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

3,573 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

1 2...3

Sun City Center

$299,900

2 beds

2 baths

1,206 sq ft

Condo

2082 SIFIELD GREENS WAY # 3, SUN CITY CE...

Community: Sun City Center

Sun City Center

$185,000

2 beds

2 baths

1,203 sq ft

Condo

2012 HEREFORD DR # 2012, SUN CITY CENTER...

3607 FAIRFIELD DR, CLERMONT, FL, 34711

Community: Kings Ridge

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

Questions? Call us: (689) 407-5757

Sun City Center

$334,990

2 beds

2 baths

1,493 sq ft

Condo

2311 NOTTINGHAM GREENS DR, SUN CITY CENT...

Community: Sun City Center

Del Webb Sunbridge

6403 SHIMMERING SHORES LN, SAINT CLOUD, ..., Saint Cloud, FL 34771

$512,000

3 beds

2 baths

1,677 sq ft

House

6403 SHIMMERING SHORES LN, SAINT CLOUD, ...

Community: Del Webb Sunbridge

Oak Run

10921 SW 82ND TER, OCALA, FL, 34481, Ocala, FL 34481

$199,788

2 beds

2 baths

1,368 sq ft

House

10921 SW 82ND TER, OCALA, FL, 34481

Community: Oak Run

The Villages®

$349,900

3 beds

2 baths

1,823 sq ft

House

501 HERRERA CT, THE VILLAGES, FL, 32159

Community: The Villages®

Sandpiper Golf & Country Club

6110 SANDPIPERS DR, LAKELAND, FL, 33809, Lakeland, FL 33809

$285,000

2 beds

2 baths

1,287 sq ft

House

6110 SANDPIPERS DR, LAKELAND, FL, 33809

Community: Sandpiper Golf & Country Club

Stone Creek

7807 SW 97TH CIR, OCALA, FL, 34481, Ocala, FL 34481

$332,223

2 beds

2 baths

1,795 sq ft

House

7807 SW 97TH CIR, OCALA, FL, 34481

Community: Stone Creek

Twin Lakes

2679 MIDSWEET AVE, SAINT CLOUD, FL, 3477..., Saint Cloud, FL 34772

$729,900

3 beds

3 baths

2,365 sq ft

House

2679 MIDSWEET AVE, SAINT CLOUD, FL, 3477...

Community: Twin Lakes

Southshore Bay

5325 KELPER HOOK CT, WIMAUMA, FL, 33598, Wimauma, FL 33598

$499,900

3 beds

3 baths

2,363 sq ft

House

5325 KELPER HOOK CT, WIMAUMA, FL, 33598

Community: Southshore Bay

Stone Creek

7259 SW 91ST CT, OCALA, FL, 34481, Ocala, FL 34481

$264,750

3 beds

2 baths

1,437 sq ft

House

7259 SW 91ST CT, OCALA, FL, 34481

Community: Stone Creek

Oak Run

8319 SW 108TH LOOP, OCALA, FL, 34481, Ocala, FL 34481

$269,000

3 beds

2 baths

2,041 sq ft

House

8319 SW 108TH LOOP, OCALA, FL, 34481

Community: Oak Run

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

Questions? Call us: (689) 407-5757

Oak Run

11091 SW 73RD CT, OCALA, FL, 34476, Ocala, FL 34476

$252,300

2 beds

2 baths

1,778 sq ft

House

11091 SW 73RD CT, OCALA, FL, 34476

Community: Oak Run

Latitude Margaritaville

464 TROPICS AVE, DAYTONA BEACH, FL, 3212..., Daytona Beach, FL 32124

$554,999

3 beds

2 baths

1,684 sq ft

House

464 TROPICS AVE, DAYTONA BEACH, FL, 3212...

Community: Latitude Margaritaville

Latitude Margaritaville

308 LOW TIDE LN, DAYTONA BEACH, FL, 3212..., Daytona Beach, FL 32124

$562,900

2 beds

3 baths

1,743 sq ft

House

308 LOW TIDE LN, DAYTONA BEACH, FL, 3212...

Community: Latitude Margaritaville

Ocala Palms

2398 NW 50TH AVE, OCALA, FL, 34482, Ocala, FL 34482

$319,500

3 beds

2 baths

2,246 sq ft

House

2398 NW 50TH AVE, OCALA, FL, 34482

Community: Ocala Palms

Ocala Palms

1920 NW 50TH CIR, OCALA, FL, 34482, Ocala, FL 34482

$204,900

2 beds

2 baths

1,062 sq ft

House

1920 NW 50TH CIR, OCALA, FL, 34482

