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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: 83
  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: 38
  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: 70
  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: 99
  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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417 Main Street
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Details for 417 Main Street, WINTER GARDEN, FL 34787
Single Family
  1. Price: $775,000.00
  2. Price sqft: $254.93 / sqft
  3. Days On Market: 54
  4. Bedrooms: 3
  5. Baths: 3
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3040
  8. Acreage: 0.20 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 2019
MLS#: O6361513
  1. County: ORANGE
  2. City: WINTER GARDEN
  3. Zipcode: 34787
  4. Subdivision: Vinings Add Winter Garden
  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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Experience the perfect blend of historic charm and modern comfort in this home nestled in the sought after golf cart district of Downtown Winter Garden. This residence captures the character of the hi
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1474 Juniper Hammock Street
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Details for 1474 Juniper Hammock Street, WINTER GARDEN, FL 34787
Single Family
  1. Price: $675,000.00
  2. Price sqft: $155.07 / sqft
  3. Days On Market: 6
  4. Bedrooms: 5
  5. Baths: 4
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 4353
  8. Acreage: 0.20 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 2020
MLS#: O6369501
  1. County: ORANGE
  2. City: WINTER GARDEN
  3. Zipcode: 34787
  4. Subdivision: Mcallister Lndg
  5. Elementary School: Dillard Street Elem
  6. Middle School: Legacy
  7. High School: Ocoee
  8. Provided by: COLDWELL BANKER RESIDENTIAL RE
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One or more photo(s) has been virtually staged. Stunning and spacious Winter Garden home offering over 3,000 square feet of thoughtfully designed living space. This 5 bedroom, 4 bath residence feature
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312 Park Avenue
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Details for 312 Park Avenue, WINTER GARDEN, FL 34787
Single Family
  1. Price: $600,000.00
  2. Price sqft: $318.47 / sqft
  3. Previous Price: $625,000
  4. Last Price Change: 11/24/25
  5. Days On Market: 144
  6. Bedrooms: 3
  7. Baths: 2
  8. Bldg sqft: 1884
  9. Acreage: 0.23 acres
  10. Pool: Yes
  11. Waterfront: No
  12. Year Built: 1985
MLS#: O6337303
  1. County: ORANGE
  2. City: WINTER GARDEN
  3. Zipcode: 34787
  4. Subdivision: King Bay
  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. Welcome to your downtown Winter Garden dream. This updated three bedroom, two bath pool home sits right in the golf cart district, just minutes from Pla
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815 Burland Circle
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Details for 815 Burland Circle, WINTER GARDEN, FL 34787
Single Family
  1. Price: $599,000.00
  2. Price sqft: $167.41 / sqft
  3. Days On Market: 25
  4. Bedrooms: 5
  5. Baths: 4
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3578
  8. Acreage: 0.22 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2005
MLS#: O6368127
  1. County: ORANGE
  2. City: WINTER GARDEN
  3. Zipcode: 34787
  4. Subdivision: Fullers Xing Ph 03 Ag
  5. Elementary School: Dillard Street Elem
  6. Middle School: Lakeview
  7. High School: Ocoee
  8. Provided by: DENIZ REALTY PARTNERS LLC
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BRAND NEW ROOF installed September 2025! Your dream pool home in Winter Garden awaits! Set on a spacious corner lot just under a quarter acre, this stunning 5 bedroom, 4 bathroom home offers 2,994 sq
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1504 Spring Ridge Circle
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Details for 1504 Spring Ridge Circle, WINTER GARDEN, FL 34787
Single Family
  1. Price: $575,000.00
  2. Price sqft: $203.90 / sqft
  3. Days On Market: 9
  4. Bedrooms: 3
  5. Baths: 2
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 2820
  8. Acreage: 0.29 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 1989
MLS#: O6369221
  1. County: ORANGE
  2. City: WINTER GARDEN
  3. Zipcode: 34787
  4. Subdivision: Crown Point Springs
  5. Elementary School: Dillard Street Elem
  6. Middle School: Lakeview
  7. Provided by: HOMEVEST REALTY
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Welcome home to the relaxed, easygoing charm of Downtown Winter Garden living. This three bedroom, two bath pool home sits on an oversized lot and offers the lifestyle so many people are searching for
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500 Teacup Springs Court
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Details for 500 Teacup Springs Court, WINTER GARDEN, FL 34787
Single Family
  1. Price: $530,000.00
  2. Price sqft: $216.06 / sqft
  3. Days On Market: 46
  4. Bedrooms: 4
  5. Baths: 3
  6. Bldg sqft: 2453
  7. Acreage: 0.52 acres
  8. Pool: No
  9. Waterfront: No
  10. Year Built: 1995
MLS#: S5139281
  1. County: ORANGE
  2. City: WINTER GARDEN
  3. Zipcode: 34787
  4. Subdivision: Magnolia Wood
  5. Elementary School: Dillard Street Elem
  6. Middle School: Lakeview
  7. High School: Ocoee
  8. Provided by: RE/MAX PRIME PROPERTIES
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Short Sale. An exceptional opportunity for investors, builders, and developersthis property offers the ideal canvas for your next remodel, expansion, or ground up new construction project. Perfectly p
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