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

3,497 homes near Winter Garden

Sort by:

Relevance

4 rating (17 reviews)

The Villages®

$100ks - $1Ms

The Villages®, The Villages, FL

New and Resale | 55+ age-restricted | Built 1978 - present | 70,000 homes

3.8 rating (14 reviews)

Sun City Center

$100ks - $800ks

Sun City Center, Sun City Center, FL

Resale Only | 55+ age-restricted | Built 1961 - 2018 | 9,500 homes

4 rating (56 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

4.2 rating (10 reviews)

Stone Creek

$200ks - $500ks

Stone Creek, Ocala, FL

New and Resale | 55+ age-restricted | Built 2006 - present | 3,800 homes

4.7 rating (18 reviews)

Solivita

$300ks - $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

4.5 rating (11 reviews)

Spruce Creek Country Club

$100ks - $400ks

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 - $300ks

Plantation at Leesburg, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1987 - 2008 | 2,820 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

3.6 rating (48 reviews)

Latitude Margaritaville

$300ks - $800ks

Latitude Margaritaville, Daytona Beach, FL

Resale Only | 55+ age-restricted | Built 2017 - 2025 | 3,900 homes

Venetian Bay

$300ks - $1Ms

Venetian Bay, New Smyrna Beach, FL

New and Resale | Age-targeted | Built 2004 - present | 1,561 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.

4.6 rating (5 reviews)

Ocala Preserve

$100ks - $500ks

Ocala Preserve, Ocala, FL

New and Resale | 55+ age-restricted | Built 2014 - present | 1,800 homes

5 rating (1 reviews)

Ocala Palms

$200ks - $300ks

Ocala Palms, Ocala, FL

Resale Only | 55+ age-restricted | Built 1994 - 1997 | 1,076 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

5 rating (3 reviews)

Stonecrest

$200ks - $500ks

Stonecrest, Summerfield, FL

Resale Only | 55+ age-restricted | Built 1990 - 2024 | 2,224 homes

2.8 rating (6 reviews)

Arlington Ridge

$200ks - $500ks

Arlington Ridge, Leesburg, FL

New and Resale | 55+ age-restricted | Built 2005 - present | 629 homes

3.8 rating (6 reviews)

Trilogy® Orlando

$200ks - $500ks

Trilogy® Orlando, Groveland, FL

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

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

Questions? Call us: (689) 407-5757

5 rating (5 reviews)

SummerGlen

$200ks - $400ks

SummerGlen, Ocala, FL

Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,024 homes

5 rating (3 reviews)

Twin Lakes

$200ks - $600ks

Twin Lakes, St. Cloud, FL

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

Southshore Bay

$200ks - $500ks

Southshore Bay, Wimauma, FL

New and Resale | 55+ age-restricted | Built 2017 - present | 655 homes

5 rating (8 reviews)

Royal Highlands

$200ks - $400ks

Royal Highlands, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 homes

5 rating (7 reviews)

Kings Ridge

$200ks - $400ks

Kings Ridge, Clermont, FL

Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 homes

4 rating (7 reviews)

Tampa Bay Golf and Countr...

$200ks - $500ks

Tampa Bay Golf and Countr..., San Antonio, FL

Resale Only | 55+ age-restricted | Built 1994 - 2015 | 1,336 homes

3.8 rating (4 reviews)

Spruce Creek South

$100ks - $200ks

Spruce Creek South, Summerfield, FL

Resale Only | 55+ age-restricted | Built 1989 - 1995 | 1,650 homes

Pelican Bay Daytona Beach

$100ks - $600ks

Pelican Bay Daytona Beach, Daytona Beach, FL

Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 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

4 rating (4 reviews)

Lakes of Mount Dora

$300ks - $1Ms

Lakes of Mount Dora, Mount Dora, FL

New and Resale | 55+ age-restricted | Built 2006 - present | 950 homes

4.7 rating (11 reviews)

Valencia Lakes

$200ks - $700ks

Valencia Lakes, Wimauma, FL

Resale Only | 55+ age-restricted | Built 2005 - 2019 | 1,631 homes

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

Questions? Call us: (689) 407-5757

4 rating (2 reviews)

