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

3,703 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 - $500Ks

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

<$100k - $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

$300Ks - $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 - $500Ks

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

13340 SE 86TH CIR, SUMMERFIELD, FL, 3449...

Community: Spruce Creek Country Club

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

Questions? Call us: (689) 407-5757

Stonecrest

11839 SE 173RD LANE RD, SUMMERFIELD, FL,..., Summerfield, FL 34491

$550,000

3 beds

3 baths

2,502 sq ft

House

11839 SE 173RD LANE RD, SUMMERFIELD, FL,...

333 NAVARRA LN, DAVENPORT, FL, 33837

Community: Del Webb Orlando

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

Questions? Call us: (689) 407-5757

SummerGlen

15771 SW 16TH TER, OCALA, FL, 34473, Ocala, FL 34473

$408,000

3 beds

2 baths

2,516 sq ft

House

15771 SW 16TH TER, OCALA, FL, 34473

Community: SummerGlen

On Top of the World

8650 SW 83RD LOOP, OCALA, FL, 34481, Ocala, FL 34481

$368,000

2 beds

2 baths

2,425 sq ft

House

8650 SW 83RD LOOP, OCALA, FL, 34481

Community: On Top of the World

The Villages®

1220 DUSTIN DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$199,000

2 beds

2 baths

1,056 sq ft

Manufactured Home

1220 DUSTIN DR, LADY LAKE, FL, 32159

Community: The Villages®

The Villages®

1725 HILTON HEAD BLVD, LADY LAKE, FL, 32..., Lady Lake, FL 32159

$174,000

2 beds

2 baths

1,092 sq ft

Manufactured Home

1725 HILTON HEAD BLVD, LADY LAKE, FL, 32...

Community: The Villages®

Lake Ashton

5325 NICKLAUS DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884

$284,900

2 beds

2 baths

1,319 sq ft

House

5325 NICKLAUS DR, WINTER HAVEN, FL, 3388...

Community: Lake Ashton

Oak Run

6682 SW 117TH ST, OCALA, FL, 34476, Ocala, FL 34476

$295,000

2 beds

2 baths

1,730 sq ft

House

6682 SW 117TH ST, OCALA, FL, 34476

Community: Oak Run

Pennbrooke Fairways

721 TIMBERCREST DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$289,900

3 beds

2 baths

1,667 sq ft

House

721 TIMBERCREST DR, LEESBURG, FL, 34748

Community: Pennbrooke Fairways

Venetian Bay

367 CARYOTA CT, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168

$422,000

3 beds

2 baths

1,653 sq ft

House

367 CARYOTA CT, NEW SMYRNA BEACH, FL, 32...

Community: Venetian Bay

Highlands Ridge

3120 S PRESTWICK DR, AVON PARK, FL, 3382..., Avon Park, FL 33825

$289,900

3 beds

2 baths

1,901 sq ft

House

3120 S PRESTWICK DR, AVON PARK, FL, 3382...

Community: Highlands Ridge

Solivita

2340 PALM TREE DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$359,000

3 beds

3 baths

2,272 sq ft

Villa

2340 PALM TREE DR, KISSIMMEE, FL, 34759

Community: Solivita

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

Questions? Call us: (689) 407-5757

Solivita

418 TREVISO DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$615,000

3 beds

3 baths

2,427 sq ft

House

418 TREVISO DR, KISSIMMEE, FL, 34759

Community: Solivita

Solivita

105 PALAZZO LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$326,000

2 beds

2 baths

1,590 sq ft

House

105 PALAZZO LN, KISSIMMEE, FL, 34759

Community: Solivita

Lakes of Mount Dora

2046 WALLINGFORD LOOP, MOUNT DORA, FL, 3..., Mount Dora, FL 32757

$559,990

3 beds

2 baths

2,180 sq ft

House

2046 WALLINGFORD LOOP, MOUNT DORA, FL, 3...

Community: Lakes of Mount Dora

Lakes of Mount Dora

8592 HEMPSTEAD WAY, MOUNT DORA, FL, 3275..., Mount Dora, FL 32757

$450,000

3 beds

2 baths

1,524 sq ft

House

8592 HEMPSTEAD WAY, MOUNT DORA, FL, 3275...

Community: Lakes of Mount Dora

Spruce Creek Preserve

14191 SW 115TH TER, DUNNELLON, FL, 34432, Dunnellon, FL 34432

$259,000

2 beds

2 baths

1,687 sq ft

House

14191 SW 115TH TER, DUNNELLON, FL, 34432

Community: Spruce Creek Preserve

Traditions at Lake Ruby

2980 DAYTON DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884

$399,500

4 beds

3 baths

2,302 sq ft

House

2980 DAYTON DR, WINTER HAVEN, FL, 33884

Community: Traditions at Lake Ruby

Harbor Hills Country Club

6036 TOPSAIL RD, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$425,000

3 beds

2 baths

2,181 sq ft

House

6036 TOPSAIL RD, LADY LAKE, FL, 32159

Community: Harbor Hills Country Club

Solivita

436 BEL AIR WAY, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$399,900

2 beds

2 baths

1,975 sq ft

House

436 BEL AIR WAY, KISSIMMEE, FL, 34759

Community: Solivita

Ocala Palms

5647 NW 25TH LOOP, OCALA, FL, 34482, Ocala, FL 34482

$359,000

3 beds

2 baths

2,107 sq ft

House

5647 NW 25TH LOOP, OCALA, FL, 34482

Community: Ocala Palms

Highlands Ridge

5040 BIRKDALE DR, AVON PARK, FL, 33825, Avon Park, FL 33825

$289,900

2 beds

2 baths

1,624 sq ft

Villa

5040 BIRKDALE DR, AVON PARK, FL, 33825

Condo

1609 LAUGHTON PL, SUN CITY CENTER, FL, 3...

Community: Sun City Center

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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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3,703 homes near Winter Garden

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

108 communities near Winter Garden

3,703 homes near Winter Garden

2 beds

2 baths

1,164 sq ft

Villa

2 beds

2 baths

864 sq ft

House

2 beds

2 baths

1,320 sq ft

Manufactured Home

2 beds

2 baths

1,911 sq ft

House

3 beds

2 baths

1,723 sq ft

House

3 beds

3 baths

2,502 sq ft

House

3 beds

2 baths

2,127 sq ft

House

2 beds

2 baths

1,160 sq ft

House

1 beds

2 baths

800 sq ft

Condo

2 beds

2 baths

1,483 sq ft

Condo

2 beds

2 baths

1,469 sq ft

House

2 beds

2 baths

1,464 sq ft

Villa

1 beds

2 baths

800 sq ft

Condo

3 beds

2 baths

1,927 sq ft

House

3 beds

2 baths

2,028 sq ft

House

3 beds

2 baths

2,516 sq ft

House

2 beds

2 baths

2,425 sq ft

House

2 beds

2 baths

1,056 sq ft

Manufactured Home

2 beds

2 baths

1,092 sq ft

Manufactured Home

2 beds