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

3,573 homes near Winter Garden

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Del Webb Oasis

$400Ks - $1Ms

Del Webb Oasis, Winter Garden, FL

New Construction | 55+ age-restricted | Built 2020 - present | 422 homes

4 rating (17 reviews)

The Villages®

<$100k - $2Ms

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

<$100k - $600Ks

Sun City Center, Sun City Center, FL

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

4.7 rating (18 reviews)

Solivita

$100Ks - $700Ks

Solivita, Kissimmee, FL

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

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Questions? Call us: (689) 407-5757

3.6 rating (46 reviews)

Latitude Margaritaville

$300Ks - $700Ks

Latitude Margaritaville, Daytona Beach, FL

Resale Only | 55+ age-restricted | Built 2017 - 2025 | 3,900 homes

4.2 rating (10 reviews)

Stone Creek

$200Ks - $800Ks

Stone Creek, Ocala, FL

New and Resale | 55+ age-restricted | Built 2006 - present | 3,800 homes

4.1 rating (29 reviews)

Oak Run

$100Ks - $500Ks

Oak Run, Ocala, FL

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

4.5 rating (11 reviews)

Spruce Creek Country Club

$200Ks - $500Ks

Spruce Creek Country Club, Summerfield, FL

Resale Only | 55+ age-restricted | Built 1996 - 2007 | 3,250 homes

5 rating (2 reviews)

Plantation at Leesburg

$100Ks - $400Ks

Plantation at Leesburg, Leesburg, FL

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

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 (3 reviews)

Twin Lakes

$200Ks - $900Ks

Twin Lakes, St. Cloud, FL

New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes

No reviews yet

Pelican Bay Daytona Beach

$100Ks - $500Ks

Pelican Bay Daytona Beach, Daytona Beach, FL

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

4.6 rating (5 reviews)

Ocala Preserve

$200Ks - $600Ks

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

4.7 rating (3 reviews)

Spruce Creek South

$100Ks - $300Ks

Spruce Creek South, Summerfield, FL

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

4.7 rating (11 reviews)

Valencia Lakes

$200Ks - $900Ks

Valencia Lakes, Wimauma, FL

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

5 rating (1 reviews)

Cypress Lakes

$200Ks - $200Ks

Cypress Lakes, Lakeland, FL

Resale Only | 55+ age-restricted | Built 1987 - 2016 | 1,604 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

No reviews yet

Venetian Bay

$200Ks - $1Ms

Venetian Bay, New Smyrna Beach, FL

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

3.8 rating (6 reviews)

Trilogy® Orlando

$300Ks - $600Ks

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

3.8 rating (6 reviews)

Tampa Bay Golf and Countr...

$200Ks - $400Ks

Tampa Bay Golf and Countr..., San Antonio, FL

Resale Only | 55+ age-restricted | Built 1994 - 2015 | 1,336 homes

5 rating (1 reviews)

Del Webb Sunbridge

$300Ks - $1Ms

Del Webb Sunbridge, St. Cloud, FL

New and Resale | 55+ age-restricted | Built 2019 - present | 1,300 homes

5 rating (1 reviews)

VillageWalk at Lake Nona

$400Ks - $900Ks

VillageWalk at Lake Nona, Orlando, FL

Resale Only | Age-targeted | Built 2006 - 2016 | 1,300 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

$100Ks - $300Ks

Pennbrooke Fairways, Leesburg, FL

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

5 rating (1 reviews)

Sandpiper Golf & Coun...

$200Ks - $300Ks

Sandpiper Golf & Coun..., Lakeland, FL

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

3.6 rating (5 reviews)

Heritage Hills

$200Ks - $500Ks

Heritage Hills, Clermont, FL

New and Resale | 55+ age-restricted | Built 2006 - present | 1,154 homes

5 rating (1 reviews)

Ocala Palms

$100Ks - $400Ks

Ocala Palms, Ocala, FL

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

5 rating (1 reviews)

Cresswind at Victoria Gar...

