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

106 communities 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
$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 - $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
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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
$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
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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 - $500Ks
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
$300Ks - $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) VillageWalk at Lake Nona
$400Ks - $900Ks
VillageWalk at Lake Nona, Orlando, FL
Resale Only | Age-targeted | Built 2006 - 2016 | 1,300 homes
5 rating (1 reviews) Del Webb Sunbridge
$300Ks - $900Ks
Del Webb Sunbridge, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 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 | 1,029 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
$300Ks - $900Ks
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 homes
4 rating (4 reviews) Lakes of Mount Dora
$400Ks - $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 - $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
4.3 rating (15 reviews) Del Webb Orlando
$200Ks - $400Ks
Del Webb Orlando, Davenport, FL
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes
No reviews yet Pine Run Estates
<$100k - $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 - $800Ks
Esplanade at Wiregrass Ra..., Wesley Chapel, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 868 homes
The Villages® 2003 CORDERO CT, THE VILLAGES, FL, 32159, The Villages, FL 32159
$305,000

2 beds

|

2 baths

|

1,150 sq ft

|

House

2003 CORDERO CT, THE VILLAGES, FL, 32159
Community: The Villages®
Silver Lakes 2244 SILVER LAKES DR, LAKELAND, FL, 3381..., Lakeland, FL 33810
$254,990

2 beds

|

2 baths

|

1,545 sq ft

|

House

2244 SILVER LAKES DR, LAKELAND, FL, 3381...
Community: Silver Lakes
Summer Trees 11 LAKEPOINT CIR, PORT ORANGE, FL, 32128, Port Orange, FL 32128
$269,929

2 beds

|

2 baths

|

1,415 sq ft

|

House

11 LAKEPOINT CIR, PORT ORANGE, FL, 32128
Community: Summer Trees
Mirada 31637 CANNON RUSH DR, SAN ANTONIO, FL, 3..., San Antonio, FL 33576
$415,000

2 beds

|

2 baths

|

1,968 sq ft

|

House

31637 CANNON RUSH DR, SAN ANTONIO, FL, 3...
Community: Mirada
The Villages® 2954 HEINY PL, THE VILLAGES, FL, 32163, The Villages, FL 32163
$735,000

4 beds

|

2 baths

|

2,828 sq ft

|

House

2954 HEINY 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
Cherrywood 6082 SW 104TH ST, OCALA, FL, 34476, Ocala, FL 34476
$218,000

3 beds

|

2 baths

|

1,364 sq ft

|

House

6082 SW 104TH ST, OCALA, FL, 34476
Community: Cherrywood
New Lakes of Mount Dora 8301 BRIDGEPORT BAY CIR, MOUNT DORA, FL,..., Mount Dora, FL 32757
$499,500

3 beds

|

2 baths

|

1,823 sq ft

|

House

8301 BRIDGEPORT BAY CIR, MOUNT DORA, FL,...
Community: Lakes of Mount Dora
Arlington Ridge 27121 WHITE PLAINS WAY, LEESBURG, FL, 34..., Leesburg, FL 34748
$275,000

2 beds

|

2 baths

|

1,418 sq ft

|

Villa

27121 WHITE PLAINS WAY, LEESBURG, FL, 34...
Community: Arlington Ridge
The Villages® 9321 SE 172ND AUGUSTA LN, THE VILLAGES, ..., The Villages, FL 32162
$205,000

1 beds

|

1 baths

|

833 sq ft

|

Villa

9321 SE 172ND AUGUSTA LN, THE VILLAGES, ...
Community: The Villages®
Harbor Hills Country Club 39539 HARBOR HILLS BLVD, LADY LAKE, FL, ..., Lady Lake, FL 32159
$475,000

3 beds

|

3 baths

|

2,303 sq ft

|

House

39539 HARBOR HILLS BLVD, LADY LAKE, FL, ...
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.
Southshore Bay 17415 HOLLY WELL AVE, WIMAUMA, FL, 33598, Wimauma, FL 33598
$549,000

