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$423,900 Just Listed

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1,365 Sq. Ft.
  • Updated 2 days ago
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Welcome to 1033 Sunnyside Drive, a beautifully renovated bungalow tucked away on a quiet street just minutes from historic downtown Winchester. This charming home blends classic character with modern upgrades, creating a warm and inviting place to call home. Start your day on the inviting 9' x 11' tiled front porch, complete with new railings and stairs, the perfect spot for morning coffee or relaxing autumn evenings. Inside, the home has been completely updated from top to bottom with stylish, move-in-ready finishes. The open-concept layout creates a bright and comfortable living space filled with natural light, while the newly finished upper level offers flexible use as a third bedroom, home office, den, craft room, or additional storage. Enjoy peace of mind with central AC and heating, including an HVAC system installed in 2024. Additional improvements include an encapsulated crawl space with new supports, insulation, and a vapor barrier. For hobbyists or DIY enthusiasts, the reinforced workshop space features new cinder block support, electrical outlets, and lighting, ideal for projects or storage. The side deck off the kitchen provides easy access to both the front and backyard, making outdoor living and entertaining effortless. Homes with this level of renovation, charm, and location don't stay on the market long. Major upgrades include 100% waterproof luxury vinyl plank flooring, new carpeting on the upper level, brand-new kitchen cabinets, backsplash and quartz countertops, new stainless steel appliances along with a new washer and dryer, modern recessed lighting, custom-tiled bathrooms, new interior and exterior doors, fresh paint throughout, and a new wooden fence. Additional highlights include a covered porch with a 9' x 15' storage or workshop area underneath, a large parking pad with space for 4 to 6 vehicles, no HOA, and the benefit of Frederick County taxes while still enjoying a Winchester address. Conveniently located with quick access to I-81, Route 522, Route 50, and Route 37, commuting and daily errands are a breeze.

Full Property Details for 1033 Sunnyside Dr

General

  • Price: $423,900
  • Taxes: $985 (2025)
  • Status: Active
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: VAFV2040250
  • Updated: 3/23/2026
  • Added to Site: 2 day(s) ago

Interior

  • Rooms/Areas: Living Room, Bedroom 2, Basement, Bedroom 1, Bathroom 1, Bathroom 2, Attic
  • Interior Features: Breakfast Area, Recessed Lighting, Attic, Ceiling Fan(s), Combination Kitchen/Dining, Floor Plan - Open, Air Filter System
  • Appliances: Refrigerator, Built-In Microwave, Washer, Dryer, Disposal, Dishwasher, Stove
  • Flooring: Luxury Vinyl Plank, Carpet

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2
  • Main Floor Baths: 2
  • Main - Full Baths: 2

Bedrooms

  • Total Bedrooms: 3
  • Bedrooms Upper: 1
  • Bedrooms Main & Up: 2

Other Rooms

  • Laundry: Main Floor

Exterior

  • Exterior Features: Exterior Lighting
  • Porch/Patio/Deck: Deck(s), Porch(es)

Parking

  • Parking Type: Driveway, Off Street

Location

  • County: FREDERICK
  • Subdivision: SUNNYSIDE
  • Cross Streets: N Frederick Pike
  • Driving Directions: From Winchester, Fairmont Ave. take Route 522 North (North Frederick Pike) travel approx. 1/2 mile to turn right on Sunnyside Drive, to 2nd house on left.
  • Direction Faces: East

School Information

  • School District: Frederick County Public Schools
  • Elementary School: Apple Pie Ridge
  • Middle School: James Wood
  • High School: James Wood

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Central A/C
  • Cooling Fuel: Electric
  • Heating Type: Heat Pump(s)
  • Heating Fuel: Electric
  • Water Heater: Electric

Utilities

  • Sewer: Public Sewer
  • Water: Public

Structural Information

  • Architectural Style: Bungalow
  • Structure Type: Detached
  • Construction: Vinyl Siding
  • Foundation: Crawl Space, Other
  • Walls/Ceilings: Dry Wall
  • Doors: Insulated, Storm
  • Entry Floor Number: 1
  • Stories/Levels: 1
  • Stories Description: Lower 1, Main, Upper 1
  • Square Feet: 1,365
  • Sq. Ft. Source: Estimated
  • Living Area: 1,365 Sq. Ft.
  • Finished Above Grnd: 1,365 Sq. Ft.
  • Year Built: 1951
  • Year Built Source: Estimated

Lot Features

  • Lot Size (Acres): 0.12
  • Lot Size (Sq. Ft.): 5,227
  • Lot Size Source: Estimated
  • Zoning: RP

Financial Considerations

  • Price Per Sq. Ft.: $310.55
  • Assessment Year: 2025
  • City/TownTax Freq: Annually
  • Tax w/Assessment: $205,300
  • Tax Amount: $985
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Section: 53A
  • Lot Number: 57

Listed by Redfin Corporation, Joseph K Dao

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Listing agent

— 1033 Sunnyside Dr —

  • Joseph K Dao

    Redfin Corporation

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 1033 Sunnyside Dr

School District:Frederick County Public Schools, Winchester, VA
NameGradesDistance
Apple Pie Ridge Elementary School
349 Apple Pie Ridge Road, Winchester, VA 22603
PK-50.7 mi
James Wood Middle School
1313 Amherst Street, Winchester, VA 22601
6-81.5 mi
James Wood High School
161 Apple Pie Ridge Road, Winchester, VA 22603
9-120.9 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 1033 Sunnyside Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
3/23/2026
Listed
$423,900
97.16%
MLS
11/21/2025
Sold
$215,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 1033 Sunnyside Dr

Year
Property Taxes
Change
Tax Assessment
Change
2024
$381
—
$205,300
38%
2024
$381
—
$149,300
—
2023
$381
-48%
$149,300
24%
2022
$733
—
$120,200
—
2021
$733
—
$120,200
—
2020
$733
—
$120,100
—
2019
$733
7%
$120,100
7%
2018
$687
2%
$112,700
—
2017
$676
28%
$112,700
28%
2016
$529
7%
$88,200
—
2015
$494
14%
$88,200
20%
2014
$432
—
$73,800
—
2013
$432
—
$73,800
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Listed by Redfin Corporation, Joseph K Dao

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1033 Sunnyside Drive, Winchester, VA 22603 (MLS# VAFV2040250) is a Single Family property with 3 bedrooms and 2 full bathrooms. 1033 Sunnyside Drive is currently listed for $423,900 and was received on March 23, 2026. Want to learn more about 1033 Sunnyside Drive? Do you have questions about finding other Single Family real estate for sale in Winchester? You can browse all Winchester real estate or contact a Coldwell Banker agent to request more information.

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