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

3,573 homes near Winter Garden

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Del Webb Oasis

$400Ks - $1Ms

Del Webb Oasis, Winter Garden, FL

New Construction | 55+ age-restricted | Built 2020 - present | 422 homes

4 rating (17 reviews)

The Villages®

<$100k - $2Ms

The Villages®, The Villages, FL

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

4.1 rating (55 reviews)

On Top of the World

$100Ks - $600Ks

On Top of the World, Ocala, FL

New and Resale | 55+ age-restricted | Built 1981 - present | 10,000 homes

3.8 rating (14 reviews)

Sun City Center

<$100k - $600Ks

Sun City Center, Sun City Center, FL

Resale Only | 55+ age-restricted | Built 1961 - 2018 | 9,500 homes

4.7 rating (18 reviews)

Solivita

$100Ks - $700Ks

Solivita, Kissimmee, FL

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

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

Questions? Call us: (689) 407-5757

3.6 rating (46 reviews)

Latitude Margaritaville

$300Ks - $700Ks

Latitude Margaritaville, Daytona Beach, FL

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

4.2 rating (10 reviews)

Stone Creek

$200Ks - $800Ks

Stone Creek, Ocala, FL

New and Resale | 55+ age-restricted | Built 2006 - present | 3,800 homes

4.1 rating (29 reviews)

Oak Run

$100Ks - $500Ks

Oak Run, Ocala, FL

Resale Only | 55+ age-restricted | Built 1985 - 2007 | 3,509 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

5 rating (2 reviews)

Plantation at Leesburg

$100Ks - $400Ks

Plantation at Leesburg, Leesburg, FL

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

Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.

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 - $900Ks

Twin Lakes, St. Cloud, FL

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

No reviews yet

Pelican Bay Daytona Beach

$100Ks - $500Ks

Pelican Bay Daytona Beach, Daytona Beach, FL

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

4.6 rating (5 reviews)

Ocala Preserve

$200Ks - $600Ks

Ocala Preserve, Ocala, FL

New and Resale | 55+ age-restricted | Built 2014 - present | 1,800 homes

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

Questions? Call us: (689) 407-5757

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

4.7 rating (11 reviews)

Valencia Lakes

$200Ks - $900Ks

Valencia Lakes, Wimauma, FL

Resale Only | 55+ age-restricted | Built 2005 - 2019 | 1,631 homes

5 rating (1 reviews)

Cypress Lakes

$200Ks - $200Ks

Cypress Lakes, Lakeland, FL

Resale Only | 55+ age-restricted | Built 1987 - 2016 | 1,604 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

No reviews yet

Venetian Bay

$200Ks - $1Ms

Venetian Bay, New Smyrna Beach, FL

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

3.8 rating (6 reviews)

Trilogy® Orlando

$300Ks - $600Ks

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

3.8 rating (6 reviews)

Tampa Bay Golf and Countr...

$200Ks - $400Ks

Tampa Bay Golf and Countr..., San Antonio, FL

Resale Only | 55+ age-restricted | Built 1994 - 2015 | 1,336 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

$400Ks - $900Ks

VillageWalk at Lake Nona, Orlando, FL

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

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

Questions? Call us: (689) 407-5757

5 rating (8 reviews)

Pennbrooke Fairways

$100Ks - $300Ks

Pennbrooke Fairways, Leesburg, FL

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

5 rating (1 reviews)

Sandpiper Golf & Coun...

$200Ks - $300Ks

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)

Ocala Palms

$100Ks - $400Ks

Ocala Palms, Ocala, FL

Resale Only | 55+ age-restricted | Built 1994 - 1997 | 1,076 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

5 rating (5 reviews)

SummerGlen

$200Ks - $400Ks

SummerGlen, Ocala, FL

Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,024 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

No reviews yet

Breakaway Trails

$300Ks - $1Ms

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

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

Questions? Call us: (689) 407-5757

4.8 rating (6 reviews)

Highland Lakes

$200Ks - $300Ks

Highland Lakes, Leesburg, FL

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

4.3 rating (15 reviews)

Del Webb Orlando

$200Ks - $400Ks

Del Webb Orlando, Davenport, FL

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

No reviews yet

Pine Run Estates

<$100k - $400Ks

Pine Run Estates, Ocala, FL

Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 homes

No reviews yet

Lake Jovita Golf and Coun...

$300Ks - $1Ms

Lake Jovita Golf and Coun..., Dade City, FL

New and Resale | Age-targeted | Built 1999 - present | 875 homes

No reviews yet

Esplanade at Wiregrass Ra...

