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)

VillageWalk at Lake Nona

$300Ks - $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

<$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

$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

4.4 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

604 OJAI AVE, SUN CITY CENTER, FL, 33573

House

2739 MIDLAND TER, THE VILLAGES, FL, 3216...

Community: The Villages®

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

Questions? Call us: (689) 407-5757

The Villages®

$319,900

2 beds

2 baths

1,227 sq ft

Villa

6052 CHASE CT, THE VILLAGES, FL, 32163

Community: The Villages®

The Villages®

$635,000

3 beds

3 baths

2,033 sq ft

House

4234 MCCLOY AVE, THE VILLAGES, FL, 32163

Community: The Villages®

The Villages®

$449,900

3 beds

2 baths

1,404 sq ft

House

1771 WINTHROP TER, THE VILLAGES, FL, 321...

Community: The Villages®

The Villages®

$329,900

2 beds

2 baths

1,138 sq ft

Villa

1798 LONGWOOD CT, THE VILLAGES, FL, 3216...

Community: The Villages®

The Villages®

$355,900

2 beds

2 baths

1,206 sq ft

House

2085 IRONTON PL, THE VILLAGES, FL, 32163

Community: The Villages®

On Top of the World

9491 SW 98TH CT, OCALA, FL, 34481, Ocala, FL 34481

$299,000

2 beds

2 baths

1,737 sq ft

House

9491 SW 98TH CT, OCALA, FL, 34481

Community: On Top of the World

Ocala Preserve

4687 NW 35TH LANE RD, OCALA, FL, 34482, Ocala, FL 34482

$450,000

2 beds

2 baths

2,316 sq ft

House

4687 NW 35TH LANE RD, OCALA, FL, 34482

Community: Ocala Preserve

Spruce Creek South

9885 SE 177TH LN, SUMMERFIELD, FL, 34491, Summerfield, FL 34491

$215,000

2 beds

2 baths

1,008 sq ft

House

9885 SE 177TH LN, SUMMERFIELD, FL, 34491

Community: Spruce Creek South

Stonecrest

12333 SE 177TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491

$364,000

3 beds

2 baths

1,904 sq ft

House

12333 SE 177TH LOOP, SUMMERFIELD, FL, 34...

Community: Stonecrest

Stonecrest

16863 SE 110TH COURT RD, SUMMERFIELD, FL..., Summerfield, FL 34491

$369,000

3 beds

2 baths

1,687 sq ft

House

16863 SE 110TH COURT RD, SUMMERFIELD, FL...

Community: Stonecrest

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

Questions? Call us: (689) 407-5757

Stonecrest

10864 SE 171ST STREET RD, SUMMERFIELD, F..., Summerfield, FL 34491

$375,000

3 beds

2 baths

1,736 sq ft

House

10864 SE 171ST STREET RD, SUMMERFIELD, F...

Community: Stonecrest

Del Webb Oasis

15084 CANOPY COVER DR, WINTER GARDEN, FL..., Winter Garden, FL 34787

$979,000

3 beds

3 baths

2,270 sq ft

House

15084 CANOPY COVER DR, WINTER GARDEN, FL...

Community: Del Webb Oasis

The Villages®

1606 MYRTLE BEACH DR, LADY LAKE, FL, 321..., Lady Lake, FL 32159

$175,000

2 beds

2 baths

1,332 sq ft

Modular

1606 MYRTLE BEACH DR, LADY LAKE, FL, 321...

Community: The Villages®

Sun City Center

$389,000

2 beds

2 baths

1,882 sq ft

House

706 PLUMBROOK RD, SUN CITY CENTER, FL, 3...

Community: Sun City Center

Valencia Lakes

5103 SHADY STONE PL, WIMAUMA, FL, 33598, Wimauma, FL 33598

$459,900

3 beds

2 baths

2,001 sq ft

House

5103 SHADY STONE PL, WIMAUMA, FL, 33598

Community: Valencia Lakes

Solivita

130 INDIAN WELLS AVE, KISSIMMEE, FL, 347..., Kissimmee, FL 34759

$375,000

2 beds

2 baths

2,211 sq ft

House

130 INDIAN WELLS AVE, KISSIMMEE, FL, 347...

Community: Solivita

The Villages®

$325,000

3 beds

2 baths

1,392 sq ft

House

133 OLANTA DR, THE VILLAGES, FL, 32162

Community: The Villages®

The Villages®

$435,000

3 beds

2 baths

1,724 sq ft

House

669 PEARSON ST, THE VILLAGES, FL, 32162

Community: The Villages®

The Villages®

$339,900

3 beds

2 baths

1,920 sq ft

House

3440 GALESBURG CT, THE VILLAGES, FL, 321...

Community: The Villages®

Highland Fairways

$310,000

3 beds

2 baths

1,851 sq ft

House

3658 HIGHLAND FAIRWAYS BLVD, LAKELAND, F...

Community: Highland Fairways

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

Questions? Call us: (689) 407-5757

The Villages®

$299,900

2 beds

2 baths

1,156 sq ft

Villa

1390 VIOLA CT, THE VILLAGES, FL, 32163

Community: The Villages®

The Villages®

$595,000

3 beds

2 baths

2,035 sq ft

House

1965 GATEHOUSE TER, THE VILLAGES, FL, 32...

Community: The Villages®

On Top of the World

9044 SW 91ST CIR, OCALA, FL, 34481, Ocala, FL 34481

$325,000

3 beds

2 baths

1,850 sq ft

House

9044 SW 91ST CIR, OCALA, FL, 34481

Community: On Top of the World

Del Webb Oasis

13732 FRESH IVY ST, WINTER GARDEN, FL, 3..., Winter Garden, FL 34787

$610,000

2 beds

2 baths

1,889 sq ft

House

13732 FRESH IVY ST, WINTER GARDEN, FL, 3...

Community: Del Webb Oasis

Del Webb Sunbridge

6129 CITRUS GROVE CT, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34771

$510,000

3 beds

3 baths

2,077 sq ft

House

6129 CITRUS GROVE CT, SAINT CLOUD, FL, 3...

Community: Del Webb Sunbridge

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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?

Call us: (689) 407-5757

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

1,832 sq ft

House

3 beds

3 baths

1,658 sq ft

House

2 beds

2 baths

1,156 sq ft

House

2 beds

2 baths

1,204 sq ft

Villa

3 beds

2 baths

1,736 sq ft

House

2 beds

2 baths

2,071 sq ft

House

2 beds

2 baths

1,553 sq ft

House

5 beds

6 baths

5,437 sq ft

House

3 beds

2 baths

1,527 sq ft

House

2 beds

2 baths

1,568 sq ft

House

2 beds

2 baths

1,980 sq ft

House

3 beds

2 baths

1,777 sq ft

House

3 beds

2 baths

1,905 sq ft

House

3 beds

2 baths

1,611 sq ft

House

3 beds

2 baths

1,927 sq ft

House

2 beds

2 baths

1,227 sq ft

Villa

3 beds

3 baths

2,033 sq ft

House

3 beds

2 baths

1,404 sq ft

House

2 beds

2 baths

1,138 sq ft

Villa

2 beds