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

113 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 rating (56 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

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 (2 reviews)

Plantation at Leesburg

$100ks - $300ks

Plantation at Leesburg, Leesburg, FL

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

Venetian Bay

$300ks - $1Ms

Venetian Bay, New Smyrna Beach, FL

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

5 rating (1 reviews)

Ocala Palms

$200ks - $300ks

Ocala Palms, Ocala, FL

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

5 rating (3 reviews)

Stonecrest

$200ks - $500ks

Stonecrest, Summerfield, FL

Resale Only | 55+ age-restricted | Built 1990 - 2024 | 2,224 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

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 (5 reviews)

SummerGlen

$200ks - $400ks

SummerGlen, Ocala, FL

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

Want to learn more about 55+ 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 (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

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 (8 reviews)

Royal Highlands

$200ks - $400ks

Royal Highlands, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 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 (7 reviews)

Kings Ridge

$200ks - $400ks

Kings Ridge, Clermont, FL

Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 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 (1 reviews)

Sandpiper Golf & Coun...

$100ks - $300ks

Sandpiper Golf & Coun..., Lakeland, FL

New and Resale | 55+ age-restricted | Built 1985 - present | 1,193 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

4.7 rating (11 reviews)

Valencia Lakes

$200ks - $700ks

Valencia Lakes, Wimauma, FL

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

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

3.8 rating (5 reviews)

Marion Landing

$100ks - $300ks

Marion Landing, Ocala, FL

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

2.3 rating (6 reviews)

Cherrywood

$100ks - $800ks

Cherrywood, Ocala, FL

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

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 (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

5 rating (1 reviews)

