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  1. School = Dillard Street Elem
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: 39
  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
  7. High School: West Orange
  8. Provided by: SERHANT
  9. Provided through
  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 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: 20
  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
  7. High School: West Orange
  8. Provided by: HOMEVEST REALTY
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One or more photo(s) has been virtually staged. Historic Downtown Winter Garden Craftsman Where Timeless Charm Meets Modern Living Discover a rare opportunity to own a beautifully preserved piece of
Details for 403 Courtlea Creek Drive, Winter Garden, FL 34787
Single Family
  1. Price: $950,000.00
  2. Price sqft: $217.09 / sqft
  3. Days On Market: 11
  4. Bedrooms: 5
  5. Baths: 3
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 4376
  8. Acreage: 0.33 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 1996
MLS#: O6323876
  1. County: ORANGE
  2. City: Winter Garden
  3. Zipcode: 34787
  4. Subdivision: Courtlea Oaks Ph 01a
  5. Elementary School: Dillard Street Elem
  6. Middle School: Lakeview
  7. High School: West Orange
  8. Provided by: REAL BROKER, LLC
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Welcome to Courtlea Oaks, nestled in the heart of downtown Winter Garden! This charming pool home features 5 bedrooms, 3 full bathrooms, and a framed, unfinished 408 sq. ft. bonus room upstairsready f
Details for 205 Trail Bridge Court, Winter Garden, FL 34787
Single Family
  1. Price: $849,000.00
  2. Price sqft: $235.44 / sqft
  3. Previous Price: $875,000
  4. Last Price Change: 06/20/25
  5. Days On Market: 27
  6. Bedrooms: 3
  7. Baths: 3
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 3606
  10. Acreage: 0.30 acres
  11. Pool: No
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: Pond
  15. 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
  7. High School: West Orange
  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 205 Woodland Street, Winter Garden, FL 34787
Single Family
  1. Price: $799,000.00
  2. Price sqft: $264.31 / sqft
  3. Days On Market: 5
  4. Bedrooms: 3
  5. Baths: 2
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3023
  8. Acreage: 0.27 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 1961
MLS#: G5099379
  1. County: ORANGE
  2. City: Winter Garden
  3. Zipcode: 34787
  4. Subdivision: Annie L Berry Sub
  5. Elementary School: Dillard Street Elem
  6. Middle School: Lakeview
  7. High School: West Orange
  8. Provided by: COLDWELL BANKER HUBBARD HANSEN
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One or more photo(s) has been virtually staged. Welcome to this beautifully maintained 3 bedroom, 2 bathroom ranch style home, ideally located within a 6 minute walk to historic downtown Winter Garden
Details for 213 Tilden Street, Winter Garden, FL 34787
Single Family
  1. Price: $795,000.00
  2. Price sqft: $378.57 / sqft
  3. Days On Market: 12
  4. Bedrooms: 4
  5. Baths: 2
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 2100
  8. Acreage: 0.27 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 1972
MLS#: O6321806
  1. County: ORANGE
  2. City: Winter Garden
  3. Zipcode: 34787
  4. Subdivision: Westlake Manor 1st Add
  5. Elementary School: Dillard Street Elem
  6. Middle School: Lakeview
  7. High School: West Orange
  8. Provided by: UNITED REALTY GROUP INC
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One of a kind 4 Bedroom home located in the heart of HISTORIC DOWNTOWN WINTER GARDEN. Walk to Plant Street!! This beautifully renovated single story home combines charm with modern upgrades. Com
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: 06/03/25
  5. Days On Market: 107
  6. Bedrooms: 5
  7. Baths: 3
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 3791
  10. Acreage: 0.25 acres
  11. Pool: Yes
  12. Community Pool: 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
  7. High School: Ocoee
  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
Details for 336 Courtlea Park Drive, Winter Garden, FL 34787
Single Family
  1. Price: $699,000.00
  2. Price sqft: $194.82 / sqft
  3. Days On Market: 4
  4. Bedrooms: 4
  5. Baths: 4
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 3588
  8. Acreage: 0.29 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 2006
MLS#: V4943730
  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
  7. High School: West Orange
  8. Provided by: LOKATION
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You need space? Step into this spacious Taylor Morrison home situated by the West Orange Trail, in the Golf Cart District, and just a few miles away from the shopping and restaurants in Historic Downt
Details for 724 Grassy Stone Drive, Winter Garden, FL 34787
Single Family
  1. Price: $665,900.00
  2. Price sqft: $203.45 / sqft
  3. Days On Market: 8
  4. Bedrooms: 4
  5. Baths: 3
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3273
  8. Acreage: 0.29 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2014
MLS#: O6316657
  1. County: ORANGE
  2. City: Winter Garden
  3. Zipcode: 34787
  4. Subdivision: Covington Chase Ph 2c
  5. Elementary School: Dillard Street Elem
  6. Middle School: Lakeview
  7. High School: Ocoee
  8. Provided by: ERA GRIZZARD REAL ESTATE
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This stunning 4 bedroom, 3 bathroom home in the sought after Winter Garden neighborhood offers a perfect combination of modern upgrades and timeless charm. Situated on a spacious 0.29 acre lot in a pe
Details for 101 Traditions Drive, Winter Garden, FL 34787
Single Family
  1. Price: $570,000.00
  2. Price sqft: $63.08 / sqft
  3. Days On Market: 7
  4. Bedrooms: 4
  5. Baths: 2
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 9036
  8. Acreage: 0.21 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 2001
MLS#: O6324620
  1. County: ORANGE
  2. City: Winter Garden
  3. Zipcode: 34787
  4. Subdivision: Traditions Sub
  5. Elementary School: Dillard Street Elem
  6. Middle School: Lakeview
  7. High School: West Orange
  8. Provided by: COMPASS FLORIDA LLC
  9. Provided through
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Welcome to 101 Traditions Driveyour charming slice of Winter Garden living just minutes from Historic Plant Street! This beautifully maintained 4 bedroom, 2 bathroom home offers the perfect blend of c

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