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

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

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

On Top of the World

8450 SW 90TH ST D, OCALA, FL, 34481, Ocala, FL 34481

$162,900

2 beds

2 baths

1,696 sq ft

Villa

8450 SW 90TH ST D, OCALA, FL, 34481

Community: On Top of the World

Sun City Center

$145,000

1 beds

1 baths

834 sq ft

House

1510 COUNCIL DR, SUN CITY CENTER, FL, 33...

Community: Sun City Center

On Top of the World

9566 SW 90TH ST, OCALA, FL, 34481, Ocala, FL 34481

$264,900

2 beds

2 baths

1,696 sq ft

House

9566 SW 90TH ST, OCALA, FL, 34481

Community: On Top of the World

Lake James

$499,900

3 beds

2 baths

1,886 sq ft

House

7919 LAKE JAMES BLVD, LAKELAND, FL, 3381...

Community: Lake James

The Villages®

113 N TIMBER TRL, WILDWOOD, FL, 34785, Wildwood, FL 34785

$125,000

2 beds

2 baths

1,440 sq ft

Mobile Home

113 N TIMBER TRL, WILDWOOD, FL, 34785

Community: The Villages®

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

Questions? Call us: (689) 407-5757

On Top of the World

8433 SW 98TH TERRACE RD, OCALA, FL, 3448..., Ocala, FL 34481

$574,000

3 beds

3 baths

2,373 sq ft

House

8433 SW 98TH TERRACE RD, OCALA, FL, 3448...

Community: On Top of the World

Sun City Center

$254,000

2 beds

2 baths

1,226 sq ft

House

1529 ALLEGHENY DR, SUN CITY CENTER, FL, ...

Community: Sun City Center

The Villages®

$339,000

2 beds

2 baths

1,278 sq ft

Villa

3105 CARROLLTON CT, THE VILLAGES, FL, 32...

Community: The Villages®

Trilogy® Orlando

100 FLAME VINE WAY, GROVELAND, FL, 34736, Groveland, FL 34736

$350,000

2 beds

2 baths

1,808 sq ft

House

100 FLAME VINE WAY, GROVELAND, FL, 34736

Community: Trilogy® Orlando

Ocala Palms

2699 NW 58TH TER, OCALA, FL, 34482, Ocala, FL 34482

$399,000

3 beds

2 baths

2,272 sq ft

House

2699 NW 58TH TER, OCALA, FL, 34482

Community: Ocala Palms

The Villages®

1117 PARADISE DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$195,000

2 beds

2 baths

1,383 sq ft

Manufactured Home

1117 PARADISE DR, LADY LAKE, FL, 32159

Community: The Villages®

The Villages®

926 CHULA CT, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$269,000

2 beds

2 baths

1,383 sq ft

House

926 CHULA CT, LADY LAKE, FL, 32159

Community: The Villages®

Spruce Creek Preserve

11395 SW 139TH ST, DUNNELLON, FL, 34432, Dunnellon, FL 34432

$267,395

3 beds

2 baths

1,724 sq ft

House

11395 SW 139TH ST, DUNNELLON, FL, 34432

Community: Spruce Creek Preserve

Foxwood Lake Estates

5015 FOX CLIFF DR, LAKELAND, FL, 33810, Lakeland, FL 33810

$199,000

2 beds

2 baths

1,612 sq ft

Manufactured Home

5015 FOX CLIFF DR, LAKELAND, FL, 33810

Community: Foxwood Lake Estates

Solivita

233 MONTEREY ST, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$344,900

3 beds

2 baths

1,827 sq ft

House

233 MONTEREY ST, KISSIMMEE, FL, 34759

Community: Solivita

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

Questions? Call us: (689) 407-5757

Summit Greens

2495 SQUAW CRK, CLERMONT, FL, 34711, Clermont, FL 34711

$599,000

3 beds

3 baths

2,817 sq ft

House

2495 SQUAW CRK, CLERMONT, FL, 34711

Community: Summit Greens

Sun City Center

$264,990

2 beds

2 baths

1,756 sq ft

Villa

810 BLUEWATER DR, SUN CITY CENTER, FL, 3...

Community: Sun City Center

On Top of the World

9577 SW 82ND STREET RD, OCALA, FL, 34481, Ocala, FL 34481

$625,800

3 beds

3 baths

2,171 sq ft

House

9577 SW 82ND STREET RD, OCALA, FL, 34481

Community: On Top of the World

The Villages®

$282,000

2 beds

2 baths

1,234 sq ft

House

3817 MIRAGALIA LN, THE VILLAGES, FL, 321...

Community: The Villages®

Oak Run

8596 SW 108TH PLACE RD, OCALA, FL, 34481, Ocala, FL 34481

$300,000

3 beds

2 baths

1,710 sq ft

House

8596 SW 108TH PLACE RD, OCALA, FL, 34481

Community: Oak Run

Plantation at Leesburg

25007 BELLEVUE, LEESBURG, FL, 34748, Leesburg, FL 34748

$238,000

2 beds

2 baths

1,352 sq ft

Manufactured Home

25007 BELLEVUE, LEESBURG, FL, 34748

Community: Plantation at Leesburg

Majestic Oaks Ocala

8120 SW 56TH TER, OCALA, FL, 34476, Ocala, FL 34476

$334,999

3 beds

2 baths

1,843 sq ft

House

