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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
Lakes of Mount Dora 8252 BRIDGEPORT BAY CIR, MOUNT DORA, FL,..., Mount Dora, FL 32757
$385,000

3 beds

|

2 baths

|

1,473 sq ft

|

House

8252 BRIDGEPORT BAY CIR, MOUNT DORA, FL,...
Community: Lakes of Mount Dora
Solivita 540 GENOA DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$329,900

3 beds

|

2 baths

|

1,817 sq ft

|

House

540 GENOA DR, POINCIANA, FL, 34759
Community: Solivita
Palm Cay 8274 SW 106TH PL, OCALA, FL, 34481, Ocala, FL 34481
$161,000

2 beds

|

1 baths

|

768 sq ft

|

House

8274 SW 106TH PL, OCALA, FL, 34481
Community: Palm Cay
Carlsberg Estates on Lake Suzanne 284 LAKE SUZANNE DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859
$229,900

2 beds

|

2 baths

|

1,170 sq ft

|

House

284 LAKE SUZANNE DR, LAKE WALES, FL, 338...
The Villages® 3540 OBRIEN PL, THE VILLAGES, FL, 32163, The Villages, FL 32163
$549,900

3 beds

|

3 baths

|

2,293 sq ft

|

House

3540 OBRIEN PL, THE VILLAGES, FL, 32163
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Carlsberg Estates on Lake Suzanne 496 LAKE SUZANNE DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859
$345,000

2 beds

|

2 baths

|

1,637 sq ft

|

House

496 LAKE SUZANNE DR, LAKE WALES, FL, 338...
Quail Meadow 3220 NW 46TH CT, OCALA, FL, 34482, Ocala, FL 34482
$250,000

2 beds

|

2 baths

|

1,381 sq ft

|

House

3220 NW 46TH CT, OCALA, FL, 34482
Community: Quail Meadow
Harbor Hills Country Club 39517 HILLRISE LN, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$549,900

4 beds

|

3 baths

|

2,532 sq ft

|

House

39517 HILLRISE LN, LADY LAKE, FL, 32159
Ocala Palms 5063 NW 18TH ST, OCALA, FL, 34482, Ocala, FL 34482
$232,900

2 beds

|

2 baths

|

1,207 sq ft

|

House

5063 NW 18TH ST, OCALA, FL, 34482
Community: Ocala Palms
Breakaway Trails 24 LAKE VISTA WAY, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$509,900

4 beds

|

3 baths

|

2,544 sq ft

|

House

24 LAKE VISTA WAY, ORMOND BEACH, FL, 321...
Community: Breakaway Trails
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 9053 SW 103RD AVE, OCALA, FL, 34481, Ocala, FL 34481
$295,900

2 beds

|

2 baths

|

1,766 sq ft

|

House

9053 SW 103RD AVE, OCALA, FL, 34481
Community: On Top of the World
The Villages® 17602 SE 82ND WOODLAWN AVE, THE VILLAGES..., The Villages, FL 32162
$465,999

3 beds

|

2 baths

|

1,924 sq ft

|

House

17602 SE 82ND WOODLAWN AVE, THE VILLAGES...
Community: The Villages®
Sun City Center 305 CRANSTON PL, SUN CITY CENTER, FL, 33..., Sun City Center, FL 33573
$263,000

2 beds

|

2 baths

|

1,718 sq ft

|

House

305 CRANSTON PL, SUN CITY CENTER, FL, 33...
Community: Sun City Center
VillageWalk at Lake Nona 11920 KAJETAN LN, ORLANDO, FL, 32827, Orlando, FL 32827
$450,000

2 beds

|

2 baths

|

1,708 sq ft

|

Halfplex

11920 KAJETAN LN, ORLANDO, FL, 32827
Spruce Creek Preserve 14117 SW 115TH CIR, DUNNELLON, FL, 34432, Dunnellon, FL 34432
$215,000

2 beds

|

2 baths

|

1,296 sq ft

|

House

14117 SW 115TH CIR, DUNNELLON, FL, 34432
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Sun City Center 951 VILLEROY GREENS DR, SUN CITY CENTER,..., Sun City Center, FL 33573
$329,900

2 beds

|

2 baths

|

1,855 sq ft

|

Condo

951 VILLEROY GREENS DR, SUN CITY CENTER,...
Community: Sun City Center
Del Webb Sunbridge 2522 CLIFF WAY, SAINT CLOUD, FL, 34771, Saint Cloud, FL 34771
$399,000

2 beds

|

2 baths

|

1,584 sq ft

|

Villa

2522 CLIFF WAY, SAINT CLOUD, FL, 34771
Community: Del Webb Sunbridge
Spruce Creek Country Club 12512 SE 91ST TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491
$374,900

2 beds

|

2 baths

|

2,130 sq ft

|

House

12512 SE 91ST TERRACE RD, SUMMERFIELD, F...
Spruce Creek Country Club 13863 SE 85TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$310,000

3 beds

|

2 baths

|

1,844 sq ft

|

House

13863 SE 85TH CIR, SUMMERFIELD, FL, 3449...
Sun City Center 1812 NEW BEDFORD DR, SUN CITY CENTER, FL..., Sun City Center, FL 33573
$449,900

3 beds

|

2 baths

|

2,606 sq ft

|

House

1812 NEW BEDFORD 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.
Pelican Bay Daytona Beach 101 BOB WHITE CT APT 1, DAYTONA BEACH, F..., Daytona Beach, FL 32119
$199,900

