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

3,573 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 - $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
Want to learn more about 55+ communities in Winter Garden? 55places can help!
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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 - $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 - $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 - $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
$200Ks - $200Ks
Cypress Lakes, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1987 - 2016 | 1,604 homes
5 rating (3 reviews) Lake Ashton
$200Ks - $500Ks
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 - $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 - $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 - $400Ks
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
Tarawood 10541 S DREW BRYANT CIR, FLORAL CITY, FL..., Floral City, FL 34436
$279,000

3 beds

|

2 baths

|

1,260 sq ft

|

House

10541 S DREW BRYANT CIR, FLORAL CITY, FL...
Community: Tarawood
Royal Highlands 21523 QUEEN ANNE CT, LEESBURG, FL, 34748, Leesburg, FL 34748
$269,000

3 beds

|

2 baths

|

1,671 sq ft

|

House

21523 QUEEN ANNE CT, LEESBURG, FL, 34748
Community: Royal Highlands
Del Webb Sunbridge 2479 PINE PRESERVE CT, SAINT CLOUD, FL, ..., Saint Cloud, FL 34771
$580,000

3 beds

|

2 baths

|

2,056 sq ft

|

House

2479 PINE PRESERVE CT, SAINT CLOUD, FL, ...
Community: Del Webb Sunbridge
Southshore Bay 17140 HOLLY WELL AVE, WIMAUMA, FL, 33598, Wimauma, FL 33598
$339,900

2 beds

|

2 baths

|

1,761 sq ft

|

House

17140 HOLLY WELL AVE, WIMAUMA, FL, 33598
Community: Southshore Bay
Southshore Bay 16938 SCUBA CREST ST, WIMAUMA, FL, 33598, Wimauma, FL 33598
$649,999

3 beds

|

4 baths

|

2,778 sq ft

|

House

16938 SCUBA CREST ST, WIMAUMA, FL, 33598
Community: Southshore Bay
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Spruce Creek Country Club 13495 SE 93RD COURT RD, SUMMERFIELD, FL,..., Summerfield, FL 34491
$385,000

3 beds

|

3 baths

|

2,110 sq ft

|

House

13495 SE 93RD COURT RD, SUMMERFIELD, FL,...
Southshore Bay 5329 WINDY GROVE DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$614,000

3 beds

|

3 baths

|

2,776 sq ft

|

House

5329 WINDY GROVE DR, WIMAUMA, FL, 33598
Community: Southshore Bay
Southshore Bay 16927 APRIL PLUSH DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$300,000

2 beds

|

2 baths

|

1,416 sq ft

|

Villa

16927 APRIL PLUSH DR, WIMAUMA, FL, 33598
Community: Southshore Bay
Southshore Bay 16868 SCUBA CREST ST, WIMAUMA, FL, 33598, Wimauma, FL 33598
$349,900

2 beds

|

2 baths

|

1,683 sq ft

|

House

16868 SCUBA CREST ST, WIMAUMA, FL, 33598
Community: Southshore Bay
Southshore Bay 17523 HOLLY WELL AVE, WIMAUMA, FL, 33598, Wimauma, FL 33598
$310,000

2 beds

|

2 baths

|

1,406 sq ft

|

Townhouse

17523 HOLLY WELL AVE, WIMAUMA, FL, 33598
Community: Southshore Bay
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.
Southshore Bay 16847 WHISPER ELM ST, WIMAUMA, FL, 33598, Wimauma, FL 33598
$300,000

2 beds

|

3 baths

|

1,737 sq ft

|

Villa

16847 WHISPER ELM ST, WIMAUMA, FL, 33598
Community: Southshore Bay
The Villages® 1605 CHAVEZ CT, THE VILLAGES, FL, 32159, The Villages, FL 32159
$395,000

2 beds

|

2 baths

|

1,638 sq ft

|

House

1605 CHAVEZ CT, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 3118 SWEETGUM ST, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$345,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

3118 SWEETGUM ST, THE VILLAGES, FL, 3216...
Community: The Villages®
Highland Fairways 2206 GOLDEN HORSESHOE CIR, LAKELAND, FL,..., Lakeland, FL 33810
$199,000

2 beds

|

2 baths

|

1,274 sq ft

|

Manufactured Home

2206 GOLDEN HORSESHOE CIR, LAKELAND, FL,...
Community: Highland Fairways
Stonecrest 11094 SE 173RD LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$290,000

3 beds

|

2 baths

|

1,717 sq ft

|

House

11094 SE 173RD LN, SUMMERFIELD, FL, 3449...
Community: Stonecrest
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
On Top of the World 8420 SW 93RD LN E, OCALA, FL, 34481, Ocala, FL 34481
$165,500

2 beds

|

2 baths

|

1,223 sq ft

|

Villa

8420 SW 93RD LN E, OCALA, FL, 34481
Community: On Top of the World
The Villages® 3540 OBRIEN PL, THE VILLAGES, FL, 32163, The Villages, FL 32163
$549,900

3 beds

|

3 baths

|

2,563 sq ft

|

House

3540 OBRIEN PL, THE VILLAGES, FL, 32163
Community: The Villages®
Del Webb Orlando 503 VIGO ST, DAVENPORT, FL, 33837, Davenport, FL 33837
$325,000

2 beds

|

2 baths

|

1,468 sq ft

|

House

503 VIGO ST, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Spruce Creek South 17913 SE 95TH CT, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$230,000

3 beds

|

2 baths

|

1,450 sq ft

|

House

17913 SE 95TH CT, SUMMERFIELD, FL, 34491
Community: Spruce Creek South
Oak Run 11097 SW 69TH CIR, OCALA, FL, 34476, Ocala, FL 34476
$290,000

