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

3,584 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
<$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
$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!
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 - $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.
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) Trilogy® Orlando
$300Ks - $600Ks
Trilogy® Orlando, Groveland, FL
Resale Only | 55+ age-restricted | Built 2005 - 2022 | 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 - $900Ks
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...
$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
Stonecrest 11010 SE 174TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491
$350,000

3 beds

|

2 baths

|

1,793 sq ft

|

House

11010 SE 174TH LOOP, SUMMERFIELD, FL, 34...
Community: Stonecrest
Encore at Fishhawk Ranch 6230 PLOVER MEADOW ST, LITHIA, FL, 33547, Lithia, FL 33547
$505,000

2 beds

|

2 baths

|

1,768 sq ft

|

House

6230 PLOVER MEADOW ST, LITHIA, FL, 33547
Heritage Hills 3674 CALADESI RD, CLERMONT, FL, 34711, Clermont, FL 34711
$400,000

3 beds

|

2 baths

|

1,672 sq ft

|

House

3674 CALADESI RD, CLERMONT, FL, 34711
Community: Heritage Hills
Solivita 1423 HARBOR RIDGE DR, POINCIANA, FL, 347..., Poinciana, FL 34759
$315,000

2 beds

|

2 baths

|

1,703 sq ft

|

House

1423 HARBOR RIDGE DR, POINCIANA, FL, 347...
Community: Solivita
Pelican Bay Daytona Beach 105 MARBLED GODWIT CT, DAYTONA BEACH, FL..., Daytona Beach, FL 32119
$465,000

3 beds

|

2 baths

|

2,568 sq ft

|

House

105 MARBLED GODWIT CT, DAYTONA BEACH, FL...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 1001 GREYFORD LN, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$334,900

2 beds

|

2 baths

|

1,351 sq ft

|

Villa

1001 GREYFORD LN, THE VILLAGES, FL, 3216...
Community: The Villages®
Lakeside Landings 10105 KETCH KAY LN, OXFORD, FL, 34484, Oxford, FL 34484
$319,900

3 beds

|

2 baths

|

1,856 sq ft

|

House

10105 KETCH KAY LN, OXFORD, FL, 34484
Community: Lakeside Landings
Lake Jovita Golf and Country Club 34411 SAHALEE LOOP, DADE CITY, FL, 33525, Dade City, FL 33525
$775,000

3 beds

|

3 baths

|

2,777 sq ft

|

House

34411 SAHALEE LOOP, DADE CITY, FL, 33525
On Top of the World 8640 SW 83RD LOOP, OCALA, FL, 34481, Ocala, FL 34481
$305,000

3 beds

|

2 baths

|

1,906 sq ft

|

House

8640 SW 83RD LOOP, OCALA, FL, 34481
Community: On Top of the World
The Villages® 2457 UPTON ST, THE VILLAGES, FL, 32163, The Villages, FL 32163
$299,900

2 beds

|

2 baths

|

1,156 sq ft

|

House

2457 UPTON ST, THE VILLAGES, FL, 32163
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.
The Villages® 947 COUTURE ST, THE VILLAGES, FL, 32163, The Villages, FL 32163
$459,900

3 beds

|

2 baths

|

1,484 sq ft

|

Villa

947 COUTURE ST, THE VILLAGES, FL, 32163
Community: The Villages®
Oak Run 10897 SW 80TH CT, OCALA, FL, 34481, Ocala, FL 34481
$199,000

2 beds

|

2 baths

|

1,224 sq ft

|

House

10897 SW 80TH CT, OCALA, FL, 34481
Community: Oak Run
The Villages® 2102 ESTEVEZ DR, THE VILLAGES, FL, 32159, The Villages, FL 32159
$275,000

2 beds

|

2 baths

|

1,121 sq ft

|

Villa

2102 ESTEVEZ DR, THE VILLAGES, FL, 32159
Community: The Villages®
Sun City Center 1601 WOODMAR DR, SUN CITY CENTER, FL, 33..., Sun City Center, FL 33573
$250,000

2 beds

|

2 baths

|

1,857 sq ft

|

House

1601 WOODMAR DR, SUN CITY CENTER, FL, 33...
Community: Sun City Center
Valencia Lakes 5009 SANDY BROOK CIR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$385,000

3 beds

|

2 baths

|

1,864 sq ft

|

House

5009 SANDY BROOK CIR, WIMAUMA, FL, 33598
Community: Valencia Lakes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 3141 MANSFIELD ST, THE VILLAGES, FL, 321..., The Villages, FL 32162
$799,000

3 beds

|

2 baths

|

2,340 sq ft

|

House

3141 MANSFIELD ST, THE VILLAGES, FL, 321...
Community: The Villages®
On Top of the World 9839 SW 90TH ST, OCALA, FL, 34481, Ocala, FL 34481
$379,000

2 beds

|

2 baths

|

2,079 sq ft

|

House

9839 SW 90TH ST, OCALA, FL, 34481
Community: On Top of the World
The Villages® 415 S TIMBER TRL, WILDWOOD, FL, 34785, Wildwood, FL 34785
$119,900

2 beds

|

2 baths

|

1,144 sq ft

|

House

415 S TIMBER TRL, WILDWOOD, FL, 34785
Community: The Villages®
The Villages® 2705 LA POSADA DR, THE VILLAGES, FL, 321..., The Villages, FL 32162
$374,900

3 beds

|

2 baths

|

1,647 sq ft

|

House

2705 LA POSADA DR, THE VILLAGES, FL, 321...
Community: The Villages®
Tohoqua Reserve 1855 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744
$400,000

