Searching on:
- School = Dillard Street Elem
Single Family
- Price: $1,800,000.00
- Price sqft: $385.36 / sqft
- Days On Market: 31
- Bedrooms: 3
- Baths: 3
- Garage / Parking Spaces: 3
- Bldg sqft: 4671
- Acreage: 0.64 acres
- Pool: No
- Waterfront: No
- Year Built: 1953
MLS#: O6353975
- County: ORANGE
- City: WINTER GARDEN
- Zipcode: 34787
- Subdivision: J L Dillard Sub 3
- Elementary School: Dillard Street Elem
- Middle School: Lakeview Middle
- High School: West Orange High
- Provided by: HOMEVEST REALTY
- DMCA Notice
Description
- 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 proudly on a rare triple lot in one o
Townhome
- Price: $1,289,000.00
- Price sqft: $375.26 / sqft
- Days On Market: 17
- Bedrooms: 3
- Baths: 4
- Garage / Parking Spaces: 2
- Bldg sqft: 3435
- Acreage: 0.03 acres
- Pool: No
- Waterfront: No
- Year Built: 2019
MLS#: G5103956
- County: ORANGE
- City: WINTER GARDEN
- Zipcode: 34787
- Subdivision: Park Placewinter Garden
- Elementary School: Dillard Street Elem
- Middle School: Lakeview Middle
- High School: West Orange High
- Provided by: ERA GRIZZARD REAL ESTATE
-
- DMCA Notice
Description
- 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
Single Family
- Price: $1,050,000.00
- Price sqft: $240.72 / sqft
- Previous Price: $1,100,000
- Last Price Change: 11/15/25
- Days On Market: 47
- Bedrooms: 4
- Baths: 3
- Garage / Parking Spaces: 2
- Bldg sqft: 4362
- Acreage: 0.69 acres
- Pool: No
- Spa/HotTub: Yes
- Waterfront: No
- Year Built: 1973
MLS#: NS1086151
- County: ORANGE
- City: WINTER GARDEN
- Zipcode: 34787
- Subdivision: Emerald Acres
- Elementary School: Dillard Street Elem
- Middle School: Lakeview Middle
- High School: West Orange High
- Provided by: ENGEL & VOLKERS NEW SMYRNA
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- DMCA Notice
Description
- 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
Single Family
- Price: $900,000.00
- Price sqft: $188.21 / sqft
- Previous Price: $950,000
- Last Price Change: 10/18/25
- Days On Market: 496
- Bedrooms: 5
- Baths: 4
- Garage / Parking Spaces: 2
- Bldg sqft: 4782
- Acreage: 0.37 acres
- Pool: Yes
- Waterfront: No
- Year Built: 1957
MLS#: O6222919
- County: ORANGE
- City: WINTER GARDEN
- Zipcode: 34787
- Subdivision: Winter Garden Shores Rep
- Elementary School: Dillard Street Elem
- Middle School: Lakeview Middle
- High School: West Orange High
- Provided by: HOMEVEST REALTY
-
- DMCA Notice
Description
- One or more photo(s) has been virtually staged. Discover the charm and convenience of luxurious living in this stunning 5 bedroom, 3 bathroom home, perfectly located in the heart of downtown Winter Ga
Single Family
- Price: $894,544.00
- Price sqft: $292.14 / sqft
- Previous Price: $859,000
- Last Price Change: 08/29/25
- Days On Market: 376
- Bedrooms: 3
- Baths: 4
- Garage / Parking Spaces: 2
- Bldg sqft: 3062
- Acreage: 0.48 acres
- Pool: No
- Waterfront: No
- Year Built: 2025
MLS#: O6256295
- County: ORANGE
- City: WINTER GARDEN
- Zipcode: 34787
- Subdivision: Hillcrest
- Elementary School: Dillard Street Elem
- Middle School: Lakeview Middle
- High School: Ocoee High
- Provided by: Q BOUTIQUE SPECIALTY REALTY INC
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- DMCA Notice
Description
- Pre Construction. To be built. NO HOA! FLAT, CLEARED, NO WETLANDS LOT IN WINTER GARDEN. This is the LAST vacant lot available in Hillcrest's established Winter Garden community across from McAllistair
Single Family
- Price: $890,000.00
- Price sqft: $321.88 / sqft
