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

3,703 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 - $500Ks
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
Lake Jovita Golf and Country Club 13302 TRAILING MOSS DR, DADE CITY, FL, 3..., Dade City, FL 33525
$860,000

4 beds

|

3 baths

|

2,632 sq ft

|

House

13302 TRAILING MOSS DR, DADE CITY, FL, 3...
The Villages® 1728 MORELOS RD, THE VILLAGES, FL, 32159, The Villages, FL 32159
$265,000

2 beds

|

2 baths

|

1,121 sq ft

|

Villa

1728 MORELOS RD, THE VILLAGES, FL, 32159
Community: The Villages®
Lake Ashton 4220 DORNOCH DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$369,900

3 beds

|

2 baths

|

1,845 sq ft

|

House

4220 DORNOCH DR, LAKE WALES, FL, 33859
Community: Lake Ashton
Harbor Hills Country Club 5096 GREENS DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$750,000

4 beds

|

3 baths

|

2,900 sq ft

|

House

5096 GREENS DR, LADY LAKE, FL, 32159
Lake Ashton 4488 TURNBERRY LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$225,000

2 beds

|

2 baths

|

1,083 sq ft

|

House

4488 TURNBERRY LN, LAKE WALES, FL, 33859
Community: Lake Ashton
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Sun City Center 2427 SIFIELD GREENS WAY, SUN CITY CENTER..., Sun City Center, FL 33573
$280,000

2 beds

|

2 baths

|

1,396 sq ft

|

Condo

2427 SIFIELD GREENS WAY, SUN CITY CENTER...
Community: Sun City Center
Highland Lakes 6419 BORG ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$270,000

3 beds

|

2 baths

|

1,964 sq ft

|

House

6419 BORG ST, LEESBURG, FL, 34748
Community: Highland Lakes
Southshore Bay 16938 SCUBA CREST ST, WIMAUMA, FL, 33598, Wimauma, FL 33598
$624,999

3 beds

|

4 baths

|

2,778 sq ft

|

House

16938 SCUBA CREST ST, WIMAUMA, FL, 33598
Community: Southshore Bay
Traditions at Lake Ruby 3987 BEDFORD AVE, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$370,000

2 beds

|

2 baths

|

1,817 sq ft

|

House

3987 BEDFORD AVE, WINTER HAVEN, FL, 3388...
Pelican Bay Daytona Beach 150 BLUE HERON DR B, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119
$239,700

3 beds

|

2 baths

|

1,365 sq ft

|

Condo

150 BLUE HERON DR B, DAYTONA BEACH, 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.
Solivita 541 MILANO RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$520,000

3 beds

|

2 baths

|

2,450 sq ft

|

House

541 MILANO RD, KISSIMMEE, FL, 34759
Community: Solivita
The Villages® 1142 W BOONE CT, THE VILLAGES, FL, 32159, The Villages, FL 32159
$279,000

2 beds

|

2 baths

|

1,120 sq ft

|

House

1142 W BOONE CT, THE VILLAGES, FL, 32159
Community: The Villages®
Alhambra Villas Condominiums 239 N HILL AVE # 110, DELAND, FL, 32724, Deland, FL 32724
$200,000

2 beds

|

2 baths

|

1,091 sq ft

|

Condo

239 N HILL AVE # 110, DELAND, FL, 32724
Sullivan Ranch 21224 NORIC CV, MOUNT DORA, FL, 32757, Mount Dora, FL 32757
$510,000

5 beds

|

3 baths

|

2,638 sq ft

|

House

21224 NORIC CV, MOUNT DORA, FL, 32757
Community: Sullivan Ranch
Latitude Margaritaville 308 LOW TIDE LN, DAYTONA BEACH, FL, 3212..., Daytona Beach, FL 32124
$554,900

2 beds

|

3 baths

|

1,743 sq ft

|

House

308 LOW TIDE LN, DAYTONA BEACH, FL, 3212...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
On Top of the World 8018 SW 83RD PL, OCALA, FL, 34476, Ocala, FL 34476
$234,900

3 beds

|

2 baths

|

1,576 sq ft

|

House

8018 SW 83RD PL, OCALA, FL, 34476
Community: On Top of the World
Latitude Margaritaville 329 ISLAND BREEZE AVE, DAYTONA BEACH, FL..., Daytona Beach, FL 32124
$475,000

2 beds

|

2 baths

|

1,862 sq ft

|

House

329 ISLAND BREEZE AVE, DAYTONA BEACH, FL...
On Top of the World 10525 SW 90TH STREET RD, OCALA, FL, 3448..., Ocala, FL 34481
$359,900

2 beds

|

2 baths

|

1,651 sq ft

|

House

10525 SW 90TH STREET RD, OCALA, FL, 3448...
Community: On Top of the World
Sullivan Ranch 30532 GIDRAN TER, MOUNT DORA, FL, 32757, Mount Dora, FL 32757
$499,000

4 beds

|

2 baths

|

2,426 sq ft

|

House

30532 GIDRAN TER, MOUNT DORA, FL, 32757
Community: Sullivan Ranch
Vienna Square 1561 VIENNA SQUARE DR, WINTER HAVEN, FL,..., Winter Haven, FL 33884
$227,000

2 beds

|

2 baths

|

1,231 sq ft

|

Villa

1561 VIENNA SQUARE DR, WINTER HAVEN, FL,...
Community: Vienna Square
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.
Ridgehaven 1348 OAKHAVEN AVE, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$426,269

