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

3,648 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
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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 - $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
$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
Cresswind at Victoria Gardens 600 GARDEN CLUB DR, DELAND, FL, 32724, Deland, FL 32724
$579,000

4 beds

|

3 baths

|

2,569 sq ft

|

House

600 GARDEN CLUB DR, DELAND, FL, 32724
Esplanade at Highland Ranch 2602 STARGRASS CIR, CLERMONT, FL, 34715, Clermont, FL 34715
$394,000

2 beds

|

2 baths

|

1,732 sq ft

|

House

2602 STARGRASS CIR, CLERMONT, FL, 34715
Trilogy® Orlando 103 CRESCENT MOON DR, GROVELAND, FL, 347..., Groveland, FL 34736
$334,000

3 beds

|

2 baths

|

1,671 sq ft

|

House

103 CRESCENT MOON DR, GROVELAND, FL, 347...
Community: Trilogy® Orlando
Southshore Bay 16805 BANNER SHELL PL, WIMAUMA, FL, 3359..., Wimauma, FL 33598
$600,000

3 beds

|

3 baths

|

2,651 sq ft

|

House

16805 BANNER SHELL PL, WIMAUMA, FL, 3359...
Community: Southshore Bay
The Villages® 1639 CAMPOS DR, THE VILLAGES, FL, 32162, The Villages, FL 32162
$279,000

2 beds

|

2 baths

|

1,121 sq ft

|

Villa

1639 CAMPOS DR, 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
On Top of the World 9729 SW 99TH AVE, OCALA, FL, 34481, Ocala, FL 34481
$198,900

2 beds

|

2 baths

|

1,416 sq ft

|

House

9729 SW 99TH AVE, OCALA, FL, 34481
Community: On Top of the World
Trilogy® Orlando 119 CRESCENT MOON DR, GROVELAND, FL, 347..., Groveland, FL 34736
$349,900

2 beds

|

2 baths

|

1,556 sq ft

|

House

119 CRESCENT MOON DR, GROVELAND, FL, 347...
Community: Trilogy® Orlando
Spruce Creek Country Club 9290 SE 120TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$410,000

3 beds

|

2 baths

|

2,126 sq ft

|

House

9290 SE 120TH LOOP, SUMMERFIELD, FL, 344...
Latitude Margaritaville 309 GYPSY PALACE LN, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$399,000

2 beds

|

2 baths

|

1,205 sq ft

|

Villa

309 GYPSY PALACE LN, DAYTONA BEACH, FL, ...
Liberty Village 7828 SW 74TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$364,900

3 beds

|

3 baths

|

2,039 sq ft

|

House

7828 SW 74TH LOOP, OCALA, FL, 34481
Community: Liberty Village
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.
Trilogy® Orlando 440 ALCOVE DR, GROVELAND, FL, 34736, Groveland, FL 34736
$382,000

3 beds

|

2 baths

|

1,704 sq ft

|

House

440 ALCOVE DR, GROVELAND, FL, 34736
Community: Trilogy® Orlando
On Top of the World 8896 SW 90TH ST B, OCALA, FL, 34481, Ocala, FL 34481
$169,000

2 beds

|

2 baths

|

1,377 sq ft

|

Villa

8896 SW 90TH ST B, OCALA, FL, 34481
Community: On Top of the World
The Villages® 1613 NAVIDAD ST, THE VILLAGES, FL, 32162, The Villages, FL 32162
$285,000

2 beds

|

2 baths

|

1,121 sq ft

|

Villa

1613 NAVIDAD ST, THE VILLAGES, FL, 32162
Community: The Villages®
On Top of the World 9272 SW 82ND TER D, OCALA, FL, 34481, Ocala, FL 34481
$167,000

2 beds

|

2 baths

|

1,249 sq ft

|

Villa

9272 SW 82ND TER D, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 9490 SW 94TH CT, OCALA, FL, 34481, Ocala, FL 34481
$215,000

2 beds

|

2 baths

|

1,504 sq ft

|

House

9490 SW 94TH CT, OCALA, FL, 34481
Community: On Top of the World
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Venetian Bay 461 LUNA BELLA LN, NEW SMYRNA BEACH, FL,..., New Smyrna Beach, FL 32168
$625,000

3 beds

|

2 baths

|

2,002 sq ft

|

House

461 LUNA BELLA LN, NEW SMYRNA BEACH, FL,...
Community: Venetian Bay
Spruce Creek Country Club 13751 SE 88TH CT, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$265,000

2 beds

|

2 baths

|

1,364 sq ft

|

House

13751 SE 88TH CT, SUMMERFIELD, FL, 34491
Stonecrest 17645 SE 117TH CIR, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$317,500

3 beds

|

3 baths

|

1,686 sq ft

|

House

17645 SE 117TH CIR, SUMMERFIELD, FL, 344...
Community: Stonecrest
Solivita 2285 PALM TREE DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$334,900

2 beds

|

2 baths

|

1,703 sq ft

|

House

2285 PALM TREE DR, KISSIMMEE, FL, 34759
Community: Solivita
Lakeside Landings 10063 LAKE MIONA WAY, OXFORD, FL, 34484, Oxford, FL 34484
$449,800

