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

2399 NW 53RD AVENUE RD, OCALA, FL, 34482

Community: Ocala Palms

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

Questions? Call us: (689) 407-5757

On Top of the World

8723 SW 93RD LN C, OCALA, FL, 34481, Ocala, FL 34481

$204,402

2 beds

2 baths

1,531 sq ft

Villa

8723 SW 93RD LN C, OCALA, FL, 34481

Community: On Top of the World

Lake Jovita Golf and Country Club

13429 TRAILING MOSS DR, DADE CITY, FL, 3..., Dade City, FL 33525

$865,000

4 beds

3 baths

2,665 sq ft

House

13429 TRAILING MOSS DR, DADE CITY, FL, 3...

Community: Lake Jovita Golf and Country Club

Valencia Lakes

16209 AMETHYST KEY DR, WIMAUMA, FL, 3359..., Wimauma, FL 33598

$289,950

2 beds

2 baths

1,524 sq ft

Villa

16209 AMETHYST KEY DR, WIMAUMA, FL, 3359...

Community: Valencia Lakes

Stone Creek

17887 SW 72ND STREET RD, DUNNELLON, FL, ..., Dunnellon, FL 34432

$594,900

4 beds

3 baths

2,149 sq ft

House

17887 SW 72ND STREET RD, DUNNELLON, FL, ...

Community: Stone Creek

Stone Creek

17781 SW 72ND STREET RD, DUNNELLON, FL, ..., Dunnellon, FL 34432

$849,900

5 beds

4 baths

3,076 sq ft

House

17781 SW 72ND STREET RD, DUNNELLON, FL, ...

Community: Stone Creek

Legacy of Leesburg

27121 GREENFLY ORCHID LN, LEESBURG, FL, ..., Leesburg, FL 34748

$290,000

3 beds

2 baths

1,478 sq ft

House

27121 GREENFLY ORCHID LN, LEESBURG, FL, ...

Community: Legacy of Leesburg

Spruce Creek Country Club

13860 SE 97TH AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$339,000

2 beds

2 baths

1,654 sq ft

House

13860 SE 97TH AVE, SUMMERFIELD, FL, 3449...

Community: Spruce Creek Country Club

Solivita

448 GRAND CANAL DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$265,000

2 beds

2 baths

1,504 sq ft

House

448 GRAND CANAL DR, KISSIMMEE, FL, 34759

Community: Solivita

Venetian Bay

2814 S ASCIANO CT, NEW SMYRNA BEACH, FL,..., New Smyrna Beach, FL 32168

$779,900

3 beds

3 baths

2,300 sq ft

House

2814 S ASCIANO CT, NEW SMYRNA BEACH, FL,...

Community: Venetian Bay

Lakeside Landings

10363 ADDISON SHORE WAY, OXFORD, FL, 344..., Oxford, FL 34484

$345,000

3 beds

2 baths

1,653 sq ft

House

10363 ADDISON SHORE WAY, OXFORD, FL, 344...

Community: Lakeside Landings

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

Questions? Call us: (689) 407-5757

Lakeside Landings

10021 KETCH KAY LN, OXFORD, FL, 34484, Oxford, FL 34484

$462,900

4 beds

4 baths

2,932 sq ft

House

10021 KETCH KAY LN, OXFORD, FL, 34484

Community: Lakeside Landings

Venetian Bay

3606 MARIBELLA DR, NEW SMYRNA BEACH, FL,..., New Smyrna Beach, FL 32168

$769,900

3 beds

3 baths

2,460 sq ft

House

3606 MARIBELLA DR, NEW SMYRNA BEACH, FL,...

Community: Venetian Bay

Venetian Bay

3608 ROMEA CIR, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168

$329,900

3 beds

3 baths

2,036 sq ft

Townhouse

3608 ROMEA CIR, NEW SMYRNA BEACH, FL, 32...

Community: Venetian Bay

The Villages®

$589,000

2 beds

2 baths

1,522 sq ft

House

1302 LOPEZ LN, THE VILLAGES, FL, 32159

Community: The Villages®

Venetian Bay

3368 TUSCANO AVE, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168

$349,000

3 beds

2 baths

1,848 sq ft

House

3368 TUSCANO AVE, NEW SMYRNA BEACH, FL, ...

Community: Venetian Bay

Harbor Hills Country Club

6027 SPINNAKER LOOP, LADY LAKE, FL, 3215..., Lady Lake, FL 32159

$399,000

3 beds

2 baths

1,950 sq ft

House

6027 SPINNAKER LOOP, LADY LAKE, FL, 3215...

Community: Harbor Hills Country Club

Southshore Bay

17245 STAR BANKS ST, WIMAUMA, FL, 33598, Wimauma, FL 33598

