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

3,958 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 - $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

<$100k - $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

$200Ks - $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 - $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 - $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 - $600Ks

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 - $1Ms

Twin Lakes, St. Cloud, FL

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

No reviews yet

Pelican Bay Daytona Beach

<$100k - $600Ks

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

$200Ks - $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 - $900Ks

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

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)

Trilogy® Orlando

$200Ks - $600Ks

Trilogy® Orlando, Groveland, FL

Resale Only | 55+ age-restricted | Built 2005 - 2022 | 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

$100Ks - $300Ks

Pennbrooke Fairways, Leesburg, FL

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

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

3.6 rating (5 reviews)

Heritage Hills

$300Ks - $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 - $500Ks

SummerGlen, Ocala, FL

Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,029 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 - $700Ks

Breakaway Trails, Ormond Beach, FL

New and Resale | Age-targeted | Built 1985 - present | 976 homes

4 rating (4 reviews)

Lakes of Mount Dora

$200Ks - $800Ks

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 - $800Ks

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

$100Ks - $300Ks

Highland Lakes, Leesburg, FL

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

4.3 rating (15 reviews)

Del Webb Orlando

$200Ks - $500Ks

Del Webb Orlando, Davenport, FL

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

No reviews yet

Pine Run Estates

$100Ks - $400Ks

Pine Run Estates, Ocala, FL

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

No reviews yet

Lake Jovita Golf and Coun...

