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

3,958 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 - $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
<$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
$200Ks - $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 - $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 - $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 - $600Ks
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 - $1Ms
Twin Lakes, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes
No reviews yet Pelican Bay Daytona Beach
<$100k - $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
$200Ks - $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 - $900Ks
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
$200Ks - $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) 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
$100Ks - $300Ks
Pennbrooke Fairways, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 homes
5 rating (1 reviews) Sandpiper Golf & Coun...
$100Ks - $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
$300Ks - $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 | 1,029 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 - $700Ks
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 homes
4 rating (4 reviews) Lakes of Mount Dora
$200Ks - $800Ks
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 - $800Ks
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
$100Ks - $300Ks
Highland Lakes, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes
4.3 rating (15 reviews) Del Webb Orlando
$200Ks - $500Ks
Del Webb Orlando, Davenport, FL
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes
No reviews yet Pine Run Estates
$100Ks - $400Ks
Pine Run Estates, Ocala, FL
Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 homes
No reviews yet Lake Jovita Golf and Coun...
$400Ks - $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 - $900Ks
Esplanade at Wiregrass Ra..., Wesley Chapel, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 868 homes
Latitude Margaritaville 227 CORAL REEF WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$507,900

2 beds

|

2 baths

|

1,786 sq ft

|

House

227 CORAL REEF WAY, DAYTONA BEACH, FL, 3...
Sun City Center 404 GRAND CHATEAUX WAY, SUN CITY CENTER,..., Sun City Center, FL 33573
$357,000

2 beds

|

2 baths

|

1,963 sq ft

|

House

404 GRAND CHATEAUX WAY, SUN CITY CENTER,...
Community: Sun City Center
Latitude Margaritaville 638 GOOD LIFE WAY, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32124
$419,900

2 beds

|

2 baths

|

1,464 sq ft

|

House

638 GOOD LIFE WAY, DAYTONA BEACH, FL, 32...
Twin Lakes 5043 VANTAGE CT, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772
$599,900

3 beds

|

3 baths

|

2,365 sq ft

|

House

5043 VANTAGE CT, SAINT CLOUD, FL, 34772
Community: Twin Lakes
Pennbrooke Fairways 32712 TIMBERWOOD DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$289,000

3 beds

|

2 baths

|

1,909 sq ft

|

House

32712 TIMBERWOOD DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Sun City Center 322 NORTHWAY DR, SUN CITY CENTER, FL, 33..., Sun City Center, FL 33573
$370,000

3 beds

|

2 baths

|

1,939 sq ft

|

House

322 NORTHWAY DR, SUN CITY CENTER, FL, 33...
Community: Sun City Center
Highland Lakes 6042 WADE ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$245,000

3 beds

|

2 baths

|

1,634 sq ft

|

House

6042 WADE ST, LEESBURG, FL, 34748
Community: Highland Lakes
Highlands Ridge 4008 CARTER CREEK DR, AVON PARK, FL, 338..., Avon Park, FL 33825
$295,000

3 beds

|

2 baths

|

1,767 sq ft

|

House

4008 CARTER CREEK DR, AVON PARK, FL, 338...
Community: Highlands Ridge
Hidden Creek 2500 HIDDEN CREEK CIR, SEBRING, FL, 3387..., Sebring, FL 33870
$260,000

2 beds

|

2 baths

|

1,281 sq ft

|

Villa

2500 HIDDEN CREEK CIR, SEBRING, FL, 3387...
Community: Hidden Creek
Solivita 560 PRESIDO PARK PL, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759
$285,000

2 beds

|

2 baths

|

1,658 sq ft

|

House

560 PRESIDO PARK PL, KISSIMMEE, FL, 3475...
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.
Stonecrest 11040 SE 174TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491
$259,900

2 beds

|

2 baths

|

1,463 sq ft

|

House

11040 SE 174TH LOOP, SUMMERFIELD, FL, 34...
Community: Stonecrest
Kings Ridge 2277 CALVERT CT, CLERMONT, FL, 34711, Clermont, FL 34711
$330,000

