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Amy Diggs
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1949 Winston Drive
Hagerstown, MD 21740

$495,000 - Status: ACTIVE
Bed Icon Beds: 5
Bath Icon Baths: 3 full 1 partial
Sq Feet Icon SQFT: 2,833
MLS Icon MLS# MDWA2036962

Welcome to this beautifully renovated 5-bedroom, 3.5-bath single-family home tucked away on a quiet cul-de-sac in one of the area’s most desirable locations near the hospital, medical school, restaurants, shopping, parks, and public schools. Situated on an impressive .85-acre lot — a rare find within a community setting — this property offers the perfect blend of space, comfort, and convenience. Inside, you’ll find a warm and inviting layout with a modern country-inspired feel. The main level features newly updated hardwood flooring, a formal dining room, welcoming front sitting room, and an eat-in kitchen that opens to a cozy family room highlighted by a rustic wood-accent fireplace wall. The kitchen also includes a premium refrigerator that adds both style and function to the space. Upstairs offers 4 spacious bedrooms and 2 full baths, including convenient upper-level laundry tucked into the hall bath closet. The recently refinished powder room adds a fresh, updated touch to the main level. The mostly finished walk-out basement expands your living space with a guest bedroom, full bath, large rec room, and sliding glass door access to the backyard — ideal for hosting overnight guests.  Additional highlights include: • Roof less than 2 years old • HVAC approximately 7 years old • Oversized .85-acre cul-de-sac lot • Large rear deck • Attached 2-car garage • Walk-out basement

Property Features

MLS#: MDWA2036962
Zip: 21740
Subdivision: Fairway Meadows
Development: Hagerstown
Property Type: Residential - Single Family
Basement: Yes
Basement: Connecting Stairway, Daylight, Partial, Walkout Level, Windows, Partially Finished
Cooling: Central A/C
Days on Site: 2
Fireplaces: 1
Fuel Type: Electric
Garage: 2
Heating: Heat Pump(s)
Home Style: Colonial
Lot Size: 0.85 acres
Stories: 2.0
Taxes: $7,062
Year Built: 2002

Feature Descriptions

Additional Structures: Above Grade, Below Grade
Appliances: Built-In Microwave, Disposal, Dishwasher, Exhaust Fan, Oven/Range - Electric, Refrigerator
Exterior: Vinyl Siding
Exterior: Street Lights
Flooring: Hardwood
Interior: Breakfast Area, Built-Ins, Family Room Off Kitchen, Floor Plan - Traditional, Formal/Separate Dining Room, Kitchen - Table Space, Primary Bath(s), Bathroom - Tub Shower, Upgraded Countertops, Walk-in Closet(s)
Lot Dimensions: 0.85 Acre(S)
Municipality: Hagerstown
Parking Notes: 2 Total Parking Spaces
Pet Restrictions: No Pet Restrictions
Sewer: Public Sewer
Special View Info: Trees/Woods
SQFT Above Finished: 2133
SQFT Below Finished: 700
SQFT Total Finished: 2833
Structure Type: Detached
Total Garage/Parking Spaces: 2
Water: Public

Local Schools

High School: SOUTH HAGERSTOWN SR
Middle School: E. RUSSELL HICKS SCHOOL
Elementary School: EASTERN
School District: WASHINGTON COUNTY PUBLIC SCHOOLS

1949 Winston Drive | MLS# MDWA2036962

This single family home located at 1949 Winston Drive, Hagerstown, MD 21740 is currently listed for sale with an asking price of $495,000. This property was built in 2002 and has 5 bedrooms and 3 full and 1 partial baths with 2833 sq. ft. Winston Drive is located in the FAIRWAY MEADOWS subdivision within the WASHINGTON COUNTY PUBLIC SCHOOLS school district. Search FAIRWAY MEADOWS real estate on adiggs.bachrealestate.com today.

Disclosure: Exterior landscaping may be different than shown in photos as a result of Hurricane Ian.

Listed By / Shown By

Listed By

Agency Name: Sullivan Select, LLC.
Agency Phone: 3017455500

Shown By

Agent Name: Amy Diggs
Agent Phone: Cell: (240) 409-3673
Agency Title: Bach Real Estate

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AGENT INFORMATION

Bach Real Estate Amy Diggs (cell) (240) 409-3673

Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 05/16/2026. The listing information on this page last changed on 05/16/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Sat 05/16/2026 12:09:36 AM EST) or Bright MLS (last updated Fri 05/15/2026 5:03:44 PM EST). Real estate listings held by brokerage firms other than Bach Real Estate may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
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