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

3,631 homes near Winter Garden

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5 rating (1 reviews)

Del Webb Oasis

$400Ks - $900Ks

Del Webb Oasis, Winter Garden, FL

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

4 rating (17 reviews)

The Villages®

<$100k - $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

<$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 (48 reviews)

Latitude Margaritaville

$300Ks - $900Ks

Latitude Margaritaville, Daytona Beach, FL

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

4.2 rating (10 reviews)

Stone Creek

$200Ks - $700Ks

Stone Creek, Ocala, FL

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

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 - $500Ks

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

$100Ks - $200Ks

Cypress Lakes, Lakeland, FL

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

5 rating (3 reviews)

Lake Ashton

$200Ks - $800Ks

Lake Ashton, Lake Wales, FL

Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 homes

No reviews yet

Venetian Bay

$200Ks - $2Ms

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 - $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

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 - $1Ms

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

<$100k - $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 - $500Ks

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 - $500Ks

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

$400Ks - $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

4.4 rating (16 reviews)

Del Webb Orlando

$300Ks - $400Ks

Del Webb Orlando, Davenport, FL

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

No reviews yet

Pine Run Estates

<$100k - $300Ks

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

Latitude Margaritaville

351 LOST SHAKER WAY, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124

$449,900

2 beds

2 baths

1,558 sq ft

House

351 LOST SHAKER WAY, DAYTONA BEACH, FL, ...

Community: Latitude Margaritaville

Venetian Bay

422 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168

$653,702

4 beds

3 baths

2,542 sq ft

House

422 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ...

Community: Venetian Bay

Latitude Margaritaville

221 ISLAND BREEZE AVE, DAYTONA BEACH, FL..., Daytona Beach, FL 32124

$455,000

2 beds

2 baths

1,503 sq ft

House

221 ISLAND BREEZE AVE, DAYTONA BEACH, FL...

Community: Latitude Margaritaville

Pelican Bay Daytona Beach

128 GOLDEN EYE DR B, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119

$239,900

3 beds

2 baths

1,376 sq ft

Condo

128 GOLDEN EYE DR B, DAYTONA BEACH, FL, ...

Community: Pelican Bay Daytona Beach

Highlands Ridge

5056 BIRKDALE DR, AVON PARK, FL, 33825, Avon Park, FL 33825

$299,900

2 beds

2 baths

1,799 sq ft

Villa

5056 BIRKDALE DR, AVON PARK, FL, 33825

Community: Highlands Ridge

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

Questions? Call us: (689) 407-5757

Venetian Bay

711 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168

$529,990

3 beds

3 baths

2,796 sq ft

House

711 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ...

Community: Venetian Bay

Pelican Bay Daytona Beach

108 MARSH WREN CT, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32119

$269,900

3 beds

2 baths

1,384 sq ft

House

108 MARSH WREN CT, DAYTONA BEACH, FL, 32...

Community: Pelican Bay Daytona Beach

Highlands Ridge

4032 CARTER CREEK DR, AVON PARK, FL, 338..., Avon Park, FL 33825

$479,000

3 beds

3 baths

2,808 sq ft

House

4032 CARTER CREEK DR, AVON PARK, FL, 338...

Community: Highlands Ridge

Venetian Bay

706 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168

$449,990

3 beds

3 baths

2,125 sq ft

House

706 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ...

