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

3,958 homes near Winter Garden

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No reviews yet 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 - $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
<$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
$200Ks - $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 - $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 - $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 - $600Ks
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 - $1Ms
Twin Lakes, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes
No reviews yet Pelican Bay Daytona Beach
<$100k - $600Ks
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
$200Ks - $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 - $900Ks
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
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 (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
$200Ks - $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) 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
$100Ks - $300Ks
Pennbrooke Fairways, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 homes
5 rating (1 reviews) Sandpiper Golf & Coun...
$100Ks - $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
$300Ks - $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
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 (5 reviews) SummerGlen
$200Ks - $500Ks
SummerGlen, Ocala, FL
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,029 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 - $700Ks
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 homes
4 rating (4 reviews) Lakes of Mount Dora
$200Ks - $800Ks
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 - $800Ks
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
$100Ks - $300Ks
Highland Lakes, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes
4.3 rating (15 reviews) Del Webb Orlando
$200Ks - $500Ks
Del Webb Orlando, Davenport, FL
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes
No reviews yet Pine Run Estates
$100Ks - $400Ks
Pine Run Estates, Ocala, FL
Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 homes
No reviews yet Lake Jovita Golf and Coun...
$400Ks - $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 - $900Ks
Esplanade at Wiregrass Ra..., Wesley Chapel, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 868 homes
Ocala Preserve 5616 NW 39TH LN, OCALA, FL, 34482, Ocala, FL 34482
$304,900

2 beds

|

2 baths

|

1,454 sq ft

|

House

5616 NW 39TH LN, OCALA, FL, 34482
Community: Ocala Preserve
Pine Run Estates 9940 SW 103RD PL, OCALA, FL, 34481, Ocala, FL 34481
$179,900

2 beds

|

2 baths

|

1,144 sq ft

|

House

9940 SW 103RD PL, OCALA, FL, 34481
Community: Pine Run Estates
Kings Ridge 2126 BURLEY AVE, CLERMONT, FL, 34711, Clermont, FL 34711
$339,000

2 beds

|

2 baths

|

1,460 sq ft

|

House

2126 BURLEY AVE, CLERMONT, FL, 34711
Community: Kings Ridge
Stone Creek 9793 SW 63RD LOOP, OCALA, FL, 34481, Ocala, FL 34481
$487,500

4 beds

|

2 baths

|

2,186 sq ft

|

House

9793 SW 63RD LOOP, OCALA, FL, 34481
Community: Stone Creek
Summer Trees 102 UNDERBRUSH TRL, PORT ORANGE, FL, 321..., Port Orange, FL 32128
$299,999

2 beds

|

2 baths

|

1,370 sq ft

|

House

102 UNDERBRUSH TRL, PORT ORANGE, FL, 321...
Community: Summer Trees
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Highlands Ridge 3501 E SAINT ANDREWS DR, AVON PARK, FL, ..., Avon Park, FL 33825
$299,900

3 beds

|

2 baths

|

1,999 sq ft

|

House

3501 E SAINT ANDREWS DR, AVON PARK, FL, ...
Community: Highlands Ridge
Spruce Creek Country Club 8602 SE 133RD LN, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$270,000

2 beds

|

2 baths

|

1,490 sq ft

|

House

8602 SE 133RD LN, SUMMERFIELD, FL, 34491
SummerGlen 15782 SW 16TH AVENUE RD, OCALA, FL, 3447..., Ocala, FL 34473
$258,500

3 beds

|

2 baths

|

1,676 sq ft

|

House

15782 SW 16TH AVENUE RD, OCALA, FL, 3447...
Community: SummerGlen
Sandpiper Golf & Country Club 6059 CONDOR DR, LAKELAND, FL, 33809, Lakeland, FL 33809
$395,000

3 beds

|

2 baths

|

2,195 sq ft

|

House

6059 CONDOR DR, LAKELAND, FL, 33809
On Top of the World 8798 SW 79TH CT, OCALA, FL, 34476, Ocala, FL 34476
$321,000

3 beds

|

2 baths

|

1,469 sq ft

|

House

8798 SW 79TH CT, OCALA, FL, 34476
Community: On Top of the World
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.
The Lakes at Harmony 3443 SAGEBRUSH ST, HARMONY, FL, 34773, Harmony, FL 34773
$309,900

