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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
Solivita 343 SCRIPPS RANCH RD, POINCIANA, FL, 347..., Poinciana, FL 34759
$310,000

2 beds

|

2 baths

|

1,556 sq ft

|

House

343 SCRIPPS RANCH RD, POINCIANA, FL, 347...
Community: Solivita
Quail Meadow 5040 NW 35TH ST, OCALA, FL, 34482, Ocala, FL 34482
$349,888

3 beds

|

2 baths

|

2,150 sq ft

|

House

5040 NW 35TH ST, OCALA, FL, 34482
Community: Quail Meadow
Solivita 3775 VIA MAZZINI CT, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759
$549,000

4 beds

|

3 baths

|

2,495 sq ft

|

House

3775 VIA MAZZINI CT, KISSIMMEE, FL, 3475...
Community: Solivita
The Villages® 17238 SE 94TH COULTS CIR, THE VILLAGES, ..., The Villages, FL 32162
$359,900

3 beds

|

2 baths

|

1,558 sq ft

|

House

17238 SE 94TH COULTS CIR, THE VILLAGES, ...
Community: The Villages®
Highland Fairways 3173 SAND TRAP CT, LAKELAND, FL, 33810, Lakeland, FL 33810
$244,000

2 beds

|

2 baths

|

1,193 sq ft

|

House

3173 SAND TRAP CT, LAKELAND, FL, 33810
Community: Highland Fairways
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Solivita 159 VENTANA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$339,500

3 beds

|

2 baths

|

1,813 sq ft

|

House

159 VENTANA DR, KISSIMMEE, FL, 34759
Community: Solivita
Traditions at Lake Ruby 3565 RALEIGH DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$315,000

3 beds

|

2 baths

|

1,866 sq ft

|

House

3565 RALEIGH DR, WINTER HAVEN, FL, 33884
Legacy of Leesburg 27302 ORCHID GLADE ST, LEESBURG, FL, 347..., Leesburg, FL 34748
$369,000

3 beds

|

2 baths

|

1,905 sq ft

|

House

27302 ORCHID GLADE ST, LEESBURG, FL, 347...
Community: Legacy of Leesburg
The Villages® 2538 PRIVADA DR, THE VILLAGES, FL, 32162, The Villages, FL 32162
$335,000

3 beds

|

2 baths

|

1,527 sq ft

|

House

2538 PRIVADA DR, THE VILLAGES, FL, 32162
Community: The Villages®
Arlington Ridge 27018 WHITE PLAINS WAY, LEESBURG, FL, 34..., Leesburg, FL 34748
$275,000

2 beds

|

2 baths

|

1,208 sq ft

|

Villa

27018 WHITE PLAINS WAY, LEESBURG, FL, 34...
Community: Arlington Ridge
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 39342 HARBOR HILLS BLVD, LADY LAKE, FL, ..., Lady Lake, FL 32159
$499,000

3 beds

|

2 baths

|

2,233 sq ft

|

House

39342 HARBOR HILLS BLVD, LADY LAKE, FL, ...
Sun City Center 2313 GRENOBLE PL # 2313, SUN CITY CENTER..., Sun City Center, FL 33573
$210,000

2 beds

|

2 baths

|

1,008 sq ft

|

Condo

2313 GRENOBLE PL # 2313, SUN CITY CENTER...
Community: Sun City Center
Stone Creek 9175 SW 65TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$659,000

3 beds

|

4 baths

|

2,844 sq ft

|

House

9175 SW 65TH LOOP, OCALA, FL, 34481
Community: Stone Creek
Solivita 251 ROCK SPRINGS DR, POINCIANA, FL, 3475..., Poinciana, FL 34759
$350,000

2 beds

|

2 baths

|

2,085 sq ft

|

House

251 ROCK SPRINGS DR, POINCIANA, FL, 3475...
Community: Solivita
Solivita 251 ROCK SPRINGS DR, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759
$350,000

2 beds

|

2 baths

|

2,050 sq ft

|

House

251 ROCK SPRINGS DR, KISSIMMEE, FL, 3475...
Community: Solivita
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Ocala Palms 5097 NW 19TH PL, OCALA, FL, 34482, Ocala, FL 34482
$249,900

2 beds

|

2 baths

|

1,700 sq ft

|

House

5097 NW 19TH PL, OCALA, FL, 34482
Community: Ocala Palms
Spruce Creek Country Club 8475 SE 137TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$279,999

2 beds

|

2 baths

|

1,652 sq ft

|

House

8475 SE 137TH LOOP, SUMMERFIELD, FL, 344...
Palm Cay 10839 SW 78TH CT, OCALA, FL, 34476, Ocala, FL 34476
$229,000

3 beds

|

2 baths

|

1,404 sq ft

|

House

10839 SW 78TH CT, OCALA, FL, 34476
Community: Palm Cay
High Vista at Ridgewood Lakes 520 VISTA OAKS WAY, DAVENPORT, FL, 33837, Davenport, FL 33837
$335,000

2 beds

|

2 baths

|

1,792 sq ft

|

House

520 VISTA OAKS WAY, DAVENPORT, FL, 33837
Spruce Creek Country Club 13340 SE 86TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$335,000

3 beds

|

2 baths

|

1,723 sq ft

|

House

13340 SE 86TH CIR, SUMMERFIELD, FL, 3449...
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.
On Top of the World 9288 SW 93RD CIR, OCALA, FL, 34481, Ocala, FL 34481
$319,900

3 beds

|

2 baths

|

1,910 sq ft

|

House

9288 SW 93RD CIR, OCALA, FL, 34481
Community: On Top of the World
Spruce Creek North 10946 SW 65TH AVE, OCALA, FL, 34476, Ocala, FL 34476
$234,900

