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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.
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) VillageWalk at Lake Nona
$400Ks - $1Ms
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...
$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
The Villages® 3405 NURSERY PL, THE VILLAGES, FL, 32163, The Villages, FL 32163
$499,000

3 beds

|

2 baths

|

1,935 sq ft

|

House

3405 NURSERY PL, THE VILLAGES, FL, 32163
Community: The Villages®
Spruce Creek Country Club 13885 DEL WEBB BLVD, SUMMERFIELD, FL, 34..., Summerfield, FL 34491
$420,000

3 beds

|

2 baths

|

2,213 sq ft

|

House

13885 DEL WEBB BLVD, SUMMERFIELD, FL, 34...
Esplanade at Highland Ranch 1027 TIMBERVALE TRL, CLERMONT, FL, 34715, Clermont, FL 34715
$459,000

2 beds

|

2 baths

|

1,911 sq ft

|

House

1027 TIMBERVALE TRL, CLERMONT, FL, 34715
The Villages® 467 WESTON MANOR DR, THE VILLAGES, FL, 3..., The Villages, FL 32162
$475,000

3 beds

|

2 baths

|

1,559 sq ft

|

House

467 WESTON MANOR DR, THE VILLAGES, FL, 3...
Community: The Villages®
Royal Highlands 22217 CALEDONIA DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$285,000

3 beds

|

2 baths

|

1,607 sq ft

|

House

22217 CALEDONIA DR, LEESBURG, FL, 34748
Community: Royal Highlands
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 1140 EUREKA MILL RUN, THE VILLAGES, FL, ..., The Villages, FL 32162
$485,000

3 beds

|

2 baths

|

1,741 sq ft

|

House

1140 EUREKA MILL RUN, THE VILLAGES, FL, ...
Community: The Villages®
The Villages® 2449 KINGSTREE PL, THE VILLAGES, FL, 321..., The Villages, FL 32162
$284,900

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

2449 KINGSTREE PL, THE VILLAGES, FL, 321...
Community: The Villages®
Sun City Center 1112 JASMINE CREEK CT, SUN CITY CENTER, ..., Sun City Center, FL 33573
$339,000

3 beds

|

2 baths

|

1,497 sq ft

|

House

1112 JASMINE CREEK CT, SUN CITY CENTER, ...
Community: Sun City Center
The Villages® 2461 MERIDA CIR, THE VILLAGES, FL, 32162, The Villages, FL 32162
$409,900

3 beds

|

2 baths

|

2,145 sq ft

|

House

2461 MERIDA CIR, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 5220 HORSFORD PATH, THE VILLAGES, FL, 32..., The Villages, FL 32163
$749,900

3 beds

|

2 baths

|

2,058 sq ft

|

House

5220 HORSFORD PATH, THE VILLAGES, FL, 32...
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 1047 TIMBERVALE TRL, CLERMONT, FL, 34715, Clermont, FL 34715
$459,900

2 beds

|

2 baths

|

1,911 sq ft

|

House

1047 TIMBERVALE TRL, CLERMONT, FL, 34715
The Villages® 1985 ABORDALE LN, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$850,000

3 beds

|

2 baths

|

2,629 sq ft

|

House

1985 ABORDALE LN, THE VILLAGES, FL, 3216...
Community: The Villages®
The Country Club of Mount Dora 9089 SAINT ANDREWS WAY, MOUNT DORA, FL, ..., Mount Dora, FL 32757
$355,000

3 beds

|

2 baths

|

1,587 sq ft

|

House

9089 SAINT ANDREWS WAY, MOUNT DORA, FL, ...
Sun City Center 1012 WARWICK CT, SUN CITY CENTER, FL, 33..., Sun City Center, FL 33573
$180,000

2 beds

|

2 baths

|

920 sq ft

|

House

1012 WARWICK CT, SUN CITY CENTER, FL, 33...
Community: Sun City Center
Sun City Center 1806 WOLF LAUREL DR, SUN CITY CENTER, FL..., Sun City Center, FL 33573
$395,000

2 beds

|

2 baths

|

1,890 sq ft

|

House

1806 WOLF LAUREL DR, 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
The Villages® 2111 HARSTON TRL, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$354,900

3 beds

|

2 baths

|

1,392 sq ft

|

House

2111 HARSTON TRL, THE VILLAGES, FL, 3216...
Community: The Villages®
Stonecrest 17066 SE 111TH TERRACE RD, SUMMERFIELD, ..., Summerfield, FL 34491
$665,000

3 beds

|

2 baths

|

2,502 sq ft

|

House

17066 SE 111TH TERRACE RD, SUMMERFIELD, ...
Community: Stonecrest
Spruce Creek Country Club 11759 SE 91ST CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$399,000

3 beds

|

2 baths

|

2,120 sq ft

|

House

11759 SE 91ST CIR, SUMMERFIELD, FL, 3449...
The Lakes at Harmony 7465 WING SPAN WAY, HARMONY, FL, 34773, Harmony, FL 34773
$510,000

4 beds

|

3 baths

|

2,289 sq ft

|

House

7465 WING SPAN WAY, HARMONY, FL, 34773
The Villages® 2188 GORDON PATH, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$405,000

3 beds

|

2 baths

|

1,539 sq ft

|

House

2188 GORDON PATH, THE VILLAGES, FL, 3216...
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 1308 CRYSTAL GREENS DR, SUN CITY CENTER,..., Sun City Center, FL 33573
$529,900

