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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
Four Seasons at Orlando 2132 ANTILLES CLUB DR, KISSIMMEE, FL, 34..., Kissimmee, FL 34747
$389,000

2 beds

|

2 baths

|

1,770 sq ft

|

House

2132 ANTILLES CLUB DR, KISSIMMEE, FL, 34...
Four Seasons at Orlando 1638 KEY BAY TRL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$359,900

2 beds

|

2 baths

|

1,583 sq ft

|

Villa

1638 KEY BAY TRL, KISSIMMEE, FL, 34747
On Top of the World 8862 SW 92ND ST D, OCALA, FL, 34481, Ocala, FL 34481
$173,000

2 beds

|

2 baths

|

1,530 sq ft

|

Condo

8862 SW 92ND ST D, OCALA, FL, 34481
Community: On Top of the World
Breakaway Trails 3 FOREST VIEW WAY, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$425,000

3 beds

|

2 baths

|

2,737 sq ft

|

House

3 FOREST VIEW WAY, ORMOND BEACH, FL, 321...
Community: Breakaway Trails
Solivita 504 MILLIFIORA LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$245,000

2 beds

|

2 baths

|

1,512 sq ft

|

House

504 MILLIFIORA LN, KISSIMMEE, FL, 34759
Community: Solivita
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Sun City Center 1905 CANTERBURY LN UNIT 17, SUN CITY CEN..., Sun City Center, FL 33573
$139,000

2 beds

|

2 baths

|

960 sq ft

|

Condo

1905 CANTERBURY LN UNIT 17, SUN CITY CEN...
Community: Sun City Center
Windermere 802 WINDERMERE BLVD, INVERNESS, FL, 3445..., Inverness, FL 34453
$230,000

2 beds

|

2 baths

|

1,284 sq ft

|

House

802 WINDERMERE BLVD, INVERNESS, FL, 3445...
Community: Windermere
Four Seasons at Orlando 2233 ANTILLES CLUB DR, KISSIMMEE, FL, 34..., Kissimmee, FL 34747
$525,000

3 beds

|

2 baths

|

2,042 sq ft

|

House

2233 ANTILLES CLUB DR, KISSIMMEE, FL, 34...
The Villages® 110 TIMBER WAY, WILDWOOD, FL, 34785, Wildwood, FL 34785
$119,500

2 beds

|

2 baths

|

1,352 sq ft

|

Manufactured Home

110 TIMBER WAY, WILDWOOD, FL, 34785
Community: The Villages®
Marion Landing 8668 SW 67TH CT, OCALA, FL, 34476, Ocala, FL 34476
$190,000

3 beds

|

2 baths

|

1,296 sq ft

|

Manufactured Home

8668 SW 67TH CT, OCALA, FL, 34476
Community: Marion Landing
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.
Pine Run Estates 10020 SW 96TH CT, OCALA, FL, 34481, Ocala, FL 34481
$327,000

2 beds

|

2 baths

|

1,342 sq ft

|

House

10020 SW 96TH CT, OCALA, FL, 34481
Community: Pine Run Estates
Latitude Margaritaville 595 GOOD LIFE WAY, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32124
$409,900

2 beds

|

2 baths

|

1,464 sq ft

|

House

595 GOOD LIFE WAY, DAYTONA BEACH, FL, 32...
Solivita 1400 LOMBARDI CT, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$385,000

3 beds

|

2 baths

|

1,723 sq ft

|

House

1400 LOMBARDI CT, KISSIMMEE, FL, 34759
Community: Solivita
Solivita 517 MILANO RD, POINCIANA, FL, 34759, Poinciana, FL 34759
$549,900

3 beds

|

3 baths

|

2,464 sq ft

|

House

517 MILANO RD, POINCIANA, FL, 34759
Community: Solivita
Valencia Lakes 4948 GRAND BANKS DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$539,000

3 beds

|

3 baths

|

2,185 sq ft

|

House

4948 GRAND BANKS DR, WIMAUMA, FL, 33598
Community: Valencia Lakes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Stonecrest 17083 SE 115TH TERRACE RD, SUMMERFIELD, ..., Summerfield, FL 34491
$335,000

3 beds

|

2 baths

|

1,782 sq ft

|

House

17083 SE 115TH TERRACE RD, SUMMERFIELD, ...
Community: Stonecrest
Spruce Creek Country Club 12150 SE 91ST TER, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$349,000

2 beds

|

2 baths

|

1,870 sq ft

|

House

12150 SE 91ST TER, SUMMERFIELD, FL, 3449...
On Top of the World 8677 SW 95TH LN A, OCALA, FL, 34481, Ocala, FL 34481
$169,900

2 beds

|

2 baths

|

1,530 sq ft

|

Villa

8677 SW 95TH LN A, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 8874 SW 95TH ST E, OCALA, FL, 34481, Ocala, FL 34481
$245,900

2 beds

|

2 baths

|

1,761 sq ft

|

Villa

8874 SW 95TH ST E, OCALA, FL, 34481
Community: On Top of the World
Solivita 100 VENTANA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$300,000

2 beds

|

2 baths

|

1,739 sq ft

|

House

100 VENTANA 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.
Twin Lakes 4909 W FOUNTAINWOOD DR, SAINT CLOUD, FL,..., Saint Cloud, FL 34772
$479,000

