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

109 communities near Winter Garden

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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

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

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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

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

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.

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

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

4.1 rating (29 reviews)

Oak Run

$100ks - $300ks

Oak Run, Ocala, FL

Resale Only | 55+ age-restricted | Built 1985 - 2007 | 3,509 homes

5 rating (1 reviews)

Ocala Palms

$200ks - $300ks

Ocala Palms, Ocala, FL

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

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

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

5 rating (8 reviews)

Royal Highlands

$200ks - $400ks

Royal Highlands, Leesburg, FL

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

Southshore Bay

$200ks - $500ks

Southshore Bay, Wimauma, FL

New and Resale | 55+ age-restricted | Built 2017 - present | 655 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 (7 reviews)

Kings Ridge

$200ks - $400ks

Kings Ridge, Clermont, FL

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

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

Questions? Call us: (689) 407-5757

5 rating (5 reviews)

SummerGlen

$200ks - $400ks

SummerGlen, Ocala, FL

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

Pelican Bay Daytona Beach

$100ks - $600ks

Pelican Bay Daytona Beach, Daytona Beach, FL

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

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

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

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

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

Pine Run Estates

$100ks - $200ks

Pine Run Estates, Ocala, FL

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

5 rating (1 reviews)

Cresswind at Victoria Gar...

$200ks - $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

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

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

2.3 rating (6 reviews)

Cherrywood

$100ks - $800ks

Cherrywood, Ocala, FL

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

4.8 rating (6 reviews)

Highland Lakes

$100ks - $200ks

Highland Lakes, Leesburg, FL

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

5 rating (1 reviews)

Palm Cay

$100ks - $200ks

Palm Cay, Ocala, FL

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

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

Questions? Call us: (689) 407-5757

5 rating (1 reviews)

Royal Harbor

$200ks - $800ks

Royal Harbor, Tavares, FL

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

5 rating (8 reviews)

Pennbrooke Fairways

<$100k - $300ks

Pennbrooke Fairways, Leesburg, FL

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

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

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

Questions? Call us: (689) 407-5757

3.8 rating (5 reviews)

Marion Landing

$100ks - $300ks

Marion Landing, Ocala, FL

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

Mirada

$300ks - $500ks

Mirada, San Antonio, FL

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

1 2...3

New Cresswind at Victoria Gardens

1099 LINCOLNSHIRE DR, DELAND, FL, 32724, Deland, FL 32724

$399,000

2 beds

2 baths

1,651 sq ft

House

1099 LINCOLNSHIRE DR, DELAND, FL, 32724

9435 SE 124TH PL, SUMMERFIELD, FL, 34491

Community: Spruce Creek Country Club

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Townhouse

3446 MEDICI BLVD, NEW SMYRNA BEACH, FL, ...

Community: Venetian Bay

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Questions? Call us: (689) 407-5757

