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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
Want to learn more about 55+ communities in Winter Garden? 55places can help!
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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) VillageWalk at Lake Nona
$300Ks - $1Ms
VillageWalk at Lake Nona, Orlando, FL
Resale Only | Age-targeted | Built 2006 - 2016 | 1,300 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
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
$300Ks - $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
On Top of the World 9015 SW 94TH ST D, OCALA, FL, 34481, Ocala, FL 34481
$199,500

2 beds

|

2 baths

|

1,861 sq ft

|

Villa

9015 SW 94TH ST D, OCALA, FL, 34481
Community: On Top of the World
Esplanade at Highland Ranch 2342 CLEMBLUE RD, CLERMONT, FL, 34715, Clermont, FL 34715
$430,000

3 beds

|

3 baths

|

1,847 sq ft

|

House

2342 CLEMBLUE RD, CLERMONT, FL, 34715
The Villages® 3021 BEARD RD, THE VILLAGES, FL, 32163, The Villages, FL 32163
$329,000

2 beds

|

2 baths

|

1,203 sq ft

|

Villa

3021 BEARD RD, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 750 PASTURE ST, THE VILLAGES, FL, 32163, The Villages, FL 32163
$800,000

3 beds

|

2 baths

|

2,602 sq ft

|

House

750 PASTURE ST, THE VILLAGES, FL, 32163
Community: The Villages®
Lakes of Mount Dora 8348 BRIDGEPORT BAY CIR, MOUNT DORA, FL,..., Mount Dora, FL 32757
$795,000

4 beds

|

3 baths

|

3,156 sq ft

|

House

8348 BRIDGEPORT BAY CIR, MOUNT DORA, FL,...
Community: Lakes of Mount Dora
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 2608 BOTELLO AVE, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$239,995

2 beds

|

2 baths

|

1,231 sq ft

|

House

2608 BOTELLO AVE, THE VILLAGES, FL, 3216...
Community: The Villages®
The Villages® 1615 NAVIDAD ST, THE VILLAGES, FL, 32162, The Villages, FL 32162
$284,900

2 beds

|

2 baths

|

1,143 sq ft

|

Villa

1615 NAVIDAD ST, THE VILLAGES, FL, 32162
Community: The Villages®
Sun City Center 120 KNOLLPOINT DR, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$133,000

2 beds

|

2 baths

|

1,073 sq ft

|

Condo

120 KNOLLPOINT DR, SUN CITY CENTER, FL, ...
Community: Sun City Center
Venetian Bay 3454 VELONA AVE, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168
$450,000

3 beds

|

2 baths

|

2,211 sq ft

|

House

3454 VELONA AVE, NEW SMYRNA BEACH, FL, 3...
Community: Venetian Bay
Ocala Preserve 3651 NW 56TH AVE, OCALA, FL, 34482, Ocala, FL 34482
$275,000

2 beds

|

2 baths

|

1,666 sq ft

|

House

3651 NW 56TH AVE, OCALA, FL, 34482
Community: Ocala Preserve
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® 17086 SE 75TH WICKSON CT, THE VILLAGES, ..., The Villages, FL 32162
$289,000

2 beds

|

2 baths

|

1,150 sq ft

|

Villa

17086 SE 75TH WICKSON CT, THE VILLAGES, ...
Community: The Villages®
The Villages® 7574 SE 170TH LONGVIEW LN, THE VILLAGES,..., The Villages, FL 32162
$275,000

2 beds

|

2 baths

|

1,186 sq ft

|

House

7574 SE 170TH LONGVIEW LN, THE VILLAGES,...
Community: The Villages®
Del Webb Orlando 251 TOMELLOSO WAY, DAVENPORT, FL, 33837, Davenport, FL 33837
$309,000

2 beds

|

2 baths

|

1,495 sq ft

|

House

251 TOMELLOSO WAY, DAVENPORT, FL, 33837
Community: Del Webb Orlando
On Top of the World 9839 SW 99TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$269,900

2 beds

|

2 baths

|

1,469 sq ft

|

House

9839 SW 99TH LOOP, OCALA, FL, 34481
Community: On Top of the World
Lakeside Landings 10079 KETCH KAY LN, OXFORD, FL, 34484, Oxford, FL 34484
$350,000

3 beds

|

2 baths

|

1,916 sq ft

|

House

10079 KETCH KAY LN, OXFORD, FL, 34484
Community: Lakeside Landings
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Marco Polo Village 10964 SW 53RD CIR, OCALA, FL, 34476, Ocala, FL 34476
$299,900

3 beds

|

2 baths

|

2,230 sq ft

|

House

10964 SW 53RD CIR, OCALA, FL, 34476
Community: Marco Polo Village
Lake James 8288 LAKE JAMES DR, LAKELAND, FL, 33810, Lakeland, FL 33810
$429,900

2 beds

|

2 baths

|

2,439 sq ft

|

House

8288 LAKE JAMES DR, LAKELAND, FL, 33810
Community: Lake James
Valencia Lakes 15948 COBBLE MILL DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$339,000

3 beds

|

2 baths

|

1,593 sq ft

|

Condo

15948 COBBLE MILL DR, WIMAUMA, FL, 33598
Community: Valencia Lakes
Arlington Ridge 4415 ANTIETAM CREEK TRL, LEESBURG, FL, 3..., Leesburg, FL 34748
$420,000

2 beds

|

2 baths

|

2,076 sq ft

|

House

4415 ANTIETAM CREEK TRL, LEESBURG, FL, 3...
Community: Arlington Ridge
On Top of the World 9260 SW 92ND PLACE RD, OCALA, FL, 34481, Ocala, FL 34481
$199,990

