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

3,537 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 - $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

$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 - $600Ks

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 - $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 - $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

$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 - $600Ks

Twin Lakes, St. Cloud, FL

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

Pelican Bay Daytona Beach

$100Ks - $400Ks

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 - $400Ks

Spruce Creek South, Summerfield, FL

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

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

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 - $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)

Del Webb Sunbridge

$300Ks - $1Ms

Del Webb Sunbridge, St. Cloud, FL

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

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 - $400Ks

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

Breakaway Trails

$400Ks - $800Ks

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

$100Ks - $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

Pine Run Estates

$100Ks - $300Ks

Pine Run Estates, Ocala, FL

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

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

Esplanade at Wiregrass Ra...

$400Ks - $1Ms

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

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

1069 SAWGRASS DR, WINTER HAVEN, FL, 3388...

Community: Lake Ashton

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

Questions? Call us: (689) 407-5757

Harbor Hills Country Club

5435 GROVE MNR, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$410,000

3 beds

2 baths

1,821 sq ft

House

5435 GROVE MNR, LADY LAKE, FL, 32159

Community: Harbor Hills Country Club

Esplanade at Wiregrass Ranch

4831 ROSATTI RD, WESLEY CHAPEL, FL, 3354..., Wesley Chapel, FL 33543

$675,000

3 beds

3 baths

2,296 sq ft

House

4831 ROSATTI RD, WESLEY CHAPEL, FL, 3354...

Community: Esplanade at Wiregrass Ranch

The Villages®

$314,000

2 beds

2 baths

1,257 sq ft

House

2866 JUDAH ST, THE VILLAGES, FL, 32163

Community: The Villages®

Spruce Creek Country Club

9588 SE 124TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491

$339,000

2 beds

2 baths

1,979 sq ft

House

9588 SE 124TH LOOP, SUMMERFIELD, FL, 344...

Community: Spruce Creek Country Club

Traditions at Lake Ruby

3365 RALEIGH DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884

$285,000

2 beds

2 baths

1,295 sq ft

House

3365 RALEIGH DR, WINTER HAVEN, FL, 33884

Community: Traditions at Lake Ruby

On Top of the World

9878 SW 97TH LN, OCALA, FL, 34481, Ocala, FL 34481

$330,000

2 beds

2 baths

1,911 sq ft

House

9878 SW 97TH LN, OCALA, FL, 34481

Community: On Top of the World

On Top of the World

8785 SW 91ST ST B, OCALA, FL, 34481, Ocala, FL 34481

$148,500

2 beds

2 baths

1,204 sq ft

Villa

8785 SW 91ST ST B, OCALA, FL, 34481

Community: On Top of the World

Trilogy® Orlando

537 NARROW VIEW LN, GROVELAND, FL, 34736, Groveland, FL 34736

$424,900

3 beds

2 baths

1,905 sq ft

House

537 NARROW VIEW LN, GROVELAND, FL, 34736

Community: Trilogy® Orlando

Solivita

543 VIA VITALE CT, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$439,000

2 beds

3 baths

2,235 sq ft

House

543 VIA VITALE CT, KISSIMMEE, FL, 34759

Community: Solivita

Sun City Center

$360,000

3 beds

2 baths

1,971 sq ft

House

627 FORT DUQUESNA DR, SUN CITY CENTER, F...

Community: Sun City Center

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

Questions? Call us: (689) 407-5757

The Villages®

