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

3,573 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 - $2Ms

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 - $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

$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 (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 - $500Ks

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 - $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

$200Ks - $200Ks

Cypress Lakes, Lakeland, FL

Resale Only | 55+ age-restricted | Built 1987 - 2016 | 1,604 homes

5 rating (3 reviews)

Lake Ashton

$200Ks - $500Ks

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

$300Ks - $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 - $900Ks

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...

$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 - $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 - $400Ks

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

$300Ks - $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

4.3 rating (15 reviews)

Del Webb Orlando

$200Ks - $400Ks

Del Webb Orlando, Davenport, FL

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

No reviews yet

Pine Run Estates

<$100k - $400Ks

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

Solivita

1014 UMBRIA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$269,900

2 beds

2 baths

1,365 sq ft

House

1014 UMBRIA DR, KISSIMMEE, FL, 34759

Community: Solivita

Spruce Creek North

10980 SW 62ND AVENUE RD, OCALA, FL, 3447..., Ocala, FL 34476

$201,500

3 beds

2 baths

1,526 sq ft

House

10980 SW 62ND AVENUE RD, OCALA, FL, 3447...

Community: Spruce Creek North

Plantation at Leesburg

3733 PLANTATION BLVD, LEESBURG, FL, 3474..., Leesburg, FL 34748

$379,900

3 beds

3 baths

2,868 sq ft

House

3733 PLANTATION BLVD, LEESBURG, FL, 3474...

Community: Plantation at Leesburg

Trilogy® Orlando

228 BAYOU BEND RD, GROVELAND, FL, 34736, Groveland, FL 34736

$465,000

2 beds

2 baths

2,197 sq ft

House

228 BAYOU BEND RD, GROVELAND, FL, 34736

Community: Trilogy® Orlando

Del Webb Sunbridge

6507 TRAILBLAZE BND, SAINT CLOUD, FL, 34..., Saint Cloud, FL 34771

$374,990

3 beds

3 baths

1,744 sq ft

Townhouse

6507 TRAILBLAZE BND, 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

Del Webb Sunbridge

2904 VOYAGER AVE, SAINT CLOUD, FL, 34771, Saint Cloud, FL 34771

$409,990

3 beds

3 baths

1,744 sq ft

Townhouse

2904 VOYAGER AVE, SAINT CLOUD, FL, 34771

Community: Del Webb Sunbridge

Spruce Creek Country Club

13535 SE 97TH TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491

$429,000

3 beds

3 baths

2,262 sq ft

House

13535 SE 97TH TERRACE RD, SUMMERFIELD, F...

Community: Spruce Creek Country Club

Stone Creek

5953 SW 82ND TERRACE RD, OCALA, FL, 3448..., Ocala, FL 34481

$548,200

3 beds

3 baths

2,483 sq ft

House

5953 SW 82ND TERRACE RD, OCALA, FL, 3448...

Community: Stone Creek

Del Webb Minneola

1336 ORANGE VALLEY RD, MINNEOLA, FL, 347..., Minneola, FL 34715

$448,000

2 beds

2 baths

1,405 sq ft

