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

113 communities near Winter Garden

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4 rating (17 reviews)

The Villages®

$100ks - $1Ms

The Villages®, The Villages, FL

New and Resale | 55+ age-restricted | Built 1978 - present | 70,000 homes

3.8 rating (14 reviews)

Sun City Center

$100ks - $800ks

Sun City Center, Sun City Center, FL

Resale Only | 55+ age-restricted | Built 1961 - 2018 | 9,500 homes

4 rating (56 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

4.2 rating (10 reviews)

Stone Creek

$200ks - $500ks

Stone Creek, Ocala, FL

New and Resale | 55+ age-restricted | Built 2006 - present | 3,800 homes

4.7 rating (18 reviews)

Solivita

$300ks - $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

4.5 rating (11 reviews)

Spruce Creek Country Club

$100ks - $400ks

Spruce Creek Country Club, Summerfield, FL

Resale Only | 55+ age-restricted | Built 1996 - 2007 | 3,250 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

5 rating (2 reviews)

Plantation at Leesburg

$100ks - $300ks

Plantation at Leesburg, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1987 - 2008 | 2,820 homes

Venetian Bay

$300ks - $1Ms

Venetian Bay, New Smyrna Beach, FL

New and Resale | Age-targeted | Built 2004 - present | 1,561 homes

4.6 rating (5 reviews)

Ocala Preserve

$100ks - $500ks

Ocala Preserve, Ocala, FL

New and Resale | 55+ age-restricted | Built 2014 - present | 1,800 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.

3.6 rating (48 reviews)

Latitude Margaritaville

$300ks - $800ks

Latitude Margaritaville, Daytona Beach, FL

Resale Only | 55+ age-restricted | Built 2017 - 2025 | 3,900 homes

5 rating (1 reviews)

Ocala Palms

$200ks - $300ks

Ocala Palms, Ocala, FL

Resale Only | 55+ age-restricted | Built 1994 - 1997 | 1,076 homes

5 rating (3 reviews)

Stonecrest

$200ks - $500ks

Stonecrest, Summerfield, FL

Resale Only | 55+ age-restricted | Built 1990 - 2024 | 2,224 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

3.8 rating (6 reviews)

Trilogy® Orlando

$200ks - $500ks

Trilogy® Orlando, Groveland, FL

Resale Only | 55+ age-restricted | Built 2005 - 2022 | 1,500 homes

2.8 rating (6 reviews)

Arlington Ridge

$200ks - $500ks

Arlington Ridge, Leesburg, FL

New and Resale | 55+ age-restricted | Built 2005 - present | 629 homes

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

Questions? Call us: (689) 407-5757

5 rating (3 reviews)

Twin Lakes

$200ks - $600ks

Twin Lakes, St. Cloud, FL

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

3.8 rating (4 reviews)

Spruce Creek South

$100ks - $200ks

Spruce Creek South, Summerfield, FL

Resale Only | 55+ age-restricted | Built 1989 - 1995 | 1,650 homes

4 rating (7 reviews)

Tampa Bay Golf and Countr...

$200ks - $500ks

Tampa Bay Golf and Countr..., San Antonio, FL

Resale Only | 55+ age-restricted | Built 1994 - 2015 | 1,336 homes

5 rating (8 reviews)

Royal Highlands

$200ks - $400ks

Royal Highlands, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 homes

Southshore Bay

$200ks - $500ks

Southshore Bay, Wimauma, FL

New and Resale | 55+ age-restricted | Built 2017 - present | 655 homes

5 rating (5 reviews)

SummerGlen

$200ks - $400ks

SummerGlen, Ocala, FL

Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,024 homes

5 rating (7 reviews)

Kings Ridge

$200ks - $400ks

Kings Ridge, Clermont, FL

Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 homes

4.7 rating (11 reviews)

Valencia Lakes

$200ks - $700ks

Valencia Lakes, Wimauma, FL

Resale Only | 55+ age-restricted | Built 2005 - 2019 | 1,631 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

