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

3,654 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

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

$100ks - $800ks

Sun City Center, Sun City Center, FL

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

Venetian Bay

$300ks - $1Ms

Venetian Bay, New Smyrna Beach, FL

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

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.

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

5 rating (3 reviews)

Stonecrest

$200ks - $500ks

Stonecrest, Summerfield, FL

New and Resale | 55+ age-restricted | Built 1990 - present | 2,200 homes

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 (3 reviews)

Lake Ashton

$200ks - $500ks

Lake Ashton, Lake Wales, FL

Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 homes

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

Questions? Call us: (689) 407-5757

5 rating (1 reviews)

Ocala Palms

$200ks - $300ks

Ocala Palms, Ocala, FL

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

5 rating (5 reviews)

SummerGlen

$200ks - $400ks

SummerGlen, Ocala, FL

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

Southshore Bay

$200ks - $500ks

Southshore Bay, Wimauma, FL

New and Resale | 55+ age-restricted | Built 2017 - present | 655 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 (8 reviews)

Royal Highlands

$200ks - $400ks

Royal Highlands, Leesburg, FL

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

5 rating (7 reviews)

Kings Ridge

$200ks - $400ks

Kings Ridge, Clermont, FL

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

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

Questions? Call us: (689) 407-5757

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 (6 reviews)

Trilogy® Orlando

$200ks - $500ks

Trilogy® Orlando, Groveland, FL

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

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

2.8 rating (6 reviews)

Arlington Ridge

$200ks - $500ks

Arlington Ridge, Leesburg, FL

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

Pelican Bay Daytona Beach

$100ks - $600ks

Pelican Bay Daytona Beach, Daytona Beach, FL

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

4 rating (4 reviews)

Lakes of Mount Dora

$300ks - $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

$300ks - $900ks

Harbor Hills Country Club, Lady Lake, FL

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

2.3 rating (6 reviews)

Cherrywood

$100ks - $800ks

Cherrywood, Ocala, FL

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

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

Questions? Call us: (689) 407-5757

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

Pine Run Estates

$100ks - $200ks

Pine Run Estates, Ocala, FL

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

1 rating (1 reviews)

Sullivan Ranch

$200ks - $500ks

Sullivan Ranch, Mount Dora, FL

Resale Only | 55+ age-restricted | Built 2005 - 2020 | 692 homes

Mirada

$300ks - $500ks

Mirada, San Antonio, FL

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

5 rating (1 reviews)

Palm Cay

$100ks - $200ks

Palm Cay, Ocala, FL

Resale Only | 55+ age-restricted | Built 1985 - 1992 | 795 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)

Royal Harbor

$200ks - $800ks

Royal Harbor, Tavares, FL

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

4.8 rating (6 reviews)

Highland Lakes

$100ks - $200ks

Highland Lakes, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 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

