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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.
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) Trilogy® Orlando
$200Ks - $600Ks
Trilogy® Orlando, Groveland, FL
Resale Only | 55+ age-restricted | Built 2005 - 2022 | 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
$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
Palm Cay 8274 SW 106TH PL, OCALA, FL, 34481, Ocala, FL 34481
$164,900

2 beds

|

1 baths

|

876 sq ft

|

House

8274 SW 106TH PL, OCALA, FL, 34481
Community: Palm Cay
Sun City Center 2104 HEMBURY PL # 33, SUN CITY CENTER, F..., Sun City Center, FL 33573
$200,000

2 beds

|

2 baths

|

1,149 sq ft

|

Condo

2104 HEMBURY PL # 33, SUN CITY CENTER, F...
Community: Sun City Center
Sun City Center 1908 STERLING GLEN CT, SUN CITY CENTER, ..., Sun City Center, FL 33573
$350,000

2 beds

|

2 baths

|

1,497 sq ft

|

House

1908 STERLING GLEN CT, SUN CITY CENTER, ...
Community: Sun City Center
On Top of the World 8086 SW 81ST LOOP, OCALA, FL, 34476, Ocala, FL 34476
$249,900

3 beds

|

2 baths

|

1,576 sq ft

|

House

8086 SW 81ST LOOP, OCALA, FL, 34476
Community: On Top of the World
Solivita 804 SAN RAPHAEL ST, POINCIANA, FL, 34759, Poinciana, FL 34759
$522,500

3 beds

|

4 baths

|

2,782 sq ft

|

House

804 SAN RAPHAEL ST, POINCIANA, FL, 34759
Community: Solivita
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
High Vista at Ridgewood Lakes 236 RIDGE VIEW DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$270,720

2 beds

|

2 baths

|

1,457 sq ft

|

House

236 RIDGE VIEW DR, DAVENPORT, FL, 33837
The Villages® 1105 DEL TORO DR, THE VILLAGES, FL, 3215..., The Villages, FL 32159
$279,900

2 beds

|

2 baths

|

1,440 sq ft

|

Manufactured Home

1105 DEL TORO DR, THE VILLAGES, FL, 3215...
Community: The Villages®
Sun City Center 1216 LYNDHURST GREENS DR, SUN CITY CENTE..., Sun City Center, FL 33573
$249,900

2 beds

|

2 baths

|

1,188 sq ft

|

Condo

1216 LYNDHURST GREENS DR, SUN CITY CENTE...
Community: Sun City Center
Summer Trees 89 CROOKED PINE RD, PORT ORANGE, FL, 321..., Port Orange, FL 32128
$263,900

2 beds

|

2 baths

|

1,010 sq ft

|

House

89 CROOKED PINE RD, PORT ORANGE, FL, 321...
Community: Summer Trees
Sun City Center 1710 NEW BEDFORD DR, SUN CITY CENTER, FL..., Sun City Center, FL 33573
$474,900

2 beds

|

2 baths

|

2,078 sq ft

|

House

1710 NEW BEDFORD DR, SUN CITY CENTER, FL...
Community: Sun City Center
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 1062 UMBRIA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$355,000

2 beds

|

2 baths

|

1,655 sq ft

|

House

1062 UMBRIA DR, KISSIMMEE, FL, 34759
Community: Solivita
Stone Creek 6767 SW 91ST CIR, OCALA, FL, 34481, Ocala, FL 34481
$294,888

2 beds

|

2 baths

|

1,916 sq ft

|

Villa

6767 SW 91ST CIR, OCALA, FL, 34481
Community: Stone Creek
Valencia Lakes 15856 COBBLE MILL DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$367,000

3 beds

|

2 baths

|

1,897 sq ft

|

House

15856 COBBLE MILL DR, WIMAUMA, FL, 33598
Community: Valencia Lakes
On Top of the World 9121 SW 83RD CT C, OCALA, FL, 34481, Ocala, FL 34481
$154,000

2 beds

|

2 baths

|

1,249 sq ft

|

Villa

9121 SW 83RD CT C, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 9794 SW 96TH ST, OCALA, FL, 34481, Ocala, FL 34481
$184,900

2 beds

|

2 baths

|

1,201 sq ft

|

House

9794 SW 96TH ST, 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
On Top of the World 8830 SW 98TH PL L, OCALA, FL, 34481, Ocala, FL 34481
$182,000

2 beds

|

3 baths

|

1,764 sq ft

|

Townhouse

8830 SW 98TH PL L, OCALA, FL, 34481
Community: On Top of the World
Sun City Center 807 CHIPPER DR, SUN CITY CENTER, FL, 335..., Sun City Center, FL 33573
$339,900

2 beds

|

2 baths

|

1,854 sq ft

|

Townhouse

807 CHIPPER DR, SUN CITY CENTER, FL, 335...
Community: Sun City Center
Sun City Center 1120 RADISON AVE # 6, SUN CITY CENTER, F..., Sun City Center, FL 33573
$179,000

2 beds

|

2 baths

|

963 sq ft

|

Condo

1120 RADISON AVE # 6, SUN CITY CENTER, F...
Community: Sun City Center
Lake Ashton 4568 BACK NINE DR, WINTER HAVEN, FL, 338..., Winter Haven, FL 33884
$360,000

