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  1. School = Dillard Street Elem
Details for 284 Donald Drive, WINTER GARDEN, FL 34787
Single Family
  1. Price: $1,699,000.00
  2. Price sqft: $379.24 / sqft
  3. Days On Market: 69
  4. Bedrooms: 4
  5. Baths: 5
  6. Garage / Parking Spaces: 1
  7. Bldg sqft: 4480
  8. Acreage: 0.25 acres
  9. Pool: No
  10. Waterfront: No
  11. 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
  9. mfrmls
  10. DMCA Notice
Description
  1. 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 524 Lakeview Avenue, WINTER GARDEN, FL 34787
Single Family
  1. Price: $950,000.00
  2. Price sqft: $343.58 / sqft
  3. Previous Price: $985,000
  4. Last Price Change: 09/18/25
  5. Days On Market: 89
  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
  9. mfrmls
  10. DMCA Notice
Description
  1. One or more photo(s) has been virtually staged. ***NEW LOWER PRICE*** Perfect home to enjoy the upcoming holidays! Are you looking for a beautifully updated Craftsman style home with character on a lo
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: 09/15/25
  5. Days On Market: 436
  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
  9. mfrmls
  10. DMCA Notice
Description
  1. 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: 317
  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
  9. mfrmls
  10. DMCA Notice
Description
  1. 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 753 Orange Belt Loop, WINTER GARDEN, FL 34787
Single Family
  1. Price: $810,000.00
  2. Price sqft: $209.19 / sqft
  3. Previous Price: $825,000
  4. Last Price Change: 09/18/25
  5. Days On Market: 42
  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
  9. mfrmls
  10. DMCA Notice
Description
  1. Discover waterfront living steps from downtown Winter Gardenin this beautifully appointed home, offeringpaid off solar power at closingfor energy savings from day one. From the inviting covered front
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: 09/20/25
  5. Days On Market: 81
  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
  9. mfrmls
  10. DMCA Notice
Description
  1. One of a kind home located in the heart of DOWNTOWN WINTER GARDEN!! This beautifully renovated single story home combines charm with modern upgrades. Completely redesigned in 2021,
Details for 313 Courtlea Park Drive, WINTER GARDEN, FL 34787
Single Family
  1. Price: $760,000.00
  2. Price sqft: $189.57 / sqft
  3. Days On Market: 33
  4. Bedrooms: 5
  5. Baths: 4
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 4009
  8. Acreage: 0.25 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 2006
MLS#: O6336875
  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: West Orange High
  8. Provided by: EXP REALTY LLC
  9. mfrmls
  10. DMCA Notice
Description
  1. This stunning 5 bedroom, 4 bathroom home at 313 Courtlea Park Dr in Winter Garden is priced below APPRAISED VALUE, offering exceptional value in one of Central Florida's most desirable communities. Lo
Details for 322 Apopka Street, WINTER GARDEN, FL 34787
Single Family
  1. Price: $709,000.00
  2. Price sqft: $330.23 / sqft
  3. Previous Price: $735,000
  4. Last Price Change: 09/13/25
  5. Days On Market: 254
  6. Bedrooms: 4
  7. Baths: 3
  8. Garage / Parking Spaces: 1
  9. Bldg sqft: 2147
  10. Acreage: 0.21 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 1956
MLS#: O6270533
  1. County: ORANGE
  2. City: WINTER GARDEN
  3. Zipcode: 34787
  4. Subdivision: Westlake Manor
  5. Elementary School: Dillard Street Elem
  6. Middle School: Lakeview Middle
  7. High School: West Orange High
  8. Provided by: SOUTHERN HERITAGE REALTY, INC
  9. mfrmls
  10. DMCA Notice
Description
  1. ***opportunity knocks*** come see this stunning 4 bedroom 2. 5 bathroom pool home nestled in the heart of the historic district of winter garden, florida. With sleek lines, large windows and minimalis
Details for 351 Floral Drive, WINTER GARDEN, FL 34787
Single Family
  1. Price: $705,000.00
  2. Price sqft: $301.03 / sqft
  3. Days On Market: 7
  4. Bedrooms: 3
  5. Baths: 2
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 2342
  8. Acreage: 0.29 acres
  9. Pool: No
  10. Waterfront: No
  11. 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
  9. mfrmls
  10. DMCA Notice
Description
  1. 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 modern luxury with sma
Details for 459 Millwood Place, WINTER GARDEN, FL 34787
Single Family
  1. Price: $699,999.00
  2. Price sqft: $186.82 / sqft
  3. Previous Price: $725,000
  4. Last Price Change: 09/10/25
  5. Days On Market: 138
  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
  9. mfrmls
  10. DMCA Notice
Description
  1. 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
Wade M. Berlin