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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!
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.
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
The Villages® 8932 SE 168TH SEDGWICK PL, THE VILLAGES,..., The Villages, FL 32162
$279,900

3 beds

|

2 baths

|

1,483 sq ft

|

Villa

8932 SE 168TH SEDGWICK PL, THE VILLAGES,...
Community: The Villages®
Traditions at Lake Ruby 2919 WOODWARD LN, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$350,000

3 beds

|

2 baths

|

1,649 sq ft

|

House

2919 WOODWARD LN, WINTER HAVEN, FL, 3388...
Sun City Center 2128 WORTHINGTON GREENS DR, SUN CITY CEN..., Sun City Center, FL 33573
$349,000

2 beds

|

2 baths

|

1,989 sq ft

|

House

2128 WORTHINGTON GREENS DR, SUN CITY CEN...
Community: Sun City Center
Twin Lakes 2482 YELLOW BRICK RD, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34772
$304,900

2 beds

|

2 baths

|

1,346 sq ft

|

Villa

2482 YELLOW BRICK RD, SAINT CLOUD, FL, 3...
Community: Twin Lakes
High Vista at Ridgewood Lakes 53 HIGH VISTA DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$325,000

3 beds

|

2 baths

|

1,856 sq ft

|

House

53 HIGH VISTA DR, DAVENPORT, FL, 33837
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Solivita 453 SORRENTO RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$474,900

3 beds

|

4 baths

|

2,580 sq ft

|

House

453 SORRENTO RD, KISSIMMEE, FL, 34759
Community: Solivita
The Villages® 907 TRIFU TER, THE VILLAGES, FL, 32163, The Villages, FL 32163
$639,900

3 beds

|

2 baths

|

1,918 sq ft

|

House

907 TRIFU TER, THE VILLAGES, FL, 32163
Community: The Villages®
Del Webb Oasis 14111 FRASIER ST, WINTER GARDEN, FL, 347..., Winter Garden, FL 34787
$565,000

3 beds

|

3 baths

|

2,206 sq ft

|

House

14111 FRASIER ST, WINTER GARDEN, FL, 347...
Community: Del Webb Oasis
Ocala Palms 1960 NW 50TH CIR, OCALA, FL, 34482, Ocala, FL 34482
$349,500

3 beds

|

2 baths

|

1,838 sq ft

|

House

1960 NW 50TH CIR, OCALA, FL, 34482
Community: Ocala Palms
Sullivan Ranch 30532 GIDRAN TER, MOUNT DORA, FL, 32757, Mount Dora, FL 32757
$500,000

4 beds

|

2 baths

|

2,426 sq ft

|

House

30532 GIDRAN TER, MOUNT DORA, FL, 32757
Community: Sullivan Ranch
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 1906 CANTERBURY LN 16, SUN CITY CENTER, ..., Sun City Center, FL 33573
$185,000

2 beds

|

2 baths

|

984 sq ft

|

Condo

1906 CANTERBURY LN 16, SUN CITY CENTER, ...
Community: Sun City Center
Solivita 321 AUBURN AVE, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$735,000

5 beds

|

6 baths

|

2,945 sq ft

|

House

321 AUBURN AVE, KISSIMMEE, FL, 34747
Community: Solivita
On Top of the World 10406 SW 96TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$265,000

2 beds

|

2 baths

|

1,432 sq ft

|

House

10406 SW 96TH LOOP, OCALA, FL, 34481
Community: On Top of the World
Ocala Palms 1900 NW 57TH CT, OCALA, FL, 34482, Ocala, FL 34482
$299,999

3 beds

|

2 baths

|

1,692 sq ft

|

House

1900 NW 57TH CT, OCALA, FL, 34482
Community: Ocala Palms
Palms at Serenoa 17386 BLAZING STAR CIR, CLERMONT, FL, 34..., Clermont, FL 34714
$379,000

3 beds

|

2 baths

|

1,621 sq ft

|

House

17386 BLAZING STAR CIR, CLERMONT, FL, 34...
Community: Palms at Serenoa
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Harbor Hills Country Club 39023 GRIFFIN LNDG, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$546,000

3 beds

|

3 baths

|

2,833 sq ft

|

House

39023 GRIFFIN LNDG, LADY LAKE, FL, 32159
Highland Fairways 3748 INNISBROOK DR, LAKELAND, FL, 33810, Lakeland, FL 33810
$317,777

3 beds

|

2 baths

|

1,680 sq ft

|

House

3748 INNISBROOK DR, LAKELAND, FL, 33810
Community: Highland Fairways
Ocala Palms 2310 NW 59TH AVE, OCALA, FL, 34482, Ocala, FL 34482
$345,000

3 beds

|

2 baths

|

2,113 sq ft

|

House

2310 NW 59TH AVE, OCALA, FL, 34482
Community: Ocala Palms
The Villages® 13103 SANDALWOOD DR # 13103, WILDWOOD, F..., Wildwood, FL 34785
$120,000

2 beds

|

1 baths

|

1,000 sq ft

|

Condo

13103 SANDALWOOD DR # 13103, WILDWOOD, F...
Community: The Villages®
Sun City Center 718 DESERT HILLS WAY, SUN CITY CENTER, F..., Sun City Center, FL 33573
$450,000

