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

110 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

4.2 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

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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.

5 rating (3 reviews)

Stonecrest

$200ks - $500ks

Stonecrest, Summerfield, FL

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

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

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

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

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

4.7 rating (11 reviews)

Valencia Lakes

$200ks - $700ks

Valencia Lakes, Wimauma, FL

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

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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

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

Pelican Bay Daytona Beach

$100ks - $600ks

Pelican Bay Daytona Beach, Daytona Beach, FL

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

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

2.8 rating (6 reviews)

Arlington Ridge

$200ks - $500ks

Arlington Ridge, Leesburg, FL

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

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

Mirada

$300ks - $500ks

Mirada, San Antonio, FL

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

2.3 rating (6 reviews)

Cherrywood

$100ks - $800ks

Cherrywood, Ocala, FL

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

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

4.8 rating (6 reviews)

Highland Lakes

$100ks - $200ks

Highland Lakes, Leesburg, FL

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

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 (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

5 rating (8 reviews)

Pennbrooke Fairways

<$100k - $300ks

Pennbrooke Fairways, Leesburg, FL

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

3.8 rating (5 reviews)

Marion Landing

$100ks - $300ks

Marion Landing, Ocala, FL

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

1419 LANGLEY DR, SUN CITY CENTER, FL, 33...

Community: Sun City Center

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 Highland Lakes

6042 WADE ST, LEESBURG, FL, 34748, Leesburg, FL 34748

$325,000

3 beds

2 baths

1,634 sq ft

House

6042 WADE ST, LEESBURG, FL, 34748

Community: Highland Lakes

New The Villages®

1639 EDISTO LN, THE VILLAGES, FL, 32162, The Villages, FL 32162

$314,000

2 beds

2 baths

1,196 sq ft

Villa

1639 EDISTO LN, THE VILLAGES, FL, 32162

Community: The Villages®

New Spruce Creek South

9850 SE 178TH LN, SUMMERFIELD, FL, 34491, Summerfield, FL 34491

$179,000

2 beds

2 baths

1,356 sq ft

House

9850 SE 178TH LN, SUMMERFIELD, FL, 34491

Community: Spruce Creek South

New Latitude Margaritaville

572 LANDSHARK BLVD, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124

$389,000

2 beds

2 baths

1,464 sq ft

House

572 LANDSHARK BLVD, DAYTONA BEACH, FL, 3...

Community: Latitude Margaritaville

New Breakaway Trails

85 SHADOWCREEK WAY, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174

$820,000

5 beds

4 baths

4,420 sq ft

House

85 SHADOWCREEK WAY, ORMOND BEACH, FL, 32...

Community: Breakaway Trails

New Stonecrest

10977 SE 169TH LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$445,000

3 beds

2 baths

2,199 sq ft

House

10977 SE 169TH LN, SUMMERFIELD, FL, 3449...

Community: Stonecrest

New Solivita

213 GRAND CANAL DR, POINCIANA, FL, 34759, Poinciana, FL 34759

$215,000

2 beds

2 baths

1,104 sq ft

House

213 GRAND CANAL DR, POINCIANA, FL, 34759

Community: Solivita

New Ocala Preserve

4583 NW 39TH STREET RD, OCALA, FL, 34482, Ocala, FL 34482

$345,990

4 beds

2 baths

2,034 sq ft

House

4583 NW 39TH STREET RD, OCALA, FL, 34482

Community: Ocala Preserve

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

Questions? Call us: (689) 407-5757

New Ocala Preserve

4015 NW 44TH CIR, OCALA, FL, 34482, Ocala, FL 34482

$263,155

2 beds

2 baths

1,614 sq ft

House

4015 NW 44TH CIR, OCALA, FL, 34482

Community: Ocala Preserve

New Cherrywood

9862 SW 59TH CIR, OCALA, FL, 34476, Ocala, FL 34476

$209,900

2 beds

2 baths

1,320 sq ft

House

