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 (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

Venetian Bay

$300ks - $1Ms

Venetian Bay, New Smyrna Beach, FL

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

4.7 rating (18 reviews)

Solivita

$300ks - $700ks

Solivita, Kissimmee, FL

New and Resale | 55+ age-restricted | Built 2000 - present | 5,900 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 (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 reviews)

Plantation Bay Golf &...

$400ks - $2Ms

Plantation Bay Golf &..., 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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Grand Haven

$200ks - $800ks

Grand Haven, Palm Coast, FL

New and Resale | Age-targeted | Built 1997 - present | 1,901 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 (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 - $400ks

Royal Highlands, Leesburg, FL

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

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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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 - $900ks

Lakes of Mount Dora, Mount Dora, FL

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

Halifax Plantation

$300ks - $1Ms

Halifax Plantation, Ormond Beach, FL

New and Resale | Age-targeted | Built 1980 - present | 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

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)

Cresswind at Victoria Gar...

$300ks - $500ks

Cresswind at Victoria Gar..., DeLand, FL

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

Highland Fairways

$100ks - $300ks

Highland Fairways, Lakeland, FL

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

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Questions? Call us: (888) 625-4885

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)

Royal Harbor

$200ks - $800ks

Royal Harbor, Tavares, FL

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

Gatherings of Lake Nona

$300ks - $400ks

Gatherings of Lake Nona, Orlando, FL

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

Heritage - The Cottages o...

$300ks

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

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

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

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

Del Webb at Viera

$400ks - $1Ms

Del Webb at Viera, Melbourne, FL

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

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

Questions? Call us: (888) 625-4885

Lakeside Landings

$100ks - $300ks

Lakeside Landings, Oxford, FL

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

The Timbers at Everlands

$200ks - $500ks

The Timbers at Everlands, Palm Bay, FL

New Construction | 55+ age-restricted | Built 2023 - present | 450 homes

615 JUNIPER WAY, TAVARES, FL, 32778

Community: Baytree

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Questions? Call us: (888) 625-4885

The Villages®

$299,900

3 beds

2 baths

1,392 sq ft

House

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

Community: The Villages®

The Villages®

$279,900

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®

$359,900

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

$405,000

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

$765,000

5 beds

3 baths

3,193 sq ft

House

1 CROOKED BRIDGE WAY, ORMOND BEACH, FL, ...

Community: Breakaway Trails

Del Webb Sunbridge

2743 RIVER CREEK LN, ST CLOUD, FL, 34771, St Cloud, FL 34771

$648,500

3 beds

3 baths

2,321 sq ft

House

2743 RIVER CREEK LN, ST CLOUD, FL, 34771

Community: Del Webb Sunbridge

The Villages®

$269,900

2 beds

2 baths

1,188 sq ft

Villa

1806 QUEENSBURY TER, THE VILLAGES, FL, 3...

Community: The Villages®

Arlington Ridge

26669 OTTER CREEK LN, LEESBURG, FL, 3474..., Leesburg, FL 34748

$350,000

3 beds

2 baths

1,718 sq ft

House

26669 OTTER CREEK LN, LEESBURG, FL, 3474...

Community: Arlington Ridge

Stonecrest

12271 SE 175TH LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$396,000

4 beds

3 baths

2,246 sq ft

House

12271 SE 175TH LN, SUMMERFIELD, FL, 3449...

Community: Stonecrest

Trilogy® Orlando

615 CONSERVATION BLVD, GROVELAND, FL, 34..., Groveland, FL 34736

$349,900

2 beds

3 baths

2,009 sq ft

House

615 CONSERVATION BLVD, GROVELAND, FL, 34...

Villa

2015 PEACEFUL PL, THE VILLAGES, FL, 3216...

Community: The Villages®

New Pelican Bay Daytona Beach

101 BOB WHITE CT 101J, DAYTONA BEACH, FL..., Daytona Beach, FL 32119

$179,000

2 beds

2 baths

1,165 sq ft

House

101 BOB WHITE CT 101J, DAYTONA BEACH, FL...

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 Grand Haven

7 RIVER LANDING DR, PALM COAST, FL, 3213..., Palm Coast, FL 32137

$439,000

2 beds

3 baths

1,919 sq ft

Townhouse

7 RIVER LANDING DR, PALM COAST, FL, 3213...

Community: Grand Haven

New The Villages®

17198 SE 84TH KNIGHT AVE, THE VILLAGES, ..., The Villages, FL 32162

$415,000

3 beds

2 baths

1,568 sq ft

Villa

17198 SE 84TH KNIGHT AVE, THE VILLAGES, ...

Community: The Villages®

New The Villages®

4236 YARDHAM TER, THE VILLAGES, FL, 3216..., The Villages, FL 32163

$599,000

3 beds

2 baths

2,400 sq ft

House

4236 YARDHAM TER, THE VILLAGES, FL, 3216...

Community: The Villages®

New Grand Haven

38 FRONT ST, PALM COAST, FL, 32137, Palm Coast, FL 32137

$699,500

5 beds

4 baths

2,600 sq ft

House

38 FRONT ST, PALM COAST, FL, 32137

Community: Grand Haven

New The Villages®

644 ELLSWORTH WAY, LADY LAKE, FL, 32162, Lady Lake, FL 32162

$250,000

2 beds

2 baths

1,148 sq ft

House

644 ELLSWORTH WAY, LADY LAKE, FL, 32162

Community: The Villages®

New The Villages®

2018 CASTANO PL, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$280,000

2 beds

2 baths

1,213 sq ft

House

2018 CASTANO PL, LADY LAKE, FL, 32159

Community: The Villages®

New

Cindy Certified

3008 RIBBON GRASS DR, MELBOURNE, FL, 329..., Melbourne, FL 32940

$550,000

2 baths

1,670 sq ft

House

6401 WHITE WILLOW CT, ST CLOUD, FL, 3477...

Community: Del Webb Sunbridge

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

Questions? Call us: (888) 625-4885

New Heritage Hills

3505 BELLAND CIR F, CLERMONT, FL, 34711, Clermont, FL 34711

$350,000

2 beds

2 baths

1,503 sq ft

Townhouse

3505 BELLAND CIR F, CLERMONT, FL, 34711

Community: Heritage Hills

New The Villages®

6088 KECKONEN DR, THE VILLAGES, FL, 3216..., The Villages, FL 32163

$749,900

3 beds

2 baths

1,960 sq ft

House

6088 KECKONEN DR, THE VILLAGES, FL, 3216...

Community: The Villages®

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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98 communities

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

98 communities near Winter Park

2,733 homes near Winter Park

2 beds

2 baths

1,574 sq ft

House

3 beds

2 baths

1,837 sq ft

Villa

2 beds

2 baths

1,434 sq ft

Villa

3 beds

2 baths

1,943 sq ft

House

3 beds

2 baths

1,209 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

3 baths

2,547 sq ft

House

5 beds

3 baths

3,193 sq ft

House

3 beds

3 baths

2,321 sq ft

House

2 beds

2 baths

1,188 sq ft

Villa

3 beds

2 baths

1,718 sq ft

House

4 beds

3 baths

2,246 sq ft

House

2 beds

3 baths

2,009 sq ft

House

2 beds

2 baths

1,308 sq ft

House

2 beds

2 baths

1,928 sq ft

House

3 beds

2 baths

2,058 sq ft

House

2 beds