About This Home

This 5-bedroom, 1-bathroom single family at 199 DICKS HOLLOW Road in Winchester, VA is listed for $340,000 ($283 per sqft). Built in 1960, the home offers 1,200 sqft of living space on a 1.77 acres lot.

Key Features

  • Built in 1960
  • 1.77 acre lot
  • 2 stories
  • 8 parking spaces

Property Details

2 stories
1 full
8 spaces
1960

Amenities

A/C
Listing Description

Steeped in heartwarming history and beautifully updated, this charming country home sits on nearly 2 acres of serene land with a small stream in the back. Originally the seller's "grandma's house" ... he has meticulously preserved some elements and thoughtfully modernized over the last six years, perfectly blending nostalgic character with modern comfort.

He has fond memories of good times in this home from the wonderful smells from grandma baking to building boats in the basement with grandpa and floating them in the little creek that runs behind the house. Step inside to find gleaming refinished hardwood floors and a highly flexible layout featuring at least one main-floor bedroom (with the option for a second if you choose to repurpose the formal dining room).

The unexpected crown jewel of the home is a massive walk-in dressing room with boundless space. Recent high-value updates give you ultimate peace of mind, including a new HVAC system (2024), new windows, updated siding, a painted roof, a highly efficient exterior wood heating system, and freshly upgraded kitchen countertop and bathroom vanity/countertop.

Outside, the expansive property offers the perfect canvas for your farmette dreams. Ideally located just off Route 50 and only 10 minutes from the Winchester Medical Center, this home is IDEAL for just about anyone. Come see for yourself all this CUTENESS overload but be careful ...

you just might fall in LOVE! Note: Because the seller has meticulously upgraded and maintained the property, it is being sold as-is. Inspections are welcome for buyer informational purposes, but the seller will make no repairs. This home is ready for you to move right in and start building your own lifelong memories.

Monthly Cost Estimate

$1,818/mo

20% down · 6.5% · 30 years

Principal$246
Interest$1,473
Insurance$99

Estimates only. Actual payments may vary.

Location

199 DICKS HOLLOW Road

Winchester, VA 22603

A MELVIN LEWIS

Features & Amenities

Interior Features

Bathroom - Tub ShowerCeiling Fan(s)Combination Kitchen/DiningDining AreaEntry Level BedroomFloor Plan - TraditionalFormal/Separate Dining RoomKitchen - CountryKitchen - Table SpaceStove - WoodUpgraded CountertopsWindow TreatmentsWood Floors

Property Details

Construction

Block Frame Stick Built Vinyl Siding

Parking

DrivewayOff Street

Heating

Forced AirWoodCentral

Cooling

Central Air

Appliances

Built-In MicrowaveBuilt-In RangeCooktopDryer - ElectricRefrigeratorWasherWaterHeater

Questions & Answers

This 5-bedroom, 1-bathroom single family at 199 DICKS HOLLOW Road is listed at $340,000 ($283/sqft). The estimated monthly payment is $1,818 based on 20% down, a 30-year loan at 6.5% interest, estimated insurance.

Key features include: Built in 1960, 1.77 acre lot, 2 stories, 8 parking spaces. Interior Features: Bathroom - Tub Shower, Ceiling Fan(s), Combination Kitchen/Dining.

This property is listed by Cynthia Lee and can be reached at 5405398020.

CL

Cynthia Lee

License 0225236071

Agent at Re/Max Roots

(540) 539-8020

Listed by Re/Max Roots · Broker phone: (540) 686-7362 · View on Broker Site

MLS# VAFV2045014· Source: Bright MLS· 1 day on PropertySimple

Copyright © 2026 Bright MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

199 DICKS HOLLOW Road, Winchester, VA 22603

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