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

106 communities near Winter Garden

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No reviews yet 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 - $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
$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 - $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
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3.6 rating (46 reviews) Latitude Margaritaville
$300Ks - $800Ks
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 - $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
$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
$100Ks - $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 - $600Ks
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
$300Ks - $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 - $500Ks
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 - $900Ks
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...
$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 - $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
$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
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
The Villages® 2217 ISLEWORTH CIR, THE VILLAGES, FL, 32..., The Villages, FL 32163
$1,075,000

3 beds

|

2 baths

|

2,683 sq ft

|

House

2217 ISLEWORTH CIR, THE VILLAGES, FL, 32...
Community: The Villages®
The Villages® 906 TRIFU TER, THE VILLAGES, FL, 32163, The Villages, FL 32163
$410,000

3 beds

|

2 baths

|

1,694 sq ft

|

House

906 TRIFU TER, THE VILLAGES, FL, 32163
Community: The Villages®
New Marion Landing 8478 SW 61ST TERRACE RD, OCALA, FL, 3447..., Ocala, FL 34476
$220,000

2 beds

|

2 baths

|

1,420 sq ft

|

House

8478 SW 61ST TERRACE RD, OCALA, FL, 3447...
Community: Marion Landing
New Vienna Square 1584 VIENNA SQUARE DR, WINTER HAVEN, FL,..., Winter Haven, FL 33884
$225,000

2 beds

|

2 baths

|

1,231 sq ft

|

Villa

1584 VIENNA SQUARE DR, WINTER HAVEN, FL,...
Community: Vienna Square
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
New Ocala Palms 5185 NW 21ST LOOP, OCALA, FL, 34482, Ocala, FL 34482
$415,000

3 beds

|

2 baths

|

2,166 sq ft

|

House

5185 NW 21ST LOOP, OCALA, FL, 34482
Community: Ocala Palms
New The Villages® 17966 SE 89TH NATCHEZ AVE, THE VILLAGES,..., The Villages, FL 32162
$345,000

3 beds

|

2 baths

|

1,488 sq ft

|

House

17966 SE 89TH NATCHEZ AVE, THE VILLAGES,...
Community: The Villages®
Pelican Bay Daytona Beach 105 MARBLED GODWIT CT, DAYTONA BEACH, FL..., Daytona Beach, FL 32119
$450,000

3 beds

|

2 baths

|

2,568 sq ft

|

House

105 MARBLED GODWIT CT, DAYTONA BEACH, FL...
New On Top of the World 9451 SW 96TH ST, OCALA, FL, 34481, Ocala, FL 34481
$242,000

2 beds

|

2 baths

|

1,744 sq ft

|

Halfplex

9451 SW 96TH ST, OCALA, FL, 34481
Community: On Top of the World
Solivita 384 GRAND CANAL DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$269,950

2 beds

|

2 baths

|

1,512 sq ft

|

House

384 GRAND CANAL DR, POINCIANA, 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.
Solivita 972 LADERA RANCH RD, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759
$489,900

3 beds

|

3 baths

|

2,318 sq ft

|

House

972 LADERA RANCH RD, KISSIMMEE, FL, 3475...
Community: Solivita
Lake Ashton 4568 BACK NINE DR, WINTER HAVEN, FL, 338..., Winter Haven, FL 33884
$349,900

3 beds

|

2 baths

|

2,043 sq ft

|

House

4568 BACK NINE DR, WINTER HAVEN, FL, 338...
Community: Lake Ashton
Spruce Creek South 17728 SE 97TH AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$229,000

2 beds

|

2 baths

|

1,390 sq ft

|

House

17728 SE 97TH AVE, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
The Villages® 950 LADSON LOOP, THE VILLAGES, FL, 32162, The Villages, FL 32162
$395,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

950 LADSON LOOP, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 1705 BETRILLO CT, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$259,900

3 beds

|

2 baths

|

1,210 sq ft

|

House

1705 BETRILLO CT, 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
Stonecrest 11584 SE 175TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$329,000

2 beds

|

2 baths

|

1,702 sq ft

|

House

11584 SE 175TH ST, SUMMERFIELD, FL, 3449...
Community: Stonecrest
Legacy of Leesburg 5809 CELEBRATION WAY, LEESBURG, FL, 3474..., Leesburg, FL 34748
$249,000

3 beds

|

2 baths

|

1,477 sq ft

|

House

5809 CELEBRATION WAY, LEESBURG, FL, 3474...
Community: Legacy of Leesburg
Spruce Creek South 15823 SE 101ST CIR, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$295,990

4 beds

|

2 baths

|

1,828 sq ft

|

House

15823 SE 101ST CIR, SUMMERFIELD, FL, 344...
Community: Spruce Creek South
Del Webb Oasis 16235 HONEY HARVEST ST, WINTER GARDEN, F..., Winter Garden, FL 34787
$800,000

5 beds

|

4 baths

|

2,670 sq ft

|

House

16235 HONEY HARVEST ST, WINTER GARDEN, F...
Community: Del Webb Oasis
Del Webb Oasis 13069 SUNRISE HARVEST DR, WINTER GARDEN,..., Winter Garden, FL 34787
$725,000

