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

3,648 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
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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 - $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
$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
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 - $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
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 | 1,024 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
Ocala Palms 4677 NW 51ST CT, OCALA, FL, 34482, Ocala, FL 34482
$399,990

4 beds

|

3 baths

|

2,345 sq ft

|

House

4677 NW 51ST CT, OCALA, FL, 34482
Community: Ocala Palms
Kings Ridge 2028 BRAXTON ST, CLERMONT, FL, 34711, Clermont, FL 34711
$279,900

2 beds

|

2 baths

|

1,170 sq ft

|

House

2028 BRAXTON ST, CLERMONT, FL, 34711
Community: Kings Ridge
On Top of the World 7834 SW 89TH CIR, OCALA, FL, 34481, Ocala, FL 34481
$316,900

2 beds

|

2 baths

|

1,469 sq ft

|

House

7834 SW 89TH CIR, OCALA, FL, 34481
Community: On Top of the World
Stonecrest 12300 SE 176TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491
$485,000

3 beds

|

2 baths

|

2,121 sq ft

|

House

12300 SE 176TH LOOP, SUMMERFIELD, FL, 34...
Community: Stonecrest
Pennbrooke Fairways 32831 TIMBERWOOD DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$318,000

3 beds

|

2 baths

|

1,757 sq ft

|

House

32831 TIMBERWOOD DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Solivita 890 BELLA VIANA RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$539,900

2 beds

|

3 baths

|

2,343 sq ft

|

House

890 BELLA VIANA RD, KISSIMMEE, FL, 34759
Community: Solivita
SummerGlen 15858 SW 11TH COURT RD, OCALA, FL, 34473, Ocala, FL 34473
$260,700

2 beds

|

2 baths

|

1,580 sq ft

|

House

15858 SW 11TH COURT RD, OCALA, FL, 34473
Community: SummerGlen
SummerGlen 15304 SW 15TH TERRACE RD, OCALA, FL, 344..., Ocala, FL 34473
$398,500

4 beds

|

3 baths

|

2,580 sq ft

|

House

15304 SW 15TH TERRACE RD, OCALA, FL, 344...
Community: SummerGlen
SummerGlen 15659 SW 13TH CIR, OCALA, FL, 34473, Ocala, FL 34473
$261,000

2 beds

|

2 baths

|

1,593 sq ft

|

House

15659 SW 13TH CIR, OCALA, FL, 34473
Community: SummerGlen
Sun City Center 1318 LELAND DR, SUN CITY CENTER, FL, 335..., Sun City Center, FL 33573
$269,900

2 beds

|

2 baths

|

1,755 sq ft

|

Condo

1318 LELAND DR, SUN CITY CENTER, FL, 335...
Community: Sun City Center
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 722 SHOREHAVEN DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$480,000

3 beds

|

3 baths

|

2,450 sq ft

|

House

722 SHOREHAVEN DR, KISSIMMEE, FL, 34759
Community: Solivita
Venetian Bay 434 VENETIAN PALMS BLVD, NEW SMYRNA BEAC..., New Smyrna Beach, FL 32168
$345,000

4 beds

|

3 baths

|

2,101 sq ft

|

House

434 VENETIAN PALMS BLVD, NEW SMYRNA BEAC...
Community: Venetian Bay
On Top of the World 8480 SW 92ND PL A, OCALA, FL, 34481, Ocala, FL 34481
$217,500

2 beds

|

2 baths

|

1,740 sq ft

|

Villa

8480 SW 92ND PL A, OCALA, FL, 34481
Community: On Top of the World
Stone Creek 6184 SW 89TH CT, OCALA, FL, 34481, Ocala, FL 34481
$499,900

2 beds

|

3 baths

|

2,110 sq ft

|

House

6184 SW 89TH CT, OCALA, FL, 34481
Community: Stone Creek
The Villages® 1497 ALEXANDRIA PL, THE VILLAGES, FL, 32..., The Villages, FL 32162
$344,500

2 beds

|

2 baths

|

1,132 sq ft

|

Villa

1497 ALEXANDRIA PL, THE VILLAGES, FL, 32...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Cherrywood 6071 SW 105TH PL, OCALA, FL, 34476, Ocala, FL 34476
$245,000

3 beds

|

2 baths

|

1,497 sq ft

|

House

6071 SW 105TH PL, OCALA, FL, 34476
Community: Cherrywood
The Lakes at Harmony 3436 SAGEBRUSH ST, HARMONY, FL, 34773, Harmony, FL 34773
$324,900

2 beds

|

2 baths

|

1,637 sq ft

|

House

3436 SAGEBRUSH ST, HARMONY, FL, 34773
Trilogy® Orlando 100 SILVER MAPLE RD, GROVELAND, FL, 3473..., Groveland, FL 34736
$420,000

3 beds

|

2 baths

|

1,564 sq ft

|

House

100 SILVER MAPLE RD, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
Oak Run 11127 SW 73RD CIR, OCALA, FL, 34476, Ocala, FL 34476
$313,900

3 beds

|

2 baths

|

2,016 sq ft

|

House

11127 SW 73RD CIR, OCALA, FL, 34476
Community: Oak Run
Sun City Center 382 CLUB MANOR DR, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$184,990

