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

3595 EVERSHOLT ST, CLERMONT, FL, 34711

Community: Kings Ridge

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

Questions? Call us: (689) 407-5757

New Pennbrooke Fairways

642 GLEN OAKS DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$234,247

2 beds

2 baths

1,632 sq ft

House

642 GLEN OAKS DR, LEESBURG, FL, 34748

Community: Pennbrooke Fairways

Stonecrest

17485 SE 121ST CIR, SUMMERFIELD, FL, 344..., Summerfield, FL 34491

$369,900

3 beds

2 baths

1,990 sq ft

House

17485 SE 121ST CIR, SUMMERFIELD, FL, 344...

Community: Stonecrest

SummerGlen

16465 SW 14TH AVENUE RD, OCALA, FL, 3447..., Ocala, FL 34473

$296,900

3 beds

2 baths

1,810 sq ft

House

16465 SW 14TH AVENUE RD, OCALA, FL, 3447...

Community: SummerGlen

Plantation at Leesburg

24515 BOCAGE WAY, LEESBURG, FL, 34748, Leesburg, FL 34748

$355,000

3 beds

3 baths

2,204 sq ft

House

24515 BOCAGE WAY, LEESBURG, FL, 34748

Community: Plantation at Leesburg

New Valencia Lakes

16130 AMETHYST KEY DR, WIMAUMA, FL, 3359..., Wimauma, FL 33598

$299,900

2 beds

2 baths

1,496 sq ft

Villa

16130 AMETHYST KEY DR, WIMAUMA, FL, 3359...

Community: Valencia Lakes

Solivita

159 CASAVISTA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$445,000

2 beds

2 baths

1,771 sq ft

House

159 CASAVISTA DR, KISSIMMEE, FL, 34759

Community: Solivita

The Country Club of Mount Dora

8023 SAINT ANDREWS WAY, MOUNT DORA, FL, ..., Mount Dora, FL 32757

$324,900

2 beds

2 baths

1,494 sq ft

House

8023 SAINT ANDREWS WAY, MOUNT DORA, FL, ...

Community: The Country Club of Mount Dora

The Villages®

$279,900

2 beds

2 baths

1,156 sq ft

Villa

305 STARR LN, THE VILLAGES, FL, 32162

Community: The Villages®

Solivita

93 AUBURN DR, POINCIANA, FL, 34759, Poinciana, FL 34759

$329,000

3 beds

2 baths

2,141 sq ft

House

93 AUBURN DR, POINCIANA, FL, 34759

Community: Solivita

New Cresswind at Victoria Gardens

115 HERON POINT WAY, DELAND, FL, 32724, Deland, FL 32724

$369,000

3 beds

2 baths

1,773 sq ft

House

115 HERON POINT WAY, DELAND, FL, 32724

Community: Cresswind at Victoria Gardens

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

Questions? Call us: (689) 407-5757

Spruce Creek Country Club

12855 SE 92ND COURT RD, SUMMERFIELD, FL,..., Summerfield, FL 34491

$363,900

2 beds

2 baths

1,995 sq ft

House

12855 SE 92ND COURT RD, SUMMERFIELD, FL,...

Community: Spruce Creek Country Club

Ocala Palms

5366 NW 21ST LOOP, OCALA, FL, 34482, Ocala, FL 34482

$285,000

2 beds

92 baths

1,569 sq ft

House

5366 NW 21ST LOOP, OCALA, FL, 34482

Community: Ocala Palms

The Villages®

$700,000

3 beds

2 baths

2,320 sq ft

House

2082 VISION CT, THE VILLAGES, FL, 32163

Community: The Villages®

Arlington Ridge

26715 MANASSAS DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$500,000

3 beds

2 baths

2,449 sq ft

House

26715 MANASSAS DR, LEESBURG, FL, 34748

Community: Arlington Ridge

The Villages®

1765 W SCHWARTZ BLVD, LADY LAKE, FL, 321..., Lady Lake, FL 32159

$149,900

2 beds

2 baths

1,309 sq ft

Manufactured Home

1765 W SCHWARTZ BLVD, LADY LAKE, FL, 321...

Community: The Villages®

The Villages®

$438,800

3 beds

2 baths

1,667 sq ft

House

537 THISTLEDOWN WAY, THE VILLAGES, FL, 3...

Community: The Villages®

The Villages®

$399,000

3 beds

2 baths

1,488 sq ft

House

2212 YEAMANS PL, THE VILLAGES, FL, 32162

6070 SW 99TH PL, OCALA, FL, 34476

Community: Cherrywood

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

Questions? Call us: (689) 407-5757

Del Webb Sunbridge

