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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
Oak Run 6541 SW 111TH LOOP, OCALA, FL, 34476, Ocala, FL 34476
$309,900

3 beds

|

2 baths

|

1,808 sq ft

|

House

6541 SW 111TH LOOP, OCALA, FL, 34476
Community: Oak Run
Spruce Creek Country Club 13944 SE 96TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$438,900

3 beds

|

2 baths

|

2,120 sq ft

|

House

13944 SE 96TH CIR, SUMMERFIELD, FL, 3449...
Del Webb Sunbridge 2698 RIVER CREEK LN, SAINT CLOUD, FL, 34..., Saint Cloud, FL 34771
$625,000

3 beds

|

3 baths

|

2,080 sq ft

|

House

2698 RIVER CREEK LN, SAINT CLOUD, FL, 34...
Community: Del Webb Sunbridge
Venetian Bay 424 LUNA BELLA LN APT 330, NEW SMYRNA BE..., New Smyrna Beach, FL 32168
$365,000

3 beds

|

3 baths

|

1,953 sq ft

|

Condo

424 LUNA BELLA LN APT 330, NEW SMYRNA BE...
Community: Venetian Bay
Spruce Creek Country Club 12855 SE 92ND COURT RD, SUMMERFIELD, FL,..., Summerfield, FL 34491
$363,900

2 beds

|

2 baths

|

1,995 sq ft

|

House

12855 SE 92ND COURT RD, SUMMERFIELD, FL,...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Lake Jovita Golf and Country Club 13539 CARRYBACK DR, DADE CITY, FL, 33525, Dade City, FL 33525
$950,000

4 beds

|

4 baths

|

3,217 sq ft

|

House

13539 CARRYBACK DR, DADE CITY, FL, 33525
Spruce Creek Country Club 12592 SE 97TH TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491
$475,000

3 beds

|

2 baths

|

2,413 sq ft

|

House

12592 SE 97TH TERRACE RD, SUMMERFIELD, F...
Spruce Creek Country Club 9450 SE 130TH PLACE RD, SUMMERFIELD, FL,..., Summerfield, FL 34491
$415,000

3 beds

|

3 baths

|

2,252 sq ft

|

House

9450 SE 130TH PLACE RD, SUMMERFIELD, FL,...
Heritage Hills 3201 SONESTA CT B, CLERMONT, FL, 34711, Clermont, FL 34711
$274,500

2 beds

|

2 baths

|

1,374 sq ft

|

Villa

3201 SONESTA CT B, CLERMONT, FL, 34711
Community: Heritage Hills
The Villages® 766 ARTESIA AVE, THE VILLAGES, FL, 32162, The Villages, FL 32162
$335,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

766 ARTESIA AVE, THE VILLAGES, FL, 32162
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® 6223 ATKINSON LN, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$315,000

2 beds

|

2 baths

|

1,203 sq ft

|

House

6223 ATKINSON LN, THE VILLAGES, FL, 3216...
Community: The Villages®
Spruce Creek South 10683 SE 174TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491
$249,900

3 beds

|

2 baths

|

1,620 sq ft

|

House

10683 SE 174TH LOOP, SUMMERFIELD, FL, 34...
Community: Spruce Creek South
Heritage Hills 3512 BELLAND CIR B, CLERMONT, FL, 34711, Clermont, FL 34711
$299,900

2 beds

|

2 baths

|

1,374 sq ft

|

Villa

3512 BELLAND CIR B, CLERMONT, FL, 34711
Community: Heritage Hills
Four Seasons at Orlando 7632 SAND PIERRE CT, KISSIMMEE, FL, 3474..., Kissimmee, FL 34747
$349,000

2 beds

|

2 baths

|

1,437 sq ft

|

Villa

7632 SAND PIERRE CT, KISSIMMEE, FL, 3474...
Tohoqua Reserve 1901 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744
$380,000

2 beds

|

2 baths

|

1,559 sq ft

|

House

1901 SPRING SHOWER CIR, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Del Webb Orlando 613 CANTABRIA DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$419,900

2 beds

|

2 baths

|

1,831 sq ft

|

House

613 CANTABRIA DR, DAVENPORT, FL, 33837
Community: Del Webb Orlando
The Villages® 1947 TRANQUILITY LN, THE VILLAGES, FL, 3..., The Villages, FL 32162
$485,000

3 beds

|

2 baths

|

1,654 sq ft

|

Villa

1947 TRANQUILITY LN, THE VILLAGES, FL, 3...
Community: The Villages®
Venetian Bay 3057 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$309,900

3 beds

|

3 baths

|

1,614 sq ft

|

Townhouse

3057 MELETO BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Marco Polo Village 10876 SW 53RD CIR, OCALA, FL, 34476, Ocala, FL 34476
$295,000

3 beds

|

2 baths

|

1,755 sq ft

|

House

10876 SW 53RD CIR, OCALA, FL, 34476
Community: Marco Polo Village
Lake Jovita Golf and Country Club 13444 TRAILING MOSS DR, DADE CITY, FL, 3..., Dade City, FL 33525
$875,000

3 beds

|

3 baths

|

2,685 sq ft

|

House

13444 TRAILING MOSS DR, DADE CITY, FL, 3...
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® 16615 SE 85TH LANGHAM CT, THE VILLAGES, ..., The Villages, FL 32162
$330,000

