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

3,584 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 - $2Ms
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
$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 (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 - $500Ks
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 - $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
$200Ks - $200Ks
Cypress Lakes, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1987 - 2016 | 1,604 homes
5 rating (3 reviews) Lake Ashton
$200Ks - $500Ks
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
$300Ks - $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) VillageWalk at Lake Nona
$400Ks - $900Ks
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...
$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 - $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 - $400Ks
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
4.3 rating (15 reviews) Del Webb Orlando
$200Ks - $400Ks
Del Webb Orlando, Davenport, FL
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes
No reviews yet Pine Run Estates
<$100k - $400Ks
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
Valencia Lakes 16301 GARNET GLEN PL, WIMAUMA, FL, 33598, Wimauma, FL 33598
$669,900

3 beds

|

4 baths

|

2,723 sq ft

|

House

16301 GARNET GLEN PL, WIMAUMA, FL, 33598
Community: Valencia Lakes
Venetian Bay 334 CARYOTA CT, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$463,000

3 beds

|

2 baths

|

1,616 sq ft

|

House

334 CARYOTA CT, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
Marco Polo Village 11123 SW 53RD CIR, OCALA, FL, 34476, Ocala, FL 34476
$285,000

3 beds

|

2 baths

|

1,731 sq ft

|

House

11123 SW 53RD CIR, OCALA, FL, 34476
Community: Marco Polo Village
Del Webb Oasis 16041 HONEY HARVEST ST, WINTER GARDEN, F..., Winter Garden, FL 34787
$776,943

4 beds

|

5 baths

|

2,837 sq ft

|

House

16041 HONEY HARVEST ST, WINTER GARDEN, F...
Community: Del Webb Oasis
Del Webb Oasis 12904 HARVEST RAIN AVE, WINTER GARDEN, F..., Winter Garden, FL 34787
$825,285

5 beds

|

5 baths

|

3,101 sq ft

|

House

12904 HARVEST RAIN AVE, WINTER GARDEN, F...
Community: Del Webb Oasis
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
On Top of the World 9722 SW 95TH CT C, OCALA, FL, 34481, Ocala, FL 34481
$189,900

2 beds

|

2 baths

|

1,412 sq ft

|

Villa

9722 SW 95TH CT C, OCALA, FL, 34481
Community: On Top of the World
Palm Cay 8449 SW 106TH PL, OCALA, FL, 34481, Ocala, FL 34481
$174,900

2 beds

|

2 baths

|

1,114 sq ft

|

House

8449 SW 106TH PL, OCALA, FL, 34481
Community: Palm Cay
Sun City Center 1526 LELAND DR, SUN CITY CENTER, FL, 335..., Sun City Center, FL 33573
$199,900

2 beds

|

2 baths

|

1,878 sq ft

|

Condo

1526 LELAND DR, SUN CITY CENTER, FL, 335...
Community: Sun City Center
Palm Cay 10881 SW 79TH TER, OCALA, FL, 34476, Ocala, FL 34476
$183,000

2 beds

|

2 baths

|

1,112 sq ft

|

House

10881 SW 79TH TER, OCALA, FL, 34476
Community: Palm Cay
Pine Run Estates 9841 SW 102ND PL, OCALA, FL, 34481, Ocala, FL 34481
$168,500

2 beds

|

2 baths

|

1,508 sq ft

|

House

9841 SW 102ND 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.
Majestic Oaks Ocala 4713 SW 86TH LN, OCALA, FL, 34476, Ocala, FL 34476
$289,999

4 beds

|

3 baths

|

2,470 sq ft

|

House

4713 SW 86TH LN, OCALA, FL, 34476
Community: Majestic Oaks Ocala
Southshore Bay 17554 HOLLY WELL AVE, WIMAUMA, FL, 33598, Wimauma, FL 33598
$336,900

2 beds

|

3 baths

|

1,737 sq ft

|

Villa

17554 HOLLY WELL AVE, WIMAUMA, FL, 33598
Community: Southshore Bay
Del Webb Oasis 13562 PEARL BEACH ST, WINTER GARDEN, FL,..., Winter Garden, FL 34787
$435,000

2 beds

|

2 baths

|

1,574 sq ft

|

Villa

13562 PEARL BEACH ST, WINTER GARDEN, FL,...
Community: Del Webb Oasis
Stone Creek 6083 SW 93RD CIR, OCALA, FL, 34481, Ocala, FL 34481
$300,000

3 beds

|

2 baths

|

1,851 sq ft

|

House

6083 SW 93RD CIR, OCALA, FL, 34481
Community: Stone Creek
The Villages® 1380 MAYESVILLE WAY, THE VILLAGES, FL, 3..., The Villages, FL 32162
$685,000

3 beds

|

2 baths

|

2,490 sq ft

|

House

1380 MAYESVILLE WAY, THE VILLAGES, FL, 3...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Highland Lakes 26548 DEUCE CT, LEESBURG, FL, 34748, Leesburg, FL 34748
$219,900

2 beds

|

2 baths

|

1,120 sq ft

|

House

26548 DEUCE CT, LEESBURG, FL, 34748
Community: Highland Lakes
Sun City Center 202 S PEBBLE BEACH BLVD # 202, SUN CITY ..., Sun City Center, FL 33573
$219,700

3 beds

|

2 baths

|

1,506 sq ft

|

Condo

202 S PEBBLE BEACH BLVD # 202, SUN CITY ...
Community: Sun City Center
On Top of the World 9735 SW 96TH ST, OCALA, FL, 34481, Ocala, FL 34481
$253,000

2 beds

|

2 baths

|

1,565 sq ft

|

Halfplex

9735 SW 96TH ST, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 10597 SW 90TH STREET RD, OCALA, FL, 3448..., Ocala, FL 34481
$338,500

