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

3,537 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 - $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 - $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 - $600Ks
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 - $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 - $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
$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 - $600Ks
Twin Lakes, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes
Pelican Bay Daytona Beach
$100Ks - $400Ks
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, FL? 55places can help!
Questions? Call us: (689) 407-5757
4.7 rating (3 reviews) Spruce Creek South
$100Ks - $400Ks
Spruce Creek South, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1989 - 1995 | 1,650 homes
4.7 rating (11 reviews) Valencia Lakes
$200Ks - $700Ks
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
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 - $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
$300Ks - $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, FL? 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 - $400Ks
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
Breakaway Trails
$400Ks - $800Ks
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, FL? 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
4.4 rating (16 reviews) Del Webb Orlando
$300Ks - $400Ks
Del Webb Orlando, Davenport, FL
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes
Pine Run Estates
$100Ks - $300Ks
Pine Run Estates, Ocala, FL
Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 homes
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
Esplanade at Wiregrass Ra...
$400Ks - $1Ms
Esplanade at Wiregrass Ra..., Wesley Chapel, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 868 homes
New Pennbrooke Fairways 507 COTTAGE PARK LN, LEESBURG, FL, 34748, Leesburg, FL 34748
$173,000

2 beds

|

1 baths

|

708 sq ft

|

House

507 COTTAGE PARK LN, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Del Webb Oasis 15514 ORCHID ROSE CT, WINTER GARDEN, FL,..., Winter Garden, FL 34787
$707,070

2 beds

|

2 baths

|

1,943 sq ft

|

House

15514 ORCHID ROSE CT, WINTER GARDEN, FL,...
Community: Del Webb Oasis
Del Webb Oasis 15837 GEM VIEW ST, WINTER GARDEN, FL, 34..., Winter Garden, FL 34787
$455,410

2 beds

|

2 baths

|

1,579 sq ft

|

Villa

15837 GEM VIEW ST, WINTER GARDEN, FL, 34...
Community: Del Webb Oasis
The Villages® 7326 SE 173RD ARLINGTON LOOP, THE VILLAG..., The Villages, FL 32162
$324,900

3 beds

|

2 baths

|

1,490 sq ft

|

House

7326 SE 173RD ARLINGTON LOOP, THE VILLAG...
Community: The Villages®
New Windermere 823 BALMORAL CT, INVERNESS, FL, 34453, Inverness, FL 34453
$330,000

3 beds

|

3 baths

|

2,047 sq ft

|

House

823 BALMORAL CT, INVERNESS, FL, 34453
Community: Windermere
Want to learn more about 55+ communities in Winter Garden, FL? 55places can help!
Questions? Call us: (689) 407-5757
Windermere 802 WINDERMERE BLVD, INVERNESS, FL, 3445..., Inverness, FL 34453
$210,000

2 beds

|

2 baths

|

1,284 sq ft

|

House

802 WINDERMERE BLVD, INVERNESS, FL, 3445...
Community: Windermere
Palms at Serenoa 3441 MEADOW BEAUTY WAY, CLERMONT, FL, 34..., Clermont, FL 34714
$340,900

2 beds

|

2 baths

|

1,646 sq ft

|

Villa

3441 MEADOW BEAUTY WAY, CLERMONT, FL, 34...
Community: Palms at Serenoa
VillageWalk at Lake Nona 12026 AUTUMN FERN LN, ORLANDO, FL, 32827, Orlando, FL 32827
$699,000

3 beds

|

3 baths

|

3,015 sq ft

|

House

12026 AUTUMN FERN LN, ORLANDO, FL, 32827
The Villages® 2895 APACHE CT, THE VILLAGES, FL, 32163, The Villages, FL 32163
$449,900

3 beds

|

2 baths

|

1,865 sq ft

|

House

2895 APACHE CT, THE VILLAGES, FL, 32163
Community: The Villages®
Pelican Bay Daytona Beach 116 DUCK HAWK CIR 3040, DAYTONA BEACH, F..., Daytona Beach, FL 32119
$227,000

2 beds

|

2 baths

|

1,467 sq ft

|

Halfplex

116 DUCK HAWK CIR 3040, DAYTONA BEACH, F...
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.
Royal Highlands 21523 QUEEN ANNE CT, LEESBURG, FL, 34748, Leesburg, FL 34748
$259,000