3 beds

|

2 baths

|

1,873 sq ft

|

House

2277 CALVERT CT, CLERMONT, FL, 34711
Community: Kings Ridge
Highland Fairways 1957 PRAIRIE DUNES CIR, LAKELAND, FL, 33..., Lakeland, FL 33810
$329,900

2 beds

|

2 baths

|

1,637 sq ft

|

House

1957 PRAIRIE DUNES CIR, LAKELAND, FL, 33...
Community: Highland Fairways
Harbor Hills Country Club 5509 GROVE MNR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$519,999

3 beds

|

3 baths

|

2,240 sq ft

|

House

5509 GROVE MNR, LADY LAKE, FL, 32159
Highland Fairways 3158 PEBBLE BEND DR, LAKELAND, FL, 33810, Lakeland, FL 33810
$199,900

2 beds

|

2 baths

|

1,034 sq ft

|

House

3158 PEBBLE BEND DR, LAKELAND, FL, 33810
Community: Highland Fairways
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Highland Fairways 3221 PEBBLE BEND DR, LAKELAND, FL, 33810, Lakeland, FL 33810
$229,900

2 beds

|

2 baths

|

1,456 sq ft

|

Manufactured Home

3221 PEBBLE BEND DR, LAKELAND, FL, 33810
Community: Highland Fairways
Ashley Oaks 2033 ASHLEY OAKS CIR, SEBRING, FL, 33870, Sebring, FL 33870
$249,500

3 beds

|

2 baths

|

1,396 sq ft

|

Villa

2033 ASHLEY OAKS CIR, SEBRING, FL, 33870
Community: Ashley Oaks
Ocala Palms 5495 NW 23RD PL, OCALA, FL, 34482, Ocala, FL 34482
$299,000

2 beds

|

2 baths

|

1,796 sq ft

|

House

5495 NW 23RD PL, OCALA, FL, 34482
Community: Ocala Palms
The Villages® 8185 COUNTY ROAD 109, LADY LAKE, FL, 321..., Lady Lake, FL 32159
$215,000

3 beds

|

2 baths

|

1,568 sq ft

|

Mobile Home

8185 COUNTY ROAD 109, LADY LAKE, FL, 321...
Community: The Villages®
On Top of the World 9694 SW 79TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$695,000

3 beds

|

3 baths

|

2,893 sq ft

|

House

9694 SW 79TH LOOP, OCALA, FL, 34481
Community: On Top of the World
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.
Latitude Margaritaville 596 HANG LOOSE WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$550,000

2 beds

|

2 baths

|

1,684 sq ft

|

House

596 HANG LOOSE WAY, DAYTONA BEACH, FL, 3...
The Villages® 3432 WISE WAY, THE VILLAGES, FL, 32163, The Villages, FL 32163
$1,249,000

4 beds

|

4 baths

|

2,548 sq ft

|

House

3432 WISE WAY, THE VILLAGES, FL, 32163
Community: The Villages®
Venetian Bay 2840 ISLES WAY, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$604,900

3 beds

|

3 baths

|

2,131 sq ft

|

Townhouse

2840 ISLES WAY, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
On Top of the World 8678 SW 83RD CIR, OCALA, FL, 34481, Ocala, FL 34481
$324,900

3 beds

|

2 baths

|

1,695 sq ft

|

House

8678 SW 83RD CIR, OCALA, FL, 34481
Community: On Top of the World
Plantation at Leesburg 25141 CLIFFORD HL, LEESBURG, FL, 34748, Leesburg, FL 34748
$259,900

3 beds

|

2 baths

|

1,727 sq ft

|

House

25141 CLIFFORD HL, LEESBURG, FL, 34748
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Valencia Lakes 16112 AMETHYST KEY DR, WIMAUMA, FL, 3359..., Wimauma, FL 33598
$309,500

