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

109 communities 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

4.7 rating (18 reviews)

Solivita

$300ks - $700ks

Solivita, Kissimmee, FL

New and Resale | 55+ age-restricted | Built 2000 - present | 5,900 homes

Venetian Bay

$300ks - $1Ms

Venetian Bay, New Smyrna Beach, FL

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

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

Questions? Call us: (689) 407-5757

Want to learn more about 55+ rental 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

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

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

Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.

5 rating (3 reviews)

Stonecrest

$200ks - $500ks

Stonecrest, Summerfield, FL

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

5 rating (1 reviews)

Ocala Palms

$200ks - $300ks

Ocala Palms, Ocala, FL

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

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

Questions? Call us: (689) 407-5757

5 rating (3 reviews)

Lake Ashton

$200ks - $500ks

Lake Ashton, Lake Wales, FL

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

4.7 rating (3 reviews)

Spruce Creek South

$100ks - $200ks

Spruce Creek South, Summerfield, FL

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

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

Questions? Call us: (689) 407-5757

4.7 rating (11 reviews)

Valencia Lakes

$200ks - $700ks

Valencia Lakes, Wimauma, FL

Resale Only | 55+ age-restricted | Built 2005 - 2019 | 1,631 homes

Pelican Bay Daytona Beach

$100ks - $600ks

Pelican Bay Daytona Beach, Daytona Beach, FL

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

5 rating (8 reviews)

Royal Highlands

$200ks - $400ks

Royal Highlands, Leesburg, FL

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

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

Questions? Call us: (689) 407-5757

2.8 rating (6 reviews)

Arlington Ridge

$200ks - $500ks

Arlington Ridge, Leesburg, FL

New and Resale | 55+ age-restricted | Built 2005 - present | 629 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 (7 reviews)

Kings Ridge

$200ks - $400ks

Kings Ridge, Clermont, FL

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

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

Questions? Call us: (689) 407-5757

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 (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

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

2.3 rating (6 reviews)

Cherrywood

$100ks - $800ks

Cherrywood, Ocala, FL

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

5 rating (8 reviews)

Pennbrooke Fairways

<$100k - $300ks

Pennbrooke Fairways, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 homes

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

Questions? Call us: (689) 407-5757

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

3.8 rating (5 reviews)

Marion Landing

$100ks - $300ks

Marion Landing, Ocala, FL

Resale Only | 55+ age-restricted | Built 1980 - 2004 | 600 homes

Pine Run Estates

$100ks - $200ks

Pine Run Estates, Ocala, FL

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

Cresswind at Victoria Gar...

$200ks - $500ks

Cresswind at Victoria Gar..., DeLand, FL

Resale Only | 55+ age-restricted | Built 2001 - 2022 | 1,070 homes

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

Questions? Call us: (689) 407-5757

1 rating (1 reviews)

Sullivan Ranch

$200ks - $500ks

Sullivan Ranch, Mount Dora, FL

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

5 rating (4 reviews)

Highlands Ridge

<$100k - $300ks

Highlands Ridge, Avon Park, FL

New and Resale | 55+ age-restricted | Built 1990 - present | 850 homes

Ridgehaven

$300ks - $600ks

Ridgehaven, Ormond Beach, FL

New Construction | 55+ age-restricted

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

Questions? Call us: (689) 407-5757

Four Seasons at Orlando

$300ks - $600ks

Four Seasons at Orlando, Kissimmee, FL

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

5 rating (1 reviews)

