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Headshot for Associate Michelle Hill
  1. Michelle Hill, ABR,AHWD,PA,PSA,REALTOR ®,SFR
  2. Tropic Shores Realty
  3. Mobile: 352.247.2177
  4. 229.834.4988
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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: $1,600,000.00
  2. Price sqft: $342.54 / sqft
  3. Previous Price: $1,750,000
  4. Last Price Change: 03/24/26
  5. Days On Market: 172
  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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156 Stanton Estates Circle
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Details for 156 Stanton Estates Circle, WINTER GARDEN, FL 34787
Single Family
  1. Price: $1,200,000.00
  2. Price sqft: $378.55 / sqft
  3. Days On Market: 36
  4. Bedrooms: 4
  5. Baths: 4
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 3170
  8. Acreage: 0.30 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 2018
MLS#: O6384801
  1. County: ORANGE
  2. City: WINTER GARDEN
  3. Zipcode: 34787
  4. Subdivision: Stanton Estates
  5. Elementary School: Dillard Street Elem
  6. Middle School: Lakeview
  7. High School: West Orange
  8. Provided by: FATHOM REALTY FL LLC
  9. mfrmls
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Welcome to Golf Cart Life in Historic Downtown Winter Garden! Nestled within Stanton Estates an exclusive enclave of just 45 luxury homes this stunning contemporary masterpiece is perfectly posit
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205 Surprise Drive
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Details for 205 Surprise Drive, WINTER GARDEN, FL 34787
Single Family
  1. Price: $1,200,000.00
  2. Price sqft: $425.68 / sqft
  3. Previous Price: $1,300,000
  4. Last Price Change: 02/26/26
  5. Days On Market: 127
  6. Bedrooms: 4
  7. Baths: 3
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 2819
  10. Acreage: 0.75 acres
  11. Pool: Yes
  12. Waterfront: No
  13. 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
  9. mfrmls
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PRICE ADJUSTED to reflect recent appraisal, this four lot parcel presents immediate value with two vacant lots ready for expansion, additional income potential, or future development. Discover an exc
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615 Sigler Drive
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Details for 615 Sigler Drive, WINTER GARDEN, FL 34787
Single Family
  1. Price: $899,840.00
  2. Price sqft: $291.02 / sqft
  3. Days On Market: 38
  4. Bedrooms: 4
  5. Baths: 4
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3092
  8. Acreage: 0.08 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 2026
MLS#: O6387120
  1. County: ORANGE
  2. City: WINTER GARDEN
  3. Zipcode: 34787
  4. Subdivision: Lakeview Village Estates
  5. Elementary School: Dillard Street Elem
  6. Middle School: Lakeview
  7. Provided by: NOVA REAL ESTATE SERVICES INC
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Under Construction. Welcome to Lakeview Village Estates, an exclusive new community by award winning Davila Homes, featuring just 40 luxury residences crafted with exceptional attention to detail. Eac
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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: $869,000.00
  2. Price sqft: $349.70 / sqft
  3. Previous Price: $895,000
  4. Last Price Change: 04/07/26
  5. Days On Market: 84
  6. Bedrooms: 3
  7. Baths: 4
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 2485
  10. Acreage: 0.02 acres
  11. Pool: No
  12. Waterfront: No
  13. 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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408 Boyd Street
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Details for 408 Boyd Street, WINTER GARDEN, FL 34787
Single Family
  1. Price: $835,000.00
  2. Price sqft: $305.41 / sqft
  3. Days On Market: 10
  4. Bedrooms: 3
  5. Baths: 3
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 2734
  8. Acreage: 0.41 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 1939
MLS#: O6394810
  1. County: ORANGE
  2. City: WINTER GARDEN
  3. Zipcode: 34787