3 beds

|

3 baths

|

1,721 sq ft

|

Condo

101 BOB WHITE CT APT 1, DAYTONA BEACH, F...
Lake Jovita Golf and Country Club 13514 THOROUGHBRED DR, DADE CITY, FL, 33..., Dade City, FL 33525
$625,000

3 beds

|

2 baths

|

2,108 sq ft

|

House

13514 THOROUGHBRED DR, DADE CITY, FL, 33...
Solivita 340 SORRENTO RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$254,500

3 beds

|

2 baths

|

1,574 sq ft

|

House

340 SORRENTO RD, KISSIMMEE, FL, 34759
Community: Solivita
Stonecrest 11037 SE 173RD PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$295,000

3 beds

|

2 baths

|

1,328 sq ft

|

House

11037 SE 173RD PL, SUMMERFIELD, FL, 3449...
Community: Stonecrest
On Top of the World 9551 SW 92ND TER, OCALA, FL, 34481, Ocala, FL 34481
$299,900

2 beds

|

2 baths

|

1,745 sq ft

|

House

9551 SW 92ND TER, OCALA, FL, 34481
Community: On Top of the World
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Sun City Center 1503 N PEBBLE BEACH BLVD, SUN CITY CENTE..., Sun City Center, FL 33573
$205,000

2 beds

|

2 baths

|

1,704 sq ft

|

House

1503 N PEBBLE BEACH BLVD, SUN CITY CENTE...
Community: Sun City Center
Colonnades 4926 PLEASANT HOLLOW TRL, LAKELAND, FL, ..., Lakeland, FL 33811
$220,000

2 beds

|

2 baths

|

1,193 sq ft

|

House

4926 PLEASANT HOLLOW TRL, LAKELAND, FL, ...
Community: Colonnades
Colonnades 4940 COLONNADES CLUB BLVD, LAKELAND, FL,..., Lakeland, FL 33811
$215,000

2 beds

|

2 baths

|

1,087 sq ft

|

House

4940 COLONNADES CLUB BLVD, LAKELAND, FL,...
Community: Colonnades
The Villages® 14202 SANDALWOOD DR # 202, WILDWOOD, FL,..., Wildwood, FL 34785
$119,900

2 beds

|

2 baths

|

1,085 sq ft

|

Condo

14202 SANDALWOOD DR # 202, WILDWOOD, FL,...
Community: The Villages®
On Top of the World 9460 SW 86TH PL, OCALA, FL, 34481, Ocala, FL 34481
$635,990

3 beds

|

2 baths

|

2,648 sq ft

|

House

9460 SW 86TH PL, 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.
Sun City Center 2182 ACADIA GREENS DR # 66, SUN CITY CEN..., Sun City Center, FL 33573
$230,000

2 beds

|

2 baths

|

1,194 sq ft

|

Condo

2182 ACADIA GREENS DR # 66, SUN CITY CEN...
Community: Sun City Center
Sun City Center 202 BEDFORD ST 72, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$116,900

2 beds

|

2 baths

|

960 sq ft

|

Condo

202 BEDFORD ST 72, SUN CITY CENTER, FL, ...
Community: Sun City Center
Solivita 130 PRIMA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$410,000

3 beds

|

2 baths

|

2,141 sq ft

|

House

130 PRIMA DR, KISSIMMEE, FL, 34759
Community: Solivita
Spruce Creek Country Club 9573 SE 124TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$319,000

2 beds

|

2 baths

|

1,708 sq ft

|

House

9573 SE 124TH LOOP, SUMMERFIELD, FL, 344...
Sun City Center 1902 ANDOVER ST APT 203, SUN CITY CENTER..., Sun City Center, FL 33573
$107,900

1 beds

|

2 baths

|

800 sq ft

|

Condo

1902 ANDOVER ST APT 203, SUN CITY CENTER...
Community: Sun City Center
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Four Seasons at Orlando 1987 KEY BAY TRL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$349,900

2 beds

|

2 baths

|

1,437 sq ft

|

Villa

1987 KEY BAY TRL, KISSIMMEE, FL, 34747
Mirada 10282 ECHO DOCK LOOP, SAN ANTONIO, FL, 3..., San Antonio, FL 33576
$277,500

2 beds

|

2 baths

|

1,614 sq ft

|

Villa

10282 ECHO DOCK LOOP, SAN ANTONIO, FL, 3...
Community: Mirada
Valencia Lakes 16106 CEDAR KEY DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$535,000

4 beds

|

3 baths

|

2,467 sq ft

|

House

16106 CEDAR KEY DR, WIMAUMA, FL, 33598
Community: Valencia Lakes
Arlington Ridge 4110 ARLINGTON RIDGE BLVD, LEESBURG, FL,..., Leesburg, FL 34748
$389,900

4 beds

|

2 baths

|

1,857 sq ft

|

House

4110 ARLINGTON RIDGE BLVD, LEESBURG, FL,...
Community: Arlington Ridge
Tampa Bay Golf and Country Club 9506 ROLLING CIR, SAN ANTONIO, FL, 33576, San Antonio, FL 33576
$299,900

3 beds

|

3 baths

|

1,577 sq ft

|

House

9506 ROLLING CIR, SAN ANTONIO, FL, 33576

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3,648 homes near Winter Garden
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