2 beds

|

2 baths

|

1,559 sq ft

|

House

1855 SPRING SHOWER CIR, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
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.
The Villages® 1885 OAKCREST PATH, THE VILLAGES, FL, 32..., The Villages, FL 32162
$640,000

3 beds

|

2 baths

|

1,937 sq ft

|

House

1885 OAKCREST PATH, THE VILLAGES, FL, 32...
Community: The Villages®
Valencia del Sol 15442 SANTA POLA DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$375,000

2 beds

|

2 baths

|

1,592 sq ft

|

House

15442 SANTA POLA DR, WIMAUMA, FL, 33598
Community: Valencia del Sol
Plantation at Leesburg 5300 TIGERS TAIL, LEESBURG, FL, 34748, Leesburg, FL 34748
$174,900

2 beds

|

2 baths

|

1,144 sq ft

|

Manufactured Home

5300 TIGERS TAIL, LEESBURG, FL, 34748
The Villages® 1727 HILTON HEAD BLVD, THE VILLAGES, FL,..., The Villages, FL 32159
$210,000

2 beds

|

2 baths

|

1,180 sq ft

|

Manufactured Home

1727 HILTON HEAD BLVD, THE VILLAGES, FL,...
Community: The Villages®
Vienna Square 1224 VIENNA SQUARE DR, WINTER HAVEN, FL,..., Winter Haven, FL 33884
$215,000

2 beds

|

2 baths

|

1,118 sq ft

|

Villa

1224 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
The Villages® 7243 SE 172ND LEGACY LN, THE VILLAGES, F..., The Villages, FL 32162
$453,900

3 beds

|

2 baths

|

1,918 sq ft

|

House

7243 SE 172ND LEGACY LN, THE VILLAGES, F...
Community: The Villages®
Pine Run Estates 8879 SW 104TH LN, OCALA, FL, 34481, Ocala, FL 34481
$209,000

2 beds

|

2 baths

|

1,347 sq ft

|

House

8879 SW 104TH LN, OCALA, FL, 34481
Community: Pine Run Estates
Spruce Creek North 10980 SW 62ND AVE, OCALA, FL, 34476, Ocala, FL 34476
$204,900

3 beds

|

2 baths

|

1,526 sq ft

|

House

10980 SW 62ND AVE, OCALA, FL, 34476
Community: Spruce Creek North
Highland Fairways 3618 HIGHLAND FAIRWAYS BLVD, LAKELAND, F..., Lakeland, FL 33810
$289,900

3 beds

|

2 baths

|

1,680 sq ft

|

House

3618 HIGHLAND FAIRWAYS BLVD, LAKELAND, F...
Community: Highland Fairways
SummerGlen 15692 SW 16TH TER, OCALA, FL, 34473, Ocala, FL 34473
$245,000

3 beds

|

2 baths

|

1,647 sq ft

|

House

15692 SW 16TH TER, OCALA, FL, 34473
Community: SummerGlen
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 3361 STEFANO ST, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168
$554,000

3 beds

|

3 baths

|

2,136 sq ft

|

House

3361 STEFANO ST, NEW SMYRNA BEACH, FL, 3...
Community: Venetian Bay
Pelican Bay Daytona Beach 105 WOOD DUCK CIR # 1C, DAYTONA BEACH, F..., Daytona Beach, FL 32119
$189,900

2 beds

|

2 baths

|

1,242 sq ft

|

Condo

105 WOOD DUCK CIR # 1C, DAYTONA BEACH, F...
Spruce Creek Country Club 13914 SE 96TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$379,000

3 beds

|

2 baths

|

1,958 sq ft

|

House

13914 SE 96TH CIR, SUMMERFIELD, FL, 3449...
On Top of the World 10091 SW 84TH STREET RD, OCALA, FL, 3448..., Ocala, FL 34481
$485,000

3 beds

|

3 baths

|

2,870 sq ft

|

House

10091 SW 84TH STREET RD, OCALA, FL, 3448...
Community: On Top of the World
On Top of the World 10032 SW 85TH PLACE RD, OCALA, FL, 34481, Ocala, FL 34481
$455,000

2 beds

|

2 baths

|

2,145 sq ft

|

House

10032 SW 85TH PLACE RD, 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
On Top of the World 8492 SW 99TH CIR, OCALA, FL, 34481, Ocala, FL 34481
$515,000

3 beds

|

3 baths

|

2,907 sq ft

|

House

8492 SW 99TH CIR, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 10075 SW 84TH STREET RD, OCALA, FL, 3448..., Ocala, FL 34481
$525,000

3 beds

|

3 baths

|

2,907 sq ft

|

House

10075 SW 84TH STREET RD, OCALA, FL, 3448...
Community: On Top of the World
On Top of the World 8518 SW 99TH CIR, OCALA, FL, 34481, Ocala, FL 34481
$475,000

3 beds

|

3 baths

|

2,211 sq ft

|

House

8518 SW 99TH CIR, OCALA, FL, 34481
Community: On Top of the World
Harbor Hills Country Club 5349 GROVE MNR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$445,000

4 beds

|

2 baths

|

2,056 sq ft

|

House

5349 GROVE MNR, LADY LAKE, FL, 32159
Palm Cay 10107 SW 106TH CIR, OCALA, FL, 34481, Ocala, FL 34481
$399,000

2 beds

|

2 baths

|

2,142 sq ft

|

House

10107 SW 106TH CIR, OCALA, FL, 34481
Community: Palm Cay

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3,584 homes near Winter Garden
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