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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
SummerGlen 1768 SW 156TH LN, OCALA, FL, 34473, Ocala, FL 34473
$263,500

2 beds

|

2 baths

|

1,570 sq ft

|

House

1768 SW 156TH LN, OCALA, FL, 34473
Community: SummerGlen
On Top of the World 6571 SW 81ST LOOP, OCALA, FL, 34476, Ocala, FL 34476
$224,990

3 beds

|

3 baths

|

1,458 sq ft

|

Townhouse

6571 SW 81ST LOOP, OCALA, FL, 34476
Community: On Top of the World
On Top of the World 6579 SW 81ST LOOP, OCALA, FL, 34476, Ocala, FL 34476
$224,990

3 beds

|

3 baths

|

1,458 sq ft

|

Townhouse

6579 SW 81ST LOOP, OCALA, FL, 34476
Community: On Top of the World
The Villages® 3001 SAINT THOMAS LN, THE VILLAGES, FL, ..., The Villages, FL 32162
$315,000

3 beds

|

2 baths

|

1,520 sq ft

|

House

3001 SAINT THOMAS LN, THE VILLAGES, FL, ...
Community: The Villages®
VillageWalk at Lake Nona 12185 OBELIA LN, ORLANDO, FL, 32827, Orlando, FL 32827
$630,000

3 beds

|

3 baths

|

2,022 sq ft

|

House

12185 OBELIA LN, ORLANDO, FL, 32827
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
On Top of the World 9274 SW 94TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$339,750

3 beds

|

2 baths

|

2,010 sq ft

|

House

9274 SW 94TH LOOP, OCALA, FL, 34481
Community: On Top of the World
The Villages® 17353 SE 76TH FLINTLOCK TER, THE VILLAGE..., The Villages, FL 32162
$284,900

2 beds

|

2 baths

|

1,388 sq ft

|

House

17353 SE 76TH FLINTLOCK TER, THE VILLAGE...
Community: The Villages®
Plantation at Leesburg 5036 SAWGRASS LAKE CIR, LEESBURG, FL, 34..., Leesburg, FL 34748
$369,900

3 beds

|

3 baths

|

2,439 sq ft

|

House

5036 SAWGRASS LAKE CIR, LEESBURG, FL, 34...
Solivita 1192 VIA GALUPPI ST, POINCIANA, FL, 3475..., Poinciana, FL 34759
$365,000

3 beds

|

2 baths

|

1,723 sq ft

|

House

1192 VIA GALUPPI ST, POINCIANA, FL, 3475...
Community: Solivita
The Villages® 9345 SE 177TH SIMONS LN, THE VILLAGES, F..., The Villages, FL 32162
$325,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

9345 SE 177TH SIMONS LN, THE VILLAGES, F...
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.
On Top of the World 8433 SW 98TH TERRACE RD, OCALA, FL, 3448..., Ocala, FL 34481
$554,000

3 beds

|

3 baths

|

2,373 sq ft

|

House

8433 SW 98TH TERRACE RD, OCALA, FL, 3448...
Community: On Top of the World
Sun City Center 2016 NEW BEDFORD DR, SUN CITY CENTER, FL..., Sun City Center, FL 33573
$395,000

3 beds

|

2 baths

|

2,366 sq ft

|

House

2016 NEW BEDFORD DR, SUN CITY CENTER, FL...
Community: Sun City Center
The Villages® 2895 APACHE CT, THE VILLAGES, FL, 32163, The Villages, FL 32163
$468,000

3 beds

|

2 baths

|

1,865 sq ft

|

House

2895 APACHE CT, THE VILLAGES, FL, 32163
Community: The Villages®
Stonecrest 17739 SE 121ST TERRACE RD, SUMMERFIELD, ..., Summerfield, FL 34491
$314,900

2 beds

|

2 baths

|

1,572 sq ft

|

House

17739 SE 121ST TERRACE RD, SUMMERFIELD, ...
Community: Stonecrest
Heritage Hills 3788 SERENA LN, CLERMONT, FL, 34711, Clermont, FL 34711
$399,000

3 beds

|

2 baths

|

1,672 sq ft

|

House

3788 SERENA LN, CLERMONT, FL, 34711
Community: Heritage Hills
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
On Top of the World 10277 SW 105TH CT, OCALA, FL, 34481, Ocala, FL 34481
$510,000

3 beds

|

3 baths

|

2,907 sq ft

|

House

10277 SW 105TH CT, OCALA, FL, 34481
Community: On Top of the World
Del Webb Sunbridge 3013 CHERRY BLOSSOM LOOP, SAINT CLOUD, F..., Saint Cloud, FL 34771
$370,000

3 beds

|

2 baths

|

1,584 sq ft

|

House

3013 CHERRY BLOSSOM LOOP, SAINT CLOUD, F...
Community: Del Webb Sunbridge
Cypress Lakes 2143 CYPRESS CROSS DR, LAKELAND, FL, 338..., Lakeland, FL 33810
$199,000

3 beds

|

2 baths

|

1,568 sq ft

|

Manufactured Home

2143 CYPRESS CROSS DR, LAKELAND, FL, 338...
Community: Cypress Lakes
Del Webb Minneola 2761 TOP HILL CT, MINNEOLA, FL, 34715, Minneola, FL 34715
$599,900

2 beds

|

2 baths

|

1,943 sq ft

|

House

2761 TOP HILL CT, MINNEOLA, FL, 34715
Community: Del Webb Minneola
Solivita 1824 PELICAN HILL WAY, POINCIANA, FL, 34..., Poinciana, FL 34759
$269,000

