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

3,648 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 - $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

$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 - $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 (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 - $700Ks

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 - $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

<$100k - $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 - $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

$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

$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

No reviews yet

Venetian Bay

$300Ks - $2Ms

Venetian Bay, New Smyrna Beach, FL

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

3.8 rating (6 reviews)

Trilogy® Orlando

$300Ks - $500Ks

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

$400Ks - $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 - $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 - $500Ks

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 | 1,024 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

$400Ks - $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

4.4 rating (16 reviews)

Del Webb Orlando

$300Ks - $400Ks

Del Webb Orlando, Davenport, FL

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

No reviews yet

Pine Run Estates

<$100k - $300Ks

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

11651 SW 77TH CIR, OCALA, FL, 34476

House

8954 SW 109TH LN, OCALA, FL, 34481

914 ATTITUDE AVE, DAYTONA BEACH, FL, 321...

Community: Latitude Margaritaville

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

Questions? Call us: (689) 407-5757

Latitude Margaritaville

638 GOOD LIFE WAY, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32124

$409,900

2 beds

2 baths

1,464 sq ft

House

638 GOOD LIFE WAY, DAYTONA BEACH, FL, 32...

Community: Latitude Margaritaville

Lakeside Landings

4976 SANDPIPER DR, OXFORD, FL, 34484, Oxford, FL 34484

$484,900

4 beds

2 baths

2,696 sq ft

House

4976 SANDPIPER DR, OXFORD, FL, 34484

Community: Lakeside Landings

On Top of the World

7777 SW 86TH TERRACE RD, OCALA, FL, 3448..., Ocala, FL 34481

$299,000

2 beds

2 baths

1,344 sq ft

House

7777 SW 86TH TERRACE RD, OCALA, FL, 3448...

Community: On Top of the World

Sun City Center

$269,000

2 beds

2 baths

1,493 sq ft

Villa

809 CHIPPER DR, SUN CITY CENTER, FL, 335...

Community: Sun City Center

Oak Run

10891 SW 90TH TER, OCALA, FL, 34481, Ocala, FL 34481

$221,500

3 beds

2 baths

1,620 sq ft

House

10891 SW 90TH TER, OCALA, FL, 34481

Community: Oak Run

On Top of the World

9775 SW 92ND ST, OCALA, FL, 34481, Ocala, FL 34481

$348,900

2 beds

2 baths

1,739 sq ft

House

9775 SW 92ND ST, OCALA, FL, 34481

Community: On Top of the World

Marion Landing

8481 SW 61ST TERRACE RD, OCALA, FL, 3447..., Ocala, FL 34476

$244,500

3 beds

2 baths

1,651 sq ft

House

8481 SW 61ST TERRACE RD, OCALA, FL, 3447...

Community: Marion Landing

Alhambra Villas Condominiums

183 N HILL AVE # 90, DELAND, FL, 32724, Deland, FL 32724

$188,000

2 beds

2 baths

979 sq ft

Condo

183 N HILL AVE # 90, DELAND, FL, 32724

Community: Alhambra Villas Condominiums

Encore at Fishhawk Ranch

13915 KINGFISHER GLEN DR, LITHIA, FL, 33..., Lithia, FL 33547

$445,000

2 beds

2 baths

1,769 sq ft

House

13915 KINGFISHER GLEN DR, LITHIA, FL, 33...

Community: Encore at Fishhawk Ranch

Venetian Bay

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

$459,990

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

Lake Jovita Golf and Country Club

13816 THOROUGHBRED DR, DADE CITY, FL, 33..., Dade City, FL 33525

$799,000

4 beds

3 baths