$300Ks - $600Ks

Cresswind at Victoria Gar..., DeLand, FL

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

5 rating (5 reviews)

SummerGlen

$200Ks - $400Ks

SummerGlen, Ocala, FL

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

5 rating (1 reviews)

Legacy of Leesburg

$200Ks - $400Ks

Legacy of Leesburg, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1999 - 2017 | 1,000 homes

No reviews yet

Breakaway Trails

$300Ks - $1Ms

Breakaway Trails, Ormond Beach, FL

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

4 rating (4 reviews)

Lakes of Mount Dora

$400Ks - $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

$200Ks - $1Ms

Harbor Hills Country Club, Lady Lake, FL

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

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

Questions? Call us: (689) 407-5757

4.8 rating (6 reviews)

Highland Lakes

$200Ks - $300Ks

Highland Lakes, Leesburg, FL

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

4.3 rating (15 reviews)

Del Webb Orlando

$200Ks - $400Ks

Del Webb Orlando, Davenport, FL

Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes

No reviews yet

Pine Run Estates

<$100k - $400Ks

Pine Run Estates, Ocala, FL

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

No reviews yet

Lake Jovita Golf and Coun...

$300Ks - $1Ms

Lake Jovita Golf and Coun..., Dade City, FL

New and Resale | Age-targeted | Built 1999 - present | 875 homes

No reviews yet

Esplanade at Wiregrass Ra...