2 beds

|

2 baths

|

1,516 sq ft

|

Condo

382 CLUB MANOR DR, SUN CITY CENTER, FL, ...
Community: Sun City Center
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® 2630 CARIBE DR, THE VILLAGES, FL, 32162, The Villages, FL 32162
$374,900

3 beds

|

2 baths

|

1,674 sq ft

|

House

2630 CARIBE DR, THE VILLAGES, FL, 32162
Community: The Villages®
Lake Ashton 1124 SAWGRASS DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$395,000

3 beds

|

2 baths

|

2,113 sq ft

|

House

1124 SAWGRASS DR, WINTER HAVEN, FL, 3388...
Community: Lake Ashton
The Villages® 870 HENDERSON LN, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$329,900

3 beds

|

2 baths

|

1,375 sq ft

|

House

870 HENDERSON LN, THE VILLAGES, FL, 3216...
Community: The Villages®
Legacy of Leesburg 27302 STONEY BROOK DR, LEESBURG, FL, 347..., Leesburg, FL 34748
$279,999

3 beds

|

2 baths

|

1,478 sq ft

|

House

27302 STONEY BROOK DR, LEESBURG, FL, 347...
Community: Legacy of Leesburg
Harbor Hills Country Club 5066 GREENS DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$649,000

4 beds

|

3 baths

|

2,544 sq ft

|

House

5066 GREENS DR, LADY LAKE, FL, 32159
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
High Vista at Ridgewood Lakes 106 MOSSY OAK DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$360,000

3 beds

|

2 baths

|

1,797 sq ft

|

House

106 MOSSY OAK DR, DAVENPORT, FL, 33837
Latitude Margaritaville 171 CATAMARAN CV, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124
$949,900

3 beds

|

3 baths

|

2,468 sq ft

|

House

171 CATAMARAN CV, DAYTONA BEACH, FL, 321...
Harbor Hills Country Club 5556 GROVE MNR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$320,000

3 beds

|

2 baths

|

1,525 sq ft

|

House

5556 GROVE MNR, LADY LAKE, FL, 32159
Lake Ashton 4568 TURNBERRY LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$399,900

3 beds

|

2 baths

|

1,847 sq ft

|

House

4568 TURNBERRY LN, LAKE WALES, FL, 33859
Community: Lake Ashton
On Top of the World 9251 SW 94TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$359,900

3 beds

|

3 baths

|

2,412 sq ft

|

House

9251 SW 94TH LOOP, OCALA, FL, 34481
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.
Sandpiper Golf & Country Club 6098 MAGPIE DR, LAKELAND, FL, 33809, Lakeland, FL 33809
$349,900

3 beds

|

2 baths

|

2,006 sq ft

|

House

6098 MAGPIE DR, LAKELAND, FL, 33809
Sun City Center 821 CHIPPER DR, SUN CITY CENTER, FL, 335..., Sun City Center, FL 33573
$324,000

3 beds

|

2 baths

|

1,568 sq ft

|

Villa

821 CHIPPER DR, SUN CITY CENTER, FL, 335...
Community: Sun City Center
Arlington Ridge 27327 ROANOKE DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$385,000

3 beds

|

2 baths

|

1,712 sq ft

|

House

27327 ROANOKE DR, LEESBURG, FL, 34748
Community: Arlington Ridge
Spruce Creek North 10860 SW 62ND AVE, OCALA, FL, 34476, Ocala, FL 34476
$189,900

2 beds

|

2 baths

|

1,296 sq ft

|

House

10860 SW 62ND AVE, OCALA, FL, 34476
Community: Spruce Creek North
The Country Club of Mount Dora 1812 STAFFORD SPRINGS BLVD, MOUNT DORA, ..., Mount Dora, FL 32757
$374,500

2 beds

|

2 baths

|

1,515 sq ft

|

House

1812 STAFFORD SPRINGS BLVD, MOUNT DORA, ...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Carlsberg Estates on Lake Suzanne 4182 CANNES AVE, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$250,000

3 beds

|

3 baths

|

1,744 sq ft

|

House

4182 CANNES AVE, LAKE WALES, FL, 33859
On Top of the World 8711 SW 90TH ST B, OCALA, FL, 34481, Ocala, FL 34481
$140,000

2 beds

|

2 baths

|

1,096 sq ft

|

Villa

8711 SW 90TH ST B, OCALA, FL, 34481
Community: On Top of the World
Sun City Center 321 SIENA VISTA PL, SUN CITY CENTER, FL,..., Sun City Center, FL 33573
$385,000

3 beds

|

2 baths

|

2,021 sq ft

|

House

321 SIENA VISTA PL, SUN CITY CENTER, FL,...
Community: Sun City Center
On Top of the World 8798 SW 83RD CIR, OCALA, FL, 34481, Ocala, FL 34481
$370,000

3 beds

|

2 baths

|

2,145 sq ft

|

House

8798 SW 83RD CIR, OCALA, FL, 34481
Community: On Top of the World
The Villages® 17065 SE 79TH MCLAWREN TER, THE VILLAGES..., The Villages, FL 32162
$389,000

3 beds

|

2 baths

|

1,684 sq ft

|

House

17065 SE 79TH MCLAWREN TER, THE VILLAGES...
Community: The Villages®

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3,648 homes near Winter Garden
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