4 beds

|

3 baths

|

2,120 sq ft

|

House

13069 SUNRISE HARVEST DR, WINTER GARDEN,...
Community: Del Webb Oasis
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.
Del Webb Oasis 13533 PEARL BEACH ST, WINTER GARDEN, FL,..., Winter Garden, FL 34787
$427,560

2 beds

|

2 baths

|

1,579 sq ft

|

Villa

13533 PEARL BEACH ST, WINTER GARDEN, FL,...
Community: Del Webb Oasis
Del Webb Oasis 13536 AUTUMN HARVEST AVE, WINTER GARDEN,..., Winter Garden, FL 34787
$470,000

3 beds

|

3 baths

|

1,785 sq ft

|

Townhouse

13536 AUTUMN HARVEST AVE, WINTER GARDEN,...
Community: Del Webb Oasis
Del Webb Oasis 15569 ORCHID ROSE CT, WINTER GARDEN, FL,..., Winter Garden, FL 34787
$949,000

4 beds

|

4 baths

|

3,489 sq ft

|

House

15569 ORCHID ROSE CT, WINTER GARDEN, FL,...
Community: Del Webb Oasis
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
Del Webb Oasis 13532 AUTUMN HARVEST AVE, WINTER GARDEN,..., Winter Garden, FL 34787
$470,000

3 beds

|

3 baths

|

1,785 sq ft

|

Townhouse

13532 AUTUMN HARVEST AVE, WINTER GARDEN,...
Community: Del Webb Oasis
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Del Webb Oasis 13528 AUTUMN HARVEST AVE, WINTER GARDEN,..., Winter Garden, FL 34787
$490,000

3 beds

|

3 baths

|

1,955 sq ft

|

Townhouse

13528 AUTUMN HARVEST AVE, WINTER GARDEN,...
Community: Del Webb Oasis
Del Webb Oasis 13809 LUNA HARVEST AVE, WINTER GARDEN, F..., Winter Garden, FL 34787
$440,000

3 beds

|

3 baths

|

1,785 sq ft

|

Townhouse

13809 LUNA HARVEST AVE, WINTER GARDEN, F...
Community: Del Webb Oasis
Del Webb Oasis 13563 PEARL BEACH ST, WINTER GARDEN, FL,..., Winter Garden, FL 34787
$430,000

2 beds

|

2 baths

|

1,579 sq ft

|

House

13563 PEARL BEACH ST, WINTER GARDEN, FL,...
Community: Del Webb Oasis
On Top of the World 6620 SW 81ST LOOP, OCALA, FL, 34476, Ocala, FL 34476
$237,990

3 beds

|

3 baths

|

1,458 sq ft

|

Townhouse

6620 SW 81ST LOOP, OCALA, FL, 34476
Community: On Top of the World
Ocala Preserve 4067 NW 44TH CIR, OCALA, FL, 34482, Ocala, FL 34482
$242,990

3 beds

|

2 baths

|

1,504 sq ft

|

House

4067 NW 44TH CIR, OCALA, FL, 34482
Community: Ocala Preserve
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.
Liberty Village 7828 SW 74TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$375,000

3 beds

|

3 baths

|

2,039 sq ft

|

House

7828 SW 74TH LOOP, OCALA, FL, 34481
Community: Liberty Village
The Villages® 1705 STAUNTON ST, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$335,000

3 beds

|

2 baths

|

1,527 sq ft

|

House

1705 STAUNTON ST, THE VILLAGES, FL, 3216...
Community: The Villages®
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 508 VILLAGIO LOOP, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$339,000

3 beds

|

2 baths

|

1,817 sq ft

|

House

508 VILLAGIO LOOP, KISSIMMEE, FL, 34759
Community: Solivita
Lake Ashton 4433 VENTANA LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$489,900

3 beds

|

2 baths

|

2,512 sq ft

|

House

4433 VENTANA LN, LAKE WALES, FL, 33859
Community: Lake Ashton
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Solivita 482 DAVINCI PASS, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$319,000

3 beds

|

2 baths

|

1,786 sq ft

|

House

482 DAVINCI PASS, KISSIMMEE, FL, 34759
Community: Solivita
Oak Run 8443 SW 109TH PL, OCALA, FL, 34481, Ocala, FL 34481
$173,000

2 beds

|

2 baths

|

1,100 sq ft

|

House

8443 SW 109TH PL, OCALA, FL, 34481
Community: Oak Run
New The Villages® 3301 BERKELEY LN, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$415,000

3 beds

|

2 baths

|

1,920 sq ft

|

House

3301 BERKELEY LN, THE VILLAGES, FL, 3216...
Community: The Villages®
Solivita 3775 VIA MAZZINI CT, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759
$524,900

4 beds

|

3 baths

|

2,495 sq ft

|

House

3775 VIA MAZZINI CT, KISSIMMEE, FL, 3475...
Community: Solivita
Solivita 804 SAN RAPHAEL ST, POINCIANA, FL, 34759, Poinciana, FL 34759
$522,500

3 beds

|

4 baths

|

2,782 sq ft

|

House

804 SAN RAPHAEL ST, POINCIANA, FL, 34759
Community: Solivita

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106 communities near Winter Garden
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