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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
Arlington Ridge 4314 ARLINGTON RIDGE BLVD, LEESBURG, FL,..., Leesburg, FL 34748
$335,000

2 beds

|

2 baths

|

1,824 sq ft

|

House

4314 ARLINGTON RIDGE BLVD, LEESBURG, FL,...
Community: Arlington Ridge
Carillon Lakes 3374 WATERLUTE WAY, LAKELAND, FL, 33811, Lakeland, FL 33811
$375,000

3 beds

|

3 baths

|

1,891 sq ft

|

House

3374 WATERLUTE WAY, LAKELAND, FL, 33811
Community: Carillon Lakes
Solivita 644 SHOREHAVEN DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$400,000

2 beds

|

3 baths

|

2,344 sq ft

|

House

644 SHOREHAVEN DR, KISSIMMEE, FL, 34759
Community: Solivita
Ocala Preserve 5333 NW 33RD PL, OCALA, FL, 34482, Ocala, FL 34482
$275,000

2 beds

|

2 baths

|

1,368 sq ft

|

Halfplex

5333 NW 33RD PL, OCALA, FL, 34482
Community: Ocala Preserve
Sun City Center 2035 HAMPSTEAD CIR # 275, SUN CITY CENTE..., Sun City Center, FL 33573
$225,000

2 beds

|

2 baths

|

1,378 sq ft

|

Condo

2035 HAMPSTEAD CIR # 275, SUN CITY CENTE...
Community: Sun City Center
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Tampa Bay Golf and Country Club 29307 SCHINNECOCK HILLS LN, SAN ANTONIO,..., San Antonio, FL 33576
$300,000

2 beds

|

2 baths

|

1,398 sq ft

|

House

29307 SCHINNECOCK HILLS LN, SAN ANTONIO,...
Pelican Bay Daytona Beach 169 MALLARD LN, DAYTONA BEACH, FL, 32119, Daytona Beach, FL 32119
$574,900

3 beds

|

3 baths

|

2,700 sq ft

|

House

169 MALLARD LN, DAYTONA BEACH, FL, 32119
Pennbrooke Fairways 224 WESTWOOD DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$150,000

2 beds

|

2 baths

|

768 sq ft

|

Manufactured Home

224 WESTWOOD DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
On Top of the World 9287 SW 91ST COURT RD, OCALA, FL, 34481, Ocala, FL 34481
$184,900

3 beds

|

2 baths

|

1,579 sq ft

|

Villa

9287 SW 91ST COURT RD, OCALA, FL, 34481
Community: On Top of the World
Spruce Creek Country Club 9175 SE 118TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$289,900

2 beds

|

2 baths

|

1,488 sq ft

|

House

9175 SE 118TH LOOP, SUMMERFIELD, FL, 344...
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.
Spruce Creek Country Club 14315 SE 85TH AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$269,900

2 beds

|

2 baths

|

1,374 sq ft

|

House

14315 SE 85TH AVE, SUMMERFIELD, FL, 3449...
Majestic Oaks Ocala 8120 SW 56TH TER, OCALA, FL, 34476, Ocala, FL 34476
$354,900

3 beds

|

2 baths

|

1,843 sq ft

|

House

8120 SW 56TH TER, OCALA, FL, 34476
Community: Majestic Oaks Ocala
Spruce Creek South 10683 SE 174TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491
$279,900

3 beds

|

2 baths

|

1,620 sq ft

|

House

10683 SE 174TH LOOP, SUMMERFIELD, FL, 34...
Community: Spruce Creek South
On Top of the World 9051 SW 96TH LN B, OCALA, FL, 34481, Ocala, FL 34481
$198,244

2 beds

|

2 baths

|

1,709 sq ft

|

Villa

9051 SW 96TH LN B, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 9320 SW 89TH TER C, OCALA, FL, 34481, Ocala, FL 34481
$192,500

2 beds

|

2 baths

|

1,215 sq ft

|

Villa

9320 SW 89TH TER C, 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
Lake Ashton 4480 TURNBERRY LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$245,000

2 beds

|

2 baths

|

1,083 sq ft

|

House

4480 TURNBERRY LN, LAKE WALES, FL, 33859
Community: Lake Ashton
Del Webb Oasis 12253 BRACCO ST, WINTER GARDEN, FL, 3478..., Winter Garden, FL 34787
$575,000

3 beds

|

3 baths

|

1,788 sq ft

|

House

12253 BRACCO ST, WINTER GARDEN, FL, 3478...
Community: Del Webb Oasis
The Villages® 620 DOMINGUEZ DR, THE VILLAGES, FL, 3215..., The Villages, FL 32159
$284,000

2 beds

|

2 baths

|

1,094 sq ft

|

Villa

620 DOMINGUEZ DR, THE VILLAGES, FL, 3215...
Community: The Villages®
On Top of the World 9372 SW 90TH ST, OCALA, FL, 34481, Ocala, FL 34481
$279,900

2 beds

|

2 baths

|

1,923 sq ft

|

House

9372 SW 90TH ST, OCALA, FL, 34481
Community: On Top of the World
Stonecrest 12342 SE 176TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491
$358,900

2 beds

|

2 baths

|

1,764 sq ft

|

House

12342 SE 176TH LOOP, SUMMERFIELD, FL, 34...
Community: Stonecrest
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.
Highlands Ridge 3108 OAKMONT DR, AVON PARK, FL, 33825, Avon Park, FL 33825
$344,900

