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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
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
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
Summer Trees 6065 SPRUCE POINT CIR, PORT ORANGE, FL, ..., Port Orange, FL 32128
$629,900

4 beds

|

3 baths

|

2,806 sq ft

|

House

6065 SPRUCE POINT CIR, PORT ORANGE, FL, ...
Community: Summer Trees
Sun City Center 1012 AUGUSTA DR, SUN CITY CENTER, FL, 33..., Sun City Center, FL 33573
$289,000

2 beds

|

2 baths

|

1,334 sq ft

|

House

1012 AUGUSTA DR, SUN CITY CENTER, FL, 33...
Community: Sun City Center
Venetian Bay 354 N AIRPORT RD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$339,999

2 beds

|

3 baths

|

1,837 sq ft

|

Townhouse

354 N AIRPORT RD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Stonecrest 17355 SE 110TH TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$428,000

3 beds

|

3 baths

|

2,179 sq ft

|

House

17355 SE 110TH TER, SUMMERFIELD, FL, 344...
Community: Stonecrest
Sun City Center 101 CAMBRIDGE TRL APT 194, SUN CITY CENT..., Sun City Center, FL 33573
$100,000

1 beds

|

2 baths

|

800 sq ft

|

Condo

101 CAMBRIDGE TRL APT 194, SUN CITY CENT...
Community: Sun City Center
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Pennbrooke Fairways 32712 TIMBERWOOD DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$284,900

3 beds

|

2 baths

|

1,909 sq ft

|

House

32712 TIMBERWOOD DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Spruce Creek North 6366 SW 115TH STREET RD, OCALA, FL, 3447..., Ocala, FL 34476
$197,000

2 beds

|

2 baths

|

1,144 sq ft

|

House

6366 SW 115TH STREET RD, OCALA, FL, 3447...
Community: Spruce Creek North
Royal Highlands 4802 GLEN COE ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$475,000

2 beds

|

2 baths

|

3,034 sq ft

|

House

4802 GLEN COE ST, LEESBURG, FL, 34748
Community: Royal Highlands
Sun City Center 102 CAMBRIDGE TRL 217, SUN CITY CENTER, ..., Sun City Center, FL 33573
$115,000

2 beds

|

2 baths

|

960 sq ft

|

Condo

102 CAMBRIDGE TRL 217, SUN CITY CENTER, ...
Community: Sun City Center
Summit Greens 2185 CALEDONIAN ST, CLERMONT, FL, 34711, Clermont, FL 34711
$359,900

3 beds

|

2 baths

|

1,946 sq ft

|

House

2185 CALEDONIAN ST, CLERMONT, FL, 34711
Community: Summit Greens
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.
Plantation at Leesburg 5503 ZINNIA ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$260,000

2 beds

|

2 baths

|

1,316 sq ft

|

House

5503 ZINNIA ST, LEESBURG, FL, 34748
Traditions at Lake Ruby 4051 BEDFORD AVE, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$349,900

2 beds

|

2 baths

|

1,868 sq ft

|

House

4051 BEDFORD AVE, WINTER HAVEN, FL, 3388...
Sun City Center 1257 CORINTH GREENS DR # 1257, SUN CITY ..., Sun City Center, FL 33573
$224,000

2 beds

|

2 baths

|

1,435 sq ft

|

Condo

1257 CORINTH GREENS DR # 1257, SUN CITY ...
Community: Sun City Center
Latitude Margaritaville 512 LANDSHARK BLVD, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$392,999

2 beds

|

2 baths

|

1,482 sq ft

|

House

512 LANDSHARK BLVD, DAYTONA BEACH, FL, 3...
Breakaway Trails 6 BLACK PINE WAY, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174
$699,000

4 beds

|

4 baths

|

3,289 sq ft

|

House

6 BLACK PINE WAY, ORMOND BEACH, FL, 3217...
Community: Breakaway Trails
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
On Top of the World 9064 SW 91ST CIR, OCALA, FL, 34481, Ocala, FL 34481
$200,000

3 beds

|

2 baths

|

2,021 sq ft

|

House

9064 SW 91ST CIR, OCALA, FL, 34481
Community: On Top of the World
Sun City Center 2510 LOCKSLEY ST # 2510, SUN CITY CENTER..., Sun City Center, FL 33573
$255,500

2 beds

|

2 baths

|

1,394 sq ft

|

Condo

2510 LOCKSLEY ST # 2510, SUN CITY CENTER...
Community: Sun City Center
Latitude Margaritaville 713 LANDSHARK BLVD, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$629,900

2 beds

|

2 baths

|

1,939 sq ft

|

House

713 LANDSHARK BLVD, DAYTONA BEACH, FL, 3...
Latitude Margaritaville 1078 CASTAWAY CT, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124
$684,900

2 beds

|

3 baths

|

2,080 sq ft

|

House

1078 CASTAWAY CT, DAYTONA BEACH, FL, 321...
On Top of the World 10248 SW 93RD PL, OCALA, FL, 34481, Ocala, FL 34481
$625,000

3 beds

|

3 baths

|

2,828 sq ft

|

House

10248 SW 93RD PL, 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.
Highland Lakes 5606 LAVER ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$295,000