2 beds

|

2 baths

|

1,651 sq ft

|

House

10597 SW 90TH STREET RD, OCALA, FL, 3448...
Community: On Top of the World
The Villages® 1256 MIRA MAR AVE # 1256, LADY LAKE, FL,..., Lady Lake, FL 32159
$382,500

2 beds

|

2 baths

|

1,437 sq ft

|

Condo

1256 MIRA MAR AVE # 1256, LADY LAKE, FL,...
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.
Sun City Center 1624 COSTA ST, SUN CITY CENTER, FL, 3357..., Sun City Center, FL 33573
$225,000

2 beds

|

2 baths

|

1,200 sq ft

|

House

1624 COSTA ST, SUN CITY CENTER, FL, 3357...
Community: Sun City Center
Lake Ashton 5332 HOGAN LN, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$438,888

2 beds

|

2 baths

|

1,677 sq ft

|

House

5332 HOGAN LN, WINTER HAVEN, FL, 33884
Community: Lake Ashton
The Villages® 805 ROYAL PALM AVE, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$184,900

2 beds

|

2 baths

|

984 sq ft

|

Manufactured Home

805 ROYAL PALM AVE, LADY LAKE, FL, 32159
Community: The Villages®
Valencia Lakes 15911 COBBLE MILL DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$360,000

3 beds

|

2 baths

|

1,868 sq ft

|

House

15911 COBBLE MILL DR, WIMAUMA, FL, 33598
Community: Valencia Lakes
Latitude Margaritaville 962 ATTITUDE AVE, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124
$574,900

3 beds

|

2 baths

|

1,771 sq ft

|

House

962 ATTITUDE AVE, DAYTONA BEACH, FL, 321...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Sun City Center 102 CAMBRIDGE TRL APT 225, SUN CITY CENT..., Sun City Center, FL 33573
$100,000

2 beds

|

2 baths

|

960 sq ft

|

Condo

102 CAMBRIDGE TRL APT 225, SUN CITY CENT...
Community: Sun City Center
Venetian Bay 3114 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$509,000

4 beds

|

4 baths

|

2,338 sq ft

|

House

3114 MELETO BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
The Villages® 5371 WARM SPRINGS AVE, WILDWOOD, FL, 347..., Wildwood, FL 34785
$295,000

2 beds

|

1 baths

|

996 sq ft

|

House

5371 WARM SPRINGS AVE, WILDWOOD, FL, 347...
Community: The Villages®
Pelican Bay Daytona Beach 101 BOB WHITE CT APT 1, DAYTONA BEACH, F..., Daytona Beach, FL 32119
$199,900

3 beds

|

3 baths

|

1,721 sq ft

|

Condo

101 BOB WHITE CT APT 1, DAYTONA BEACH, F...
Sun City Center 719 WINTERBROOKE WAY, SUN CITY CENTER, F..., Sun City Center, FL 33573
$300,000

3 beds

|

2 baths

|

1,550 sq ft

|

House

719 WINTERBROOKE WAY, SUN CITY CENTER, F...
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.
On Top of the World 9070 SW 106TH AVE, OCALA, FL, 34481, Ocala, FL 34481
$394,493

2 beds

|

2 baths

|

1,983 sq ft

|

House

9070 SW 106TH AVE, OCALA, FL, 34481
Community: On Top of the World
Latitude Margaritaville 245 GYPSY PALACE LN, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$365,800

2 beds

|

2 baths

|

1,205 sq ft

|

House

245 GYPSY PALACE LN, DAYTONA BEACH, FL, ...
Sun City Center 821 CHIPPER DR, SUN CITY CENTER, FL, 335..., Sun City Center, FL 33573
$333,900

3 beds

|

2 baths

|

1,568 sq ft

|

Villa

821 CHIPPER DR, SUN CITY CENTER, FL, 335...
Community: Sun City Center
The Villages® 1080 TIPTON LN, THE VILLAGES, FL, 32163, The Villages, FL 32163
$375,000

3 beds

|

2 baths

|

1,357 sq ft

|

Villa

1080 TIPTON LN, THE VILLAGES, FL, 32163
Community: The Villages®
On Top of the World 9152 SW 91ST CIR, OCALA, FL, 34481, Ocala, FL 34481
$205,000

2 beds

|

2 baths

|

1,345 sq ft

|

House

9152 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
The Villages® 1965 GATEHOUSE TER, THE VILLAGES, FL, 32..., The Villages, FL 32163
$629,500

3 beds

|

2 baths

|

2,035 sq ft

|

House

1965 GATEHOUSE TER, THE VILLAGES, FL, 32...
Community: The Villages®
Windermere 828 WINDERMERE BLVD, INVERNESS, FL, 3445..., Inverness, FL 34453
$209,900

2 beds

|

2 baths

|

1,202 sq ft

|

Villa

828 WINDERMERE BLVD, INVERNESS, FL, 3445...
Community: Windermere
On Top of the World 8888 SW 95TH LN D, OCALA, FL, 34481, Ocala, FL 34481
$188,500

2 beds

|

2 baths

|

1,748 sq ft

|

Villa

8888 SW 95TH LN D, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 8666 SW 92ND LN C, OCALA, FL, 34481, Ocala, FL 34481
$164,889

2 beds

|

2 baths

|

1,394 sq ft

|

Villa

8666 SW 92ND LN C, OCALA, FL, 34481
Community: On Top of the World
Del Webb Sunbridge 3002 VOYAGER AVE, SAINT CLOUD, FL, 34771, Saint Cloud, FL 34771
$693,000

4 beds

|

3 baths

|

2,933 sq ft

|

House

3002 VOYAGER AVE, SAINT CLOUD, FL, 34771
Community: Del Webb Sunbridge

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3,584 homes near Winter Garden
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