8120 SW 56TH TER, OCALA, FL, 34476

Community: Majestic Oaks Ocala

Del Webb Orlando

341 NAVARRA LN, DAVENPORT, FL, 33837, Davenport, FL 33837

$495,000

3 beds

3 baths

2,126 sq ft

House

341 NAVARRA LN, DAVENPORT, FL, 33837

Community: Del Webb Orlando

The Villages®

$500,000

3 beds

2 baths

1,918 sq ft

House

1723 TOWNSEND TER, THE VILLAGES, FL, 321...

Community: The Villages®

Oak Run

8675 SW 108TH ST, OCALA, FL, 34481, Ocala, FL 34481

$260,000

3 beds

2 baths

1,611 sq ft

House

8675 SW 108TH ST, OCALA, FL, 34481

Community: Oak Run

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

Questions? Call us: (689) 407-5757

The Villages®

$409,800

3 beds

2 baths

1,850 sq ft

House

16672 SE 78TH LIVE OAK AVE, THE VILLAGES...

Community: The Villages®

Mirada

31530 MAGNA GULF LOOP, SAN ANTONIO, FL, ..., San Antonio, FL 33576

$325,000

2 beds

2 baths

1,625 sq ft

Villa

31530 MAGNA GULF LOOP, SAN ANTONIO, FL, ...

Community: Mirada

Sun City Center

$190,000

3 beds

2 baths

1,236 sq ft

House

203 RICKENBACKER DR, SUN CITY CENTER, FL...

Community: Sun City Center

The Villages®

$695,000

3 beds

2 baths

1,914 sq ft

House

506 DEAUVILLE CT, THE VILLAGES, FL, 3216...

Community: The Villages®

Stonecrest

11095 SE 175TH PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$295,000

2 beds

2 baths

1,647 sq ft

House

11095 SE 175TH PL, SUMMERFIELD, FL, 3449...

Community: Stonecrest

Highlands Ridge

3556 E GLEN EAGLES DR, AVON PARK, FL, 33..., Avon Park, FL 33825

$449,570

2 beds

2 baths

2,505 sq ft

House

3556 E GLEN EAGLES DR, AVON PARK, FL, 33...

Community: Highlands Ridge

Baytree

2512 BAYWATER RD, TAVARES, FL, 32778, Tavares, FL 32778

$560,000

3 beds

2 baths

1,980 sq ft

House

2512 BAYWATER RD, TAVARES, FL, 32778

Community: Baytree

Solivita

3390 FALLBROOK DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$288,000

2 beds

2 baths

1,353 sq ft

Villa

3390 FALLBROOK DR, KISSIMMEE, FL, 34759

Community: Solivita

Solivita

265 ANASTASIA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$359,900

3 beds

2 baths

2,068 sq ft

House

265 ANASTASIA DR, KISSIMMEE, FL, 34759

Community: Solivita

Harbor Hills Country Club

6200 TOPSAIL RD, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$275,000

2 beds

2 baths

1,537 sq ft

Villa

6200 TOPSAIL RD, LADY LAKE, FL, 32159

Community: Harbor Hills Country Club

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

Questions? Call us: (689) 407-5757

Oak Run

11684 SW 72ND CIR, OCALA, FL, 34476, Ocala, FL 34476

$342,000

3 beds

2 baths

1,737 sq ft

House

11684 SW 72ND CIR, OCALA, FL, 34476

Community: Oak Run

Sun City Center

$315,000

2 beds

2 baths

1,765 sq ft

House

1714 S PEBBLE BEACH BLVD, SUN CITY CENTE...

Community: Sun City Center

The Villages®

908 ROSE LN, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$164,900

2 beds

2 baths

936 sq ft

Manufactured Home

908 ROSE LN, LADY LAKE, FL, 32159

Community: The Villages®

The Villages®

$264,900

2 beds

2 baths

1,188 sq ft

Villa

2805 BURGOS DR, THE VILLAGES, FL, 32162

Community: The Villages®

Summit Greens

$380,000

3 beds

2 baths

1,556 sq ft

House

890 SUMMIT GREENS BLVD, CLERMONT, FL, 34...

Community: Summit Greens

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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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3,573 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

2 beds

2 baths

1,696 sq ft

Villa

1 beds

1 baths

834 sq ft

House

2 beds

2 baths

1,696 sq ft

House

3 beds

2 baths

1,886 sq ft

House

2 beds

2 baths

1,440 sq ft

Mobile Home

3 beds

3 baths

2,373 sq ft

House

2 beds

2 baths

1,226 sq ft

House

2 beds

2 baths

1,278 sq ft

Villa

2 beds

2 baths

1,808 sq ft

House

3 beds

2 baths

2,272 sq ft

House

2 beds

2 baths

1,383 sq ft

Manufactured Home

2 beds

2 baths

1,383 sq ft

House

3 beds

2 baths

1,724 sq ft

House

2 beds

2 baths

1,612 sq ft

Manufactured Home

3 beds

2 baths

1,827 sq ft

House

3 beds

3 baths

2,817 sq ft

House

2 beds

2 baths

1,756 sq ft

Villa

3 beds

3 baths

2,171 sq ft

House

2 beds

2 baths

1,234 sq ft

House

3 beds