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

3,964 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)

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

1 2 3

Oak Run

11447 SW 69TH CIR, OCALA, FL, 34476, Ocala, FL 34476

$239,900

2 beds

2 baths

1,687 sq ft

House

11447 SW 69TH CIR, OCALA, FL, 34476

Community: Oak Run

Sun City Center

$259,000

2 beds

2 baths

1,516 sq ft

House

317 GREEN MANOR DR, SUN CITY CENTER, FL,...

445 NOBLE FAIRE DR, SUN CITY CENTER, FL,...

Community: Sun City Center

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

Questions? Call us: (689) 407-5757

Latitude Margaritaville

623 MARGARITAVILLE AVE, DAYTONA BEACH, F..., Daytona Beach, FL 32124

$399,000

2 beds

2 baths

1,464 sq ft

Villa

623 MARGARITAVILLE AVE, DAYTONA BEACH, F...

Community: Latitude Margaritaville

The Villages®

$575,000

3 beds

2 baths

1,965 sq ft

House

1881 SASSPARILLA WAY, THE VILLAGES, FL, ...

Community: The Villages®

The Villages®

$525,900

3 beds

2 baths

1,986 sq ft

House

1121 ALCOVE LOOP, THE VILLAGES, FL, 3216...

Community: The Villages®

The Villages®

$749,000

4 beds

3 baths

2,286 sq ft

House

3138 AUREA PL, THE VILLAGES, FL, 32163

Community: The Villages®

Venetian Bay

3229 MEDICI BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168

$750,000

3 beds

3 baths

2,377 sq ft

House

3229 MEDICI BLVD, NEW SMYRNA BEACH, FL, ...

Community: Venetian Bay

Venetian Bay

637 MARISOL DR, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168

$499,000

3 beds

2 baths

1,826 sq ft

House

637 MARISOL DR, NEW SMYRNA BEACH, FL, 32...

Community: Venetian Bay

Southshore Bay

17249 STAR BANKS ST, WIMAUMA, FL, 33598, Wimauma, FL 33598

$425,000

3 beds

3 baths

2,128 sq ft

House

17249 STAR BANKS ST, WIMAUMA, FL, 33598

Community: Southshore Bay

The Lakes at Harmony

7651 FIVE OAKS DR, HARMONY, FL, 34773, Harmony, FL 34773

$520,000

3 beds

3 baths

2,355 sq ft

House

7651 FIVE OAKS DR, HARMONY, FL, 34773

Community: The Lakes at Harmony

Pine Run Estates

10040 SW 93RD CT, OCALA, FL, 34481, Ocala, FL 34481

$160,000

2 beds

2 baths

1,040 sq ft

House

10040 SW 93RD CT, OCALA, FL, 34481

Community: Pine Run Estates

Stonecrest

11702 SE 173RD LANE RD, SUMMERFIELD, FL,..., Summerfield, FL 34491

$442,000

3 beds

2 baths

2,009 sq ft

House

11702 SE 173RD LANE RD, SUMMERFIELD, FL,...

Community: Stonecrest

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

Questions? Call us: (689) 407-5757

Esplanade at Highland Ranch

1028 SADIE RIDGE RD, CLERMONT, FL, 34715, Clermont, FL 34715

$569,000

4 beds

4 baths

2,560 sq ft

House

1028 SADIE RIDGE RD, CLERMONT, FL, 34715

Community: Esplanade at Highland Ranch

The Villages®

$310,000

2 beds

2 baths

1,108 sq ft

Villa

880 RADCLIFE BEREA PL, THE VILLAGES, FL,...

Community: The Villages®

The Villages®

603 SAN PEDRO DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$369,900

3 beds

2 baths

1,636 sq ft

House

603 SAN PEDRO DR, LADY LAKE, FL, 32159

Community: The Villages®

On Top of the World

9729 SW 97TH ST, OCALA, FL, 34481, Ocala, FL 34481

$239,900

2 beds

2 baths

1,230 sq ft

House

9729 SW 97TH ST, OCALA, FL, 34481

Community: On Top of the World

Mirada

31354 CABANA RYE AVE, SAN ANTONIO, FL, 3..., San Antonio, FL 33576

$280,000

2 beds

2 baths

1,405 sq ft

Villa

31354 CABANA RYE AVE, SAN ANTONIO, FL, 3...

Community: Mirada

Del Webb Orlando

516 PAMPLONA PL, DAVENPORT, FL, 33837, Davenport, FL 33837

$314,900

2 beds

2 baths

1,445 sq ft

House

516 PAMPLONA PL, DAVENPORT, FL, 33837

Community: Del Webb Orlando

The Villages®

$435,000

3 beds

2 baths

1,562 sq ft

House

511 CHULA VISTA AVE, THE VILLAGES, FL, 3...

Community: The Villages®

On Top of the World

8423 SW 82ND CIR, OCALA, FL, 34481, Ocala, FL 34481

$381,000

3 beds

2 baths

2,283 sq ft

House

8423 SW 82ND CIR, OCALA, FL, 34481

Community: On Top of the World

On Top of the World

8463 SW 84TH LOOP, OCALA, FL, 34481, Ocala, FL 34481

$367,000

3 beds

2 baths

2,431 sq ft

House

8463 SW 84TH LOOP, OCALA, FL, 34481

Community: On Top of the World

Ocala Palms

2093 NW 50TH CIR, OCALA, FL, 34482, Ocala, FL 34482

$249,900

2 beds

2 baths

1,270 sq ft

House

2093 NW 50TH CIR, OCALA, FL, 34482

House

9090 SE 135TH LOOP, SUMMERFIELD, FL, 344...

House

4985 RAINBOW TROUT RD, TAVARES, FL, 3277...

Community: Royal Harbor

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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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3,964 homes near Winter Garden

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

106 communities near Winter Garden

3,964 homes near Winter Garden

2 beds

2 baths

1,687 sq ft

House

2 beds

2 baths

1,516 sq ft

House

3 beds

2 baths

1,845 sq ft

House

2 beds

2 baths

1,550 sq ft

House

3 beds

3 baths

2,637 sq ft

House

2 beds

2 baths

1,464 sq ft

Villa

3 beds

2 baths

1,965 sq ft

House

3 beds

2 baths

1,986 sq ft

House

4 beds

3 baths

2,286 sq ft

House

3 beds

3 baths

2,377 sq ft

House

3 beds

2 baths

1,826 sq ft

House

3 beds

3 baths

2,128 sq ft

House

3 beds

3 baths

2,355 sq ft

House

2 beds

2 baths

1,040 sq ft

House

3 beds

2 baths

2,009 sq ft

House

4 beds

4 baths

2,560 sq ft

House

2 beds

2 baths

1,108 sq ft

Villa

3 beds

2 baths

1,636 sq ft

House

2 beds

2 baths

1,230 sq ft

House

2 beds