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$655,000
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Property Description
Mid-Century Charm Meets Modern Comfort in Winter Garden! Discover the perfect blend of classic appeal and contemporary upgrades in this delightful 3-bedroom, 2-bath pool home, ideally situated on a generous .30+ acre lot just blocks from downtown Winter Garden. Best of all, there's no HOA! Step inside and appreciate the thoughtful updates that complement the home's timeless mid-century architecture. The kitchen boasts updated Bosch appliances, including a 2021 induction range and 2023 wall oven for a total of two ovens, along with quartz countertops and an updated farm sink. You'll find engineered hardwood floors in the family room, kitchen, and hallway, and custom window blinds throughout. Peace of mind comes with a brand-new roof (July 2025), rain gutters, an AC unit replaced in 2019, and a gas hot water heater from 2018. The primary bedroom suite offers three deep closets with custom doors and a renovated en-suite bath (2021) featuring new tile, a walk-in low threshold shower, and modern fixtures that maintain the home's classic character. The hall bath was also renovated in 2023 with new tile and paint. The dining room provides a cozy ambiance with a gas fireplace and built-in shelves, while French doors open to a spacious 26x17 covered and screened back porch wired with Bluetooth speakers and also has a 220 power hookup for a hot tub. A versatile mud room/art studio/office and a dedicated laundry room add to the home's functionality. The outdoor living space is a true oasis, featuring a fenced backyard (2019) with an amazing heated saltwater pool (2019), complete with a sun ledge. The yard is kept lush with an irrigation system fed by a well (pump replaced 2020) and a French drain system (2019) for optimal drainage. The north gate is a double gate, allowing boat or RV parking behind the fence, with an RV electric outlet on the side of the house. Plus, there's a large elevated workshop building with electricity and AC for your projects (As Is). In 2023, a variance was obtained through the City of Winter Garden to build a new structure where the current workshop sits, which also allows for an attached covered veranda to be built. Beyond your doorstep, the vibrant heart of Winter Garden awaits. This home is located in the golf cart district, allowing you to drive your own golf cart on approved roads. Enjoy leisurely strolls to the weekend farmers market, participate in festive holiday events, and explore a diverse array of restaurants and shops. You're also within walking distance to Lake Apopka, where breathtaking sunsets are a daily spectacle, and it's renowned as one of Florida's top three birding areas. The Jessie Brock Community Center (offering exercise and Crealde art classes) and its pond with a paved walking circuit and exercise stations are also just a short walk away, as is the West Orange Bike Trail. This Winter Garden gem offers not just a home, but a lifestyle. Don't miss your chance to own a piece of this charming and convenient community!
Full Property Details
Full Property Details for 423 N Main St
General
- Sold For: $655,000
- Taxes: $3,410 (2024)
- Status: Closed
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: O6331314
- Added to Site: 168 day(s) ago
Rental Information
- Min. Lease: 8-12 Months
Interior
- Number of Rooms: 9
- Interior Features: Ceiling Fan(s), Solid Surface Counters, Stone Counters
- Fireplace: Yes
- Fireplace(s): Gas
- Appliances: Built-In Oven, Convection Oven, Cooktop, Disposal, Gas Water Heater, Refrigerator
- Flooring: Ceramic Tile, Concrete, Engineered Hardwood, Parquet
Rooms
Bathrooms
- Total Bathrooms: 2
- Full Bathrooms: 2
Bedrooms
- Total Bedrooms: 3
Other Rooms
- Laundry: Inside, Laundry Room
Additional Information
- Pool: Yes
- Private Pool: Yes
- Pool Description: Heated, In Ground, Salt Water
Exterior
- Exterior Features: Rain Gutters
- Deck/Patio: Covered, Patio, Rear Porch, Screened
- Porch/Patio/Deck: Covered, Patio, Rear Porch, Screened
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 2
- Covered Spaces: 2
- Parking Features: Driveway
Location
- Area: 34787 - Winter Garden/Oakland
- County: Orange
- Development Name: 34787 - Winter Garden/Oakland
- Subdivision: WINTER GARDEN SHORES FIRST ADD
- Driving Directions: From the SR 429 (Daniel Webster Western Beltway), to reach 423 N Main St in Winter Garden, FL, if you're heading southbound, take Exit 24 for FL-438 toward Plant St/Franklin St, then turn right onto Plant St, and continue until you turn right onto N Main St where your destination will be on the right; if you're heading northbound, take Exit 24 for FL-438 toward Plant St/Franklin St, then turn left onto Plant St, continue until you turn right onto N Main St, and your destination will be on the right.
- Direction Faces: West
School Information
- Elementary School: Dillard Street Elem
- Middle School: Lakeview Middle
- High School: West Orange High
Community
- Community Name: 34787 - Winter Garden/Oakland
- Pet Restrictions: Check with City and County
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Central
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: BB/HS Internet Available, Cable TV Available, Electricity Connected, Fiber Optics, Natural Gas Available, Natural Gas Connected, Public, Sewer Connected
Structural Information
- Architectural Info: Ranch
- Architectural Style: Ranch
- Exterior Const.: Block
- Roof: Shingle
- Windows: Blinds, Double Pane Windows
- Stories/Levels: One
- Square Feet: 1,668
- Sq. Ft. Source: Public Records
- Living Area: 1,668 Sq. Ft.
- Year Built: 1957
Additional Structures
- Other Structures: Workshop
Lot Features
- Lot Size (Acres): 0.3
- Lot Size (Sq. Ft.): 13,147
- Lot Size: 13147
- Frontage: Street Paved
- Street/Road Desc.: Paved, Asphalt
- Fencing (Description): Vinyl
Financial Considerations
- Tax Amount: $3,410
- Tax Year: 2024
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: WINTER GARDEN SHORES FIRST ADDITION T/86LOT 9 BLK A
- Flood Zone Info: X
- APN: 142227938801090
- Property ID: 142227938801090
- Block/Lot/Section: A
Listed by Compass Florida Llc
Sold by Coldwell Banker Hubbard Hansen
Get Pre-Approved Today
Schools
Schools serving 423 N Main St
School District:Orange County School District
| Name | Grades | Distance |
|---|---|---|
Dillard Street Elementary School 311 North Dillard Street, Winter Garden, FL 34787 | PK-5 | 0.2 mi |
Lakeview Middle School 1200 West Bay Street, Winter Garden, FL 34787 | 6-8 | 1.2 mi |
West Orange High School 1625 Beulah Road, Winter Garden, FL 34787 | 9-12 | 2.4 mi |
Disclaimer:
School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 423 N Main St
Date
Details
Price
Change
Source
9/26/2025
Sold
$655,000
-0.61%
MLS
8/25/2025
Price Reduced
$659,000
-3.09%
MLS
8/01/2025
Listed
$680,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
423 N Main Street, Winter Garden, FL 34787 (MLS# O6331314) is a Single Family property that was sold at $655,000 on September 26, 2025. Want to learn more about 423 N Main Street? Do you have questions about finding other Single Family real estate for sale in Winter Garden? You can browse all Winter Garden real estate or contact a Coldwell Banker agent to request more information.

