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

3,631 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 - $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
$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
$200Ks - $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
$200Ks - $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 - $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) 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
The Villages® 527 BEVILLE PL, THE VILLAGES, FL, 32163, The Villages, FL 32163
$599,999

3 beds

|

2 baths

|

2,050 sq ft

|

House

527 BEVILLE PL, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 2466 SOPER ST, THE VILLAGES, FL, 32163, The Villages, FL 32163
$289,000

2 beds

|

2 baths

|

1,148 sq ft

|

Villa

2466 SOPER ST, THE VILLAGES, FL, 32163
Community: The Villages®
Majestic Oaks Ocala 8761 SW 52ND CT, OCALA, FL, 34476, Ocala, FL 34476
$387,000

3 beds

|

2 baths

|

2,496 sq ft

|

House

8761 SW 52ND CT, OCALA, FL, 34476
Community: Majestic Oaks Ocala
The Villages® 17860 SE 89TH NATCHEZ AVE, THE VILLAGES,..., The Villages, FL 32162
$349,000

3 beds

|

2 baths

|

1,625 sq ft

|

House

17860 SE 89TH NATCHEZ AVE, THE VILLAGES,...
Community: The Villages®
Plantation at Leesburg 25301 FOREST OAK CT, LEESBURG, FL, 34748, Leesburg, FL 34748
$380,000

2 beds

|

2 baths

|

2,489 sq ft

|

House

25301 FOREST OAK CT, LEESBURG, FL, 34748
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Plantation at Leesburg 24104 ROBINWOOD ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$350,000

2 beds

|

2 baths

|

2,447 sq ft

|

House

24104 ROBINWOOD ST, LEESBURG, FL, 34748
Plantation at Leesburg 24112 ROBINWOOD ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$359,000

2 beds

|

2 baths

|

2,071 sq ft

|

House

24112 ROBINWOOD ST, LEESBURG, FL, 34748
Pelican Bay Daytona Beach 124 LOON CT, DAYTONA BEACH, FL, 32119, Daytona Beach, FL 32119
$294,999

2 beds

|

2 baths

|

1,714 sq ft

|

House

124 LOON CT, DAYTONA BEACH, FL, 32119
The Villages® 1124 AVENIDA DE LAS CASAS # 1124, LADY L..., Lady Lake, FL 32159
$450,000

2 beds

|

3 baths

|

1,780 sq ft

|

Villa

1124 AVENIDA DE LAS CASAS # 1124, LADY L...
Community: The Villages®
The Villages® 1120 AVENIDA DE LAS CASAS, THE VILLAGES,..., The Villages, FL 32159
$434,500

2 beds

|

3 baths

|

1,575 sq ft

|

Villa

1120 AVENIDA DE LAS CASAS, THE VILLAGES,...
Community: The Villages®
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.
Esplanade at Highland Ranch 967 BRAEWOOD DR, CLERMONT, FL, 34715, Clermont, FL 34715
$471,000

2 beds

|

2 baths

|

1,778 sq ft

|

House

967 BRAEWOOD DR, CLERMONT, FL, 34715
Sun City Center 1530 INGRAM DR # 1530, SUN CITY CENTER, ..., Sun City Center, FL 33573
$193,990

2 beds

|

2 baths

|

1,642 sq ft

|

Condo

1530 INGRAM DR # 1530, SUN CITY CENTER, ...
Community: Sun City Center
Sun City Center 2122 HEREFORD DR # 511, SUN CITY CENTER,..., Sun City Center, FL 33573
$175,000

2 beds

|

2 baths

|

1,150 sq ft

|

Condo

2122 HEREFORD DR # 511, SUN CITY CENTER,...
Community: Sun City Center
Sun City Center 2115 N HALCYON DR # 510, SUN CITY CENTER..., Sun City Center, FL 33573
$209,900

2 beds

|

2 baths

|

1,203 sq ft

|

Condo

2115 N HALCYON DR # 510, SUN CITY CENTER...
Community: Sun City Center
Pine Run Estates 9430 SW 102ND PL, OCALA, FL, 34481, Ocala, FL 34481
$145,000

2 beds

|

2 baths

|

1,040 sq ft

|

House

9430 SW 102ND PL, OCALA, FL, 34481
Community: Pine Run Estates
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 7326 SE 173RD ARLINGTON LOOP, THE VILLAG..., The Villages, FL 32162
$325,000

3 beds

|

2 baths

|

1,490 sq ft

|

House

7326 SE 173RD ARLINGTON LOOP, THE VILLAG...
Community: The Villages®
Mirada 10381 TUPPER CAY DR, SAN ANTONIO, FL, 33..., San Antonio, FL 33576
$399,990

2 beds

|

2 baths

|

1,968 sq ft

|

House

10381 TUPPER CAY DR, SAN ANTONIO, FL, 33...
Community: Mirada
Lake Ashton 4315 ASHTON CLUB DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859
$499,900

3 beds

|

2 baths

|

2,229 sq ft

|

House

4315 ASHTON CLUB DR, LAKE WALES, FL, 338...
Community: Lake Ashton
The Villages® 12185 NE 51ST CIR, OXFORD, FL, 34484, Oxford, FL 34484
$329,900

3 beds

|

2 baths

|

1,889 sq ft

|

House

12185 NE 51ST CIR, OXFORD, FL, 34484
Community: The Villages®
Solivita 759 LARGO PASS, POINCIANA, FL, 34759, Poinciana, FL 34759
$380,999

2 beds

|

2 baths

|

2,038 sq ft

|

House

759 LARGO PASS, POINCIANA, 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.
Summer Trees 128 CROOKED PINE RD, PORT ORANGE, FL, 32..., Port Orange, FL 32128
$299,900