3 beds

|

2 baths

|

2,066 sq ft

|

House

10063 LAKE MIONA WAY, OXFORD, FL, 34484
Community: Lakeside Landings
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.
VillageWalk at Lake Nona 11999 MODENA LN, ORLANDO, FL, 32827, Orlando, FL 32827
$450,000

3 beds

|

2 baths

|

1,554 sq ft

|

Villa

11999 MODENA LN, ORLANDO, FL, 32827
On Top of the World 7750 SW 87TH AVE, OCALA, FL, 34481, Ocala, FL 34481
$419,000

3 beds

|

2 baths

|

2,118 sq ft

|

House

7750 SW 87TH AVE, OCALA, FL, 34481
Community: On Top of the World
Stone Creek 6119 SW 93RD CIR, OCALA, FL, 34481, Ocala, FL 34481
$300,000

3 beds

|

2 baths

|

1,656 sq ft

|

House

6119 SW 93RD CIR, OCALA, FL, 34481
Community: Stone Creek
Royal Highlands 5401 ESSEX CT, LEESBURG, FL, 34748, Leesburg, FL 34748
$389,000

2 beds

|

3 baths

|

2,009 sq ft

|

House

5401 ESSEX CT, LEESBURG, FL, 34748
Community: Royal Highlands
Sandpiper Golf & Country Club 6096 KITTIWAKE DR, LAKELAND, FL, 33809, Lakeland, FL 33809
$315,000

3 beds

|

2 baths

|

1,489 sq ft

|

House

6096 KITTIWAKE DR, LAKELAND, FL, 33809
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Valencia del Sol 4906 AVILA LAKES DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$299,500

2 beds

|

2 baths

|

1,646 sq ft

|

Villa

4906 AVILA LAKES DR, WIMAUMA, FL, 33598
Community: Valencia del Sol
Sandpiper Golf & Country Club 6256 SANDPIPERS DR, LAKELAND, FL, 33809, Lakeland, FL 33809
$298,500

2 beds

|

2 baths

|

1,627 sq ft

|

House

6256 SANDPIPERS DR, LAKELAND, FL, 33809
Four Seasons at Orlando 1890 FLORA PASS PL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$319,000

2 beds

|

2 baths

|

1,557 sq ft

|

Villa

1890 FLORA PASS PL, KISSIMMEE, FL, 34747
The Villages® 491 HARLOW LN, THE VILLAGES, FL, 32163, The Villages, FL 32163
$549,000

3 beds

|

2 baths

|

1,958 sq ft

|

House

491 HARLOW LN, THE VILLAGES, FL, 32163
Community: The Villages®
Solivita 573 DAVINCI PASS, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$285,000

2 beds

|

2 baths

|

1,340 sq ft

|

House

573 DAVINCI PASS, 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.
Stone Creek 9582 SW 70TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$244,599

2 beds

|

2 baths

|

1,696 sq ft

|

Villa

9582 SW 70TH LOOP, OCALA, FL, 34481
Community: Stone Creek
Stone Creek 9470 SW 52ND LOOP, OCALA, FL, 34481, Ocala, FL 34481
$328,888

3 beds

|

2 baths

|

1,662 sq ft

|

House

9470 SW 52ND LOOP, OCALA, FL, 34481
Community: Stone Creek
Traditions at Lake Ruby 2925 DAYTON DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$314,900

3 beds

|

2 baths

|

2,109 sq ft

|

House

2925 DAYTON DR, WINTER HAVEN, FL, 33884
The Lakes at Harmony 7529 CASTLEWOOD CT, HARMONY, FL, 34773, Harmony, FL 34773
$395,000

3 beds

|

2 baths

|

1,852 sq ft

|

House

7529 CASTLEWOOD CT, HARMONY, FL, 34773
VillageWalk at Lake Nona 12202 PASHA LN, ORLANDO, FL, 32827, Orlando, FL 32827
$649,000

3 beds

|

2 baths

|

2,221 sq ft

|

House

12202 PASHA LN, ORLANDO, FL, 32827
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Pelican Bay Daytona Beach 129 GOLDEN EYE DR C, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119
$234,000

2 beds

|

2 baths

|

1,242 sq ft

|

Condo

129 GOLDEN EYE DR C, DAYTONA BEACH, FL, ...
Ocala Preserve 5297 NW 34TH ST, OCALA, FL, 34482, Ocala, FL 34482
$265,000

2 beds

|

2 baths

|

1,318 sq ft

|

Villa

5297 NW 34TH ST, OCALA, FL, 34482
Community: Ocala Preserve
Ocala Preserve 5086 NW 35TH PL, OCALA, FL, 34482, Ocala, FL 34482
$429,999

3 beds

|

3 baths

|

2,065 sq ft

|

House

5086 NW 35TH PL, OCALA, FL, 34482
Community: Ocala Preserve
Solivita 582 SAN JOAQUIN RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$385,000

3 beds

|

2 baths

|

1,730 sq ft

|

House

582 SAN JOAQUIN RD, KISSIMMEE, FL, 34759
Community: Solivita
Sun City Center 1306 SPRY CT # 1306, SUN CITY CENTER, FL..., Sun City Center, FL 33573
$175,000

2 beds

|

2 baths

|

1,219 sq ft

|

Condo

1306 SPRY CT # 1306, SUN CITY CENTER, FL...
Community: Sun City Center

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3,648 homes near Winter Garden
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