Community: Venetian Bay

Latitude Margaritaville

168 OCEAN HAMMOCK LOOP, DAYTONA BEACH, F..., Daytona Beach, FL 32124

$439,000

2 beds

2 baths

1,466 sq ft

Townhouse

168 OCEAN HAMMOCK LOOP, DAYTONA BEACH, F...

Community: Latitude Margaritaville

Mirada

10450 WELDON CORK WAY, SAN ANTONIO, FL, ..., San Antonio, FL 33576

$240,000

2 beds

2 baths

1,405 sq ft

Villa

10450 WELDON CORK WAY, SAN ANTONIO, FL, ...

Community: Mirada

Sun City Center

$319,000

2 beds

2 baths

1,858 sq ft

House

1811 EL RANCHO DR, SUN CITY CENTER, FL, ...

1224 VALLEY FORGE BLVD, SUN CITY CENTER,...

Condo

403 FULHAM CT B, SUN CITY CENTER, FL, 33...

6037 WHISPERING TREES LN, PORT ORANGE, F...

Community: Summer Trees

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

Questions? Call us: (689) 407-5757

Sun City Center

$165,000

2 beds

2 baths

1,073 sq ft

Condo

311 KELSEY WAY # 3, SUN CITY CENTER, FL,...

Community: Sun City Center

Lake James

$495,000

2 beds

2 baths

1,990 sq ft

House

7770 LAKE JAMES BLVD, LAKELAND, FL, 3381...

Community: Lake James

The Villages®

$799,900

3 beds

2 baths

2,015 sq ft

House

1028 WATERLOO WAY, THE VILLAGES, FL, 321...

Community: The Villages®

The Villages®

$244,999

2 beds

2 baths

1,204 sq ft

House

3326 ROANOKE ST, THE VILLAGES, FL, 32162

Community: The Villages®

Pennbrooke Fairways

33409 PENNBROOKE PKWY, LEESBURG, FL, 347..., Leesburg, FL 34748

$334,247

3 beds

2 baths

2,111 sq ft

House

33409 PENNBROOKE PKWY, LEESBURG, FL, 347...

Community: Pennbrooke Fairways

Harbor Hills Country Club

5312 MEADOW HILL LOOP, LADY LAKE, FL, 32..., Lady Lake, FL 32159

$589,000

4 beds

3 baths

2,532 sq ft

House

5312 MEADOW HILL LOOP, LADY LAKE, FL, 32...

Community: Harbor Hills Country Club

On Top of the World

7595 SW 88TH TERRACE RD, OCALA, FL, 3448..., Ocala, FL 34481

$384,500

2 beds

2 baths

1,747 sq ft

House

7595 SW 88TH TERRACE RD, OCALA, FL, 3448...

Community: On Top of the World

Venetian Bay

3322 MODENA WAY, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168

$625,000

3 beds

2 baths

1,916 sq ft

House

3322 MODENA WAY, NEW SMYRNA BEACH, FL, 3...

Community: Venetian Bay

Sun City Center

$299,900

2 beds

2 baths

1,206 sq ft

Condo

2082 SIFIELD GREENS WAY # 3, SUN CITY CE...

Community: Sun City Center

Latitude Margaritaville

220 SAND BAR LN, DAYTONA BEACH, FL, 3212..., Daytona Beach, FL 32124

$489,500

2 beds

2 baths

1,771 sq ft

House

220 SAND BAR LN, DAYTONA BEACH, FL, 3212...

House

4921 KELSO ST, LEESBURG, FL, 34748

Community: Royal Highlands

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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.

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

Call us: (689) 407-5757

3,631 homes near Winter Garden

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

108 communities near Winter Garden

3,631 homes near Winter Garden

2 beds

2 baths

1,558 sq ft

House

4 beds

3 baths

2,542 sq ft

House

2 beds

2 baths

1,503 sq ft

House

3 beds

2 baths

1,376 sq ft

Condo

2 beds

2 baths

1,799 sq ft

Villa

3 beds

3 baths

2,796 sq ft

House

3 beds

2 baths

1,384 sq ft

House

3 beds

3 baths

2,808 sq ft

House

3 beds

3 baths

2,125 sq ft

House

2 beds

2 baths

1,466 sq ft

Townhouse

2 beds

2 baths

1,405 sq ft

Villa

2 beds

2 baths

1,858 sq ft

House

2 beds

2 baths

1,603 sq ft

House

2 beds

2 baths

1,182 sq ft

House

2 beds

2 baths

1,287 sq ft

House

3 beds

2 baths

1,863 sq ft

House

2 beds

2 baths

1,857 sq ft

House

2 beds

2 baths

960 sq ft

Condo

2 beds

2 baths

1,800 sq ft

House

2 beds