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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.
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) VillageWalk at Lake Nona
$400Ks - $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
$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
Lake Ashton 4076 TRALEE DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$304,900

2 beds

|

2 baths

|

1,445 sq ft

|

House

4076 TRALEE DR, LAKE WALES, FL, 33859
Community: Lake Ashton
Highlands Ridge 3556 E GLEN EAGLES DR, AVON PARK, FL, 33..., Avon Park, FL 33825
$499,000

2 beds

|

2 baths

|

2,505 sq ft

|

House

3556 E GLEN EAGLES DR, AVON PARK, FL, 33...
Community: Highlands Ridge
Royal Highlands 21749 KING JOHN ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$315,000

3 beds

|

2 baths

|

1,704 sq ft

|

House

21749 KING JOHN ST, LEESBURG, FL, 34748
Community: Royal Highlands
Spruce Creek Country Club 13729 SE 89TH AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$256,500

3 beds

|

2 baths

|

1,760 sq ft

|

House

13729 SE 89TH AVE, SUMMERFIELD, FL, 3449...
Spruce Creek Country Club 13544 SE 89TH TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491
$449,500

3 beds

|

2 baths

|

2,278 sq ft

|

House

13544 SE 89TH TERRACE RD, SUMMERFIELD, F...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Stonecrest 12163 SE 176TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491
$539,000

3 beds

|

2 baths

|

2,668 sq ft

|

House

12163 SE 176TH LOOP, SUMMERFIELD, FL, 34...
Community: Stonecrest
Spruce Creek South 17744 SE 95TH CT, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$309,900

3 beds

|

2 baths

|

1,450 sq ft

|

House

17744 SE 95TH CT, SUMMERFIELD, FL, 34491
Community: Spruce Creek South
The Country Club of Mount Dora 7023 ARCADIAN CT, MOUNT DORA, FL, 32757, Mount Dora, FL 32757
$485,000

3 beds

|

2 baths

|

1,745 sq ft

|

House

7023 ARCADIAN CT, MOUNT DORA, FL, 32757
Latitude Margaritaville 306 HANG LOOSE WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$629,900

3 beds

|

3 baths

|

2,110 sq ft

|

House

306 HANG LOOSE WAY, DAYTONA BEACH, FL, 3...
Del Webb Sunbridge 6439 TRAILBLAZE BND, SAINT CLOUD, FL, 34..., Saint Cloud, FL 34771
$915,000

5 beds

|

5 baths

|

3,517 sq ft

|

House

6439 TRAILBLAZE BND, SAINT CLOUD, FL, 34...
Community: Del Webb Sunbridge
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 Ashton 4068 STONE CREEK LOOP, LAKE WALES, FL, 3..., Lake Wales, FL 33859
$550,000

3 beds

|

2 baths

|

2,064 sq ft

|

House

4068 STONE CREEK LOOP, LAKE WALES, FL, 3...
Community: Lake Ashton
Lake Ashton 5269 PEBBLE BEACH BLVD, WINTER HAVEN, FL..., Winter Haven, FL 33884
$292,500

2 beds

|

2 baths

|

1,495 sq ft

|

House

5269 PEBBLE BEACH BLVD, WINTER HAVEN, FL...
Community: Lake Ashton
Carillon Lakes 3379 FIDDLE LEAF WAY, LAKELAND, FL, 3381..., Lakeland, FL 33811
$337,775

3 beds

|

2 baths

|

1,624 sq ft

|

House

3379 FIDDLE LEAF WAY, LAKELAND, FL, 3381...
Community: Carillon Lakes
Lake Ashton 4101 LIMERICK DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$429,000

2 beds

|

2 baths

|

1,882 sq ft

|

House

4101 LIMERICK DR, LAKE WALES, FL, 33859
Community: Lake Ashton
Valencia Lakes 4946 SAPPHIRE SOUND DR, WIMAUMA, FL, 335..., Wimauma, FL 33598
$479,000

3 beds

|

2 baths

|

2,194 sq ft

|

House

4946 SAPPHIRE SOUND DR, WIMAUMA, FL, 335...
Community: Valencia Lakes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Lake James 2356 LAKE JAMES WAY, LAKELAND, FL, 33810, Lakeland, FL 33810
$409,000

2 beds

|

2 baths

|

2,124 sq ft

|

House

2356 LAKE JAMES WAY, LAKELAND, FL, 33810
Community: Lake James
Venetian Bay 3548 TUSCANY RESERVE BLVD, NEW SMYRNA BE..., New Smyrna Beach, FL 32168
$1,149,000

5 beds

|

4 baths

|

4,886 sq ft

|

House

3548 TUSCANY RESERVE BLVD, NEW SMYRNA BE...
Community: Venetian Bay
Stone Creek 6119 SW 93RD CIR, OCALA, FL, 34481, Ocala, FL 34481
$297,000

2 beds

|

2 baths

|

1,656 sq ft

|

House

6119 SW 93RD CIR, OCALA, FL, 34481
Community: Stone Creek
Southshore Bay 17322 HOLLY WELL AVE, WIMAUMA, FL, 33598, Wimauma, FL 33598
$275,000

2 beds

|

2 baths

|

1,406 sq ft

|

Villa

17322 HOLLY WELL AVE, WIMAUMA, FL, 33598
Community: Southshore Bay
Pine Run Estates 9940 SW 103RD PL, OCALA, FL, 34481, Ocala, FL 34481
$179,900

