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  1. School = Dillard Street Elem
Details for 214 Woodland Street, WINTER GARDEN, FL 34787
Single Family
  1. Price: $1,990,000.00
  2. Price sqft: $525.48 / sqft
  3. Previous Price: $2,200,000
  4. Last Price Change: 06/14/25
  5. Days On Market: 210
  6. Bedrooms: 4
  7. Baths: 2
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 3787
  10. Acreage: 0.86 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 1925
MLS#: G5090037
  1. County: ORANGE
  2. City: WINTER GARDEN
  3. Zipcode: 34787
  4. Subdivision: Fries Winter Garden
  5. Elementary School: Dillard Street Elem
  6. Middle School: Lakeview Middle
  7. High School: West Orange High
  8. Provided by: KELLER WILLIAMS ELITE PARTNERS III REALTY
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Calling all Investors and Developers or anyone looking for a GREAT location to call home. Located in the heart of Downtown Winter Garden, this property offers a goldmine of opportunity for those looki
Details for 108 Stanton Estates Circle, WINTER GARDEN, FL 34787
Single Family
  1. Price: $1,565,000.00
  2. Price sqft: $261.49 / sqft
  3. Days On Market: 26
  4. Bedrooms: 4
  5. Baths: 4
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 5985
  8. Acreage: 0.29 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2019
MLS#: O6310710
  1. County: ORANGE
  2. City: WINTER GARDEN
  3. Zipcode: 34787
  4. Subdivision: Stanton Estates
  5. Elementary School: Dillard Street Elem
  6. Middle School: Lakeview Middle
  7. High School: West Orange High
  8. Provided by: SERHANT
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  10. DMCA Notice
Welcome to 108 Stanton Estates Circle, a beautifully crafted 4 bedroom, 4 bath pool home offering over 4,200 square feet of refined living in the heart of one of Winter Gardens most charming communiti
Details for 703 Valencia Shores Drive, WINTER GARDEN, FL 34787
Single Family
  1. Price: $1,325,000.00
  2. Price sqft: $256.44 / sqft
  3. Days On Market: 101
  4. Bedrooms: 4
  5. Baths: 3
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 5167
  8. Acreage: 1.25 acres
  9. Pool: No
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: Lake Front
  13. Year Built: 1980
MLS#: O6288347
  1. County: ORANGE
  2. City: WINTER GARDEN
  3. Zipcode: 34787
  4. Subdivision: Valencia Shores Rep
  5. Elementary School: Dillard Street Elem
  6. Middle School: Lakeview Middle
  7. High School: West Orange High
  8. Provided by: BHHS FLORIDA REALTY
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Wow! Lakefront home on Lake Apopka in the Golf Cart District in Winter Garden! Hurry to see this home with over 1.25 acres of property located on Lake Apopka, known for it's trophy size bass fishing!
Details for 524 Lakeview Avenue, WINTER GARDEN, FL 34787
Single Family
  1. Price: $1,050,000.00
  2. Price sqft: $379.75 / sqft
  3. Days On Market: 7
  4. Bedrooms: 3
  5. Baths: 3
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 2765
  8. Acreage: 0.53 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 1928
MLS#: O6320452
  1. County: ORANGE
  2. City: WINTER GARDEN
  3. Zipcode: 34787
  4. Subdivision: Pleasant Park
  5. Elementary School: Dillard Street Elem
  6. Middle School: Lakeview Middle
  7. High School: West Orange High
  8. Provided by: HOMEVEST REALTY
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Historic Downtown Winter Garden Craftsman Where Timeless Charm Meets Modern Living Discover a rare opportunity to own a beautifully preserved piece of Winter Garden history in the heart of the vibra
Details for 141 S. Park Ave, WINTER GARDEN, FL 34787
Townhome
  1. Price: $975,900.00
  2. Price sqft: $331.60 / sqft
  3. Previous Price: $999,500
  4. Last Price Change: 06/25/25
  5. Days On Market: 38
  6. Bedrooms: 3
  7. Baths: 4
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 2943
  10. Acreage: 0.02 acres
  11. Pool: No
  12. Waterfront: No
  13. Year Built: 2019
MLS#: O6312178
  1. County: ORANGE
  2. City: WINTER GARDEN
  3. Zipcode: 34787
  4. Subdivision: Park Place At Winter Garden
  5. Elementary School: Dillard Street Elem
  6. Middle School: Lakeview Middle
  7. High School: West Orange High
  8. Provided by: CORCORAN PREMIER REALTY
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Live in DT Winter Garden where vibes run high. This townhome is in the heart of Downtown Winter Garden, literally steps from the Crooked Can Brewery, Market to Table, and the farmers market every Sat