2 beds

|

2 baths

|

1,204 sq ft

|

Villa

16615 SE 85TH LANGHAM CT, THE VILLAGES, ...
Community: The Villages®
Venetian Bay 3604 ROMEA CIR, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$385,000

3 beds

|

2 baths

|

1,870 sq ft

|

Townhouse

3604 ROMEA CIR, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
The Villages® 1405 ESPINOZA LN, THE VILLAGES, FL, 3215..., The Villages, FL 32159
$220,000

1 beds

|

1 baths

|

804 sq ft

|

Villa

1405 ESPINOZA LN, THE VILLAGES, FL, 3215...
Community: The Villages®
The Villages® 6126 MULLIGAN RUN, THE VILLAGES, FL, 321..., The Villages, FL 32163
$900,000

3 beds

|

2 baths

|

2,930 sq ft

|

House

6126 MULLIGAN RUN, THE VILLAGES, FL, 321...
Community: The Villages®
Solivita 500 GRAND CANAL DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$284,000

2 beds

|

2 baths

|

1,512 sq ft

|

House

500 GRAND CANAL DR, POINCIANA, FL, 34759
Community: Solivita
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Lake Jovita Golf and Country Club 12615 EASTPOINTE DR, DADE CITY, FL, 3352..., Dade City, FL 33525
$437,500

3 beds

|

2 baths

|

1,722 sq ft

|

House

12615 EASTPOINTE DR, DADE CITY, FL, 3352...
Sun City Center 1015 RADISON LAKE CT # 65, SUN CITY CENT..., Sun City Center, FL 33573
$199,900

2 beds

|

2 baths

|

1,298 sq ft

|

Condo

1015 RADISON LAKE CT # 65, SUN CITY CENT...
Community: Sun City Center
On Top of the World 8895 SW 86TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$525,000

3 beds

|

3 baths

|

3,371 sq ft

|

House

8895 SW 86TH LOOP, OCALA, FL, 34481
Community: On Top of the World
Traditions at Lake Ruby 3667 PLYMOUTH DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$369,000

3 beds

|

3 baths

|

2,562 sq ft

|

House

3667 PLYMOUTH DR, WINTER HAVEN, FL, 3388...
The Villages® 4686 HILES PL, THE VILLAGES, FL, 32163, The Villages, FL 32163
$511,000

3 beds

|

2 baths

|

1,633 sq ft

|

Villa

4686 HILES PL, THE VILLAGES, FL, 32163
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® 527 BEVILLE PL, THE VILLAGES, FL, 32163, The Villages, FL 32163
$599,999

3 beds

|

2 baths

|

2,050 sq ft

|

House

527 BEVILLE PL, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 2725 HALSEY TER, THE VILLAGES, FL, 32162, The Villages, FL 32162
$649,900

3 beds

|

2 baths

|

1,927 sq ft

|

House

2725 HALSEY TER, THE VILLAGES, FL, 32162
Community: The Villages®
Palm Cay 7579 SW 108TH PL, OCALA, FL, 34476, Ocala, FL 34476
$229,000

2 beds

|

2 baths

|

912 sq ft

|

House

7579 SW 108TH PL, OCALA, FL, 34476
Community: Palm Cay
The Villages® 5868 WOOD STORK WAY, THE VILLAGES, FL, 3..., The Villages, FL 32163
$629,000

3 beds

|

2 baths

|

2,016 sq ft

|

House

5868 WOOD STORK WAY, THE VILLAGES, FL, 3...
Community: The Villages®
Spruce Creek South 9755 SE 176TH ST, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$239,900

2 beds

|

2 baths

|

1,548 sq ft

|

House

9755 SE 176TH ST, SUMMERFIELD, FL, 34491
Community: Spruce Creek South
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Sullivan Ranch 30101 BRETTON LOOP, MOUNT DORA, FL, 3275..., Mount Dora, FL 32757
$699,999

4 beds

|

3 baths

|

3,452 sq ft

|

House

30101 BRETTON LOOP, MOUNT DORA, FL, 3275...
Community: Sullivan Ranch
Huntington at Hunter's Ridge 13 FAWN HAVEN TRL, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$429,900

4 beds

|

3 baths

|

2,156 sq ft

|

House

13 FAWN HAVEN TRL, ORMOND BEACH, FL, 321...
The Villages® 3017 MOULTRIE WAY, THE VILLAGES, FL, 321..., The Villages, FL 32162
$319,900

2 beds

|

2 baths

|

1,278 sq ft

|

Villa

3017 MOULTRIE WAY, THE VILLAGES, FL, 321...
Community: The Villages®
Plantation at Leesburg 25233 LOST OAK CIR, LEESBURG, FL, 34748, Leesburg, FL 34748
$325,000

3 beds

|

2 baths

|

1,751 sq ft

|

House

25233 LOST OAK CIR, LEESBURG, FL, 34748
Solivita 3704 VIA MONTE NAPOLEONE DR, POINCIANA, ..., Poinciana, FL 34759
$599,900

4 beds

|

3 baths

|

2,430 sq ft

|

House

3704 VIA MONTE NAPOLEONE DR, POINCIANA, ...
Community: Solivita

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3,648 homes near Winter Garden
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