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

3,964 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) 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
$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
Tampa Bay Golf and Country Club 29436 ZELLER AVE, SAN ANTONIO, FL, 33576, San Antonio, FL 33576
$249,900

2 beds

|

2 baths

|

1,124 sq ft

|

House

29436 ZELLER AVE, SAN ANTONIO, FL, 33576
The Villages® 1408 TORREY PINES DR, LADY LAKE, FL, 321..., Lady Lake, FL 32159
$179,000

2 beds

|

2 baths

|

1,144 sq ft

|

Manufactured Home

1408 TORREY PINES DR, LADY LAKE, FL, 321...
Community: The Villages®
Lake Jovita Golf and Country Club 13953 THOROUGHBRED DR, DADE CITY, FL, 33..., Dade City, FL 33525
$614,900

4 beds

|

3 baths

|

2,623 sq ft

|

House

13953 THOROUGHBRED DR, DADE CITY, FL, 33...
Arlington Ridge 26747 WHITE PLAINS WAY, LEESBURG, FL, 34..., Leesburg, FL 34748
$432,000

4 beds

|

2 baths

|

2,004 sq ft

|

House

26747 WHITE PLAINS WAY, LEESBURG, FL, 34...
Community: Arlington Ridge
The Villages® 482 HILDALGO DR, THE VILLAGES, FL, 32159, The Villages, FL 32159
$217,500

1 beds

|

1 baths

|

810 sq ft

|

Villa

482 HILDALGO DR, THE VILLAGES, FL, 32159
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 12455 SE 92ND TER, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$239,000

2 beds

|

2 baths

|

1,422 sq ft

|

House

12455 SE 92ND TER, SUMMERFIELD, FL, 3449...
Lake Jovita Golf and Country Club 13550 THOROUGHBRED DR, DADE CITY, FL, 33..., Dade City, FL 33525
$649,000

3 beds

|

3 baths

|

2,945 sq ft

|

House

13550 THOROUGHBRED DR, DADE CITY, FL, 33...
Summer Trees 6009 HICKORY GROVE LN, PORT ORANGE, FL, ..., Port Orange, FL 32128
$365,000

3 beds

|

2 baths

|

1,366 sq ft

|

House

6009 HICKORY GROVE LN, PORT ORANGE, FL, ...
Community: Summer Trees
On Top of the World 8412 SW 93RD CIR, OCALA, FL, 34481, Ocala, FL 34481
$530,000

2 beds

|

2 baths

|

2,103 sq ft

|

House

8412 SW 93RD CIR, OCALA, FL, 34481
Community: On Top of the World
The Villages® 1726 AUGUSTINE DR, THE VILLAGES, FL, 321..., The Villages, FL 32159
$579,000

3 beds

|

2 baths

|

2,236 sq ft

|

House

1726 AUGUSTINE DR, THE VILLAGES, FL, 321...
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.
Lakeside Landings 10173 JULIA ISLES AVE, OXFORD, FL, 34484, Oxford, FL 34484
$399,900

3 beds

|

2 baths

|

2,149 sq ft

|

House

10173 JULIA ISLES AVE, OXFORD, FL, 34484
Community: Lakeside Landings
Sun City Center 1506 BENTWOOD DR, SUN CITY CENTER, FL, 3..., Sun City Center, FL 33573
$374,900

2 beds

|

2 baths

|

1,756 sq ft

|

House

1506 BENTWOOD DR, SUN CITY CENTER, FL, 3...
Community: Sun City Center
Sun City Center 2222 GREENHAVEN DR, SUN CITY CENTER, FL,..., Sun City Center, FL 33573
$162,000

2 beds

|

2 baths

|

984 sq ft

|

Condo

2222 GREENHAVEN DR, SUN CITY CENTER, FL,...
Community: Sun City Center
Cherrywood 10237 SW 63RD AVE, OCALA, FL, 34476, Ocala, FL 34476
$269,900

3 beds

|

2 baths

|

1,497 sq ft

|

House

10237 SW 63RD AVE, OCALA, FL, 34476
Community: Cherrywood
Highland Fairways 3341 HIGHLAND FAIRWAYS BLVD, LAKELAND, F..., Lakeland, FL 33810
$239,900

2 beds

|

2 baths

|

1,235 sq ft

|

House

3341 HIGHLAND FAIRWAYS BLVD, LAKELAND, F...
Community: Highland Fairways
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Stone Creek 9277 SW 70TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$659,900

3 beds

|

3 baths

|

2,673 sq ft

|

House

9277 SW 70TH LOOP, OCALA, FL, 34481
Community: Stone Creek
Stonecrest 11120 SE 168TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491
$505,000

3 beds

|

2 baths

|

2,357 sq ft

|

House

11120 SE 168TH LOOP, SUMMERFIELD, FL, 34...
Community: Stonecrest
The Villages® 2523 MARIEL WAY, THE VILLAGES, FL, 32162, The Villages, FL 32162
$291,000

2 beds

|

2 baths

|

1,188 sq ft

|

Villa

2523 MARIEL WAY, THE VILLAGES, FL, 32162
Community: The Villages®
Sun City Center 2202 CLUBHOUSE DR UNIT 173, SUN CITY CEN..., Sun City Center, FL 33573
$135,000

2 beds

|

2 baths

|

984 sq ft

|

Condo

2202 CLUBHOUSE DR UNIT 173, SUN CITY CEN...
Community: Sun City Center
Sun City Center 1318 LELAND DR, SUN CITY CENTER, FL, 335..., Sun City Center, FL 33573
$274,900

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.
Spruce Creek North 10980 SW 62ND AVENUE RD, OCALA, FL, 3447..., Ocala, FL 34476
$201,500