3 beds

|

3 baths

|

2,651 sq ft

|

House

17415 HOLLY WELL AVE, WIMAUMA, FL, 33598
Community: Southshore Bay
On Top of the World 8420 SW 93RD LN E, OCALA, FL, 34481, Ocala, FL 34481
$169,500

2 beds

|

2 baths

|

1,223 sq ft

|

Villa

8420 SW 93RD LN E, OCALA, FL, 34481
Community: On Top of the World
Venetian Bay 2840 ISLES WAY, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$549,000

3 beds

|

3 baths

|

2,131 sq ft

|

Townhouse

2840 ISLES WAY, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
Stone Creek 7234 SW 91ST CT, OCALA, FL, 34481, Ocala, FL 34481
$272,000

2 beds

|

2 baths

|

1,789 sq ft

|

House

7234 SW 91ST CT, OCALA, FL, 34481
Community: Stone Creek
New Latitude Margaritaville 422 GOOD LIFE WAY, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32124
$600,000

3 beds

|

2 baths

|

1,922 sq ft

|

House

422 GOOD LIFE WAY, DAYTONA BEACH, FL, 32...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 6126 MULLIGAN RUN, THE VILLAGES, FL, 321..., The Villages, FL 32163
$1,065,000

3 beds

|

2 baths

|

2,930 sq ft

|

House

6126 MULLIGAN RUN, THE VILLAGES, FL, 321...
Community: The Villages®
New Latitude Margaritaville 306 CORAL REEF WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$489,569

2 beds

|

2 baths

|

1,509 sq ft

|

Townhouse

306 CORAL REEF WAY, DAYTONA BEACH, FL, 3...
New The Villages® 767 BARRON PL, THE VILLAGES, FL, 32163, The Villages, FL 32163
$379,900

3 beds

|

2 baths

|

1,611 sq ft

|

House

767 BARRON PL, THE VILLAGES, FL, 32163
Community: The Villages®
New Del Webb Minneola 1336 ORANGE VALLEY RD, MINNEOLA, FL, 347..., Minneola, FL 34715
$448,000

2 beds

|

2 baths

|

1,405 sq ft

|

House

1336 ORANGE VALLEY RD, MINNEOLA, FL, 347...
Community: Del Webb Minneola
New Kings Ridge 4213 CHAMBERLAIN WAY, CLERMONT, FL, 3471..., Clermont, FL 34711
$299,000

2 beds

|

2 baths

|

1,200 sq ft

|

House

4213 CHAMBERLAIN WAY, CLERMONT, FL, 3471...
Community: Kings Ridge
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® 3817 MIRAGALIA LN, THE VILLAGES, FL, 321..., The Villages, FL 32163
$282,000

2 beds

|

2 baths

|

1,234 sq ft

|

House

3817 MIRAGALIA LN, THE VILLAGES, FL, 321...
Community: The Villages®
Breakaway Trails 22 FOREST VIEW WAY, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174
$519,000

4 beds

|

3 baths

|

2,456 sq ft

|

House

22 FOREST VIEW WAY, ORMOND BEACH, FL, 32...
Community: Breakaway Trails
Spruce Creek Preserve 11395 SW 139TH ST, DUNNELLON, FL, 34432, Dunnellon, FL 34432
$273,539

3 beds

|

2 baths

|

1,724 sq ft

|

House

11395 SW 139TH ST, DUNNELLON, FL, 34432
The Villages® 1146 W BOONE CT, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$235,000

2 beds

|

2 baths

|

1,418 sq ft

|

Manufactured Home

1146 W BOONE CT, LADY LAKE, FL, 32159
Community: The Villages®
The Villages® 664 MISSION HILLS TRL, THE VILLAGES, FL,..., The Villages, FL 32162
$530,000

3 beds

|

2 baths

|

1,587 sq ft

|

Villa

664 MISSION HILLS TRL, THE VILLAGES, FL,...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 3396 GREENACRES TER, THE VILLAGES, FL, 3..., The Villages, FL 32163
$346,500

3 beds

|

2 baths

|

1,351 sq ft

|

House

3396 GREENACRES TER, THE VILLAGES, FL, 3...
Community: The Villages®
The Villages® 516 JUNCTION PL, THE VILLAGES, FL, 32163, The Villages, FL 32163
$330,000

