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Winter Garden, FL 55+ active adult communities & homes for sale - Page 7

3,654 homes near Winter Garden

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4 rating (17 reviews) The Villages®
$100ks - $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
$100ks - $800ks
Sun City Center, Sun City Center, FL
Resale Only | 55+ age-restricted | Built 1961 - 2018 | 9,500 homes
4.2 rating (10 reviews) Stone Creek
$200ks - $500ks
Stone Creek, Ocala, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 3,800 homes
4.7 rating (18 reviews) Solivita
$300ks - $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
4.5 rating (11 reviews) Spruce Creek Country Club
$100ks - $400ks
Spruce Creek Country Club, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1996 - 2007 | 3,250 homes
Venetian Bay
$300ks - $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale | Age-targeted | Built 2004 - present | 1,561 homes
5 rating (2 reviews) Plantation at Leesburg
$100ks - $300ks
Plantation at Leesburg, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1987 - 2008 | 2,820 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
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.
3.6 rating (48 reviews) Latitude Margaritaville
$300ks - $800ks
Latitude Margaritaville, Daytona Beach, FL
Resale Only | 55+ age-restricted | Built 2017 - 2025 | 3,900 homes
5 rating (3 reviews) Stonecrest
$200ks - $500ks
Stonecrest, Summerfield, FL
New and Resale | 55+ age-restricted | Built 1990 - present | 2,200 homes
4.6 rating (5 reviews) Ocala Preserve
$100ks - $500ks
Ocala Preserve, Ocala, FL
New and Resale | 55+ age-restricted | Built 2014 - present | 1,800 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
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
5 rating (1 reviews) Ocala Palms
$200ks - $300ks
Ocala Palms, Ocala, FL
Resale Only | 55+ age-restricted | Built 1994 - 1997 | 1,076 homes
3.8 rating (4 reviews) Spruce Creek South
$100ks - $200ks
Spruce Creek South, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1989 - 1995 | 1,650 homes
5 rating (5 reviews) SummerGlen
$200ks - $400ks
SummerGlen, Ocala, FL
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,024 homes
Southshore Bay
$200ks - $500ks
Southshore Bay, Wimauma, FL
New and Resale | 55+ age-restricted | Built 2017 - present | 655 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.
4.7 rating (11 reviews) Valencia Lakes
$200ks - $700ks
Valencia Lakes, Wimauma, FL
Resale Only | 55+ age-restricted | Built 2005 - 2019 | 1,631 homes
5 rating (8 reviews) Royal Highlands
$200ks - $400ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 homes
5 rating (1 reviews) Del Webb Sunbridge
$400ks - $800ks
Del Webb Sunbridge, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 1,300 homes
4 rating (7 reviews) Tampa Bay Golf and Countr...
$200ks - $500ks
Tampa Bay Golf and Countr..., San Antonio, FL
Resale Only | 55+ age-restricted | Built 1994 - 2015 | 1,336 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
5 rating (7 reviews) Kings Ridge
$200ks - $400ks
Kings Ridge, Clermont, FL
Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 homes
3.8 rating (6 reviews) Trilogy® Orlando
$200ks - $500ks
Trilogy® Orlando, Groveland, FL
Resale Only | 55+ age-restricted | Built 2005 - 2022 | 1,500 homes
5 rating (3 reviews) Twin Lakes
$200ks - $600ks
Twin Lakes, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 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
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.
2.8 rating (6 reviews) Arlington Ridge
$200ks - $500ks
Arlington Ridge, Leesburg, FL
New and Resale | 55+ age-restricted | Built 2005 - present | 629 homes
Pelican Bay Daytona Beach
$100ks - $600ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 homes
4 rating (4 reviews) Lakes of Mount Dora
$300ks - $900ks
Lakes of Mount Dora, Mount Dora, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 950 homes
2.3 rating (6 reviews) Cherrywood
$100ks - $800ks
Cherrywood, Ocala, FL
Resale Only | 55+ age-restricted | Built 1996 - 2003 | 700 homes
4 rating (2 reviews) Harbor Hills Country Club
$300ks - $900ks
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
Pine Run Estates
$100ks - $200ks
Pine Run Estates, Ocala, FL
Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 homes
1 rating (1 reviews) Sullivan Ranch
$200ks - $500ks
Sullivan Ranch, Mount Dora, FL
Resale Only | 55+ age-restricted | Built 2005 - 2020 | 692 homes
3.6 rating (5 reviews) Heritage Hills
$200ks - $400ks
Heritage Hills, Clermont, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 1,154 homes
Mirada
$300ks - $500ks
Mirada, San Antonio, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 858 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 (1 reviews) Palm Cay
$100ks - $200ks
Palm Cay, Ocala, FL
Resale Only | 55+ age-restricted | Built 1985 - 1992 | 795 homes
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
5 rating (8 reviews) Pennbrooke Fairways
<$100k - $300ks
Pennbrooke Fairways, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 homes
4.8 rating (6 reviews) Highland Lakes
$100ks - $200ks
Highland Lakes, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
5 rating (1 reviews) Royal Harbor
$200ks - $800ks
Royal Harbor, Tavares, FL
Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 homes
Four Seasons at Orlando
$300ks - $600ks
Four Seasons at Orlando, Kissimmee, FL
New Construction | 55+ age-restricted | Built 2017 - present | 557 homes
12...3
New The Villages® 1088 GENNESSE LN, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$300,000

