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  1. School = Dillard Street Elem
Details for 241 Dillard Street, WINTER GARDEN, FL 34787
Single Family
  1. Price: $1,800,000.00
  2. Price sqft: $385.36 / sqft
  3. Days On Market: 16
  4. Bedrooms: 3
  5. Baths: 3
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 4671
  8. Acreage: 0.64 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 1953
MLS#: O6353975
  1. County: ORANGE
  2. City: WINTER GARDEN
  3. Zipcode: 34787
  4. Subdivision: J L Dillard Sub 3
  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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Welcome to a Once in a Lifetime Opportunity in the Heart of Downtown Winter Garden Nestled beneath the shade of enchanting oak trees, this stately residence sits proudly on a rare triple lot in one o
Details for 284 Donald Drive, WINTER GARDEN, FL 34787
Single Family
  1. Price: $1,650,000.00
  2. Price sqft: $368.30 / sqft
  3. Previous Price: $1,699,000
  4. Last Price Change: 11/03/25
  5. Days On Market: 113
  6. Bedrooms: 4
  7. Baths: 5
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 4480
  10. Acreage: 0.25 acres
  11. Pool: No
  12. Waterfront: No
  13. Year Built: 2025
MLS#: O6325831
  1. County: ORANGE
  2. City: WINTER GARDEN
  3. Zipcode: 34787
  4. Subdivision: Showalter 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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Welcome to your dream home in the heart of Winter Garden's Golf cart Community! This stunning 4 bedroom 4.5 baths residence offers a perfect blend of luxury and comfort, ideal for families and entert
Details for 133 Park Avenue, WINTER GARDEN, FL 34787
Townhome
  1. Price: $1,289,000.00
  2. Price sqft: $375.26 / sqft
  3. Days On Market: 3
  4. Bedrooms: 3
  5. Baths: 4
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3435
  8. Acreage: 0.03 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 2019
MLS#: G5103956
  1. County: ORANGE
  2. City: WINTER GARDEN
  3. Zipcode: 34787
  4. Subdivision: Park Placewinter Garden
  5. Elementary School: Dillard Street Elem
  6. Middle School: Lakeview Middle
  7. High School: West Orange High
  8. Provided by: ERA GRIZZARD REAL ESTATE
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Modern & Sleek Townhouse in the Winter Garden Historical District featuring high end details & quality finishes that you would expect to find in such a remarkable property. This stunning 3 level townh
Details for 100 Temple Grove Drive, WINTER GARDEN, FL 34787
Single Family
  1. Price: $1,050,000.00
  2. Price sqft: $240.72 / sqft
  3. Days On Market: 32
  4. Bedrooms: 4
  5. Baths: 3
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 4362
  8. Acreage: 0.69 acres
  9. Pool: No
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 1973
MLS#: NS1086151
  1. County: ORANGE
  2. City: WINTER GARDEN
  3. Zipcode: 34787
  4. Subdivision: Emerald Acres
  5. Elementary School: Dillard Street Elem
  6. Middle School: Lakeview Middle
  7. High School: West Orange High
  8. Provided by: ENGEL & VOLKERS NEW SMYRNA
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Welcome home to a true Winter Garden gem that perfectly blends modern comfort, timeless design, and small town charm. Nestled on a spacious private lot with no HOA, this beautifully expanded and reima
Details for 515 Boyd Street, WINTER GARDEN, FL 34787
Single Family
  1. Price: $900,000.00
  2. Price sqft: $188.21 / sqft
  3. Previous Price: $950,000
  4. Last Price Change: 10/18/25
  5. Days On Market: 481
  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 1669 Markel Drive, WINTER GARDEN, FL 34787
Single Family
  1. Price: $894,544.00
  2. Price sqft: $292.14 / sqft
  3. Previous Price: $859,000
  4. Last Price Change: 08/29/25
  5. Days On Market: 362
  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. NO HOA! FLAT, CLEARED, NO WETLANDS LOT IN WINTER GARDEN. This is the LAST vacant lot available in Hillcrest's established Winter Garden community across from McAllistair
Details for 524 Lakeview Avenue, WINTER GARDEN, FL 34787
Single Family
  1. Price: $890,000.00
  2. Price sqft: $321.88 / sqft
  3. Previous Price: $950,000
  4. Last Price Change: 10/25/25
  5. Days On Market: 134
  6. Bedrooms: 3
  7. Baths: 3
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 2765
  10. Acreage: 0.53 acres
  11. Pool: Yes
  12. Waterfront: No
  13. 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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One or more photo(s) has been virtually staged. ***new reduced price! ***move in before the holidays & take advantage of the lower interest rates! The sellers are motivated and ready for the next chap
Details for 213 Tilden Street, WINTER GARDEN, FL 34787
Single Family
  1. Price: $789,000.00
  2. Price sqft: $375.71 / sqft
  3. Previous Price: $795,000
  4. Last Price Change: 11/04/25
  5. Days On Market: 126
  6. Bedrooms: 4
  7. Baths: 2
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 2100
  10. Acreage: 0.27 acres
  11. Pool: No
  12. Waterfront: No
  13. 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 Middle
  7. High School: West Orange High
  8. Provided by: UNITED REALTY GROUP INC
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Located in the heart of DOWNTOWN WINTER GARDEN!! This beautifully renovated single story home combines charm with modern upgrades. Completely redesigned in 2021, this home showcase
Details for 753 Orange Belt Loop, WINTER GARDEN, FL 34787
Single Family
  1. Price: $775,000.00
  2. Price sqft: $200.16 / sqft
  3. Previous Price: $800,000
  4. Last Price Change: 11/04/25
  5. Days On Market: 87
  6. Bedrooms: 4
  7. Baths: 4
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 3872
  10. Acreage: 0.12 acres
  11. Pool: No
  12. Community Pool: Yes
  13. Waterfront: Yes
  14. Wateraccess: Yes
  15. Waterfront Type: Pond
  16. Year Built: 2020
MLS#: O6334032
  1. County: ORANGE
  2. City: WINTER GARDEN
  3. Zipcode: 34787
  4. Subdivision: Heritageplant Street
  5. Elementary School: Dillard Street Elem
  6. Middle School: Lakeview Middle
  7. High School: West Orange High
  8. Provided by: CENTURY 21 CARIOTI
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Waterfront Living Steps from Downtown Winter Garden Imagine starting your day with coffee on the porch, sunlight reflecting off the water, and the hum of downtown Winter Garden just minutes away
Details for 40 Smith Street, WINTER GARDEN, FL 34787
Single Family
  1. Price: $750,000.00
  2. Price sqft: $337.08 / sqft
  3. Days On Market: 4
  4. Bedrooms: 4
  5. Baths: 2
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 2225
  8. Acreage: 0.22 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 1923
MLS#: O6355801
  1. County: ORANGE
  2. City: WINTER GARDEN
  3. Zipcode: 34787
  4. Subdivision: G T Smith Sub
  5. Elementary School: Dillard Street Elem
  6. Middle School: Lakeview Middle
  7. High School: West Orange High
  8. Provided by: NATIONAL REAL ESTATE LLC
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Welcome home to 40 W Smith St. Step into a piece of Winter Garden's rich history with this captivating, charming historic home in the "golf district" in the heart of downtown Winter Garden. Nestled i