3 beds

|

2 baths

|

2,117 sq ft

|

House

1308 CRYSTAL GREENS DR, SUN CITY CENTER,...
Community: Sun City Center
The Villages® 2212 YEAMANS PL, THE VILLAGES, FL, 32162, The Villages, FL 32162
$409,200

3 beds

|

2 baths

|

1,488 sq ft

|

House

2212 YEAMANS PL, THE VILLAGES, FL, 32162
Community: The Villages®
Royal Highlands 21849 TARTAN ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$449,900

3 beds

|

2 baths

|

2,074 sq ft

|

House

21849 TARTAN ST, LEESBURG, FL, 34748
Community: Royal Highlands
The Villages® 3261 WISE WAY, THE VILLAGES, FL, 32163, The Villages, FL 32163
$800,000

3 beds

|

3 baths

|

2,376 sq ft

|

House

3261 WISE WAY, THE VILLAGES, FL, 32163
Community: The Villages®
Del Webb Orlando 507 PAMPLONA PL, DAVENPORT, FL, 33837, Davenport, FL 33837
$309,900

2 beds

|

2 baths

|

1,470 sq ft

|

House

507 PAMPLONA PL, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Del Webb Orlando 246 TOMELLOSO WAY, DAVENPORT, FL, 33837, Davenport, FL 33837
$464,900

2 beds

|

2 baths

|

2,100 sq ft

|

House

246 TOMELLOSO WAY, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Spruce Creek Country Club 13625 SE 93RD COURT RD, SUMMERFIELD, FL,..., Summerfield, FL 34491
$335,900

2 beds

|

2 baths

|

1,951 sq ft

|

House

13625 SE 93RD COURT RD, SUMMERFIELD, FL,...
Del Webb Orlando 142 MAGELLAN CT, DAVENPORT, FL, 33837, Davenport, FL 33837
$395,000

2 beds

|

2 baths

|

1,617 sq ft

|

House

142 MAGELLAN CT, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Spruce Creek South 9661 SE 173RD PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$224,900

3 beds

|

2 baths

|

1,542 sq ft

|

House

9661 SE 173RD PL, SUMMERFIELD, FL, 34491
Community: Spruce Creek South
Spruce Creek South 10338 SE 178TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$239,900

2 beds

|

2 baths

|

1,008 sq ft

|

House

10338 SE 178TH ST, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
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 1372 LOMBARDI CT, POINCIANA, FL, 34759, Poinciana, FL 34759
$311,900

2 beds

|

2 baths

|

1,366 sq ft

|

House

1372 LOMBARDI CT, POINCIANA, FL, 34759
Community: Solivita
The Villages® 1404 TORREY PINES DR, THE VILLAGES, FL, ..., The Villages, FL 32159
$239,900

2 beds

|

2 baths

|

1,040 sq ft

|

Manufactured Home

1404 TORREY PINES DR, THE VILLAGES, FL, ...
Community: The Villages®
The Villages® 3243 MANSFIELD ST, THE VILLAGES, FL, 321..., The Villages, FL 32162
$299,900

2 beds

|

2 baths

|

1,156 sq ft

|

House

3243 MANSFIELD ST, THE VILLAGES, FL, 321...
Community: The Villages®
Bridgewater Landing 5725 STOCKPORT ST, RIVERVIEW, FL, 33578, Riverview, FL 33578
$460,000

2 beds

|

2 baths

|

1,791 sq ft

|

House

5725 STOCKPORT ST, RIVERVIEW, FL, 33578
Community: Bridgewater Landing
Tarawood 10403 S DREW BRYANT CIR, FLORAL CITY, FL..., Floral City, FL 34436
$280,000

3 beds

|

2 baths

|

1,956 sq ft

|

House

10403 S DREW BRYANT CIR, FLORAL CITY, FL...
Community: Tarawood
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Royal Highlands 5622 KING JAMES AVE, LEESBURG, FL, 34748, Leesburg, FL 34748
$283,000

2 beds

|

2 baths

|

1,295 sq ft

|

House

5622 KING JAMES AVE, LEESBURG, FL, 34748
Community: Royal Highlands
Mirada 31451 MONIKER MAST LN, SAN ANTONIO, FL, ..., San Antonio, FL 33576
$260,000

2 beds

|

2 baths

|

1,405 sq ft

|

Villa

31451 MONIKER MAST LN, SAN ANTONIO, FL, ...
Community: Mirada
The Villages® 9224 SE 167TH FORD ST, THE VILLAGES, FL,..., The Villages, FL 32162
$359,000

3 beds

|

2 baths

|

1,671 sq ft

|

Villa

9224 SE 167TH FORD ST, THE VILLAGES, FL,...
Community: The Villages®
Sun City Center 1707 NEW BEDFORD DR, SUN CITY CENTER, FL..., Sun City Center, FL 33573
$365,000

2 beds

|

2 baths

|

1,479 sq ft

|

House

1707 NEW BEDFORD DR, SUN CITY CENTER, FL...
Community: Sun City Center
Royal Highlands 21502 KING HENRY AVE, LEESBURG, FL, 3474..., Leesburg, FL 34748
$294,900

3 beds

|

2 baths

|

1,886 sq ft

|

House

21502 KING HENRY AVE, LEESBURG, FL, 3474...
Community: Royal Highlands

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3,958 homes near Winter Garden
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