3 beds

|

2 baths

|

1,526 sq ft

|

House

10980 SW 62ND AVENUE RD, OCALA, FL, 3447...
Community: Spruce Creek North
Esplanade at Wiregrass Ranch 29912 RUSCO CT, WESLEY CHAPEL, FL, 33543, Wesley Chapel, FL 33543
$694,999

3 beds

|

3 baths

|

2,397 sq ft

|

House

29912 RUSCO CT, WESLEY CHAPEL, FL, 33543
Esplanade at Wiregrass Ranch 4504 ISONZO WAY, WESLEY CHAPEL, FL, 3354..., Wesley Chapel, FL 33543
$709,999

3 beds

|

3 baths

|

2,275 sq ft

|

House

4504 ISONZO WAY, WESLEY CHAPEL, FL, 3354...
Esplanade at Wiregrass Ranch 29516 ZUPETTA LN, WESLEY CHAPEL, FL, 335..., Wesley Chapel, FL 33543
$449,999

3 beds

|

2 baths

|

1,925 sq ft

|

House

29516 ZUPETTA LN, WESLEY CHAPEL, FL, 335...
Stonecrest 11019 SE 170TH LANE RD, SUMMERFIELD, FL,..., Summerfield, FL 34491
$311,900

3 beds

|

2 baths

|

1,324 sq ft

|

House

11019 SE 170TH LANE RD, SUMMERFIELD, FL,...
Community: Stonecrest
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Heritage Hills 3618 SOLANA CIR, CLERMONT, FL, 34711, Clermont, FL 34711
$445,000

4 beds

|

3 baths

|

2,293 sq ft

|

House

3618 SOLANA CIR, CLERMONT, FL, 34711
Community: Heritage Hills
The Villages® 807 OAK BLVD, WILDWOOD, FL, 34785, Wildwood, FL 34785
$135,000

2 beds

|

2 baths

|

1,430 sq ft

|

Manufactured Home

807 OAK BLVD, WILDWOOD, FL, 34785
Community: The Villages®
Oak Run 8947 SW 115TH ST, OCALA, FL, 34481, Ocala, FL 34481
$189,000

2 beds

|

2 baths

|

1,050 sq ft

|

House

8947 SW 115TH ST, OCALA, FL, 34481
Community: Oak Run
Plantation at Leesburg 25517 LAUREL VALLEY RD, LEESBURG, FL, 34..., Leesburg, FL 34748
$419,900

3 beds

|

2 baths

|

2,381 sq ft

|

House

25517 LAUREL VALLEY RD, LEESBURG, FL, 34...
Quail Meadow 3275 NW 44TH CT, OCALA, FL, 34482, Ocala, FL 34482
$219,900

3 beds

|

2 baths

|

1,224 sq ft

|

House

3275 NW 44TH CT, OCALA, FL, 34482
Community: Quail Meadow
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.
Lake Jovita Golf and Country Club 13216 LEGENDS TRL, DADE CITY, FL, 33525, Dade City, FL 33525
$775,000

5 beds

|

3 baths

|

3,265 sq ft

|

House

13216 LEGENDS TRL, DADE CITY, FL, 33525
Latitude Margaritaville 817 MARGARITAVILLE AVE, DAYTONA BEACH, F..., Daytona Beach, FL 32124
$449,900

2 beds

|

2 baths

|

1,509 sq ft

|

House

817 MARGARITAVILLE AVE, DAYTONA BEACH, F...
The Villages® 1309 CAROLINA CT, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$449,900

3 beds

|

2 baths

|

1,894 sq ft

|

House

1309 CAROLINA CT, THE VILLAGES, FL, 3216...
Community: The Villages®
Del Webb Sunbridge 6129 CITRUS GROVE CT, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34771
$539,950

3 beds

|

3 baths

|

2,077 sq ft

|

House

6129 CITRUS GROVE CT, SAINT CLOUD, FL, 3...
Community: Del Webb Sunbridge
Sun City Center 2029 INVERNESS GREENS DR # 2029, SUN CIT..., Sun City Center, FL 33573
$245,000

2 beds

|

2 baths

|

1,188 sq ft

|

Condo

2029 INVERNESS GREENS DR # 2029, SUN CIT...
Community: Sun City Center
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
SummerGlen 15596 SW 13TH CIR, OCALA, FL, 34473, Ocala, FL 34473
$324,900

3 beds

|

2 baths

|

1,806 sq ft

|

House

15596 SW 13TH CIR, OCALA, FL, 34473
Community: SummerGlen
Twin Lakes 2482 YELLOW BRICK RD, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34772
$304,900

2 beds

|

2 baths

|

1,346 sq ft

|

Villa

2482 YELLOW BRICK RD, SAINT CLOUD, FL, 3...
Community: Twin Lakes
Sun City Center 1805 COLUMBINE PL, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$359,750

2 beds

|

2 baths

|

1,756 sq ft

|

House

1805 COLUMBINE PL, SUN CITY CENTER, FL, ...
Community: Sun City Center
Royal Highlands 21529 PRINCE ALBERT CT, LEESBURG, FL, 34..., Leesburg, FL 34748
$300,000

3 beds

|

2 baths

|

1,974 sq ft

|

House

21529 PRINCE ALBERT CT, LEESBURG, FL, 34...
Community: Royal Highlands
Sun City Center 2003 HALMROCK PL, SUN CITY CENTER, FL, 3..., Sun City Center, FL 33573
$198,000

2 beds

|

2 baths

|

1,150 sq ft

|

Condo

2003 HALMROCK PL, SUN CITY CENTER, FL, 3...
Community: Sun City Center

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3,964 homes near Winter Garden
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