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

3,584 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

<$100k - $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

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

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

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

$300Ks - $600Ks

Trilogy® Orlando, Groveland, FL

Resale Only | 55+ age-restricted | Built 2005 - 2022 | 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)

VillageWalk at Lake Nona

$400Ks - $900Ks

VillageWalk at Lake Nona, Orlando, FL

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

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

12333 WOODLANDS CIR, DADE CITY, FL, 3352...

Community: Lake Jovita Golf and Country Club

Latitude Margaritaville

418 GOOD LIFE WAY, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32124

$599,900

3 beds

3 baths

2,067 sq ft

House

418 GOOD LIFE WAY, DAYTONA BEACH, FL, 32...

Community: Latitude Margaritaville

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

Questions? Call us: (689) 407-5757

Windermere

820 INVERIE DR, INVERNESS, FL, 34453, Inverness, FL 34453

$200,000

2 beds

2 baths

1,286 sq ft

House

820 INVERIE DR, INVERNESS, FL, 34453

Community: Windermere

Royal Harbor

3001 LAKE HURON LN, TAVARES, FL, 32778, Tavares, FL 32778

$359,900

3 beds

2 baths

1,920 sq ft

House

3001 LAKE HURON LN, TAVARES, FL, 32778

Community: Royal Harbor

The Villages®

$319,900

2 beds

2 baths

1,196 sq ft

Villa

1410 NATALIE LN, THE VILLAGES, FL, 32162

Community: The Villages®

Pine Run Estates

10078 SW 87TH TER, OCALA, FL, 34481, Ocala, FL 34481

$167,000

2 beds

2 baths

1,144 sq ft

House

10078 SW 87TH TER, OCALA, FL, 34481

Community: Pine Run Estates

Cherrywood

15090 SW 63RD COURT RD, OCALA, FL, 34473, Ocala, FL 34473

$303,900

4 beds

3 baths

1,679 sq ft

House

15090 SW 63RD COURT RD, OCALA, FL, 34473

Community: Cherrywood

Lakeside Landings

5007 BELTED KINGFISHER DR, OXFORD, FL, 3..., Oxford, FL 34484

$400,000

3 beds

2 baths

2,352 sq ft

House

5007 BELTED KINGFISHER DR, OXFORD, FL, 3...

Community: Lakeside Landings

Oak Run

11716 SW 72ND CIR, OCALA, FL, 34476, Ocala, FL 34476

$329,000

3 beds

2 baths

2,067 sq ft

House

11716 SW 72ND CIR, OCALA, FL, 34476

Community: Oak Run

Legacy of Leesburg

5318 FANTASY WAY, LEESBURG, FL, 34748, Leesburg, FL 34748

$374,000

3 beds

2 baths

2,182 sq ft

House

5318 FANTASY WAY, LEESBURG, FL, 34748

Community: Legacy of Leesburg

Valencia Lakes

4946 SAPPHIRE SOUND DR, WIMAUMA, FL, 335..., Wimauma, FL 33598

$449,800

3 beds

2 baths

2,194 sq ft

House

4946 SAPPHIRE SOUND DR, WIMAUMA, FL, 335...

Community: Valencia Lakes

High Vista at Ridgewood Lakes

221 PRATHER DR, DAVENPORT, FL, 33837, Davenport, FL 33837

$249,000

2 beds

2 baths

1,435 sq ft

House

221 PRATHER DR, DAVENPORT, FL, 33837

Community: High Vista at Ridgewood Lakes

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

Questions? Call us: (689) 407-5757

Lakes of Mount Dora

8780 BRIDGEPORT BAY CIR, MOUNT DORA, FL,..., Mount Dora, FL 32757

$489,000

3 beds

2 baths

1,682 sq ft

House

8780 BRIDGEPORT BAY CIR, MOUNT DORA, FL,...

Community: Lakes of Mount Dora

Pennbrooke Fairways

32521 W GOLF CT, LEESBURG, FL, 34748, Leesburg, FL 34748

$114,247

2 beds

1 baths

936 sq ft

Manufactured Home

32521 W GOLF CT, LEESBURG, FL, 34748

Community: Pennbrooke Fairways

Traditions at Lake Ruby

2925 DAYTON DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884

$334,900

3 beds

2 baths

2,109 sq ft

House

2925 DAYTON DR, WINTER HAVEN, FL, 33884

Community: Traditions at Lake Ruby

Plantation at Leesburg

5062 EL DESTINO DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$264,000

3 beds

2 baths

1,021 sq ft

House

5062 EL DESTINO DR, LEESBURG, FL, 34748

Community: Plantation at Leesburg

The Villages®

$293,000

2 beds

2 baths

1,156 sq ft

House

971 MARGAUX TRL, THE VILLAGES, FL, 32162

Community: The Villages®

Solivita