$425,000

3 beds

3 baths

2,128 sq ft

House

17245 STAR BANKS ST, WIMAUMA, FL, 33598

Community: Southshore Bay

Solivita

123 GULF DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$218,000

2 beds

2 baths

1,317 sq ft

Halfplex

123 GULF DR, KISSIMMEE, FL, 34759

Community: Solivita

Royal Palm

1481 ARECA PALM DR, PORT ORANGE, FL, 321..., Port Orange, FL 32128

$449,900

4 beds

2 baths

2,229 sq ft

House

1481 ARECA PALM DR, PORT ORANGE, FL, 321...

Community: Royal Palm

Del Webb Oasis

11972 BRACCO ST, WINTER GARDEN, FL, 3478..., Winter Garden, FL 34787

$497,000

3 beds

3 baths

1,788 sq ft

House

11972 BRACCO ST, WINTER GARDEN, FL, 3478...

Community: Del Webb Oasis

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

Questions? Call us: (689) 407-5757

The Villages®

$275,000

3 beds

2 baths

1,392 sq ft

House

9514 SE 168TH MAPLESONG LN, THE VILLAGES...

Community: The Villages®

Plantation at Leesburg

4801 SUMMERBRIDGE CIR, LEESBURG, FL, 347..., Leesburg, FL 34748

$360,000

3 beds

3 baths

3,267 sq ft

House

4801 SUMMERBRIDGE CIR, LEESBURG, FL, 347...

Community: Plantation at Leesburg

Cresswind at Victoria Gardens

600 GARDEN CLUB DR, DELAND, FL, 32724, Deland, FL 32724

$599,000

4 beds

3 baths

2,569 sq ft

House

600 GARDEN CLUB DR, DELAND, FL, 32724

Community: Cresswind at Victoria Gardens

The Villages®

$249,900

2 beds

1 baths

1,067 sq ft

Villa

3010 FRITILLARY TER, THE VILLAGES, FL, 3...

Community: The Villages®

Venetian Bay

3615 MARISOL CT, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168

$549,900

3 beds

2 baths

1,764 sq ft

House

3615 MARISOL CT, NEW SMYRNA BEACH, FL, 3...

Community: Venetian Bay

Plantation at Leesburg

4649 BELLE GRV, LEESBURG, FL, 34748, Leesburg, FL 34748

$213,000

2 beds

2 baths

1,363 sq ft

House

4649 BELLE GRV, LEESBURG, FL, 34748

Community: Plantation at Leesburg

The Villages®

$349,500

2 beds

2 baths

1,132 sq ft

House

1497 ALEXANDRIA PL, THE VILLAGES, FL, 32...

Community: The Villages®

The Villages®

$699,000

3 beds

2 baths

2,522 sq ft

House

17274 SE 85TH WILLOWICK CIR, THE VILLAGE...

Community: The Villages®

The Villages®

1707 E SCHWARTZ BLVD, LADY LAKE, FL, 321..., Lady Lake, FL 32159

$205,000

2 beds

2 baths

1,040 sq ft

House

1707 E SCHWARTZ BLVD, LADY LAKE, FL, 321...

Community: The Villages®

Valencia Lakes

5103 SHADY STONE PL, WIMAUMA, FL, 33598, Wimauma, FL 33598

$495,000

3 beds

2 baths

2,001 sq ft

House

5103 SHADY STONE PL, WIMAUMA, FL, 33598

House

333 CARYOTA CT, NEW SMYRNA BEACH, FL, 32...

Community: Venetian 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.

Want more information about active adult communities around Winter Garden?

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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

3 beds

2 baths

1,292 sq ft

Villa

3 beds

2 baths

1,779 sq ft

House

3 beds

2 baths

1,392 sq ft

House

2 beds

2 baths

1,708 sq ft

Halfplex

3 beds

2 baths

1,739 sq ft

House

2 beds

2 baths

1,531 sq ft

Villa

4 beds

3 baths

2,665 sq ft

House

2 beds

2 baths

1,524 sq ft

Villa

4 beds

3 baths

2,149 sq ft

House

5 beds

4 baths

3,076 sq ft

House

3 beds

2 baths

1,478 sq ft

House

2 beds

2 baths

1,654 sq ft

House

2 beds

2 baths

1,504 sq ft

House

3 beds

3 baths

2,300 sq ft

House

3 beds

2 baths

1,653 sq ft

House

4 beds

4 baths

2,932 sq ft

House

3 beds

3 baths

2,460 sq ft

House

3 beds

3 baths

2,036 sq ft

Townhouse

2 beds

2 baths

1,522 sq ft

House

3 beds