2,825 sq ft

House

13816 THOROUGHBRED DR, DADE CITY, FL, 33...

Community: Lake Jovita Golf and Country Club

Scottish Highlands

28 GORDON CT, LEESBURG, FL, 34788, Leesburg, FL 34788

$195,000

2 beds

2 baths

1,374 sq ft

House

28 GORDON CT, LEESBURG, FL, 34788

Community: Scottish Highlands

Oak Run

11696 SW 71ST CIR, OCALA, FL, 34476, Ocala, FL 34476

$189,999

2 beds

2 baths

1,218 sq ft

House

11696 SW 71ST CIR, OCALA, FL, 34476

Community: Oak Run

Venetian Bay

3054 ISLES WAY, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168

$575,000

3 beds

4 baths

1,847 sq ft

Townhouse

3054 ISLES WAY, NEW SMYRNA BEACH, FL, 32...

Community: Venetian Bay

Oak Run

11481 SW 82ND COURT RD, OCALA, FL, 34481, Ocala, FL 34481

$338,800

3 beds

3 baths

2,340 sq ft

House

11481 SW 82ND COURT RD, OCALA, FL, 34481

Community: Oak Run

Highlands Ridge

3215 E PEBBLE CREEK DR, AVON PARK, FL, 3..., Avon Park, FL 33825

$269,900

2 beds

2 baths

1,574 sq ft

House

3215 E PEBBLE CREEK DR, AVON PARK, FL, 3...

Community: Highlands Ridge

Spruce Creek Country Club

13089 SE 86TH CT, SUMMERFIELD, FL, 34491, Summerfield, FL 34491

$321,000

2 beds

2 baths

1,870 sq ft

House

13089 SE 86TH CT, SUMMERFIELD, FL, 34491

Community: Spruce Creek Country Club

Solivita

591 HIGHLANDS HAMMOCK DR, KISSIMMEE, FL,..., Kissimmee, FL 34759

$390,900

2 beds

2 baths

2,078 sq ft

House

591 HIGHLANDS HAMMOCK DR, KISSIMMEE, FL,...

Community: Solivita

The Villages®

$265,000

2 beds

2 baths

1,188 sq ft

Villa

2388 BRANCHVILLE TER, THE VILLAGES, FL, ...

Community: The Villages®

On Top of the World

9357 SW 82ND TER B, OCALA, FL, 34481, Ocala, FL 34481

$182,000

2 beds

2 baths

1,249 sq ft

Villa

9357 SW 82ND TER B, OCALA, FL, 34481

Community: On Top of the World

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

Questions? Call us: (689) 407-5757

Highlands Ridge

3509 E SAINT ANDREWS DR, AVON PARK, FL, ..., Avon Park, FL 33825

$269,900

3 beds

2 baths

1,845 sq ft

House

3509 E SAINT ANDREWS DR, AVON PARK, FL, ...

Community: Highlands Ridge

Highlands Ridge

4032 CARTER CREEK DR, AVON PARK, FL, 338..., Avon Park, FL 33825

$479,000

3 beds

3 baths

2,808 sq ft

House

4032 CARTER CREEK DR, AVON PARK, FL, 338...

Community: Highlands Ridge

Highlands Ridge

5056 BIRKDALE DR, AVON PARK, FL, 33825, Avon Park, FL 33825

$299,900

2 beds

2 baths

1,799 sq ft

Villa

5056 BIRKDALE DR, AVON PARK, FL, 33825

Community: Highlands Ridge

Sun City Center

$245,900

2 beds

2 baths

1,756 sq ft

Villa

810 BLUEWATER DR, SUN CITY CENTER, FL, 3...

Community: Sun City Center

Sun City Center

$225,000

2 beds

2 baths

1,200 sq ft

Condo

708 RUTGERS PL, SUN CITY CENTER, FL, 335...

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.

Want more information about active adult communities around Winter Garden?

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3,648 homes near Winter Garden

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

108 communities near Winter Garden

3,648 homes near Winter Garden

2 beds

2 baths

1,328 sq ft

House

2 beds

2 baths

1,379 sq ft

House

3 beds

2 baths

1,913 sq ft

House

3 beds

2 baths

2,066 sq ft

House

3 beds

2 baths

2,172 sq ft

House

2 beds

2 baths

1,900 sq ft

House

2 beds

2 baths

2,599 sq ft

House

2 beds

2 baths

1,374 sq ft

House

2 beds

2 baths

1,200 sq ft

House

2 beds

2 baths

1,466 sq ft

House

2 beds

2 baths

1,666 sq ft

House

2 beds

2 baths

1,726 sq ft

House

3 beds

2 baths

1,974 sq ft

House

3 beds

2 baths

1,516 sq ft

House

2 beds

2 baths

1,563 sq ft

House

2 beds

2 baths

1,464 sq ft

House

4 beds

2 baths

2,696 sq ft

House

2 beds

2 baths

1,344 sq ft

House

2 beds

2 baths

1,493 sq ft

Villa

3 beds