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

3,584 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

<$100k - $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

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)

Trilogy® Orlando

$300Ks - $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 - $900Ks

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

$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

1257 CORINTH GREENS DR # 1257, SUN CITY ...

Community: Sun City Center

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

Questions? Call us: (689) 407-5757

Tampa Bay Golf and Country Club

29636 TEE SHOT DR, SAN ANTONIO, FL, 3357..., San Antonio, FL 33576

$375,000

3 beds

2 baths

1,762 sq ft

House

29636 TEE SHOT DR, SAN ANTONIO, FL, 3357...

Community: Tampa Bay Golf and Country Club

The Villages®

$380,000

4 beds

2 baths

2,001 sq ft

House

5638 CEDAR WAXWING DR, THE VILLAGES, FL,...

Community: The Villages®

Tampa Bay Golf and Country Club

10026 GAP WEDGE DR, SAN ANTONIO, FL, 335..., San Antonio, FL 33576

$329,000

3 beds

2 baths

1,731 sq ft

House

10026 GAP WEDGE DR, SAN ANTONIO, FL, 335...

Community: Tampa Bay Golf and Country Club

Del Webb Orlando

406 TORTOSA CT, DAVENPORT, FL, 33837, Davenport, FL 33837

$284,900

2 beds

2 baths

1,289 sq ft

House

406 TORTOSA CT, DAVENPORT, FL, 33837

Community: Del Webb Orlando

Valencia del Sol

5013 SEVILLA SHORES DR, WIMAUMA, FL, 335..., Wimauma, FL 33598

$574,900

3 beds

2 baths

2,074 sq ft

House

5013 SEVILLA SHORES DR, WIMAUMA, FL, 335...

Community: Valencia del Sol

Valencia del Sol

4914 SIENNA ISLES AVE, WIMAUMA, FL, 3359..., Wimauma, FL 33598

$384,900

3 beds

3 baths

2,040 sq ft

Villa

4914 SIENNA ISLES AVE, WIMAUMA, FL, 3359...

Community: Valencia del Sol

Venetian Bay

3110 ARECA AVE, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168

$365,000

3 beds

2 baths

1,650 sq ft

House

3110 ARECA AVE, NEW SMYRNA BEACH, FL, 32...

Community: Venetian Bay

The Villages®

$295,000

2 beds

2 baths

1,188 sq ft

House

3358 CASTLEGATE CT, THE VILLAGES, FL, 32...

Community: The Villages®

High Vista at Ridgewood Lakes

206 GOLF VISTA DR, DAVENPORT, FL, 33837, Davenport, FL 33837

$315,000

2 beds

2 baths

1,485 sq ft

House

206 GOLF VISTA DR, DAVENPORT, FL, 33837

Community: High Vista at Ridgewood Lakes

Harbor Hills Country Club

5312 MEADOW HILL LOOP, LADY LAKE, FL, 32..., Lady Lake, FL 32159

$589,000

4 beds

3 baths

2,532 sq ft

House

5312 MEADOW HILL LOOP, LADY LAKE, FL, 32...

Community: Harbor Hills Country Club

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

Questions? Call us: (689) 407-5757

Southshore Bay

16810 SCUBA CREST ST, WIMAUMA, FL, 33598, Wimauma, FL 33598

$470,000

2 beds

3 baths

2,239 sq ft

House

16810 SCUBA CREST ST, WIMAUMA, FL, 33598

Community: Southshore Bay

Sun City Center

$499,999

3 beds

2 baths

1,924 sq ft

House

1119 VILLEROY DR, SUN CITY CENTER, FL, 3...

Community: Sun City Center

Stone Creek

5307 SW 86TH COURT RD, OCALA, FL, 34481, Ocala, FL 34481

$341,700

2 beds

2 baths

1,405 sq ft

House

5307 SW 86TH COURT RD, OCALA, FL, 34481

Community: Stone Creek

Stone Creek

