Skip to Main Content
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
Skip to Main Content
Refine Search
  1. Home
  2. Search Listings
  3. Search Results
Searching on:
  1. School = Dillard Street Elem
241 Dillard Street
Virtual Tour
More Like This
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: 85
  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
  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
Listing Details and 50 Additional Pictures
Request more information about this listing.
205 Surprise Drive
Virtual Tour
More Like This
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: 39
  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
  9. mfrmls
  10. DMCA Notice
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
Listing Details and 31 Additional Pictures
Request more information about this listing.
133 Park Avenue
Virtual Tour
More Like This
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: 71
  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
  9. mfrmls
  10. DMCA Notice
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
Listing Details and 91 Additional Pictures
Request more information about this listing.
100 Temple Grove Drive
Virtual Tour
More Like This
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: 101
  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
  9. mfrmls
  10. DMCA Notice
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
Listing Details and 66 Additional Pictures
Request more information about this listing.
417 Main Street
Virtual Tour
More Like This
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: 55
  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
  9. mfrmls
  10. DMCA Notice
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
Listing Details and 36 Additional Pictures
Request more information about this listing.
1474 Juniper Hammock Street
Virtual Tour
More Like This
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: 7
  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
  9. mfrmls
  10. DMCA Notice
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
Listing Details and 49 Additional Pictures
Request more information about this listing.
312 Park Avenue
Virtual Tour
More Like This
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: 146
  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
  10. DMCA Notice
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
Listing Details and 36 Additional Pictures
Request more information about this listing.
815 Burland Circle
Virtual Tour
More Like This
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: 27
  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
  9. mfrmls
  10. DMCA Notice
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
Listing Details and 37 Additional Pictures
Request more information about this listing.
1504 Spring Ridge Circle
Virtual Tour
More Like This
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: 10
  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
  8. mfrmls
  9. DMCA Notice
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
Listing Details and 20 Additional Pictures
Request more information about this listing.
500 Teacup Springs Court
Shortsale
More Like This
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: 48
  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
  9. mfrmls
  10. DMCA Notice
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
Listing Details and 3 Additional Pictures
Request more information about this listing.
Liked Listings