2 beds

|

2 baths

|

1,240 sq ft

|

House

1088 GENNESSE LN, THE VILLAGES, FL, 3216...
Community: The Villages®
New Oak Run 10841 SW 90TH CT, OCALA, FL, 34481, Ocala, FL 34481
$200,000

2 beds

|

2 baths

|

1,432 sq ft

|

House

10841 SW 90TH CT, OCALA, FL, 34481
Community: Oak Run
New The Villages® 2149 ESCOBAR AVE, THE VILLAGES, FL, 3215..., The Villages, FL 32159
$250,000

2 beds

|

2 baths

|

1,121 sq ft

|

Villa

2149 ESCOBAR AVE, THE VILLAGES, FL, 3215...
Community: The Villages®
New Stonecrest 17180 SE 115TH TERRACE RD, SUMMERFIELD, ..., Summerfield, FL 34491
$349,900

3 beds

|

2 baths

|

1,796 sq ft

|

House

17180 SE 115TH TERRACE RD, SUMMERFIELD, ...
Community: Stonecrest
New Heritage Hills 2888 SANDY CAY ST, CLERMONT, FL, 34711, Clermont, FL 34711
$559,000

4 beds

|

3 baths

|

2,562 sq ft

|

House

2888 SANDY CAY ST, 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
New Traditions at Lake Ruby 3832 TRADITIONS BLVD, WINTER HAVEN, FL, ..., Winter Haven, FL 33884
$250,000

3 beds

|

2 baths

|

2,109 sq ft

|

House

3832 TRADITIONS BLVD, WINTER HAVEN, FL, ...
New Lakeside Landings 10396 SILVER MAPLE AVE, OXFORD, FL, 3448..., Oxford, FL 34484
$339,000

3 beds

|

2 baths

|

1,658 sq ft

|

House

10396 SILVER MAPLE AVE, OXFORD, FL, 3448...
Community: Lakeside Landings
New On Top of the World 8702 SW 94TH ST A, OCALA, FL, 34481, Ocala, FL 34481
$134,900

2 beds

|

2 baths

|

1,369 sq ft

|

Villa

8702 SW 94TH ST A, OCALA, FL, 34481
Community: On Top of the World
Pelican Bay Daytona Beach 107 GREY WIDGEON CT, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119
$265,000

2 beds

|

3 baths

|

1,657 sq ft

|

House

107 GREY WIDGEON CT, DAYTONA BEACH, FL, ...
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.
Summer Trees 120 CROOKED PINE RD, PORT ORANGE, FL, 32..., Port Orange, FL 32128
$304,995

2 beds

|

2 baths

|

1,245 sq ft

|

House

120 CROOKED PINE RD, PORT ORANGE, FL, 32...
Community: Summer Trees
Latitude Margaritaville 852 CORAL REEF WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$539,000