1388 LOMBARDI CT, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$289,000

2 beds

2 baths

1,366 sq ft

House

1388 LOMBARDI CT, KISSIMMEE, FL, 34759

Community: Solivita

Lakes of Mount Dora

2440 PAWTUCKET PASS, MOUNT DORA, FL, 327..., Mount Dora, FL 32757

$624,900

2 beds

2 baths

2,663 sq ft

House

2440 PAWTUCKET PASS, MOUNT DORA, FL, 327...

Community: Lakes of Mount Dora

The Villages®

$587,654

3 beds

2 baths

1,484 sq ft

Villa

2823 CADE CT, THE VILLAGES, FL, 32163

Community: The Villages®

Carillon Lakes

3213 BELLFLOWER WAY, LAKELAND, FL, 33811, Lakeland, FL 33811

$309,000

3 beds

2 baths

1,846 sq ft

House

3213 BELLFLOWER WAY, LAKELAND, FL, 33811

Community: Carillon Lakes

Sun City Center

$250,000

2 beds

2 baths

1,860 sq ft

House

1209 WILD FEATHER LN, SUN CITY CENTER, F...

Community: Sun City Center

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

Questions? Call us: (689) 407-5757

Lakes at Laurel Highlands

2062 BLUE HIGHLANDS DR, LAKELAND, FL, 33..., Lakeland, FL 33811

$385,000

5 beds

3 baths

2,696 sq ft

House

2062 BLUE HIGHLANDS DR, LAKELAND, FL, 33...

Community: Lakes at Laurel Highlands

On Top of the World

8830 SW 98TH PL L, OCALA, FL, 34481, Ocala, FL 34481

$182,000

2 beds

3 baths

1,764 sq ft

Townhouse

8830 SW 98TH PL L, OCALA, FL, 34481

Community: On Top of the World

Spruce Creek Country Club

11703 SE 91ST CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$437,900

3 beds

2 baths

2,278 sq ft

House

11703 SE 91ST CIR, SUMMERFIELD, FL, 3449...

Community: Spruce Creek Country Club

Royal Highlands

4738 ST ANDREWS ARC, LEESBURG, FL, 34748, Leesburg, FL 34748

$305,000

3 beds

2 baths

1,892 sq ft

House

4738 ST ANDREWS ARC, LEESBURG, FL, 34748

Community: Royal Highlands

On Top of the World

8883 SW 85TH LOOP, OCALA, FL, 34481, Ocala, FL 34481

$614,999

3 beds

3 baths

2,216 sq ft

House

8883 SW 85TH LOOP, OCALA, FL, 34481

Community: On Top of the World

Huntington at Hunter's Ridge

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

$338,900

3 beds

2 baths

1,523 sq ft

House

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

Community: Huntington at Hunter's Ridge

SummerGlen

16193 SW 14TH AVENUE RD, OCALA, FL, 3447..., Ocala, FL 34473

$284,900

3 beds

2 baths

1,647 sq ft

House

16193 SW 14TH AVENUE RD, OCALA, FL, 3447...

Community: SummerGlen

Royal Harbor

4920 PORTSMOUTH ST, TAVARES, FL, 32778, Tavares, FL 32778

$314,900

3 beds

2 baths

1,471 sq ft

House

4920 PORTSMOUTH ST, TAVARES, FL, 32778

Community: Royal Harbor

Spruce Creek North

6468 SW 107TH PL, OCALA, FL, 34476, Ocala, FL 34476

$185,000

2 beds

2 baths

1,095 sq ft

House

6468 SW 107TH PL, OCALA, FL, 34476

Community: Spruce Creek North

Carlsberg Estates on Lake Suzanne

231 LAKE SUZANNE DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859

$259,900

2 beds

2 baths

1,406 sq ft

House

231 LAKE SUZANNE DR, LAKE WALES, FL, 338...

House

4929 NW 35TH LANE RD, OCALA, FL, 34482

Community: Ocala Preserve

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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?

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3,584 homes near Winter Garden

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

106 communities near Winter Garden

3,584 homes near Winter Garden

3 beds

2 baths

1,615 sq ft

House

2 beds

2 baths

1,533 sq ft

House

3 beds

2 baths

1,704 sq ft

House

3 beds

3 baths

2,292 sq ft

House

3 beds

3 baths

2,067 sq ft

House

2 beds

2 baths

1,286 sq ft

House

3 beds

2 baths

1,920 sq ft

House

2 beds

2 baths

1,196 sq ft

Villa

2 beds

2 baths

1,144 sq ft

House

4 beds

3 baths

1,679 sq ft

House

3 beds

2 baths

2,352 sq ft

House

3 beds

2 baths

2,067 sq ft

House

3 beds

2 baths

2,182 sq ft

House

3 beds

2 baths

2,194 sq ft

House

2 beds

2 baths

1,435 sq ft

House

3 beds

2 baths

1,682 sq ft

House

2 beds

1 baths

936 sq ft

Manufactured Home

3 beds

2 baths

2,109 sq ft

House

3 beds

2 baths

1,021 sq ft

House

2 beds