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Details for 284 Donald Drive, WINTER GARDEN, FL 34787
Single Family
  1. Price: $1,699,000.00
  2. Price sqft: $379.24 / sqft
  3. Previous Price: $1,770,000
  4. Last Price Change: 09/07/25
  5. Days On Market: 56
  6. Bedrooms: 4
  7. Baths: 5
  8. Garage / Parking Spaces: 1
  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
  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: $985,000.00
  2. Price sqft: $356.24 / sqft
  3. Previous Price: $1,050,000
  4. Last Price Change: 09/08/25
  5. Days On Market: 77
  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. Looking for a beautifully updated Craftsman style home with character on a lot that offers more than most? This Downtown Winter Garden property delivers
Details for 515 Boyd Street, WINTER GARDEN, FL 34787
Single Family
  1. Price: $950,000.00
  2. Price sqft: $198.66 / sqft
  3. Previous Price: $975,000
  4. Last Price Change: 08/23/25
  5. Days On Market: 424
  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 613 Sigler Drive, WINTER GARDEN, FL 34787
Single Family
  1. Price: $907,340.00
  2. Price sqft: $293.45 / sqft
  3. Days On Market: 65
  4. Bedrooms: 4
  5. Baths: 4
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3092
  8. Acreage: 0.07 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 2026
MLS#: O6323923
  1. County: ORANGE
  2. City: WINTER GARDEN
  3. Zipcode: 34787
  4. Subdivision: Lakeview Village Estates
  5. Elementary School: Dillard Street Elem
  6. Middle School: Lakeview Middle
  7. High School: West Orange High
  8. Provided by: NOVA REAL ESTATE SERVICES INC
  9. mfrmls
  10. DMCA Notice
Description
  1. Under Construction. Welcome to Lakeview Village Estates an exclusive new community by award winning Davila Homes, featuring just 40 homes that seamlessly blend timeless architecture, superior constru
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: 305
  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: $825,000.00
  2. Price sqft: $213.07 / sqft
  3. Days On Market: 30
  4. Bedrooms: 4
  5. Baths: 4
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3872
  8. Acreage: 0.12 acres
  9. Pool: No
  10. Community Pool: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Pond
  14. 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: $795,000.00
  2. Price sqft: $378.57 / sqft
  3. Days On Market: 69
  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 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 563 Copperdale Avenue, WINTER GARDEN, FL 34787
Single Family
  1. Price: $725,000.00
  2. Price sqft: $191.24 / sqft
  3. Previous Price: $732,900
  4. Last Price Change: 09/08/25
  5. Days On Market: 164
  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
  9. mfrmls
  10. DMCA Notice
Description
  1. One or more photos have been virtually staged. $25,000 below appraised value! Seller offering an additional $7000 towards rate buy down or closing costs. This 5 bedroom, 3 bathroom, lovely pool home
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: 09/06/25
  5. Days On Market: 242
  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 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: 09/08/25
  5. Days On Market: 126
  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