Palm Cay

$100ks - $200ks

Palm Cay, Ocala, FL

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

Mirada

$300ks - $500ks

Mirada, San Antonio, FL

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

Quail Meadow

$200ks - $400ks

Quail Meadow, Ocala, FL

Resale Only | 55+ age-restricted | Built 1988 - 2006 | 460 homes

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

Questions? Call us: (689) 407-5757

The Lakes at Harmony

$200ks - $400ks

The Lakes at Harmony, Harmony, FL

New and Resale | 55+ age-restricted | Built 2016 - present | 400 homes

Breakaway Trails

$400ks - $800ks

Breakaway Trails, Ormond Beach, FL

New and Resale | Age-targeted | Built 1985 - present | 976 homes

1 2...3

New Oak Run

11480 SW 76TH AVE, OCALA, FL, 34476, Ocala, FL 34476

$239,900

3 beds

2 baths

1,757 sq ft

House

11480 SW 76TH AVE, OCALA, FL, 34476

Community: Oak Run

New Southshore Bay

17554 HOLLY WELL AVE, WIMAUMA, FL, 33598, Wimauma, FL 33598

$299,900

2 beds

3 baths

1,737 sq ft

Townhouse

17554 HOLLY WELL AVE, WIMAUMA, FL, 33598

Community: Southshore Bay

New Spring Lake Towers

700 MIRROR TER 507, WINTER HAVEN, FL, 33..., Winter Haven, FL 33881

$164,900

2 beds

2 baths

1,351 sq ft

Condo

700 MIRROR TER 507, WINTER HAVEN, FL, 33...

Community: Spring Lake Towers

New Cherrywood

8872 SW 63RD AVE, OCALA, FL, 34476, Ocala, FL 34476

$319,900

4 beds

2 baths

2,039 sq ft

House

8872 SW 63RD AVE, OCALA, FL, 34476

Community: Cherrywood

New Marion Landing

6181 SW 84TH PL, OCALA, FL, 34476, Ocala, FL 34476

$235,000

3 beds

2 baths

1,670 sq ft

House

6181 SW 84TH PL, OCALA, FL, 34476

Community: Marion Landing

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

Questions? Call us: (689) 407-5757

New Lake Ashton

5312 NICKLAUS DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884

$334,900

3 beds

2 baths

1,700 sq ft

House

5312 NICKLAUS DR, WINTER HAVEN, FL, 3388...

Community: Lake Ashton

New Stonecrest

17808 SE 115TH CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$349,500

3 beds

3 baths

2,282 sq ft

Villa

17808 SE 115TH CT, SUMMERFIELD, FL, 3449...

Community: Stonecrest

New Sun City Center

1819 NEW BEDFORD DR, SUN CITY CENTER, FL..., Sun City Center, FL 33573

$375,000

3 beds

2 baths

2,555 sq ft

House

1819 NEW BEDFORD DR, SUN CITY CENTER, FL...

Community: Sun City Center

New The Villages®

401 CALHOUN CT, THE VILLAGES, FL, 32162, The Villages, FL 32162

$400,000

3 beds

2 baths

1,663 sq ft

Villa

401 CALHOUN CT, THE VILLAGES, FL, 32162

Community: The Villages®

New Royal Highlands

20618 QUEEN ALEXANDRA DR, LEESBURG, FL, ..., Leesburg, FL 34748

$324,900

3 beds

2 baths

1,945 sq ft

House

20618 QUEEN ALEXANDRA DR, LEESBURG, FL, ...

Community: Royal Highlands

New The Villages®

897 FOLKSTONE WAY, THE VILLAGES, FL, 321..., The Villages, FL 32162

$449,900

3 beds

2 baths

1,939 sq ft

House

897 FOLKSTONE WAY, THE VILLAGES, FL, 321...

Community: The Villages®

New Stone Creek

5897 SW 90TH COURT RD, OCALA, FL, 34481, Ocala, FL 34481

$499,000

2 beds

3 baths

2,287 sq ft

House

5897 SW 90TH COURT RD, OCALA, FL, 34481

Community: Stone Creek

New Royal Harbor

5190 CHINA SEA DR, TAVARES, FL, 32778, Tavares, FL 32778

$300,000

3 beds

2 baths

1,442 sq ft

House

5190 CHINA SEA DR, TAVARES, FL, 32778

Community: Royal Harbor

New Silver Lakes

6257 SILVER LAKES DR, LAKELAND, FL, 3381..., Lakeland, FL 33810

$319,000

2 beds

2 baths

1,759 sq ft

House

6257 SILVER LAKES DR, LAKELAND, FL, 3381...

Community: Silver Lakes

New On Top of the World

8326 SW 82ND CIR, OCALA, FL, 34481, Ocala, FL 34481

$300,000

3 beds

2 baths

1,701 sq ft

House

8326 SW 82ND CIR, OCALA, FL, 34481

Community: On Top of the World

New Trilogy® Orlando

603 CONSERVATION BLVD, GROVELAND, FL, 34..., Groveland, FL 34736

$500,000

2 beds

2 baths

1,918 sq ft

House

603 CONSERVATION BLVD, GROVELAND, FL, 34...

Community: Trilogy® Orlando

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

8526 SW 91ST ST A, OCALA, FL, 34481, Ocala, FL 34481

$159,999

2 beds

2 baths

1,385 sq ft

Villa

8526 SW 91ST ST A, OCALA, FL, 34481

3455 PEGASO AVE, NEW SMYRNA BEACH, FL, 3...

