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244 Palm Sparrow Court
200 John Anderson Drive
116 Oceans Circle
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  1. School = Dillard Street Elem
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241 Dillard Street
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Details for 241 Dillard Street, WINTER GARDEN, FL 34787
Single Family
  1. Price: $1,750,000.00
  2. Price sqft: $374.65 / sqft
  3. Previous Price: $1,800,000
  4. Last Price Change: 02/20/26
  5. Days On Market: 124
  6. Bedrooms: 3
  7. Baths: 3
  8. Garage / Parking Spaces: 6
  9. Bldg sqft: 4671
  10. Acreage: 0.64 acres
  11. Pool: No
  12. Waterfront: No
  13. 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
  9. mfrmls
  10. DMCA Notice
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: 79
  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: $1,180,000.00
  2. Price sqft: $244.46 / sqft
  3. Previous Price: $1,290,000
  4. Last Price Change: 02/17/26
  5. Days On Market: 26
  6. Bedrooms: 4
  7. Baths: 3
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 4827
  10. Acreage: 0.33 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: No
  14. 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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NEW PRICE and Brand New Renewal by Anderson Double Paned Windows coming soon ($60,000 value)!!! Welcome to Courtlea Oaks, one of Winter Gardens most timeless and charming communities, perfectly positi
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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: 140
  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: 36
  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: 43
  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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815 Burland Circle
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Details for 815 Burland Circle, WINTER GARDEN, FL 34787
Single Family
  1. Price: $595,000.00
  2. Price sqft: $166.29 / sqft
  3. Previous Price: $599,000
  4. Last Price Change: 02/12/26
  5. Days On Market: 66
  6. Bedrooms: 5
  7. Baths: 4
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 3578
  10. Acreage: 0.22 acres
  11. Pool: Yes
  12. Waterfront: No
  13. 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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$34,000 BELOW APPRAISED VALUE (Appraisal report completed February 2026). BRAND NEW ROOF installed September 2025! Your dream pool home in the recently expanded, highly sought after Golf Cart District
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236 Newell Street
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Details for 236 Newell Street, WINTER GARDEN, FL 34787
Single Family
  1. Price: $550,000.00
  2. Price sqft: $244.44 / sqft
  3. Days On Market: 7
  4. Bedrooms: 2
  5. Baths: 2
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 2250
  8. Acreage: 0.20 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 2014
MLS#: O6378058
  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: KELLER WILLIAMS REALTY AT THE LAKES
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Welcome home to this RARE opportunity in the HISTORIC DISTRICT OF DOWNTOWN WINTER GARDEN! Admire the luscious, low maintenance landscaping immediately upon your arrival. Step inside and find an open c
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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: 87
  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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1669 Markel Drive
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Details for 1669 Markel Drive, WINTER GARDEN, FL 34787
Land
  1. Price: $415,000.00
  2. Previous Price: $425,000
  3. Last Price Change: 06/17/25
  4. Days On Market: 492
  5. Acreage: 0.48 acres
  6. Pool: No
  7. Waterfront: No
  8. Year Built: Not Available
MLS#: O6249563
  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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This 0.48 lot is flat and clear on a quiet, dead end street in Hillcrest across from McAllister's Landing off S Fuller Rd. BEST RESIDENTIAL LOT IN WINTER GARDEN! No HOA! No wetlands, no land to clear.
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