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

108 communities 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
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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) 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
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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® 1536 E SCHWARTZ BLVD, THE VILLAGES, FL, ..., The Villages, FL 32159
$272,500

2 beds

|

2 baths

|

1,040 sq ft

|

House

1536 E SCHWARTZ BLVD, THE VILLAGES, FL, ...
Community: The Villages®
On Top of the World 8819 SW 91ST PL C, OCALA, FL, 34481, Ocala, FL 34481
$220,000

2 beds

|

2 baths

|

1,695 sq ft

|

Villa

8819 SW 91ST PL C, OCALA, FL, 34481
Community: On Top of the World
Latitude Margaritaville 208 OCEAN HAMMOCK LOOP, DAYTONA BEACH, F..., Daytona Beach, FL 32124
$462,800

2 beds

|

2 baths

|

1,482 sq ft

|

House

208 OCEAN HAMMOCK LOOP, DAYTONA BEACH, F...
The Villages® 3223 SYLEWOOD AVE, THE VILLAGES, FL, 321..., The Villages, FL 32163
$525,000

3 beds

|

2 baths

|

1,965 sq ft

|

House

3223 SYLEWOOD AVE, THE VILLAGES, FL, 321...
Community: The Villages®
The Villages® 1305 SANTA MARIA AVE, THE VILLAGES, FL, ..., The Villages, FL 32159
$450,000

2 beds

|

2 baths

|

1,686 sq ft

|

Villa

1305 SANTA MARIA AVE, THE VILLAGES, FL, ...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 3243 MANSFIELD ST, THE VILLAGES, FL, 321..., The Villages, FL 32162
$297,400

2 beds

|

2 baths

|

1,156 sq ft

|

House

3243 MANSFIELD ST, THE VILLAGES, FL, 321...
Community: The Villages®
New Spruce Creek South 10339 SE 179TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$209,000

2 beds

|

2 baths

|

1,008 sq ft

|

House

10339 SE 179TH ST, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
The Villages® 2372 TRAVIS PL, THE VILLAGES, FL, 32162, The Villages, FL 32162
$309,000

2 beds

|

2 baths

|

1,188 sq ft

|

Villa

2372 TRAVIS PL, THE VILLAGES, FL, 32162
Community: The Villages®
Lake Ashton 4429 TURNBERRY LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$359,900

3 beds

|

2 baths

|

1,847 sq ft

|

House

4429 TURNBERRY LN, LAKE WALES, FL, 33859
Community: Lake Ashton
On Top of the World 8660 SW 94TH ST F, OCALA, FL, 34481, Ocala, FL 34481
$172,500

2 beds

|

2 baths

|

1,391 sq ft

|

Villa

8660 SW 94TH ST F, OCALA, FL, 34481
Community: On Top of the World
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 321 SIENA VISTA PL, SUN CITY CENTER, FL,..., Sun City Center, FL 33573
$385,000

3 beds

|

2 baths

|

2,021 sq ft

|

House

321 SIENA VISTA PL, SUN CITY CENTER, FL,...
Community: Sun City Center
Venetian Bay 3069 ISLES WAY, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$395,000

2 beds

|

2 baths

|

1,003 sq ft

|

Townhouse

3069 ISLES WAY, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
SummerGlen 16215 SW 15TH CT, OCALA, FL, 34473, Ocala, FL 34473
$334,900

3 beds

|

2 baths

|

1,859 sq ft

|

House

16215 SW 15TH CT, OCALA, FL, 34473
Community: SummerGlen
Pine Run Estates 9980 SW 101ST LN, OCALA, FL, 34481, Ocala, FL 34481
$179,000

2 beds

|

2 baths

|

1,008 sq ft

|

House

9980 SW 101ST LN, OCALA, FL, 34481
Community: Pine Run Estates
Cherrywood 6084 SW 105TH PL, OCALA, FL, 34476, Ocala, FL 34476
$275,000

3 beds

|

2 baths

|

1,514 sq ft

|

House

6084 SW 105TH PL, OCALA, FL, 34476
Community: Cherrywood
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Solivita 201 LARGO DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$444,000

2 beds

|

2 baths

|

2,419 sq ft

|

House

201 LARGO DR, KISSIMMEE, FL, 34759
Community: Solivita
Stone Creek 5806 SW 87TH AVE, OCALA, FL, 34481, Ocala, FL 34481
$320,900

3 beds

|

2 baths

|

1,469 sq ft

|

House

5806 SW 87TH AVE, OCALA, FL, 34481
Community: Stone Creek
New Latitude Margaritaville 244 GYPSY PALACE LN, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$429,900

2 beds

|

2 baths

|

1,466 sq ft

|

House

244 GYPSY PALACE LN, DAYTONA BEACH, FL, ...
New Highlands Ridge 4464 TOUSSANT DR, AVON PARK, FL, 33825, Avon Park, FL 33825
$464,900

3 beds

|

2 baths

|

2,324 sq ft

|

House

4464 TOUSSANT DR, AVON PARK, FL, 33825
Community: Highlands Ridge
Del Webb Orlando 224 GRANADA LN, DAVENPORT, FL, 33837, Davenport, FL 33837
$439,900

