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

3,537 homes near Winter Garden

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5 rating (1 reviews)

Del Webb Oasis

$400Ks - $900Ks

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 - $500Ks

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 - $600Ks

Solivita, Kissimmee, FL

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

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Questions? Call us: (689) 407-5757

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

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 - $500Ks

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 - $600Ks

Twin Lakes, St. Cloud, FL

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

Pelican Bay Daytona Beach

$100Ks - $400Ks

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, FL? 55places can help!

Questions? Call us: (689) 407-5757

4.7 rating (3 reviews)

Spruce Creek South

$100Ks - $400Ks

Spruce Creek South, Summerfield, FL

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

4.7 rating (11 reviews)

Valencia Lakes

$200Ks - $700Ks

Valencia Lakes, Wimauma, FL

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

3.8 rating (6 reviews)

Trilogy® Orlando

$200Ks - $600Ks

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

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

$300Ks - $1Ms

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, FL? 55places can help!

Questions? Call us: (689) 407-5757

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)

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

Breakaway Trails

$400Ks - $800Ks

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, FL? 55places can help!

Questions? Call us: (689) 407-5757

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

Pine Run Estates

$100Ks - $300Ks

Pine Run Estates, Ocala, FL

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

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

Esplanade at Wiregrass Ra...

$400Ks - $1Ms

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

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

4176 WIDMANN PL, THE VILLAGES, FL, 32163

Community: The Villages®

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

Questions? Call us: (689) 407-5757

Plantation at Leesburg

3529 MOUNT HOPE LOOP, LEESBURG, FL, 3474..., Leesburg, FL 34748

$329,900

2 beds

2 baths

1,723 sq ft

House

3529 MOUNT HOPE LOOP, LEESBURG, FL, 3474...

Community: Plantation at Leesburg

The Villages®

$739,000

3 beds

2 baths

2,060 sq ft

House

3353 WIELENGA PL, THE VILLAGES, FL, 3216...

Community: The Villages®

Sun City Center

$104,000

2 beds

2 baths

984 sq ft

Condo

2208 GRENADIER DR, SUN CITY CENTER, FL, ...

Community: Sun City Center

Spruce Creek Country Club

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

$350,000

2 beds

2 baths

1,995 sq ft

House

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

Community: Spruce Creek Country Club

Spruce Creek Country Club

9450 SE 130TH PLACE RD, SUMMERFIELD, FL,..., Summerfield, FL 34491

$399,000

3 beds

3 baths

2,252 sq ft

House

9450 SE 130TH PLACE RD, SUMMERFIELD, FL,...

Community: Spruce Creek Country Club

The Villages®

$220,000

2 beds

2 baths

1,196 sq ft

Manufactured Home

928 OLEANDER ST, THE VILLAGES, FL, 32159

Community: The Villages®

The Villages®

$299,900

2 beds

2 baths

1,156 sq ft

Villa

1999 KELMSCOTT ST, THE VILLAGES, FL, 321...

Community: The Villages®

The Villages®

$305,000

2 beds

2 baths

1,142 sq ft

House

3277 ASHBROOK PL, THE VILLAGES, FL, 3216...

Community: The Villages®

Sullivan Ranch

30532 GIDRAN TER, MOUNT DORA, FL, 32757, Mount Dora, FL 32757

$499,000

4 beds

2 baths

2,426 sq ft

House

30532 GIDRAN TER, MOUNT DORA, FL, 32757

Community: Sullivan Ranch

Latitude Margaritaville

298 HANG LOOSE WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124

$629,900

2 beds

3 baths

2,158 sq ft

House

298 HANG LOOSE WAY, DAYTONA BEACH, FL, 3...

Community: Latitude Margaritaville

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