Harbor Hills Country Club

$300ks - $900ks

Harbor Hills Country Club, Lady Lake, FL

New and Resale | Age-targeted | Built 1989 - present | 940 homes

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

5 rating (1 reviews)

Del Webb Sunbridge

$400ks - $800ks

Del Webb Sunbridge, St. Cloud, FL

New and Resale | 55+ age-restricted | Built 2019 - present | 1,300 homes

3.6 rating (5 reviews)

Heritage Hills

$200ks - $400ks

Heritage Hills, Clermont, FL

New and Resale | 55+ age-restricted | Built 2006 - present | 1,154 homes

5 rating (1 reviews)

Cresswind at Victoria Gar...

$200ks - $500ks

Cresswind at Victoria Gar..., DeLand, FL

Resale Only | 55+ age-restricted | Built 2001 - 2022 | 1,070 homes

Mirada

$300ks - $500ks

Mirada, San Antonio, FL

New and Resale | 55+ age-restricted | Built 2019 - present | 858 homes

3.8 rating (5 reviews)

Marion Landing

$100ks - $300ks

Marion Landing, Ocala, FL

Resale Only | 55+ age-restricted | Built 1980 - 2004 | 600 homes

2.3 rating (6 reviews)

Cherrywood

$100ks - $800ks

Cherrywood, Ocala, FL

Resale Only | 55+ age-restricted | Built 1996 - 2003 | 700 homes

Quail Meadow

$200ks - $400ks

Quail Meadow, Ocala, FL

Resale Only | 55+ age-restricted | Built 1988 - 2006 | 460 homes

The Lakes at Harmony

$200ks - $400ks

The Lakes at Harmony, Harmony, FL

New and Resale | 55+ age-restricted | Built 2016 - present | 400 homes

Summer Trees

$200ks - $400ks

Summer Trees, Port Orange, FL

Resale Only | 55+ age-restricted | Built 1976 - 2005 | 500 homes

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

Questions? Call us: (689) 407-5757

Pine Run Estates

$100ks - $200ks

Pine Run Estates, Ocala, FL

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

5 rating (1 reviews)