3 beds

|

2 baths

|

1,268 sq ft

|

House

128 CROOKED PINE RD, PORT ORANGE, FL, 32...
Community: Summer Trees
Sun City Center 657 MASTERPIECE DR # 154, SUN CITY CENTE..., Sun City Center, FL 33573
$234,000

2 beds

|

2 baths

|

1,543 sq ft

|

Condo

657 MASTERPIECE DR # 154, SUN CITY CENTE...
Community: Sun City Center
Valencia Lakes 16116 CEDAR KEY DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$389,000

2 beds

|

2 baths

|

1,939 sq ft

|

House

16116 CEDAR KEY DR, WIMAUMA, FL, 33598
Community: Valencia Lakes
Sun City Center 2112 ACADIA GREENS DR # 62, SUN CITY CEN..., Sun City Center, FL 33573
$235,000

2 beds

|

2 baths

|

1,194 sq ft

|

Condo

2112 ACADIA GREENS DR # 62, SUN CITY CEN...
Community: Sun City Center
Stone Creek 9664 SW 76TH LANE RD, OCALA, FL, 34481, Ocala, FL 34481
$308,900

3 beds

|

3 baths

|

1,981 sq ft

|

House

9664 SW 76TH LANE RD, OCALA, FL, 34481
Community: Stone Creek
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Del Webb Sunbridge 2900 VOYAGER AVE, SAINT CLOUD, FL, 34771, Saint Cloud, FL 34771
$417,880

3 beds

|

3 baths

|

1,767 sq ft

|

Townhouse

2900 VOYAGER AVE, SAINT CLOUD, FL, 34771
Community: Del Webb Sunbridge
Sun City Center 2039 PRESTANCIA LN, SUN CITY CENTER, FL,..., Sun City Center, FL 33573
$375,000

2 beds

|

2 baths

|

1,528 sq ft

|

House

2039 PRESTANCIA LN, SUN CITY CENTER, FL,...
Community: Sun City Center
Del Webb Minneola 1388 ZESTY CITRUS LN, MINNEOLA, FL, 3471..., Minneola, FL 34715
$725,000

2 beds

|

3 baths

|

2,080 sq ft

|

House

1388 ZESTY CITRUS LN, MINNEOLA, FL, 3471...
Community: Del Webb Minneola
VillageWalk at Lake Nona 11794 BARLETTA DR, ORLANDO, FL, 32827, Orlando, FL 32827
$699,987

3 beds

|

2 baths

|

1,949 sq ft

|

House

11794 BARLETTA DR, ORLANDO, FL, 32827
Legacy of Leesburg 5839 WOODLAND MOSS WAY, LEESBURG, FL, 34..., Leesburg, FL 34748
$327,000

3 beds

|

2 baths

|

1,993 sq ft

|

House

5839 WOODLAND MOSS WAY, LEESBURG, FL, 34...
Community: Legacy of Leesburg
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 Palms 1900 NW 57TH CT, OCALA, FL, 34482, Ocala, FL 34482
$297,900

3 beds

|

2 baths

|

1,692 sq ft

|

House

1900 NW 57TH CT, OCALA, FL, 34482
Community: Ocala Palms
Spruce Creek South 10551 SE 179TH LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$275,000

3 beds

|

2 baths

|

1,690 sq ft

|

House

10551 SE 179TH LN, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
Sun City Center 1810 ATRIUM DR, SUN CITY CENTER, FL, 335..., Sun City Center, FL 33573
$240,000

2 beds

|

2 baths

|

1,212 sq ft

|

Villa

1810 ATRIUM DR, SUN CITY CENTER, FL, 335...
Community: Sun City Center
Legacy of Leesburg 27536 STONEY BROOK DR, LEESBURG, FL, 347..., Leesburg, FL 34748
$299,000

3 beds

|

2 baths

|

1,478 sq ft

|

House

27536 STONEY BROOK DR, LEESBURG, FL, 347...
Community: Legacy of Leesburg
Del Webb Sunbridge 6354 SHIMMERING SHORES LN, SAINT CLOUD, ..., Saint Cloud, FL 34771
$519,900

2 beds

|

2 baths

|

1,670 sq ft

|

House

6354 SHIMMERING SHORES LN, SAINT CLOUD, ...
Community: Del Webb Sunbridge
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Latitude Margaritaville 299 POP TOP LN, DAYTONA BEACH, FL, 32124, Daytona Beach, FL 32124
$419,000

2 beds

|

2 baths

|

1,464 sq ft

|

House

299 POP TOP LN, DAYTONA BEACH, FL, 32124
Pelican Bay Daytona Beach 100 KILLDEER CT, DAYTONA BEACH, FL, 3211..., Daytona Beach, FL 32119
$289,400

3 beds

|

2 baths

|

1,650 sq ft

|

House

100 KILLDEER CT, DAYTONA BEACH, FL, 3211...
Venetian Bay 2913 N ASCIANO CT, NEW SMYRNA BEACH, FL,..., New Smyrna Beach, FL 32168
$1,150,000

4 beds

|

3 baths

|

3,148 sq ft

|

House

2913 N ASCIANO CT, NEW SMYRNA BEACH, FL,...
Community: Venetian Bay
Latitude Margaritaville 1082 CASTAWAY CT, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124
$555,000

2 beds

|

2 baths

|

1,684 sq ft

|

House

1082 CASTAWAY CT, DAYTONA BEACH, FL, 321...
Pelican Bay Daytona Beach 5 SKIMMER CIR, DAYTONA BEACH, FL, 32119, Daytona Beach, FL 32119
$342,900

3 beds

|

3 baths

|

2,086 sq ft

|

House

5 SKIMMER CIR, DAYTONA BEACH, FL, 32119

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3,631 homes near Winter Garden
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