$400Ks - $1Ms

Esplanade at Wiregrass Ra..., Wesley Chapel, FL

New and Resale | 55+ age-restricted | Built 2019 - present | 868 homes

1 2...3

The Villages®

$355,000

3 beds

2 baths

1,715 sq ft

House

2265 HACKNEY WAY, THE VILLAGES, FL, 3216...

Community: The Villages®

Quail Meadow

4941 NW 32ND ST, OCALA, FL, 34482, Ocala, FL 34482

$355,000

4 beds

3 baths

2,443 sq ft

House

4941 NW 32ND ST, OCALA, FL, 34482

Community: Quail Meadow

Tampa Bay Golf and Country Club

10833 COLLAR DR, SAN ANTONIO, FL, 33576, San Antonio, FL 33576

$299,900

3 beds

2 baths

1,601 sq ft

House

10833 COLLAR DR, SAN ANTONIO, FL, 33576

Community: Tampa Bay Golf and Country Club

Sun City Center

$150,000

2 beds

2 baths

1,078 sq ft

Condo

316 KELSEY WAY # 316, SUN CITY CENTER, F...

Community: Sun City Center

Foxwood Lake Estates

5006 LODGEWOOD DR, LAKELAND, FL, 33810, Lakeland, FL 33810

$189,900

2 beds

2 baths

1,104 sq ft

Manufactured Home

5006 LODGEWOOD 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

Huntington at Hunter's Ridge

14 FAWN HAVEN TRL, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174

$439,000

3 beds

2 baths

2,001 sq ft

House

14 FAWN HAVEN TRL, ORMOND BEACH, FL, 321...

Community: Huntington at Hunter's Ridge

Lake Ashton

1142 SAWGRASS DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884

$489,900

3 beds

2 baths

2,057 sq ft

House

1142 SAWGRASS DR, WINTER HAVEN, FL, 3388...

Community: Lake Ashton

Solivita

204 BELLA CORTINA DR, KISSIMMEE, FL, 347..., Kissimmee, FL 34759

$380,000

3 beds

2 baths

1,816 sq ft

House

204 BELLA CORTINA DR, KISSIMMEE, FL, 347...

Community: Solivita

Oak Run

11427 SW 82ND AVE, OCALA, FL, 34481, Ocala, FL 34481

$300,000

3 beds

4 baths

2,074 sq ft

House

11427 SW 82ND AVE, OCALA, FL, 34481

Community: Oak Run

Spring Lake Towers

700 MIRROR TER 403, WINTER HAVEN, FL, 33..., Winter Haven, FL 33881

$164,500

2 beds

2 baths

1,190 sq ft

Condo

700 MIRROR TER 403, WINTER HAVEN, FL, 33...

Community: Spring Lake Towers

Lake James

$495,900

3 beds

2 baths

1,886 sq ft

House

7895 LAKE JAMES BLVD, LAKELAND, FL, 3381...

Community: Lake James

Solivita

542 VITERRA CT, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$463,000

3 beds

3 baths

2,312 sq ft

House

542 VITERRA CT, KISSIMMEE, FL, 34759

Community: Solivita

Ocala Preserve

4056 NW 44TH CIR, OCALA, FL, 34482, Ocala, FL 34482

$279,990

2 beds

2 baths

1,614 sq ft

House

4056 NW 44TH CIR, OCALA, FL, 34482

Community: Ocala Preserve

Latitude Margaritaville

913 BAMA BREEZE DR, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124

$489,500

2 beds

2 baths

1,558 sq ft

House

913 BAMA BREEZE DR, DAYTONA BEACH, FL, 3...

Community: Latitude Margaritaville

Arlington Ridge

$389,900

4 beds

2 baths

1,857 sq ft

House

4110 ARLINGTON RIDGE BLVD, LEESBURG, FL,...

Community: Arlington Ridge

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

Questions? Call us: (689) 407-5757

Gatherings of Lake Nona

7557 LAUREATE BLVD UNIT 6301, ORLANDO, F..., Orlando, FL 32827

$354,990

2 beds

2 baths

1,368 sq ft

Condo

7557 LAUREATE BLVD UNIT 6301, ORLANDO, F...

Community: Gatherings of Lake Nona

Gatherings of Lake Nona

7557 LAUREATE BLVD UNIT 6208, ORLANDO, F..., Orlando, FL 32827

$365,300

2 beds

2 baths

1,445 sq ft

Condo

7557 LAUREATE BLVD UNIT 6208, ORLANDO, F...

Community: Gatherings of Lake Nona

Gatherings of Lake Nona

7545 LAUREATE BLVD UNIT 7203, ORLANDO, F..., Orlando, FL 32827

$450,265

2 beds

2 baths

1,549 sq ft

Condo

7545 LAUREATE BLVD UNIT 7203, ORLANDO, F...

Community: Gatherings of Lake Nona

Gatherings of Lake Nona

7545 LAUREATE BLVD UNIT 7202, ORLANDO, F..., Orlando, FL 32827

$484,160

3 beds

2 baths

1,805 sq ft

Condo

7545 LAUREATE BLVD UNIT 7202, ORLANDO, F...

Community: Gatherings of Lake Nona

Pelican Bay Daytona Beach

164 KINGBIRD CIR, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32119

$259,900

2 beds

2 baths

1,295 sq ft

Townhouse

164 KINGBIRD CIR, DAYTONA BEACH, FL, 321...

Community: Pelican Bay Daytona Beach

Tampa Bay Golf and Country Club

29312 MARKER LOOP, SAN ANTONIO, FL, 3357..., San Antonio, FL 33576

$325,000

3 beds

2 baths

1,596 sq ft

Villa

29312 MARKER LOOP, SAN ANTONIO, FL, 3357...

Community: Tampa Bay Golf and Country Club

Twin Lakes

2780 SOUTHLAND ST, SAINT CLOUD, FL, 3477..., Saint Cloud, FL 34772

$520,000

3 beds

3 baths

2,208 sq ft

House

2780 SOUTHLAND ST, SAINT CLOUD, FL, 3477...

