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

3,958 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.
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) Trilogy® Orlando
$200Ks - $600Ks
Trilogy® Orlando, Groveland, FL
Resale Only | 55+ age-restricted | Built 2005 - 2022 | 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
On Top of the World 8787 SW 90TH LN E, OCALA, FL, 34481, Ocala, FL 34481
$195,000

2 beds

|

2 baths

|

1,594 sq ft

|

Villa

8787 SW 90TH LN E, OCALA, FL, 34481
Community: On Top of the World
Oak Run 6836 SW 112TH ST, OCALA, FL, 34476, Ocala, FL 34476
$263,880

3 beds

|

2 baths

|

1,366 sq ft

|

House

6836 SW 112TH ST, OCALA, FL, 34476
Community: Oak Run
Cresswind at Victoria Gardens 112 OVERTON GARDENS LN, DELAND, FL, 3272..., Deland, FL 32724
$365,000

3 beds

|

2 baths

|

2,240 sq ft

|

House

112 OVERTON GARDENS LN, DELAND, FL, 3272...
Valencia Lakes 15644 AURORA LAKE CIR, WIMAUMA, FL, 3359..., Wimauma, FL 33598
$382,000

3 beds

|

2 baths

|

1,764 sq ft

|

Villa

15644 AURORA LAKE CIR, WIMAUMA, FL, 3359...
Community: Valencia Lakes
Sun City Center 1901 CANTERBURY LN 19, SUN CITY CENTER, ..., Sun City Center, FL 33573
$135,000

2 beds

|

2 baths

|

960 sq ft

|

Condo

1901 CANTERBURY LN 19, 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
JB Ranch 9238 SW 60TH TERRACE RD, OCALA, FL, 3447..., Ocala, FL 34476
$339,900

3 beds

|

2 baths

|

1,714 sq ft

|

House

9238 SW 60TH TERRACE RD, OCALA, FL, 3447...
Community: JB Ranch
On Top of the World 9764 SW 81ST LN, OCALA, FL, 34481, Ocala, FL 34481
$549,900

2 beds

|

2 baths

|

2,309 sq ft

|

House

9764 SW 81ST LN, OCALA, FL, 34481
Community: On Top of the World
Encore at Fishhawk Ranch 13915 KINGFISHER GLEN DR, LITHIA, FL, 33..., Lithia, FL 33547
$455,000

2 beds

|

2 baths

|

1,769 sq ft

|

House

13915 KINGFISHER GLEN DR, LITHIA, FL, 33...
Stonecrest 17126 SE 117TH CIR, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$699,000

3 beds

|

2 baths

|

2,508 sq ft

|

House

17126 SE 117TH CIR, SUMMERFIELD, FL, 344...
Community: Stonecrest
Royal Highlands 5906 PRINCE PHILIP CT, LEESBURG, FL, 347..., Leesburg, FL 34748
$349,900

3 beds

|

2 baths

|

1,951 sq ft

|

House

5906 PRINCE PHILIP CT, LEESBURG, FL, 347...
Community: Royal Highlands
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 South 9773 SE 179TH PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$319,900

3 beds

|

2 baths

|

2,093 sq ft

|

House

9773 SE 179TH PL, SUMMERFIELD, FL, 34491
Community: Spruce Creek South
Esplanade at Highland Ranch 1392 ZEEK RIDGE ST, CLERMONT, FL, 34715, Clermont, FL 34715
$555,000

2 beds

|

3 baths

|

2,166 sq ft

|

House

1392 ZEEK RIDGE ST, CLERMONT, FL, 34715
The Villages® 7474 SE 172ND FIELDCREST ST, THE VILLAGE..., The Villages, FL 32162
$314,900

3 beds

|

2 baths

|

1,490 sq ft

|

House

7474 SE 172ND FIELDCREST ST, THE VILLAGE...
Community: The Villages®
Quail Meadow 1795 NW 44TH COURT RD, OCALA, FL, 34482, Ocala, FL 34482
$379,900

5 beds

|

3 baths

|

2,445 sq ft

|

House

1795 NW 44TH COURT RD, OCALA, FL, 34482
Community: Quail Meadow
Trilogy® Orlando 117 FALLING ACORN AVE, GROVELAND, FL, 34..., Groveland, FL 34736
$329,000

2 beds

|

2 baths

|

1,434 sq ft

|

House

117 FALLING ACORN AVE, GROVELAND, FL, 34...
Community: Trilogy® Orlando
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Royal Harbor 3584 TROPICAL SEAS LOOP, TAVARES, FL, 32..., Tavares, FL 32778
$345,000

3 beds

|

2 baths

|

1,716 sq ft

|

House

3584 TROPICAL SEAS LOOP, TAVARES, FL, 32...
Community: Royal Harbor
Del Webb Sunbridge 6494 ROVER WAY, SAINT CLOUD, FL, 34771, Saint Cloud, FL 34771
$580,000

3 beds

|

2 baths

|

1,881 sq ft

|

House

6494 ROVER WAY, SAINT CLOUD, FL, 34771
Community: Del Webb Sunbridge
Plantation at Leesburg 25057 RIVERWALK DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$387,500

3 beds

|

3 baths

|

2,676 sq ft

|

House

25057 RIVERWALK DR, LEESBURG, FL, 34748
SummerGlen 1763 SW 155TH PLACE RD, OCALA, FL, 34473, Ocala, FL 34473
$405,000

3 beds

|

2 baths

|

2,093 sq ft

|

House

1763 SW 155TH PLACE RD, OCALA, FL, 34473
Community: SummerGlen
Royal Harbor 5676 GULF STREAM ST, TAVARES, FL, 32778, Tavares, FL 32778
$367,000

