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

3,648 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 - $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

$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

1015 HAREFIELD CIR # 1015, SUN CITY CENT...

Community: Sun City Center

Breakaway Trails

5 LAKE ISLE WAY, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$565,700

3 beds

3 baths

2,204 sq ft

House

5 LAKE ISLE WAY, ORMOND BEACH, FL, 32174

Community: Breakaway Trails

On Top of the World

9748 SW 99TH AVE, OCALA, FL, 34481, Ocala, FL 34481

$165,000

2 beds

2 baths

1,100 sq ft

House

9748 SW 99TH AVE, OCALA, FL, 34481

Community: On Top of the World

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

Questions? Call us: (689) 407-5757

Spruce Creek South

17728 SE 97TH AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$220,000

2 beds

2 baths

1,390 sq ft

House

17728 SE 97TH AVE, SUMMERFIELD, FL, 3449...

Community: Spruce Creek South

Venetian Bay

3211 MODENA WAY, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168

$949,132

3 beds

3 baths

2,542 sq ft

House

3211 MODENA WAY, NEW SMYRNA BEACH, FL, 3...

Community: Venetian Bay

Sun City Center

$284,900

3 beds

2 baths

1,322 sq ft

House

2335 E DEL WEBB BLVD, SUN CITY CENTER, F...

Community: Sun City Center

Spruce Creek Preserve

11335 SW 138TH LN, DUNNELLON, FL, 34432, Dunnellon, FL 34432

$244,500

2 beds

2 baths

1,464 sq ft

House

11335 SW 138TH LN, DUNNELLON, FL, 34432

Community: Spruce Creek Preserve

Latitude Margaritaville

568 LANDSHARK BLVD, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124

$389,000

2 beds

2 baths

1,482 sq ft

House

568 LANDSHARK BLVD, DAYTONA BEACH, FL, 3...

Community: Latitude Margaritaville

Oak Run

10777 SW 71ST CIR, OCALA, FL, 34476, Ocala, FL 34476

$335,000

3 beds

3 baths

2,082 sq ft

House

10777 SW 71ST CIR, OCALA, FL, 34476

Community: Oak Run

Mirada

31524 MAGNA GULF LOOP, SAN ANTONIO, FL, ..., San Antonio, FL 33576

$305,000

2 beds

2 baths

1,405 sq ft

Villa

31524 MAGNA GULF LOOP, SAN ANTONIO, FL, ...

Community: Mirada

Colonnades

4904 GOLDENVIEW LN, LAKELAND, FL, 33811, Lakeland, FL 33811

$240,000

2 beds

2 baths

1,523 sq ft

House

4904 GOLDENVIEW LN, LAKELAND, FL, 33811

Community: Colonnades

Majestic Oaks Ocala

8636 SW 54TH CT, OCALA, FL, 34476, Ocala, FL 34476

$399,900

3 beds

2 baths

2,213 sq ft

House

8636 SW 54TH CT, OCALA, FL, 34476

Community: Majestic Oaks Ocala

The Villages®

$235,000

2 beds

2 baths

1,156 sq ft

Villa

2912 BARBOZA DR, THE VILLAGES, FL, 32162

Community: The Villages®

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

Questions? Call us: (689) 407-5757

Lake James

$497,000

3 beds

2 baths

2,175 sq ft

House

8152 LAKE JAMES DR, LAKELAND, FL, 33810

Community: Lake James

Stone Creek

6670 SW 97TH TERRACE RD, OCALA, FL, 3448..., Ocala, FL 34481

$365,000

3 beds

2 baths

2,122 sq ft

House

6670 SW 97TH TERRACE RD, OCALA, FL, 3448...

Community: Stone Creek

Pelican Bay Daytona Beach

224 BOB WHITE CT # 224, DAYTONA BEACH, F..., Daytona Beach, FL 32119

$240,000

3 beds

3 baths

1,668 sq ft

Condo

224 BOB WHITE CT # 224, DAYTONA BEACH, F...

Community: Pelican Bay Daytona Beach

Legacy of Leesburg

27238 STONEY BROOK DR, LEESBURG, FL, 347..., Leesburg, FL 34748

$450,000

4 beds

2 baths

2,585 sq ft

House

27238 STONEY BROOK DR, LEESBURG, FL, 347...

Community: Legacy of Leesburg

On Top of the World

8738 SW 95TH LN B, OCALA, FL, 34481, Ocala, FL 34481

$159,900

2 beds

2 baths

1,644 sq ft

Villa

8738 SW 95TH LN B, OCALA, FL, 34481

Community: On Top of the World

Cresswind at Victoria Gardens

123 AVENHAM DR, DELAND, FL, 32724, Deland, FL 32724

$374,900

3 beds

2 baths

1,894 sq ft

House

123 AVENHAM DR, DELAND, FL, 32724

Community: Cresswind at Victoria Gardens

On Top of the World

8674 SW 94TH CIR, OCALA, FL, 34481, Ocala, FL 34481

$442,000

3 beds

3 baths

2,450 sq ft

House

8674 SW 94TH CIR, OCALA, FL, 34481

Community: On Top of the World

Spruce Creek South

17831 SE 96TH AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$214,999

2 beds

2 baths

1,118 sq ft

House

17831 SE 96TH AVE, SUMMERFIELD, FL, 3449...

Community: Spruce Creek South

On Top of the World

8814 SW 93RD LN B, OCALA, FL, 34481, Ocala, FL 34481

$159,900

2 beds

2 baths

1,411 sq ft

Villa

8814 SW 93RD LN B, OCALA, FL, 34481

Community: On Top of the World

Oak Run

7466 SW 111TH LN, OCALA, FL, 34476, Ocala, FL 34476

$215,000

2 beds

2 baths

1,121 sq ft

House

7466 SW 111TH LN, OCALA, FL, 34476

Villa

802 CHIPPER DR, SUN CITY CENTER, FL, 335...

Condo

7545 LAUREATE BLVD UNIT 7203, ORLANDO, F...

Community: Gatherings of Lake Nona

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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

3,648 homes near Winter Garden

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

108 communities near Winter Garden

3,648 homes near Winter Garden

2 beds

2 baths

1,198 sq ft

House

2 beds

2 baths

1,642 sq ft

Condo

2 beds

2 baths

1,448 sq ft

Condo

3 beds

3 baths

2,204 sq ft

House

2 beds

2 baths

1,100 sq ft

House

2 beds

2 baths

1,390 sq ft

House

3 beds

3 baths

2,542 sq ft

House

3 beds

2 baths

1,322 sq ft

House

2 beds

2 baths

1,464 sq ft

House

2 beds

2 baths

1,482 sq ft

House

3 beds

3 baths

2,082 sq ft

House

2 beds

2 baths

1,405 sq ft

Villa

2 beds

2 baths

1,523 sq ft

House

3 beds

2 baths

2,213 sq ft

House

2 beds

2 baths

1,156 sq ft

Villa

3 beds

2 baths

2,175 sq ft

House

3 beds

2 baths

2,122 sq ft

House

3 beds

3 baths

1,668 sq ft

Condo

4 beds

2 baths

2,585 sq ft

House

2 beds