- Previous Price: $950,000
- Last Price Change: 10/25/25
- Days On Market: 149
- Bedrooms: 3
- Baths: 3
- Garage / Parking Spaces: 2
- Bldg sqft: 2765
- Acreage: 0.53 acres
- Pool: Yes
- Waterfront: No
- Year Built: 1928
MLS#: O6320452
- County: ORANGE
- City: WINTER GARDEN
- Zipcode: 34787
- Subdivision: Pleasant Park
- Elementary School: Dillard Street Elem
- Middle School: Lakeview Middle
- High School: West Orange High
- Provided by: HOMEVEST REALTY
-
- DMCA Notice
Description
- One or more photo(s) has been virtually staged. ***new reduced price! ***move in before the holidays & take advantage of the lower interest rates! The sellers are motivated and ready for the next chap
Single Family
- Price: $789,000.00
- Price sqft: $375.71 / sqft
- Previous Price: $795,000
- Last Price Change: 11/06/25
- Days On Market: 140
- Bedrooms: 4
- Baths: 2
- Garage / Parking Spaces: 2
- Bldg sqft: 2100
- Acreage: 0.27 acres
- Pool: No
- Waterfront: No
- Year Built: 1972
MLS#: O6321806
- County: ORANGE
- City: WINTER GARDEN
- Zipcode: 34787
- Subdivision: Westlake Manor 1st Add
- Elementary School: Dillard Street Elem
- Middle School: Lakeview Middle
- High School: West Orange High
- Provided by: UNITED REALTY GROUP INC
-
- DMCA Notice
Description
- Located in the heart of DOWNTOWN WINTER GARDEN!! This beautifully renovated single story home combines charm with modern upgrades. Completely redesigned in 2021, this home showcase
Single Family
- Price: $775,000.00
- Price sqft: $254.93 / sqft
- Days On Market: 2
- Bedrooms: 3
- Baths: 3
- Garage / Parking Spaces: 2
- Bldg sqft: 3040
- Acreage: 0.20 acres
- Pool: No
- Waterfront: No
- Year Built: 2019
MLS#: O6361513
- County: ORANGE
- City: WINTER GARDEN
- Zipcode: 34787
- Subdivision: Vinings Add Winter Garden
- Elementary School: Dillard Street Elem
- Middle School: Lakeview Middle
- High School: West Orange High
- Provided by: RE/MAX PRIME PROPERTIES
-
- DMCA Notice
Description
- 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
Single Family
- Price: $750,000.00
- Price sqft: $337.08 / sqft
- Days On Market: 19
- Bedrooms: 4
- Baths: 2
- Garage / Parking Spaces: 2
- Bldg sqft: 2225
- Acreage: 0.22 acres
- Pool: No
- Waterfront: No
- Year Built: 1923
MLS#: O6355801
- County: ORANGE
- City: WINTER GARDEN
- Zipcode: 34787
- Subdivision: G T Smith Sub
- Elementary School: Dillard Street Elem
- Middle School: Lakeview Middle
- High School: West Orange High
- Provided by: NATIONAL REAL ESTATE LLC
-
- DMCA Notice
Description
- Welcome home to 40 W Smith St. Step into a piece of Winter Garden's rich history with this captivating, charming historic home in the "golf district" in the heart of downtown Winter Garden. Nestled i
Single Family
- Price: $689,000.00
- Price sqft: $294.19 / sqft
- Previous Price: $705,000
- Last Price Change: 10/14/25
- Days On Market: 66
- Bedrooms: 3
- Baths: 2
- Garage / Parking Spaces: 2
- Bldg sqft: 2342
- Acreage: 0.29 acres
- Pool: No
- Waterfront: No
- Year Built: 1980
MLS#: O6343249
- County: ORANGE
- City: WINTER GARDEN
- Zipcode: 34787
- Subdivision: Westlake Manor 1st Add
- Elementary School: Dillard Street Elem
- Middle School: Lakeview Middle
- High School: West Orange High
- Provided by: COLDWELL BANKER RESIDENTIAL RE
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- DMCA Notice
Description
- PRICE IMPROVEMENT Stunning Renovated Ranch on Prime Corner Lot in Historic Downtown Winter Garden Welcome to a prime corner lot property in Historic Downtown Winter Garden that perfectly blends mo
