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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.
3.8 rating (6 reviews) Trilogy® Orlando
$200Ks - $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) VillageWalk at Lake Nona
$400Ks - $1Ms
VillageWalk at Lake Nona, Orlando, FL
Resale Only | Age-targeted | Built 2006 - 2016 | 1,300 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
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
Latitude Margaritaville 798 JOLLYMON WAY, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124
$685,000

3 beds

|

3 baths

|

2,067 sq ft

|

House

798 JOLLYMON WAY, DAYTONA BEACH, FL, 321...
Latitude Margaritaville 126 ISLAND BREEZE AVE, DAYTONA BEACH, FL..., Daytona Beach, FL 32124
$729,987

3 beds

|

3 baths

|

2,338 sq ft

|

House

126 ISLAND BREEZE AVE, DAYTONA BEACH, FL...
Latitude Margaritaville 182 ISLAND BREEZE AVE, DAYTONA BEACH, FL..., Daytona Beach, FL 32124
$700,000

3 beds

|

3 baths

|

2,303 sq ft

|

House

182 ISLAND BREEZE AVE, DAYTONA BEACH, FL...
Latitude Margaritaville 586 LOST SHAKER WAY, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$510,000

3 beds

|

2 baths

|

1,862 sq ft

|

House

586 LOST SHAKER WAY, DAYTONA BEACH, FL, ...
Latitude Margaritaville 220 SAND BAR LN, DAYTONA BEACH, FL, 3212..., Daytona Beach, FL 32124
$519,000

2 beds

|

2 baths

|

1,771 sq ft

|

House

220 SAND BAR LN, DAYTONA BEACH, FL, 3212...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Latitude Margaritaville 484 TROPICS AVE, DAYTONA BEACH, FL, 3212..., Daytona Beach, FL 32124
$674,900

3 beds

|

3 baths

|

2,080 sq ft

|

House

484 TROPICS AVE, DAYTONA BEACH, FL, 3212...
Latitude Margaritaville 1078 CASTAWAY CT, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124
$719,900

2 beds

|

3 baths

|

2,080 sq ft

|

House

1078 CASTAWAY CT, DAYTONA BEACH, FL, 321...
Latitude Margaritaville 300 BLUE STARFISH PL, DAYTONA BEACH, FL,..., Daytona Beach, FL 32124
$790,000

3 beds

|

3 baths

|

2,394 sq ft

|

House

300 BLUE STARFISH PL, DAYTONA BEACH, FL,...
Latitude Margaritaville 544 GOOD LIFE WAY, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32124
$715,000

2 beds

|

3 baths

|

2,067 sq ft

|

House

544 GOOD LIFE WAY, DAYTONA BEACH, FL, 32...
Latitude Margaritaville 281 COMPASS ROSE DR, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$695,000

2 beds

|

3 baths

|

2,067 sq ft

|

House

281 COMPASS ROSE DR, DAYTONA BEACH, FL, ...
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.
Latitude Margaritaville 834 JOLLYMON WAY, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124
$639,900

2 beds

|

3 baths

|

2,080 sq ft

|

House

834 JOLLYMON WAY, DAYTONA BEACH, FL, 321...
The Villages® 2528 BUTTONWOOD RUN, THE VILLAGES, FL, 3..., The Villages, FL 32162
$354,900

3 beds

|

2 baths

|

1,477 sq ft

|

House

2528 BUTTONWOOD RUN, THE VILLAGES, FL, 3...
Community: The Villages®
Pine Run Estates 10495 SW 100TH AVE, OCALA, FL, 34481, Ocala, FL 34481
$129,000

2 beds

|

1 baths

|

672 sq ft

|

House

10495 SW 100TH AVE, OCALA, FL, 34481
Community: Pine Run Estates
Solivita 151 BELL TOWER XING W, KISSIMMEE, FL, 34..., Kissimmee, FL 34759
$239,000

2 beds

|

2 baths

|

1,356 sq ft

|

House

151 BELL TOWER XING W, KISSIMMEE, FL, 34...
Community: Solivita
Sun City Center 761 TREMONT GREENS LN # 61, SUN CITY CEN..., Sun City Center, FL 33573
$192,000

2 beds

|

2 baths

|

1,110 sq ft

|

Condo

761 TREMONT GREENS LN # 61, SUN CITY CEN...
Community: Sun City Center
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Pennbrooke Fairways 544 GRAND VISTA TRL, LEESBURG, FL, 34748, Leesburg, FL 34748
$320,000

3 beds

|

2 baths

|

1,869 sq ft

|

House

544 GRAND VISTA TRL, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Spruce Creek South 17475 SE 107TH CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$298,900

2 beds

|

2 baths

|

1,678 sq ft

|

House

17475 SE 107TH CT, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
Pennbrooke Fairways 751 OLD OAKS LN, LEESBURG, FL, 34748, Leesburg, FL 34748
$329,000

3 beds

|

2 baths

|

1,753 sq ft

|

House

751 OLD OAKS LN, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Sun City Center 205 ANDOVER PL N UNIT 110, SUN CITY CENT..., Sun City Center, FL 33573
$129,500

1 beds

|

2 baths

|

800 sq ft

|

Condo

205 ANDOVER PL N UNIT 110, SUN CITY CENT...
Community: Sun City Center
Legacy of Leesburg 27401 PINE STRAW RD, LEESBURG, FL, 34748, Leesburg, FL 34748
$349,900