2 beds

|

3 baths

|

1,748 sq ft

|

House

852 CORAL REEF WAY, DAYTONA BEACH, FL, 3...
Latitude Margaritaville 303 LATITUDE DR, DAYTONA BEACH, FL, 3212..., Daytona Beach, FL 32124
$397,500

2 beds

|

2 baths

|

1,308 sq ft

|

House

303 LATITUDE DR, DAYTONA BEACH, FL, 3212...
Latitude Margaritaville 825 MARGARITAVILLE AVE, DAYTONA BEACH, F..., Daytona Beach, FL 32124
$549,900

2 beds

|

3 baths

|

1,748 sq ft

|

House

825 MARGARITAVILLE AVE, DAYTONA BEACH, F...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Fountain View 1356 FOUNTAIN VIEW ST, ORMOND BEACH, FL,..., Ormond Beach, FL 32174
$415,990

4 beds

|

3 baths

|

2,336 sq ft

|

House

1356 FOUNTAIN VIEW ST, ORMOND BEACH, FL,...
Community: Fountain View
Spruce Creek Preserve 13908 SW 114TH CIR, DUNNELLON, FL, 34432, Dunnellon, FL 34432
$274,000

3 beds

|

2 baths

|

1,546 sq ft

|

House

13908 SW 114TH CIR, DUNNELLON, FL, 34432
Sun City Center 201 STONEHOUSE CT, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$265,000

2 beds

|

2 baths

|

1,527 sq ft

|

House

201 STONEHOUSE CT, SUN CITY CENTER, FL, ...
Community: Sun City Center
Valencia Lakes 5056 RUBY FLATS DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$825,000

2 beds

|

3 baths

|

2,795 sq ft

|

House

5056 RUBY FLATS DR, WIMAUMA, FL, 33598
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.
Oak Run 10978 SW 83RD AVE, OCALA, FL, 34481, Ocala, FL 34481
$209,900

2 beds

|

2 baths

|

1,224 sq ft

|

House

10978 SW 83RD AVE, OCALA, FL, 34481
Community: Oak Run
Trilogy® Orlando 108 MIST FLOWER LN, GROVELAND, FL, 34736, Groveland, FL 34736
$450,000

2 beds

|

2 baths

|

1,900 sq ft

|

House

108 MIST FLOWER LN, GROVELAND, FL, 34736
Community: Trilogy® Orlando
Sun City Center 504 LIME TREE CT, SUN CITY CENTER, FL, 3..., Sun City Center, FL 33573
$269,900

2 beds

|

2 baths

|

1,634 sq ft

|

House

504 LIME TREE CT, SUN CITY CENTER, FL, 3...
Community: Sun City Center
Sun City Center 2422 E DEL WEBB BLVD, SUN CITY CENTER, F..., Sun City Center, FL 33573
$332,000

3 beds

|

2 baths

|

1,737 sq ft

|

House

2422 E DEL WEBB BLVD, SUN CITY CENTER, F...
Community: Sun City Center
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Summit Chase Villas 12449 ORANGEWOOD CIR 17, TAVARES, FL, 32..., Tavares, FL 32778
$179,000

2 beds

|

2 baths

|

918 sq ft

|

Condo

12449 ORANGEWOOD CIR 17, TAVARES, FL, 32...
Community: Summit Chase Villas
Summit Greens 2197 CALEDONIAN ST, CLERMONT, FL, 34711, Clermont, FL 34711
$345,000

3 beds

|

2 baths

|

1,703 sq ft

|

House

2197 CALEDONIAN ST, CLERMONT, FL, 34711
Community: Summit Greens
Sun City Center 1010 N PEBBLE BEACH BLVD, SUN CITY CENTE..., Sun City Center, FL 33573
$139,900

2 beds

|

1 baths

|

899 sq ft

|

Townhouse

1010 N PEBBLE BEACH BLVD, SUN CITY CENTE...
Community: Sun City Center
Venetian Bay 3615 MARISOL CT, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168
$525,000

3 beds

|

2 baths

|

1,764 sq ft

|

House

3615 MARISOL CT, NEW SMYRNA BEACH, FL, 3...
Community: Venetian Bay
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.
Kings Ridge 4124 KINGSLEY ST, CLERMONT, FL, 34711, Clermont, FL 34711
$367,000

