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

2115 PLATINUM DR, SUN CITY CENTER, FL, 3...

House

2004 BERRY ROBERTS DR, SUN CITY CENTER, ...

Community: Sun City Center

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

Questions? Call us: (689) 407-5757

Sun City Center

$539,900

3 beds

2 baths

2,191 sq ft

House

1123 SIGNATURE DR, SUN CITY CENTER, FL, ...

Community: Sun City Center

Esplanade at Wiregrass Ranch

4257 ROSATTI RD, WESLEY CHAPEL, FL, 3354..., Wesley Chapel, FL 33543

$629,000

3 beds

2 baths

1,934 sq ft

House

4257 ROSATTI RD, WESLEY CHAPEL, FL, 3354...

Community: Esplanade at Wiregrass Ranch

New The Villages®

17339 SE 84TH FOXGROVE AVE, THE VILLAGES..., The Villages, FL 32162

$1,499,999

3 beds

3 baths

3,693 sq ft

House

17339 SE 84TH FOXGROVE AVE, THE VILLAGES...

Community: The Villages®

The Villages®

$325,000

2 beds

2 baths

1,382 sq ft

House

1485 MURRELLS INLET LOOP, THE VILLAGES, ...

Community: The Villages®

Ocala Palms

2197 NW 55TH AVENUE RD, OCALA, FL, 34482, Ocala, FL 34482

$329,000

3 beds

2 baths

1,488 sq ft

House

2197 NW 55TH AVENUE RD, OCALA, FL, 34482

Community: Ocala Palms

Spruce Creek Country Club

13700 SE 90TH CT, SUMMERFIELD, FL, 34491, Summerfield, FL 34491

$299,900

3 beds

2 baths

2,054 sq ft

House

13700 SE 90TH CT, SUMMERFIELD, FL, 34491

Community: Spruce Creek Country Club

The Villages®

$608,000

3 beds

2 baths

2,058 sq ft

House

1511 LAVACA LN, THE VILLAGES, FL, 32159

Community: The Villages®

The Villages®

$389,000

3 beds

2 baths

1,623 sq ft

Villa

1522 ALEXANDRIA PL, THE VILLAGES, FL, 32...

Community: The Villages®

Oak Run

8107 SW 108TH PLACE RD, OCALA, FL, 34481, Ocala, FL 34481

$199,500

2 beds

2 baths

1,160 sq ft

House

8107 SW 108TH PLACE RD, OCALA, FL, 34481

Community: Oak Run

On Top of the World

10071 SW 90TH LOOP, OCALA, FL, 34481, Ocala, FL 34481

$205,950

2 beds

2 baths

1,504 sq ft

House

10071 SW 90TH LOOP, OCALA, FL, 34481

Community: On Top of the World

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

Questions? Call us: (689) 407-5757

Sun City Center

$249,900

3 beds

2 baths

1,429 sq ft

Condo

1226 LYNDHURST GREENS DR, SUN CITY CENTE...

Community: Sun City Center

Sun City Center

$272,900

2 beds

2 baths

1,522 sq ft

House

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

Community: Sun City Center

Royal Highlands

5846 PRINCESS CAROLINE PL, LEESBURG, FL,..., Leesburg, FL 34748

$299,000

3 beds

3 baths

2,037 sq ft

House

5846 PRINCESS CAROLINE PL, LEESBURG, FL,...

Community: Royal Highlands

The Villages®

$325,000

2 beds

2 baths

1,161 sq ft

House

3568 YUCCA CT, THE VILLAGES, FL, 32163

Community: The Villages®

The Villages®

$329,900

2 beds

2 baths

1,322 sq ft

Villa

1822 ATHENS LN, THE VILLAGES, FL, 32162

Community: The Villages®

Valencia del Sol

4749 AVILA LAKES DR, WIMAUMA, FL, 33598, Wimauma, FL 33598

$365,000

2 beds

2 baths

1,648 sq ft

Villa

4749 AVILA LAKES DR, WIMAUMA, FL, 33598

Community: Valencia del Sol

The Villages®

$340,000

2 beds

2 baths

1,220 sq ft

House

1169 CALGARY ST, THE VILLAGES, FL, 32163

Community: The Villages®

The Villages®

$345,000

3 beds

2 baths

1,397 sq ft

Villa

2053 DUVAL CT, THE VILLAGES, FL, 32162

Community: The Villages®

The Villages®

$549,000

3 beds

2 baths

2,096 sq ft

House

825 ULELAH ST, THE VILLAGES, FL, 32163

Community: The Villages®

The Villages®

$279,000

2 beds

2 baths

1,227 sq ft

Villa

2306 SHEEHAN ST, THE VILLAGES, FL, 32163

House

4232 ROEBELENII DR, LAKE WALES, FL, 3385...

Community: Lake Ashton

1…9 10 11 12 13 14 15 16 17 18 19 20 21…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

1,300 sq ft

Manufactured Home

3 beds

2 baths

1,572 sq ft

House

3 beds

3 baths

2,114 sq ft

House

3 beds

2 baths

2,205 sq ft

House

3 beds

4 baths

2,737 sq ft

House

3 beds

2 baths

1,488 sq ft

House

3 beds

2 baths

1,887 sq ft

House

3 beds

2 baths

1,652 sq ft

House

2 beds

2 baths

1,927 sq ft

House

2 beds

2 baths

1,188 sq ft

Villa

4 beds

2 baths

1,751 sq ft

House

3 beds

2 baths

1,894 sq ft

House

3 beds

2 baths

1,902 sq ft

House

3 beds

2 baths

1,561 sq ft

House

2 beds

2 baths

1,944 sq ft

House

3 beds

2 baths

2,191 sq ft

House

3 beds

2 baths

1,934 sq ft

House

3 beds

3 baths

3,693 sq ft

House

2 beds

2 baths

1,382 sq ft

House

3 beds