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

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 - $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)

VillageWalk at Lake Nona

$400Ks - $1Ms

VillageWalk at Lake Nona, Orlando, FL

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

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

4941 NW 32ND ST, OCALA, FL, 34482

Community: Quail Meadow

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

Questions? Call us: (689) 407-5757

On Top of the World

8665 SW 94TH LN C, OCALA, FL, 34481, Ocala, FL 34481

$237,500

2 beds

2 baths

1,541 sq ft

Villa

8665 SW 94TH LN C, OCALA, FL, 34481

Community: On Top of the World

On Top of the World

8685 SW 94TH LN B, OCALA, FL, 34481, Ocala, FL 34481

$187,500

2 beds

2 baths

1,571 sq ft

Villa

8685 SW 94TH LN B, OCALA, FL, 34481

Community: On Top of the World

Harbor Hills Country Club

6027 SPINNAKER LOOP, LADY LAKE, FL, 3215..., Lady Lake, FL 32159

$399,000

3 beds

2 baths

1,950 sq ft

House

6027 SPINNAKER LOOP, LADY LAKE, FL, 3215...

Community: Harbor Hills Country Club

Sun City Center

$227,000

2 beds

2 baths

1,266 sq ft

House

1205 CHEVY CHASE DR, SUN CITY CENTER, FL...

Community: Sun City Center

Traditions at Lake Ruby

4068 CARTERET DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884

$289,250

3 beds

2 baths

1,928 sq ft

House

4068 CARTERET DR, WINTER HAVEN, FL, 3388...

Community: Traditions at Lake Ruby

Twin Lakes

2756 GREENLANDS ST, SAINT CLOUD, FL, 347..., Saint Cloud, FL 34772

$349,900

2 beds

2 baths

1,624 sq ft

House

2756 GREENLANDS ST, SAINT CLOUD, FL, 347...

Community: Twin Lakes

Plantation at Leesburg

24429 MADEWOOD AVE, LEESBURG, FL, 34748, Leesburg, FL 34748

$369,000

2 beds

2 baths

2,104 sq ft

House

24429 MADEWOOD AVE, LEESBURG, FL, 34748

Community: Plantation at Leesburg

Harbor Hills Country Club

39331 TREELINE DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$460,000

3 beds

3 baths

2,086 sq ft

House

39331 TREELINE DR, LADY LAKE, FL, 32159

Community: Harbor Hills Country Club

Twin Lakes

2491 YELLOW BRICK RD, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34772

$304,900

2 beds

2 baths

1,464 sq ft

Halfplex

2491 YELLOW BRICK RD, SAINT CLOUD, FL, 3...

Community: Twin Lakes

Del Webb Orlando

333 NAVARRA LN, DAVENPORT, FL, 33837, Davenport, FL 33837

$449,500

3 beds

2 baths

2,028 sq ft

House

333 NAVARRA LN, DAVENPORT, FL, 33837

Community: Del Webb Orlando

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

Questions? Call us: (689) 407-5757

Solivita

729 SAN RAPHAEL ST, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$524,900

4 beds

4 baths

2,616 sq ft

House

729 SAN RAPHAEL ST, KISSIMMEE, FL, 34759

Community: Solivita

On Top of the World

8420 SW 92ND ST A, OCALA, FL, 34481, Ocala, FL 34481

$179,900

2 beds

2 baths

1,366 sq ft

Villa

8420 SW 92ND ST A, OCALA, FL, 34481

Community: On Top of the World

The Villages®

7675 COUNTY ROAD 109E, LADY LAKE, FL, 32..., Lady Lake, FL 32159

$234,900

3 beds

2 baths

1,568 sq ft

Manufactured Home

7675 COUNTY ROAD 109E, LADY LAKE, FL, 32...

Community: The Villages®

Ocala Preserve

5662 NW 40TH PL, OCALA, FL, 34482, Ocala, FL 34482

$395,900

3 beds

2 baths

1,862 sq ft

House

5662 NW 40TH PL, OCALA, FL, 34482

Community: Ocala Preserve

Stone Creek

9532 SW 70TH LOOP, OCALA, FL, 34481, Ocala, FL 34481

$568,865

3 beds

3 baths

2,773 sq ft

House

9532 SW 70TH LOOP, OCALA, FL, 34481

Community: Stone Creek

Tampa Bay Golf and Country Club

10048 CLEGHORN DR, SAN ANTONIO, FL, 3357..., San Antonio, FL 33576

$387,000

3 beds

2 baths

2,229 sq ft

House

10048 CLEGHORN DR, SAN ANTONIO, FL, 3357...

Community: Tampa Bay Golf and Country Club

Sullivan Ranch

