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

3,964 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) 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
Del Webb Orlando 328 TOLDEDO RD, DAVENPORT, FL, 33837, Davenport, FL 33837
$309,900

3 beds

|

2 baths

|

1,435 sq ft

|

House

328 TOLDEDO RD, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Spruce Creek Country Club 13786 SE 88TH CT, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$329,000

3 beds

|

2 baths

|

2,025 sq ft

|

House

13786 SE 88TH CT, SUMMERFIELD, FL, 34491
Oak Run 10843 SW 91ST TER, OCALA, FL, 34481, Ocala, FL 34481
$240,000

2 beds

|

2 baths

|

1,432 sq ft

|

House

10843 SW 91ST TER, OCALA, FL, 34481
Community: Oak Run
The Villages® 1482 AZTECA LOOP, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$350,000

2 beds

|

2 baths

|

1,499 sq ft

|

Villa

1482 AZTECA LOOP, THE VILLAGES, FL, 3216...
Community: The Villages®
Foxwood Lake Estates 5027 FOREST CREST DR, LAKELAND, FL, 3381..., Lakeland, FL 33810
$203,000

2 beds

|

2 baths

|

1,248 sq ft

|

Manufactured Home

5027 FOREST CREST DR, LAKELAND, FL, 3381...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Spruce Creek Country Club 14235 SE 85TH AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$260,000

2 beds

|

2 baths

|

1,148 sq ft

|

House

14235 SE 85TH AVE, SUMMERFIELD, FL, 3449...
Pelican Bay Daytona Beach 129 BLUE HERON DR D, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119
$184,000

2 beds

|

2 baths

|

1,192 sq ft

|

Condo

129 BLUE HERON DR D, DAYTONA BEACH, FL, ...
Sun City Center 2325 W DEL WEBB BLVD, SUN CITY CENTER, F..., Sun City Center, FL 33573
$307,000

3 beds

|

2 baths

|

1,573 sq ft

|

House

2325 W DEL WEBB BLVD, SUN CITY CENTER, F...
Community: Sun City Center
Del Webb Orlando 688 CORDOBA DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$429,900

3 beds

|

2 baths

|

2,116 sq ft

|

House

688 CORDOBA DR, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Majestic Oaks Ocala 5910 SW 89TH ST, OCALA, FL, 34476, Ocala, FL 34476
$278,000

3 beds

|

2 baths

|

1,607 sq ft

|

House

5910 SW 89TH ST, OCALA, FL, 34476
Community: Majestic Oaks Ocala
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.
Pelican Bay Daytona Beach 105 WOOD DUCK CIR # 1C, DAYTONA BEACH, F..., Daytona Beach, FL 32119
$197,000

2 beds

|

2 baths

|

1,242 sq ft

|

Condo

105 WOOD DUCK CIR # 1C, DAYTONA BEACH, F...
Solivita 362 VIA TORRENTE DR, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759
$399,000

2 beds

|

2 baths

|

1,705 sq ft

|

House

362 VIA TORRENTE DR, KISSIMMEE, FL, 3475...
Community: Solivita
Del Webb Orlando 108 LA CRESTA CT, DAVENPORT, FL, 33837, Davenport, FL 33837
$359,900

3 beds

|

2 baths

|

1,435 sq ft

|

House

108 LA CRESTA CT, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Sun City Center 1804 PACIFIC DUNES DR, SUN CITY CENTER, ..., Sun City Center, FL 33573
$439,900

2 beds

|

3 baths

|

2,053 sq ft

|

House

1804 PACIFIC DUNES DR, SUN CITY CENTER, ...
Community: Sun City Center
The Villages® 2410 LITTLE MOUNTAIN LOOP, THE VILLAGES,..., The Villages, FL 32162
$439,000

3 beds

|

2 baths

|

1,896 sq ft

|

House

2410 LITTLE MOUNTAIN LOOP, THE VILLAGES,...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Spruce Creek South 17890 SE 96TH CT, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$219,900

2 beds

|

2 baths

|

1,008 sq ft

|

House

17890 SE 96TH CT, SUMMERFIELD, FL, 34491
Community: Spruce Creek South
The Villages® 1486 OLYMPIA ST, THE VILLAGES, FL, 32163, The Villages, FL 32163
$319,900

2 beds

|

2 baths

|

1,163 sq ft

|

Villa

1486 OLYMPIA ST, THE VILLAGES, FL, 32163
Community: The Villages®
Sun City Center 2003 WEDGE CT, SUN CITY CENTER, FL, 3357..., Sun City Center, FL 33573
$414,000

2 beds

|

2 baths

|

2,185 sq ft

|

House

2003 WEDGE CT, SUN CITY CENTER, FL, 3357...
Community: Sun City Center
The Villages® 17274 SE 85TH WILLOWICK CIR, THE VILLAGE..., The Villages, FL 32162
$710,000

3 beds

|

2 baths

|

2,522 sq ft

|

House

17274 SE 85TH WILLOWICK CIR, THE VILLAGE...
Community: The Villages®
Tohoqua Reserve 1972 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744
$535,000

