Winter Garden, FL 55+ active adult communities & homes for sale - Page 20

3,495 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 - $700Ks

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? 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 - $900Ks

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

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 (2 reviews)

Plantation at Leesburg

$100Ks - $500Ks

Plantation at Leesburg, Leesburg, FL

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

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

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

Questions? Call us: (689) 407-5757

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

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 - $600Ks

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

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

Questions? Call us: (689) 407-5757

5 rating (8 reviews)

Royal Highlands

$200Ks - $400Ks

Royal Highlands, Leesburg, FL

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

4 rating (7 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

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

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

Questions? Call us: (689) 407-5757

5 rating (5 reviews)

SummerGlen

$100Ks - $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

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

<$100k - $300Ks

Pine Run Estates, Ocala, FL

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

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

Questions? Call us: (689) 407-5757

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

3322 MODENA WAY, NEW SMYRNA BEACH, FL, 3...

Community: Venetian Bay

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

Questions? Call us: (689) 407-5757

Baytree

2512 BAYWATER RD, TAVARES, FL, 32778, Tavares, FL 32778

$529,000

3 beds

2 baths

1,980 sq ft

House

2512 BAYWATER RD, TAVARES, FL, 32778

Community: Baytree

Spruce Creek Country Club

9105 SE 125TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491

$374,000

2 beds

2 baths

2,148 sq ft

House

9105 SE 125TH LOOP, SUMMERFIELD, FL, 344...

Community: Spruce Creek Country Club

Del Webb Orlando

451 PALENCIA PL, DAVENPORT, FL, 33837, Davenport, FL 33837

$459,900

3 beds

2 baths

2,182 sq ft

House

451 PALENCIA PL, DAVENPORT, FL, 33837

Community: Del Webb Orlando

Oak Run

10919 SW 73RD CT, OCALA, FL, 34476, Ocala, FL 34476

$379,990

4 beds

3 baths

2,551 sq ft

House

10919 SW 73RD CT, OCALA, FL, 34476

Community: Oak Run

The Villages®

$349,900

3 beds

2 baths

1,392 sq ft

House

301 PACOLET TER, THE VILLAGES, FL, 32162

Community: The Villages®

Oak Run

10864 SW 73RD CT, OCALA, FL, 34476, Ocala, FL 34476

$315,990

3 beds

2 baths

1,815 sq ft

House

10864 SW 73RD CT, OCALA, FL, 34476

Community: Oak Run

On Top of the World

8873 SW 95TH ST D, OCALA, FL, 34481, Ocala, FL 34481

$189,000

2 beds

2 baths

1,571 sq ft

Villa

8873 SW 95TH ST D, OCALA, FL, 34481

Community: On Top of the World

Stonecrest

12095 SE 178TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$299,000

3 beds

2 baths

1,663 sq ft

House

12095 SE 178TH ST, SUMMERFIELD, FL, 3449...

House

11731 EAGLE RAY LN, ORLANDO, FL, 32827

769 TURBEVILLE TER, THE VILLAGES, FL, 32...

Community: The Villages®

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

Questions? Call us: (689) 407-5757

Sun City Center

$207,000

2 beds

2 baths

1,194 sq ft

Condo

2129 ACADIA GREENS DR # 32, SUN CITY CEN...

Community: Sun City Center

The Villages®

$629,000

3 beds

2 baths

1,927 sq ft

House

2725 HALSEY TER, THE VILLAGES, FL, 32162

Community: The Villages®

The Villages®

$224,000

1 beds

1 baths

991 sq ft

Villa

2317 WHISPER ST, THE VILLAGES, FL, 32162

Community: The Villages®

New Solivita

141 MARABELLA LOOP, POINCIANA, FL, 34759, Poinciana, FL 34759

$299,999

3 beds

2 baths

1,786 sq ft

House

141 MARABELLA LOOP, POINCIANA, FL, 34759

Community: Solivita

The Villages®

$429,900

3 beds

2 baths

1,404 sq ft

House

1771 WINTHROP TER, THE VILLAGES, FL, 321...

Community: The Villages®

New Vienna Square

1620 LINZ CT, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884

$229,000

2 beds

2 baths

1,329 sq ft

Villa

1620 LINZ CT, WINTER HAVEN, FL, 33884

Community: Vienna Square

Southshore Bay

17322 HOLLY WELL AVE, WIMAUMA, FL, 33598, Wimauma, FL 33598

$240,000

2 beds

2 baths

1,406 sq ft

Villa

17322 HOLLY WELL AVE, WIMAUMA, FL, 33598

Community: Southshore Bay

The Villages®

$265,900

2 beds

2 baths

1,148 sq ft

House

1224 BALLESTEROS DR, THE VILLAGES, FL, 3...

Community: The Villages®

Plantation at Leesburg

4822 SAWGRASS LAKE CIR, LEESBURG, FL, 34..., Leesburg, FL 34748

$394,900

3 beds

3 baths

2,780 sq ft

House

4822 SAWGRASS LAKE CIR, LEESBURG, FL, 34...

Condo

148 BOB WHITE CT 1480, DAYTONA BEACH, FL...

Community: Pelican Bay Daytona Beach

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

Questions? Call us: (689) 407-5757

New On Top of the World

9015 SW 94TH ST D, OCALA, FL, 34481, Ocala, FL 34481

$189,900

2 beds

2 baths

1,861 sq ft

Villa

9015 SW 94TH ST D, OCALA, FL, 34481

Community: On Top of the World

Ocala Preserve

4171 NW 55TH CT, OCALA, FL, 34482, Ocala, FL 34482

$559,000

2 beds

2 baths

1,901 sq ft

House

4171 NW 55TH CT, OCALA, FL, 34482

Community: Ocala Preserve

1…14 15 16 17 18 19 20 21 22 23 24 25 26…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.

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

3,495 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: Jan 11, 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 20

109 communities near Winter Garden

3,495 homes near Winter Garden

4 beds

3 baths

1,915 sq ft

House

4 beds

3 baths

2,286 sq ft

House

3 beds

2 baths

1,927 sq ft

House

3 beds

2 baths

1,784 sq ft

House

3 beds

2 baths

1,916 sq ft

House

3 beds

2 baths

1,980 sq ft

House

2 beds

2 baths

2,148 sq ft

House

3 beds

2 baths

2,182 sq ft

House

4 beds

3 baths

2,551 sq ft

House

3 beds

2 baths

1,392 sq ft

House

3 beds

2 baths

1,815 sq ft

House

2 beds

2 baths

1,571 sq ft

Villa

3 beds

2 baths

1,663 sq ft

House

3 beds

2 baths

1,949 sq ft

House

3 beds

3 baths

1,658 sq ft

House

3 beds

2 baths

2,005 sq ft

House

2 beds

2 baths

1,075 sq ft

House

3 beds

2 baths

2,389 sq ft

House

3 beds

3 baths

2,208 sq ft

House

2 beds