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

3,958 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 - $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

<$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

$200Ks - $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 - $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 - $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 - $600Ks

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 - $1Ms

Twin Lakes, St. Cloud, FL

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

No reviews yet

Pelican Bay Daytona Beach

<$100k - $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

$200Ks - $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 - $900Ks

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

$200Ks - $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)

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+ 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...

$100Ks - $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

$300Ks - $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 - $500Ks

SummerGlen, Ocala, FL

Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,029 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

$400Ks - $700Ks

Breakaway Trails, Ormond Beach, FL

New and Resale | Age-targeted | Built 1985 - present | 976 homes

4 rating (4 reviews)

Lakes of Mount Dora

$200Ks - $800Ks

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 - $800Ks

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

$100Ks - $300Ks

Highland Lakes, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes

4.3 rating (15 reviews)

Del Webb Orlando

$200Ks - $500Ks

Del Webb Orlando, Davenport, FL

Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes

No reviews yet

Pine Run Estates

$100Ks - $400Ks

Pine Run Estates, Ocala, FL

Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 homes

No reviews yet

Lake Jovita Golf and Coun...

$400Ks - $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 - $900Ks

Esplanade at Wiregrass Ra..., Wesley Chapel, FL

New and Resale | 55+ age-restricted | Built 2019 - present | 868 homes

2105 ESCOBAR AVE, THE VILLAGES, FL, 3215...

Community: The Villages®

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

Questions? Call us: (689) 407-5757

Plantation at Leesburg

25222 LAUREL VALLEY RD, LEESBURG, FL, 34..., Leesburg, FL 34748

$399,890

2 beds

3 baths

2,188 sq ft

House

25222 LAUREL VALLEY RD, LEESBURG, FL, 34...

Community: Plantation at Leesburg

The Villages®

$975,000

4 beds

2 baths

2,606 sq ft

House

631 INDEPENDENCE PATH, THE VILLAGES, FL,...

Community: The Villages®

Lake Ashton

4488 TURNBERRY LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859

$225,000

2 beds

2 baths

1,083 sq ft

House

4488 TURNBERRY LN, LAKE WALES, FL, 33859

Community: Lake Ashton

The Villages®

$485,000

3 beds

2 baths

1,956 sq ft

House

3136 VANDENBERG CT, THE VILLAGES, FL, 32...

Community: The Villages®

Sandpiper Golf & Country Club

6086 SWALLOW DR, LAKELAND, FL, 33809, Lakeland, FL 33809

$364,900

3 beds

2 baths

2,028 sq ft

House

6086 SWALLOW DR, LAKELAND, FL, 33809

Community: Sandpiper Golf & Country Club

Lake Ashton

5005 PEBBLE BEACH BLVD, WINTER HAVEN, FL..., Winter Haven, FL 33884

$449,000

3 beds

2 baths

1,892 sq ft

House

5005 PEBBLE BEACH BLVD, WINTER HAVEN, FL...

Community: Lake Ashton

Lake Jovita Golf and Country Club

13539 CARRYBACK DR, DADE CITY, FL, 33525, Dade City, FL 33525

$984,999

4 beds

4 baths

3,217 sq ft

House

13539 CARRYBACK DR, DADE CITY, FL, 33525

Community: Lake Jovita Golf and Country Club

The Villages®

$289,555

2 beds

2 baths

1,156 sq ft

Villa

1070 PINEWOOD PL, THE VILLAGES, FL, 3216...

Community: The Villages®

The Villages®

1541 DORAL CIR, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$229,750

2 beds

2 baths

1,040 sq ft

Manufactured Home

1541 DORAL CIR, LADY LAKE, FL, 32159

Community: The Villages®