2 beds

|

2 baths

|

1,144 sq ft

|

House

9940 SW 103RD PL, OCALA, FL, 34481
Community: Pine Run Estates
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.
Ocala Preserve 5616 NW 39TH LN, OCALA, FL, 34482, Ocala, FL 34482
$304,900

2 beds

|

2 baths

|

1,454 sq ft

|

House

5616 NW 39TH LN, OCALA, FL, 34482
Community: Ocala Preserve
Kings Ridge 2126 BURLEY AVE, CLERMONT, FL, 34711, Clermont, FL 34711
$339,000

2 beds

|

2 baths

|

1,460 sq ft

|

House

2126 BURLEY AVE, CLERMONT, FL, 34711
Community: Kings Ridge
Stone Creek 9793 SW 63RD LOOP, OCALA, FL, 34481, Ocala, FL 34481
$487,500

4 beds

|

2 baths

|

2,186 sq ft

|

House

9793 SW 63RD LOOP, OCALA, FL, 34481
Community: Stone Creek
Summer Trees 102 UNDERBRUSH TRL, PORT ORANGE, FL, 321..., Port Orange, FL 32128
$299,999

2 beds

|

2 baths

|

1,370 sq ft

|

House

102 UNDERBRUSH TRL, PORT ORANGE, FL, 321...
Community: Summer Trees
Highlands Ridge 3501 E SAINT ANDREWS DR, AVON PARK, FL, ..., Avon Park, FL 33825
$299,900

3 beds

|

2 baths

|

1,999 sq ft

|

House

3501 E SAINT ANDREWS DR, AVON PARK, FL, ...
Community: Highlands Ridge
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Spruce Creek Country Club 8602 SE 133RD LN, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$270,000

2 beds

|

2 baths

|

1,490 sq ft

|

House

8602 SE 133RD LN, SUMMERFIELD, FL, 34491
Cypress Lakes 2101 CYPRESS CROSS DR, LAKELAND, FL, 338..., Lakeland, FL 33810
$250,000

2 beds

|

2 baths

|

1,320 sq ft

|

Manufactured Home

2101 CYPRESS CROSS DR, LAKELAND, FL, 338...
Community: Cypress Lakes
Tohoqua Reserve 1931 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744
$487,460

2 beds

|

2 baths

|

1,670 sq ft

|

House

1931 SPRING SHOWER CIR, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
SummerGlen 15782 SW 16TH AVENUE RD, OCALA, FL, 3447..., Ocala, FL 34473
$258,500

3 beds

|

2 baths

|

1,676 sq ft

|

House

15782 SW 16TH AVENUE RD, OCALA, FL, 3447...
Community: SummerGlen
Spruce Creek North 10980 SW 63RD AVE, OCALA, FL, 34476, Ocala, FL 34476
$249,500

3 beds

|

3 baths

|

1,966 sq ft

|

House

10980 SW 63RD AVE, OCALA, FL, 34476
Community: Spruce Creek North
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.
Sandpiper Golf & Country Club 6059 CONDOR DR, LAKELAND, FL, 33809, Lakeland, FL 33809
$395,000

3 beds

|

2 baths

|

2,195 sq ft

|

House

6059 CONDOR DR, LAKELAND, FL, 33809
On Top of the World 8798 SW 79TH CT, OCALA, FL, 34476, Ocala, FL 34476
$321,000

3 beds

|

2 baths

|

1,469 sq ft

|

House

8798 SW 79TH CT, OCALA, FL, 34476
Community: On Top of the World
The Lakes at Harmony 3443 SAGEBRUSH ST, HARMONY, FL, 34773, Harmony, FL 34773
$309,900

2 beds

|

2 baths

|

1,637 sq ft

|

House

3443 SAGEBRUSH ST, HARMONY, FL, 34773
Sun City Center 2509 LOCKSLEY ST # 237, SUN CITY CENTER,..., Sun City Center, FL 33573
$300,000

2 beds

|

2 baths

|

1,878 sq ft

|

Condo

2509 LOCKSLEY ST # 237, SUN CITY CENTER,...
Community: Sun City Center
Tampa Bay Golf and Country Club 9608 ROLLING CIR, SAN ANTONIO, FL, 33576, San Antonio, FL 33576
$328,000

3 beds

|

2 baths

|

1,390 sq ft

|

House

9608 ROLLING CIR, SAN ANTONIO, FL, 33576
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Huntington at Hunter's Ridge 81 HUNTINGTON PL, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174
$379,000

4 beds

|

2 baths

|

2,033 sq ft

|

House

81 HUNTINGTON PL, ORMOND BEACH, FL, 3217...
The Villages® 1971 CERNY CT, THE VILLAGES, FL, 32163, The Villages, FL 32163
$345,000

2 beds

|

2 baths

|

1,290 sq ft

|

House

1971 CERNY CT, THE VILLAGES, FL, 32163
Community: The Villages®
Pelican Bay Daytona Beach 115 MORNING DOVE CT, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119
$367,999

3 beds

|

2 baths

|

2,075 sq ft

|

House

115 MORNING DOVE CT, DAYTONA BEACH, FL, ...
Sun City Center 1112 MCDANIEL ST # 78, SUN CITY CENTER, ..., Sun City Center, FL 33573
$285,000

2 beds

|

2 baths

|

1,757 sq ft

|

Halfplex

1112 MCDANIEL ST # 78, SUN CITY CENTER, ...
Community: Sun City Center
Venetian Bay 3088 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$334,998

2 beds

|

2 baths

|

1,416 sq ft

|

House

3088 MELETO BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay

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3,958 homes near Winter Garden
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