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

3,551 homes near Winter Garden

Sort by:

Relevance

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 - $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 - $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 - $600Ks

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, FL? 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 - $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 - $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 - $600Ks

Twin Lakes, St. Cloud, FL

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

Pelican Bay Daytona Beach

$100Ks - $400Ks

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, FL? 55places can help!

Questions? Call us: (689) 407-5757

4.7 rating (3 reviews)

Spruce Creek South

$100Ks - $400Ks

Spruce Creek South, Summerfield, FL

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

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

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 - $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)

VillageWalk at Lake Nona

$300Ks - $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, FL? 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 - $400Ks

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

Breakaway Trails

$400Ks - $800Ks

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, FL? 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

4.4 rating (16 reviews)

Del Webb Orlando

$300Ks - $400Ks

Del Webb Orlando, Davenport, FL

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

Pine Run Estates

$100Ks - $300Ks

Pine Run Estates, Ocala, FL

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

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

Esplanade at Wiregrass Ra...

$400Ks - $1Ms

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

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

1408 W DEL WEBB BLVD, SUN CITY CENTER, F...

Community: Sun City Center

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

Questions? Call us: (689) 407-5757

Four Seasons at Orlando

1980 FLORA PASS PL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747

$595,000

3 beds

2 baths

2,202 sq ft

House

1980 FLORA PASS PL, KISSIMMEE, FL, 34747

Community: Four Seasons at Orlando

Pelican Bay Daytona Beach

42 CORMORANT CIR, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32119

$409,900

4 beds

2 baths

1,862 sq ft

House

42 CORMORANT CIR, DAYTONA BEACH, FL, 321...

Community: Pelican Bay Daytona Beach

Sun City Center

$369,000

4 beds

3 baths

1,684 sq ft

House

672 ALLEGHENY DR, SUN CITY CENTER, FL, 3...

Community: Sun City Center

The Villages®

$325,000

2 beds

2 baths

1,344 sq ft

House

2117 ZARAGOZA PL, THE VILLAGES, FL, 3215...

Community: The Villages®

The Villages®

$638,900

3 beds

2 baths

1,633 sq ft

Villa

5967 FREITAG AVE, THE VILLAGES, FL, 3216...

Community: The Villages®

The Villages®

$175,000

2 beds

2 baths

1,188 sq ft

Manufactured Home

407 TARRSON BLVD, THE VILLAGES, FL, 3215...

Community: The Villages®

Spruce Creek Country Club

13235 SE 97TH TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491

$365,000

2 beds

2 baths

2,149 sq ft

House

13235 SE 97TH TERRACE RD, SUMMERFIELD, F...

Community: Spruce Creek Country Club

The Villages®

$264,000

3 beds

2 baths

1,265 sq ft

House

16903 SE 96TH CHAPELWOOD CIR, THE VILLAG...

Community: The Villages®

Spruce Creek Country Club

13520 SE 87TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$350,000

2 beds

2 baths

1,554 sq ft

House

13520 SE 87TH CIR, SUMMERFIELD, FL, 3449...

Community: Spruce Creek Country Club

On Top of the World

10589 SW 98TH LN, OCALA, FL, 34481, Ocala, FL 34481

$420,000

2 beds

2 baths

1,703 sq ft

House

10589 SW 98TH LN, OCALA, FL, 34481

House

6059 CONDOR DR, LAKELAND, FL, 33809

Community: Sandpiper Golf & Country Club

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

Questions? Call us: (689) 407-5757

Cherrywood

9948 SW 62ND AVE, OCALA, FL, 34476, Ocala, FL 34476

$249,900

3 beds

2 baths

1,494 sq ft

House

9948 SW 62ND AVE, OCALA, FL, 34476

Community: Cherrywood

The Villages®

$510,000

3 beds

2 baths

1,995 sq ft

House

16822 SE 80TH BELLAVISTA CIR, THE VILLAG...

Community: The Villages®

Stonecrest

17409 SE 111TH CIR, SUMMERFIELD, FL, 344..., Summerfield, FL 34491

$330,000

3 beds

2 baths

1,700 sq ft

House

17409 SE 111TH CIR, SUMMERFIELD, FL, 344...

Community: Stonecrest

Spruce Creek South

17551 SE 96TH CT, SUMMERFIELD, FL, 34491, Summerfield, FL 34491

$264,900

3 beds

2 baths

1,498 sq ft

House

17551 SE 96TH CT, SUMMERFIELD, FL, 34491

Community: Spruce Creek South

Del Webb Orlando

672 CORDOBA DR, DAVENPORT, FL, 33837, Davenport, FL 33837

$389,900

2 beds

2 baths

1,956 sq ft

House

672 CORDOBA DR, DAVENPORT, FL, 33837

Community: Del Webb Orlando

Twin Lakes

5017 E FOUNTAINWOOD DR, SAINT CLOUD, FL,..., Saint Cloud, FL 34772

$425,000

3 beds

2 baths

1,863 sq ft

House

5017 E FOUNTAINWOOD DR, SAINT CLOUD, FL,...

Community: Twin Lakes

Oak Run

10777 SW 71ST CIR, OCALA, FL, 34476, Ocala, FL 34476

$330,000

3 beds

3 baths

2,082 sq ft

House

10777 SW 71ST CIR, OCALA, FL, 34476

Community: Oak Run

Southshore Bay

17255 HOLLY WELL AVE, WIMAUMA, FL, 33598, Wimauma, FL 33598

$310,000

2 beds

2 baths

1,614 sq ft

Townhouse

17255 HOLLY WELL AVE, WIMAUMA, FL, 33598

Community: Southshore Bay

The Villages®

$539,900

3 beds

2 baths

1,924 sq ft

House

4216 BALCHARAN TER, THE VILLAGES, FL, 32...

Community: The Villages®

Plantation at Leesburg

3603 WESTOVER CIR, LEESBURG, FL, 34748, Leesburg, FL 34748

$415,000

2 beds

2 baths

2,399 sq ft

House

3603 WESTOVER CIR, LEESBURG, FL, 34748

Condo

920 VILLEROY GREENS DR, SUN CITY CENTER,...

Community: Sun City Center

1…3 4 5 6 7 8 9 10 11 12 13 14 15…89

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?

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

3,551 homes near Winter Garden

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.
© 2025 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: Dec 16, 2025.
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

109 communities near Winter Garden

3,551 homes near Winter Garden

2 beds

2 baths

1,324 sq ft

Manufactured Home

3 beds

2 baths

2,026 sq ft

House

3 beds

2 baths

1,392 sq ft

House

2 beds

2 baths

1,438 sq ft

House

2 beds

2 baths

1,398 sq ft

House

3 beds

2 baths

2,202 sq ft

House

4 beds

2 baths

1,862 sq ft

House

4 beds

3 baths

1,684 sq ft

House

2 beds

2 baths

1,344 sq ft

House

3 beds

2 baths

1,633 sq ft

Villa

2 beds

2 baths

1,188 sq ft

Manufactured Home

2 beds

2 baths

2,149 sq ft

House

3 beds

2 baths

1,265 sq ft

House

2 beds

2 baths

1,554 sq ft

House

2 beds

2 baths

1,703 sq ft

House

3 beds

2 baths

1,446 sq ft

Villa

3 beds

2 baths

1,541 sq ft

House

2 beds

2 baths

1,330 sq ft

Condo

3 beds

2 baths

2,205 sq ft

House

2 beds