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

109 communities 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®

$100Ks - $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

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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

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 (2 reviews)

Plantation at Leesburg

$100Ks - $500Ks

Plantation at Leesburg, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1987 - 2008 | 2,820 homes

Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.

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 - $800Ks

Twin Lakes, St. Cloud, FL

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

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

Questions? Call us: (689) 407-5757

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+ rental communities in Winter Garden? 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

5 rating (8 reviews)

Royal Highlands

$200Ks - $500Ks

Royal Highlands, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 homes

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Questions? Call us: (689) 407-5757

3.8 rating (6 reviews)

Trilogy® Orlando

$200Ks - $600Ks

Trilogy® Orlando, Groveland, FL

Resale Only | 55+ age-restricted | Built 2005 - 2022 | 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

$400Ks - $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+ rental 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 - $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

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

Questions? Call us: (689) 407-5757

5 rating (5 reviews)

SummerGlen

$100Ks - $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+ rental 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

4.4 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

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

Questions? Call us: (689) 407-5757

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

149 BLUE HERON DR C, DAYTONA BEACH, FL, ...

Community: Pelican Bay Daytona Beach

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House

2403 ST GEORGE AVE, THE VILLAGES, FL, 32...

Community: The Villages®

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Questions? Call us: (689) 407-5757

The Villages®

$749,900

4 beds

3 baths

2,248 sq ft

House

3031 HICKS PL, THE VILLAGES, FL, 32163

Community: The Villages®

Valencia Lakes

16227 CAPE CORAL DR, WIMAUMA, FL, 33598, Wimauma, FL 33598

$449,500

4 beds

3 baths

2,419 sq ft

House

16227 CAPE CORAL DR, WIMAUMA, FL, 33598

Community: Valencia Lakes

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

2756 GRANDBURY GROVE RD, LAKELAND, FL, 3...

Community: Heritage Landings

Lakes at Laurel Highlands

$330,000

4 beds

2 baths

1,867 sq ft

House

2756 GRANDBURY GROVE RD, LAKELAND, FL, 3...

Community: Lakes at Laurel Highlands

Sun City Center

$350,000

3 beds

2 baths

1,860 sq ft

Condo

1324 EMERALD DUNES DR, SUN CITY CENTER, ...

Community: Sun City Center

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

Questions? Call us: (689) 407-5757

Lake Jovita Golf and Country Club

34303 SAHALEE LOOP, DADE CITY, FL, 33525, Dade City, FL 33525

$675,000

4 beds

3 baths

2,931 sq ft

House

34303 SAHALEE LOOP, DADE CITY, FL, 33525

Community: Lake Jovita Golf and Country Club

New Southshore Bay

17578 HOLLY WELL AVE, WIMAUMA, FL, 33598, Wimauma, FL 33598

$299,900

2 beds

2 baths

1,406 sq ft

Villa

17578 HOLLY WELL AVE, WIMAUMA, FL, 33598

Community: Southshore Bay

The Villages®

$421,000

3 beds

2 baths

1,918 sq ft

House

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

Community: The Villages®

The Villages®

$900,000

3 beds

2 baths

2,070 sq ft

House

3091 YODER DR, THE VILLAGES, FL, 32163

House

5103 SHADY STONE PL, WIMAUMA, FL, 33598

Community: Valencia Lakes

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

Questions? Call us: (689) 407-5757

New Venetian Bay

2967 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168

$358,500

3 beds

3 baths

1,672 sq ft

House

2967 MELETO BLVD, NEW SMYRNA BEACH, FL, ...

Community: Venetian Bay

Liberty Village

7867 SW 74TH LOOP, OCALA, FL, 34481, Ocala, FL 34481

$299,900

3 beds

2 baths

1,755 sq ft

House

7867 SW 74TH LOOP, OCALA, FL, 34481

Community: Liberty Village

On Top of the World

9846 SW 106TH CT, OCALA, FL, 34481, Ocala, FL 34481

$489,900

2 beds

3 baths

2,476 sq ft

House

9846 SW 106TH CT, OCALA, FL, 34481

Community: On Top of the World

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

The Villages®

$325,000

2 beds

2 baths

1,248 sq ft

House

2109 SUAREZ CT, THE VILLAGES, FL, 32159

House

15705 SW 16TH TER, OCALA, FL, 34473

Community: SummerGlen

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

Questions? Call us: (689) 407-5757

Summer Trees

109 CROOKED PINE RD, PORT ORANGE, FL, 32..., Port Orange, FL 32128

$273,827

2 beds

2 baths

1,106 sq ft

House

109 CROOKED PINE RD, PORT ORANGE, FL, 32...

Community: Summer Trees

Pelican Bay Daytona Beach

105 MARBLED GODWIT CT, DAYTONA BEACH, FL..., Daytona Beach, FL 32119

$395,000

3 beds

2 baths

2,568 sq ft

House

105 MARBLED GODWIT CT, DAYTONA BEACH, FL...

Community: Pelican Bay Daytona Beach

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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109 communities

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

109 communities near Winter Garden

3,495 homes near Winter Garden

3 beds

2 baths

2,031 sq ft

House

3 beds

2 baths

1,450 sq ft

House

2 beds

2 baths

1,515 sq ft

House

2 beds

2 baths

1,368 sq ft

Halfplex

2 beds

2 baths

1,192 sq ft

Condo

2 beds

2 baths

1,556 sq ft

Villa

2 beds

2 baths

1,156 sq ft

Villa

2 beds

2 baths

1,356 sq ft

Villa

3 beds

2 baths

2,057 sq ft

House

2 beds

2 baths

1,156 sq ft

Villa

3 beds

2 baths

1,888 sq ft

House

3 beds

2 baths

2,121 sq ft

House

3 beds

2 baths

1,392 sq ft

House

4 beds

3 baths

2,248 sq ft

House

4 beds

3 baths

2,419 sq ft

House

2 beds

2 baths

1,204 sq ft

House

2 beds

2 baths

1,324 sq ft

Manufactured Home

3 beds

2 baths

1,701 sq ft

House

4 beds

2 baths

1,867 sq ft

House

4 beds