4 beds

|

3 baths

|

1,915 sq ft

|

House

5676 GULF STREAM ST, TAVARES, FL, 32778
Community: Royal Harbor
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.
Encore at Fishhawk Ranch 6002 THRUSHWOOD RD, LITHIA, FL, 33547, Lithia, FL 33547
$485,000

2 beds

|

2 baths

|

1,892 sq ft

|

House

6002 THRUSHWOOD RD, LITHIA, FL, 33547
Plantation at Leesburg 4724 SABLE RIDGE CT, LEESBURG, FL, 34748, Leesburg, FL 34748
$435,000

3 beds

|

3 baths

|

3,221 sq ft

|

House

4724 SABLE RIDGE CT, LEESBURG, FL, 34748
Encore at Fishhawk Ranch 6113 PLOVER MEADOW ST, LITHIA, FL, 33547, Lithia, FL 33547
$489,000

2 beds

|

2 baths

|

1,916 sq ft

|

House

6113 PLOVER MEADOW ST, LITHIA, FL, 33547
Venetian Bay 367 CARYOTA CT, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$422,000

3 beds

|

2 baths

|

1,653 sq ft

|

House

367 CARYOTA CT, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
Esplanade at Wiregrass Ranch 4639 GAROFALO RD, WESLEY CHAPEL, FL, 335..., Wesley Chapel, FL 33543
$450,000

3 beds

|

2 baths

|

1,689 sq ft

|

House

4639 GAROFALO RD, WESLEY CHAPEL, FL, 335...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Encore at Fishhawk Ranch 13939 SWALLOW HILL DR, LITHIA, FL, 33547, Lithia, FL 33547
$547,000

2 beds

|

3 baths

|

2,595 sq ft

|

House

13939 SWALLOW HILL DR, LITHIA, FL, 33547
On Top of the World 6677 SW 81ST LOOP, OCALA, FL, 34476, Ocala, FL 34476
$235,000

3 beds

|

3 baths

|

1,458 sq ft

|

Townhouse

6677 SW 81ST LOOP, OCALA, FL, 34476
Community: On Top of the World
The Villages® 2866 JUDAH ST, THE VILLAGES, FL, 32163, The Villages, FL 32163
$317,000

2 beds

|

2 baths

|

1,257 sq ft

|

House

2866 JUDAH ST, THE VILLAGES, FL, 32163
Community: The Villages®
Lakes of Mount Dora 8575 HEMPSTEAD WAY, MOUNT DORA, FL, 3275..., Mount Dora, FL 32757
$779,999

3 beds

|

3 baths

|

2,370 sq ft

|

House

8575 HEMPSTEAD WAY, MOUNT DORA, FL, 3275...
Community: Lakes of Mount Dora
Royal Highlands 5004 SAINT ANDREWS ARC, LEESBURG, FL, 34..., Leesburg, FL 34748
$284,900

2 beds

|

2 baths

|

1,483 sq ft

|

House

5004 SAINT ANDREWS ARC, LEESBURG, FL, 34...
Community: Royal Highlands
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.
Cresswind at Victoria Gardens 1374 RED CLOVER LN, DELAND, FL, 32724, Deland, FL 32724
$344,900

2 beds

|

2 baths

|

1,651 sq ft

|

House

1374 RED CLOVER LN, DELAND, FL, 32724
Lake Ashton 5357 HOGAN LN, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$534,400

3 beds

|

2 baths

|

2,363 sq ft

|

House

5357 HOGAN LN, WINTER HAVEN, FL, 33884
Community: Lake Ashton
Latitude Margaritaville 213 COMPASS ROSE DR, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$635,000

2 beds

|

2 baths

|

1,937 sq ft

|

House

213 COMPASS ROSE DR, DAYTONA BEACH, FL, ...
Sun City Center 1603 E DEL WEBB BLVD, SUN CITY CENTER, F..., Sun City Center, FL 33573
$280,000

2 beds

|

2 baths

|

1,379 sq ft

|

House

1603 E DEL WEBB BLVD, SUN CITY CENTER, F...
Community: Sun City Center
Pelican Bay Daytona Beach 149 BLUE HERON DR C, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119
$190,000

2 beds

|

2 baths

|

1,192 sq ft

|

Condo

149 BLUE HERON DR C, DAYTONA BEACH, FL, ...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Ocala Preserve 4687 NW 35TH LANE RD, OCALA, FL, 34482, Ocala, FL 34482
$465,000

2 beds

|

2 baths

|

2,316 sq ft

|

House

4687 NW 35TH LANE RD, OCALA, FL, 34482
Community: Ocala Preserve
The Country Club of Mount Dora 9049 SAINT ANDREWS WAY, MOUNT DORA, FL, ..., Mount Dora, FL 32757
$368,000

2 beds

|

2 baths

|

1,678 sq ft

|

House

9049 SAINT ANDREWS WAY, MOUNT DORA, FL, ...
Sun City Center 2216 W DEL WEBB BLVD, SUN CITY CENTER, F..., Sun City Center, FL 33573
$350,000

2 beds

|

2 baths

|

2,036 sq ft

|

House

2216 W DEL WEBB BLVD, SUN CITY CENTER, F...
Community: Sun City Center
Valencia Lakes 4949 MARBLE SPRINGS CIR, WIMAUMA, FL, 33..., Wimauma, FL 33598
$370,000

2 beds

|

2 baths

|

1,747 sq ft

|

Villa

4949 MARBLE SPRINGS CIR, WIMAUMA, FL, 33...
Community: Valencia Lakes
Highland Lakes 5500 LAVER ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$289,000

3 beds

|

2 baths

|

1,591 sq ft

|

House

5500 LAVER ST, LEESBURG, FL, 34748
Community: Highland Lakes

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3,958 homes near Winter Garden
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