9862 SW 59TH CIR, OCALA, FL, 34476

Community: Cherrywood

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

Questions? Call us: (689) 407-5757

New The Villages®

508 SAINT ANDREWS BLVD, THE VILLAGES, FL..., The Villages, FL 32159

$259,500

2 beds

2 baths

1,532 sq ft

Manufactured Home

508 SAINT ANDREWS BLVD, THE VILLAGES, FL...

10799 GABLE DIG LOOP, SAN ANTONIO, FL, 3...

Community: Mirada

New Tohoqua Reserve

1845 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744

$359,900

2 beds

2 baths

1,579 sq ft

House

1845 SPRING SHOWER CIR, KISSIMMEE, FL, 3...

Community: Tohoqua Reserve

New The Villages®

2028 GLENARDEN PATH, THE VILLAGES, FL, 3..., The Villages, FL 32163

$509,900

3 beds

2 baths

1,927 sq ft

House

2028 GLENARDEN PATH, THE VILLAGES, FL, 3...

House

9003 OAKCREST CIR, MOUNT DORA, FL, 32757

Community: The Country Club of Mount Dora

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

Questions? Call us: (689) 407-5757

New Sun City Center

1211 PERIDOT LN, SUN CITY CENTER, FL, 33..., Sun City Center, FL 33573

$485,000

3 beds

2 baths

2,072 sq ft

House

1211 PERIDOT LN, SUN CITY CENTER, FL, 33...

Community: Sun City Center

New Sun City Center

2007 N HALCYON DR 310, SUN CITY CENTER, ..., Sun City Center, FL 33573

$159,900

2 beds

2 baths

1,000 sq ft

Condo

2007 N HALCYON DR 310, SUN CITY CENTER, ...

Community: Sun City Center

New Del Webb Orlando

192 MONTORO LN, DAVENPORT, FL, 33837, Davenport, FL 33837

$429,900

2 beds

2 baths

2,168 sq ft

House

192 MONTORO LN, DAVENPORT, FL, 33837

Community: Del Webb Orlando

New Valencia Lakes

16015 CAPE CORAL DR, WIMAUMA, FL, 33598, Wimauma, FL 33598

$883,500

3 beds

3 baths

3,302 sq ft

House

16015 CAPE CORAL DR, WIMAUMA, FL, 33598

Community: Valencia Lakes

New Sun City Center

401 DE GRASSE PL 18, SUN CITY CENTER, FL..., Sun City Center, FL 33573

$99,900

1 beds

2 baths

992 sq ft

Condo

401 DE GRASSE PL 18, SUN CITY CENTER, FL...

Community: Sun City Center

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

8145 SW 108 ST, OCALA, FL, 34481

Community: Oak Run

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

Questions? Call us: (689) 407-5757

New Lakes at Laurel Highlands

2162 BLUE HIGHLANDS DR, LAKELAND, FL, 33..., Lakeland, FL 33811

$309,900

3 beds

2 baths

1,784 sq ft

House

2162 BLUE HIGHLANDS DR, LAKELAND, FL, 33...

Community: Lakes at Laurel Highlands

New Highland Lakes

27110 RACQUET CIR, LEESBURG, FL, 34748, Leesburg, FL 34748

$269,000

3 beds

2 baths

1,531 sq ft

House

27110 RACQUET CIR, LEESBURG, FL, 34748

Community: Highland Lakes

New Spruce Creek South

17981 SE 106TH CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$175,900

2 beds

1 baths

792 sq ft

House

17981 SE 106TH CT, SUMMERFIELD, FL, 3449...

Community: Spruce Creek South

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

Questions? Call us: (689) 407-5757

New The Villages®

3252 PALATINE CT, THE VILLAGES, FL, 3216..., The Villages, FL 32162

$380,000

3 beds

2 baths

1,647 sq ft

House

3252 PALATINE CT, THE VILLAGES, FL, 3216...

Community: The Villages®

New Sun City Center

405 BLACKHAWK CIR, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573

$399,900

2 beds

2 baths

2,135 sq ft

House

405 BLACKHAWK CIR, SUN CITY CENTER, FL, ...

Community: Sun City Center

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?

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110 communities

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

110 communities near Winter Garden

3,664 homes near Winter Garden

3 beds

2 baths

2,591 sq ft

House

3 beds

2 baths

1,573 sq ft

House

2 beds

2 baths

1,406 sq ft

House

2 beds

2 baths

1,467 sq ft

House

2 beds

2 baths

1,529 sq ft

Villa

3 beds

2 baths

1,634 sq ft

House

2 beds

2 baths

1,196 sq ft

Villa

2 beds

2 baths

1,356 sq ft

House

2 beds

2 baths

1,464 sq ft

House

5 beds

4 baths

4,420 sq ft

House

3 beds

2 baths

2,199 sq ft

House

2 beds

2 baths

1,104 sq ft

House

4 beds

2 baths

2,034 sq ft

House

2 beds

2 baths

1,614 sq ft

House

2 beds

2 baths

1,320 sq ft

House

2 beds

2 baths

1,532 sq ft

Manufactured Home

2 beds

2 baths

1,035 sq ft

Villa

2 beds

2 baths

1,540 sq ft

House

2 beds

3 baths

1,747 sq ft

Villa

2 beds