Details for 515 Boyd Street, WINTER GARDEN, FL 34787
Single Family
  1. Price: $975,000.00
  2. Price sqft: $203.89 / sqft
  3. Previous Price: $999,000
  4. Last Price Change: 06/17/25
  5. Days On Market: 354
  6. Bedrooms: 5
  7. Baths: 4
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 4782
  10. Acreage: 0.37 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 1957
MLS#: O6222919
  1. County: ORANGE
  2. City: WINTER GARDEN
  3. Zipcode: 34787
  4. Subdivision: Winter Garden Shores Rep
  5. Elementary School: Dillard Street Elem
  6. Middle School: Lakeview Middle
  7. High School: West Orange High
  8. Provided by: HOMEVEST REALTY
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One or more photo(s) has been virtually staged. Discover the charm and convenience of luxurious living in this stunning 5 bedroom, 3 bathroom home, perfectly located in the heart of downtown Winter Ga
Details for 205 Trail Bridge Court, WINTER GARDEN, FL 34787
Single Family
  1. Price: $875,000.00
  2. Price sqft: $242.65 / sqft
  3. Days On Market: 14
  4. Bedrooms: 3
  5. Baths: 3
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3606
  8. Acreage: 0.30 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 2003
MLS#: O6319154
  1. County: ORANGE
  2. City: WINTER GARDEN
  3. Zipcode: 34787
  4. Subdivision: Courtlea Oaks Ph 02b
  5. Elementary School: Dillard Street Elem
  6. Middle School: Lakeview Middle
  7. High School: West Orange High
  8. Provided by: HAMLIN REALTY
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WELCOME HOME to 205 Trail Bridge Court, a beautiful 3 bed, 2.5 bath custom home in the highly sought after Courtlea Oaks neighborhood of Winter Garden. Located on a quiet cul de sac in the golf cart d
Details for 1669 Markel Drive, WINTER GARDEN, FL 34787
Single Family
  1. Price: $859,000.00
  2. Price sqft: $280.54 / sqft
  3. Previous Price: $1,200,000
  4. Last Price Change: 02/19/25
  5. Days On Market: 235
  6. Bedrooms: 3
  7. Baths: 4
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 3062
  10. Acreage: 0.48 acres
  11. Pool: No
  12. Waterfront: No
  13. Year Built: 2025
MLS#: O6256295
  1. County: ORANGE
  2. City: WINTER GARDEN
  3. Zipcode: 34787
  4. Subdivision: Hillcrest
  5. Elementary School: Dillard Street Elem
  6. Middle School: Lakeview Middle
  7. High School: Ocoee High
  8. Provided by: Q BOUTIQUE SPECIALTY REALTY INC
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Pre Construction. To be built. Pre Construction! Easy as 1, 2, 3 purchase the lot, meet with the builder, and finance the lot and construction in one easy purchase. Customize this lovely three bed,
Details for 405 Courtlea Park Drive, WINTER GARDEN, FL 34787
Single Family
  1. Price: $790,000.00
  2. Price sqft: $220.06 / sqft
  3. Days On Market: 27
  4. Bedrooms: 4
  5. Baths: 4
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 3590
  8. Acreage: 0.25 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 2007
MLS#: O6315444
  1. County: ORANGE
  2. City: WINTER GARDEN
  3. Zipcode: 34787
  4. Subdivision: Greystone Ph 01
  5. Elementary School: Dillard Street Elem
  6. Middle School: Lakeview Middle
  7. High School: Ocoee High
  8. Provided by: WINTER GARDEN REAL ESTATE
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Welcome to 405 Courtlea Park Drive, a beautifully updated and meticulously maintained home in the highly desirable Courtlea Park community of Winter Garden. Ideally located near the West Orange Trail,
Details for 563 Copperdale Avenue, WINTER GARDEN, FL 34787
Single Family
  1. Price: $732,900.00
  2. Price sqft: $193.33 / sqft
  3. Previous Price: $752,900
  4. Last Price Change: 06/23/25
  5. Days On Market: 94
  6. Bedrooms: 5
  7. Baths: 3
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 3791
  10. Acreage: 0.25 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: No
  14. Year Built: 2013
MLS#: O6293957
  1. County: ORANGE
  2. City: WINTER GARDEN
  3. Zipcode: 34787
  4. Subdivision: Covington Chase Ph 2b
  5. Elementary School: Dillard Street Elem
  6. Middle School: Lakeview Middle
  7. High School: Ocoee High
  8. Provided by: KELLER WILLIAMS CLASSIC
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This 5 bedroom, 3 bathroom lovely pool home is ready for a new family to make lasting memories! Upon arriving at this wonderful home, you will be welcomed by the gorgeous pavers in the driveway and ta