3 beds

|

2 baths

|

2,043 sq ft

|

House

4568 BACK NINE DR, WINTER HAVEN, FL, 338...
Community: Lake Ashton
Del Webb Sunbridge 2542 CLIFF WAY, SAINT CLOUD, FL, 34771, Saint Cloud, FL 34771
$397,000

2 beds

|

2 baths

|

1,579 sq ft

|

Villa

2542 CLIFF WAY, SAINT CLOUD, FL, 34771
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.
Gatherings of Lake Nona 7565 LAUREATE BLVD UNIT 3408, ORLANDO, F..., Orlando, FL 32827
$359,000

2 beds

|

2 baths

|

1,368 sq ft

|

Condo

7565 LAUREATE BLVD UNIT 3408, ORLANDO, F...
Sun City Center 1120 EMERALD DUNES DR, SUN CITY CENTER, ..., Sun City Center, FL 33573
$455,000

2 beds

|

2 baths

|

1,885 sq ft

|

House

1120 EMERALD DUNES DR, SUN CITY CENTER, ...
Community: Sun City Center
On Top of the World 8125 SW 81ST LOOP, OCALA, FL, 34476, Ocala, FL 34476
$318,900

2 beds

|

2 baths

|

1,742 sq ft

|

House

8125 SW 81ST LOOP, OCALA, FL, 34476
Community: On Top of the World
Tohoqua Reserve 1991 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744
$464,900

3 beds

|

2 baths

|

2,056 sq ft

|

House

1991 SPRING SHOWER CIR, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
Plantation at Leesburg 3646 WESTOVER CIR, LEESBURG, FL, 34748, Leesburg, FL 34748
$419,000

2 beds

|

2 baths

|

2,400 sq ft

|

House

3646 WESTOVER CIR, LEESBURG, FL, 34748
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Solivita 537 MONTAGE LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$579,900

3 beds

|

3 baths

|

2,441 sq ft

|

House

537 MONTAGE LN, KISSIMMEE, FL, 34759
Community: Solivita
Solivita 684 GRAND CANAL DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$229,900

2 beds

|

2 baths

|

1,387 sq ft

|

House

684 GRAND CANAL DR, KISSIMMEE, FL, 34759
Community: Solivita
Latitude Margaritaville 726 CORAL REEF WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$524,000

2 beds

|

2 baths

|

1,778 sq ft

|

House

726 CORAL REEF WAY, DAYTONA BEACH, FL, 3...
Spruce Creek North 6468 SW 107TH PL, OCALA, FL, 34476, Ocala, FL 34476
$185,999

2 beds

|

2 baths

|

1,095 sq ft

|

House

6468 SW 107TH PL, OCALA, FL, 34476
Community: Spruce Creek North
Solivita 149 ACADIA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$225,000

2 beds

|

2 baths

|

1,240 sq ft

|

House

149 ACADIA DR, KISSIMMEE, FL, 34759
Community: Solivita
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 4721 TARA VIEW RD, LEESBURG, FL, 34748, Leesburg, FL 34748
$325,000

3 beds

|

2 baths

|

1,979 sq ft

|

House

4721 TARA VIEW RD, LEESBURG, FL, 34748
Sun City Center 2234 NOTTINGHAM GREENS DR # 2234, SUN CI..., Sun City Center, FL 33573
$419,900

3 beds

|

2 baths

|

2,000 sq ft

|

Condo

2234 NOTTINGHAM GREENS DR # 2234, SUN CI...
Community: Sun City Center
Sun City Center 1002 N PEBBLE BEACH BLVD # 1002, SUN CIT..., Sun City Center, FL 33573
$135,000

2 beds

|

1 baths

|

899 sq ft

|

Condo

1002 N PEBBLE BEACH BLVD # 1002, SUN CIT...
Community: Sun City Center
The Villages® 3422 RANDI RD, THE VILLAGES, FL, 32163, The Villages, FL 32163
$412,000

3 beds

|

2 baths

|

1,492 sq ft

|

Villa

3422 RANDI RD, THE VILLAGES, FL, 32163
Community: The Villages®
Royal Highlands 21509 CASTLE VIEW CT, LEESBURG, FL, 3474..., Leesburg, FL 34748
$334,997

3 beds

|

3 baths

|

1,913 sq ft

|

House

21509 CASTLE VIEW CT, LEESBURG, FL, 3474...
Community: Royal Highlands
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Sun City Center 2206 MAYFIELD PALMS LN # 69, SUN CITY CE..., Sun City Center, FL 33573
$257,900

2 beds

|

2 baths

|

1,761 sq ft

|

Condo

2206 MAYFIELD PALMS LN # 69, SUN CITY CE...
Community: Sun City Center
On Top of the World 9841 SW 95TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$409,900

2 beds

|

2 baths

|

1,972 sq ft

|

House

9841 SW 95TH LOOP, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 9010 SW 89TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$529,900

3 beds

|

3 baths

|

2,811 sq ft

|

House

9010 SW 89TH LOOP, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 7698 SW 85TH CIR, OCALA, FL, 34481, Ocala, FL 34481
$329,000

2 beds

|

2 baths

|

1,747 sq ft

|

House

7698 SW 85TH CIR, OCALA, FL, 34481
Community: On Top of the World
Southshore Bay 16909 APRIL PLUSH DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$300,000

2 beds

|

3 baths

|

1,713 sq ft

|

Villa

16909 APRIL PLUSH DR, WIMAUMA, FL, 33598
Community: Southshore Bay

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3,958 homes near Winter Garden
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