Palm Cay

$100ks - $200ks

Palm Cay, Ocala, FL

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

5043 VANTAGE CT, SAINT CLOUD, FL, 34772

Community: Twin Lakes

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

Questions? Call us: (689) 407-5757

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

Questions? Call us: (689) 407-5757

New Lake Ashton

4440 TURNBERRY LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859

$200,000

2 beds

2 baths

1,083 sq ft

House

4440 TURNBERRY LN, LAKE WALES, FL, 33859

Community: Lake Ashton

New Southshore Bay

17403 HOLLY WELL AVE, WIMAUMA, FL, 33598, Wimauma, FL 33598

$399,999

3 beds

3 baths

2,128 sq ft

House

17403 HOLLY WELL AVE, WIMAUMA, FL, 33598

Community: Southshore Bay

New Oak Run

10902 SW 71ST CIR, OCALA, FL, 34476, Ocala, FL 34476

$398,750

3 beds

2 baths

2,024 sq ft

House

10902 SW 71ST CIR, OCALA, FL, 34476

Community: Oak Run

New Mirada

10728 GABLE DIG LOOP, SAN ANTONIO, FL, 3..., San Antonio, FL 33576

$240,000

2 beds

2 baths

1,405 sq ft

Villa

10728 GABLE DIG LOOP, SAN ANTONIO, FL, 3...

Community: Mirada

New Oak Run

11534 SW 74TH CT, OCALA, FL, 34476, Ocala, FL 34476

$295,000

3 beds

2 baths

1,596 sq ft

House

11534 SW 74TH CT, OCALA, FL, 34476

Community: Oak Run

New The Villages®

508 CARRERA DR, THE VILLAGES, FL, 32159, The Villages, FL 32159

$405,900

2 beds

2 baths

1,248 sq ft

House

508 CARRERA DR, THE VILLAGES, FL, 32159

Community: The Villages®

New Spruce Creek North

10720 SW 62ND TER, OCALA, FL, 34476, Ocala, FL 34476

$217,000

3 beds

2 baths

1,526 sq ft

House

10720 SW 62ND TER, OCALA, FL, 34476

Community: Spruce Creek North

New SummerGlen

16339 SW 14TH AVENUE RD, OCALA, FL, 3447..., Ocala, FL 34473

$295,000

2 beds

2 baths

1,759 sq ft

House

16339 SW 14TH AVENUE RD, OCALA, FL, 3447...

Community: SummerGlen

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

Questions? Call us: (689) 407-5757

New Sun City Center

202 BEDFORD TRL 116, SUN CITY CENTER, FL..., Sun City Center, FL 33573

$115,000

2 beds

2 baths

960 sq ft

Condo

202 BEDFORD TRL 116, SUN CITY CENTER, FL...

Community: Sun City Center

New Sun City Center

807 TREMONT GREENS LN, SUN CITY CENTER, ..., Sun City Center, FL 33573

$165,000

2 beds

2 baths

1,236 sq ft

Condo

807 TREMONT GREENS LN, SUN CITY CENTER, ...

House

1613 E DEL WEBB BLVD, SUN CITY CENTER, F...

House

189 HANG LOOSE WAY, DAYTONA BEACH, FL, 3...

House

10029 SW 62ND CIR, OCALA, FL, 34476

House

4980 PLEASANT HOLLOW TRL, LAKELAND, FL, ...

Community: Colonnades

New Windermere

711 MORAY DR, INVERNESS, FL, 34453, Inverness, FL 34453

$209,900

2 beds

2 baths

1,186 sq ft

House

711 MORAY DR, INVERNESS, FL, 34453

Community: Windermere

New The Villages®

562 JAMES RD, THE VILLAGES, FL, 32163, The Villages, FL 32163

$545,000

3 beds

2 baths

1,944 sq ft

House

562 JAMES RD, THE VILLAGES, FL, 32163

Community: The Villages®

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

Questions? Call us: (689) 407-5757

New The Villages®

2730 MORVEN PARK WAY, THE VILLAGES, FL, ..., The Villages, FL 32162

$474,900

3 beds

2 baths

2,018 sq ft

House

2730 MORVEN PARK WAY, THE VILLAGES, FL, ...

Community: The Villages®

New The Country Club of Mount Dora

5039 GREENBRIAR TRL, MOUNT DORA, FL, 327..., Mount Dora, FL 32757

$750,000

4 beds

3 baths

2,509 sq ft

House

5039 GREENBRIAR TRL, MOUNT DORA, FL, 327...

Community: The Country Club of Mount Dora

New Palms at Serenoa

17421 BLAZING STAR CIR, CLERMONT, FL, 34..., Clermont, FL 34714

$389,000

2 beds

2 baths

1,621 sq ft

House

17421 BLAZING STAR CIR, CLERMONT, FL, 34...

Community: Palms at Serenoa

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

Questions? Call us: (689) 407-5757

New The Villages®

3322 BOARDROOM TRL, THE VILLAGES, FL, 32..., The Villages, FL 32163

$895,000

3 beds

2 baths

2,097 sq ft

House

3322 BOARDROOM TRL, THE VILLAGES, FL, 32...

Community: The Villages®

New Del Webb Sunbridge

6403 SHIMMERING SHORES LN, SAINT CLOUD, ..., Saint Cloud, FL 34771

$450,000

3 beds

2 baths

1,682 sq ft

House

6403 SHIMMERING SHORES LN, SAINT CLOUD, ...

Community: Del Webb Sunbridge

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

109 communities

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: Feb 13, 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

109 communities near Winter Garden

3,701 homes near Winter Garden

3 beds

2 baths

1,836 sq ft

House

2 beds

2 baths

1,275 sq ft

House

2 beds

2 baths

1,655 sq ft

House

2 beds

2 baths

1,560 sq ft

Manufactured Home

3 beds

3 baths

2,365 sq ft

House

2 beds

2 baths

1,083 sq ft

House

3 beds

3 baths

2,128 sq ft

House

3 beds

2 baths

2,024 sq ft

House

2 beds

2 baths

1,405 sq ft

Villa

3 beds

2 baths

1,596 sq ft

House

2 beds

2 baths

1,248 sq ft

House

3 beds

2 baths

1,526 sq ft

House

2 beds

2 baths

1,759 sq ft

House

2 beds

2 baths

960 sq ft

Condo

2 beds

2 baths

1,236 sq ft

Condo

3 beds

2 baths

1,694 sq ft

House

3 beds

2 baths

1,622 sq ft

House

3 beds

2 baths

2,039 sq ft

House

3 beds

3 baths

2,327 sq ft

House

2 beds