2 beds

|

2 baths

|

1,637 sq ft

|

House

3443 SAGEBRUSH ST, HARMONY, FL, 34773
Sun City Center 2509 LOCKSLEY ST # 237, SUN CITY CENTER,..., Sun City Center, FL 33573
$300,000

2 beds

|

2 baths

|

1,878 sq ft

|

Condo

2509 LOCKSLEY ST # 237, SUN CITY CENTER,...
Community: Sun City Center
Tampa Bay Golf and Country Club 9608 ROLLING CIR, SAN ANTONIO, FL, 33576, San Antonio, FL 33576
$328,000

3 beds

|

2 baths

|

1,390 sq ft

|

House

9608 ROLLING CIR, SAN ANTONIO, FL, 33576
Huntington at Hunter's Ridge 81 HUNTINGTON PL, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174
$379,000

4 beds

|

2 baths

|

2,033 sq ft

|

House

81 HUNTINGTON PL, ORMOND BEACH, FL, 3217...
The Villages® 1971 CERNY CT, THE VILLAGES, FL, 32163, The Villages, FL 32163
$345,000

2 beds

|

2 baths

|

1,290 sq ft

|

House

1971 CERNY CT, THE VILLAGES, FL, 32163
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Pelican Bay Daytona Beach 115 MORNING DOVE CT, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119
$367,999

3 beds

|

2 baths

|

2,075 sq ft

|

House

115 MORNING DOVE CT, DAYTONA BEACH, FL, ...
Sun City Center 1112 MCDANIEL ST # 78, SUN CITY CENTER, ..., Sun City Center, FL 33573
$285,000

2 beds

|

2 baths

|

1,757 sq ft

|

Halfplex

1112 MCDANIEL ST # 78, SUN CITY CENTER, ...
Community: Sun City Center
Venetian Bay 3088 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$334,998

2 beds

|

2 baths

|

1,416 sq ft

|

House

3088 MELETO BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Heritage Hills 3205 SONESTA CT F, CLERMONT, FL, 34711, Clermont, FL 34711
$328,000

2 beds

|

2 baths

|

1,503 sq ft

|

Villa

3205 SONESTA CT F, CLERMONT, FL, 34711
Community: Heritage Hills
Summer Trees 6017 HICKORY GROVE LN, PORT ORANGE, FL, ..., Port Orange, FL 32128
$489,000

4 beds

|

2 baths

|

1,808 sq ft

|

House

6017 HICKORY GROVE LN, PORT ORANGE, FL, ...
Community: Summer Trees
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.
Twin Lakes 2460 PROMENADE DR, SAINT CLOUD, FL, 3477..., Saint Cloud, FL 34772
$465,000

3 beds

|

2 baths

|

1,863 sq ft

|

House

2460 PROMENADE DR, SAINT CLOUD, FL, 3477...
Community: Twin Lakes
Sun City Center 1503 COUNCIL DR, SUN CITY CENTER, FL, 33..., Sun City Center, FL 33573
$250,000

2 beds

|

2 baths

|

1,346 sq ft

|

House

1503 COUNCIL DR, SUN CITY CENTER, FL, 33...
Community: Sun City Center
Quail Meadow 4941 NW 32ND ST, OCALA, FL, 34482, Ocala, FL 34482
$383,000

4 beds

|

3 baths

|

2,443 sq ft

|

House

4941 NW 32ND ST, OCALA, FL, 34482
Community: Quail Meadow
On Top of the World 8665 SW 94TH LN C, OCALA, FL, 34481, Ocala, FL 34481
$237,500

2 beds

|

2 baths

|

1,541 sq ft

|

Villa

8665 SW 94TH LN C, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 8685 SW 94TH LN B, OCALA, FL, 34481, Ocala, FL 34481
$187,500

