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

3,551 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 - $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 - $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 - $600Ks

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, FL? 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 - $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 - $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

$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 - $600Ks

Twin Lakes, St. Cloud, FL

New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes

Pelican Bay Daytona Beach

$100Ks - $400Ks

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, FL? 55places can help!

Questions? Call us: (689) 407-5757

4.7 rating (3 reviews)

Spruce Creek South

$100Ks - $400Ks

Spruce Creek South, Summerfield, FL

Resale Only | 55+ age-restricted | Built 1989 - 1995 | 1,650 homes

4.7 rating (11 reviews)

Valencia Lakes

$200Ks - $700Ks

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

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 - $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)

VillageWalk at Lake Nona

$300Ks - $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, FL? 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 - $400Ks

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

Breakaway Trails

$400Ks - $800Ks

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, FL? 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

4.4 rating (16 reviews)

Del Webb Orlando

$300Ks - $400Ks

Del Webb Orlando, Davenport, FL

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

Pine Run Estates

$100Ks - $300Ks

Pine Run Estates, Ocala, FL

Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 homes

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

Esplanade at Wiregrass Ra...

$400Ks - $1Ms

Esplanade at Wiregrass Ra..., Wesley Chapel, FL

New and Resale | 55+ age-restricted | Built 2019 - present | 868 homes

14272 SW 112TH CIR, DUNNELLON, FL, 34432

Community: Spruce Creek Preserve

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

Questions? Call us: (689) 407-5757

On Top of the World

9770 SW 97TH PL, OCALA, FL, 34481, Ocala, FL 34481

$254,900

3 beds

3 baths

1,736 sq ft

House

9770 SW 97TH PL, OCALA, FL, 34481

Community: On Top of the World

Gatherings of Lake Nona

7557 LAUREATE BLVD UNIT 6208, ORLANDO, F..., Orlando, FL 32827

$366,300

2 beds

2 baths

1,445 sq ft

Condo

7557 LAUREATE BLVD UNIT 6208, ORLANDO, F...

Community: Gatherings of Lake Nona

The Villages®

$915,000

4 beds

3 baths

2,296 sq ft

House

4878 CHITTY CHATTY RUN, THE VILLAGES, FL...

Community: The Villages®

The Villages®

$300,000

2 beds

2 baths

1,156 sq ft

Villa

297 EMMALEE PL, THE VILLAGES, FL, 32162

Community: The Villages®

The Villages®

$500,000

4 beds

3 baths

2,202 sq ft

House

164 PALERMO PL, THE VILLAGES, FL, 32159

Community: The Villages®

The Villages®

$465,000

3 beds

2 baths

1,956 sq ft

House

791 ENISGROVE WAY, THE VILLAGES, FL, 321...

Community: The Villages®

The Villages®

$365,000

2 beds

2 baths

1,152 sq ft

Villa

3627 FULCRUM PL, THE VILLAGES, FL, 32163

Community: The Villages®

New The Villages®

729 HERNANDEZ DR, THE VILLAGES, FL, 3215..., The Villages, FL 32159

$299,900

2 beds

2 baths

1,094 sq ft

House

729 HERNANDEZ DR, THE VILLAGES, FL, 3215...

Community: The Villages®

New The Villages®

748 HERNANDEZ DR, THE VILLAGES, FL, 3215..., The Villages, FL 32159

$319,000

2 beds

2 baths

1,078 sq ft

Villa

748 HERNANDEZ DR, THE VILLAGES, FL, 3215...

Community: The Villages®

New Venetian Bay

3078 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168

$329,500

3 beds

3 baths

1,614 sq ft

Townhouse

3078 MELETO BLVD, NEW SMYRNA BEACH, FL, ...

House

17979 SE 89TH ROTHWAY CT, THE VILLAGES, ...

Community: The Villages®

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

Questions? Call us: (689) 407-5757

Pelican Bay Daytona Beach

256 PALM SPARROW CT, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119

$229,000

2 beds

2 baths

1,146 sq ft

Halfplex

256 PALM SPARROW CT, DAYTONA BEACH, FL, ...

Community: Pelican Bay Daytona Beach

The Villages®

$1,300,000

3 beds

2 baths

2,403 sq ft

House

1579 MCELDOWNEY PL, THE VILLAGES, FL, 32...

Community: The Villages®

Ocala Palms

4547 NW 53RD AVENUE RD, OCALA, FL, 34482, Ocala, FL 34482

$439,990

2 beds

3 baths

2,056 sq ft

House

4547 NW 53RD AVENUE RD, OCALA, FL, 34482

Community: Ocala Palms

High Vista at Ridgewood Lakes

225 HIGH VISTA DR, DAVENPORT, FL, 33837, Davenport, FL 33837

$319,499

2 beds

2 baths

1,724 sq ft

House

225 HIGH VISTA DR, DAVENPORT, FL, 33837

Community: High Vista at Ridgewood Lakes

Ocala Palms

4529 NW 53RD AVENUE RD, OCALA, FL, 34482, Ocala, FL 34482

$449,990

2 beds

3 baths

2,056 sq ft

House

4529 NW 53RD AVENUE RD, OCALA, FL, 34482

Community: Ocala Palms

Ocala Preserve

3223 NW 52ND AVENUE RD, OCALA, FL, 34482, Ocala, FL 34482

$292,070

2 beds

3 baths

1,722 sq ft

Halfplex

3223 NW 52ND AVENUE RD, OCALA, FL, 34482

Community: Ocala Preserve

Spruce Creek Country Club

12546 SE 92ND TER, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$350,000

2 beds

2 baths

2,119 sq ft

House

12546 SE 92ND TER, SUMMERFIELD, FL, 3449...

Community: Spruce Creek Country Club

Four Seasons at Orlando

2074 FLORA PASS PL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747

$645,000

3 beds

2 baths

2,130 sq ft

House

2074 FLORA PASS PL, KISSIMMEE, FL, 34747

Community: Four Seasons at Orlando

The Villages®

515 LOMA PASEO DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$550,000

3 beds

2 baths

2,322 sq ft

House

515 LOMA PASEO DR, LADY LAKE, FL, 32159

Community: The Villages®

Oak Run

11615 SW 72ND CIR, OCALA, FL, 34476, Ocala, FL 34476

$364,885

3 beds

2 baths

2,110 sq ft

House

11615 SW 72ND CIR, OCALA, FL, 34476

House

17285 SE 85TH WILLOWICK CIR, THE VILLAGE...

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.

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

3,551 homes near Winter Garden

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

109 communities near Winter Garden

3,551 homes near Winter Garden

2 beds

2 baths

1,672 sq ft

House

4 beds

2 baths

1,751 sq ft

House

2 beds

2 baths

1,672 sq ft

House

3 beds

2 baths

1,680 sq ft

House

3 beds

2 baths

1,790 sq ft

House

3 beds

3 baths

1,736 sq ft

House

2 beds

2 baths

1,445 sq ft

Condo

4 beds

3 baths

2,296 sq ft

House

2 beds

2 baths

1,156 sq ft

Villa

4 beds

3 baths

2,202 sq ft

House

3 beds

2 baths

1,956 sq ft

House

2 beds

2 baths

1,152 sq ft

Villa

2 beds

2 baths

1,094 sq ft

House

2 beds

2 baths

1,078 sq ft

Villa

3 beds

3 baths

1,614 sq ft

Townhouse

3 beds

2 baths

2,000 sq ft

House

3 beds

2 baths

1,918 sq ft

House

4 beds

3 baths

2,550 sq ft

House

2 beds

2 baths

1,489 sq ft

House

2 beds