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  1. School = Dillard Street Elem
284 Donald Drive
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Adult Community
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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: 08/05/25
  5. Days On Market: 61
  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
  7. High School: West Orange
  8. Provided by: HOMEVEST REALTY
  9. Provided through
  10. DMCA Notice
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
Listing Details and 55 Additional Pictures
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284 Donald Drive
Virtual Tour
New Construction
Adult Community
More Like This
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: 08/06/25
  5. Days On Market: 61
  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
  7. High School: West Orange
  8. Provided by: HOMEVEST REALTY
  9. mfrmls
  10. DMCA Notice
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
Listing Details and 55 Additional Pictures
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524 Lakeview Avenue
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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: 07/12/25
  5. Days On Market: 82
  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
  7. High School: West Orange
  8. Provided by: HOMEVEST REALTY
  9. Provided through
  10. DMCA Notice
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
Listing Details and 63 Additional Pictures
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524 Lakeview Avenue
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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: 07/19/25
  5. Days On Market: 81
  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
  7. High School: West Orange
  8. Provided by: HOMEVEST REALTY
  9. mfrmls
  10. DMCA Notice
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
Listing Details and 63 Additional Pictures
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515 Boyd Street
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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: 08/15/25
  5. Days On Market: 429
  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
  7. High School: West Orange
  8. Provided by: HOMEVEST REALTY
  9. Provided through
  10. DMCA Notice
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
Listing Details and 39 Additional Pictures
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515 Boyd Street
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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: 08/21/25
  5. Days On Market: 428
  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
  7. High School: West Orange
  8. Provided by: HOMEVEST REALTY
  9. mfrmls
  10. DMCA Notice
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
Listing Details and 39 Additional Pictures
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613 Sigler Drive
New Construction
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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: 69
  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
  7. High School: West Orange
  8. Provided by: NOVA REAL ESTATE SERVICES INC
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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
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1669 Markel Drive
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New Construction
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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: 309
  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
  7. High School: Ocoee
  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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753 Orange Belt Loop
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Green Listing
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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: 35
  4. Bedrooms: 4
  5. Baths: 4
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3872
  8. Acreage: 0.12 acres
  9. Pool: Yes
  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: Heritage/plant Street
  5. Elementary School: Dillard Street Elem
  6. Middle School: Lakeview
  7. High School: West Orange
  8. Provided by: CENTURY 21 CARIOTI
  9. Provided through
  10. DMCA Notice
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
Listing Details and 48 Additional Pictures
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753 Orange Belt Loop
Virtual Tour
Green Listing
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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: 34
  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
  7. High School: West Orange
  8. Provided by: CENTURY 21 CARIOTI
  9. mfrmls
  10. DMCA Notice
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
Listing Details and 48 Additional Pictures
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Tropic Shores Realty - Crystal River
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Listing Data ©2025 Greater Fort Lauderdale REALTORS®
Listings provided courtesy of The Hernando County Association of Realtors MLS.
Listing Data ©2025 REALTOR® Association of Citrus County
Listing Data ©2025 Royal Palm Coast Realtor® Association
The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Display of MLS data is usually deemed reliable but is NOT guaranteed accurate.
Datafeed Last updated on September 14, 2025 @ 12:00 am
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