Searching on:
  1. School = Dillard Street Elem
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: $1,650,000.00
  2. Price sqft: $368.30 / sqft
  3. Previous Price: $1,699,000
  4. Last Price Change: 09/25/25
  5. Days On Market: 81
  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
Request more information about this listing.
524 Lakeview Avenue
Virtual Tour
More Like This
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: 09/19/25
  5. Days On Market: 101
  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. ***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
Listing Details and 63 Additional Pictures
Request more information about this listing.
515 Boyd Street
More Like This
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: 448
  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
Request more information about this listing.
1669 Markel Drive
Virtual Tour
New Construction
More Like This
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: 329
  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
  9. mfrmls
  10. DMCA Notice
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
Listing Details and 13 Additional Pictures
Request more information about this listing.
753 Orange Belt Loop
Virtual Tour
Green Listing
More Like This
Details for 753 Orange Belt Loop, Winter Garden, FL 34787
Single Family
  1. Price: $800,000.00
  2. Price sqft: $206.61 / sqft
  3. Previous Price: $810,000
  4. Last Price Change: 09/26/25
  5. Days On Market: 55
  6. Bedrooms: 4
  7. Baths: 4
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 3872
  10. Acreage: 0.12 acres
  11. Pool: Yes
  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: 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
Request more information about this listing.
753 Orange Belt Loop
Virtual Tour
Green Listing
Reduced
More Like This
Details for 753 Orange Belt Loop, WINTER GARDEN, FL 34787
Single Family
  1. Price: $800,000.00
  2. Price sqft: $206.61 / sqft
  3. Previous Price: $810,000
  4. Last Price Change: 10/02/25
  5. Days On Market: 54
  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
  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
Request more information about this listing.
205 Woodland Street
More Like This
Details for 205 Woodland Street, WINTER GARDEN, FL 34787
Single Family
  1. Price: $799,000.00
  2. Price sqft: $264.31 / sqft
  3. Days On Market: 87
  4. Bedrooms: 3
  5. Baths: 2
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3023
  8. Acreage: 0.27 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 1961
MLS#: G5099379
  1. County: ORANGE
  2. City: WINTER GARDEN
  3. Zipcode: 34787
  4. Subdivision: Annie L Berry Sub
  5. Elementary School: Dillard Street Elem
  6. Middle School: Lakeview
  7. High School: West Orange
  8. Provided by: COLDWELL BANKER HUBBARD HANSEN
  9. mfrmls
  10. DMCA Notice
One or more photo(s) has been virtually staged. Welcome to this beautifully maintained 3 bedroom, 2 bathroom ranch style home, ideally located within a 6 minute walk to historic downtown Winter Garden
Listing Details and 57 Additional Pictures
Request more information about this listing.
213 Tilden Street
Virtual Tour
More Like This
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: 09/22/25
  5. Days On Market: 93
  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
  7. High School: West Orange
  8. Provided by: UNITED REALTY GROUP INC
  9. mfrmls
  10. DMCA Notice
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,
Listing Details and 39 Additional Pictures
Request more information about this listing.
322 Apopka Street
Virtual Tour
More Like This
Details for 322 Apopka Street, WINTER GARDEN, FL 34787
Single Family
  1. Price: $709,000.00
  2. Price sqft: $330.23 / sqft
  3. Days On Market: 266
  4. Bedrooms: 4
  5. Baths: 3
  6. Garage / Parking Spaces: 1
  7. Bldg sqft: 2147
  8. Acreage: 0.21 acres
  9. Pool: Yes
  10. Waterfront: No
  11. 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
  7. High School: West Orange
  8. Provided by: SOUTHERN HERITAGE REALTY, INC
  9. mfrmls
  10. DMCA Notice
***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
Listing Details and 32 Additional Pictures
Request more information about this listing.
351 Floral Drive
Virtual Tour
More Like This
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: 19
  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
  7. High School: West Orange
  8. Provided by: COLDWELL BANKER RESIDENTIAL RE
  9. mfrmls
  10. DMCA Notice
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
Listing Details and 33 Additional Pictures
Request more information about this listing.