# 199 DICKS HOLLOW Road, Winchester, VA 22603 > **TL;DR:** 5bd/1ba single family, $340,000 ($283/sqft), built 1960, 1,200 sqft. > A/C. Est. $1,818/mo. Listed 9 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $340,000 | | Price/sqft | $283 | | Bedrooms | 5 | | Bathrooms | 1 full | | Square Feet | 1,200 | | Year Built | 1960 | | Lot Size | 77,101 sqft (1.77 acres) | | Stories | 2 | | Property Type | Single Family (Other) | | Status | Active | | Days on Market | 9 | ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $1,719 | | Estimated Insurance | $99 | | **Total** | **$1,818** | ## Key Amenities - A/C ## Property Highlights - Built in 1960 - 1.77 acre lot - 2 stories - 8 parking spaces ## Description ### Agent 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 for clothes and personal items. 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. ## Location - **Address:** 199 DICKS HOLLOW Road, Winchester, VA 22603 - **County:** FREDERICK - **Neighborhood:** A MELVIN LEWIS - **Coordinates:** 39.20302, -78.24855 - **Google Maps:** https://www.google.com/maps?q=39.20302,-78.24855 ## Listing Agent - **Name:** Cynthia Lee · **License:** 0225236071 - **Brokerage:** Re/Max Roots - **Phone:** 5405398020 - **Broker Phone:** (540) 686-7362 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/199-Dicks-Hollow-Rd_Winchester_VA_22603_M64738-85456?f=listhub&s=TRENDPA&m=VAFV2045014&c=propsimple) ## Photos ![199 DICKS HOLLOW Road - Photo 1](http://lh.rdcpix.com/53fb6783b3cc457c21ceda34c452033cl-f3929566998r.jpg) ![199 DICKS HOLLOW Road - Photo 2](http://lh.rdcpix.com/53fb6783b3cc457c21ceda34c452033cl-f1453154712r.jpg) ![199 DICKS HOLLOW Road - Photo 3](http://lh.rdcpix.com/53fb6783b3cc457c21ceda34c452033cl-f1778693862r.jpg) ![199 DICKS HOLLOW Road - Photo 4](http://lh.rdcpix.com/53fb6783b3cc457c21ceda34c452033cl-f1002170209r.jpg) ![199 DICKS HOLLOW Road - Photo 5](http://lh.rdcpix.com/53fb6783b3cc457c21ceda34c452033cl-f910634009r.jpg) ![199 DICKS HOLLOW Road - Photo 6](http://lh.rdcpix.com/53fb6783b3cc457c21ceda34c452033cl-f2866862269r.jpg) ![199 DICKS HOLLOW Road - Photo 7](http://lh.rdcpix.com/53fb6783b3cc457c21ceda34c452033cl-f698018807r.jpg) ![199 DICKS HOLLOW Road - Photo 8](http://lh.rdcpix.com/53fb6783b3cc457c21ceda34c452033cl-f2610117059r.jpg) ![199 DICKS HOLLOW Road - Photo 9](http://lh.rdcpix.com/53fb6783b3cc457c21ceda34c452033cl-f4035431382r.jpg) ![199 DICKS HOLLOW Road - Photo 10](http://lh.rdcpix.com/53fb6783b3cc457c21ceda34c452033cl-f4206495913r.jpg) ![199 DICKS HOLLOW Road - Photo 11](http://lh.rdcpix.com/53fb6783b3cc457c21ceda34c452033cl-f1492032426r.jpg) ![199 DICKS HOLLOW Road - Photo 12](http://lh.rdcpix.com/53fb6783b3cc457c21ceda34c452033cl-f471922727r.jpg) ![199 DICKS HOLLOW Road - Photo 13](http://lh.rdcpix.com/53fb6783b3cc457c21ceda34c452033cl-f2855488877r.jpg) ![199 DICKS HOLLOW Road - Photo 14](http://lh.rdcpix.com/53fb6783b3cc457c21ceda34c452033cl-f3403268300r.jpg) ![199 DICKS HOLLOW Road - Photo 15](http://lh.rdcpix.com/53fb6783b3cc457c21ceda34c452033cl-f984070048r.jpg) ![199 DICKS HOLLOW Road - Photo 16](http://lh.rdcpix.com/53fb6783b3cc457c21ceda34c452033cl-f3729939593r.jpg) ![199 DICKS HOLLOW Road - Photo 17](http://lh.rdcpix.com/53fb6783b3cc457c21ceda34c452033cl-f1558152252r.jpg) ![199 DICKS HOLLOW Road - Photo 18](http://lh.rdcpix.com/53fb6783b3cc457c21ceda34c452033cl-f3626100131r.jpg) ![199 DICKS HOLLOW Road - Photo 