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

98 communities 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

4.5 rating (19 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

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

Venetian Bay

$300ks - $1Ms

Venetian Bay, New Smyrna Beach, FL

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

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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

5 rating (3 reviews)

Stonecrest

$200ks - $500ks

Stonecrest, Summerfield, FL

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

5 rating (1 review)

Plantation Bay Golf & Cou...

$400ks - $2Ms

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

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

Pelican Bay Daytona Beach

$100ks - $600ks

Pelican Bay Daytona Beach, Daytona Beach, FL

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

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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

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 (8 reviews)

Royal Highlands

$200ks - $400ks

Royal Highlands, Leesburg, FL

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

Grand Haven

$200ks - $800ks

Grand Haven, Palm Coast, FL

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

5 rating (8 reviews)

Kings Ridge

$200ks - $400ks

Kings Ridge, Clermont, FL

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

5 rating (1 review)

Cresswind at Victoria Gar...

$300ks - $500ks

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

3.8 rating (6 reviews)

Trilogy® Orlando

$200ks - $500ks

Trilogy® Orlando, Groveland, FL

Resale Only | 55+ age-restricted | Built 2005 - 2022 | 1,500 homes

Halifax Plantation

$300ks - $1Ms

Halifax Plantation, Ormond Beach, FL

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

4 rating (4 reviews)

Lakes of Mount Dora

$300ks - $900ks

Lakes of Mount Dora, Mount Dora, FL

New and Resale | 55+ age-restricted | Built 2006 - present | 950 homes

5 rating (1 review)

Royal Harbor

$200ks - $800ks

Royal Harbor, Tavares, FL

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

2.8 rating (6 reviews)

Arlington Ridge

$200ks - $500ks

Arlington Ridge, Leesburg, FL

New and Resale | 55+ age-restricted | Built 2005 - present | 629 homes

5 rating (1 review)

Sandpiper Golf & Country ...

$100ks - $300ks

Sandpiper Golf & Country ..., Lakeland, FL

New and Resale | 55+ age-restricted | Built 1985 - present | 1,193 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 (8 reviews)

Pennbrooke Fairways

<$100k - $300ks

Pennbrooke Fairways, Leesburg, FL

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

5 rating (1 review)

Legacy of Leesburg

$200ks - $400ks

Legacy of Leesburg, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1999 - 2017 | 1,000 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

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

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Questions? Call us: (888) 625-4885

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

Scottish Highlands

$100ks - $200ks

Scottish Highlands, Leesburg, FL

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

5 rating (1 review)

Del Webb Sunbridge

$400ks - $800ks

Del Webb Sunbridge, St. Cloud, FL

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

4.8 rating (6 reviews)

Highland Lakes

$100ks - $200ks

Highland Lakes, Leesburg, FL

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

Heritage - The Cottages o...

$300ks

Heritage - The Cottages o..., Okahumpka, FL

New Construction | 55+ age-restricted | Built 2022 - present | 179 homes

Four Seasons at Orlando

$300ks - $600ks

Four Seasons at Orlando, Kissimmee, FL

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

Breakaway Trails

$400ks - $800ks

Breakaway Trails, Ormond Beach, FL

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

Gatherings of Lake Nona

$300ks - $400ks

Gatherings of Lake Nona, Orlando, FL

New and Resale | 55+ age-restricted | Built 2017 - present | 216 homes

Del Webb at Viera

$400ks - $1Ms

Del Webb at Viera, Melbourne, FL

New Construction | 55+ age-restricted | Built 2021 - present | 1,300 homes

Highland Fairways

$100ks - $300ks

Highland Fairways, Lakeland, FL

Resale Only | 55+ age-restricted | Built 1983 - 1998 | 660 homes

Lakeside Landings

$100ks - $300ks

Lakeside Landings, Oxford, FL

New and Resale | Age-targeted | Built 2005 - present | 700 homes

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

Questions? Call us: (888) 625-4885

1 rating (1 review)

Sullivan Ranch

$200ks - $500ks

Sullivan Ranch, Mount Dora, FL

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

The Lakes at Harmony

$200ks - $400ks

The Lakes at Harmony, Harmony, FL

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

1 2...3

The Villages®

$359,000

3 beds

2 baths

1,484 sq ft

Villa

2137 LOCKLIN LN, THE VILLAGES, FL, 32163

Community: The Villages®

Spruce Creek Country Club

9561 SE 124TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491

$329,900

2 beds

2 baths

1,652 sq ft

House

Community: Latitude Margaritaville

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Questions? Call us: (888) 625-4885