2 beds

|

2 baths

|

1,262 sq ft

|

House

516 JUNCTION PL, THE VILLAGES, FL, 32163
Community: The Villages®
Cherrywood 10350 SW 62ND TERRACE RD, OCALA, FL, 344..., Ocala, FL 34476
$210,000

2 beds

|

2 baths

|

1,667 sq ft

|

House

10350 SW 62ND TERRACE RD, OCALA, FL, 344...
Community: Cherrywood
Summit Greens 807 WOLF CREEK ST, CLERMONT, FL, 34711, Clermont, FL 34711
$339,000

2 beds

|

2 baths

|

1,717 sq ft

|

House

807 WOLF CREEK ST, CLERMONT, FL, 34711
Community: Summit Greens
Scottish Highlands 1011 DUNDEE CIR, LEESBURG, FL, 34788, Leesburg, FL 34788
$255,000

3 beds

|

2 baths

|

1,938 sq ft

|

House

1011 DUNDEE CIR, LEESBURG, FL, 34788
Community: Scottish 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.
Plantation at Leesburg 24802 PINE HL, LEESBURG, FL, 34748, Leesburg, FL 34748
$155,000

2 beds

|

2 baths

|

936 sq ft

|

Manufactured Home

24802 PINE HL, LEESBURG, FL, 34748
New The Villages® 9223 SE 179TH WESLEY ST, THE VILLAGES, F..., The Villages, FL 32162
$319,000

2 beds

|

2 baths

|

1,160 sq ft

|

House

9223 SE 179TH WESLEY ST, THE VILLAGES, F...
Community: The Villages®
Stonecrest 17525 SE 121ST CIR, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$400,000

3 beds

|

2 baths

|

2,000 sq ft

|

House

17525 SE 121ST CIR, SUMMERFIELD, FL, 344...
Community: Stonecrest
New Highland Fairways 2012 LONG BOAT DR, LAKELAND, FL, 33810, Lakeland, FL 33810
$280,000

3 beds

|

2 baths

|

1,661 sq ft

|

House

2012 LONG BOAT DR, LAKELAND, FL, 33810
Community: Highland Fairways
On Top of the World 8166 SW 80TH TER, OCALA, FL, 34476, Ocala, FL 34476
$265,000

3 beds

|

2 baths

|

1,487 sq ft

|

House

8166 SW 80TH TER, OCALA, FL, 34476
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
The Villages® 960 PICKERING PATH, THE VILLAGES, FL, 32..., The Villages, FL 32163
$804,900

3 beds

|

2 baths

|

2,575 sq ft

|

House

960 PICKERING PATH, THE VILLAGES, FL, 32...
Community: The Villages®
New Sun City Center 611 CHIPPER DR, SUN CITY CENTER, FL, 335..., Sun City Center, FL 33573
$349,900

2 beds

|

2 baths

|

1,668 sq ft

|

Townhouse

611 CHIPPER DR, SUN CITY CENTER, FL, 335...
Community: Sun City Center
Del Webb Oasis 13081 SUNRISE HARVEST DR, WINTER GARDEN,..., Winter Garden, FL 34787
$825,000

5 beds

|

4 baths

|

3,429 sq ft

|

House

13081 SUNRISE HARVEST DR, WINTER GARDEN,...
Community: Del Webb Oasis
Del Webb Oasis 13075 SUNRISE HARVEST DR, WINTER GARDEN,..., Winter Garden, FL 34787
$800,000

5 beds

|

4 baths

|

2,670 sq ft

|

House

13075 SUNRISE HARVEST DR, WINTER GARDEN,...
Community: Del Webb Oasis
Del Webb Sunbridge 6514 BARNSTORM WAY, SAINT CLOUD, FL, 347..., Saint Cloud, FL 34771
$539,900

3 beds

|

2 baths

|

1,881 sq ft

|

House

6514 BARNSTORM WAY, SAINT CLOUD, FL, 347...
Community: Del Webb Sunbridge

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106 communities near Winter Garden
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