Royal Harbor

$200ks - $800ks

Royal Harbor, Tavares, FL

Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 homes

4912 SANDY GLEN WAY, WIMAUMA, FL, 33598

Community: Valencia Lakes

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

Questions? Call us: (689) 407-5757

Ocala Palms

1915 NW 50TH CIR, OCALA, FL, 34482, Ocala, FL 34482

$220,000

2 beds

2 baths

1,182 sq ft

House

1915 NW 50TH CIR, OCALA, FL, 34482

Community: Ocala Palms

The Villages®

$1,550,000

4 beds

4 baths

3,976 sq ft

House

2756 CUTTERS COR, THE VILLAGES, FL, 3216...

Community: The Villages®

Stone Creek

9419 SW 66TH LOOP, OCALA, FL, 34481, Ocala, FL 34481

$319,000

2 beds

2 baths

1,596 sq ft

House

9419 SW 66TH LOOP, OCALA, FL, 34481

Community: Stone Creek

Sun City Center

$423,000

3 beds

2 baths

2,482 sq ft

Condo

2207 S PEBBLE BEACH BLVD, SUN CITY CENTE...

Community: Sun City Center

Ocala Palms

5600 NW 27TH PL, OCALA, FL, 34482, Ocala, FL 34482

$339,000

3 beds

2 baths

2,367 sq ft

House

5600 NW 27TH PL, OCALA, FL, 34482

Community: Ocala Palms

Cresswind DeLand

1226 TRIDENT LOOP, DELAND, FL, 32724, Deland, FL 32724

$389,990

3 beds

2 baths

1,724 sq ft

House

1226 TRIDENT LOOP, DELAND, FL, 32724

Community: Cresswind DeLand

The Villages®

$349,900

3 beds

2 baths

1,550 sq ft

House

1504 LYNCHBURG LOOP, THE VILLAGES, FL, 3...

Community: The Villages®

Cresswind DeLand

1279 EDEN ROCK CT, DELAND, FL, 32724, Deland, FL 32724

$367,990

2 beds

2 baths

1,434 sq ft

House

1279 EDEN ROCK CT, DELAND, FL, 32724

Community: Cresswind DeLand

Cresswind at Lake Harris

1584 BELLAGIO LOOP, TAVARES, FL, 32778, Tavares, FL 32778

$386,990

3 beds

2 baths

1,724 sq ft

House

1584 BELLAGIO LOOP, TAVARES, FL, 32778

Community: Cresswind at Lake Harris

Solivita

116 GLENDALE CT, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$299,900

2 beds

2 baths

1,655 sq ft

House

116 GLENDALE CT, KISSIMMEE, FL, 34759

Community: Solivita

On Top of the World

8830 SW 98 PL M, OCALA, FL, 34481, Ocala, FL 34481

$120,000

2 beds

3 baths

1,764 sq ft

Townhouse

8830 SW 98 PL M, OCALA, FL, 34481

House

4504 NW 32ND ST, OCALA, FL, 34482

House

8340 SW 108TH LOOP, OCALA, FL, 34481

Community: Oak Run

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

Questions? Call us: (689) 407-5757

Mirada

31565 CANNON RUSH DR, SAN ANTONIO, FL, 3..., San Antonio, FL 33576

$375,000

2 beds

2 baths

1,968 sq ft

House

31565 CANNON RUSH DR, SAN ANTONIO, FL, 3...

Community: Mirada

Lake Ashton

4083 ASHTON CLUB DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859

$499,000

3 beds

2 baths

2,477 sq ft

House

4083 ASHTON CLUB DR, LAKE WALES, FL, 338...

Community: Lake Ashton

1…49 50 51 52 53 54 55 56 57 58 59 60 61…88

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 399 days. The average price of homes for sale in these communities is approximately $476,615, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Del Webb Oasis average around $476,615.

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.

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

Call us: (689) 407-5757

3,497 homes

Remove Boundaries ×

Map Satellite

The listings data displayed on this medium comes in part from the Real Estate Information Network Inc. (REIN) and has been authorized by participating listing Broker Members of REIN for display. REIN's listings are based upon Data submitted by its Broker Members, and REIN therefore makes no representation or warranty regarding the accuracy of the Data. All users of REIN's listings database should confirm the accuracy of the listing information directly with the listing agent.
© 2026 REIN. REIN's listings Data and information is protected under federal copyright laws. Federal law prohibits, among other acts, the unauthorized copying or alteration of, or preparation of derivative works from, all or any part of copyrighted materials, including certain compilations of Data and information. COPYRIGHT VIOLATORS MAY BE SUBJECT TO SEVERE FINES AND PENALTIES UNDER FEDERAL LAW.
REIN updates its listings on a daily basis. Data last updated: May 25, 2026.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us

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

113 communities near Winter Garden

3,497 homes near Winter Garden

3 beds

3 baths

2,512 sq ft

House

2 beds

2 baths

1,016 sq ft

House

3 beds

2 baths

1,710 sq ft

House

2 beds

2 baths

1,291 sq ft

House

3 beds

2 baths

2,000 sq ft

House

2 beds

2 baths

1,182 sq ft

House

4 beds

4 baths

3,976 sq ft

House

2 beds

2 baths

1,596 sq ft

House

3 beds

2 baths

2,482 sq ft

Condo

3 beds

2 baths

2,367 sq ft

House

3 beds

2 baths

1,724 sq ft

House

3 beds

2 baths

1,550 sq ft

House

2 beds

2 baths

1,434 sq ft

House

3 beds

2 baths

1,724 sq ft

House

2 beds

2 baths

1,655 sq ft

House

2 beds

3 baths

1,764 sq ft

Townhouse

2 beds

2 baths

1,955 sq ft

House

2 beds

2 baths

1,434 sq ft

House

2 beds

2 baths

1,563 sq ft

House

3 beds