  4. Subdivision: G T Smith Sub 3
  5. Elementary School: Dillard Street Elem
  6. Middle School: Lakeview Middle
  7. High School: West Orange
  8. Provided by: RE/MAX PRIME PROPERTIES
  9. mfrmls
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Charming home located just blocks from Winter Garden's historical downtown in the highly sought after GOLF CART DISTRICT! This 3 bedroom, 3 Bath house blends timeless character with modern living, fea
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1261 Fullers Cross Road
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Details for 1261 Fullers Cross Road, Winter Garden, FL 34787
Single Family
  1. Price: $675,000.00
  2. Price sqft: $185.59 / sqft
  3. Days On Market: 1
  4. Bedrooms: 3
  5. Baths: 2
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3637
  8. Acreage: 0.96 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 1991
MLS#: O6397098
  1. County: ORANGE
  2. City: Winter Garden
  3. Zipcode: 34787
  4. Subdivision: 0000
  5. Elementary School: Dillard Street Elem
  6. Middle School: Lakeview
  7. High School: Ocoee
  8. Provided by: LPT REALTY, LLC
  9. Provided through
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Rare opportunity in Winter Garden! This property sits on approximately one acre with no HOA, offering exceptional space, flexibility, and privacy in a highly desirable location. Conveniently located
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636 Sigler Drive
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Details for 636 Sigler Drive, WINTER GARDEN, FL 34787
Townhome
  1. Price: $614,500.00
  2. Price sqft: $269.75 / sqft
  3. Days On Market: 38
  4. Bedrooms: 3
  5. Baths: 3
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 2278
  8. Acreage: 0.04 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 2026
MLS#: O6387125
  1. County: ORANGE
  2. City: WINTER GARDEN
  3. Zipcode: 34787
  4. Subdivision: Lakeview Village Estates
  5. Elementary School: Dillard Street Elem
  6. Middle School: Lakeview
  7. Provided by: NOVA REAL ESTATE SERVICES INC
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Under Construction. Under Construction. Welcome to Lakeview Village Estates an exclusive new community by award winning Davila Homes, featuring just 40 homes that seamlessly blend timeless architectu
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238 Main Street
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Details for 238 Main Street, WINTER GARDEN, FL 34787
Single Family
  1. Price: $600,000.00
  2. Price sqft: $551.98 / sqft
  3. Days On Market: 2
  4. Bedrooms: 3
  5. Baths: 2
  6. Bldg sqft: 1087
  7. Acreage: 0.19 acres
  8. Pool: No
  9. Waterfront: No
  10. Year Built: 1950
MLS#: O6397340
  1. County: ORANGE
  2. City: WINTER GARDEN
  3. Zipcode: 34787
  4. Subdivision: Orange Grove Sub
  5. Elementary School: Dillard Street Elem
  6. Middle School: Lakeview
  7. High School: West Orange
  8. Provided by: FOLIO REALTY LLC
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Can't get much closer to ***historic downtown winter garden *** than this! Seriously! Refined owner redo on this fresh & adorable 3 bedroom/2 bath fenced yard solid concrete block charmer. *** no hoa
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238 Main Street
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Details for 238 Main Street, Winter Garden, FL 34787
Single Family
  1. Price: $600,000.00
  2. Price sqft: $551.98 / sqft
  3. Days On Market: 2
  4. Bedrooms: 3
  5. Baths: 2
  6. Bldg sqft: 1087
  7. Acreage: 0.19 acres
  8. Pool: No
  9. Waterfront: No
  10. Year Built: 1950
MLS#: O6397340
  1. County: ORANGE
  2. City: Winter Garden
  3. Zipcode: 34787
  4. Subdivision: Orange Grove Sub
  5. Elementary School: Dillard Street Elem
  6. Middle School: Lakeview
  7. High School: West Orange
  8. Provided by: FOLIO REALTY LLC
  9. Provided through
  10. DMCA Notice
Can't get much closer to ***historic downtown winter garden *** than this! Seriously! Refined owner redo on this fresh & adorable 3 bedroom/2 bath fenced yard solid concrete block charmer. *** no hoa
Listing Details and 21 Additional Pictures
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