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

9730 SW 90TH ST, OCALA, FL, 34481

Manufactured Home

114 CYPRESS RD, WILDWOOD, FL, 34785

9603 SE 137TH STREET RD, SUMMERFIELD, FL...

House

3903 WINGED ELM CT, CLERMONT, FL, 34714

Community: Palms at Serenoa

Solivita

702 TORREY PINES WAY, POINCIANA, FL, 347..., Poinciana, FL 34759

$439,000

3 beds

3 baths

2,190 sq ft

House

702 TORREY PINES WAY, POINCIANA, FL, 347...

16369 SW 14TH AVENUE RD, OCALA, FL, 3447...

Community: SummerGlen

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

Questions? Call us: (689) 407-5757

Spruce Creek North

10890 SW 63RD AVE, OCALA, FL, 34476, Ocala, FL 34476

$165,000

2 beds

2 baths

1,144 sq ft

House

10890 SW 63RD AVE, OCALA, FL, 34476

Community: Spruce Creek North

Latitude Margaritaville

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

$475,000

2 beds

2 baths

1,771 sq ft

House

484 MARGARITAVILLE AVE, DAYTONA BEACH, F...

Community: Latitude Margaritaville

Royal Highlands

21636 KING HENRY AVE, LEESBURG, FL, 3474..., Leesburg, FL 34748

$249,900

3 beds

2 baths

1,642 sq ft

House

21636 KING HENRY AVE, LEESBURG, FL, 3474...

Community: Royal Highlands

The Villages®

$410,000

3 beds

2 baths

1,512 sq ft

House

2530 SAFFRON LN, THE VILLAGES, FL, 32162

Community: The Villages®

Spruce Creek Country Club

12024 SE 91ST CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$257,500

2 beds

2 baths

1,488 sq ft

House

12024 SE 91ST CIR, SUMMERFIELD, FL, 3449...

Community: Spruce Creek Country Club

Solivita

1329 DEL MAR DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$399,900

3 beds

3 baths

2,002 sq ft

House

1329 DEL MAR DR, KISSIMMEE, FL, 34759

Community: Solivita

Lakes of Mount Dora

2440 PAWTUCKET PASS, MOUNT DORA, FL, 327..., Mount Dora, FL 32757

$609,900

2 beds

2 baths

2,663 sq ft

House

2440 PAWTUCKET PASS, MOUNT DORA, FL, 327...

Community: Lakes of Mount Dora

Esplanade at Wiregrass Ranch

4308 CAIROLI CT, WESLEY CHAPEL, FL, 3354..., Wesley Chapel, FL 33543

$500,000

2 beds

2 baths

1,694 sq ft

Villa

4308 CAIROLI CT, WESLEY CHAPEL, FL, 3354...

Community: Esplanade at Wiregrass Ranch

Southshore Bay

5319 WINDY GROVE DR, WIMAUMA, FL, 33598, Wimauma, FL 33598

$600,000

3 beds

3 baths

2,766 sq ft

House

5319 WINDY GROVE DR, WIMAUMA, FL, 33598

Community: Southshore Bay

Liberty Village

7796 SW 74TH LOOP, OCALA, FL, 34481, Ocala, FL 34481

$295,000

3 beds

2 baths

1,755 sq ft

House

7796 SW 74TH LOOP, OCALA, FL, 34481

Community: Liberty Village

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

34120 AMERICANA AVE, DADE CITY, FL, 3352..., Dade City, FL 33525

$849,900

3 beds

3 baths

2,586 sq ft

House

34120 AMERICANA AVE, DADE CITY, FL, 3352...

Community: Lake Jovita Golf and Country Club

The Lakes at Harmony

7480 WING SPAN WAY, HARMONY, FL, 34773, Harmony, FL 34773

$540,000

5 beds

4 baths

2,717 sq ft

House

7480 WING SPAN WAY, HARMONY, FL, 34773

Community: The Lakes at Harmony

Stonecrest

11019 SE 170TH LANE RD, SUMMERFIELD, FL,..., Summerfield, FL 34491

$299,900

3 beds

2 baths

1,324 sq ft

House

11019 SE 170TH LANE RD, SUMMERFIELD, FL,...

Community: Stonecrest

Solivita

164 TORINO LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$599,900

2 beds

3 baths

2,343 sq ft

House

164 TORINO LN, KISSIMMEE, FL, 34759

Community: Solivita

VillageWalk at Lake Nona

12286 REGAL LILY LN, ORLANDO, FL, 32827, Orlando, FL 32827

$939,000

4 beds

4 baths

4,072 sq ft

House

12286 REGAL LILY LN, ORLANDO, FL, 32827

Community: VillageWalk at Lake Nona

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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

4 beds

3 baths

1,684 sq ft

House

2 beds

2 baths

1,366 sq ft

House

2 beds

2 baths

1,705 sq ft

House

2 beds

2 baths

979 sq ft

Condo

2 beds

2 baths

1,670 sq ft

House

2 beds

2 baths

2,074 sq ft

House

2 beds

2 baths

1,596 sq ft

House

2 beds

2 baths

1,144 sq ft

Manufactured Home

2 beds

2 baths

1,563 sq ft

House

3 beds

3 baths

2,623 sq ft

House

2 beds

2 baths

1,559 sq ft

House

2 beds

2 baths

1,321 sq ft

House

3 beds

3 baths

2,363 sq ft

House

3 beds

2 baths

1,456 sq ft

House

3 beds

2 baths

2,126 sq ft

House

3 beds

2 baths

1,560 sq ft

House

2 beds

2 baths

1,415 sq ft

Townhouse

2 beds

2 baths

1,308 sq ft

House

2 beds

2 baths

1,822 sq ft

House

3 beds