Welcome to a private retreat where timeless charm meets peaceful mountain beauty. Set on 0.59 acres of fully fenced, professionally landscaped grounds, this all-brick hillside home offers breathtaking views of the Blue Ridge Mountains along a quiet stretch of Middle Road. Inside, sunlight pours through expansive living spaces, creating a warm and inviting atmosphere. The open-concept design flows effortlessly, ideal for both refined entertaining and relaxed everyday living. Step onto the stunning 9’ x 31’ covered porch and experience true serenity—perfect for morning coffee, evening conversations, or simply taking in the surrounding natural beauty. With over 2,400 square feet, 3 bedrooms, and 3 bathrooms, this home offers generous space and flexibility. The partially finished basement—with a full bath, potential fourth bedroom, and large den—creates endless possibilities for a media room, fitness space, or private office. Thoughtfully updated throughout, the home features new upper-level flooring, plush bedroom carpeting, custom wood trim, updated fixtures, a new kitchen sink, and a beautiful wood-burning fireplace. Exterior improvements include a new retaining wall, refreshed landscaping, updated gutters and a new septic system. . Additional highlights include central air and heat, a radon mitigation system, water softener, in-home washer and dryer, and the rare advantage of no HOA. Ideally located near shopping, schools, Valley Health, and Historic Downtown Winchester, this property offers the perfect blend of privacy, comfort, and convenience.
For sale
Price cut: $10K (3/26)
$489,999
3466 Middle Rd, Winchester, VA 22602
3beds
2,483sqft
Est.:
Single Family Residence
Built in 1975
0.59 Acres Lot
$492,700 Zestimate®
$197/sqft
$-- HOA
What's special
All-brick hillside homeBeautiful wood-burning fireplaceIn-home washer and dryerNew upper-level flooringOpen-concept designRefreshed landscapingExpansive living spaces
- 102 days |
- 5,211 |
- 209 |
Zillow last checked:
Listing updated:
Listed by:
Leslie Webb 540-303-3176,
Long & Foster Real Estate, Inc.
Source: Bright MLS,MLS#: VAFV2038362
Tour with a local agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 3
- Full bathrooms: 3
- Main level bathrooms: 2
- Main level bedrooms: 3
Basement
- Area: 379
Heating
- Heat Pump, Electric
Cooling
- Central Air, Electric
Appliances
- Included: Dishwasher, Disposal, Dryer, Exhaust Fan, Oven/Range - Electric, Refrigerator, Washer, Water Heater, Water Conditioner - Owned, Electric Water Heater
Features
- Breakfast Area, Ceiling Fan(s), Combination Kitchen/Living, Dining Area, Entry Level Bedroom, Eat-in Kitchen, Kitchen Island, Primary Bath(s), Upgraded Countertops, Walk-In Closet(s)
- Basement: Connecting Stairway,Full,Exterior Entry,Partially Finished,Side Entrance,Walk-Out Access
- Number of fireplaces: 1
- Fireplace features: Wood Burning
Interior area
- Total structure area: 2,483
- Total interior livable area: 2,483 sqft
- Finished area above ground: 2,104
- Finished area below ground: 379
Property
Parking
- Total spaces: 2
- Parking features: Storage, Garage Door Opener, Oversized, Garage Faces Rear, Inside Entrance, Asphalt, Attached, Off Street, On Street
- Attached garage spaces: 2
- Has uncovered spaces: Yes
Accessibility
- Accessibility features: Other
Features
- Levels: Two
- Stories: 2
- Exterior features: Lighting
- Pool features: None
- Has view: Yes
- View description: Mountain(s)
Lot
- Size: 0.59 Acres
Details
- Additional structures: Above Grade, Below Grade
- Parcel number: 62A311
- Zoning: RP
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Ranch/Rambler
- Property subtype: Single Family Residence
Materials
- Brick
- Foundation: Block
Condition
- New construction: No
- Year built: 1975
- Major remodel year: 2022
Utilities & green energy
- Sewer: On Site Septic
- Water: Conditioner, Well
Community & HOA
Community
- Subdivision: Jackson Woods Estates
HOA
- Has HOA: No
Location
- Region: Winchester
Financial & listing details
- Price per square foot: $197/sqft
- Tax assessed value: $480,800
- Annual tax amount: $2,308
- Date on market: 1/3/2026
- Listing agreement: Exclusive Right To Sell
- Ownership: Fee Simple
Estimated market value
$492,700
$468,000 - $517,000
$2,266/mo
Price history
Price history
| Date | Event | Price |
|---|---|---|
| 3/26/2026 | Price change | $489,999-2%$197/sqft |
