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

3,648 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 - $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 - $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 - $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

<$100k - $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 - $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

$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

$300Ks - $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 - $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? 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

$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

4.4 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

1683 SW 156TH LN, OCALA, FL, 34473

Community: SummerGlen

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

Questions? Call us: (689) 407-5757

Del Webb Orlando

336 DEL SOL AVE, DAVENPORT, FL, 33837, Davenport, FL 33837

$429,900

3 beds

3 baths

2,086 sq ft

House

336 DEL SOL AVE, DAVENPORT, FL, 33837

Community: Del Webb Orlando

New Royal Highlands

4701 INVERNESS DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$383,900

3 beds

2 baths

1,929 sq ft

House

4701 INVERNESS DR, LEESBURG, FL, 34748

Community: Royal Highlands

Solivita

915 SAN RAPHAEL ST, POINCIANA, FL, 34759, Poinciana, FL 34759

$590,000

4 beds

3 baths

3,110 sq ft

House

915 SAN RAPHAEL ST, POINCIANA, FL, 34759

Community: Solivita

Plantation at Leesburg

24817 CRANES ROOST CIR, LEESBURG, FL, 34..., Leesburg, FL 34748

$269,900

2 beds

2 baths

1,837 sq ft

House

24817 CRANES ROOST CIR, LEESBURG, FL, 34...

Community: Plantation at Leesburg

New Royal Highlands

5454 SIR CHURCHILL DR, LEESBURG, FL, 347..., Leesburg, FL 34748

$299,000

3 beds

2 baths

1,647 sq ft

House

5454 SIR CHURCHILL DR, LEESBURG, FL, 347...

Community: Royal Highlands

Solivita

125 PRIMA DR, POINCIANA, FL, 34759, Poinciana, FL 34759

$431,000

3 beds

3 baths

2,325 sq ft

House

125 PRIMA DR, POINCIANA, FL, 34759

Community: Solivita

Solivita

460 BEL AIR WAY, POINCIANA, FL, 34759, Poinciana, FL 34759

$459,000

3 beds

3 baths

2,427 sq ft

House

460 BEL AIR WAY, POINCIANA, FL, 34759

Community: Solivita

Arlington Ridge

26747 WHITE PLAINS WAY, LEESBURG, FL, 34..., Leesburg, FL 34748

$415,000

3 beds

2 baths

2,004 sq ft

House

26747 WHITE PLAINS WAY, LEESBURG, FL, 34...

Community: Arlington Ridge

New Royal Highlands

21902 KING HENRY AVE, LEESBURG, FL, 3474..., Leesburg, FL 34748

$264,900

2 beds

2 baths

1,447 sq ft

House

21902 KING HENRY AVE, LEESBURG, FL, 3474...

Community: Royal Highlands

Pine Run Estates

10067 SW 97TH LN, OCALA, FL, 34481, Ocala, FL 34481

$354,200

3 beds

2 baths

1,874 sq ft

House

10067 SW 97TH LN, OCALA, FL, 34481

House

3667 KINGSWOOD CT, CLERMONT, FL, 34711

Community: Kings Ridge

New Latitude Margaritaville

568 HIGH TIDE LN, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124

$434,900

2 beds

2 baths

1,308 sq ft

Townhouse

568 HIGH TIDE LN, DAYTONA BEACH, FL, 321...

Community: Latitude Margaritaville

Stone Creek

7646 SW 100TH CT, OCALA, FL, 34481, Ocala, FL 34481

$515,000

3 beds

3 baths

2,539 sq ft

House

7646 SW 100TH CT, OCALA, FL, 34481

Community: Stone Creek

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

Sun City Center

$144,900

2 beds

2 baths

984 sq ft

Condo