Community: Twin Lakes

On Top of the World

8731 SW 76TH STREET RD, OCALA, FL, 34481, Ocala, FL 34481

$414,900

3 beds

2 baths

2,118 sq ft

House

8731 SW 76TH STREET RD, OCALA, FL, 34481

Community: On Top of the World

Pine Run Estates

10028 SW 88TH CT, OCALA, FL, 34481, Ocala, FL 34481

$159,900

2 beds

2 baths

1,024 sq ft

House

10028 SW 88TH CT, OCALA, FL, 34481

Community: Pine Run Estates

Traditions at Lake Ruby

3934 BEDFORD AVE, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884

$459,900

4 beds

3 baths

2,312 sq ft

House

3934 BEDFORD AVE, WINTER HAVEN, FL, 3388...

Community: Traditions at Lake Ruby

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

Questions? Call us: (689) 407-5757

Stone Creek

6832 SW 93RD AVE, OCALA, FL, 34481, Ocala, FL 34481

$374,900

3 beds

2 baths

1,714 sq ft

House

6832 SW 93RD AVE, OCALA, FL, 34481

Community: Stone Creek

Cresswind at Victoria Gardens

1079 LINCOLNSHIRE DR, DELAND, FL, 32724, Deland, FL 32724

$389,900

2 beds

2 baths

1,651 sq ft

House

1079 LINCOLNSHIRE DR, DELAND, FL, 32724

Community: Cresswind at Victoria Gardens

The Villages®

$559,000

3 beds

2 baths

1,927 sq ft

House

3750 RASPBERRY CT, THE VILLAGES, FL, 321...

Community: The Villages®

Sun City Center

$299,900

3 beds

2 baths

1,573 sq ft

House

2325 W DEL WEBB BLVD, SUN CITY CENTER, F...

Community: Sun City Center

On Top of the World

9490 SW 85TH AVE E, OCALA, FL, 34481, Ocala, FL 34481

$189,500

2 beds

2 baths

1,389 sq ft

Villa

9490 SW 85TH AVE E, OCALA, FL, 34481

Community: On Top of the World

Oak Run

10989 SW 86TH AVE, OCALA, FL, 34481, Ocala, FL 34481

$199,000

2 beds

2 baths

1,656 sq ft

House

10989 SW 86TH AVE, OCALA, FL, 34481

Community: Oak Run

Plantation at Leesburg

25274 LOST OAK CIR, LEESBURG, FL, 34748, Leesburg, FL 34748

$317,000

2 beds

2 baths

1,980 sq ft

House

25274 LOST OAK CIR, LEESBURG, FL, 34748

Community: Plantation at Leesburg

Sun City Center

$369,900

2 beds

2 baths

1,943 sq ft

House

335 SIENA VISTA PL, SUN CITY CENTER, FL,...

Community: Sun City Center

Stone Creek

6984 SW 94TH CT, OCALA, FL, 34481, Ocala, FL 34481

$449,921

3 beds

2 baths

1,736 sq ft

House

6984 SW 94TH CT, OCALA, FL, 34481

Community: Stone Creek

On Top of the World

8706 SW 88TH PL, OCALA, FL, 34481, Ocala, FL 34481

$379,900

3 beds

3 baths

1,878 sq ft

House

8706 SW 88TH PL, 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

Latitude Margaritaville

206 ST SOMEWHERE DR, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124

$490,000

2 beds

2 baths

1,606 sq ft

Villa

206 ST SOMEWHERE DR, DAYTONA BEACH, FL, ...

Community: Latitude Margaritaville

Latitude Margaritaville

1078 CASTAWAY CT, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124

$699,900

2 beds

3 baths

2,080 sq ft

House

1078 CASTAWAY CT, DAYTONA BEACH, FL, 321...

Community: Latitude Margaritaville

Venetian Bay

2939 BELLA FLORE TER, NEW SMYRNA BEACH, ..., New Smyrna Beach, FL 32168

$799,000

4 beds

2 baths

2,184 sq ft

House

2939 BELLA FLORE TER, NEW SMYRNA BEACH, ...

Community: Venetian Bay

The Villages®

$359,900

3 beds

2 baths

1,488 sq ft

House

1874 KYRLE TER, THE VILLAGES, FL, 32162

Community: The Villages®

The Villages®

$499,000

3 beds

3 baths

2,158 sq ft

House

1429 BLUEBEARD CT, THE VILLAGES, FL, 321...

Community: The Villages®

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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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Want to learn more about 55+ communities in Winter Garden?

Call us: (689) 407-5757

3,573 homes near Winter Garden

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

106 communities near Winter Garden

3,573 homes near Winter Garden

3 beds

2 baths

1,715 sq ft

House

4 beds

3 baths

2,443 sq ft

House

3 beds

2 baths

1,601 sq ft

House

2 beds

2 baths

1,078 sq ft

Condo

2 beds

2 baths

1,104 sq ft

Manufactured Home

3 beds

2 baths

2,001 sq ft

House

3 beds

2 baths

2,057 sq ft

House

3 beds

2 baths

1,816 sq ft

House

3 beds

4 baths

2,074 sq ft

House

2 beds

2 baths

1,190 sq ft

Condo

3 beds

2 baths

1,886 sq ft

House

3 beds

3 baths

2,312 sq ft

House

2 beds

2 baths

1,614 sq ft

House

2 beds

2 baths

1,558 sq ft

House

4 beds

2 baths

1,857 sq ft

House

2 beds

2 baths

1,368 sq ft

Condo

2 beds

2 baths

1,445 sq ft

Condo

2 beds

2 baths

1,549 sq ft

Condo

3 beds

2 baths

1,805 sq ft

Condo

2 beds