6320 TRAILBLAZE BND, SAINT CLOUD, FL, 34..., Saint Cloud, FL 34771

$719,000

4 beds

3 baths

2,249 sq ft

House

6320 TRAILBLAZE BND, SAINT CLOUD, FL, 34...

Community: Del Webb Sunbridge

Ocala Palms

2093 NW 50TH CIR, OCALA, FL, 34482, Ocala, FL 34482

$249,900

2 beds

2 baths

1,270 sq ft

House

2093 NW 50TH CIR, OCALA, FL, 34482

Community: Ocala Palms

Spruce Creek South

9948 SE 175TH PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491

$279,900

2 beds

2 baths

1,878 sq ft

House

9948 SE 175TH PL, SUMMERFIELD, FL, 34491

Community: Spruce Creek South

The Villages®

$350,000

2 beds

2 baths

1,499 sq ft

Villa

1482 AZTECA LOOP, THE VILLAGES, FL, 3216...

Community: The Villages®

Sun City Center

$289,990

3 beds

2 baths

1,344 sq ft

House

1516 ARROWHEAD DR, SUN CITY CENTER, FL, ...

Community: Sun City Center

The Villages®

$534,000

3 beds

2 baths

1,927 sq ft

House

1266 JAMES ISLAND ST, THE VILLAGES, FL, ...

Community: The Villages®

Highland Fairways

2324 SEA ISLAND CIR, LAKELAND, FL, 33810, Lakeland, FL 33810

$227,000

2 beds

2 baths

1,355 sq ft

House

2324 SEA ISLAND CIR, LAKELAND, FL, 33810

Community: Highland Fairways

Kings Ridge

2310 GRASMERE CIR, CLERMONT, FL, 34711, Clermont, FL 34711

$325,000

2 beds

2 baths

1,677 sq ft

House

2310 GRASMERE CIR, CLERMONT, FL, 34711

Community: Kings Ridge

On Top of the World

8552 SW 92ND LN C, OCALA, FL, 34481, Ocala, FL 34481

$119,900

2 beds

2 baths

1,369 sq ft

Villa

8552 SW 92ND LN C, OCALA, FL, 34481

Community: On Top of the World

Lake James

$514,900

2 beds

2 baths

1,990 sq ft

House

7953 LAKE JAMES BLVD, LAKELAND, FL, 3381...

Community: Lake James

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

Questions? Call us: (689) 407-5757

On Top of the World

10082 SW 82ND PLACE RD, OCALA, FL, 34481, Ocala, FL 34481

$679,900

3 beds

3 baths

2,907 sq ft

House

10082 SW 82ND PLACE RD, OCALA, FL, 34481

Community: On Top of the World

The Villages®

$317,000

2 beds

2 baths

1,188 sq ft

Villa

2372 TRAVIS PL, THE VILLAGES, FL, 32162

Community: The Villages®

Twin Lakes

2772 SOUTHLAND ST, SAINT CLOUD, FL, 3477..., Saint Cloud, FL 34772

$549,900

3 beds

2 baths

1,863 sq ft

House

2772 SOUTHLAND ST, SAINT CLOUD, FL, 3477...

Community: Twin Lakes

Valencia del Sol

4920 SEVILLA SHORES DR, WIMAUMA, FL, 335..., Wimauma, FL 33598

$584,991

3 beds

3 baths

2,252 sq ft

House

4920 SEVILLA SHORES DR, WIMAUMA, FL, 335...

Community: Valencia del Sol

Southshore Bay

17576 HOLLY WELL AVE, WIMAUMA, FL, 33598, Wimauma, FL 33598

$344,900

2 beds

3 baths

1,747 sq ft

Townhouse

17576 HOLLY WELL AVE, WIMAUMA, FL, 33598

Community: Southshore Bay

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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.

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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

3 beds

2 baths

1,753 sq ft

Condo

3 beds

2 baths

1,462 sq ft

House

3 beds

2 baths

1,817 sq ft

House

2 beds

2 baths

1,350 sq ft

House

2 beds

2 baths

1,498 sq ft

House

2 beds

2 baths

1,632 sq ft

House

3 beds

2 baths

1,990 sq ft

House

3 beds

2 baths

1,810 sq ft

House

3 beds

3 baths

2,204 sq ft

House

2 beds

2 baths

1,496 sq ft

Villa

2 beds

2 baths

1,771 sq ft

House

2 beds

2 baths

1,494 sq ft

House

2 beds

2 baths

1,156 sq ft

Villa

3 beds

2 baths

2,141 sq ft

House

3 beds

2 baths

1,773 sq ft

House

2 beds

2 baths

1,995 sq ft

House

2 beds

92 baths

1,569 sq ft

House

3 beds

2 baths

2,320 sq ft

House

3 beds

2 baths

2,449 sq ft

House

2 beds