2 beds

|

2 baths

|

1,328 sq ft

|

House

10946 SW 65TH AVE, OCALA, FL, 34476
Community: Spruce Creek North
Stone Creek 5947 SW 93RD CIR, OCALA, FL, 34481, Ocala, FL 34481
$299,700

2 beds

|

2 baths

|

1,405 sq ft

|

House

5947 SW 93RD CIR, OCALA, FL, 34481
Community: Stone Creek
Sun City Center 2301 GRENOBLE PL # 1, SUN CITY CENTER, F..., Sun City Center, FL 33573
$178,000

2 beds

|

2 baths

|

1,008 sq ft

|

Condo

2301 GRENOBLE PL # 1, SUN CITY CENTER, F...
Community: Sun City Center
Tarawood 10501 S DREW BRYANT CIR, FLORAL CITY, FL..., Floral City, FL 34436
$265,000

3 beds

|

2 baths

|

1,627 sq ft

|

House

10501 S DREW BRYANT CIR, FLORAL CITY, FL...
Community: Tarawood
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Solivita 651 HIGHLANDS HAMMOCK DR, POINCIANA, FL,..., Poinciana, FL 34759
$315,000

2 beds

|

3 baths

|

1,800 sq ft

|

House

651 HIGHLANDS HAMMOCK DR, POINCIANA, FL,...
Community: Solivita
Tohoqua Reserve 2705 SERENITY MEADOW DR, KISSIMMEE, FL, ..., Kissimmee, FL 34744
$399,200

2 beds

|

2 baths

|

1,670 sq ft

|

House

2705 SERENITY MEADOW DR, KISSIMMEE, FL, ...
Community: Tohoqua Reserve
Sun City Center 2021 E DEL WEBB BLVD, SUN CITY CENTER, F..., Sun City Center, FL 33573
$359,900

2 beds

|

2 baths

|

2,039 sq ft

|

House

2021 E DEL WEBB BLVD, SUN CITY CENTER, F...
Community: Sun City Center
Breakaway Trails 16 FOREST VIEW WAY, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174
$543,000

3 beds

|

3 baths

|

2,114 sq ft

|

House

16 FOREST VIEW WAY, ORMOND BEACH, FL, 32...
Community: Breakaway Trails
Highlands Ridge 4456 TOUSSANT DR, AVON PARK, FL, 33825, Avon Park, FL 33825
$449,000

3 beds

|

2 baths

|

1,722 sq ft

|

House

4456 TOUSSANT DR, AVON PARK, FL, 33825
Community: Highlands Ridge
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.
Foxwood Lake Estates 4985 DEERWOOD DR, LAKELAND, FL, 33810, Lakeland, FL 33810
$159,900

2 beds

|

2 baths

|

1,040 sq ft

|

Manufactured Home

4985 DEERWOOD DR, LAKELAND, FL, 33810
Tohoqua Reserve 2737 SERENITY MEADOW DR, KISSIMMEE, FL, ..., Kissimmee, FL 34744
$424,810

3 beds

|

2 baths

|

1,981 sq ft

|

House

2737 SERENITY MEADOW DR, KISSIMMEE, FL, ...
Community: Tohoqua Reserve
Tohoqua Reserve 2725 SERENITY MEADOW DR, KISSIMMEE, FL, ..., Kissimmee, FL 34744
$418,080

2 beds

|

2 baths

|

1,943 sq ft

|

House

2725 SERENITY MEADOW DR, KISSIMMEE, FL, ...
Community: Tohoqua Reserve
Tohoqua Reserve 2741 SERENITY MEADOW DR, KISSIMMEE, FL, ..., Kissimmee, FL 34744
$432,240

2 beds

|

2 baths

|

1,889 sq ft

|

House

2741 SERENITY MEADOW DR, KISSIMMEE, FL, ...
Community: Tohoqua Reserve
Tohoqua Reserve 2717 SERENITY MEADOW DR, KISSIMMEE, FL, ..., Kissimmee, FL 34744
$418,240

2 beds

|

2 baths

|

1,921 sq ft

|

House

2717 SERENITY MEADOW DR, KISSIMMEE, FL, ...
Community: Tohoqua Reserve
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Tohoqua Reserve 2729 SERENITY MEADOW DR, KISSIMMEE, FL, ..., Kissimmee, FL 34744
$421,320

2 beds

|

2 baths

|

1,921 sq ft

|

House

2729 SERENITY MEADOW DR, KISSIMMEE, FL, ...
Community: Tohoqua Reserve
The Villages® 2573 CARRINGTON CT, THE VILLAGES, FL, 32..., The Villages, FL 32162
$280,000

2 beds

|

2 baths

|

1,188 sq ft

|

House

2573 CARRINGTON CT, THE VILLAGES, FL, 32...
Community: The Villages®
Twin Lakes 2454 DREAM HOME CT, SAINT CLOUD, FL, 347..., Saint Cloud, FL 34772
$777,900

3 beds

|

3 baths

|

2,208 sq ft

|

House

2454 DREAM HOME CT, SAINT CLOUD, FL, 347...
Community: Twin Lakes
Twin Lakes 2458 DREAM HOME CT, SAINT CLOUD, FL, 347..., Saint Cloud, FL 34772
$961,900

3 beds

|

3 baths

|

2,966 sq ft

|

House

2458 DREAM HOME CT, SAINT CLOUD, FL, 347...
Community: Twin Lakes
Highlands Ridge 4309 NORTH COURSE LN, AVON PARK, FL, 338..., Avon Park, FL 33825
$399,900

3 beds

|

2 baths

|

2,221 sq ft

|

House

4309 NORTH COURSE LN, AVON PARK, FL, 338...
Community: Highlands Ridge

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3,958 homes near Winter Garden
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