Price Reduced25
$274,900
2 bd · 2 ba · 1,242 sqft
306 Winding Oak Dr, Hagerstown, MD
Mary Schroth · EXP Realty, LLC
Est. $1,816/mo$254/sqft · 22 days on Realty
2
Beds
1
Baths
1,043
Sqft
1966
Built
Nestled in the charming West End, this exquisite ranch-style home offers a perfect blend of comfort and luxury. With its inviting curb appeal, the property boasts a beautifully landscaped 0.43-acre lot, featuring lush gardens and mature trees that create a serene backdrop for outdoor living. The wrap-around porch and expansive deck invite you to unwind and enjoy the tranquil surroundings, while the hot tub promises relaxation under the stars. Step inside to discover a warm and welcoming interior, where hardwood and laminated floors flow seamlessly throughout. The traditional floor plan includes a spacious entry-level bedroom and a thoughtfully designed dining area that connects to the modern kitchen, complete with upgraded countertops and stainless steel appliances. The built-in features and cozy fireplace add character and charm, making this space perfect for gatherings or quiet evenings at home. The full basement, equipped with a connecting stairway and walkout access, offers endless possibilities for customization, whether you envision a home gym, workshop, or additional living space. With a detached garage providing ample storage and parking, convenience is at your fingertips. Enjoy picturesque views of the garden and surrounding trees, enhancing the exclusive lifestyle this property offers. This home is not just a residence; it's a sanctuary that meets comfort, inviting you to create lasting memories.
Listing agent
Casey L Cauffman
Courtesy of Berkshire Hathaway HomeServices Homesale Realty
(240) 291-3798
Bright MLS · Listing MDWA2040650
$53,000
Estimated monthly payment
$1,816/mo
Loan amount $212,000. Estimate only — your actual rate and payment depend on credit, location, and lender.
2026 roll
School ratings (A+ to F) from HJN community data.
Truth Christian Academy
PK-12 · Regular
58 students · 5.5:1 student–teacher
Salem Avenue Elementary School
PK-5 · Regular · Washington County Public Schools
713 students · 14.2:1 student–teacher
Western Heights Middle School
6-8 · Regular · Washington County Public Schools
883 students · 12.1:1 student–teacher
Washington County Job Development Center
12-12 · Special Education · Washington County Public Schools
38 students · 6.3:1 student–teacher
Marshall Street School
PK-12 · Special Education · Washington County Public Schools
47 students · 3.6:1 student–teacher
St Mary Catholic School
PK-8 · Regular
180 students · 12.9:1 student–teacher
Barbara Ingram School for the Arts
9-12 · Regular · Washington County Public Schools
347 students · 14.5:1 student–teacher
Jonathan Hager Elementary School
PK-5 · Regular · Washington County Public Schools
498 students · 14.9:1 student–teacher
Bright MLSThis content last refreshed on 2026-10-27 00:26:21 UTC. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.
Price Reduced25
$274,900
2 bd · 2 ba · 1,242 sqft
306 Winding Oak Dr, Hagerstown, MD
Mary Schroth · EXP Realty, LLC
55$320,000
3 bd · 2 ba · 1,954 sqft
17933 Oak Ridge Dr, Hagerstown, MD
Jeanine McVicker · AEK Real Estate, LLC
Price Reduced26$210,000
3 bd · 1 ba · 1,092 sqft
541 Guilford Ave, Hagerstown, MD
Jonathan C. Fleming III · Weichert Realtors - Blue Ribbon
Price Reduced38$219,500
3 bd · 1 ba · 1,344 sqft
822 Salem Ave, Hagerstown, MD
Corey C Linthicum · AEK Real Estate, LLC
24$240,000
3 bd · 2 ba · 1,280 sqft
35 N Cleveland Ave, Hagerstown, MD
James M Keating Jr. · Keller Williams Realty Centre
Price Reduced66$279,000
3 bd · 2 ba · 1,561 sqft
721 Virginia Ave, Hagerstown, MD
Ashkan Hosseinipoul · United Real Estate Premier





Within 2 miles of this home: 39+ restaurants and cafés, 5 grocery stores, 27 parks and green spaces, and 2 transit stops.
Place data from OpenStreetMap.
Dino's Pizza
TGI Fridays
American restaurant
KPOT
IHOP
Tropical Smoothie Cafe
Garland Groh Boulevard
Starbucks
Garland Groh Boulevard
Arby's
Garland Groh Boulevard
Chipotle
Mexican restaurant · Garland Groh Boulevard
Walmart Supercenter
Garland Groh Boulevard
S&K Mercadito Latino
Martin's Food
Wesel Boulevard
ALDI
Dual Highway
Save-A-Lot
Maryland Avenue
Hellane Park
National Road Park
Elgin Station Community Park
Ridge Avenue Playground
South Prospect Street Historic District
City Park
Lower Lake
University Plaza
WCT Office
Hagerstown Transit Center
Rings at ½ mile and 1 mile. Basemap © OpenMapTiles © OpenStreetMap contributors.
Open the Hagerstown camera map4 license-plate readers mapped within 1 mile of this home, 2 of them identified as Flock Safety devices. None within ½ mile. Nearest: 0.8 mi southeast. Operator named in the data: Maryland State Police.
| Device type | Within ½ mi | Within 1 mi |
|---|---|---|
| License-plate readers | 0 | 4 |
| of which Flock Safety | 0 | 2 |
Community-reported via OpenStreetMap; may be incomplete. Data as of . © OpenStreetMap contributors (ODbL)
License-plate readers (ALPR) are fixed cameras that photograph passing vehicles and read their plates. Records are typically shared with the agency or association that operates the camera.
Flock Safety is a company whose plate-reader cameras are used by police departments, cities, HOAs and businesses. Its devices are usually solar-powered and pole-mounted.