Community: Ocala Palms

Stone Creek

6051 SW 93RD CIR, OCALA, FL, 34481, Ocala, FL 34481

$269,800

2 beds

2 baths

1,404 sq ft

House

6051 SW 93RD CIR, OCALA, FL, 34481

Community: Stone Creek

Ocala Preserve

5450 NW 46TH LANE RD, OCALA, FL, 34482, Ocala, FL 34482

$239,900

3 beds

2 baths

1,406 sq ft

House

5450 NW 46TH LANE RD, OCALA, FL, 34482

Community: Ocala Preserve

Stone Creek

6767 SW 91ST CIR, OCALA, FL, 34481, Ocala, FL 34481

$286,682

2 beds

2 baths

1,916 sq ft

Villa

6767 SW 91ST CIR, OCALA, FL, 34481

Community: Stone Creek

Stone Creek

9443 SW 71ST LOOP, OCALA, FL, 34481, Ocala, FL 34481

$498,888

3 beds

2 baths

2,413 sq ft

House

9443 SW 71ST LOOP, OCALA, FL, 34481

Community: Stone Creek

Sun City Center

$151,000

2 beds

2 baths

960 sq ft

Condo

302 CANTON CT UNIT 56, SUN CITY CENTER, ...

House

24502 PARLANGE CT, LEESBURG, FL, 34748

Community: Plantation at Leesburg

Highlands Ridge

4287 NORTH COURSE LN, AVON PARK, FL, 338..., Avon Park, FL 33825

$425,000

3 beds

2 baths

2,127 sq ft

House

4287 NORTH COURSE LN, AVON PARK, FL, 338...

Community: Highlands Ridge

Spruce Creek South

10185 SE 175TH LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$274,500

2 beds

3 baths

1,982 sq ft

House

10185 SE 175TH LN, SUMMERFIELD, FL, 3449...

Community: Spruce Creek South

Stone Creek

6816 SW 95TH CIR, OCALA, FL, 34481, Ocala, FL 34481

$474,999

2 beds

2 baths

1,969 sq ft

House

6816 SW 95TH CIR, OCALA, FL, 34481

Community: Stone Creek

Stone Creek

7335 SW 97TH TERRACE RD, OCALA, FL, 3448..., Ocala, FL 34481

$438,834

2 beds

2 baths

2,194 sq ft

House

7335 SW 97TH TERRACE RD, OCALA, FL, 3448...

Community: Stone Creek

Stone Creek

5564 SW 90TH AVE, OCALA, FL, 34481, Ocala, FL 34481

$610,000

3 beds

4 baths

2,990 sq ft

House

5564 SW 90TH AVE, OCALA, FL, 34481

Community: Stone Creek

Sun City Center

$210,000

2 beds

2 baths

1,857 sq ft

Condo

1508 INGRAM DR # 20, SUN CITY CENTER, FL...

Community: Sun City Center

Venetian Bay

3455 PEGASO AVE, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168

$509,000

3 beds

2 baths

2,174 sq ft

House

3455 PEGASO AVE, NEW SMYRNA BEACH, FL, 3...

House

6307 BERKSHIRE PASS, LEESBURG, FL, 34748

Community: Royal Highlands

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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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3,573 homes near Winter Garden

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

106 communities near Winter Garden

3,573 homes near Winter Garden

2 beds

2 baths

1,206 sq ft

Condo

2 beds

2 baths

1,203 sq ft

Condo

4 beds

2 baths

2,035 sq ft

House

3 beds

4 baths

2,782 sq ft

House

3 beds

2 baths

2,143 sq ft

House

2 beds

2 baths

1,493 sq ft

Condo

3 beds

2 baths

1,677 sq ft

House

2 beds

2 baths

1,368 sq ft

House

3 beds

2 baths

1,823 sq ft

House

2 beds

2 baths

1,287 sq ft

House

2 beds

2 baths

1,795 sq ft

House

3 beds

3 baths

2,365 sq ft

House

3 beds

3 baths

2,363 sq ft

House

3 beds

2 baths

1,437 sq ft

House

3 beds

2 baths

2,041 sq ft

House

2 beds

2 baths

1,778 sq ft

House

3 beds

2 baths

1,684 sq ft

House

2 beds

3 baths

1,743 sq ft

House

3 beds

2 baths

2,246 sq ft

House

2 beds