1804 FOXHUNT DR B, SUN CITY CENTER, FL, ...

Community: Sun City Center

Solivita

258 SAND PIPER DR, POINCIANA, FL, 34759, Poinciana, FL 34759

$423,500

3 beds

3 baths

2,314 sq ft

House

258 SAND PIPER DR, POINCIANA, FL, 34759

Community: Solivita

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

Questions? Call us: (689) 407-5757

Latitude Margaritaville

279 LATITUDE DR, DAYTONA BEACH, FL, 3212..., Daytona Beach, FL 32124

$429,900

2 beds

2 baths

1,205 sq ft

House

279 LATITUDE DR, DAYTONA BEACH, FL, 3212...

Community: Latitude Margaritaville

Twin Lakes

2789 SOUTHLAND ST, SAINT CLOUD, FL, 3477..., Saint Cloud, FL 34772

$530,900

3 beds

3 baths

2,365 sq ft

House

2789 SOUTHLAND ST, SAINT CLOUD, FL, 3477...

Community: Twin Lakes

Venetian Bay

453 VENETIAN VILLA DR, NEW SMYRNA BEACH,..., New Smyrna Beach, FL 32168

$585,000

5 beds

4 baths

3,051 sq ft

House

453 VENETIAN VILLA DR, NEW SMYRNA BEACH,...

Community: Venetian Bay

Southshore Bay

16833 BANNER SHELL PL, WIMAUMA, FL, 3359..., Wimauma, FL 33598

$539,900

3 beds

4 baths

2,672 sq ft

House

16833 BANNER SHELL PL, WIMAUMA, FL, 3359...

Community: Southshore Bay

New Harbor Hills Country Club

38633 LAKEVIEW WALK, LADY LAKE, FL, 3215..., Lady Lake, FL 32159

$399,900

4 beds

2 baths

2,322 sq ft

House

38633 LAKEVIEW WALK, LADY LAKE, FL, 3215...

Community: Harbor Hills Country Club

Liberty Village

7474 SW 78TH TER, OCALA, FL, 34481, Ocala, FL 34481

$387,999

4 beds

3 baths

2,292 sq ft

House

7474 SW 78TH TER, OCALA, FL, 34481

Community: Liberty Village

Del Webb Sunbridge

2793 NATURE VIEW RD, SAINT CLOUD, FL, 34..., Saint Cloud, FL 34771

$679,000

4 beds

3 baths

2,761 sq ft

House

2793 NATURE VIEW RD, SAINT CLOUD, FL, 34...

Community: Del Webb Sunbridge

New Twin Lakes

4921 CATALPA DR, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772

$539,900

3 beds

3 baths

2,365 sq ft

House

4921 CATALPA DR, SAINT CLOUD, FL, 34772

Community: Twin Lakes

New Stone Creek

10041 SW 77TH LOOP, OCALA, FL, 34481, Ocala, FL 34481

$539,000

3 beds

3 baths

2,528 sq ft

House

10041 SW 77TH LOOP, OCALA, FL, 34481

Community: Stone Creek

New Pine Run Estates

10061 SW 88TH TER, OCALA, FL, 34481, Ocala, FL 34481

$175,000

2 beds

2 baths

1,144 sq ft

House

10061 SW 88TH TER, OCALA, FL, 34481

House

5053 EL DESTINO DR, LEESBURG, FL, 34748

Community: Plantation at Leesburg

1…18 19 20 21 22 23 24 25 26 27 28 29 30…92

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

3,648 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: Nov 05, 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

108 communities near Winter Garden

3,648 homes near Winter Garden

2 beds

2 baths

1,121 sq ft

Villa

2 beds

2 baths

1,556 sq ft

Villa

2 beds

2 baths

1,352 sq ft

Manufactured Home

3 beds

2 baths

1,303 sq ft

House

3 beds

2 baths

2,093 sq ft

House

3 beds

3 baths

2,086 sq ft

House

3 beds

2 baths

1,929 sq ft

House

4 beds

3 baths

3,110 sq ft

House

2 beds

2 baths

1,837 sq ft

House

3 beds

2 baths

1,647 sq ft

House

3 beds

3 baths

2,325 sq ft

House

3 beds

3 baths

2,427 sq ft

House

3 beds

2 baths

2,004 sq ft

House

2 beds

2 baths

1,447 sq ft

House

3 beds

2 baths

1,874 sq ft

House

2 beds

2 baths

1,637 sq ft

House

3 beds

2 baths

1,858 sq ft

House

2 beds

2 baths

1,393 sq ft

House

3 beds

2 baths

1,930 sq ft

House

2 beds