3 beds

|

2 baths

|

1,775 sq ft

|

House

718 DESERT HILLS WAY, SUN CITY CENTER, F...
Community: Sun City Center
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.
Twin Lakes 2666 MEADOWEDGE LOOP, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34772
$668,000

4 beds

|

3 baths

|

2,935 sq ft

|

House

2666 MEADOWEDGE LOOP, SAINT CLOUD, FL, 3...
Community: Twin Lakes
The Lakes at Harmony 7520 CASTLEWOOD CT, HARMONY, FL, 34773, Harmony, FL 34773
$401,990

2 beds

|

2 baths

|

1,455 sq ft

|

House

7520 CASTLEWOOD CT, HARMONY, FL, 34773
Twin Lakes 5031 DANCY LN, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772
$420,000

2 beds

|

2 baths

|

1,423 sq ft

|

House

5031 DANCY LN, SAINT CLOUD, FL, 34772
Community: Twin Lakes
The Lakes at Harmony 3156 SONGBIRD CIR, HARMONY, FL, 34773, Harmony, FL 34773
$399,990

2 beds

|

2 baths

|

1,423 sq ft

|

House

3156 SONGBIRD CIR, HARMONY, FL, 34773
Twin Lakes 2335 DATURA LOOP, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772
$340,000

2 beds

|

2 baths

|

1,351 sq ft

|

Villa

2335 DATURA LOOP, SAINT CLOUD, FL, 34772
Community: Twin Lakes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Twin Lakes 2331 DATURA LOOP, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772
$355,000

2 beds

|

2 baths

|

1,449 sq ft

|

Villa

2331 DATURA LOOP, SAINT CLOUD, FL, 34772
Community: Twin Lakes
Twin Lakes 2337 DATURA LOOP, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772
$340,000

2 beds

|

2 baths

|

1,351 sq ft

|

Villa

2337 DATURA LOOP, SAINT CLOUD, FL, 34772
Community: Twin Lakes
Twin Lakes 2323 DATURA LOOP, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772
$355,000

2 beds

|

2 baths

|

1,449 sq ft

|

Villa

2323 DATURA LOOP, SAINT CLOUD, FL, 34772
Community: Twin Lakes
Pine Run Estates 10040 SW 98TH AVE, OCALA, FL, 34481, Ocala, FL 34481
$168,000

2 beds

|

2 baths

|

1,144 sq ft

|

House

10040 SW 98TH AVE, OCALA, FL, 34481
Community: Pine Run Estates
Cresswind DeLand 1285 JACKSON HOLE CT, DELAND, FL, 32724, Deland, FL 32724
$459,990

3 beds

|

2 baths

|

1,724 sq ft

|

House

1285 JACKSON HOLE CT, DELAND, FL, 32724
Community: Cresswind DeLand
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.
Cresswind DeLand 1276 JACKSON HOLE CT, DELAND, FL, 32724, Deland, FL 32724
$434,890

2 beds

|

2 baths

|

1,434 sq ft

|

House

1276 JACKSON HOLE CT, DELAND, FL, 32724
Community: Cresswind DeLand
Spruce Creek Country Club 13875 SE 97TH AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$248,900

2 beds

|

2 baths

|

1,296 sq ft

|

House

13875 SE 97TH AVE, SUMMERFIELD, FL, 3449...
Cresswind at Victoria Gardens 145 OLD MOSS CIR, DELAND, FL, 32724, Deland, FL 32724
$677,900

3 beds

|

3 baths

|

2,222 sq ft

|

House

145 OLD MOSS CIR, DELAND, FL, 32724
Harbor Hills Country Club 39504 HILLRISE LN, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$569,500

3 beds

|

2 baths

|

2,340 sq ft

|

House

39504 HILLRISE LN, LADY LAKE, FL, 32159
SummerGlen 1813 SW 157TH PLACE RD, OCALA, FL, 34473, Ocala, FL 34473
$285,900

3 beds

|

2 baths

|

1,759 sq ft

|

House

1813 SW 157TH PLACE RD, OCALA, FL, 34473
Community: SummerGlen
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
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
On Top of the World 8745 SW 92ND ST B, OCALA, FL, 34481, Ocala, FL 34481
$229,000

2 beds

|

2 baths

|

1,652 sq ft

|

Villa

8745 SW 92ND ST B, OCALA, FL, 34481
Community: On Top of the World
The Lakes at Harmony 3428 SAGEBRUSH ST, HARMONY, FL, 34773, Harmony, FL 34773
$375,000

3 beds

|

2 baths

|

1,474 sq ft

|

House

3428 SAGEBRUSH ST, HARMONY, FL, 34773
Sun City Center 204 CACTUSFLOWER LN, SUN CITY CENTER, FL..., Sun City Center, FL 33573
$295,000

2 beds

|

2 baths

|

1,804 sq ft

|

House

204 CACTUSFLOWER LN, SUN CITY CENTER, FL...
Community: Sun City Center
Sun City Center 604 MCDANIEL ST, SUN CITY CENTER, FL, 33..., Sun City Center, FL 33573
$299,999

3 beds

|

3 baths

|

2,105 sq ft

|

Condo

604 MCDANIEL ST, SUN CITY CENTER, FL, 33...
Community: Sun City Center

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3,573 homes near Winter Garden
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