4 beds

|

3 baths

|

2,190 sq ft

|

House

1348 OAKHAVEN AVE, ORMOND BEACH, FL, 321...
Community: Ridgehaven
SummerGlen 15596 SW 13TH CIR, OCALA, FL, 34473, Ocala, FL 34473
$324,900

3 beds

|

2 baths

|

1,806 sq ft

|

House

15596 SW 13TH CIR, OCALA, FL, 34473
Community: SummerGlen
The Villages® 892 NASH LOOP, THE VILLAGES, FL, 32162, The Villages, FL 32162
$289,900

2 beds

|

2 baths

|

1,090 sq ft

|

House

892 NASH LOOP, THE VILLAGES, FL, 32162
Community: The Villages®
Sun City Center 635 CHIPPER DR, SUN CITY CENTER, FL, 335..., Sun City Center, FL 33573
$315,000

2 beds

|

2 baths

|

1,493 sq ft

|

Villa

635 CHIPPER DR, SUN CITY CENTER, FL, 335...
Community: Sun City Center
On Top of the World 9093 SW 91ST CIR, OCALA, FL, 34481, Ocala, FL 34481
$249,900

2 beds

|

2 baths

|

1,629 sq ft

|

House

9093 SW 91ST CIR, OCALA, FL, 34481
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
JB Ranch 6197 SW 89TH STREET RD, OCALA, FL, 34476, Ocala, FL 34476
$330,000

2 beds

|

2 baths

|

1,813 sq ft

|

House

6197 SW 89TH STREET RD, OCALA, FL, 34476
Community: JB Ranch
Royal Harbor 5486 BOUNTY CIR, TAVARES, FL, 32778, Tavares, FL 32778
$409,000

3 beds

|

3 baths

|

2,284 sq ft

|

House

5486 BOUNTY CIR, TAVARES, FL, 32778
Community: Royal Harbor
Latitude Margaritaville 333 POP TOP LN, DAYTONA BEACH, FL, 32124, Daytona Beach, FL 32124
$424,999

2 beds

|

2 baths

|

1,308 sq ft

|

House

333 POP TOP LN, DAYTONA BEACH, FL, 32124
Sun City Center 205 STRONGBOW CT, SUN CITY CENTER, FL, 3..., Sun City Center, FL 33573
$255,900

2 beds

|

2 baths

|

1,756 sq ft

|

Halfplex

205 STRONGBOW CT, SUN CITY CENTER, FL, 3...
Community: Sun City Center
Valencia del Sol 4931 SEVILLA SHORES DR, WIMAUMA, FL, 335..., Wimauma, FL 33598
$460,000

3 beds

|

2 baths

|

1,890 sq ft

|

House

4931 SEVILLA SHORES DR, WIMAUMA, FL, 335...
Community: Valencia del Sol
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.
Highland Lakes 26030 NEWCOMBE CIR, LEESBURG, FL, 34748, Leesburg, FL 34748
$239,900

2 beds

|

2 baths

|

1,293 sq ft

|

Villa

26030 NEWCOMBE CIR, LEESBURG, FL, 34748
Community: Highland Lakes
Highland Lakes 26608 RACQUET CIR, LEESBURG, FL, 34748, Leesburg, FL 34748
$259,900

2 beds

|

2 baths

|

1,499 sq ft

|

House

26608 RACQUET CIR, LEESBURG, FL, 34748
Community: Highland Lakes
Thunderbird Hill 3716 SUNBIRD CIR, SEBRING, FL, 33872, Sebring, FL 33872
$205,000

2 beds

|

2 baths

|

1,080 sq ft

|

Villa

3716 SUNBIRD CIR, SEBRING, FL, 33872
Community: Thunderbird Hill
Solivita 308 VESTRELLA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$300,000

2 beds

|

2 baths

|

1,703 sq ft

|

House

308 VESTRELLA DR, KISSIMMEE, FL, 34759
Community: Solivita
Summer Trees 125 CROOKED PINE RD, PORT ORANGE, FL, 32..., Port Orange, FL 32128
$299,900

2 beds

|

2 baths

|

1,855 sq ft

|

House

125 CROOKED PINE RD, PORT ORANGE, FL, 32...
Community: Summer Trees
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Kings Ridge 2160 ADDISON AVE, CLERMONT, FL, 34711, Clermont, FL 34711
$299,990

2 beds

|

2 baths

|

1,334 sq ft

|

House

2160 ADDISON AVE, CLERMONT, FL, 34711
Community: Kings Ridge
Lake Ashton 4124 MUIRFIELD LOOP, LAKE WALES, FL, 338..., Lake Wales, FL 33859
$319,900

3 beds

|

2 baths

|

1,682 sq ft

|

House

4124 MUIRFIELD LOOP, LAKE WALES, FL, 338...
Community: Lake Ashton
Ridgehaven 449 BROOKHAVEN TRL, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174
$485,580

3 beds

|

3 baths

|

2,181 sq ft

|

House

449 BROOKHAVEN TRL, ORMOND BEACH, FL, 32...
Community: Ridgehaven
The Country Club of Mount Dora 8012 SAINT JAMES WAY, MOUNT DORA, FL, 32..., Mount Dora, FL 32757
$385,000

3 beds

|

2 baths

|

2,062 sq ft

|

House

8012 SAINT JAMES WAY, MOUNT DORA, FL, 32...
Solivita 159 CASAVISTA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$434,000

2 beds

|

2 baths

|

1,771 sq ft

|

House

159 CASAVISTA DR, KISSIMMEE, FL, 34759
Community: Solivita

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3,703 homes near Winter Garden
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