$400Ks - $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 - $900Ks

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

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

2476 PINE PRESERVE CT, SAINT CLOUD, FL, ...

Community: Del Webb Sunbridge

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

Questions? Call us: (689) 407-5757

On Top of the World

9260 SW 92ND PLACE RD, OCALA, FL, 34481, Ocala, FL 34481

$229,500

3 beds

2 baths

2,246 sq ft

House

9260 SW 92ND PLACE RD, OCALA, FL, 34481

Community: On Top of the World

Trilogy® Orlando

107 CUPANIA CT, GROVELAND, FL, 34736, Groveland, FL 34736

$359,000

2 beds

2 baths

1,612 sq ft

House

107 CUPANIA CT, GROVELAND, FL, 34736

Community: Trilogy® Orlando

Spruce Creek North

10980 SW 63RD AVE, OCALA, FL, 34476, Ocala, FL 34476

$249,500

3 beds

3 baths

1,966 sq ft

House

10980 SW 63RD AVE, OCALA, FL, 34476

Community: Spruce Creek North

Sun City Center

$270,000

2 beds

2 baths

1,188 sq ft

Condo

1257 LYNDHURST GREENS DR, SUN CITY CENTE...

Community: Sun City Center

Arlington Ridge

$349,900

2 beds

2 baths

1,704 sq ft

House

4347 ARLINGTON RIDGE BLVD, LEESBURG, FL,...

Community: Arlington Ridge

Lake Henry Estates

465 SWEETWATER WAY, HAINES CITY, FL, 338..., Haines City, FL 33844

$279,000

2 beds

2 baths

1,722 sq ft

House

465 SWEETWATER WAY, HAINES CITY, FL, 338...

Community: Lake Henry Estates

Ocala Palms

5065 NW 21ST LOOP, OCALA, FL, 34482, Ocala, FL 34482

$229,500

2 beds

2 baths

1,388 sq ft

House

5065 NW 21ST LOOP, OCALA, FL, 34482

Community: Ocala Palms

Oak Run

10954 SW 83RD CT, OCALA, FL, 34481, Ocala, FL 34481

$191,000

2 beds

2 baths

1,224 sq ft

House

10954 SW 83RD CT, OCALA, FL, 34481

Community: Oak Run

Sun City Center

$265,000

2 beds

2 baths

1,825 sq ft

Condo

902 MCDANIEL ST # 1, SUN CITY CENTER, FL...

Community: Sun City Center

Tampa Bay Golf and Country Club

10809 COLLAR DR, SAN ANTONIO, FL, 33576, San Antonio, FL 33576

$319,900

3 beds

2 baths

1,778 sq ft

House

10809 COLLAR DR, SAN ANTONIO, FL, 33576

Community: Tampa Bay Golf and Country Club

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

Questions? Call us: (689) 407-5757

Twin Lakes

2717 GREENLANDS ST, SAINT CLOUD, FL, 347..., Saint Cloud, FL 34772

$523,000

3 beds

2 baths

1,863 sq ft

House

2717 GREENLANDS ST, SAINT CLOUD, FL, 347...

Community: Twin Lakes

Summer Trees

6068 SPRUCE POINT CIR, PORT ORANGE, FL, ..., Port Orange, FL 32128

$649,900

4 beds

3 baths

2,438 sq ft

House

6068 SPRUCE POINT CIR, PORT ORANGE, FL, ...

Community: Summer Trees

Southshore Bay

16810 SCUBA CREST ST, WIMAUMA, FL, 33598, Wimauma, FL 33598

$490,000

2 beds

3 baths

2,239 sq ft

House

16810 SCUBA CREST ST, WIMAUMA, FL, 33598

Community: Southshore Bay

Sun City Center

$409,900

2 beds

2 baths

1,854 sq ft

Condo

2253 OAKLEY GREEN DR # 26, SUN CITY CENT...

Community: Sun City Center

Oak Run

8111 SW 108TH STREET RD, OCALA, FL, 3448..., Ocala, FL 34481

$199,999

2 beds

2 baths

1,539 sq ft

House

8111 SW 108TH STREET RD, OCALA, FL, 3448...

Community: Oak Run

JB Ranch

6444 SW 88TH LOOP, OCALA, FL, 34476, Ocala, FL 34476

$365,000

3 beds

2 baths

1,811 sq ft

House

6444 SW 88TH LOOP, OCALA, FL, 34476

Community: JB Ranch

Lake Ashton

4076 TRALEE DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859

$304,900

2 beds

2 baths

1,445 sq ft

House

4076 TRALEE DR, LAKE WALES, FL, 33859

13729 SE 89TH AVE, SUMMERFIELD, FL, 3449...

Community: Spruce Creek Country Club

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

Questions? Call us: (689) 407-5757

Spruce Creek Country Club

13544 SE 89TH TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491

$449,500

3 beds

2 baths

2,278 sq ft

House

13544 SE 89TH TERRACE RD, SUMMERFIELD, F...

Community: Spruce Creek Country Club

Stonecrest

12163 SE 176TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491

$539,000

3 beds

2 baths

2,668 sq ft

House

12163 SE 176TH LOOP, SUMMERFIELD, FL, 34...

Community: Stonecrest

Spruce Creek South

17744 SE 95TH CT, SUMMERFIELD, FL, 34491, Summerfield, FL 34491

$309,900

3 beds

2 baths

1,450 sq ft

House

17744 SE 95TH CT, SUMMERFIELD, FL, 34491

Community: Spruce Creek South

The Country Club of Mount Dora

7023 ARCADIAN CT, MOUNT DORA, FL, 32757, Mount Dora, FL 32757

$485,000

3 beds

2 baths

1,745 sq ft

House

7023 ARCADIAN CT, MOUNT DORA, FL, 32757

Community: The Country Club of Mount Dora

Latitude Margaritaville

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

$629,900

3 beds

3 baths

2,110 sq ft

House

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

Community: Latitude Margaritaville

Del Webb Sunbridge

6439 TRAILBLAZE BND, SAINT CLOUD, FL, 34..., Saint Cloud, FL 34771

$915,000

5 beds

5 baths

3,517 sq ft

House

6439 TRAILBLAZE BND, SAINT CLOUD, FL, 34...

Community: Del Webb Sunbridge

Lake Ashton

4068 STONE CREEK LOOP, LAKE WALES, FL, 3..., Lake Wales, FL 33859

$550,000

3 beds

2 baths

2,064 sq ft

House

4068 STONE CREEK LOOP, LAKE WALES, FL, 3...

Community: Lake Ashton

Lake Ashton

5269 PEBBLE BEACH BLVD, WINTER HAVEN, FL..., Winter Haven, FL 33884

$292,500

2 beds

2 baths

1,495 sq ft

House

5269 PEBBLE BEACH BLVD, WINTER HAVEN, FL...

Community: Lake Ashton

Carillon Lakes

3379 FIDDLE LEAF WAY, LAKELAND, FL, 3381..., Lakeland, FL 33811

$337,775

3 beds

2 baths

1,624 sq ft

House

3379 FIDDLE LEAF WAY, LAKELAND, FL, 3381...

Community: Carillon Lakes

Lake Ashton

4101 LIMERICK DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859

$429,000

2 beds

2 baths

1,882 sq ft

House

4101 LIMERICK DR, LAKE WALES, FL, 33859

Villa

17322 HOLLY WELL AVE, WIMAUMA, FL, 33598

Community: Southshore Bay

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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.

How long do listings in 55+ communities in Winter Garden typically stay on the market, and what is the average price of homes for sale?

On average, listings in 55+ communities in Winter Garden stay on the market for around 143 days. The average price of homes for sale in these communities is approximately $502,460, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Del Webb Oasis average around $502,460.

Want more information about active adult communities around Winter Garden?

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3,958 homes near Winter Garden

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

106 communities near Winter Garden

3,958 homes near Winter Garden

2 beds

2 baths

2,194 sq ft

House

3 beds

2 baths

1,918 sq ft

House

3 beds

2 baths

1,857 sq ft

House

2 beds

2 baths

1,656 sq ft

House

4 beds

3 baths

2,249 sq ft

House

3 beds

2 baths

2,246 sq ft

House

2 beds

2 baths

1,612 sq ft

House

3 beds

3 baths

1,966 sq ft

House

2 beds

2 baths

1,188 sq ft

Condo

2 beds

2 baths

1,704 sq ft

House

2 beds

2 baths

1,722 sq ft

House

2 beds

2 baths

1,388 sq ft

House

2 beds

2 baths

1,224 sq ft

House

2 beds

2 baths

1,825 sq ft

Condo

3 beds

2 baths

1,778 sq ft

House

3 beds

2 baths

1,863 sq ft

House

4 beds

3 baths

2,438 sq ft

House

2 beds

3 baths

2,239 sq ft

House

2 beds

2 baths

1,854 sq ft

Condo

2 beds