2 beds

|

2 baths

|

1,802 sq ft

|

House

4124 KINGSLEY ST, CLERMONT, FL, 34711
Community: Kings Ridge
Scottish Highlands 2218 ORKNEY DR, LEESBURG, FL, 34788, Leesburg, FL 34788
$229,000

2 beds

|

2 baths

|

1,500 sq ft

|

House

2218 ORKNEY DR, LEESBURG, FL, 34788
Community: Scottish Highlands
The Villages® 403 MCLEOD LN, THE VILLAGES, FL, 32162, The Villages, FL 32162
$387,000

3 beds

|

2 baths

|

1,512 sq ft

|

House

403 MCLEOD LN, THE VILLAGES, FL, 32162
Community: The Villages®
Stone Creek 7271 SW 95TH CT, OCALA, FL, 34481, Ocala, FL 34481
$372,000

3 beds

|

2 baths

|

1,958 sq ft

|

House

7271 SW 95TH CT, OCALA, FL, 34481
Community: Stone Creek
The Villages® 1712 CARRERA DR, THE VILLAGES, FL, 32159, The Villages, FL 32159
$335,000

3 beds

|

2 baths

|

1,440 sq ft

|

House

1712 CARRERA DR, THE VILLAGES, FL, 32159
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Sun City Center 110 & 112 GLOUCESTER BLVD 110 & 112, SUN..., Sun City Center, FL 33573
$359,900

2 beds

|

2 baths

|

1,104 sq ft

|

Halfplex

110 & 112 GLOUCESTER BLVD 110 & 112, SUN...
Community: Sun City Center
Lake Henry Estates 558 PINNACLE DR, HAINES CITY, FL, 33844, Haines City, FL 33844
$253,000

2 beds

|

2 baths

|

1,273 sq ft

|

House

558 PINNACLE DR, HAINES CITY, FL, 33844
Community: Lake Henry Estates
Traditions at Lake Ruby 2708 ATTWATER LOOP, WINTER HAVEN, FL, 33..., Winter Haven, FL 33884
$269,999

3 beds

|

2 baths

|

1,561 sq ft

|

House

2708 ATTWATER LOOP, WINTER HAVEN, FL, 33...
Kings Ridge 3828 AVON CT, CLERMONT, FL, 34711, Clermont, FL 34711
$409,000

3 beds

|

2 baths

|

2,026 sq ft

|

House

3828 AVON CT, CLERMONT, FL, 34711
Community: Kings Ridge
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.
The Villages® 3283 CANDLEBROOK ST, THE VILLAGES, FL, 3..., The Villages, FL 32162
$278,750

2 beds

|

2 baths

|

1,142 sq ft

|

House

3283 CANDLEBROOK ST, THE VILLAGES, FL, 3...
Community: The Villages®
The Lakes at Harmony 3464 SAGEBRUSH ST, HARMONY, FL, 34773, Harmony, FL 34773
$315,000

2 beds

|

2 baths

|

1,404 sq ft

|

House

3464 SAGEBRUSH ST, HARMONY, FL, 34773
SummerGlen 1679 SW 156TH LN, OCALA, FL, 34473, Ocala, FL 34473
$249,900

3 beds

|

2 baths

|

House

1679 SW 156TH LN, OCALA, FL, 34473
Community: SummerGlen
Arlington Ridge 27118 ROANOKE DR 516, LEESBURG, FL, 3474..., Leesburg, FL 34748
$379,900

3 beds

|

2 baths

|

1,713 sq ft

|

House

27118 ROANOKE DR 516, LEESBURG, FL, 3474...
Community: Arlington Ridge
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Spruce Creek Country Club 14160 SE 85TH AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$236,000

2 beds

|

2 baths

|

1,238 sq ft

|

Villa

14160 SE 85TH AVE, SUMMERFIELD, FL, 3449...
Venetian Bay 3605 ROMEA CIR, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$295,000

2 beds

|

3 baths

|

1,664 sq ft

|

Townhouse

3605 ROMEA CIR, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay

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