$749,999

4 beds

3 baths

2,959 sq ft

House

1738 AUGUSTINE DR, THE VILLAGES, FL, 321...

Community: The Villages®

Sun City Center

$409,900

3 beds

3 baths

2,342 sq ft

House

2309 LYNDHURST DR, SUN CITY CENTER, FL, ...

Community: Sun City Center

Highlands Ridge

3003 OAKHILL DR, AVON PARK, FL, 33825, Avon Park, FL 33825

$314,900

3 beds

2 baths

1,836 sq ft

House

3003 OAKHILL DR, AVON PARK, FL, 33825

Community: Highlands Ridge

Palms at Serenoa

17418 BLAZING STAR CIR, CLERMONT, FL, 34..., Clermont, FL 34714

$415,000

3 beds

2 baths

1,621 sq ft

House

17418 BLAZING STAR CIR, CLERMONT, FL, 34...

Community: Palms at Serenoa

Latitude Margaritaville

856 MARGARITAVILLE AVE, DAYTONA BEACH, F..., Daytona Beach, FL 32124

$559,900

2 beds

2 baths

1,862 sq ft

House

856 MARGARITAVILLE AVE, DAYTONA BEACH, F...

Community: Latitude Margaritaville

Sun City Center

$184,990

2 beds

2 baths

1,516 sq ft

Condo

382 CLUB MANOR DR, SUN CITY CENTER, FL, ...

Community: Sun City Center

Solivita

525 GENOA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$449,000

3 beds

3 baths

2,325 sq ft

House

525 GENOA DR, KISSIMMEE, FL, 34759

Community: Solivita

Oak Run

11653 SW 72ND CIR, OCALA, FL, 34476, Ocala, FL 34476

$269,000

3 beds

2 baths

1,495 sq ft

House

11653 SW 72ND CIR, OCALA, FL, 34476

Community: Oak Run

Pelican Bay Daytona Beach

114 BLUE HERON DR D, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119

$180,000

2 beds

2 baths

1,242 sq ft

Condo

114 BLUE HERON DR D, DAYTONA BEACH, FL, ...

Community: Pelican Bay Daytona Beach

Summer Trees

129 DUSK MEADOW TRL, PORT ORANGE, FL, 32..., Port Orange, FL 32128

$289,900

2 beds

2 baths

1,414 sq ft

House

129 DUSK MEADOW TRL, PORT ORANGE, FL, 32...

House

10967 SW 81ST AVE, OCALA, FL, 34481

5659 SW 89TH PL, OCALA, FL, 34476

Community: Majestic Oaks Ocala

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

Questions? Call us: (689) 407-5757

Marco Polo Village

5024 SW 114TH STREET RD, OCALA, FL, 3447..., Ocala, FL 34476

$529,000

3 beds

3 baths

2,652 sq ft

House

5024 SW 114TH STREET RD, OCALA, FL, 3447...

Community: Marco Polo Village

Solivita

128 RIALTO RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$319,000

2 beds

2 baths

1,398 sq ft

House

128 RIALTO RD, KISSIMMEE, FL, 34759

Community: Solivita

The Villages®

$324,900

3 beds

2 baths

1,483 sq ft

House

2572 BERRINGTON LOOP, THE VILLAGES, FL, ...

Community: The Villages®

The Villages®

$339,900

3 beds

2 baths

1,398 sq ft

Villa

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

Community: The Villages®

Valencia Lakes

4938 SANDY BROOK CIR, WIMAUMA, FL, 33598, Wimauma, FL 33598

$309,000

2 beds

2 baths

1,486 sq ft

House

4938 SANDY BROOK CIR, WIMAUMA, FL, 33598

Community: Valencia Lakes

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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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3,537 homes near Winter Garden

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

109 communities near Winter Garden

3,537 homes near Winter Garden

2 beds

1 baths

1,344 sq ft

House

3 beds

2 baths

2,120 sq ft

House

3 beds

2 baths

2,032 sq ft

House

3 beds

2 baths

1,564 sq ft

House

2 beds

2 baths

1,688 sq ft

House

3 beds

2 baths

1,821 sq ft

House

3 beds

3 baths

2,296 sq ft

House

2 beds

2 baths

1,257 sq ft

House

2 beds

2 baths

1,979 sq ft

House

2 beds

2 baths

1,295 sq ft

House

2 beds

2 baths

1,911 sq ft

House

2 beds

2 baths

1,204 sq ft

Villa

3 beds

2 baths

1,905 sq ft

House

2 beds

3 baths

2,235 sq ft

House

3 beds

2 baths

1,971 sq ft

House

4 beds

3 baths

2,959 sq ft

House

3 beds

3 baths

2,342 sq ft

House

3 beds

2 baths

1,836 sq ft

House

3 beds

2 baths

1,621 sq ft

House

2 beds