8447 SW 60TH CT, OCALA, FL, 34476

Community: Marion Landing

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

Questions? Call us: (689) 407-5757

New Summer Trees

125 CROOKED PINE RD, PORT ORANGE, FL, 32..., Port Orange, FL 32128

$289,900

2 beds

2 baths

1,180 sq ft

House

125 CROOKED PINE RD, PORT ORANGE, FL, 32...

Community: Summer Trees

New On Top of the World

9722 SW 95TH CT C, OCALA, FL, 34481, Ocala, FL 34481

$159,000

2 beds

2 baths

1,412 sq ft

Villa

9722 SW 95TH CT C, OCALA, FL, 34481

Community: On Top of the World

New Breakaway Trails

38 WINDING CREEK WAY, ORMOND BEACH, FL, ..., Ormond Beach, FL 32174

$999,000

5 beds

5 baths

3,802 sq ft

House

38 WINDING CREEK WAY, ORMOND BEACH, FL, ...

Community: Breakaway Trails

New Valencia Lakes

16239 CAPE CORAL DR, WIMAUMA, FL, 33598, Wimauma, FL 33598

$429,950

3 beds

2 baths

2,049 sq ft

House

16239 CAPE CORAL DR, WIMAUMA, FL, 33598

Community: Valencia Lakes

New On Top of the World

9060 SW 96TH LN B, OCALA, FL, 34481, Ocala, FL 34481

$175,000

2 beds

2 baths

1,521 sq ft

Villa

9060 SW 96TH LN B, OCALA, FL, 34481

Community: On Top of the World

New Stone Creek

6038 SW 86TH CIR, OCALA, FL, 34481, Ocala, FL 34481

$634,436

2 beds

3 baths

2,304 sq ft

House

6038 SW 86TH CIR, OCALA, FL, 34481

Community: Stone Creek

New On Top of the World

8889 SW 96TH ST F, OCALA, FL, 34481, Ocala, FL 34481

$154,900

2 beds

2 baths

1,409 sq ft

Villa

8889 SW 96TH ST F, OCALA, FL, 34481

Community: On Top of the World

New Esplanade at Highland Ranch

1263 ZEEK RIDGE ST, CLERMONT, FL, 34715, Clermont, FL 34715

$595,000

3 beds

3 baths

2,275 sq ft

House

1263 ZEEK RIDGE ST, CLERMONT, FL, 34715

Community: Esplanade at Highland Ranch

New The Villages®

422 SAN MARINO DR, THE VILLAGES, FL, 321..., The Villages, FL 32159

$395,000

3 beds

3 baths

1,652 sq ft

House

422 SAN MARINO DR, THE VILLAGES, FL, 321...

Community: The Villages®

New The Villages®

3468 MCDANIEL PL, THE VILLAGES, FL, 3216..., The Villages, FL 32163

$1,195,000

4 beds

3 baths

3,371 sq ft

House

3468 MCDANIEL PL, THE VILLAGES, FL, 3216...

Community: The Villages®

New On Top of the World

9820 SW 89TH TER E, OCALA, FL, 34481, Ocala, FL 34481

$210,000

2 beds

2 baths

1,748 sq ft

House

9820 SW 89TH TER E, 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

New Spruce Creek South

9377 SE 174TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491

$195,000

2 beds

2 baths

1,154 sq ft

House

9377 SE 174TH LOOP, SUMMERFIELD, FL, 344...

Community: Spruce Creek South

New Marion Landing

8490 SW 60TH CT, OCALA, FL, 34476, Ocala, FL 34476

$274,999

3 beds

2 baths

1,963 sq ft

House

8490 SW 60TH CT, OCALA, FL, 34476

Community: Marion Landing

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.

How long do listings in 55+ communities in Winter Garden typically stay on the market, and what is the average price of homes for sale?

On average, listings in 55+ communities in Winter Garden stay on the market for around 390 days. The average price of homes for sale in these communities is approximately $477,149, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Del Webb Oasis average around $477,149.

Want more information about active adult communities around Winter Garden?

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113 communities

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

113 communities near Winter Garden

3,445 homes near Winter Garden

3 beds

2 baths

1,757 sq ft

House

2 beds

3 baths

1,737 sq ft

Townhouse

2 beds

2 baths

1,351 sq ft

Condo

4 beds

2 baths

2,039 sq ft

House

3 beds

2 baths

1,670 sq ft

House

3 beds

2 baths

1,700 sq ft

House

3 beds

3 baths

2,282 sq ft

Villa

3 beds

2 baths

2,555 sq ft

House

3 beds

2 baths

1,663 sq ft

Villa

3 beds

2 baths

1,945 sq ft

House

3 beds

2 baths

1,939 sq ft

House

2 beds

3 baths

2,287 sq ft

House

3 beds

2 baths

1,442 sq ft

House

2 beds

2 baths

1,759 sq ft

House

3 beds

2 baths

1,701 sq ft

House

2 beds

2 baths

1,918 sq ft

House

2 beds

2 baths

1,385 sq ft

Villa

3 beds

2 baths

1,661 sq ft

House

2 beds

2 baths

1,867 sq ft

Villa

3 beds