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

3,573 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 - $2Ms
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!
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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 - $500Ks
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 - $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
$200Ks - $200Ks
Cypress Lakes, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1987 - 2016 | 1,604 homes
5 rating (3 reviews) Lake Ashton
$200Ks - $500Ks
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
$300Ks - $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) 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 - $900Ks
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...
$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 - $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 - $400Ks
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
$300Ks - $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
4.3 rating (15 reviews) Del Webb Orlando
$200Ks - $400Ks
Del Webb Orlando, Davenport, FL
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes
No reviews yet Pine Run Estates
<$100k - $400Ks
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
Sandpiper Golf & Country Club 5920 CORMORANT CT, LAKELAND, FL, 33809, Lakeland, FL 33809
$375,000

3 beds

|

2 baths

|

1,582 sq ft

|

House

5920 CORMORANT CT, LAKELAND, FL, 33809
Sandpiper Golf & Country Club 5926 CORMORANT CT, LAKELAND, FL, 33809, Lakeland, FL 33809
$385,000

3 beds

|

2 baths

|

1,640 sq ft

|

House

5926 CORMORANT CT, LAKELAND, FL, 33809
Sandpiper Golf & Country Club 5927 CORMORANT CT, LAKELAND, FL, 33809, Lakeland, FL 33809
$350,000

2 beds

|

2 baths

|

1,321 sq ft

|

House

5927 CORMORANT CT, LAKELAND, FL, 33809
Sandpiper Golf & Country Club 5921 CORMORANT CT, LAKELAND, FL, 33809, Lakeland, FL 33809
$385,000

3 beds

|

2 baths

|

1,640 sq ft

|

House

5921 CORMORANT CT, LAKELAND, FL, 33809
Sandpiper Golf & Country Club 5933 CORMORANT CT, LAKELAND, FL, 33809, Lakeland, FL 33809
$350,000

2 beds

|

2 baths

|

1,321 sq ft

|

House

5933 CORMORANT CT, LAKELAND, FL, 33809
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Plantation at Leesburg 5057 EL DESTINO DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$174,000

2 beds

|

2 baths

|

1,170 sq ft

|

Manufactured Home

5057 EL DESTINO DR, LEESBURG, FL, 34748
Quail Meadow 5003 NW 32ND ST, OCALA, FL, 34482, Ocala, FL 34482
$279,900

3 beds

|

2 baths

|

1,441 sq ft

|

House

5003 NW 32ND ST, OCALA, FL, 34482
Community: Quail Meadow
Quail Meadow 4937 NW 30TH PL, OCALA, FL, 34482, Ocala, FL 34482
$279,900

3 beds

|

2 baths

|

1,463 sq ft

|

House

4937 NW 30TH PL, OCALA, FL, 34482
Community: Quail Meadow
Oak Run 8418 SW 108TH PLACE RD, OCALA, FL, 34481, Ocala, FL 34481
$324,900

3 beds

|

3 baths

|

2,361 sq ft

|

House

8418 SW 108TH PLACE RD, OCALA, FL, 34481
Community: Oak Run
Tampa Bay Golf and Country Club 29417 CADDYSHACK LN, SAN ANTONIO, FL, 33..., San Antonio, FL 33576
$279,000

3 beds

|

2 baths

|

1,384 sq ft

|

Villa

29417 CADDYSHACK LN, SAN ANTONIO, FL, 33...
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 Villages® 1329 PARADISE DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$315,000

3 beds

|

2 baths

|

1,366 sq ft

|

House

1329 PARADISE DR, LADY LAKE, FL, 32159
Community: The Villages®
Harbor Hills Country Club 39900 BAYVIEW DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$290,000

2 beds

|

2 baths

|

1,228 sq ft

|

House

39900 BAYVIEW DR, LADY LAKE, FL, 32159
Solivita 501 HEARTWELL DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$320,000

2 beds

|

2 baths

|

1,574 sq ft

|

House

501 HEARTWELL DR, POINCIANA, FL, 34759
Community: Solivita
Sun City Center 1171 CORINTH GREENS DR, SUN CITY CENTER,..., Sun City Center, FL 33573
$255,000

2 beds

|

2 baths

|

1,450 sq ft

|

Condo

1171 CORINTH GREENS DR, SUN CITY CENTER,...
Community: Sun City Center
The Villages® 1819 CAPTIVA CT, THE VILLAGES, FL, 32162, The Villages, FL 32162
$320,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

1819 CAPTIVA CT, THE VILLAGES, FL, 32162
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Spruce Creek Country Club 11816 SE 91ST CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$312,500

2 beds

|

2 baths

|

1,575 sq ft

|

House

11816 SE 91ST CIR, SUMMERFIELD, FL, 3449...
Harbor Hills Country Club 39320 HARBOR HILLS BLVD, LADY LAKE, FL, ..., Lady Lake, FL 32159
$484,000

3 beds

|

2 baths

|

2,120 sq ft

|

House

39320 HARBOR HILLS BLVD, LADY LAKE, FL, ...
On Top of the World 9342 SW 102ND TERRACE RD, OCALA, FL, 344..., Ocala, FL 34481
$419,000

2 beds

|

2 baths

|

1,983 sq ft

|

House

9342 SW 102ND TERRACE RD, OCALA, FL, 344...
Community: On Top of the World
On Top of the World 8552 SW 92ND LN D, OCALA, FL, 34481, Ocala, FL 34481
$175,000

2 beds

|

2 baths

|

1,687 sq ft

|

Villa

8552 SW 92ND LN D, OCALA, FL, 34481
Community: On Top of the World
Lake Ashton 1394 OAKMONT DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$565,000

