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  1. School = Dillard
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: 52
  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
  7. High School: West Orange
  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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205 Surprise Drive
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Details for 205 Surprise Drive, WINTER GARDEN, FL 34787
Single Family
  1. Price: $1,300,000.00
  2. Price sqft: $461.16 / sqft
  3. Days On Market: 7
  4. Bedrooms: 3
  5. Baths: 3
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 2819
  8. Acreage: 0.75 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 1950
MLS#: O6365188
  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: RE/MAX PRIME PROPERTIES
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Discover an exceptional property in the heart of highly desirable GOLF CART DISTRICT of Winter Garden. Situated on an expansive four lot parcel totaling 3/4 of an acre, this unique estate offers unma
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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: 39
  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
  7. High School: West Orange
  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: 11/06/25
  5. Days On Market: 68
  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
  7. High School: West Orange
  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: 09/15/25
  5. Days On Market: 517
  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
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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: 398
  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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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: 09/22/25
  5. Days On Market: 162
  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
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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: $725,000.00
  2. Price sqft: $325.84 / sqft
  3. Previous Price: $750,000
  4. Last Price Change: 12/04/25
  5. Days On Market: 41
  6. Bedrooms: 4
  7. Baths: 2
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 2225
  10. Acreage: 0.22 acres
  11. Pool: No
  12. Waterfront: No
  13. 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
  7. High School: West Orange
  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: 87
  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
  7. High School: West Orange
  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: 10/01/25
  5. Days On Market: 219
  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
  7. High School: Ocoee
  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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Tropic Shores Realty - Crystal River
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Listings provided courtesy of The Hernando County Association of Realtors MLS.
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Datafeed Last updated on December 12, 2025 @ 12:00 am
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