New Cresswind at Victoria Gardens

215 AVENHAM DR, DELAND, FL, 32724, Deland, FL 32724

$634,000

3 beds

3 baths

2,792 sq ft

House

215 AVENHAM DR, DELAND, FL, 32724

Community: Cresswind at Victoria Gardens

New Arlington Ridge

26954 WHITE PLAINS WAY, LEESBURG, FL, 34..., Leesburg, FL 34748

$266,000

2 beds

2 baths

1,376 sq ft

House

26954 WHITE PLAINS WAY, LEESBURG, FL, 34...

Community: Arlington Ridge

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

Questions? Call us: (689) 407-5757

New Sun City Center

2512 LANCASTER DR 2512, SUN CITY CENTER,..., Sun City Center, FL 33573

$220,000

2 beds

2 baths

1,529 sq ft

Condo

2512 LANCASTER DR 2512, SUN CITY CENTER,...

Community: Sun City Center

New Spruce Creek Country Club

13720 SE 97TH AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$439,000

2 beds

2 baths

1,888 sq ft

House

13720 SE 97TH AVE, SUMMERFIELD, FL, 3449...

Community: Spruce Creek Country Club

New Lake Jovita Golf and Country Club

33909 AMERICANA AVE, DADE CITY, FL, 3352..., Dade City, FL 33525

$965,000

4 beds

4 baths

3,737 sq ft

House

33909 AMERICANA AVE, DADE CITY, FL, 3352...

Community: Lake Jovita Golf and Country Club

New Latitude Margaritaville

281 MARGARITAVILLE AVE, DAYTONA BEACH, F..., Daytona Beach, FL 32124

$629,000

2 beds

2 baths

1,922 sq ft

House

281 MARGARITAVILLE AVE, DAYTONA BEACH, F...

Community: Latitude Margaritaville

New On Top of the World

9580 SW 85TH AVE B, OCALA, FL, 34481, Ocala, FL 34481

$108,000

2 beds

2 baths

1,422 sq ft

Villa

9580 SW 85TH AVE B, OCALA, FL, 34481

Community: On Top of the World

New Valencia del Sol

4916 SEVILLA SHORES DR, WIMAUMA, FL, 335..., Wimauma, FL 33598

$525,000

3 beds

3 baths

2,191 sq ft

House

4916 SEVILLA SHORES DR, WIMAUMA, FL, 335...

Villa

9629 SW 95TH TER D, OCALA, FL, 34481

House

13265 SE 91ST COURT RD, SUMMERFIELD, FL,...

Community: Spruce Creek Country Club

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

Questions? Call us: (689) 407-5757

New Del Webb Sunbridge

2555 PINE PRESERVE CT, ST CLOUD, FL, 347..., St Cloud, FL 34771

$895,000

3 beds

4 baths

2,866 sq ft

House

2555 PINE PRESERVE CT, ST CLOUD, FL, 347...

Community: Del Webb Sunbridge

New Latitude Margaritaville

338 LOST SHAKER WAY, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124

$635,000

3 beds

3 baths

2,393 sq ft

House

338 LOST SHAKER WAY, DAYTONA BEACH, FL, ...

Community: Latitude Margaritaville

New On Top of the World

8882 SW 85TH LOOP, OCALA, FL, 34481, Ocala, FL 34481

$449,900

3 beds

3 baths

2,381 sq ft

House

8882 SW 85TH LOOP, OCALA, FL, 34481

Community: On Top of the World

New Kings Ridge

3635 KINGSWOOD CT, CLERMONT, FL, 34711, Clermont, FL 34711

$409,000

2 beds

2 baths

1,661 sq ft

House

3635 KINGSWOOD CT, CLERMONT, FL, 34711

Community: Kings Ridge

New Lakeside Landings

10144 LAKE MIONA WAY, OXFORD, FL, 34484, Oxford, FL 34484

$535,000

4 beds

2 baths

2,319 sq ft

House

10144 LAKE MIONA WAY, OXFORD, FL, 34484

House

17559 SE 81ST PARNASSUS CT, THE VILLAGES...

Community: The Villages®

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

Questions? Call us: (689) 407-5757

New Traditions at Lake Ruby

4019 CARTERET DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884

$274,900

2 beds

2 baths

1,719 sq ft

House

4019 CARTERET DR, WINTER HAVEN, FL, 3388...

Community: Traditions at Lake Ruby

New The Villages®

2604 PRIVADA DR, THE VILLAGES, FL, 32162, The Villages, FL 32162

$269,900

3 beds

2 baths

1,210 sq ft

House

2604 PRIVADA DR, THE VILLAGES, FL, 32162

Community: The Villages®

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.

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109 communities

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

109 communities near Winter Garden

3,696 homes near Winter Garden

2 beds

2 baths

1,651 sq ft

House

2 beds

3 baths

2,693 sq ft

House

3 beds

2 baths

2,045 sq ft

House

3 beds

2 baths

1,513 sq ft

House

2 beds

2 baths

1,720 sq ft

House

2 beds

2 baths

1,870 sq ft

House

3 beds

2 baths

1,614 sq ft

House

2 beds

2 baths

1,262 sq ft

House

3 beds

2 baths

1,966 sq ft

House

2 beds

2 baths

2,056 sq ft

House

2 beds

2 baths

2,090 sq ft

House

2 beds

2 baths

2,333 sq ft

House

4 beds

4 baths

2,379 sq ft

Townhouse

3 beds

3 baths

2,792 sq ft

House

2 beds

2 baths

1,376 sq ft

House

2 beds

2 baths

1,529 sq ft

Condo

2 beds

2 baths

1,888 sq ft

House

4 beds

4 baths

3,737 sq ft

House

2 beds

2 baths

1,922 sq ft

House

2 beds