The Villages®

$659,500

3 beds

2 baths

2,231 sq ft

House

1875 OXFORD LN, THE VILLAGES, FL, 32162

Villa

1750 KINGFISHER CT, THE VILLAGES, FL, 32...

Community: The Villages®

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

Questions? Call us: (689) 407-5757

Sun City Center

$269,900

2 beds

2 baths

1,624 sq ft

House

1830 E DEL WEBB BLVD, SUN CITY CENTER, F...

Community: Sun City Center

The Villages®

$525,000

3 beds

2 baths

2,030 sq ft

House

1751 ASHWOOD RUN, THE VILLAGES, FL, 3216...

Community: The Villages®

Venetian Bay

3250 TIGER PALM WAY, NEW SMYRNA BEACH, F..., New Smyrna Beach, FL 32168

$667,765

5 beds

5 baths

3,136 sq ft

House

3250 TIGER PALM WAY, NEW SMYRNA BEACH, F...

Community: Venetian Bay

The Villages®

$374,900

3 beds

2 baths

1,589 sq ft

House

3405 RABBIT RUN PATH, THE VILLAGES, FL, ...

Community: The Villages®

Stonecrest

11799 SE 173RD LANE RD, SUMMERFIELD, FL,..., Summerfield, FL 34491

$470,000

3 beds

2 baths

2,008 sq ft

House

11799 SE 173RD LANE RD, SUMMERFIELD, FL,...

Community: Stonecrest

The Villages®

1146 W BOONE CT, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$238,000

2 beds

2 baths

1,418 sq ft

Manufactured Home

1146 W BOONE CT, LADY LAKE, FL, 32159

Community: The Villages®

Plantation at Leesburg

25236 WATERBRIDGE CT, LEESBURG, FL, 3474..., Leesburg, FL 34748

$434,999

3 beds

3 baths

2,020 sq ft

House

25236 WATERBRIDGE CT, LEESBURG, FL, 3474...

Community: Plantation at Leesburg

The Villages®

$374,900

3 beds

2 baths

1,552 sq ft

House

2360 HOPESPRING LOOP, THE VILLAGES, FL, ...

Community: The Villages®

Spruce Creek North

11282 SW 62ND AVENUE RD, OCALA, FL, 3447..., Ocala, FL 34476

$189,900

2 beds

2 baths

1,008 sq ft

House

11282 SW 62ND AVENUE RD, OCALA, FL, 3447...

Community: Spruce Creek North

Venetian Bay

3194 TIGER PALM WAY, NEW SMYRNA BEACH, F..., New Smyrna Beach, FL 32168

$532,780

4 beds

4 baths

3,136 sq ft

House

3194 TIGER PALM WAY, NEW SMYRNA BEACH, F...

House

3198 TIGER PALM WAY, NEW SMYRNA BEACH, F...

Community: Venetian Bay

New Latitude Margaritaville

500 LANDSHARK BLVD, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124

$429,900

2 beds

2 baths

1,464 sq ft

House

500 LANDSHARK BLVD, DAYTONA BEACH, FL, 3...

Community: Latitude Margaritaville

Sun City Center

$339,999

2 beds

2 baths

1,528 sq ft

House

301 CALOOSA PALMS CT, SUN CITY CENTER, F...

Community: Sun City Center

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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.

How long do listings in 55+ communities in Winter Garden typically stay on the market, and what is the average price of homes for sale?

On average, listings in 55+ communities in Winter Garden stay on the market for around 143 days. The average price of homes for sale in these communities is approximately $502,460, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Del Webb Oasis average around $502,460.

Want more information about active adult communities around Winter Garden?

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3,958 homes near Winter Garden

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

106 communities near Winter Garden

3,958 homes near Winter Garden

2 beds

2 baths

1,401 sq ft

House

4 beds

2 baths

1,833 sq ft

House

3 beds

2 baths

2,120 sq ft

House

2 beds

2 baths

1,394 sq ft

House

2 beds

2 baths

1,121 sq ft

House

2 beds

3 baths

2,188 sq ft

House

4 beds

2 baths

2,606 sq ft

House

2 beds

2 baths

1,083 sq ft

House

3 beds

2 baths

1,956 sq ft

House

3 beds

2 baths

2,028 sq ft

House

3 beds

2 baths

1,892 sq ft

House

4 beds

4 baths

3,217 sq ft

House

2 beds

2 baths

1,156 sq ft

Villa

2 beds

2 baths

1,040 sq ft

Manufactured Home

3 beds

2 baths

2,231 sq ft

House

3 beds

2 baths

2,271 sq ft

House

2 beds

2 baths

1,727 sq ft

House

2 beds

2 baths

1,711 sq ft

House

3 beds

2 baths

1,968 sq ft

House

2 beds