5 rating (1 reviews)

Del Webb Sunbridge

$400ks - $800ks

Del Webb Sunbridge, St. Cloud, FL

New and Resale | 55+ age-restricted | Built 2019 - present | 1,300 homes

4 rating (4 reviews)

Lakes of Mount Dora

$300ks - $800ks

Lakes of Mount Dora, Mount Dora, FL

New and Resale | 55+ age-restricted | Built 2006 - present | 950 homes

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

Questions? Call us: (689) 407-5757

Pelican Bay Daytona Beach

$100ks - $600ks

Pelican Bay Daytona Beach, Daytona Beach, FL

Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 homes

5 rating (1 reviews)

Cresswind at Victoria Gar...

$200ks - $600ks

Cresswind at Victoria Gar..., DeLand, FL

Resale Only | 55+ age-restricted | Built 2001 - 2022 | 1,070 homes

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

4 rating (2 reviews)

Harbor Hills Country Club

$300ks - $900ks

Harbor Hills Country Club, Lady Lake, FL

New and Resale | Age-targeted | Built 1989 - present | 940 homes

2.3 rating (6 reviews)

Cherrywood

$100ks - $800ks

Cherrywood, Ocala, FL

Resale Only | 55+ age-restricted | Built 1996 - 2003 | 700 homes

3.6 rating (5 reviews)

Heritage Hills

$200ks - $400ks

Heritage Hills, Clermont, FL

New and Resale | 55+ age-restricted | Built 2006 - present | 1,154 homes

Mirada

$300ks - $500ks

Mirada, San Antonio, FL

New and Resale | 55+ age-restricted | Built 2019 - present | 858 homes

Quail Meadow

$200ks - $400ks

Quail Meadow, Ocala, FL

Resale Only | 55+ age-restricted | Built 1988 - 2006 | 460 homes

1 rating (1 reviews)

Sullivan Ranch

$200ks - $500ks

Sullivan Ranch, Mount Dora, FL

Resale Only | 55+ age-restricted | Built 2005 - 2020 | 692 homes

3.8 rating (5 reviews)

Marion Landing

$100ks - $300ks

Marion Landing, Ocala, FL

Resale Only | 55+ age-restricted | Built 1980 - 2004 | 600 homes

Ridgehaven

$300ks - $600ks

Ridgehaven, Ormond Beach, FL

New Construction | 55+ age-restricted

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

Questions? Call us: (689) 407-5757

Summer Trees

$200ks - $400ks

Summer Trees, Port Orange, FL

Resale Only | 55+ age-restricted | Built 1976 - 2005 | 500 homes

Pine Run Estates

$100ks - $200ks

Pine Run Estates, Ocala, FL

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

2501 LONIGAN PL, SUN CITY CENTER, FL, 33...

Community: Sun City Center

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508 FOXGLOVE CIR B, SUN CITY CENTER, FL,...