House

1336 ORANGE VALLEY RD, MINNEOLA, FL, 347...

Community: Del Webb Minneola

Stone Creek

5226 SW 88TH CIR, OCALA, FL, 34481, Ocala, FL 34481

$431,320

2 beds

2 baths

1,889 sq ft

House

5226 SW 88TH CIR, OCALA, FL, 34481

Community: Stone Creek

Del Webb Minneola

1389 ZESTY CITRUS LN, MINNEOLA, FL, 3471..., Minneola, FL 34715

$773,000

2 beds

3 baths

2,114 sq ft

House

1389 ZESTY CITRUS LN, MINNEOLA, FL, 3471...

Community: Del Webb Minneola

Lake Ashton

4188 MUIRFIELD LOOP, LAKE WALES, FL, 338..., Lake Wales, FL 33859

$299,900

2 beds

2 baths

1,520 sq ft

House

4188 MUIRFIELD LOOP, LAKE WALES, FL, 338...

Community: Lake Ashton

Del Webb Sunbridge

6480 BARNSTORM WAY, SAINT CLOUD, FL, 347..., Saint Cloud, FL 34771

$399,990

3 beds

3 baths

1,744 sq ft

Townhouse

6480 BARNSTORM WAY, SAINT CLOUD, FL, 347...

Community: Del Webb Sunbridge

Del Webb Sunbridge

6488 BARNSTORM WAY, SAINT CLOUD, FL, 347..., Saint Cloud, FL 34771

$424,990

3 beds

3 baths

1,767 sq ft

Townhouse

6488 BARNSTORM WAY, SAINT CLOUD, FL, 347...

Community: Del Webb Sunbridge

Del Webb Sunbridge

6476 BARNSTORM WAY, SAINT CLOUD, FL, 347..., Saint Cloud, FL 34771

$424,990

3 beds

3 baths

1,767 sq ft

Townhouse

6476 BARNSTORM WAY, SAINT CLOUD, FL, 347...

Community: Del Webb Sunbridge

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

Questions? Call us: (689) 407-5757

Stone Creek

8199 SW 52ND LANE RD, OCALA, FL, 34481, Ocala, FL 34481

$361,580

3 beds

2 baths

1,662 sq ft

House

8199 SW 52ND LANE RD, OCALA, FL, 34481

Community: Stone Creek

Del Webb Sunbridge

6553 ROVER WAY, SAINT CLOUD, FL, 34771, Saint Cloud, FL 34771

$529,990

3 beds

3 baths

2,018 sq ft

House

6553 ROVER WAY, SAINT CLOUD, FL, 34771

Community: Del Webb Sunbridge

Stone Creek

8249 SW 52ND LANE RD, OCALA, FL, 34481, Ocala, FL 34481

$369,310

4 beds

2 baths

1,850 sq ft

House

8249 SW 52ND LANE RD, OCALA, FL, 34481

Community: Stone Creek

Stone Creek

5230 SW 88TH CIR, OCALA, FL, 34481, Ocala, FL 34481

$408,500

2 beds

2 baths

1,948 sq ft

House

5230 SW 88TH CIR, OCALA, FL, 34481

Community: Stone Creek

Stone Creek

5222 SW 88TH CIR, OCALA, FL, 34481, Ocala, FL 34481

$447,600

2 beds

3 baths

2,080 sq ft

House

5222 SW 88TH CIR, OCALA, FL, 34481

Community: Stone Creek

Stone Creek

5295 SW 87TH TER, OCALA, FL, 34481, Ocala, FL 34481

$400,370

2 beds

2 baths

1,670 sq ft

House

5295 SW 87TH TER, OCALA, FL, 34481

Community: Stone Creek

Majestic Oaks Ocala

5421 SW 82ND LN, OCALA, FL, 34476, Ocala, FL 34476

$312,270

2 beds

2 baths

1,433 sq ft

House

5421 SW 82ND LN, OCALA, FL, 34476

Community: Majestic Oaks Ocala

Del Webb Minneola

1104 WESTERN BLUE WAY, MINNEOLA, FL, 347..., Minneola, FL 34715

$624,000

3 beds

2 baths

1,889 sq ft

House

1104 WESTERN BLUE WAY, MINNEOLA, FL, 347...

Community: Del Webb Minneola

Marco Polo Village

10876 SW 53RD CIR, OCALA, FL, 34476, Ocala, FL 34476

$315,000

3 beds

2 baths

1,755 sq ft

House

10876 SW 53RD CIR, OCALA, FL, 34476

Community: Marco Polo Village

The Villages®

$275,000