3 beds

|

3 baths

|

2,365 sq ft

|

House

4909 W FOUNTAINWOOD DR, SAINT CLOUD, FL,...
Community: Twin Lakes
Royal Harbor 5789 BOUNTY CIR, TAVARES, FL, 32778, Tavares, FL 32778
$449,000

4 beds

|

4 baths

|

2,997 sq ft

|

House

5789 BOUNTY CIR, TAVARES, FL, 32778
Community: Royal Harbor
Lake Ashton 4056 ASHTON CLUB DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859
$305,000

2 beds

|

2 baths

|

1,530 sq ft

|

House

4056 ASHTON CLUB DR, LAKE WALES, FL, 338...
Community: Lake Ashton
VillageWalk at Lake Nona 8427 LEATHERLEAF LN, ORLANDO, FL, 32827, Orlando, FL 32827
$439,000

3 beds

|

3 baths

|

1,810 sq ft

|

Townhouse

8427 LEATHERLEAF LN, ORLANDO, FL, 32827
Sun City Center 505 FOXGLOVE CIR B, SUN CITY CENTER, FL,..., Sun City Center, FL 33573
$185,000

2 beds

|

2 baths

|

1,245 sq ft

|

Halfplex

505 FOXGLOVE CIR B, SUN CITY CENTER, FL,...
Community: Sun City Center
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Twin Lakes 5075 TWIN LAKES BLVD, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34772
$679,900

4 beds

|

4 baths

|

2,870 sq ft

|

House

5075 TWIN LAKES BLVD, SAINT CLOUD, FL, 3...
Community: Twin Lakes
The Villages® 594 LACY PL, THE VILLAGES, FL, 32162, The Villages, FL 32162
$349,900

3 beds

|

2 baths

|

1,397 sq ft

|

House

594 LACY PL, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 1502 EL PASO WAY, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$317,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

1502 EL PASO WAY, THE VILLAGES, FL, 3216...
Community: The Villages®
The Lakes at Harmony 3184 SONGBIRD CIR, HARMONY, FL, 34773, Harmony, FL 34773
$469,900

3 beds

|

2 baths

|

1,852 sq ft

|

House

3184 SONGBIRD CIR, HARMONY, FL, 34773
Latitude Margaritaville 962 ATTITUDE AVE, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124
$564,900

3 beds

|

2 baths

|

1,771 sq ft

|

House

962 ATTITUDE AVE, DAYTONA BEACH, FL, 321...
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.
Sullivan Ranch 20945 OLDENBURG LOOP, MOUNT DORA, FL, 32..., Mount Dora, FL 32757
$399,000

3 beds

|

2 baths

|

2,164 sq ft

|

House

20945 OLDENBURG LOOP, MOUNT DORA, FL, 32...
Community: Sullivan Ranch
Kings Ridge 3724 WESTERHAM DR, CLERMONT, FL, 34711, Clermont, FL 34711
$309,900

2 beds

|

2 baths

|

1,410 sq ft

|

House

3724 WESTERHAM DR, CLERMONT, FL, 34711
Community: Kings Ridge
The Villages® 675 KENDALL CT, THE VILLAGES, FL, 32162, The Villages, FL 32162
$275,900

2 beds

|

2 baths

|

1,156 sq ft

|

House

675 KENDALL CT, THE VILLAGES, FL, 32162
Community: The Villages®
Harbor Hills Country Club 5072 GREENS DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$695,000

3 beds

|

3 baths

|

2,712 sq ft

|

House

5072 GREENS DR, LADY LAKE, FL, 32159
Highland Lakes 26632 EVERT ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$279,900

2 beds

|

2 baths

|

1,775 sq ft

|

House

26632 EVERT ST, LEESBURG, FL, 34748
Community: Highland Lakes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Lake Ashton 5332 HOGAN LN, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$438,888

3 beds

|

2 baths

|

1,677 sq ft

|

House

5332 HOGAN LN, WINTER HAVEN, FL, 33884
Community: Lake Ashton
Bridgewater Landing 5714 STOCKPORT ST, RIVERVIEW, FL, 33578, Riverview, FL 33578
$350,000

2 beds

|

2 baths

|

1,516 sq ft

|

Villa

5714 STOCKPORT ST, RIVERVIEW, FL, 33578
Community: Bridgewater Landing
Arlington Ridge 26712 AUGUSTA SPRINGS CIR, LEESBURG, FL,..., Leesburg, FL 34748
$384,900

2 beds

|

2 baths

|

2,211 sq ft

|

House

26712 AUGUSTA SPRINGS CIR, LEESBURG, FL,...
Community: Arlington Ridge
Plantation at Leesburg 26338 GLEN EAGLE DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$289,000

3 beds

|

2 baths

|

1,725 sq ft

|

House

26338 GLEN EAGLE DR, LEESBURG, FL, 34748
Venetian Bay 3325 PINTELLO AVE, NEW SMYRNA BEACH, FL,..., New Smyrna Beach, FL 32168
$394,500

4 beds

|

2 baths

|

1,662 sq ft

|

House

3325 PINTELLO AVE, NEW SMYRNA BEACH, FL,...
Community: Venetian Bay

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3,703 homes near Winter Garden
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