3 beds

|

2 baths

|

1,524 sq ft

|

Villa

16112 AMETHYST KEY DR, WIMAUMA, FL, 3359...
Community: Valencia Lakes
Lake Henry Estates 492 SWEETWATER WAY, HAINES CITY, FL, 338..., Haines City, FL 33844
$268,000

2 beds

|

2 baths

|

1,508 sq ft

|

House

492 SWEETWATER WAY, HAINES CITY, FL, 338...
Community: Lake Henry Estates
Royal Highlands 5024 ST ANDREWS ARC, LEESBURG, FL, 34748, Leesburg, FL 34748
$329,900

3 beds

|

2 baths

|

1,808 sq ft

|

House

5024 ST ANDREWS ARC, LEESBURG, FL, 34748
Community: Royal Highlands
Alhambra Villas Condominiums 141 N HILL AVE 150, DELAND, FL, 32724, Deland, FL 32724
$195,000

2 beds

|

2 baths

|

979 sq ft

|

Condo

141 N HILL AVE 150, DELAND, FL, 32724
Breakaway Trails 56 WINDING CREEK WAY, ORMOND BEACH, FL, ..., Ormond Beach, FL 32174
$599,900

4 beds

|

3 baths

|

2,852 sq ft

|

House

56 WINDING CREEK WAY, ORMOND BEACH, FL, ...
Community: Breakaway Trails
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.
Latitude Margaritaville 651 LOST SHAKER WAY, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$398,900

2 beds

|

2 baths

|

1,464 sq ft

|

House

651 LOST SHAKER WAY, DAYTONA BEACH, FL, ...
The Lakes at Harmony 3415 SAGEBRUSH ST, HARMONY, FL, 34773, Harmony, FL 34773
$300,000

2 beds

|

2 baths

|

1,637 sq ft

|

House

3415 SAGEBRUSH ST, HARMONY, FL, 34773
Valencia Lakes 4936 SANDY BROOK CIR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$375,000

3 beds

|

2 baths

|

1,880 sq ft

|

House

4936 SANDY BROOK CIR, WIMAUMA, FL, 33598
Community: Valencia Lakes
High Vista at Ridgewood Lakes 231 RIDGE VIEW DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$315,000

3 beds

|

2 baths

|

1,776 sq ft

|

House

231 RIDGE VIEW DR, DAVENPORT, FL, 33837
The Lakes at Harmony 3144 SONGBIRD CIR, HARMONY, FL, 34773, Harmony, FL 34773
$419,900

3 beds

|

2 baths

|

1,852 sq ft

|

House

3144 SONGBIRD CIR, HARMONY, FL, 34773
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 1802 HARTFORD PATH, THE VILLAGES, FL, 32..., The Villages, FL 32162
$1,469,000

4 beds

|

3 baths

|

4,987 sq ft

|

House

1802 HARTFORD PATH, THE VILLAGES, FL, 32...
Community: The Villages®
On Top of the World 9093 SW 91ST CIR, OCALA, FL, 34481, Ocala, FL 34481
$272,900

2 beds

|

2 baths

|

1,629 sq ft

|

House

9093 SW 91ST CIR, OCALA, FL, 34481
Community: On Top of the World
Solivita 684 SAN AUGUSTO DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$539,000

3 beds

|

3 baths

|

2,363 sq ft

|

House

684 SAN AUGUSTO DR, POINCIANA, FL, 34759
Community: Solivita
Heritage Hills 3948 SERENA LN, CLERMONT, FL, 34711, Clermont, FL 34711
$389,899

3 beds

|

2 baths

|

1,561 sq ft

|

House

3948 SERENA LN, CLERMONT, FL, 34711
Community: Heritage Hills
Lake Ashton 5341 HOGAN LN, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$334,900

3 beds

|

3 baths

|

1,682 sq ft

|

House

5341 HOGAN LN, WINTER HAVEN, FL, 33884
Community: Lake Ashton

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3,958 homes near Winter Garden
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