Four Seasons at Orlando

$300ks - $600ks

Four Seasons at Orlando, Kissimmee, FL

New Construction | 55+ age-restricted | Built 2017 - present | 557 homes

8667 SW 97TH ST C, OCALA, FL, 34481

Villa

3461 FALLBROOK DR, KISSIMMEE, FL, 34759

Community: Solivita

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

Questions? Call us: (689) 407-5757

New Sun City Center

1804 PACIFIC DUNES DR, SUN CITY CENTER, ..., Sun City Center, FL 33573

$379,900

2 beds

3 baths

2,053 sq ft

House

1804 PACIFIC DUNES DR, SUN CITY CENTER, ...

Community: Sun City Center

New Scottish Highlands

27 GORDON CT, LEESBURG, FL, 34788, Leesburg, FL 34788

$215,000

2 beds

2 baths

1,252 sq ft

House

27 GORDON CT, LEESBURG, FL, 34788

Community: Scottish Highlands

New Sun City Center

608 LA JOLLA AVE, SUN CITY CENTER, FL, 3..., Sun City Center, FL 33573

$249,900

2 beds

2 baths

1,852 sq ft

House

608 LA JOLLA AVE, SUN CITY CENTER, FL, 3...

Community: Sun City Center

New Plantation at Leesburg

3447 MOUNT HOPE LOOP, LEESBURG, FL, 3474..., Leesburg, FL 34748

$299,999

3 beds

2 baths

1,868 sq ft

House

3447 MOUNT HOPE LOOP, LEESBURG, FL, 3474...

Community: Plantation at Leesburg

New Gatherings of Lake Nona

7517 LAUREATE BLVD 4403, ORLANDO, FL, 32..., Orlando, FL 32827

$329,000

2 beds

2 baths

1,549 sq ft

Condo

7517 LAUREATE BLVD 4403, ORLANDO, FL, 32...

Community: Gatherings of Lake Nona

New Southshore Bay

5336 WINDY GROVE DR, WIMAUMA, FL, 33598, Wimauma, FL 33598

$565,000

3 beds

3 baths

2,651 sq ft

House

5336 WINDY GROVE DR, WIMAUMA, FL, 33598

Community: Southshore Bay

New The Villages®

2088 VISION CT, THE VILLAGES, FL, 32163, The Villages, FL 32163

$689,000

3 beds

2 baths

2,013 sq ft

House

2088 VISION CT, THE VILLAGES, FL, 32163

Community: The Villages®

New Foxwood Lake Estates

1704 QUAIL HILL DR, LAKELAND, FL, 33810, Lakeland, FL 33810

$140,000

2 beds

2 baths

1,372 sq ft

Manufactured Home

1704 QUAIL HILL DR, LAKELAND, FL, 33810

Community: Foxwood Lake Estates

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

Questions? Call us: (689) 407-5757

New The Country Club of Mount Dora

1901 PARK FOREST BLVD, MOUNT DORA, FL, 3..., Mount Dora, FL 32757

$539,000

3 beds

2 baths

2,286 sq ft

House

1901 PARK FOREST BLVD, MOUNT DORA, FL, 3...

Community: The Country Club of Mount Dora

New Sullivan Ranch

20926 SULLIVAN RANCH BLVD, MOUNT DORA, F..., Mount Dora, FL 32757

$349,900

3 beds

2 baths

1,440 sq ft

House

20926 SULLIVAN RANCH BLVD, MOUNT DORA, F...

Community: Sullivan Ranch

New Foxwood Lake Estates

4966 DEERWOOD DR, LAKELAND, FL, 33810, Lakeland, FL 33810

$174,900

2 beds

2 baths

1,352 sq ft

Manufactured Home

4966 DEERWOOD DR, LAKELAND, FL, 33810

Community: Foxwood Lake Estates

New Twin Lakes

4902 W FOUNTAINWOOD DR, ST CLOUD, FL, 34..., St Cloud, FL 34772

$420,000

2 beds

2 baths

1,624 sq ft

House

4902 W FOUNTAINWOOD DR, ST CLOUD, FL, 34...

Community: Twin Lakes

New The Villages®

1738 AUGUSTINE DR, THE VILLAGES, FL, 321..., The Villages, FL 32159

$775,000

4 beds

3 baths

2,959 sq ft

House

1738 AUGUSTINE DR, THE VILLAGES, FL, 321...

Community: The Villages®

New Foxwood Lake Estates

1798 FOX HILL DR, LAKELAND, FL, 33810, Lakeland, FL 33810

$164,900

3 beds

2 baths

1,176 sq ft

Manufactured Home

1798 FOX HILL DR, LAKELAND, FL, 33810

Community: Foxwood Lake Estates

New Spruce Creek Preserve

11876 SW 137TH LOOP, DUNNELLON, FL, 3443..., Dunnellon, FL 34432

$249,900

3 beds

2 baths

1,760 sq ft

House

11876 SW 137TH LOOP, DUNNELLON, FL, 3443...

Community: Spruce Creek Preserve

New Highlands Ridge