3 beds

|

2 baths

|

1,671 sq ft

|

House

21523 QUEEN ANNE CT, LEESBURG, FL, 34748
Community: Royal Highlands
The Villages® 1514 E SCHWARTZ BLVD, LADY LAKE, FL, 321..., Lady Lake, FL 32159
$234,500

2 beds

|

2 baths

|

1,248 sq ft

|

Manufactured Home

1514 E SCHWARTZ BLVD, LADY LAKE, FL, 321...
Community: The Villages®
Royal Highlands 5025 ST ANDREWS ARC, LEESBURG, FL, 34748, Leesburg, FL 34748
$315,000

3 beds

|

2 baths

|

1,995 sq ft

|

House

5025 ST ANDREWS ARC, LEESBURG, FL, 34748
Community: Royal Highlands
Cresswind at Victoria Gardens 1631 VICTORIA GARDENS DR, DELAND, FL, 32..., Deland, FL 32724
$429,900

3 beds

|

2 baths

|

2,240 sq ft

|

House

1631 VICTORIA GARDENS DR, DELAND, FL, 32...
The Villages® 791 ENISGROVE WAY, THE VILLAGES, FL, 321..., The Villages, FL 32163
$465,000

3 beds

|

2 baths

|

1,956 sq ft

|

House

791 ENISGROVE WAY, THE VILLAGES, FL, 321...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden, FL? 55places can help!
Questions? Call us: (689) 407-5757
Liberty Village 7796 SW 74TH LP LP, OCALA, FL, 34481, Ocala, FL 34481
$295,000

3 beds

|

2 baths

|

1,755 sq ft

|

House

7796 SW 74TH LP LP, OCALA, FL, 34481
Community: Liberty Village
Liberty Village 7796 SW 74TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$295,000

3 beds

|

2 baths

|

1,755 sq ft

|

House

7796 SW 74TH LOOP, OCALA, FL, 34481
Community: Liberty Village
Stonecrest 11584 SE 175TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$319,000

2 beds

|

2 baths

|

1,702 sq ft

|

House

11584 SE 175TH ST, SUMMERFIELD, FL, 3449...
Community: Stonecrest
The Villages® 964 KINGMONT TER, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$339,900

2 beds

|

2 baths

|

1,142 sq ft

|

House

964 KINGMONT TER, THE VILLAGES, FL, 3216...
Community: The Villages®
The Villages® 17694 SE 84TH PEYTON CT, THE VILLAGES, F..., The Villages, FL 32162
$399,000

3 beds

|

2 baths

|

1,607 sq ft

|

Villa

17694 SE 84TH PEYTON CT, THE VILLAGES, F...
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.
The Villages® 7796 SE 168TH LONE OAK LOOP, THE VILLAGE..., The Villages, FL 32162
$339,900

3 beds

|

2 baths

|

1,540 sq ft

|

House

7796 SE 168TH LONE OAK LOOP, THE VILLAGE...
Community: The Villages®
The Villages® 3024 MACON CT, THE VILLAGES, FL, 32162, The Villages, FL 32162
$299,900

2 beds

|

2 baths

|

1,270 sq ft

|

Villa

3024 MACON CT, THE VILLAGES, FL, 32162
Community: The Villages®
Solivita 308 VESTRELLA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$285,000

2 beds

|

2 baths

|

1,703 sq ft

|

House

308 VESTRELLA DR, KISSIMMEE, FL, 34759
Community: Solivita
The Villages® 611 ALLENWOOD LOOP, THE VILLAGES, FL, 32..., The Villages, FL 32162
$429,999

3 beds

|

2 baths

|

1,927 sq ft

|

House

611 ALLENWOOD LOOP, THE VILLAGES, FL, 32...
Community: The Villages®
Majestic Oaks Ocala 5365 SW 86TH PL, OCALA, FL, 34476, Ocala, FL 34476
$375,000

3 beds

|

3 baths

|

2,678 sq ft

|

House

5365 SW 86TH PL, OCALA, FL, 34476
Community: Majestic Oaks Ocala
Want to learn more about 55+ communities in Winter Garden, FL? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 17235 SE 93RD DEMOSS CT, THE VILLAGES, F..., The Villages, FL 32162
$259,000