19](http://lh.rdcpix.com/53fb6783b3cc457c21ceda34c452033cl-f2138237348r.jpg) ![199 DICKS HOLLOW Road - Photo 20](http://lh.rdcpix.com/53fb6783b3cc457c21ceda34c452033cl-f2684501718r.jpg) ![199 DICKS HOLLOW Road - Photo 21](http://lh.rdcpix.com/53fb6783b3cc457c21ceda34c452033cl-f2667322608r.jpg) ![199 DICKS HOLLOW Road - Photo 22](http://lh.rdcpix.com/53fb6783b3cc457c21ceda34c452033cl-f1083338555r.jpg) ![199 DICKS HOLLOW Road - Photo 23](http://lh.rdcpix.com/53fb6783b3cc457c21ceda34c452033cl-f2315814514r.jpg) ![199 DICKS HOLLOW Road - Photo 24](http://lh.rdcpix.com/53fb6783b3cc457c21ceda34c452033cl-f1853599056r.jpg) ![199 DICKS HOLLOW Road - Photo 25](http://lh.rdcpix.com/53fb6783b3cc457c21ceda34c452033cl-f4275631849r.jpg) ![199 DICKS HOLLOW Road - Photo 26](http://lh.rdcpix.com/53fb6783b3cc457c21ceda34c452033cl-f3191759277r.jpg) ![199 DICKS HOLLOW Road - Photo 27](http://lh.rdcpix.com/53fb6783b3cc457c21ceda34c452033cl-f405716483r.jpg) ![199 DICKS HOLLOW Road - Photo 28](http://lh.rdcpix.com/53fb6783b3cc457c21ceda34c452033cl-f4174083994r.jpg) ![199 DICKS HOLLOW Road - Photo 29](http://lh.rdcpix.com/53fb6783b3cc457c21ceda34c452033cl-f109786061r.jpg) ![199 DICKS HOLLOW Road - Photo 30](http://lh.rdcpix.com/53fb6783b3cc457c21ceda34c452033cl-f4258224530r.jpg) ![199 DICKS HOLLOW Road - Photo 31](http://lh.rdcpix.com/53fb6783b3cc457c21ceda34c452033cl-f576159101r.jpg) ![199 DICKS HOLLOW Road - Photo 32](http://lh.rdcpix.com/53fb6783b3cc457c21ceda34c452033cl-f1452930638r.jpg) ![199 DICKS HOLLOW Road - Photo 33](http://lh.rdcpix.com/53fb6783b3cc457c21ceda34c452033cl-f776193629r.jpg) ![199 DICKS HOLLOW Road - Photo 34](http://lh.rdcpix.com/53fb6783b3cc457c21ceda34c452033cl-f1834185757r.jpg) ![199 DICKS HOLLOW Road - Photo 35](http://lh.rdcpix.com/53fb6783b3cc457c21ceda34c452033cl-f2376289981r.jpg) ![199 DICKS HOLLOW Road - Photo 36](http://lh.rdcpix.com/53fb6783b3cc457c21ceda34c452033cl-f1259211359r.jpg) ![199 DICKS HOLLOW Road - Photo 37](http://lh.rdcpix.com/53fb6783b3cc457c21ceda34c452033cl-f487597319r.jpg) ![199 DICKS HOLLOW Road - Photo 38](http://lh.rdcpix.com/53fb6783b3cc457c21ceda34c452033cl-f2139424006r.jpg) ![199 DICKS HOLLOW Road - Photo 39](http://lh.rdcpix.com/53fb6783b3cc457c21ceda34c452033cl-f2931715068r.jpg) ![199 DICKS HOLLOW Road - Photo 40](http://lh.rdcpix.com/53fb6783b3cc457c21ceda34c452033cl-f2848953916r.jpg) ![199 DICKS HOLLOW Road - Photo 41](http://lh.rdcpix.com/53fb6783b3cc457c21ceda34c452033cl-f2865323400r.jpg) ![199 DICKS HOLLOW Road - Photo 42](http://lh.rdcpix.com/53fb6783b3cc457c21ceda34c452033cl-f42125950r.jpg) ![199 DICKS HOLLOW Road - Photo 43](http://lh.rdcpix.com/53fb6783b3cc457c21ceda34c452033cl-f490348768r.jpg) --- **MLS#:** VAFV2045014 | **Updated:** 2026-09-27 **Source:** listhub *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.* [View on PropertySimple](https://www.propertysimple.ai/listing/199-dicks-hollow-road-winchester-va-22603-v2045014) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://www.propertysimple.ai/listing/199-dicks-hollow-road-winchester-va-22603-v2045014#listing", "url": "https://www.propertysimple.ai/listing/199-dicks-hollow-road-winchester-va-22603-v2045014", "name": "199 DICKS HOLLOW Road, Winchester, VA 22603", "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 for clothes and personal items. 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. 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