$400Ks - $1Ms

Esplanade at Wiregrass Ra..., Wesley Chapel, FL

New and Resale | 55+ age-restricted | Built 2019 - present | 868 homes

4906 AVILA LAKES DR, WIMAUMA, FL, 33598

House

20505 QUEEN ALEXANDRA DR, LEESBURG, FL, ...

Community: Royal Highlands

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

Questions? Call us: (689) 407-5757

Stone Creek

6776 SW 95TH CIR, OCALA, FL, 34481, Ocala, FL 34481

$499,499

2 beds

2 baths

2,031 sq ft

House

6776 SW 95TH CIR, OCALA, FL, 34481

Community: Stone Creek

Pennbrooke Fairways

305 RANCHWOOD DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$249,247

2 beds

2 baths

1,631 sq ft

House

305 RANCHWOOD DR, LEESBURG, FL, 34748

Community: Pennbrooke Fairways

The Villages®

$389,000

3 beds

2 baths

1,770 sq ft

House

867 CORTEZ AVE, THE VILLAGES, FL, 32159

Community: The Villages®

Sun City Center

$417,000

2 beds

2 baths

1,490 sq ft

House

1103 VILLEROY DR, SUN CITY CENTER, FL, 3...

Community: Sun City Center

Stonecrest

12205 SE 173RD PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$279,000

3 beds

2 baths

1,475 sq ft

House

12205 SE 173RD PL, SUMMERFIELD, FL, 3449...

Community: Stonecrest

Venetian Bay

349 CARYOTA CT, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168

$399,000

3 beds

2 baths

1,520 sq ft

House

349 CARYOTA CT, NEW SMYRNA BEACH, FL, 32...

Community: Venetian Bay

The Villages®

$280,000

2 beds

2 baths

1,094 sq ft

Villa

728 RAMIREZ AVE, THE VILLAGES, FL, 32159

Community: The Villages®

The Villages®

5092 NE 81ST BLVD, WILDWOOD, FL, 34785, Wildwood, FL 34785

$1,200,000

3 beds

3 baths

3,407 sq ft

House

5092 NE 81ST BLVD, WILDWOOD, FL, 34785

Community: The Villages®

Stonecrest

17563 SE 122ND TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491

$559,900

3 beds

3 baths

2,071 sq ft

House

17563 SE 122ND TER, SUMMERFIELD, FL, 344...

Community: Stonecrest

Summit Greens

2298 CALEDONIAN ST, CLERMONT, FL, 34711, Clermont, FL 34711

$379,000

3 beds

2 baths

1,784 sq ft

House

2298 CALEDONIAN ST, CLERMONT, FL, 34711

Community: Summit Greens

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

Questions? Call us: (689) 407-5757

Plantation at Leesburg

25243 RIVER CREST DR, LEESBURG, FL, 3474..., Leesburg, FL 34748

$369,900

3 beds

3 baths

2,529 sq ft

House

25243 RIVER CREST DR, LEESBURG, FL, 3474...

Community: Plantation at Leesburg

Sun City Center

$154,998

2 beds

2 baths

984 sq ft

Condo

216 GLOUCESTER BLVD # 216, SUN CITY CENT...

Community: Sun City Center

The Villages®

$359,500

3 beds

2 baths

1,572 sq ft

House

1425 HOLLYBERRY PL, THE VILLAGES, FL, 32...

3998 BEDFORD AVE, WINTER HAVEN, FL, 3388...

432 GRAND CANAL DR, POINCIANA, FL, 34759

Community: Solivita

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

Questions? Call us: (689) 407-5757

Cresswind at Victoria Gardens

1612 LINCOLNSHIRE DR, DELAND, FL, 32724, Deland, FL 32724

$420,000

3 beds

2 baths

1,905 sq ft

House

1612 LINCOLNSHIRE DR, DELAND, FL, 32724

Community: Cresswind at Victoria Gardens

Del Webb Orlando

588 CANTABRIA DR, DAVENPORT, FL, 33837, Davenport, FL 33837

$450,000

2 beds

2 baths

1,702 sq ft

House

588 CANTABRIA DR, DAVENPORT, FL, 33837

Community: Del Webb Orlando

Sun City Center

$219,900

2 beds

2 baths

1,579 sq ft

Condo

2410 LANCASTER DR NA, SUN CITY CENTER, F...

Community: Sun City Center

Del Webb Sunbridge

2948 SCOUT ST, SAINT CLOUD, FL, 34771, Saint Cloud, FL 34771

$949,000

5 beds

5 baths

3,517 sq ft

House

2948 SCOUT ST, SAINT CLOUD, FL, 34771

Community: Del Webb Sunbridge

Highland Lakes

26062 NEWCOMBE CIR, LEESBURG, FL, 34748, Leesburg, FL 34748

$210,000

2 beds

2 baths

1,120 sq ft

Villa

26062 NEWCOMBE CIR, LEESBURG, FL, 34748

Community: Highland Lakes

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Frequently Asked Questions

What size 55+ communities are there in Winter Garden?

In Winter Garden, there are no large communities, no medium communities, and 2 small communities with less than 500 homes.

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

The smallest 55+ communities in Winter Garden has 163 homes, the largest has 422 homes, and the average communities consists of 292 homes.

Are there new 55+ homes available in Winter Garden?

Yes, there are new 55+ homes available in Winter Garden. The most recent communities started in Winter Garden include Overture Hamlin, Del Webb Oasis. There are also 2 communities in Winter Garden that offer new construction homes, including Overture Hamlin, Del Webb Oasis.

Are there gated 55+ communities in Winter Garden?

Yes, there is gated 55+ communities in Winter Garden. Approximately 50.0% of 55+ communities in the area are gated. For instance, Del Webb Oasis is a gated communities with 422 homes.

Want more information about active adult communities around Winter Garden?

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Want to learn more about 55+ communities in Winter Garden?

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3,573 homes near Winter Garden

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

106 communities near Winter Garden

3,573 homes near Winter Garden

3 beds

2 baths

1,610 sq ft

House

3 beds

2 baths

2,058 sq ft

House

3 beds

2 baths

2,028 sq ft

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2 beds

2 baths

1,861 sq ft

House

2 beds

2 baths

1,646 sq ft

Villa

2 beds

2 baths

1,656 sq ft

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2 beds

2 baths

1,622 sq ft

House

3 beds

4 baths

2,625 sq ft

House

3 beds

2 baths

2,000 sq ft

House

3 beds

2 baths

1,728 sq ft

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3 beds

2 baths

1,607 sq ft

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3 beds

2 baths

1,528 sq ft

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2 beds

2 baths

1,798 sq ft

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2 beds

2 baths

1,681 sq ft

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3 beds

2 baths

1,396 sq ft

House

2 beds

2 baths

2,031 sq ft

House

2 beds

2 baths

1,631 sq ft

House

3 beds

2 baths

1,770 sq ft

House

2 beds

2 baths

1,490 sq ft

House

3 beds