2 beds

2 baths

1,192 sq ft

House

1405 W SCHWARTZ BLVD, THE VILLAGES, FL, ...

Community: The Villages®

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

Questions? Call us: (689) 407-5757

The Villages®

$295,000

2 beds

2 baths

1,143 sq ft

Villa

1615 NAVIDAD ST, THE VILLAGES, FL, 32162

Community: The Villages®

SummerGlen

16299 SW 14TH AVENUE RD, OCALA, FL, 3447..., Ocala, FL 34473

$273,000

2 beds

2 baths

1,820 sq ft

House

16299 SW 14TH AVENUE RD, OCALA, FL, 3447...

Community: SummerGlen

Tohoqua Reserve

2741 SERENITY MEADOW DR, KISSIMMEE, FL, ..., Kissimmee, FL 34744

$413,990

2 beds

2 baths

1,889 sq ft

House

2741 SERENITY MEADOW DR, KISSIMMEE, FL, ...

Community: Tohoqua Reserve

Marion Landing

8342 SW 65TH AVE, OCALA, FL, 34476, Ocala, FL 34476

$265,000

2 beds

2 baths

1,951 sq ft

House

8342 SW 65TH AVE, OCALA, FL, 34476

Community: Marion Landing

Oak Run

10919 SW 73RD CT, OCALA, FL, 34476, Ocala, FL 34476

$379,990

4 beds

3 baths

2,551 sq ft

House

10919 SW 73RD CT, OCALA, FL, 34476

Community: Oak Run

Oak Run

10864 SW 73RD CT, OCALA, FL, 34476, Ocala, FL 34476

$315,990

3 beds

2 baths

1,815 sq ft

House

10864 SW 73RD CT, OCALA, FL, 34476

Community: Oak Run

Oak Run

10899 SW 73RD CT, OCALA, FL, 34476, Ocala, FL 34476

$335,990

3 beds

2 baths

2,021 sq ft

House

10899 SW 73RD CT, OCALA, FL, 34476

Community: Oak Run

Venetian Bay

706 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168

$479,990

3 beds

3 baths

2,125 sq ft

House

706 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ...

Community: Venetian Bay

Bridgewater Landing

5732 STOCKPORT ST, RIVERVIEW, FL, 33578, Riverview, FL 33578

$350,000

2 beds

2 baths

1,693 sq ft

Villa

5732 STOCKPORT ST, RIVERVIEW, FL, 33578

Community: Bridgewater Landing

Summit Greens

2503 SQUAW CRK, CLERMONT, FL, 34711, Clermont, FL 34711

$429,900

3 beds

2 baths

1,919 sq ft

House

2503 SQUAW CRK, CLERMONT, FL, 34711

Villa

7066 SW 91ST CT, OCALA, FL, 34481

Community: Stone Creek

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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?

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3,573 homes near Winter Garden

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

106 communities near Winter Garden

3,573 homes near Winter Garden

2 beds

2 baths

1,365 sq ft

House

3 beds

2 baths

1,526 sq ft

House

3 beds

3 baths

2,868 sq ft

House

2 beds

2 baths

2,197 sq ft

House

3 beds

3 baths

1,744 sq ft

Townhouse

3 beds

3 baths

1,744 sq ft

Townhouse

3 beds

3 baths

2,262 sq ft

House

3 beds

3 baths

2,483 sq ft

House

2 beds

2 baths

1,405 sq ft

House

2 beds

2 baths

1,889 sq ft

House

2 beds

3 baths

2,114 sq ft

House

2 beds

2 baths

1,520 sq ft

House

3 beds

3 baths

1,744 sq ft

Townhouse

3 beds

3 baths

1,767 sq ft

Townhouse

3 beds

3 baths

1,767 sq ft

Townhouse

3 beds

2 baths

1,662 sq ft

House

3 beds

3 baths

2,018 sq ft

House

4 beds

2 baths

1,850 sq ft

House

2 beds

2 baths

1,948 sq ft

House

2 beds