3 beds

|

2 baths

|

2,031 sq ft

|

House

27401 PINE STRAW RD, LEESBURG, FL, 34748
Community: Legacy of Leesburg
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.
Tampa Bay Golf and Country Club 10230 OLD TAMPA BAY DR, SAN ANTONIO, FL,..., San Antonio, FL 33576
$350,000

2 beds

|

2 baths

|

1,599 sq ft

|

House

10230 OLD TAMPA BAY DR, SAN ANTONIO, FL,...
Mirada 31452 CABANA RYE AVE, SAN ANTONIO, FL, 3..., San Antonio, FL 33576
$580,000

3 beds

|

3 baths

|

2,350 sq ft

|

House

31452 CABANA RYE AVE, SAN ANTONIO, FL, 3...
Community: Mirada
Royal Highlands 5416 ESSEX CT, LEESBURG, FL, 34748, Leesburg, FL 34748
$359,900

3 beds

|

2 baths

|

2,269 sq ft

|

House

5416 ESSEX CT, LEESBURG, FL, 34748
Community: Royal Highlands
Spruce Creek Country Club 9240 SE 128TH LN, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$450,000

2 beds

|

3 baths

|

2,457 sq ft

|

House

9240 SE 128TH LN, SUMMERFIELD, FL, 34491
Stone Creek 8322 SW 52ND LANE RD, OCALA, FL, 34481, Ocala, FL 34481
$329,280

3 beds

|

2 baths

|

1,662 sq ft

|

House

8322 SW 52ND LANE RD, OCALA, FL, 34481
Community: Stone Creek
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
On Top of the World 8580 SW 97TH LANE RD B, OCALA, FL, 34481, Ocala, FL 34481
$214,999

2 beds

|

2 baths

|

1,278 sq ft

|

Villa

8580 SW 97TH LANE RD B, OCALA, FL, 34481
Community: On Top of the World
Valencia del Sol 4906 AVILA LAKES DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$333,000

2 beds

|

2 baths

|

1,646 sq ft

|

Villa

4906 AVILA LAKES DR, WIMAUMA, FL, 33598
Community: Valencia del Sol
On Top of the World 8862 SW 92ND ST D, OCALA, FL, 34481, Ocala, FL 34481
$179,900

2 beds

|

2 baths

|

1,530 sq ft

|

Villa

8862 SW 92ND ST D, OCALA, FL, 34481
Community: On Top of the World
Breakaway Trails 24 LAKE VISTA WAY, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$554,900

4 beds

|

3 baths

|

2,544 sq ft

|

House

24 LAKE VISTA WAY, ORMOND BEACH, FL, 321...
Community: Breakaway Trails
Solivita 3390 FALLBROOK DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$290,000

2 beds

|

2 baths

|

1,353 sq ft

|

House

3390 FALLBROOK DR, KISSIMMEE, FL, 34759
Community: Solivita
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.
Solivita 554 HEARTWELL DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$339,900

2 beds

|

2 baths

|

2,049 sq ft

|

House

554 HEARTWELL DR, KISSIMMEE, FL, 34759
Community: Solivita
Solivita 2448 PALM TREE DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$314,900

3 beds

|

2 baths

|

1,539 sq ft

|

Villa

2448 PALM TREE DR, KISSIMMEE, FL, 34759
Community: Solivita
Solivita 806 EBB TIDE LN, POINCIANA, FL, 34759, Poinciana, FL 34759
$439,900

3 beds

|

3 baths

|

2,011 sq ft

|

House

806 EBB TIDE LN, POINCIANA, FL, 34759
Community: Solivita
Valencia Lakes 5006 RUBY FLATS DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$595,000

3 beds

|

2 baths

|

2,180 sq ft

|

House

5006 RUBY FLATS DR, WIMAUMA, FL, 33598
Community: Valencia Lakes
Sun City Center 1727 COCO PALM CIR, SUN CITY CENTER, FL,..., Sun City Center, FL 33573
$325,000

3 beds

|

2 baths

|

2,108 sq ft

|

House

1727 COCO PALM CIR, SUN CITY CENTER, FL,...
Community: Sun City Center
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Del Webb Sunbridge 6553 ROVER WAY, SAINT CLOUD, FL, 34771, Saint Cloud, FL 34771
$524,990

3 beds

|

3 baths

|

2,018 sq ft

|

House

6553 ROVER WAY, SAINT CLOUD, FL, 34771
Community: Del Webb Sunbridge
Del Webb Sunbridge 3012 MIRAGE PL, SAINT CLOUD, FL, 34771, Saint Cloud, FL 34771
$474,990

3 beds

|

2 baths

|

1,739 sq ft

|

House

3012 MIRAGE PL, SAINT CLOUD, FL, 34771
Community: Del Webb Sunbridge
Sun City Center 2411 LANCASTER DR, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$209,000

2 beds

|

2 baths

|

1,529 sq ft

|

Condo

2411 LANCASTER DR, SUN CITY CENTER, FL, ...
Community: Sun City Center
Lake Henry Estates 530 EASTLAKE DR, HAINES CITY, FL, 33844, Haines City, FL 33844
$264,500

2 beds

|

2 baths

|

1,285 sq ft

|

House

530 EASTLAKE DR, HAINES CITY, FL, 33844
Community: Lake Henry Estates
Spring Lake Towers 700 MIRROR TER 508, WINTER HAVEN, FL, 33..., Winter Haven, FL 33881
$104,000

1 beds

|

1 baths

|

874 sq ft

|

Condo

700 MIRROR TER 508, WINTER HAVEN, FL, 33...
Community: Spring Lake Towers

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3,958 homes near Winter Garden
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