5004 BIRKDALE DR, AVON PARK, FL, 33825, Avon Park, FL 33825

$299,000

2 beds

2 baths

1,648 sq ft

Villa

5004 BIRKDALE DR, AVON PARK, FL, 33825

Community: Highlands Ridge

New Four Seasons at Orlando

1999 KEY BAY TRL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747

$429,980

2 beds

2 baths

1,557 sq ft

Villa

1999 KEY BAY TRL, KISSIMMEE, FL, 34747

Community: Four Seasons at Orlando

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

Questions? Call us: (689) 407-5757

New Lakes at Laurel Highlands

2933 IVY LAKE CT, LAKELAND, FL, 33811, Lakeland, FL 33811

$389,500

5 beds

3 baths

2,674 sq ft

House

2933 IVY LAKE CT, LAKELAND, FL, 33811

Community: Lakes at Laurel Highlands

New The Villages®

5511 HEAD WAY, THE VILLAGES, FL, 32163, The Villages, FL 32163

$394,900

3 beds

2 baths

1,708 sq ft

House

5511 HEAD WAY, THE VILLAGES, FL, 32163

Community: The Villages®

New High Vista at Ridgewood Lakes

116 FLEMING LN, DAVENPORT, FL, 33837, Davenport, FL 33837

$309,000

2 beds

2 baths

1,776 sq ft

House

116 FLEMING LN, DAVENPORT, FL, 33837

Community: High Vista at Ridgewood Lakes

New The Villages®

603 ROBIN LANE AVE, WILDWOOD, FL, 34785, Wildwood, FL 34785

$159,900

2 beds

2 baths

1,352 sq ft

Manufactured Home

603 ROBIN LANE AVE, WILDWOOD, FL, 34785

Community: The Villages®

New The Villages®

1714 EL NINO ST, THE VILLAGES, FL, 32162, The Villages, FL 32162

$289,000

2 beds

2 baths

1,121 sq ft

Villa

1714 EL NINO ST, THE VILLAGES, FL, 32162

Community: The Villages®

New The Villages®

2530 FOXBRIDGE TER, THE VILLAGES, FL, 32..., The Villages, FL 32162

$324,900

3 beds

2 baths

1,392 sq ft

House

2530 FOXBRIDGE TER, THE VILLAGES, FL, 32...

Community: The Villages®

New Plantation at Leesburg

25845 GLEN EAGLE DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$325,000

3 beds

2 baths

2,047 sq ft

House

25845 GLEN EAGLE DR, LEESBURG, FL, 34748

Community: Plantation at Leesburg

New Oak Run

6541 SW 111TH LOOP, OCALA, FL, 34476, Ocala, FL 34476

$279,500

3 beds

2 baths

1,808 sq ft

House

6541 SW 111TH LOOP, OCALA, FL, 34476

Community: Oak Run

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

Questions? Call us: (689) 407-5757

New The Villages®

3284 THEODORE TER, THE VILLAGES, FL, 321..., The Villages, FL 32163

$674,900

3 beds

3 baths

2,033 sq ft

House

3284 THEODORE TER, THE VILLAGES, FL, 321...

Community: The Villages®

New The Villages®

717 TANGERINE DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$220,000

2 beds

2 baths

1,332 sq ft

Manufactured Home

717 TANGERINE DR, LADY LAKE, FL, 32159

Community: The Villages®

1 2 3 4 5 6 7 8 9 10 11 12 13 14…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

3,654 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: Apr 10, 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

110 communities near Winter Garden

3,654 homes near Winter Garden

3 beds

2 baths

1,733 sq ft

Villa

3 beds

2 baths

1,862 sq ft

House

3 beds

2 baths

1,505 sq ft

House

4 beds

2 baths

2,069 sq ft

House

2 beds

2 baths

1,541 sq ft

Villa

2 beds

2 baths

1,148 sq ft

House

2 beds

2 baths

1,343 sq ft

House

2 beds

2 baths

1,437 sq ft

House

2 beds

2 baths

1,158 sq ft

House

2 beds

2 baths

1,008 sq ft

House

3 beds

2 baths

2,213 sq ft

House

2 beds

2 baths

960 sq ft

Condo

2 beds

2 baths

1,499 sq ft

Villa

2 beds

3 baths

2,053 sq ft

House

2 beds

2 baths

1,252 sq ft

House

2 beds

2 baths

1,852 sq ft

House

3 beds

2 baths

1,868 sq ft

House

2 beds

2 baths

1,549 sq ft

Condo

3 beds

3 baths

2,651 sq ft

House

3 beds