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

1 2...3

Traditions at Lake Ruby

3923 BALDWIN LN, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884

$299,000

3 beds

2 baths

1,719 sq ft

House

3923 BALDWIN LN, WINTER HAVEN, FL, 33884

Community: Traditions at Lake Ruby

Solivita

663 IRVINE RANCH RD, POINCIANA, FL, 3475..., Poinciana, FL 34759

$418,000

3 beds

3 baths

2,307 sq ft

House

663 IRVINE RANCH RD, POINCIANA, FL, 3475...

Community: Solivita

Sun City Center

$184,900

2 beds

2 baths

1,182 sq ft

Condo

2320 MARKSMEN CT # 205, SUN CITY CENTER,...

Community: Sun City Center

Twin Lakes

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

$299,999

2 beds

2 baths

1,464 sq ft

Halfplex

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

Community: Twin Lakes

Lakes of Mount Dora

8045 WATERBURY WAY, MOUNT DORA, FL, 3275..., Mount Dora, FL 32757

$465,000

3 beds

2 baths

2,152 sq ft

House

8045 WATERBURY WAY, MOUNT DORA, FL, 3275...

Condo

2619 NEWCOMB CT, SUN CITY CENTER, FL, 33...

2555 YELLOW BRICK RD, SAINT CLOUD, FL, 3...

Condo

1508 INGRAM DR # 20, SUN CITY CENTER, FL...

Community: Sun City Center

Latitude Margaritaville

786 JOLLYMON WAY, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124

$729,900

3 beds

3 baths

2,392 sq ft

House

786 JOLLYMON WAY, DAYTONA BEACH, FL, 321...

Community: Latitude Margaritaville

The Villages®

1204 MARIA CT, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$319,000

2 beds

2 baths

2,182 sq ft

House

1204 MARIA CT, LADY LAKE, FL, 32159

Community: The Villages®

Venetian Bay

3362 MARSILI AVE, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168

$399,000

3 beds

2 baths

1,952 sq ft

House

3362 MARSILI AVE, NEW SMYRNA BEACH, FL, ...

Community: Venetian Bay

Majestic Oaks Ocala

8650 SW 55TH CT, OCALA, FL, 34476, Ocala, FL 34476

$359,000

3 beds

2 baths

2,234 sq ft

House

8650 SW 55TH CT, OCALA, FL, 34476

Community: Majestic Oaks Ocala

Marion Landing

6490 SW 84TH ST, OCALA, FL, 34476, Ocala, FL 34476

$258,000

2 beds

2 baths

1,758 sq ft

House

6490 SW 84TH ST, OCALA, FL, 34476

Community: Marion Landing

The Villages®

19201 SANDALWOOD DR # 19201, WILDWOOD, F..., Wildwood, FL 34785

$135,000

1 beds

1 baths

872 sq ft

Condo

19201 SANDALWOOD DR # 19201, WILDWOOD, F...

Community: The Villages®

Solivita

141 LEMON GROVE DR, POINCIANA, FL, 34759, Poinciana, FL 34759

$664,900

4 beds

5 baths

2,917 sq ft

House

141 LEMON GROVE DR, POINCIANA, FL, 34759

Community: Solivita

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

Questions? Call us: (689) 407-5757

Four Seasons at Orlando

1991 KEY BAY TRL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747

$360,000

2 beds

2 baths

1,437 sq ft

Villa

1991 KEY BAY TRL, KISSIMMEE, FL, 34747

Community: Four Seasons at Orlando

Huntington at Hunter's Ridge

71 WRENDALE LOOP, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174

$358,000

2 beds

2 baths

1,598 sq ft

Villa

71 WRENDALE LOOP, ORMOND BEACH, FL, 3217...

Community: Huntington at Hunter's Ridge

Sun City Center

$140,000

2 beds

2 baths

952 sq ft

Condo

413 LAKE POINT CT # 4B, SUN CITY CENTER,...

Community: Sun City Center

Sun City Center

$265,000

2 beds

1 baths

1,344 sq ft

House

906 HACIENDA DR, SUN CITY CENTER, FL, 33...

Community: Sun City Center

Sun City Center

$195,000

2 beds

2 baths

1,448 sq ft

Condo

2109 HARLESTON PL # 2109, SUN CITY CENTE...

Community: Sun City Center

JB Ranch

6365 SW 88TH LOOP, OCALA, FL, 34476, Ocala, FL 34476

$299,999

2 beds

2 baths

1,811 sq ft

House

6365 SW 88TH LOOP, OCALA, FL, 34476

Community: JB Ranch

Venetian Bay

2948 BELLA FLORE TER, NEW SMYRNA BEACH, ..., New Smyrna Beach, FL 32168

$979,000

3 beds

3 baths

2,034 sq ft

House

2948 BELLA FLORE TER, NEW SMYRNA BEACH, ...

Community: Venetian Bay

Palm Cay

10648 SW 83RD AVE, OCALA, FL, 34481, Ocala, FL 34481

$215,900

2 beds

2 baths

1,340 sq ft

House

10648 SW 83RD AVE, OCALA, FL, 34481

Community: Palm Cay

Sun City Center

$259,000

2 beds

2 baths

1,456 sq ft

Condo

2433 KENSINGTON GREENS DR, SUN CITY CENT...

Community: Sun City Center

The Villages®

$443,000

3 beds

2 baths

1,918 sq ft

House

7243 SE 172ND LEGACY LN, THE VILLAGES, F...

House

2789 SOUTHLAND ST, SAINT CLOUD, FL, 3477...

Community: Twin Lakes

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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

3,703 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

1,719 sq ft

House

3 beds

3 baths

2,307 sq ft

House

2 beds

2 baths

1,182 sq ft

Condo

2 beds

2 baths

1,464 sq ft

Halfplex

3 beds

2 baths

2,152 sq ft

House

2 beds

2 baths

1,406 sq ft

House

2 beds

2 baths

1,374 sq ft

Villa

4 beds

2 baths

1,936 sq ft

House

2 beds

2 baths

963 sq ft

Condo

2 beds

2 baths

1,008 sq ft

House

3 beds

2 baths

1,582 sq ft

House

2 beds

2 baths

1,557 sq ft

House

1 beds

2 baths

800 sq ft

Condo

2 beds

2 baths

1,144 sq ft

House

2 beds

2 baths

1,346 sq ft

Villa

3 beds

2 baths

1,657 sq ft

House

2 beds

2 baths

1,498 sq ft

House

2 beds

2 baths

1,857 sq ft

Condo

3 beds

3 baths

2,392 sq ft

House

2 beds