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

3,631 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 - $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 (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

$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

$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

$200Ks - $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 - $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 - $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

825 ULELAH ST, THE VILLAGES, FL, 32163

House

4950 GLEN COE ST, LEESBURG, FL, 34748

Community: Royal Highlands

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

Questions? Call us: (689) 407-5757

On Top of the World

9901 SW 82ND STREET RD, OCALA, FL, 34481, Ocala, FL 34481

$629,900

3 beds

3 baths

3,081 sq ft

House

9901 SW 82ND STREET RD, OCALA, FL, 34481

Community: On Top of the World

The Villages®

$264,900

2 beds

2 baths

1,156 sq ft

Villa

2369 TRAVIS PL, THE VILLAGES, FL, 32162

Community: The Villages®

Stone Creek

9009 SW 52ND PLACE RD, OCALA, FL, 34481, Ocala, FL 34481

$410,010

2 beds

3 baths

2,080 sq ft

House

9009 SW 52ND PLACE RD, OCALA, FL, 34481

Community: Stone Creek

On Top of the World

8480 SW 92ND PL A, OCALA, FL, 34481, Ocala, FL 34481

$217,500

2 beds

2 baths

1,740 sq ft

Villa

8480 SW 92ND PL A, OCALA, FL, 34481

Community: On Top of the World

Royal Harbor

4954 RAINBOW TROUT RD, TAVARES, FL, 3277..., Tavares, FL 32778

$330,000

3 beds

2 baths

1,489 sq ft

House

4954 RAINBOW TROUT RD, TAVARES, FL, 3277...

Community: Royal Harbor

The Villages®

$469,000

3 beds

2 baths

1,404 sq ft

House

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

Community: The Villages®

New Trilogy® Orlando

251 SILVER MAPLE RD, GROVELAND, FL, 3473..., Groveland, FL 34736

$439,000

2 beds

2 baths

1,900 sq ft

House

251 SILVER MAPLE RD, GROVELAND, FL, 3473...

Community: Trilogy® Orlando

The Villages®

$1,249,000

3 beds

3 baths

3,143 sq ft

House

3427 CONSERVATION TRL, THE VILLAGES, FL,...

Community: The Villages®

The Villages®

$575,000

3 beds

3 baths

1,905 sq ft

House

3359 ARLYN PL, THE VILLAGES, FL, 32163

Community: The Villages®

Stonecrest

12300 SE 176TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491

$500,000

3 beds

2 baths

2,121 sq ft

House

12300 SE 176TH LOOP, SUMMERFIELD, FL, 34...

Community: Stonecrest

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

Questions? Call us: (689) 407-5757

Foxwood Lake Estates

4909 FOXWOOD LAKE DR, LAKELAND, FL, 3381..., Lakeland, FL 33810

$169,000

2 beds

2 baths

1,104 sq ft

Manufactured Home

4909 FOXWOOD LAKE DR, LAKELAND, FL, 3381...

Community: Foxwood Lake Estates

Plantation at Leesburg

5712 SUMMERBROOKE CT, LEESBURG, FL, 3474..., Leesburg, FL 34748

$599,900

3 beds

3 baths

2,961 sq ft

House

5712 SUMMERBROOKE CT, LEESBURG, FL, 3474...

Community: Plantation at Leesburg

Stone Creek

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

$598,090

3 beds

4 baths

2,990 sq ft

House

5564 SW 90TH AVE, OCALA, FL, 34481

Community: Stone Creek

Sun City Center

$120,000

2 beds

2 baths

1,516 sq ft

Villa

380 CLUB MANOR DR, SUN CITY CENTER, FL, ...

Community: Sun City Center

The Villages®

$269,000

2 beds

2 baths

1,383 sq ft

House

518 ALCAZAR CT, THE VILLAGES, FL, 32159

Community: The Villages®

Spruce Creek Country Club

13320 SE 97TH TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491

$459,000

2 beds

3 baths

2,346 sq ft

House

13320 SE 97TH TERRACE RD, SUMMERFIELD, F...

Community: Spruce Creek Country Club

The Villages®

$359,900

2 beds

2 baths

1,142 sq ft

House

2757 PLAINRIDGE LOOP, THE VILLAGES, FL, ...

Community: The Villages®

On Top of the World

8420 SW 93RD LN E, OCALA, FL, 34481, Ocala, FL 34481

$165,500

2 beds

2 baths

1,223 sq ft

Villa

8420 SW 93RD LN E, OCALA, FL, 34481

Community: On Top of the World

Pennbrooke Fairways

1045 MEADOWBEND DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$278,000

3 beds

2 baths

1,570 sq ft

House

1045 MEADOWBEND DR, LEESBURG, FL, 34748

Community: Pennbrooke Fairways

The Villages®

$369,900

3 beds

2 baths

1,398 sq ft

Villa

2101 SOUTHERN STAR WAY, 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

Stone Creek

8335 SW 58TH LOOP, OCALA, FL, 34481, Ocala, FL 34481

$361,440

3 beds

2 baths

1,662 sq ft

House

8335 SW 58TH LOOP, OCALA, FL, 34481

Community: Stone Creek

Stone Creek

8343 SW 58TH LOOP, OCALA, FL, 34481, Ocala, FL 34481

$378,920

4 beds

2 baths

1,850 sq ft

House

8343 SW 58TH LOOP, OCALA, FL, 34481

Community: Stone Creek

Stone Creek

5953 SW 82ND TERRACE RD, OCALA, FL, 3448..., Ocala, FL 34481

$544,500

3 beds

3 baths

2,483 sq ft

House

5953 SW 82ND TERRACE RD, OCALA, FL, 3448...

Community: Stone Creek

Sun City Center

$260,000

2 beds

2 baths

1,318 sq ft

Condo

1207 HUNTINGTON GREENS DR, SUN CITY CENT...

Community: Sun City Center

The Villages®

$523,500

3 beds

2 baths

2,085 sq ft

House

1178 BETHUNE WAY, THE VILLAGES, FL, 3216...

Community: The Villages®

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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

3,631 homes near Winter Garden

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

108 communities near Winter Garden

3,631 homes near Winter Garden

3 beds

2 baths

1,687 sq ft

House

2 beds

2 baths

1,629 sq ft

Condo

2 beds

2 baths

1,249 sq ft

Villa

3 beds

2 baths

1,559 sq ft

House

3 beds

2 baths

2,096 sq ft

House

2 beds

2 baths

1,555 sq ft

House

2 beds

2 baths

960 sq ft

Condo

2 beds

2 baths

1,687 sq ft

House

2 beds

2 baths

1,666 sq ft

House

2 beds

2 baths

1,948 sq ft

House

2 beds

2 baths

1,398 sq ft

House

2 beds

2 baths

1,948 sq ft

House

2 beds

2 baths

1,670 sq ft

House

2 beds

2 baths

2,271 sq ft

House

3 beds

2 baths

2,065 sq ft

House

3 beds

3 baths

3,081 sq ft

House

2 beds

2 baths

1,156 sq ft

Villa

2 beds

3 baths

2,080 sq ft

House

2 beds

2 baths

1,740 sq ft

Villa

3 beds