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

3,958 homes near Winter Garden

Sort by:

Relevance

No reviews yet

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 - $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

<$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

$200Ks - $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 - $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 - $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 - $600Ks

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 - $1Ms

Twin Lakes, St. Cloud, FL

New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes

No reviews yet

Pelican Bay Daytona Beach

<$100k - $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

$200Ks - $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 - $900Ks

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

$200Ks - $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)

VillageWalk at Lake Nona

$400Ks - $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

$100Ks - $300Ks

Pennbrooke Fairways, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 homes

5 rating (1 reviews)

Sandpiper Golf & Coun...

$100Ks - $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

$300Ks - $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 - $500Ks

SummerGlen, Ocala, FL

Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,029 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 - $700Ks

Breakaway Trails, Ormond Beach, FL

New and Resale | Age-targeted | Built 1985 - present | 976 homes

4 rating (4 reviews)

Lakes of Mount Dora

$200Ks - $800Ks

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 - $800Ks

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

$100Ks - $300Ks

Highland Lakes, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes

4.3 rating (15 reviews)

Del Webb Orlando

$200Ks - $500Ks

Del Webb Orlando, Davenport, FL

Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes

No reviews yet

Pine Run Estates

$100Ks - $400Ks

Pine Run Estates, Ocala, FL

Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 homes

No reviews yet

Lake Jovita Golf and Coun...