House

2408 CARRIAGE HILL WAY, THE VILLAGES, FL...

Community: The Villages®

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

Questions? Call us: (689) 407-5757

New The Villages®

1000 KENOVA AVE, THE VILLAGES, FL, 32162, The Villages, FL 32162

$340,000

3 beds

2 baths

1,392 sq ft

House

1000 KENOVA AVE, THE VILLAGES, FL, 32162

Community: The Villages®

New The Villages®

2014 SANTO DOMINGO DR, THE VILLAGES, FL,..., The Villages, FL 32159

$335,000

3 beds

2 baths

1,392 sq ft

House

2014 SANTO DOMINGO DR, THE VILLAGES, FL,...

Community: The Villages®

New The Villages®

2013 SANTO DOMINGO DR, THE VILLAGES, FL,..., The Villages, FL 32159

$450,000

3 beds

2 baths

2,015 sq ft

House

2013 SANTO DOMINGO DR, THE VILLAGES, FL,...

Community: The Villages®

New Del Webb Minneola

1105 CANOPY VIEW WAY, MINNEOLA, FL, 3471..., Minneola, FL 34715

$558,990

2 beds

2 baths

1,686 sq ft

House

1105 CANOPY VIEW WAY, MINNEOLA, FL, 3471...

Community: Del Webb Minneola

New Lake Jovita Golf and Country Club

13327 CARNOUSTIE CIR, DADE CITY, FL, 335..., Dade City, FL 33525

$1,350,000

3 beds

4 baths

3,331 sq ft

House

13327 CARNOUSTIE CIR, DADE CITY, FL, 335...

Community: Lake Jovita Golf and Country Club

New The Villages®

2778 EDWARDS LN, THE VILLAGES, FL, 32162, The Villages, FL 32162

$259,900

2 beds

2 baths

1,100 sq ft

House

2778 EDWARDS LN, THE VILLAGES, FL, 32162

Community: The Villages®

New The Villages®

608 DELGADO AVE, THE VILLAGES, FL, 32159, The Villages, FL 32159

$279,000

2 beds

2 baths

1,094 sq ft

Villa

608 DELGADO AVE, THE VILLAGES, FL, 32159

Community: The Villages®

New Cresswind at Victoria Gardens

1122 GARDENSHIRE LN, DELAND, FL, 32724, Deland, FL 32724

$399,900

2 beds

2 baths

1,928 sq ft

House

1122 GARDENSHIRE LN, DELAND, FL, 32724

Community: Cresswind at Victoria Gardens

New Del Webb Minneola

1143 CROWNING RIDGE WAY, MINNEOLA, FL, 3..., Minneola, FL 34715

$454,300

2 beds

2 baths

1,655 sq ft

House

1143 CROWNING RIDGE WAY, MINNEOLA, FL, 3...

Community: Del Webb Minneola

New Latitude Margaritaville

270 CORAL REEF WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124

$469,900

2 beds

2 baths

1,509 sq ft

House

270 CORAL REEF WAY, DAYTONA BEACH, FL, 3...

Community: Latitude Margaritaville

New The Villages®

366 TROY LOOP, THE VILLAGES, FL, 32162, The Villages, FL 32162

$498,500

3 beds

2 baths

1,927 sq ft

House

366 TROY LOOP, THE VILLAGES, FL, 32162

Community: The Villages®

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

Questions? Call us: (689) 407-5757

New The Villages®

728 PRADO DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$249,000

2 beds

2 baths

1,144 sq ft

Manufactured Home

728 PRADO DR, LADY LAKE, FL, 32159

Community: The Villages®

New The Villages®

1671 OSPREY AVE, THE VILLAGES, FL, 32162, The Villages, FL 32162

$315,000

2 beds

2 baths

1,156 sq ft

Villa

1671 OSPREY AVE, THE VILLAGES, FL, 32162

Community: The Villages®

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?

Call us: (689) 407-5757

113 communities

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

113 communities near Winter Garden

3,499 homes near Winter Garden

3 beds

2 baths

1,527 sq ft

House

4 beds

2 baths

2,050 sq ft

House

4 beds

3 baths

2,271 sq ft

House

3 beds

2 baths

1,342 sq ft

House

2 beds

2 baths

1,394 sq ft

Condo

2 beds

2 baths

1,563 sq ft

House

3 beds

2 baths

2,372 sq ft

House

2 beds

2 baths

1,717 sq ft

House

3 beds

3 baths

1,954 sq ft

House

2 beds

2 baths

1,100 sq ft

House

2 beds

2 baths

1,471 sq ft

House

2 beds

2 baths

2,211 sq ft

House

3 beds

2 baths

1,959 sq ft

House

2 beds

2 baths

2,188 sq ft

House

2 beds

2 baths

1,272 sq ft

House

2 beds

2 baths

1,085 sq ft

Condo

2 beds

2 baths

1,194 sq ft

House

3 beds

2 baths

1,791 sq ft

Villa

2 beds

2 baths

1,871 sq ft

House

3 beds