2 beds

|

2 baths

|

1,571 sq ft

|

Villa

8685 SW 94TH LN B, 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
Harbor Hills Country Club 6027 SPINNAKER LOOP, LADY LAKE, FL, 3215..., Lady Lake, FL 32159
$399,000

3 beds

|

2 baths

|

1,950 sq ft

|

House

6027 SPINNAKER LOOP, LADY LAKE, FL, 3215...
Sun City Center 1205 CHEVY CHASE DR, SUN CITY CENTER, FL..., Sun City Center, FL 33573
$227,000

2 beds

|

2 baths

|

1,266 sq ft

|

House

1205 CHEVY CHASE DR, SUN CITY CENTER, FL...
Community: Sun City Center
Traditions at Lake Ruby 4068 CARTERET DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$289,250

3 beds

|

2 baths

|

1,928 sq ft

|

House

4068 CARTERET DR, WINTER HAVEN, FL, 3388...
Twin Lakes 2756 GREENLANDS ST, SAINT CLOUD, FL, 347..., Saint Cloud, FL 34772
$349,900

2 beds

|

2 baths

|

1,624 sq ft

|

House

2756 GREENLANDS ST, SAINT CLOUD, FL, 347...
Community: Twin Lakes
Plantation at Leesburg 24429 MADEWOOD AVE, LEESBURG, FL, 34748, Leesburg, FL 34748
$369,000

2 beds

|

2 baths

|

2,104 sq ft

|

House

24429 MADEWOOD AVE, LEESBURG, FL, 34748
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.
Harbor Hills Country Club 39331 TREELINE DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$460,000

3 beds

|

3 baths

|

2,086 sq ft

|

House

39331 TREELINE DR, LADY LAKE, FL, 32159
Twin Lakes 2491 YELLOW BRICK RD, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34772
$304,900

2 beds

|

2 baths

|

1,464 sq ft

|

Halfplex

2491 YELLOW BRICK RD, SAINT CLOUD, FL, 3...
Community: Twin Lakes
Del Webb Orlando 333 NAVARRA LN, DAVENPORT, FL, 33837, Davenport, FL 33837
$449,500

3 beds

|

2 baths

|

2,028 sq ft

|

House

333 NAVARRA LN, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Solivita 729 SAN RAPHAEL ST, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$524,900

4 beds

|

4 baths

|

2,616 sq ft

|

House

729 SAN RAPHAEL ST, KISSIMMEE, FL, 34759
Community: Solivita
On Top of the World 8420 SW 92ND ST A, OCALA, FL, 34481, Ocala, FL 34481
$179,900

2 beds

|

2 baths

|

1,366 sq ft

|

Villa

8420 SW 92ND ST A, 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
Ocala Preserve 5662 NW 40TH PL, OCALA, FL, 34482, Ocala, FL 34482
$395,900

3 beds

|

2 baths

|

1,862 sq ft

|

House

5662 NW 40TH PL, OCALA, FL, 34482
Community: Ocala Preserve
The Villages® 7675 COUNTY ROAD 109E, LADY LAKE, FL, 32..., Lady Lake, FL 32159
$234,900

3 beds

|

2 baths

|

1,568 sq ft

|

Manufactured Home

7675 COUNTY ROAD 109E, LADY LAKE, FL, 32...
Community: The Villages®
Stone Creek 9532 SW 70TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$568,865

3 beds

|

3 baths

|

2,773 sq ft

|

House

9532 SW 70TH LOOP, OCALA, FL, 34481
Community: Stone Creek
Tampa Bay Golf and Country Club 10048 CLEGHORN DR, SAN ANTONIO, FL, 3357..., San Antonio, FL 33576
$387,000

3 beds

|

2 baths

|

2,229 sq ft

|

House

10048 CLEGHORN DR, SAN ANTONIO, FL, 3357...
Sullivan Ranch 30120 HACKNEY LOOP, MOUNT DORA, FL, 3275..., Mount Dora, FL 32757
$615,000

4 beds

|

4 baths

|

3,307 sq ft

|

House

30120 HACKNEY LOOP, MOUNT DORA, FL, 3275...
Community: Sullivan Ranch

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3,958 homes near Winter Garden
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