq ft

House

1344 AUGUSTINE DR, THE VILLAGES, FL, 321...

Community: The Villages®

New Plantation at Leesburg

26234 GLEN EAGLE DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$238,000

3 beds

2 baths

1,761 sq ft

House

26234 GLEN EAGLE DR, LEESBURG, FL, 34748

Community: Plantation at Leesburg

New Bridgewater at Viera

1763 GREAT BELT CIR, MELBOURNE, FL, 3294..., Melbourne, FL 32940

$475,000

2 beds

2 baths

1,903 sq ft

House

1763 GREAT BELT CIR, MELBOURNE, FL, 3294...

Community: Bridgewater at Viera

New Highland Lakes

26912 BECKER CT, LEESBURG, FL, 34748, Leesburg, FL 34748

$360,000

3 beds

2 baths

2,498 sq ft

House

26912 BECKER CT, LEESBURG, FL, 34748

Community: Highland Lakes

New The Villages®

923 MOSES LOOP, THE VILLAGES, FL, 32162, The Villages, FL 32162

$1,400,000

5 beds

4 baths

3,359 sq ft

House

923 MOSES LOOP, THE VILLAGES, FL, 32162

Community: The Villages®

New Plantation at Leesburg

4835 SABLE RIDGE CT, LEESBURG, FL, 34748, Leesburg, FL 34748

$305,000

3 beds

2 baths

1,818 sq ft

House

4835 SABLE RIDGE CT, LEESBURG, FL, 34748

Community: Plantation at Leesburg

New The Villages®

5609 HANCOCK DR, WILDWOOD, FL, 34785, Wildwood, FL 34785

$100,000

2 beds

1 baths

660 sq ft

Mobile Home

5609 HANCOCK DR, WILDWOOD, FL, 34785

Community: The Villages®

New Latitude Margaritaville

328 TIKI TER, DAYTONA BEACH, FL, 32124, Daytona Beach, FL 32124

$465,000

2 beds

2 baths

1,563 sq ft

House

328 TIKI TER, DAYTONA BEACH, FL, 32124

Community: Latitude Margaritaville

New Spruce Creek South

9532 SE 173RD LN, SUMMERFIELD, FL, 34491, Summerfield, FL 34491

$245,000

2 beds

2 baths

1,678 sq ft

House

9532 SE 173RD LN, SUMMERFIELD, FL, 34491

Community: Spruce Creek South

New The Villages®

1685 CAMPOS DR, THE VILLAGES, FL, 32162, The Villages, FL 32162

$265,000

2 beds

2 baths

1,121 sq ft

House

1685 CAMPOS DR, THE VILLAGES, FL, 32162

Community: The Villages®

New Heritage Hills

3644 SOLANA CIR F, CLERMONT, FL, 34711, Clermont, FL 34711

$275,000

2 beds

2 baths

1,503 sq ft

Villa

3644 SOLANA CIR F, CLERMONT, FL, 34711

Community: Heritage Hills

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

Questions? Call us: (888) 625-4885

New Pennbrooke Fairways

412 WESTWOOD DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$189,900

2 beds

2 baths

1,140 sq ft

House

412 WESTWOOD DR, LEESBURG, FL, 34748

Community: Pennbrooke Fairways

New Harbor Hills Country Club

5066 GREENS DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$649,000

4 beds

3 baths

2,544 sq ft

House

5066 GREENS DR, LADY LAKE, FL, 32159

Community: Harbor Hills Country Club

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Frequently Asked Questions

What size 55+ communities are there in Winter Park?

In Winter Park, there is 1 small community with less than 500 homes.

How many homes are there in the smallest, largest, and average 55+ communities in Winter Park?

The smallest 55+ community in Winter Park has 178 homes, the largest has 178 homes, and the average community consists of 178 homes.

Are there new 55+ homes available in Winter Park?

Yes, there is new 55+ home available in Winter Park. The most recent community started in Winter Park include Rosalia Winter Park. There is also 1 community in Winter Park that offers new construction homes, including Rosalia Winter Park.

Are there gated 55+ communities in Winter Park?

Yes, there is gated 55+ community in Winter Park. The only 55+ community in Winter Park is gated. For instance, Rosalia Winter Park is a gated community with 178 homes.

Want more information about active adult communities around Winter Park?

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2,414 homes

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Winter Park, FL 55+ active adult communities & homes for sale

93 communities near Winter Park

2,414 homes near Winter Park

2 beds

2 baths

1,910 sq ft

House

2 beds

2 baths

1,716 sq ft

House

3 beds

2 baths

1,931 sq ft

House

2 beds

2 baths

1,358 sq ft

Manufactured Home

3 beds

2 baths

1,840 sq ft

House

2 beds

2 baths

1,488 sq ft

House

3 beds

2 baths

1,392 sq ft

House

3 beds

2 baths

1,948 sq ft

House

3 beds

2 baths

2,236 sq ft

House

3 beds

2 baths

1,814 sq ft

House

2 beds

2 baths

1,295 sq ft

House

3 beds

2 baths

1,527 sq ft

House

4 beds

3 baths

2,378 sq ft

House

3 beds

2 baths

1,544 sq ft

House

2 beds

2 baths

1,819 sq ft

House

3 beds

2 baths

1,851 sq ft

House

3 beds

2 baths

1,513 sq ft

House

2 beds

2 baths

1,548 sq ft

House

2 beds

2 baths

1,775 sq ft

House

3 beds