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)

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? 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

$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

4.4 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

102 UNDERBRUSH TRL, PORT ORANGE, FL, 321...

House

777 VINEYARD WAY, POINCIANA, FL, 34759

10269 SW 63RD AVE, OCALA, FL, 34476

Community: Cherrywood

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

Questions? Call us: (689) 407-5757

Valencia Lakes

16308 GARNET GLEN PL, WIMAUMA, FL, 33598, Wimauma, FL 33598

$625,000

3 beds

4 baths

2,741 sq ft

House

16308 GARNET GLEN PL, WIMAUMA, FL, 33598

Community: Valencia Lakes

Summit Greens

2366 PRAIRIE DUNES, CLERMONT, FL, 34711, Clermont, FL 34711

$393,000

3 beds

2 baths

1,725 sq ft

House

2366 PRAIRIE DUNES, CLERMONT, FL, 34711

Community: Summit Greens

Southshore Bay

17322 HOLLY WELL AVE, WIMAUMA, FL, 33598, Wimauma, FL 33598

$255,000

2 beds

2 baths

1,406 sq ft

Villa

17322 HOLLY WELL AVE, WIMAUMA, FL, 33598

Community: Southshore Bay

Breakaway Trails

8 FOX CLIFF WAY, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$550,000

4 beds

3 baths

2,566 sq ft

House

8 FOX CLIFF WAY, ORMOND BEACH, FL, 32174

Community: Breakaway Trails

Solivita

804 SAN RAPHAEL ST, POINCIANA, FL, 34759, Poinciana, FL 34759

$469,000

3 beds

4 baths

2,782 sq ft

House

804 SAN RAPHAEL ST, POINCIANA, FL, 34759

Community: Solivita

The Villages®

$485,000

3 beds

2 baths

2,124 sq ft

House

3327 DALKEITH TER, THE VILLAGES, FL, 321...

Community: The Villages®

The Villages®

$538,900

3 beds

2 baths

1,927 sq ft

House

2120 WILLOW GROVE WAY, THE VILLAGES, FL,...

Community: The Villages®

Ocala Preserve

4342 NW 55TH CT, OCALA, FL, 34482, Ocala, FL 34482

$439,900

3 beds

3 baths

2,172 sq ft

House

4342 NW 55TH CT, OCALA, FL, 34482

Community: Ocala Preserve

On Top of the World

8522 SW 99TH CIR, OCALA, FL, 34481, Ocala, FL 34481

$492,000

3 beds

3 baths

2,907 sq ft

House

8522 SW 99TH CIR, OCALA, FL, 34481

Community: On Top of the World

Palm Cay

10141 SW 106TH CIR, OCALA, FL, 34481, Ocala, FL 34481

$387,000

2 beds

2 baths

2,142 sq ft

House

10141 SW 106TH CIR, OCALA, FL, 34481

Community: Palm Cay

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

Questions? Call us: (689) 407-5757

On Top of the World

8660 SW 94TH ST F, OCALA, FL, 34481, Ocala, FL 34481

$172,500

2 beds

2 baths

1,391 sq ft

Villa

8660 SW 94TH ST F, OCALA, FL, 34481

Community: On Top of the World

Palm Cay

10107 SW 106TH CIR, OCALA, FL, 34481, Ocala, FL 34481

$383,000

2 beds

2 baths

2,142 sq ft

House

10107 SW 106TH CIR, OCALA, FL, 34481

Community: Palm Cay

Highland Lakes

5609 ROSEWALL CIR, LEESBURG, FL, 34748, Leesburg, FL 34748

$385,000

3 beds

3 baths

2,251 sq ft

House

5609 ROSEWALL CIR, LEESBURG, FL, 34748

Community: Highland Lakes

On Top of the World

10276 SW 105TH CT, OCALA, FL, 34481, Ocala, FL 34481

$452,000

3 beds

3 baths

2,211 sq ft

House

10276 SW 105TH CT, OCALA, FL, 34481