30120 HACKNEY LOOP, MOUNT DORA, FL, 3275..., Mount Dora, FL 32757

$615,000

4 beds

4 baths

3,307 sq ft

House

30120 HACKNEY LOOP, MOUNT DORA, FL, 3275...

Community: Sullivan Ranch

Solivita

531 BARCELONA DR, POINCIANA, FL, 34759, Poinciana, FL 34759

$379,900

3 beds

2 baths

1,966 sq ft

House

531 BARCELONA DR, POINCIANA, FL, 34759

Community: Solivita

The Villages®

$384,000

3 beds

2 baths

1,912 sq ft

House

17755 SE 85TH ELLERBE AVE, THE VILLAGES,...

Community: The Villages®

Pennbrooke Fairways

32857 TIMBERWOOD DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$329,000

3 beds

2 baths

1,674 sq ft

House

32857 TIMBERWOOD DR, LEESBURG, FL, 34748

House

4298 NORTH COURSE LN, AVON PARK, FL, 338...

Community: Highlands Ridge

Latitude Margaritaville

239 ISLAND BREEZE AVE, DAYTONA BEACH, FL..., Daytona Beach, FL 32124

$497,900

2 beds

2 baths

1,503 sq ft

House

239 ISLAND BREEZE AVE, DAYTONA BEACH, FL...

Community: Latitude Margaritaville

Thunderbird Hill

3922 SUNBIRD CIR, SEBRING, FL, 33872, Sebring, FL 33872

$205,000

2 beds

2 baths

1,209 sq ft

Villa

3922 SUNBIRD CIR, SEBRING, FL, 33872

Community: Thunderbird Hill

Legacy of Leesburg

27536 STONEY BROOK DR, LEESBURG, FL, 347..., Leesburg, FL 34748

$310,000

3 beds

2 baths

1,478 sq ft

House

27536 STONEY BROOK DR, LEESBURG, FL, 347...

Community: Legacy of Leesburg

Baytree

236 JUNIPER WAY, TAVARES, FL, 32778, Tavares, FL 32778

$240,000

2 beds

2 baths

1,456 sq ft

Villa

236 JUNIPER WAY, TAVARES, FL, 32778

Community: Baytree

Pelican Bay Daytona Beach

100 KINGBIRD CIR 1040, DAYTONA BEACH, FL..., Daytona Beach, FL 32119

$229,900

2 beds

2 baths

1,500 sq ft

Condo

100 KINGBIRD CIR 1040, DAYTONA BEACH, FL...

Community: Pelican Bay Daytona Beach

Oak Run

11741 SW 72ND CIR, OCALA, FL, 34476, Ocala, FL 34476

$299,000

3 beds

2 baths

1,544 sq ft

House

11741 SW 72ND CIR, OCALA, FL, 34476

Community: Oak Run

Lakes of Mount Dora

8339 BRIDGEPORT BAY CIR, MOUNT DORA, FL,..., Mount Dora, FL 32757

$883,000

4 beds

3 baths

2,602 sq ft

House

8339 BRIDGEPORT BAY CIR, MOUNT DORA, FL,...

Community: Lakes of Mount Dora

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

Questions? Call us: (689) 407-5757

The Villages®

$309,000

2 beds

2 baths

1,156 sq ft

House

790 BLAKE LN, THE VILLAGES, FL, 32162

Community: The Villages®

Thunderbird Hill

3716 SUNBIRD CIR, SEBRING, FL, 33872, Sebring, FL 33872

$205,000

2 beds

2 baths

1,080 sq ft

Villa

3716 SUNBIRD CIR, SEBRING, FL, 33872

Community: Thunderbird Hill

Oak Run

11427 SW 82ND AVE, OCALA, FL, 34481, Ocala, FL 34481

$339,000

3 beds

4 baths

2,074 sq ft

House

11427 SW 82ND AVE, OCALA, FL, 34481

Community: Oak Run

On Top of the World

8580 SW 90TH LN B, OCALA, FL, 34481, Ocala, FL 34481

$164,900

2 beds

2 baths

1,368 sq ft

House

8580 SW 90TH LN B, OCALA, FL, 34481

Community: On Top of the World

The Villages®

$764,900

3 beds

3 baths

2,125 sq ft

House

4384 PEZZULLO CIR, THE VILLAGES, FL, 321...

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.

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

1,503 sq ft

Villa

4 beds

2 baths

1,808 sq ft

House

3 beds

2 baths

1,863 sq ft

House

2 beds

2 baths

1,346 sq ft

House

4 beds

3 baths

2,443 sq ft

House

2 beds

2 baths

1,541 sq ft

Villa

2 beds

2 baths

1,571 sq ft

Villa

3 beds

2 baths

1,950 sq ft

House

2 beds

2 baths

1,266 sq ft

House

3 beds

2 baths

1,928 sq ft

House

2 beds

2 baths

1,624 sq ft

House

2 beds

2 baths

2,104 sq ft

House

3 beds

3 baths

2,086 sq ft

House

2 beds

2 baths

1,464 sq ft

Halfplex

3 beds

2 baths

2,028 sq ft

House

4 beds

4 baths

2,616 sq ft

House

2 beds

2 baths

1,366 sq ft

Villa

3 beds

2 baths

1,568 sq ft

Manufactured Home

3 beds

2 baths

1,862 sq ft

House

3 beds