2 beds

|

2 baths

|

1,515 sq ft

|

House

1824 PELICAN HILL WAY, POINCIANA, FL, 34...
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.
Royal Highlands 20631 PRINCE RANIER PL, LEESBURG, FL, 34..., Leesburg, FL 34748
$375,000

3 beds

|

2 baths

|

2,070 sq ft

|

House

20631 PRINCE RANIER PL, LEESBURG, FL, 34...
Community: Royal Highlands
Valencia Lakes 16261 AMETHYST KEY DR, WIMAUMA, FL, 3359..., Wimauma, FL 33598
$255,000

2 beds

|

2 baths

|

1,291 sq ft

|

Villa

16261 AMETHYST KEY DR, WIMAUMA, FL, 3359...
Community: Valencia Lakes
Sun City Center 1034 MCDANIEL ST # 1034, SUN CITY CENTER..., Sun City Center, FL 33573
$287,000

2 beds

|

2 baths

|

1,887 sq ft

|

Condo

1034 MCDANIEL ST # 1034, SUN CITY CENTER...
Community: Sun City Center
Sun City Center 2113 E DEL WEBB BLVD, SUN CITY CENTER, F..., Sun City Center, FL 33573
$330,000

3 beds

|

3 baths

|

2,218 sq ft

|

House

2113 E DEL WEBB BLVD, SUN CITY CENTER, F...
Community: Sun City Center
Majestic Oaks Ocala 8100 SW 56TH TER, OCALA, FL, 34476, Ocala, FL 34476
$261,500

3 beds

|

2 baths

|

1,843 sq ft

|

House

8100 SW 56TH TER, OCALA, FL, 34476
Community: Majestic Oaks Ocala
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Latitude Margaritaville 237 BLUE STARFISH PL, DAYTONA BEACH, FL,..., Daytona Beach, FL 32124
$565,000

3 beds

|

2 baths

|

1,681 sq ft

|

House

237 BLUE STARFISH PL, DAYTONA BEACH, FL,...
Harbor Hills Country Club 5239 GROVE MNR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$399,999

3 beds

|

2 baths

|

2,284 sq ft

|

House

5239 GROVE MNR, LADY LAKE, FL, 32159
The Villages® 15102 SANDALWOOD DR # 102, WILDWOOD, FL,..., Wildwood, FL 34785
$169,000

3 beds

|

2 baths

|

1,474 sq ft

|

Condo

15102 SANDALWOOD DR # 102, WILDWOOD, FL,...
Community: The Villages®
Twin Lakes 2516 PICKETT AVE, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772
$519,000

3 beds

|

3 baths

|

2,208 sq ft

|

House

2516 PICKETT AVE, SAINT CLOUD, FL, 34772
Community: Twin Lakes
Del Webb Sunbridge 3112 RANGER DR, SAINT CLOUD, FL, 34771, Saint Cloud, FL 34771
$654,000

5 beds

|

4 baths

|

2,995 sq ft

|

House

3112 RANGER DR, SAINT CLOUD, FL, 34771
Community: Del Webb Sunbridge
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 2816 E VENETIAN LAKE CIR, NEW SMYRNA BEA..., New Smyrna Beach, FL 32168
$830,000

3 beds

|

3 baths

|

2,536 sq ft

|

House

2816 E VENETIAN LAKE CIR, NEW SMYRNA BEA...
Community: Venetian Bay
Harbor Hills Country Club 38748 LAKEVIEW WALK, LADY LAKE, FL, 3215..., Lady Lake, FL 32159
$420,000

3 beds

|

3 baths

|

2,471 sq ft

|

House

38748 LAKEVIEW WALK, LADY LAKE, FL, 3215...
Ocala Preserve 5616 NW 39TH LN, OCALA, FL, 34482, Ocala, FL 34482
$250,000

2 beds

|

2 baths

|

1,454 sq ft

|

House

5616 NW 39TH LN, OCALA, FL, 34482
Community: Ocala Preserve
Latitude Margaritaville 614 LANDSHARK BLVD, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$439,900

2 beds

|

2 baths

|

1,563 sq ft

|

House

614 LANDSHARK BLVD, DAYTONA BEACH, FL, 3...
Plantation at Leesburg 4552 PEACH TREE ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$274,900

3 beds

|

2 baths

|

1,709 sq ft

|

House

4552 PEACH TREE ST, LEESBURG, FL, 34748
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
SummerGlen 15239 SW 15TH TERRACE RD, OCALA, FL, 344..., Ocala, FL 34473
$200,000

3 beds

|

2 baths

|

2,312 sq ft

|

House

15239 SW 15TH TERRACE RD, OCALA, FL, 344...
Community: SummerGlen
The Villages® 605 JASON DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$145,000

2 beds

|

2 baths

|

768 sq ft

|

Manufactured Home

605 JASON DR, LADY LAKE, FL, 32159
Community: The Villages®
Summit Greens 1063 MESA VERDE CT, CLERMONT, FL, 34711, Clermont, FL 34711
$389,000

3 beds

|

2 baths

|

1,900 sq ft

|

House

1063 MESA VERDE CT, CLERMONT, FL, 34711
Community: Summit Greens
SummerGlen 16193 SW 14TH AVENUE RD, OCALA, FL, 3447..., Ocala, FL 34473
$274,900

3 beds

|

2 baths

|

1,647 sq ft

|

House

16193 SW 14TH AVENUE RD, OCALA, FL, 3447...
Community: SummerGlen
Venetian Bay 3615 MARISOL CT, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168
$549,900

3 beds

|

2 baths

|

1,764 sq ft

|

House

3615 MARISOL CT, NEW SMYRNA BEACH, FL, 3...
Community: Venetian Bay

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3,648 homes near Winter Garden
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