8335 SW 58TH LOOP, OCALA, FL, 34481, Ocala, FL 34481

$350,110

3 beds

2 baths

1,662 sq ft

House

8335 SW 58TH LOOP, OCALA, FL, 34481

Community: Stone Creek

Stone Creek

8435 SW 58TH LOOP, OCALA, FL, 34481, Ocala, FL 34481

$532,670

3 beds

3 baths

2,483 sq ft

House

8435 SW 58TH LOOP, OCALA, FL, 34481

Community: Stone Creek

Stone Creek

8163 SW 52ND LANE RD, OCALA, FL, 34481, Ocala, FL 34481

$374,130

3 beds

2 baths

1,662 sq ft

House

8163 SW 52ND LANE RD, OCALA, FL, 34481

Community: Stone Creek

Majestic Oaks Ocala

5461 SW 87TH PL, OCALA, FL, 34476, Ocala, FL 34476

$509,100

2 beds

3 baths

2,269 sq ft

House

5461 SW 87TH PL, OCALA, FL, 34476

Community: Majestic Oaks Ocala

The Villages®

$269,500

2 beds

2 baths

1,192 sq ft

House

521 SAN MARINO DR, THE VILLAGES, FL, 321...

Community: The Villages®

The Villages®

$309,500

3 beds

2 baths

1,392 sq ft

House

9621 SE 168TH MAPLESONG LN, THE VILLAGES...

Community: The Villages®

Venetian Bay

703 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168

$489,990

3 beds

3 baths

2,226 sq ft

House

703 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ...

Community: Venetian Bay

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

Questions? Call us: (689) 407-5757

Stone Creek

8206 SW 52ND LANE RD, OCALA, FL, 34481, Ocala, FL 34481

$351,630

3 beds

2 baths

1,662 sq ft

House

8206 SW 52ND LANE RD, OCALA, FL, 34481

Community: Stone Creek

Heritage Landings

2577 CANYON CREST DR, LAKELAND, FL, 3381..., Lakeland, FL 33811

$355,000

3 beds

2 baths

1,649 sq ft

House

Community: Stone Creek

Solivita

702 TORREY PINES WAY, POINCIANA, FL, 347..., Poinciana, FL 34759

$449,000

3 beds

3 baths

2,190 sq ft

House

702 TORREY PINES WAY, POINCIANA, FL, 347...

Community: Solivita

Sun City Center

$239,900

2 beds

2 baths

1,723 sq ft

Condo

2243 WORTHINGTON GREENS DR, SUN CITY CEN...

Villa

2294 TRAILWINDS TER, THE VILLAGES, FL, 3...

Community: The Villages®

Summer Trees

6037 WHISPERING TREES LN, PORT ORANGE, F..., Port Orange, FL 32128

$389,500

3 beds

2 baths

1,820 sq ft

House

6037 WHISPERING TREES LN, PORT ORANGE, F...

Community: Summer Trees

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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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3,584 homes near Winter Garden

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

106 communities near Winter Garden

3,584 homes near Winter Garden

2 beds

2 baths

1,442 sq ft

House

3 beds

2 baths

2,384 sq ft

House

3 beds

2 baths

2,562 sq ft

House

2 beds

2 baths

1,188 sq ft

House

2 beds

2 baths

1,435 sq ft

Condo

3 beds

2 baths

1,762 sq ft

House

4 beds

2 baths

2,001 sq ft

House

3 beds

2 baths

1,731 sq ft

House

2 beds

2 baths

1,289 sq ft

House

3 beds

2 baths

2,074 sq ft

House

3 beds

3 baths

2,040 sq ft

Villa

3 beds

2 baths

1,650 sq ft

House

2 beds

2 baths

1,188 sq ft

House

2 beds

2 baths

1,485 sq ft

House

4 beds

3 baths

2,532 sq ft

House

2 beds

3 baths

2,239 sq ft

House

3 beds

2 baths

1,924 sq ft

House

2 beds

2 baths

1,405 sq ft

House

3 beds

2 baths

1,662 sq ft

House

3 beds