3 beds

|

3 baths

|

2,797 sq ft

|

House

1972 SPRING SHOWER CIR, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
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.
The Villages® 5766 HENRY LOOP, THE VILLAGES, FL, 32163, The Villages, FL 32163
$750,000

3 beds

|

2 baths

|

1,994 sq ft

|

House

5766 HENRY LOOP, THE VILLAGES, FL, 32163
Community: The Villages®
Spruce Creek South 17915 SE 102ND TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$269,900

3 beds

|

2 baths

|

1,726 sq ft

|

House

17915 SE 102ND TER, SUMMERFIELD, FL, 344...
Community: Spruce Creek South
Plantation at Leesburg 4344 RIVER RIDGE DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$269,900

2 beds

|

2 baths

|

1,554 sq ft

|

House

4344 RIVER RIDGE DR, LEESBURG, FL, 34748
Stone Creek 8491 SW 52ND LANE RD, OCALA, FL, 34481, Ocala, FL 34481
$355,750

3 beds

|

2 baths

|

1,697 sq ft

|

House

8491 SW 52ND LANE RD, OCALA, FL, 34481
Community: Stone Creek
On Top of the World 9770 SW 97TH PL, OCALA, FL, 34481, Ocala, FL 34481
$269,900

3 beds

|

3 baths

|

1,736 sq ft

|

House

9770 SW 97TH PL, 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® 164 PALERMO PL, THE VILLAGES, FL, 32159, The Villages, FL 32159
$565,000

4 beds

|

3 baths

|

2,202 sq ft

|

House

164 PALERMO PL, THE VILLAGES, FL, 32159
Community: The Villages®
Ocala Palms 5891 NW 26TH ST, OCALA, FL, 34482, Ocala, FL 34482
$329,900

3 beds

|

3 baths

|

1,781 sq ft

|

House

5891 NW 26TH ST, OCALA, FL, 34482
Community: Ocala Palms
Southshore Bay 17319 HOLLY WELL AVE, WIMAUMA, FL, 33598, Wimauma, FL 33598
$332,000

2 beds

|

2 baths

|

1,614 sq ft

|

Villa

17319 HOLLY WELL AVE, WIMAUMA, FL, 33598
Community: Southshore Bay
Stonecrest 10994 SE 168TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491
$579,000

3 beds

|

3 baths

|

2,742 sq ft

|

House

10994 SE 168TH LOOP, SUMMERFIELD, FL, 34...
Community: Stonecrest
The Villages® 518 SAINT ANDREWS BLVD, LADY LAKE, FL, 3..., Lady Lake, FL 32159
$249,900

2 beds

|

2 baths

|

1,248 sq ft

|

Manufactured Home

518 SAINT ANDREWS BLVD, LADY LAKE, FL, 3...
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.
Lakeside Landings 4976 SANDPIPER DR, OXFORD, FL, 34484, Oxford, FL 34484
$524,900

4 beds

|

2 baths

|

2,696 sq ft

|

House

4976 SANDPIPER DR, OXFORD, FL, 34484
Community: Lakeside Landings
On Top of the World 10327 SW 96TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$435,000

2 beds

|

2 baths

|

2,019 sq ft

|

House

10327 SW 96TH LOOP, OCALA, FL, 34481
Community: On Top of the World
Latitude Margaritaville 484 LANDSHARK BLVD, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$405,000

2 beds

|

2 baths

|

1,464 sq ft

|

House

484 LANDSHARK BLVD, DAYTONA BEACH, FL, 3...
Latitude Margaritaville 317 GYPSY PALACE LN, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$385,000

2 beds

|

2 baths

|

1,321 sq ft

|

House

317 GYPSY PALACE LN, DAYTONA BEACH, FL, ...
The Villages® 1329 GASTON LOOP, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$525,000

3 beds

|

2 baths

|

2,000 sq ft

|

House

1329 GASTON LOOP, THE VILLAGES, FL, 3216...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Latitude Margaritaville 324 CORAL REEF WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$468,900

2 beds

|

2 baths

|

1,563 sq ft

|

Villa

324 CORAL REEF WAY, DAYTONA BEACH, FL, 3...
Latitude Margaritaville 540 GOOD LIFE WAY, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32124
$649,000

2 beds

|

2 baths

|

1,922 sq ft

|

House

540 GOOD LIFE WAY, DAYTONA BEACH, FL, 32...
Lake Jovita Golf and Country Club 13302 TRAILING MOSS DR, DADE CITY, FL, 3..., Dade City, FL 33525
$875,000

4 beds

|

3 baths

|

2,632 sq ft

|

House

13302 TRAILING MOSS DR, DADE CITY, FL, 3...
Lakeside Landings 10460 SILVER MAPLE AVE, OXFORD, FL, 3448..., Oxford, FL 34484
$340,000

3 beds

|

2 baths

|

1,832 sq ft

|

House

10460 SILVER MAPLE AVE, OXFORD, FL, 3448...
Community: Lakeside Landings
Lake Ashton 4313 HEATH LAND LN, LAKE WALES, FL, 3385..., Lake Wales, FL 33859
$359,900

3 beds

|

2 baths

|

1,838 sq ft

|

House

4313 HEATH LAND LN, LAKE WALES, FL, 3385...
Community: Lake Ashton

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3,964 homes near Winter Garden
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