3 beds

|

2 baths

|

1,919 sq ft

|

House

5606 LAVER ST, LEESBURG, FL, 34748
Community: Highland Lakes
Trilogy® Orlando 201 SILVER MAPLE RD, GROVELAND, FL, 3473..., Groveland, FL 34736
$499,000

4 beds

|

3 baths

|

2,267 sq ft

|

House

201 SILVER MAPLE RD, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
Sun City Center 322 GLOUCESTER BLVD # 322, SUN CITY CENT..., Sun City Center, FL 33573
$131,500

1 beds

|

2 baths

|

800 sq ft

|

Condo

322 GLOUCESTER BLVD # 322, SUN CITY CENT...
Community: Sun City Center
Latitude Margaritaville 109 COASTAL AVE, DAYTONA BEACH, FL, 3212..., Daytona Beach, FL 32124
$509,900

2 beds

|

3 baths

|

1,743 sq ft

|

House

109 COASTAL AVE, DAYTONA BEACH, FL, 3212...
Summer Trees 130 CYPRESS POND RD, PORT ORANGE, FL, 32..., Port Orange, FL 32128
$274,950

3 beds

|

2 baths

|

1,363 sq ft

|

House

130 CYPRESS POND RD, PORT ORANGE, FL, 32...
Community: Summer Trees
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 111 SUGAR MAPLE AVE, WILDWOOD, FL, 34785, Wildwood, FL 34785
$158,000

2 beds

|

2 baths

|

1,152 sq ft

|

Manufactured Home

111 SUGAR MAPLE AVE, WILDWOOD, FL, 34785
Community: The Villages®
Spruce Creek South 10338 SE 178TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$219,000

2 beds

|

2 baths

|

1,008 sq ft

|

House

10338 SE 178TH ST, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
On Top of the World 7881 SW 89TH LOOP, OCALA, FL, 34476, Ocala, FL 34476
$279,990

2 beds

|

2 baths

|

1,342 sq ft

|

House

7881 SW 89TH LOOP, OCALA, FL, 34476
Community: On Top of the World
Solivita 1405 HARBOR RIDGE DR, KISSIMMEE, FL, 347..., Kissimmee, FL 34759
$304,900

2 beds

|

2 baths

|

1,543 sq ft

|

House

1405 HARBOR RIDGE DR, KISSIMMEE, FL, 347...
Community: Solivita
Solivita 313 SANTA BARBARA LN, KISSIMMEE, FL, 347..., Kissimmee, FL 34759
$459,900

2 beds

|

3 baths

|

2,343 sq ft

|

House

313 SANTA BARBARA LN, KISSIMMEE, FL, 347...
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.
Plantation at Leesburg 25012 LAUREL VALLEY RD, LEESBURG, FL, 34..., Leesburg, FL 34748
$324,500

2 beds

|

2 baths

|

2,030 sq ft

|

House

25012 LAUREL VALLEY RD, LEESBURG, FL, 34...
The Villages® 2378 HILL ST, THE VILLAGES, FL, 32163, The Villages, FL 32163
$334,900

2 beds

|

2 baths

|

1,159 sq ft

|

Villa

2378 HILL ST, THE VILLAGES, FL, 32163
Community: The Villages®
Solivita 507 PRESIDO PARK PL, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759
$310,000

2 beds

|

2 baths

|

1,302 sq ft

|

House

507 PRESIDO PARK PL, KISSIMMEE, FL, 3475...
Community: Solivita
On Top of the World 8630 SW 94TH LN A, OCALA, FL, 34481, Ocala, FL 34481
$196,500

2 beds

|

2 baths

|

1,531 sq ft

|

Villa

8630 SW 94TH LN A, OCALA, FL, 34481
Community: On Top of the World
The Villages® 1737 LAUREN LN, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$339,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

1737 LAUREN LN, LADY LAKE, FL, 32159
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
SummerGlen 15771 SW 16TH TER, OCALA, FL, 34473, Ocala, FL 34473
$408,000

3 beds

|

2 baths

|

2,516 sq ft

|

House

15771 SW 16TH TER, OCALA, FL, 34473
Community: SummerGlen
Ocala Preserve 5235 NW 33RD PL, OCALA, FL, 34482, Ocala, FL 34482
$275,000

2 beds

|

2 baths

|

1,318 sq ft

|

House

5235 NW 33RD PL, OCALA, FL, 34482
Community: Ocala Preserve
Stone Creek 6606 SW 91ST CIR, OCALA, FL, 34481, Ocala, FL 34481
$299,000

2 beds

|

2 baths

|

1,706 sq ft

|

Townhouse

6606 SW 91ST CIR, OCALA, FL, 34481
Community: Stone Creek
Highlands Ridge 2877 S DRIFTWOOD CT, AVON PARK, FL, 3382..., Avon Park, FL 33825
$149,900

2 beds

|

2 baths

|

1,708 sq ft

|

Mobile Home

2877 S DRIFTWOOD CT, AVON PARK, FL, 3382...
Community: Highlands Ridge
On Top of the World 9480 SW 94TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$375,000

3 beds

|

3 baths

|

1,855 sq ft

|

House

9480 SW 94TH LOOP, OCALA, FL, 34481
Community: On Top of the World

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3,648 homes near Winter Garden
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