3 beds

|

2 baths

|

2,606 sq ft

|

House

1394 OAKMONT DR, WINTER HAVEN, FL, 33884
Community: Lake Ashton
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.
Kings Ridge 2409 TWICKINGHAM CT, CLERMONT, FL, 34711, Clermont, FL 34711
$405,000

3 beds

|

2 baths

|

2,033 sq ft

|

House

2409 TWICKINGHAM CT, CLERMONT, FL, 34711
Community: Kings Ridge
Marion Landing 8447 SW 60TH CT, OCALA, FL, 34476, Ocala, FL 34476
$295,000

3 beds

|

2 baths

|

1,706 sq ft

|

House

8447 SW 60TH CT, OCALA, FL, 34476
Community: Marion Landing
Arlington Ridge 4314 ARLINGTON RIDGE BLVD, LEESBURG, FL,..., Leesburg, FL 34748
$335,000

2 beds

|

2 baths

|

1,824 sq ft

|

House

4314 ARLINGTON RIDGE BLVD, LEESBURG, FL,...
Community: Arlington Ridge
Oak Run 10833 SW 86TH TER, OCALA, FL, 34481, Ocala, FL 34481
$220,000

3 beds

|

2 baths

|

1,620 sq ft

|

House

10833 SW 86TH TER, OCALA, FL, 34481
Community: Oak Run
Thunderbird Hill 3718 THUNDERBIRD HILL CIR, SEBRING, FL, ..., Sebring, FL 33872
$195,000

2 beds

|

2 baths

|

1,242 sq ft

|

Halfplex

3718 THUNDERBIRD HILL CIR, SEBRING, FL, ...
Community: Thunderbird Hill
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Stone Creek 9761 SW 74TH PL, OCALA, FL, 34481, Ocala, FL 34481
$520,000

3 beds

|

3 baths

|

2,530 sq ft

|

House

9761 SW 74TH PL, OCALA, FL, 34481
Community: Stone Creek
The Villages® 1205 DUSTIN DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$239,900

2 beds

|

2 baths

|

1,270 sq ft

|

Manufactured Home

1205 DUSTIN DR, LADY LAKE, FL, 32159
Community: The Villages®
SummerGlen 15813 SW 16TH AVENUE RD, OCALA, FL, 3447..., Ocala, FL 34473
$289,800

2 beds

|

2 baths

|

1,757 sq ft

|

House

15813 SW 16TH AVENUE RD, OCALA, FL, 3447...
Community: SummerGlen
Sun City Center 1905 CANTERBURY LN UNIT 17, SUN CITY CEN..., Sun City Center, FL 33573
$149,000

2 beds

|

2 baths

|

960 sq ft

|

Condo

1905 CANTERBURY LN UNIT 17, SUN CITY CEN...
Community: Sun City Center
The Villages® 2003 CORDERO CT, THE VILLAGES, FL, 32159, The Villages, FL 32159
$305,000

2 beds

|

2 baths

|

1,150 sq ft

|

House

2003 CORDERO CT, THE VILLAGES, FL, 32159
Community: The Villages®
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.
Highland Fairways 2085 LONG BOAT DR, LAKELAND, FL, 33810, Lakeland, FL 33810
$219,000

2 beds

|

2 baths

|

1,512 sq ft

|

House

2085 LONG BOAT DR, LAKELAND, FL, 33810
Community: Highland Fairways
On Top of the World 8625 SW 94TH LN A, OCALA, FL, 34481, Ocala, FL 34481
$154,900

2 beds

|

2 baths

|

1,484 sq ft

|

Villa

8625 SW 94TH LN A, OCALA, FL, 34481
Community: On Top of the World
Sun City Center 1326 IDLEWOOD DR, SUN CITY CENTER, FL, 3..., Sun City Center, FL 33573
$199,900

2 beds

|

2 baths

|

1,642 sq ft

|

Condo

1326 IDLEWOOD DR, SUN CITY CENTER, FL, 3...
Community: Sun City Center
The Lakes at Harmony 7465 WING SPAN WAY, HARMONY, FL, 34773, Harmony, FL 34773
$499,000

4 beds

|

3 baths

|

2,289 sq ft

|

House

7465 WING SPAN WAY, HARMONY, FL, 34773
Scottish Highlands 74 STONE HAVEN CT, LEESBURG, FL, 34788, Leesburg, FL 34788
$170,000

2 beds

|

2 baths

|

1,104 sq ft

|

House

74 STONE HAVEN CT, LEESBURG, FL, 34788
Community: Scottish Highlands
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
On Top of the World 8711 SW 96TH LN D, OCALA, FL, 34481, Ocala, FL 34481
$175,500

2 beds

|

2 baths

|

1,341 sq ft

|

Villa

8711 SW 96TH LN D, OCALA, FL, 34481
Community: On Top of the World
Traditions at Lake Ruby 3926 BEDFORD AVE, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$330,000

3 beds

|

2 baths

|

1,860 sq ft

|

House

3926 BEDFORD AVE, WINTER HAVEN, FL, 3388...
Ocala Preserve 5430 NW 35TH LANE RD, OCALA, FL, 34482, Ocala, FL 34482
$650,000

3 beds

|

3 baths

|

2,694 sq ft

|

House

5430 NW 35TH LANE RD, OCALA, FL, 34482
Community: Ocala Preserve
Harbor Hills Country Club 5090 GREENS DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$649,000

4 beds

|

3 baths

|

2,531 sq ft

|

House

5090 GREENS DR, LADY LAKE, FL, 32159
Stone Creek 7262 SW 94TH AVE, OCALA, FL, 34481, Ocala, FL 34481
$419,000

3 beds

|

2 baths

|

2,122 sq ft

|

House

7262 SW 94TH AVE, OCALA, FL, 34481
Community: Stone Creek

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3,573 homes near Winter Garden
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