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

3,703 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 - $1Ms

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 - $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 (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 - $700Ks

Stone Creek, Ocala, FL

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

4.1 rating (29 reviews)

Oak Run

$100Ks - $300Ks

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

<$100k - $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

$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

No reviews yet

Venetian Bay

$300Ks - $2Ms

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 - $500Ks

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

$400Ks - $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? 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 - $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 - $500Ks

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 - $500Ks

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

$400Ks - $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

4.4 rating (16 reviews)

Del Webb Orlando

$300Ks - $400Ks

Del Webb Orlando, Davenport, FL

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

No reviews yet

Pine Run Estates

<$100k - $300Ks

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

8890 SW 104TH CIR, OCALA, FL, 34481

House

1201 BLUEWATER DR, SUN CITY CENTER, FL, ...

885 CORAL REEF WAY, DAYTONA BEACH, FL, 3...

Community: Latitude Margaritaville

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

Questions? Call us: (689) 407-5757

Latitude Margaritaville

227 CORAL REEF WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124

$499,900

2 beds

2 baths

1,786 sq ft

House

227 CORAL REEF WAY, DAYTONA BEACH, FL, 3...

Community: Latitude Margaritaville

Oak Run

10821 SW 87TH TER, OCALA, FL, 34481, Ocala, FL 34481

$248,900

2 beds

2 baths

1,392 sq ft

House

10821 SW 87TH TER, OCALA, FL, 34481

Community: Oak Run

Pennbrooke Fairways

33236 GRAND CYPRESS WAY, LEESBURG, FL, 3..., Leesburg, FL 34748

$299,247

3 beds

2 baths

1,598 sq ft

House

33236 GRAND CYPRESS WAY, LEESBURG, FL, 3...

Community: Pennbrooke Fairways

Pennbrooke Fairways

910 EAGLES LNDG, LEESBURG, FL, 34748, Leesburg, FL 34748

$299,247

3 beds

2 baths

1,807 sq ft

House

910 EAGLES LNDG, LEESBURG, FL, 34748

Community: Pennbrooke Fairways

Ocala Palms

5915 NW 18TH PL, OCALA, FL, 34482, Ocala, FL 34482

$304,900

2 beds

2 baths

1,650 sq ft

House

5915 NW 18TH PL, OCALA, FL, 34482

Community: Ocala Palms

The Villages®

$374,247

3 beds

2 baths

1,392 sq ft

House

421 ALDAMA AVE, THE VILLAGES, FL, 32159

Community: The Villages®

Ocala Palms

5500 NW 23RD PL, OCALA, FL, 34482, Ocala, FL 34482

$265,000

3 beds

2 baths

1,837 sq ft

House

5500 NW 23RD PL, OCALA, FL, 34482

Community: Ocala Palms

Sun City Center

$339,999

2 beds

2 baths

1,528 sq ft

House

301 CALOOSA PALMS CT, SUN CITY CENTER, F...

Community: Sun City Center

Del Webb Sunbridge

6375 TRAILBLAZE BND, SAINT CLOUD, FL, 34..., Saint Cloud, FL 34771

$745,000

4 beds

4 baths

2,781 sq ft

House

6375 TRAILBLAZE BND, SAINT CLOUD, FL, 34...

Community: Del Webb Sunbridge

Del Webb Sunbridge

2793 NATURE VIEW RD, SAINT CLOUD, FL, 34..., Saint Cloud, FL 34771

$679,000

4 beds

3 baths

2,761 sq ft

House

2793 NATURE VIEW RD, SAINT CLOUD, FL, 34...

Community: Del Webb Sunbridge

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

Questions? Call us: (689) 407-5757

Valencia del Sol

4836 SEVILLA SHORES DR, WIMAUMA, FL, 335..., Wimauma, FL 33598

$485,000

3 beds

2 baths

1,890 sq ft

House

4836 SEVILLA SHORES DR, WIMAUMA, FL, 335...

Community: Valencia del Sol

Highland Fairways

2234 SEA ISLAND CIR, LAKELAND, FL, 33810, Lakeland, FL 33810

$215,000

2 beds

2 baths

1,166 sq ft

House

2234 SEA ISLAND CIR, LAKELAND, FL, 33810

Community: Highland Fairways

Esplanade at Wiregrass Ranch

4831 ROSATTI RD, WESLEY CHAPEL, FL, 3354..., Wesley Chapel, FL 33543

$675,000

3 beds

3 baths

2,296 sq ft

House

4831 ROSATTI RD, WESLEY CHAPEL, FL, 3354...

Community: Esplanade at Wiregrass Ranch

Pennbrooke Fairways

32622 OAK PARK DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$234,247

3 beds

2 baths

1,611 sq ft

House

32622 OAK PARK DR, LEESBURG, FL, 34748

Community: Pennbrooke Fairways

Marion Landing

8554 SW 63RD CT, OCALA, FL, 34476, Ocala, FL 34476

$249,900

3 beds

2 baths

1,829 sq ft

House

8554 SW 63RD CT, OCALA, FL, 34476

Community: Marion Landing

Cherrywood

10141 SW 62ND TERRACE RD, OCALA, FL, 344..., Ocala, FL 34476

$179,900

2 beds

2 baths

1,396 sq ft

House

10141 SW 62ND TERRACE RD, OCALA, FL, 344...

Community: Cherrywood

Royal Harbor

5502 BOUNTY CIR, TAVARES, FL, 32778, Tavares, FL 32778

$356,400

3 beds

2 baths

1,901 sq ft

House

5502 BOUNTY CIR, TAVARES, FL, 32778

Community: Royal Harbor

VillageWalk at Lake Nona

8430 LEATHERLEAF LN, ORLANDO, FL, 32827, Orlando, FL 32827

$415,000

3 beds

3 baths

1,810 sq ft

Townhouse

8430 LEATHERLEAF LN, ORLANDO, FL, 32827

Community: VillageWalk at Lake Nona

Stone Creek

9685 SW 63RD LOOP, OCALA, FL, 34481, Ocala, FL 34481

$249,500

2 beds

2 baths

1,305 sq ft

House

9685 SW 63RD LOOP, OCALA, FL, 34481

Community: Stone Creek

Solivita

2448 PALM TREE DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$314,900

3 beds

2 baths

1,539 sq ft

Villa

2448 PALM TREE DR, KISSIMMEE, FL, 34759

Manufactured Home

8333 COUNTY ROAD 109A-1, LADY LAKE, FL, ...

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.

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

Call us: (689) 407-5757

3,703 homes near Winter Garden

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

108 communities near Winter Garden

3,703 homes near Winter Garden

3 beds

2 baths

1,859 sq ft

House

3 beds

2 baths

2,063 sq ft

House

3 beds

3 baths

2,006 sq ft

House

3 beds

2 baths

1,874 sq ft

House

3 beds

2 baths

1,651 sq ft

House

3 beds

2 baths

1,709 sq ft

House

2 beds

2 baths

1,175 sq ft

Villa

3 beds

2 baths

2,190 sq ft

House

2 beds

2 baths

1,756 sq ft

House

2 beds

2 baths

1,558 sq ft

House

3 beds

2 baths

1,521 sq ft

House

3 beds

2 baths

1,469 sq ft

House

2 beds

2 baths

1,767 sq ft

House

2 beds

2 baths

2,019 sq ft

House

2 beds

2 baths

1,558 sq ft

House

2 beds

2 baths

1,786 sq ft

House

2 beds

2 baths

1,392 sq ft

House

3 beds

2 baths

1,598 sq ft

House

3 beds

2 baths

1,807 sq ft

House

2 beds