2 beds

|

2 baths

|

1,198 sq ft

|

Villa

17235 SE 93RD DEMOSS CT, THE VILLAGES, F...
Community: The Villages®
Venetian Bay 461 LUNA BELLA LN, NEW SMYRNA BEACH, FL,..., New Smyrna Beach, FL 32168
$625,000

3 beds

|

2 baths

|

2,002 sq ft

|

House

461 LUNA BELLA LN, NEW SMYRNA BEACH, FL,...
Community: Venetian Bay
Solivita 601 GRAND CANAL DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$239,239

2 beds

|

2 baths

|

1,258 sq ft

|

House

601 GRAND CANAL DR, KISSIMMEE, FL, 34759
Community: Solivita
Sun City Center 2329 LANCASTER DR, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$200,000

2 beds

|

2 baths

|

1,829 sq ft

|

Condo

2329 LANCASTER DR, SUN CITY CENTER, FL, ...
Community: Sun City Center
The Villages® 2003 CORDERO CT, THE VILLAGES, FL, 32159, The Villages, FL 32159
$275,000

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.
On Top of the World 8231 SW 79TH CT, OCALA, FL, 34476, Ocala, FL 34476
$275,000

3 beds

|

2 baths

|

1,963 sq ft

|

House

8231 SW 79TH CT, OCALA, FL, 34476
Community: On Top of the World
VillageWalk at Lake Nona 12048 TALITHA LN, ORLANDO, FL, 32827, Orlando, FL 32827
$480,000

3 beds

|

3 baths

|

1,830 sq ft

|

Townhouse

12048 TALITHA LN, ORLANDO, FL, 32827
The Villages® 2361 INDIA HOOK TER, THE VILLAGES, FL, 3..., The Villages, FL 32162
$539,000

3 beds

|

2 baths

|

2,444 sq ft

|

House

2361 INDIA HOOK TER, THE VILLAGES, FL, 3...
Community: The Villages®
New The Villages® 13651 COUNTY ROAD 109H, LADY LAKE, FL, 3..., Lady Lake, FL 32159
$199,000

3 beds

|

2 baths

|

1,456 sq ft

|

Manufactured Home

13651 COUNTY ROAD 109H, LADY LAKE, FL, 3...
Community: The Villages®
Ocala Palms 5063 NW 18TH ST, OCALA, FL, 34482, Ocala, FL 34482
$219,000

2 beds

|

2 baths

|

1,207 sq ft

|

House

5063 NW 18TH ST, OCALA, FL, 34482
Community: Ocala Palms
Want to learn more about 55+ communities in Winter Garden, FL? 55places can help!
Questions? Call us: (689) 407-5757
Tampa Bay Golf and Country Club 9448 ROLLING CIR, SAN ANTONIO, FL, 33576, San Antonio, FL 33576
$320,000

3 beds

|

3 baths

|

1,577 sq ft

|

House

9448 ROLLING CIR, SAN ANTONIO, FL, 33576
The Villages® 912 VENTURA DR, THE VILLAGES, FL, 32159, The Villages, FL 32159
$360,000

3 beds

|

2 baths

|

2,046 sq ft

|

House

912 VENTURA DR, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 632 DELGADO AVE, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$399,900

2 beds

|

2 baths

|

1,139 sq ft

|

Villa

632 DELGADO AVE, LADY LAKE, FL, 32159
Community: The Villages®
The Villages® 17979 SE 89TH ROTHWAY CT, THE VILLAGES, ..., The Villages, FL 32162
$369,900

3 beds

|

2 baths

|

1,855 sq ft

|

House

17979 SE 89TH ROTHWAY CT, THE VILLAGES, ...
Community: The Villages®
Foxwood Lake Estates 1560 LONGBOW DR, LAKELAND, FL, 33810, Lakeland, FL 33810
$160,000

2 beds

|

2 baths

|

1,040 sq ft

|

Manufactured Home

1560 LONGBOW DR, LAKELAND, FL, 33810

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3,537 homes near Winter Garden
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