Questions? Call us: (689) 407-5757

The Villages®

$289,900

2 beds

2 baths

1,090 sq ft

House

892 NASH LOOP, THE VILLAGES, FL, 32162

Community: The Villages®

Royal Harbor

5486 BOUNTY CIR, TAVARES, FL, 32778, Tavares, FL 32778

$409,000

3 beds

3 baths

2,284 sq ft

House

5486 BOUNTY CIR, TAVARES, FL, 32778

Community: Royal Harbor

The Villages®

$530,000

3 beds

3 baths

2,056 sq ft

House

3233 LOWE CT, THE VILLAGES, FL, 32163

Community: The Villages®

Marion Landing

8668 SW 67TH CT, OCALA, FL, 34476, Ocala, FL 34476

$190,000

3 beds

2 baths

1,296 sq ft

Manufactured Home

8668 SW 67TH CT, OCALA, FL, 34476

Community: Marion Landing

The Villages®

925 BEECHWOOD AVE, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$225,000

2 beds

2 baths

1,568 sq ft

Manufactured Home

925 BEECHWOOD AVE, LADY LAKE, FL, 32159

Community: The Villages®

On Top of the World

9722 SW 95TH CT C, OCALA, FL, 34481, Ocala, FL 34481

$174,900

2 beds

2 baths

1,412 sq ft

Villa

9722 SW 95TH CT C, OCALA, FL, 34481

Community: On Top of the World

Plantation at Leesburg

3603 WESTOVER CIR, LEESBURG, FL, 34748, Leesburg, FL 34748

$415,000

2 beds

2 baths

2,399 sq ft

House

3603 WESTOVER CIR, LEESBURG, FL, 34748

Community: Plantation at Leesburg

Sun City Center

$470,000

3 beds

2 baths

2,482 sq ft

Condo

1360 EMERALD DUNES DR, SUN CITY CENTER, ...

Community: Sun City Center

Ocala Palms

2291 NW 59TH TER, OCALA, FL, 34482, Ocala, FL 34482

$324,500

2 beds

2 baths

1,672 sq ft

House

2291 NW 59TH TER, OCALA, FL, 34482

Community: Ocala Palms

Sun City Center

$230,000

2 beds

2 baths

1,757 sq ft

Condo

920 VILLEROY GREENS DR, SUN CITY CENTER,...

House

5968 SW 103RD LOOP, OCALA, FL, 34476

Community: Cherrywood

Thunderbird Hill

$220,000

2 beds

2 baths

1,306 sq ft

Villa

3702 THUNDERBIRD HILL CIR, SEBRING, FL, ...

Community: Thunderbird Hill

The Villages®

12328 NE 48TH LOOP, OXFORD, FL, 34484, Oxford, FL 34484

$280,000

3 beds

2 baths

1,495 sq ft

House

12328 NE 48TH LOOP, OXFORD, FL, 34484

Community: The Villages®

On Top of the World

8862 SW 92ND ST D, OCALA, FL, 34481, Ocala, FL 34481

$173,000

2 beds

2 baths

1,530 sq ft

Condo

8862 SW 92ND ST D, OCALA, FL, 34481

Community: On Top of the World

On Top of the World

8677 SW 95TH LN A, OCALA, FL, 34481, Ocala, FL 34481

$169,900

2 beds

2 baths

1,530 sq ft

Villa

8677 SW 95TH LN A, OCALA, FL, 34481

Community: On Top of the World

The Villages®

$349,900

3 beds

2 baths

1,397 sq ft

House

594 LACY PL, THE VILLAGES, FL, 32162

Community: The Villages®

Sullivan Ranch

20945 OLDENBURG LOOP, MOUNT DORA, FL, 32..., Mount Dora, FL 32757

$399,000

3 beds

2 baths

2,164 sq ft

House

20945 OLDENBURG LOOP, MOUNT DORA, FL, 32...

Community: Sullivan Ranch

Harbor Hills Country Club

5072 GREENS DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$695,000

3 beds

3 baths

2,712 sq ft

House

5072 GREENS DR, LADY LAKE, FL, 32159

Villa

3538 BELLAND CIR B, CLERMONT, FL, 34711

Community: Heritage Hills

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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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3,537 homes near Winter Garden

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

109 communities near Winter Garden

3,537 homes near Winter Garden

3 beds

2 baths

1,820 sq ft

House

2 beds

2 baths

1,292 sq ft

Manufactured Home

2 beds

2 baths

1,451 sq ft

House

3 beds

2 baths

1,419 sq ft

House

3 beds

2 baths

1,959 sq ft

House

2 beds

2 baths

1,723 sq ft

House

3 beds

2 baths

2,060 sq ft

House

2 beds

2 baths

984 sq ft

Condo

2 beds

2 baths

1,995 sq ft

House

3 beds

3 baths

2,252 sq ft

House

2 beds

2 baths

1,196 sq ft

Manufactured Home

2 beds

2 baths

1,156 sq ft

Villa

2 beds

2 baths

1,142 sq ft

House

4 beds

2 baths

2,426 sq ft

House

2 beds

3 baths

2,158 sq ft

House

2 beds

2 baths

1,090 sq ft

House

3 beds

3 baths

2,284 sq ft

House

3 beds

3 baths

2,056 sq ft

House

3 beds

2 baths

1,296 sq ft

Manufactured Home

2 beds