3 beds

|

2 baths

|

2,246 sq ft

|

House

9260 SW 92ND PLACE RD, 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.
Tampa Bay Golf and Country Club 11027 DORMIE DR, SAN ANTONIO, FL, 33576, San Antonio, FL 33576
$299,000

2 beds

|

2 baths

|

1,700 sq ft

|

House

11027 DORMIE DR, SAN ANTONIO, FL, 33576
JB Ranch 6125 SW 88TH LOOP, OCALA, FL, 34476, Ocala, FL 34476
$324,900

2 beds

|

2 baths

|

1,813 sq ft

|

House

6125 SW 88TH LOOP, OCALA, FL, 34476
Community: JB Ranch
Sun City Center 1361 EMERALD DUNES DR, SUN CITY CENTER, ..., Sun City Center, FL 33573
$439,900

3 beds

|

2 baths

|

2,482 sq ft

|

Condo

1361 EMERALD DUNES DR, SUN CITY CENTER, ...
Community: Sun City Center
Royal Highlands 21721 LOCH HAVEN PASS, LEESBURG, FL, 347..., Leesburg, FL 34748
$282,500

3 beds

|

2 baths

|

2,016 sq ft

|

House

21721 LOCH HAVEN PASS, LEESBURG, FL, 347...
Community: Royal Highlands
Sun City Center 1805 COLUMBINE PL, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$299,900

2 beds

|

2 baths

|

1,756 sq ft

|

House

1805 COLUMBINE PL, SUN CITY CENTER, FL, ...
Community: Sun City Center
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Sun City Center 611 CHIPPER DR, SUN CITY CENTER, FL, 335..., Sun City Center, FL 33573
$334,900

2 beds

|

2 baths

|

1,668 sq ft

|

Townhouse

611 CHIPPER DR, SUN CITY CENTER, FL, 335...
Community: Sun City Center
Plantation at Leesburg 4514 RIVER RIDGE DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$289,900

3 beds

|

2 baths

|

1,785 sq ft

|

House

4514 RIVER RIDGE DR, LEESBURG, FL, 34748
The Villages® 2304 FRINGE TREE TRL, THE VILLAGES, FL, ..., The Villages, FL 32162
$579,500

3 beds

|

2 baths

|

1,939 sq ft

|

House

2304 FRINGE TREE TRL, THE VILLAGES, FL, ...
Community: The Villages®
The Villages® 2369 TRAVIS PL, THE VILLAGES, FL, 32162, The Villages, FL 32162
$264,900

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

2369 TRAVIS PL, THE VILLAGES, FL, 32162
Community: The Villages®
Pelican Bay Daytona Beach 240 BOB WHITE CT # 240, DAYTONA BEACH, F..., Daytona Beach, FL 32119
$219,000

2 beds

|

2 baths

|

1,093 sq ft

|

Condo

240 BOB WHITE CT # 240, DAYTONA BEACH, F...
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.
Venetian Bay 513 LUNA BELLA LN, NEW SMYRNA BEACH, FL,..., New Smyrna Beach, FL 32168
$774,999

4 beds

|

3 baths

|

2,900 sq ft

|

House

513 LUNA BELLA LN, NEW SMYRNA BEACH, FL,...
Community: Venetian Bay
Pelican Bay Daytona Beach 240 BOB WHITE CT 2400, DAYTONA BEACH, FL..., Daytona Beach, FL 32119
$219,000

2 beds

|

2 baths

|

1,093 sq ft

|

Condo

240 BOB WHITE CT 2400, DAYTONA BEACH, FL...
Spruce Creek Country Club 9033 SE 135TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$274,900

3 beds

|

2 baths

|

1,726 sq ft

|

House

9033 SE 135TH LOOP, SUMMERFIELD, FL, 344...
The Villages® 2041 ROYAL ELM RD, THE VILLAGES, FL, 321..., The Villages, FL 32162
$389,000

3 beds

|

2 baths

|

1,551 sq ft

|

House

2041 ROYAL ELM RD, THE VILLAGES, FL, 321...
Community: The Villages®
New Lake James 7898 LAKE JAMES BLVD, LAKELAND, FL, 3381..., Lakeland, FL 33810
$495,000

2 beds

|

2 baths

|

1,911 sq ft

|

House

7898 LAKE JAMES BLVD, LAKELAND, FL, 3381...
Community: Lake James
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Oak Run 7705 SW 114TH LOOP, OCALA, FL, 34476, Ocala, FL 34476
$249,900

2 beds

|

2 baths

|

1,583 sq ft

|

House

7705 SW 114TH LOOP, OCALA, FL, 34476
Community: Oak Run
Sun City Center 401 FELTHAM TRL A, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$129,900

2 beds

|

2 baths

|

984 sq ft

|

Condo

401 FELTHAM TRL A, SUN CITY CENTER, FL, ...
Community: Sun City Center
Solivita 154 INDIAN WELLS AVE, KISSIMMEE, FL, 347..., Kissimmee, FL 34759
$364,900

3 beds

|

3 baths

|

1,961 sq ft

|

House

154 INDIAN WELLS AVE, KISSIMMEE, FL, 347...
Community: Solivita
Tampa Bay Golf and Country Club 10026 GAP WEDGE DR, SAN ANTONIO, FL, 335..., San Antonio, FL 33576
$319,900

3 beds

|

2 baths

|

1,731 sq ft

|

House

10026 GAP WEDGE DR, SAN ANTONIO, FL, 335...
The Villages® 2572 BERRINGTON LOOP, THE VILLAGES, FL, ..., The Villages, FL 32162
$334,900

3 beds

|

2 baths

|

1,483 sq ft

|

House

2572 BERRINGTON LOOP, THE VILLAGES, FL, ...
Community: The Villages®

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3,648 homes near Winter Garden
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