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241 Dillard Street
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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: 41
  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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Seller financing opportunity!!! 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 proud
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133 Park Avenue
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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: 27
  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
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100 Temple Grove Drive
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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. Previous Price: $1,100,000
  4. Last Price Change: 11/15/25
  5. Days On Market: 57
  6. Bedrooms: 4
  7. Baths: 3
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 4362
  10. Acreage: 0.69 acres
  11. Pool: No
  12. Spa/HotTub: Yes
  13. Waterfront: No
  14. 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
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515 Boyd Street
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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: 505
  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
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1669 Markel Drive
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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: 386
  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
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213 Tilden Street
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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: 11/20/25
  5. Days On Market: 150
  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
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40 Smith Street
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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: 29
  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
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351 Floral Drive
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Details for 351 Floral Drive, WINTER GARDEN, FL 34787
Single Family
  1. Price: $689,000.00
  2. Price sqft: $294.19 / sqft
  3. Previous Price: $705,000
  4. Last Price Change: 10/14/25
  5. Days On Market: 76
  6. Bedrooms: 3
  7. Baths: 2
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 2342
  10. Acreage: 0.29 acres
  11. Pool: No
  12. Waterfront: No
  13. Year Built: 1980
MLS#: O6343249
  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: COLDWELL BANKER RESIDENTIAL RE
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PRICE IMPROVEMENT Stunning Renovated Ranch on Prime Corner Lot in Historic Downtown Winter Garden Welcome to a prime corner lot property in Historic Downtown Winter Garden that perfectly blends mo
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459 Millwood Place
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Details for 459 Millwood Place, WINTER GARDEN, FL 34787
Single Family
  1. Price: $675,000.00
  2. Price sqft: $180.14 / sqft
  3. Previous Price: $699,999
  4. Last Price Change: 11/07/25
  5. Days On Market: 208
  6. Bedrooms: 4
  7. Baths: 3
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 3747
  10. Acreage: 0.16 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 2014
MLS#: O6306558
  1. County: ORANGE
  2. City: WINTER GARDEN
  3. Zipcode: 34787
  4. Subdivision: Covington Chase Ph 2a
  5. Elementary School: Dillard Street Elem
  6. Middle School: Lakeview Middle
  7. High School: Ocoee High
  8. Provided by: HOMEVEST REALTY
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One or more photo(s) has been virtually staged. Just in Time for Summer A Self Sustaining Paradise with Solar, Pool, Garden & More! Step into a home that offers not just warmth and comfort, but a
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1075 Chase Drive
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Details for 1075 Chase Drive, WINTER GARDEN, FL 34787
Single Family
  1. Price: $625,000.00
  2. Price sqft: $294.12 / sqft
  3. Days On Market: 108
  4. Bedrooms: 4
  5. Baths: 2
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 2125
  8. Acreage: 0.26 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 2015
MLS#: O6335675
  1. County: ORANGE
  2. City: WINTER GARDEN
  3. Zipcode: 34787
  4. Subdivision: Island Pointe Sub
  5. Elementary School: Dillard Street Elem
  6. Middle School: Lakeview Middle
  7. High School: Ocoee High
  8. Provided by: MAINFRAME REAL ESTATE
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Welcome to 1075 Chase Drive located in downtown Winter Garden, just minutes from the charm and energy of Plant Street. This rare, newer construction single story home offers a blend of modern comfort
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