The Villages®

$349,900

2 beds

2 baths

1,258 sq ft

Villa

1075 BURNETTOWN PL, THE VILLAGES, FL, 32...

Community: The Villages®

The Villages®

$429,900

3 beds

2 baths

1,612 sq ft

Villa

2289 SWANSEA TER, THE VILLAGES, FL, 3216...

1339 LAJOLLA CIR, THE VILLAGES, FL, 3215...

1930 RHETT RD, THE VILLAGES, FL, 32163

Community: The Villages®

Baytree

615 JUNIPER WAY, TAVARES, FL, 32778, Tavares, FL 32778

$285,000

3 beds

2 baths

1,440 sq ft

House

615 JUNIPER WAY, TAVARES, FL, 32778

Community: Baytree

The Villages®

$299,900

3 beds

2 baths

1,392 sq ft

House

17648 SE 93RD BUTLER CT, THE VILLAGES, F...

Community: The Villages®

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Questions? Call us: (888) 625-4885

The Villages®

$269,900

2 beds

2 baths

1,344 sq ft

House

1707 GOMEZ PL, THE VILLAGES, FL, 32162

Community: The Villages®

Twin Lakes

2777 SOUTHLAND ST, ST CLOUD, FL, 34772, St Cloud, FL 34772

$550,000

3 beds

3 baths

2,365 sq ft

House

2777 SOUTHLAND ST, ST CLOUD, FL, 34772

Community: Twin Lakes

The Villages®

$349,900

2 beds

2 baths

1,146 sq ft

Villa

1214 SAN BERNARDO RD, THE VILLAGES, FL, ...

Community: The Villages®

The Villages®

4946 NE 124TH RD, OXFORD, FL, 34484, Oxford, FL 34484

$380,000

3 beds

3 baths

2,547 sq ft

House

4946 NE 124TH RD, OXFORD, FL, 34484

Community: The Villages®

Breakaway Trails

1 CROOKED BRIDGE WAY, ORMOND BEACH, FL, ..., Ormond Beach, FL 32174

$725,000

5 beds

3 baths

3,193 sq ft

House

House

7800 CHASE RD, LAKELAND, FL, 33810

The Villages®

$252,900

2 beds

2 baths

963 sq ft

House

6225 DINGMAN WAY, THE VILLAGES, FL, 3216...

Community: The Villages®

The Villages®

$349,000

2 beds

2 baths

1,100 sq ft

House

1019 GOLDEN GROVE DR, THE VILLAGES, FL, ...

Community: The Villages®

Latitude Margaritaville

121 SPONGECAKE DR, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32124

$689,900

2 beds

2 baths

1,681 sq ft

House

121 SPONGECAKE DR, DAYTONA BEACH, FL, 32...

Community: Latitude Margaritaville

Arlington Ridge

27040 CAMERONS RUN, LEESBURG, FL, 34748, Leesburg, FL 34748

$390,000

3 beds

2 baths

2,001 sq ft

House

27040 CAMERONS RUN, LEESBURG, FL, 34748

Community: Arlington Ridge

The Villages®

$379,900

3 beds

2 baths

1,982 sq ft

House

930 RAMOS DR, THE VILLAGES, FL, 32159

Community: The Villages®

Highland Lakes

26162 NEWCOMBE CIR, LEESBURG, FL, 34748, Leesburg, FL 34748

$252,000

2 beds

2 baths

1,440 sq ft

House

26162 NEWCOMBE CIR, LEESBURG, FL, 34748

Community: Highland Lakes

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

Questions? Call us: (888) 625-4885

The Villages®

$449,000

3 beds

2 baths

2,230 sq ft

House

460 LOMA PASEO DR, THE VILLAGES, FL, 321...

Community: The Villages®

The Villages®

$1,600,000

3 beds

2 baths

2,033 sq ft

House

3720 VINELAND AVE, THE VILLAGES, FL, 321...

Community: The Villages®

Frequently Asked Questions

What size 55+ communities are there in Winter Park?

Of the 1 55+ community in Winter Park, it is a rental. By size, 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.

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98 communities

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

98 communities near Winter Park

2,709 homes near Winter Park

3 beds

2 baths

1,484 sq ft

Villa

2 beds

2 baths

1,652 sq ft

House

3 beds

2 baths

2,680 sq ft

House

3 beds

2 baths

1,668 sq ft

House

2 beds

2 baths

1,308 sq ft

House

2 beds

2 baths

1,258 sq ft

Villa

3 beds

2 baths

1,612 sq ft

Villa

3 beds

2 baths

1,925 sq ft

House

3 beds

2 baths

1,553 sq ft

House

2 beds

2 baths

1,094 sq ft

Villa

2 beds

2 baths

1,574 sq ft

House

3 beds

2 baths

1,837 sq ft

Villa

2 beds

2 baths

1,121 sq ft

Villa

2 beds

2 baths

1,434 sq ft

Villa

3 beds

2 baths

1,440 sq ft

House

3 beds

2 baths

1,392 sq ft

House

2 beds

2 baths

1,344 sq ft

House

3 beds

3 baths

2,365 sq ft

House

2 beds

2 baths

1,146 sq ft

Villa

3 beds