3 beds

|

2 baths

|

1,854 sq ft

|

House

3108 OAKMONT DR, AVON PARK, FL, 33825
Community: Highlands Ridge
Latitude Margaritaville 126 OCEAN HAMMOCK LOOP, DAYTONA BEACH, F..., Daytona Beach, FL 32124
$385,000

2 beds

|

2 baths

|

1,321 sq ft

|

House

126 OCEAN HAMMOCK LOOP, DAYTONA BEACH, F...
Del Webb Orlando 745 ASTURIAS RD, DAVENPORT, FL, 33837, Davenport, FL 33837
$375,000

2 beds

|

2 baths

|

1,468 sq ft

|

House

745 ASTURIAS RD, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Venetian Bay 214 CARYOTA CT, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$410,000

3 beds

|

2 baths

|

1,649 sq ft

|

House

214 CARYOTA CT, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
Kings Ridge 3603 EVERSHOLT ST, CLERMONT, FL, 34711, Clermont, FL 34711
$327,500

2 beds

|

2 baths

|

1,374 sq ft

|

House

3603 EVERSHOLT ST, CLERMONT, FL, 34711
Community: Kings Ridge
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Summit Greens 2294 CALEDONIAN ST, CLERMONT, FL, 34711, Clermont, FL 34711
$410,000

2 beds

|

2 baths

|

1,681 sq ft

|

House

2294 CALEDONIAN ST, CLERMONT, FL, 34711
Community: Summit Greens
Oak Run 8597 SW 108TH LANE RD, OCALA, FL, 34481, Ocala, FL 34481
$270,000

3 beds

|

2 baths

|

1,950 sq ft

|

House

8597 SW 108TH LANE RD, OCALA, FL, 34481
Community: Oak Run
Sullivan Ranch 22004 BELGIAN CT, MOUNT DORA, FL, 32757, Mount Dora, FL 32757
$325,000

3 beds

|

2 baths

|

1,437 sq ft

|

House

22004 BELGIAN CT, MOUNT DORA, FL, 32757
Community: Sullivan Ranch
Royal Highlands 5137 LINKS LN, LEESBURG, FL, 34748, Leesburg, FL 34748
$400,000

3 beds

|

2 baths

|

2,189 sq ft

|

House

5137 LINKS LN, LEESBURG, FL, 34748
Community: Royal Highlands
Valencia Lakes 16142 AMETHYST KEY DR, WIMAUMA, FL, 3359..., Wimauma, FL 33598
$289,000

3 beds

|

2 baths

|

1,709 sq ft

|

Villa

16142 AMETHYST KEY DR, WIMAUMA, FL, 3359...
Community: Valencia Lakes
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.
Lake Ashton 4327 GULLANE DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$349,900

2 beds

|

2 baths

|

1,860 sq ft

|

House

4327 GULLANE DR, LAKE WALES, FL, 33859
Community: Lake Ashton
Enclave at VillageWalk 10819 SAVONA WAY, ORLANDO, FL, 32827, Orlando, FL 32827
$1,599,000

5 beds

|

6 baths

|

5,437 sq ft

|

House

10819 SAVONA WAY, ORLANDO, FL, 32827
Lakes of Mount Dora 8167 BRIDGEPORT BAY CIR, MOUNT DORA, FL,..., Mount Dora, FL 32757
$435,000

3 beds

|

2 baths

|

1,613 sq ft

|

House

8167 BRIDGEPORT BAY CIR, MOUNT DORA, FL,...
Community: Lakes of Mount Dora
On Top of the World 8111 SW 95TH CT, OCALA, FL, 34481, Ocala, FL 34481
$525,000

3 beds

|

3 baths

|

2,311 sq ft

|

House

8111 SW 95TH CT, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 8635 SW 83RD LOOP, OCALA, FL, 34481, Ocala, FL 34481
$425,626

3 beds

|

2 baths

|

2,331 sq ft

|

House

8635 SW 83RD LOOP, 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
SummerGlen 16215 SW 15TH CT, OCALA, FL, 34473, Ocala, FL 34473
$349,900

3 beds

|

2 baths

|

2,018 sq ft

|

House

16215 SW 15TH CT, OCALA, FL, 34473
Community: SummerGlen
Valencia del Sol 15503 CORONA DEL MAR DR, WIMAUMA, FL, 33..., Wimauma, FL 33598
$699,900

3 beds

|

3 baths

|

2,252 sq ft

|

House

15503 CORONA DEL MAR DR, WIMAUMA, FL, 33...
Community: Valencia del Sol
Sun City Center 703 BEL AIR AVE, SUN CITY CENTER, FL, 33..., Sun City Center, FL 33573
$285,000

2 beds

|

2 baths

|

1,691 sq ft

|

House

703 BEL AIR AVE, SUN CITY CENTER, FL, 33...
Community: Sun City Center
Latitude Margaritaville 790 CORAL REEF WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$514,900

2 beds

|

3 baths

|

1,743 sq ft

|

House

790 CORAL REEF WAY, DAYTONA BEACH, FL, 3...
The Villages® 1801 MARQUEZ LOOP, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$339,900

2 beds

|

2 baths

|

1,146 sq ft

|

House

1801 MARQUEZ LOOP, LADY LAKE, FL, 32159
Community: The Villages®

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3,958 homes near Winter Garden
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