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

$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 - $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

3.8 rating (6 reviews)

Trilogy® Orlando

$300Ks - $600Ks

Trilogy® Orlando, Groveland, FL

Resale Only | 55+ age-restricted | Built 2005 - 2022 | 1,500 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)

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 - $900Ks

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

$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

The Villages®

1705 KILEY CT, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$197,500

3 beds

2 baths

1,292 sq ft

Manufactured Home

1705 KILEY CT, LADY LAKE, FL, 32159

Community: The Villages®

The Villages®

$597,500

4 beds

3 baths

2,407 sq ft

House

1644 ARIAL PL, THE VILLAGES, FL, 32162

1639 W SCHWARTZ BLVD, THE VILLAGES, FL, ...

Community: The Villages®

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

Questions? Call us: (689) 407-5757

Trilogy® Orlando

406 ALCOVE DR, GROVELAND, FL, 34736, Groveland, FL 34736

$330,000

2 beds

2 baths

1,568 sq ft

House

406 ALCOVE DR, GROVELAND, FL, 34736

Community: Trilogy® Orlando

The Villages®

$409,900

3 beds

2 baths

1,861 sq ft

House

879 ASTOR WAY, THE VILLAGES, FL, 32162

Community: The Villages®

Carillon Lakes

3870 WHISTLEWOOD CIR, LAKELAND, FL, 3381..., Lakeland, FL 33811

$429,500

3 beds

2 baths

2,121 sq ft

House

3870 WHISTLEWOOD CIR, LAKELAND, FL, 3381...

Community: Carillon Lakes

Pennbrooke Fairways

544 GRAND VISTA TRL, LEESBURG, FL, 34748, Leesburg, FL 34748

$314,900

3 beds

2 baths

1,869 sq ft

House

544 GRAND VISTA TRL, LEESBURG, FL, 34748

Community: Pennbrooke Fairways

The Villages®

$560,000

3 beds

2 baths

2,260 sq ft

House

2301 CLYMER CT, THE VILLAGES, FL, 32163

Community: The Villages®

On Top of the World

8655 SW 98TH STREET RD G, OCALA, FL, 344..., Ocala, FL 34481

$179,900

2 beds

2 baths

1,424 sq ft

Villa

8655 SW 98TH STREET RD G, OCALA, FL, 344...

Community: On Top of the World

Stone Creek

9395 SW 70TH LOOP, OCALA, FL, 34481, Ocala, FL 34481

$477,000

3 beds

3 baths

2,280 sq ft

House

9395 SW 70TH LOOP, OCALA, FL, 34481

Community: Stone Creek

The Villages®

$311,000

2 beds

2 baths

1,094 sq ft

Villa

623 DELGADO AVE, THE VILLAGES, FL, 32159

Community: The Villages®

Highland Fairways

1967 LONG BOAT DR, LAKELAND, FL, 33810, Lakeland, FL 33810

$299,500

2 beds

2 baths

1,955 sq ft

House

1967 LONG BOAT DR, LAKELAND, FL, 33810

Community: Highland Fairways

Ocala Preserve

5505 NW 40TH LOOP, OCALA, FL, 34482, Ocala, FL 34482

$319,900

2 beds

2 baths

1,470 sq ft

House

5505 NW 40TH LOOP, OCALA, FL, 34482

Manufactured Home

1708 LAUREN LN, LADY LAKE, FL, 32159

Community: The Villages®

Breakaway Trails

9 CRESCENT LAKE WAY, ORMOND BEACH, FL, 3..., Ormond Beach, FL 32174

$699,000

4 beds

4 baths

2,852 sq ft

House

9 CRESCENT LAKE WAY, ORMOND BEACH, FL, 3...

Community: Breakaway Trails

The Villages®

$379,000

2 beds

2 baths

1,462 sq ft

Villa

3213 ARCHER AVE, THE VILLAGES, FL, 32162

Community: The Villages®

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

Questions? Call us: (689) 407-5757

Kings Ridge

2000 FARMINGTON CT, CLERMONT, FL, 34711, Clermont, FL 34711

$455,275

3 beds

2 baths

2,223 sq ft

House

2000 FARMINGTON CT, CLERMONT, FL, 34711

Community: Kings Ridge

The Villages®

$295,500

2 beds

2 baths

1,357 sq ft

House

1613 CHERRY HILL RD, THE VILLAGES, FL, 3...

Community: The Villages®

The Villages®

$525,000

3 beds

2 baths

2,030 sq ft

House

1751 ASHWOOD RUN, THE VILLAGES, FL, 3216...

Community: The Villages®

The Villages®

$399,247

3 beds

2 baths

1,530 sq ft

House

1010 VENTURA DR, THE VILLAGES, FL, 32159

Community: The Villages®

The Villages®

$360,500

3 beds

2 baths

1,692 sq ft

House

8373 SE 177TH BARTRAM LOOP, THE VILLAGES...

Community: The Villages®

Plantation at Leesburg

3624 BELLE ROSE DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$375,000

4 beds

3 baths

2,820 sq ft

House

3624 BELLE ROSE DR, LEESBURG, FL, 34748

Community: Plantation at Leesburg

Four Seasons at Orlando

2026 KEY BAY TRL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747

$324,900

2 beds

2 baths

1,557 sq ft

Villa

2026 KEY BAY TRL, KISSIMMEE, FL, 34747

Community: Four Seasons at Orlando

On Top of the World

8671 SW 97TH ST C, OCALA, FL, 34481, Ocala, FL 34481

$167,900

2 beds

2 baths

1,341 sq ft

Villa

8671 SW 97TH ST C, OCALA, FL, 34481

Community: On Top of the World

New Plantation at Leesburg

25447 CRESTWATER DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$219,900

2 beds

2 baths

1,348 sq ft

House

25447 CRESTWATER DR, LEESBURG, FL, 34748

Community: Plantation at Leesburg

New The Villages®

980 PICKERING PATH, THE VILLAGES, FL, 32..., The Villages, FL 32163

$1,093,800

3 beds

2 baths

2,462 sq ft

House

980 PICKERING PATH, THE VILLAGES, FL, 32...

House

561 DAVINCI PASS, POINCIANA, FL, 34759

Community: Solivita

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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

3,573 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

3 beds

2 baths

1,292 sq ft

Manufactured Home

4 beds

3 baths

2,407 sq ft

House

2 beds

2 baths

1,008 sq ft

House

2 beds

2 baths

1,383 sq ft

House

2 beds

2 baths

1,144 sq ft

Manufactured Home

2 beds

2 baths

1,568 sq ft

House

3 beds

2 baths

1,861 sq ft

House

3 beds

2 baths

2,121 sq ft

House

3 beds

2 baths

1,869 sq ft

House

3 beds

2 baths

2,260 sq ft

House

2 beds

2 baths

1,424 sq ft

Villa

3 beds

3 baths

2,280 sq ft

House

2 beds

2 baths

1,094 sq ft

Villa

2 beds

2 baths

1,955 sq ft

House

2 beds

2 baths

1,470 sq ft

House

2 beds

2 baths

1,182 sq ft

House

2 beds

2 baths

1,356 sq ft

House

2 beds

2 baths

1,440 sq ft

Manufactured Home

2 beds

2 baths

1,147 sq ft

House

3 beds