3 beds

|

2 baths

|

1,926 sq ft

|

House

224 GRANADA LN, DAVENPORT, FL, 33837
Community: Del Webb Orlando
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.
New Latitude Margaritaville 575 BEACH BUM BLVD, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$919,900

2 beds

|

3 baths

|

2,339 sq ft

|

House

575 BEACH BUM BLVD, DAYTONA BEACH, FL, 3...
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
Breakaway Trails 3 CRESCENT LAKE WAY, ORMOND BEACH, FL, 3..., Ormond Beach, FL 32174
$649,000

4 beds

|

4 baths

|

3,347 sq ft

|

House

3 CRESCENT LAKE WAY, ORMOND BEACH, FL, 3...
Community: Breakaway Trails
New Latitude Margaritaville 494 LANDSHARK BLVD, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$362,500

2 beds

|

2 baths

|

1,160 sq ft

|

House

494 LANDSHARK BLVD, DAYTONA BEACH, FL, 3...
New Traditions at Lake Ruby 3365 RALEIGH DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$285,000

2 beds

|

2 baths

|

1,295 sq ft

|

House

3365 RALEIGH DR, WINTER HAVEN, FL, 33884
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
New Solivita 258 SAND PIPER DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$423,500

3 beds

|

3 baths

|

2,314 sq ft

|

House

258 SAND PIPER DR, POINCIANA, FL, 34759
Community: Solivita
Ocala Preserve 3396 NW 55TH CT, OCALA, FL, 34482, Ocala, FL 34482
$425,000

2 beds

|

3 baths

|

2,535 sq ft

|

House

3396 NW 55TH CT, OCALA, FL, 34482
Community: Ocala Preserve
The Villages® 7574 SE 170TH LONGVIEW LN, THE VILLAGES,..., The Villages, FL 32162
$275,000

2 beds

|

2 baths

|

1,186 sq ft

|

House

7574 SE 170TH LONGVIEW LN, THE VILLAGES,...
Community: The Villages®
Lakeside Landings 10161 MAINSAIL DR, OXFORD, FL, 34484, Oxford, FL 34484
$319,000

3 beds

|

2 baths

|

1,550 sq ft

|

Villa

10161 MAINSAIL DR, OXFORD, FL, 34484
Community: Lakeside Landings
Valencia Lakes 5103 SHADY STONE PL, WIMAUMA, FL, 33598, Wimauma, FL 33598
$459,900

3 beds

|

2 baths

|

2,001 sq ft

|

House

5103 SHADY STONE PL, WIMAUMA, FL, 33598
Community: Valencia Lakes
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.
New Pine Run Estates 9927 SW 100TH TERRACE RD, OCALA, FL, 344..., Ocala, FL 34481
$249,900

2 beds

|

2 baths

|

1,344 sq ft

|

House

9927 SW 100TH TERRACE RD, OCALA, FL, 344...
Community: Pine Run Estates
Del Webb Sunbridge 6514 BARNSTORM WAY, SAINT CLOUD, FL, 347..., Saint Cloud, FL 34771
$539,900

3 beds

|

2 baths

|

1,881 sq ft

|

House

6514 BARNSTORM WAY, SAINT CLOUD, FL, 347...
Community: Del Webb Sunbridge
Heritage Hills 3524 LITCHFIELD CT, CLERMONT, FL, 34711, Clermont, FL 34711
$510,000

4 beds

|

3 baths

|

2,293 sq ft

|

House

3524 LITCHFIELD CT, CLERMONT, FL, 34711
Community: Heritage Hills
Ocala Preserve 3554 NW 55TH CIR, OCALA, FL, 34482, Ocala, FL 34482
$310,000

2 beds

|

2 baths

|

1,666 sq ft

|

House

3554 NW 55TH CIR, OCALA, FL, 34482
Community: Ocala Preserve
The Villages® 516 LOMA PASEO DR, THE VILLAGES, FL, 321..., The Villages, FL 32159
$429,000

3 beds

|

2 baths

|

1,642 sq ft

|

House

516 LOMA PASEO DR, THE VILLAGES, FL, 321...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Solivita 316 TREVISO DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$519,000

3 beds

|

3 baths

|

2,320 sq ft

|

House

316 TREVISO DR, KISSIMMEE, FL, 34759
Community: Solivita
The Villages® 3326 ROANOKE ST, THE VILLAGES, FL, 32162, The Villages, FL 32162
$244,999

2 beds

|

2 baths

|

1,204 sq ft

|

House

3326 ROANOKE ST, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 3377 QUAIL HOLLOW CT, THE VILLAGES, FL, ..., The Villages, FL 32163
$349,900

3 beds

|

2 baths

|

1,488 sq ft

|

House

3377 QUAIL HOLLOW CT, THE VILLAGES, FL, ...
Community: The Villages®
The Villages® 1204 FLAMINGO PL, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$579,000

3 beds

|

2 baths

|

1,433 sq ft

|

House

1204 FLAMINGO PL, THE VILLAGES, FL, 3216...
Community: The Villages®
New The Villages® 511 LOMA PASEO DR, THE VILLAGES, FL, 321..., The Villages, FL 32159
$385,000

2 beds

|

2 baths

|

1,832 sq ft

|

House

511 LOMA PASEO DR, THE VILLAGES, FL, 321...
Community: The Villages®

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108 communities near Winter Garden
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