Community: On Top of the World

On Top of the World

10308 SW 105TH CT, OCALA, FL, 34481, Ocala, FL 34481

$366,000

2 beds

2 baths

2,019 sq ft

House

10308 SW 105TH CT, OCALA, FL, 34481

Community: On Top of the World

On Top of the World

10292 SW 105TH CT, OCALA, FL, 34481, Ocala, FL 34481

$486,000

3 beds

3 baths

2,907 sq ft

House

10292 SW 105TH CT, OCALA, FL, 34481

Community: On Top of the World

On Top of the World

10324 SW 105TH CT, OCALA, FL, 34481, Ocala, FL 34481

$387,000

3 beds

3 baths

2,297 sq ft

House

10324 SW 105TH CT, OCALA, FL, 34481

Community: On Top of the World

On Top of the World

10340 SW 105TH CT, OCALA, FL, 34481, Ocala, FL 34481

$352,000

2 beds

2 baths

1,718 sq ft

House

10340 SW 105TH CT, OCALA, FL, 34481

Community: On Top of the World

On Top of the World

10372 SW 105TH CT, OCALA, FL, 34481, Ocala, FL 34481

$352,000

2 beds

2 baths

1,718 sq ft

House

10372 SW 105TH CT, OCALA, FL, 34481

Community: On Top of the World

Pine Run Estates

10405 SW 98TH TER, OCALA, FL, 34481, Ocala, FL 34481

$174,750

2 beds

2 baths

1,040 sq ft

House

10405 SW 98TH TER, OCALA, FL, 34481

Community: Pine Run Estates

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

Questions? Call us: (689) 407-5757

Del Webb Sunbridge

3135 VANGUARD CT, SAINT CLOUD, FL, 34771, Saint Cloud, FL 34771

$1,025,000

4 beds

4 baths

2,813 sq ft

House

3135 VANGUARD CT, SAINT CLOUD, FL, 34771

Community: Del Webb Sunbridge

On Top of the World

10420 SW 105TH CT, OCALA, FL, 34481, Ocala, FL 34481

$428,000

3 beds

3 baths

2,536 sq ft

House

10420 SW 105TH CT, OCALA, FL, 34481

Community: On Top of the World

Sun City Center

$289,500

2 beds

2 baths

1,516 sq ft

House

1004 YELLOWBIRD PL, SUN CITY CENTER, FL,...

Community: Sun City Center

On Top of the World

10389 SW 105TH CT, OCALA, FL, 34481, Ocala, FL 34481

$386,000

2 beds

2 baths

2,142 sq ft

House

10389 SW 105TH CT, OCALA, FL, 34481

Community: On Top of the World

Del Webb Sunbridge

6376 SHIMMERING SHORES LN, SAINT CLOUD, ..., Saint Cloud, FL 34771

$474,900

2 beds

2 baths

1,781 sq ft

House

6376 SHIMMERING SHORES LN, SAINT CLOUD, ...

Community: Del Webb Sunbridge

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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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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

3 beds

2 baths

2,606 sq ft

House

2 beds

2 baths

1,008 sq ft

House

2 beds

2 baths

1,918 sq ft

House

4 beds

3 baths

2,741 sq ft

House

2 beds

2 baths

1,370 sq ft

House

3 beds

2 baths

2,034 sq ft

House

2 beds

2 baths

1,496 sq ft

House

2 beds

2 baths

2,365 sq ft

House

2 beds

2 baths

2,325 sq ft

House

2 beds

2 baths

1,392 sq ft

House

4 beds

2 baths

1,871 sq ft

House

3 beds

2 baths

1,392 sq ft

House

2 beds

2 baths

1,226 sq ft

House

3 beds

3 baths

2,268 sq ft

House

2 beds

2 baths

1,489 sq ft

House

3 beds

4 baths

2,741 sq ft

House

3 beds

2 baths

1,725 sq ft

House

2 beds

2 baths

1,406 sq ft

Villa

4 beds

3 baths

2,566 sq ft

House

3 beds