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

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

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

714 DEL ROSARIO ST, THE VILLAGES, FL, 32...

Community: The Villages®

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

Questions? Call us: (689) 407-5757

Pelican Bay Daytona Beach

42 CORMORANT CIR, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32119

$409,900

4 beds

2 baths

1,862 sq ft

House

42 CORMORANT CIR, DAYTONA BEACH, FL, 321...

Community: Pelican Bay Daytona Beach

The Villages®

$809,900

3 beds

2 baths

2,082 sq ft

House

917 RAMOS DR, THE VILLAGES, FL, 32159

Community: The Villages®

Pelican Bay Daytona Beach

236 GULL DR, DAYTONA BEACH, FL, 32119, Daytona Beach, FL 32119

$315,000

2 beds

2 baths

2,100 sq ft

House

236 GULL DR, DAYTONA BEACH, FL, 32119

Community: Pelican Bay Daytona Beach

Lakes at Laurel Highlands

2162 BLUE HIGHLANDS DR, LAKELAND, FL, 33..., Lakeland, FL 33811

$314,900

3 beds

2 baths

1,784 sq ft

House

2162 BLUE HIGHLANDS DR, LAKELAND, FL, 33...

Community: Lakes at Laurel Highlands

New Royal Harbor

5740 BOUNTY CIR, TAVARES, FL, 32778, Tavares, FL 32778

$460,000

4 beds

3 baths

3,136 sq ft

House

5740 BOUNTY CIR, TAVARES, FL, 32778

Community: Royal Harbor

Huntington at Hunter's Ridge

99 HUNTINGTON PL, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174

$499,700

3 beds

2 baths

2,238 sq ft

House

99 HUNTINGTON PL, ORMOND BEACH, FL, 3217...

Community: Huntington at Hunter's Ridge

Plantation at Leesburg

5413 BARNWELL CT, LEESBURG, FL, 34748, Leesburg, FL 34748

$399,000

2 beds

2 baths

2,383 sq ft

House

5413 BARNWELL CT, LEESBURG, FL, 34748

Community: Plantation at Leesburg

The Villages®

116 CYPRESS RD, WILDWOOD, FL, 34785, Wildwood, FL 34785

$55,000

2 beds

2 baths

1,040 sq ft

Manufactured Home

116 CYPRESS RD, WILDWOOD, FL, 34785

Community: The Villages®

Plantation at Leesburg

25034 BETTON HL, LEESBURG, FL, 34748, Leesburg, FL 34748

$139,000

3 beds

2 baths

1,456 sq ft

Manufactured Home

25034 BETTON HL, LEESBURG, FL, 34748

Community: Plantation at Leesburg

New Lake James

7838 LAKE JAMES BLVD, LAKELAND, FL, 3381..., Lakeland, FL 33810

$500,000

3 beds

3 baths

2,362 sq ft

House

7838 LAKE JAMES BLVD, LAKELAND, FL, 3381...

Community: Lake James

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

Questions? Call us: (689) 407-5757

The Villages®

$359,900

3 beds

2 baths

1,406 sq ft

Villa

1537 BARNWELL PL, THE VILLAGES, FL, 3216...

Community: The Villages®

The Villages®

$339,900

3 beds

2 baths

1,496 sq ft

House

17718 SE 81ST WYNSTONE AVE, THE VILLAGES...

Community: The Villages®

Sun City Center

$274,000

2 beds

2 baths

1,396 sq ft

Condo

2427 SIFIELD GREENS WAY, SUN CITY CENTER...

Community: Sun City Center

New Venetian Bay

3417 GALLIA ST, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168

$429,000

4 beds

4 baths

2,402 sq ft

Townhouse

3417 GALLIA ST, NEW SMYRNA BEACH, FL, 32...

Community: Venetian Bay

New Twin Lakes

5114 TWIN LAKES BLVD, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34772

$549,370

2 beds

2 baths

1,917 sq ft

House

5114 TWIN LAKES BLVD, SAINT CLOUD, FL, 3...

Community: Twin Lakes

New Esplanade at Wiregrass Ranch

4545 ISONZO WAY, WESLEY CHAPEL, FL, 3354..., Wesley Chapel, FL 33543

$850,000

3 beds

3 baths

2,438 sq ft

House

4545 ISONZO WAY, WESLEY CHAPEL, FL, 3354...

Community: Esplanade at Wiregrass Ranch

New Sun City Center

704 BRANNEN CIR, SUN CITY CENTER, FL, 33..., Sun City Center, FL 33573

$250,000

2 beds

2 baths

1,205 sq ft

House

704 BRANNEN CIR, SUN CITY CENTER, FL, 33...

Community: Sun City Center

New The Villages®

1613 BAY MEADOWS LN, LADY LAKE, FL, 3215..., Lady Lake, FL 32159

$225,000

2 beds

2 baths

1,384 sq ft

Manufactured Home

1613 BAY MEADOWS LN, LADY LAKE, FL, 3215...

Community: The Villages®

New Twin Lakes

2758 MIDSWEET AVE, SAINT CLOUD, FL, 3477..., Saint Cloud, FL 34772

$474,810

2 beds

2 baths

1,981 sq ft

House

2758 MIDSWEET AVE, SAINT CLOUD, FL, 3477...

Community: Twin Lakes

New Oak Run

8534 SW 108TH PLACE RD, OCALA, FL, 34481, Ocala, FL 34481

$179,900

2 beds

2 baths

1,160 sq ft

House

8534 SW 108TH PLACE RD, OCALA, FL, 34481

House

9921 SW 103RD PL, OCALA, FL, 34481

House

17145 SE 93RD YONDEL CIR, THE VILLAGES, ...

Community: The Villages®

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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?

Call us: (689) 407-5757

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

2 beds

2 baths

1,983 sq ft

House

2 beds

2 baths

1,409 sq ft

Villa

2 beds

2 baths

1,156 sq ft

Villa

3 beds

2 baths

1,292 sq ft

Manufactured Home

3 beds

2 baths

1,908 sq ft

House

4 beds

2 baths

1,862 sq ft

House

3 beds

2 baths

2,082 sq ft

House

2 beds

2 baths

2,100 sq ft

House

3 beds

2 baths

1,784 sq ft

House

4 beds

3 baths

3,136 sq ft

House

3 beds

2 baths

2,238 sq ft

House

2 beds

2 baths

2,383 sq ft

House

2 beds

2 baths

1,040 sq ft

Manufactured Home

3 beds

2 baths

1,456 sq ft

Manufactured Home

3 beds

3 baths

2,362 sq ft

House

3 beds

2 baths

1,406 sq ft

Villa

3 beds

2 baths

1,496 sq ft

House

2 beds

2 baths

1,396 sq ft

Condo

4 beds

4 baths

2,402 sq ft

Townhouse

2 beds