3 beds

|

2 baths

|

1,677 sq ft

|

House

11097 SW 69TH CIR, OCALA, FL, 34476
Community: Oak Run
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 313 SANTA BARBARA LN, KISSIMMEE, FL, 347..., Kissimmee, FL 34759
$473,900

2 beds

|

3 baths

|

2,343 sq ft

|

House

313 SANTA BARBARA LN, KISSIMMEE, FL, 347...
Community: Solivita
Sun City Center 721 MASTERPIECE DR # 141, SUN CITY CENTE..., Sun City Center, FL 33573
$284,900

2 beds

|

2 baths

|

1,444 sq ft

|

Condo

721 MASTERPIECE DR # 141, SUN CITY CENTE...
Community: Sun City Center
Solivita 753 LARGO PASS, POINCIANA, FL, 34759, Poinciana, FL 34759
$254,900

2 beds

|

2 baths

|

1,467 sq ft

|

House

753 LARGO PASS, POINCIANA, FL, 34759
Community: Solivita
Stone Creek 7150 SW 91ST CT, OCALA, FL, 34481, Ocala, FL 34481
$249,500

2 beds

|

2 baths

|

1,556 sq ft

|

Villa

7150 SW 91ST CT, OCALA, FL, 34481
Community: Stone Creek
Scottish Highlands 28 GORDON CT, LEESBURG, FL, 34788, Leesburg, FL 34788
$207,000

2 beds

|

2 baths

|

1,374 sq ft

|

House

28 GORDON CT, LEESBURG, FL, 34788
Community: Scottish Highlands
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Arlington Ridge 3677 ARLINGTON RIDGE BLVD, LEESBURG, FL,..., Leesburg, FL 34748
$500,000

3 beds

|

2 baths

|

2,201 sq ft

|

House

3677 ARLINGTON RIDGE BLVD, LEESBURG, FL,...
Community: Arlington Ridge
Cresswind at Victoria Gardens 1069 AVERY MEADOWS WAY, DELAND, FL, 3272..., Deland, FL 32724
$397,000

2 beds

|

2 baths

|

1,651 sq ft

|

House

1069 AVERY MEADOWS WAY, DELAND, FL, 3272...
Pelican Bay Daytona Beach 133 BLUE HERON DR D, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119
$189,500

2 beds

|

2 baths

|

1,242 sq ft

|

Condo

133 BLUE HERON DR D, DAYTONA BEACH, FL, ...
Sun City Center 2630 LANCASTER DR, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$155,000

2 beds

|

2 baths

|

1,529 sq ft

|

Condo

2630 LANCASTER DR, SUN CITY CENTER, FL, ...
Community: Sun City Center
Heritage - The Cottages of Sanders Grove 28026 CYPRESS SPRINGS LOOP, OKAHUMPKA, F..., Okahumpka, FL 34762
$292,899

3 beds

|

2 baths

|

1,617 sq ft

|

House

28026 CYPRESS SPRINGS LOOP, OKAHUMPKA, F...
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.
Venetian Bay 461 LUNA BELLA LN, NEW SMYRNA BEACH, FL,..., New Smyrna Beach, FL 32168
$649,500

3 beds

|

2 baths

|

2,002 sq ft

|

House

461 LUNA BELLA LN, NEW SMYRNA BEACH, FL,...
Community: Venetian Bay
Pelican Bay Daytona Beach 244 PALM SPARROW CT, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119
$325,000

2 beds

|

2 baths

|

1,370 sq ft

|

House

244 PALM SPARROW CT, DAYTONA BEACH, FL, ...
The Villages® 1654 BLOSSOM TER, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$320,000

3 beds

|

2 baths

|

1,240 sq ft

|

House

1654 BLOSSOM TER, THE VILLAGES, FL, 3216...
Community: The Villages®
Sun City Center 2208 GRENADIER DR, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$109,000

2 beds

|

2 baths

|

984 sq ft

|

Condo

2208 GRENADIER DR, SUN CITY CENTER, FL, ...
Community: Sun City Center
The Villages® 278 MATISSE AVE, THE VILLAGES, FL, 32162, The Villages, FL 32162
$494,900

3 beds

|

2 baths

|

1,966 sq ft

|

House

278 MATISSE AVE, THE VILLAGES, FL, 32162
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 1523 W SCHWARTZ BLVD, THE VILLAGES, FL, ..., The Villages, FL 32159
$199,900

2 beds

|

2 baths

|

1,040 sq ft

|

Manufactured Home

1523 W SCHWARTZ BLVD, THE VILLAGES, FL, ...
Community: The Villages®
Spruce Creek South 17813 SE 95TH CT, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$249,900

2 beds

|

2 baths

|

1,158 sq ft

|

House

17813 SE 95TH CT, SUMMERFIELD, FL, 34491
Community: Spruce Creek South
Oak Run 7709 SW 86TH CT, OCALA, FL, 34481, Ocala, FL 34481
$345,900

2 beds

|

2 baths

|

1,747 sq ft

|

House

7709 SW 86TH CT, OCALA, FL, 34481
Community: Oak Run
On Top of the World 8423 SW 82ND CIR, OCALA, FL, 34481, Ocala, FL 34481
$349,000

3 beds

|

2 baths

|

2,283 sq ft

|

House

8423 SW 82ND CIR, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 7706 SW 89TH CT, OCALA, FL, 34481, Ocala, FL 34481
$329,000

2 beds

|

2 baths

|

1,747 sq ft

|

House

7706 SW 89TH CT, OCALA, FL, 34481
Community: On Top of the World

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3,573 homes near Winter Garden
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