$400Ks - $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 - $900Ks

Esplanade at Wiregrass Ra..., Wesley Chapel, FL

New and Resale | 55+ age-restricted | Built 2019 - present | 868 homes

503 VIGO ST, DAVENPORT, FL, 33837

Community: Del Webb Orlando

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

Questions? Call us: (689) 407-5757

Oak Run

8350 SW 108TH LOOP, OCALA, FL, 34481, Ocala, FL 34481

$169,900

2 beds

2 baths

1,016 sq ft

House

8350 SW 108TH LOOP, OCALA, FL, 34481

Community: Oak Run

Twin Lakes

5012 E FOUNTAINWOOD DR, SAINT CLOUD, FL,..., Saint Cloud, FL 34772

$445,000

3 beds

2 baths

1,863 sq ft

House

5012 E FOUNTAINWOOD DR, SAINT CLOUD, FL,...

Community: Twin Lakes

Del Webb Sunbridge

3018 MIRAGE PL, SAINT CLOUD, FL, 34771, Saint Cloud, FL 34771

$489,990

3 beds

3 baths

2,018 sq ft

House

3018 MIRAGE PL, SAINT CLOUD, FL, 34771

Community: Del Webb Sunbridge

Del Webb Sunbridge

6476 BARNSTORM WAY, SAINT CLOUD, FL, 347..., Saint Cloud, FL 34771

$448,490

3 beds

3 baths

1,767 sq ft

Townhouse

6476 BARNSTORM WAY, SAINT CLOUD, FL, 347...

Community: Del Webb Sunbridge

Del Webb Sunbridge

6480 BARNSTORM WAY, SAINT CLOUD, FL, 347..., Saint Cloud, FL 34771

$453,723

3 beds

3 baths

1,744 sq ft

Townhouse

6480 BARNSTORM WAY, SAINT CLOUD, FL, 347...

Community: Del Webb Sunbridge

Del Webb Sunbridge

6488 BARNSTORM WAY, SAINT CLOUD, FL, 347..., Saint Cloud, FL 34771

$448,490

3 beds

3 baths

1,767 sq ft

Townhouse

6488 BARNSTORM WAY, SAINT CLOUD, FL, 347...

Community: Del Webb Sunbridge

Del Webb Sunbridge

6484 BARNSTORM WAY, SAINT CLOUD, FL, 347..., Saint Cloud, FL 34771

$428,490

3 beds

3 baths

1,744 sq ft

Townhouse

6484 BARNSTORM WAY, SAINT CLOUD, FL, 347...

Community: Del Webb Sunbridge

JB Ranch

6444 SW 88TH LOOP, OCALA, FL, 34476, Ocala, FL 34476

$365,000

3 beds

2 baths

1,811 sq ft

House

6444 SW 88TH LOOP, OCALA, FL, 34476

Community: JB Ranch

Scottish Highlands

2411 GREENLAW CT, LEESBURG, FL, 34788, Leesburg, FL 34788

$230,000

2 beds

2 baths

1,422 sq ft

House

2411 GREENLAW CT, LEESBURG, FL, 34788

Community: Scottish Highlands

Lake Jovita Golf and Country Club

13141 PALMILLA CIR, DADE CITY, FL, 33525, Dade City, FL 33525

$489,900

2 beds

2 baths

2,019 sq ft

Villa

13141 PALMILLA CIR, DADE CITY, FL, 33525

Community: Lake Jovita Golf and Country Club

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

Questions? Call us: (689) 407-5757

Highlands Ridge

3243 E ANGLERS STRM, AVON PARK, FL, 3382..., Avon Park, FL 33825

$365,000

3 beds

3 baths

2,476 sq ft

House

3243 E ANGLERS STRM, AVON PARK, FL, 3382...

3156 SONGBIRD CIR, HARMONY, FL, 34773

Community: The Lakes at Harmony

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

Questions? Call us: (689) 407-5757

Twin Lakes

2333 DATURA LOOP, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772

$355,000

2 beds

2 baths

1,449 sq ft

Villa

2333 DATURA LOOP, SAINT CLOUD, FL, 34772

Community: Twin Lakes

Twin Lakes

2335 DATURA LOOP, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772

$340,000

2 beds

2 baths

1,351 sq ft

Villa

2335 DATURA LOOP, SAINT CLOUD, FL, 34772

Community: Twin Lakes

Twin Lakes

2331 DATURA LOOP, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772

$355,000

2 beds

2 baths

1,449 sq ft

Villa

2331 DATURA LOOP, SAINT CLOUD, FL, 34772

Community: Twin Lakes

Twin Lakes

2337 DATURA LOOP, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772

$340,000

2 beds

2 baths

1,351 sq ft

Villa

2337 DATURA LOOP, SAINT CLOUD, FL, 34772

Community: Twin Lakes

Twin Lakes

2323 DATURA LOOP, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772

$355,000

2 beds

2 baths

1,449 sq ft

Villa

2323 DATURA LOOP, SAINT CLOUD, FL, 34772

Community: Twin Lakes

The Country Club of Mount Dora

1720 PARK FOREST BLVD, MOUNT DORA, FL, 3..., Mount Dora, FL 32757

$499,000

3 beds

2 baths

2,086 sq ft

House

1720 PARK FOREST BLVD, MOUNT DORA, FL, 3...

Community: The Country Club of Mount Dora

Del Webb Orlando

251 TOMELLOSO WAY, DAVENPORT, FL, 33837, Davenport, FL 33837

$337,000

2 beds

2 baths

1,495 sq ft

House

251 TOMELLOSO WAY, DAVENPORT, FL, 33837

Community: Del Webb Orlando

Sun City Center

$275,000

3 beds

2 baths

1,934 sq ft

House

1508 W DEL WEBB BLVD, SUN CITY CENTER, F...

Community: Sun City Center

On Top of the World

8932 SW 101ST CIR, OCALA, FL, 34481, Ocala, FL 34481

$409,900

3 beds

3 baths

2,703 sq ft

House

8932 SW 101ST CIR, OCALA, FL, 34481

Community: On Top of the World

Pine Run Estates

10040 SW 98TH AVE, OCALA, FL, 34481, Ocala, FL 34481

$168,000

2 beds

2 baths

1,144 sq ft

House

10040 SW 98TH AVE, OCALA, FL, 34481

House

1415 COLONIAL CT, WINTER HAVEN, FL, 3388...

Community: Lake Ashton

1…68 69 70 71 72 73 74 75 76 77 78 79 80 81 82…99

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.

How long do listings in 55+ communities in Winter Garden typically stay on the market, and what is the average price of homes for sale?

On average, listings in 55+ communities in Winter Garden stay on the market for around 143 days. The average price of homes for sale in these communities is approximately $502,460, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Del Webb Oasis average around $502,460.

Want more information about active adult communities around Winter Garden?

Global - Lead Form - Buyer or Renter

First Name

Last Name

Phone/Mobile

Text

I'm looking to:

Rent

Buy

*55places does not provide or maintain community HOA information.

Yes, I want to subscribe to email updates from 55places.com, including newsletters, community announcements, and more.

I agree to receive SMS messages to connect me with a local expert.

By requesting more information, you agree that 55places may call, text, or email you about your inquiry, which may be made with automated means (including recorded voice messages, SMS, or text messages). You understand that your consent is not a prerequisite for buying, selling or renting a property. You may revoke your consent at any time by contacting [email protected]. Message/data rates may apply. You also agree to 55places.com’s Privacy Policy and Terms of Use.

3,958 homes near Winter Garden

Remove Boundaries ×

Map Satellite

Want to learn more about 55+ communities in Winter Garden?

Call us: (689) 407-5757

Call Us Call Us

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

106 communities near Winter Garden

3,958 homes near Winter Garden

2 beds

2 baths

1,249 sq ft

Villa

4 beds

3 baths

2,935 sq ft

House

3 beds

2 baths

2,056 sq ft

House

2 beds

2 baths

1,408 sq ft

House

2 beds

2 baths

1,468 sq ft

House

2 beds

2 baths

1,016 sq ft

House

3 beds

2 baths

1,863 sq ft

House

3 beds

3 baths

2,018 sq ft

House

3 beds

3 baths

1,767 sq ft

Townhouse

3 beds

3 baths

1,744 sq ft

Townhouse

3 beds

3 baths

1,767 sq ft

Townhouse

3 beds

3 baths

1,744 sq ft

Townhouse

3 beds

2 baths

1,811 sq ft

House

2 beds

2 baths

1,422 sq ft

House

2 beds

2 baths

2,019 sq ft

Villa

3 beds

3 baths

2,476 sq ft

House

2 beds

2 baths

1,558 sq ft

House

3 beds

2 baths

1,749 sq ft

House

2 beds

2 baths

1,102 sq ft

House

2 beds