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  1. School = Dillard Street Elem
  2. Listing Status = Active
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: 98
  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: 53
  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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308 Forest Haven Drive
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Details for 308 Forest Haven Drive, WINTER GARDEN, FL 34787
Single Family
  1. Price: $1,290,000.00
  2. Price sqft: $267.25 / sqft
  3. Days On Market: 0
  4. Bedrooms: 4
  5. Baths: 3
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 4827
  8. Acreage: 0.33 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 2000
MLS#: O6376492
  1. County: ORANGE
  2. City: WINTER GARDEN
  3. Zipcode: 34787
  4. Subdivision: Courtlea Oaks
  5. Elementary School: Dillard Street Elem
  6. Middle School: Lakeview
  7. High School: West Orange
  8. Provided by: LAKESIDE REALTY WINDERMERE INC
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Welcome to Courtlea Oaks, one of Winter Gardens most timeless and charming communities, perfectly positioned in the heart of the golf cart district. This beautiful 4 bedroom, 2.5 bath home with a 3 ca
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308 Forest Haven Drive
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Details for 308 Forest Haven Drive, Winter Garden, FL 34787
Single Family
  1. Price: $1,290,000.00
  2. Price sqft: $267.25 / sqft
  3. Days On Market: 0
  4. Bedrooms: 4
  5. Baths: 3
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 4827
  8. Acreage: 0.33 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2000
MLS#: O6376492
  1. County: ORANGE
  2. City: Winter Garden
  3. Zipcode: 34787
  4. Subdivision: Courtlea Oaks
  5. Elementary School: Dillard Street Elem
  6. Middle School: Lakeview
  7. High School: West Orange
  8. Provided by: LAKESIDE REALTY WINDERMERE INC
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Welcome to Courtlea Oaks, one of Winter Gardens most timeless and charming communities, perfectly positioned in the heart of the golf cart district. This beautiful 4 bedroom, 2.5 bath home with a 3 ca
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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: 114
  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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131 Oak Laurel Drive
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Details for 131 Oak Laurel Drive, WINTER GARDEN, FL 34787
Townhome
  1. Price: $895,000.00
  2. Price sqft: $360.16 / sqft
  3. Days On Market: 10
  4. Bedrooms: 3
  5. Baths: 4
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 2485
  8. Acreage: 0.02 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 2019
MLS#: O6374501
  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. Provided by: KELLER WILLIAMS REALTY AT THE PARKS
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131 Oak Laurel Drive is a stunning, modern townhome built in 2019 in the highly desirable Park Place community in the heart of historic Winter Garden, Florida. This beautifully designed three story ho
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665 Brooks Field Drive
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Details for 665 Brooks Field Drive, WINTER GARDEN, FL 34787
Single Family
  1. Price: $775,000.00
  2. Price sqft: $171.08 / sqft
  3. Days On Market: 17
  4. Bedrooms: 5
  5. Baths: 4
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 4530
  8. Acreage: 0.20 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2020
MLS#: O6372524
  1. County: ORANGE
  2. City: WINTER GARDEN
  3. Zipcode: 34787
  4. Subdivision: Mcallister Lndg Ph 2
  5. Elementary School: Dillard Street Elem
  6. Middle School: Lakeview
  7. High School: Ocoee
  8. Provided by: HOMEVEST REALTY
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This Winter Garden Solar home located in MCALLISTER LANDING is a stunning pool home with tons of upgrades. Gorgeous 5 bedroom and 3.5 baths, this home is perfect for families who want to enjoy a luxur
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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: 69
  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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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: 40
  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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312 Park Avenue
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Details for 312 Park Avenue, WINTER GARDEN, FL 34787
Single Family
  1. Price: $590,000.00
  2. Price sqft: $313.16 / sqft
  3. Previous Price: $600,000
  4. Last Price Change: 01/13/26
  5. Days On Market: 159
  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
  9. mfrmls
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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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Tropic Shores Realty - Crystal River
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Listings provided courtesy of The Hernando County Association of Realtors MLS.
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Listing Data ©2026 Royal Palm Coast Realtor® Association
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Datafeed Last updated on January 27, 2026 @ 12:00 am
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