Source:  Bright MLS #VAFV2038362 Report a problem | ||
| 3/18/2026 | Price change | $499,999-1.9%$201/sqft |
Source: Bright MLS #VAFV2038362 Report a problem | ||
| 3/6/2026 | Price change | $509,900-1.9%$205/sqft |
Source: Bright MLS #VAFV2038362 Report a problem | ||
| 2/19/2026 | Price change | $519,900-1%$209/sqft |
Source: Bright MLS #VAFV2038362 Report a problem | ||
| 2/10/2026 | Price change | $524,900-0.9%$211/sqft |
Source: Bright MLS #VAFV2038362 Report a problem | ||
| 1/21/2026 | Listed for sale | $529,900$213/sqft |
Source:  Long & Foster Broker Feed #VAFV2038362 Report a problem | ||
| 1/10/2026 | Pending sale | $529,900$213/sqft |
Source: Bright MLS #VAFV2038362 Report a problem | ||
| 1/3/2026 | Listed for sale | $529,900+30.8%$213/sqft |
Source: Bright MLS #VAFV2038362 Report a problem | ||
| 12/7/2023 | Listing removed | -- |
Source: Bright MLS #VAFV2002070 Report a problem | ||
| 8/1/2022 | Sold | $405,000+5.2%$163/sqft |
Source: Bright MLS #VAFV2007376 Report a problem | ||
| 6/28/2022 | Pending sale | $385,000$155/sqft |
Source: Bright MLS #VAFV2007376 Report a problem | ||
| 6/23/2022 | Listed for sale | $385,000+11%$155/sqft |
Source: Bright MLS #VAFV2007376 Report a problem | ||
| 12/6/2021 | Sold | $347,000-6%$140/sqft |
Source: Bright MLS #VAFV2002070 Report a problem | ||
| 10/14/2021 | Contingent | $369,000$149/sqft |
Source: Bright MLS #VAFV2002070 Report a problem | ||
| 10/8/2021 | Listed for sale | $369,000+27.2%$149/sqft |
Source: Bright MLS #VAFV2002070 Report a problem | ||
| 5/1/2020 | Sold | $290,000-9.1%$117/sqft |
Source: Public Record Report a problem | ||
| 3/12/2020 | Price change | $319,000-3%$128/sqft |
Source: Harmony Properties Real Estate, Inc. #VAFV155936 Report a problem | ||
| 2/26/2020 | Listed for sale | $329,000+9.7%$133/sqft |
Source: Harmony Properties Real Estate, Inc. #VAFV155936 Report a problem | ||
| 9/28/2018 | Sold | $300,000-7.7%$121/sqft |
Source: Long & Foster Broker Feed #1005182725_100 Report a problem | ||
| 9/16/2018 | Pending sale | $324,900$131/sqft |
Source: Long & Foster/Webber & Associates #1005182725 Report a problem | ||
| 7/23/2018 | Price change | $324,900-3%$131/sqft |
Source: Long & Foster/Webber & Associates #1005182725 Report a problem | ||
| 6/27/2018 | Price change | $334,900-1.5%$135/sqft |
Source: Long & Foster/Webber & Associates #1005182725 Report a problem | ||
| 4/3/2018 | Price change | $339,900-2.9%$137/sqft |
Source: Long & Foster/Webber & Associates #1005182725 Report a problem | ||
| 1/29/2018 | Listed for sale | $349,900+34.6%$141/sqft |
Source: Long & Foster/Webber & Associates #1005182725 Report a problem | ||
| 7/19/2016 | Sold | $259,900$105/sqft |
Source: Public Record Report a problem | ||
| 6/27/2016 | Pending sale | $259,900$105/sqft |
Source: ERA OakCrest Realty, Inc. #FV9645609 Report a problem | ||
| 6/7/2016 | Price change | $259,900-3.7%$105/sqft |
Source: ERA OakCrest Realty, Inc. #FV9645609 Report a problem | ||
| 5/5/2016 | Listed for sale | $269,900+63.6%$109/sqft |
Source: ERA OakCrest Realty, Inc. #FV9645609 Report a problem | ||
| 6/29/2009 | Sold | $165,000-34.8%$66/sqft |
Source: Public Record Report a problem | ||
| 6/23/2004 | Sold | $252,900$102/sqft |
Source: Public Record Report a problem | ||
Public tax history
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $2,308 +9% | $480,800 +15.8% |
| 2024 | $2,118 | $415,300 |
| 2023 | $2,118 +118.9% | $415,300 +30.9% |
| 2022 | $967 | $317,200 |
| 2021 | $967 -49.4% | $317,200 +1.2% |
| 2020 | $1,912 -50% | $313,500 |
| 2019 | $3,825 +99.1% | $313,500 -0.4% |
| 2018 | $1,921 +1.7% | $314,900 |
| 2017 | $1,889 +8% | $314,900 +8% |
| 2016 | $1,750 +7.1% | $291,700 |
| 2015 | $1,634 +123.7% | $291,700 +7.4% |
| 2014 | $730 | $271,700 |
| 2013 | -- | $271,700 +8.9% |
| 2012 | -- | $249,600 -8.9% |
| 2011 | -- | $274,100 -8.3% |
| 2010 | -- | $298,800 |
| 2009 | -- | $298,800 -1% |
| 2008 | -- | $301,700 |
| 2007 | -- | $301,700 |
| 2006 | -- | $301,700 |
| 2005 | -- | $301,700 +44.8% |
| 2003 | -- | $208,400 |
| 2002 | -- | $208,400 |
| 2001 | -- | $208,400 |
Find assessor info on the county website
Monthly payment
Est. payment
$2,541/mo
Principal & interest
$2370
Property taxes
$171
More affordability tools
Climate risks
Neighborhood: 22602
Nearby schools
GreatSchools rating
- 3/10Orchard View Elementary SchoolGrades: PK-5Distance: 1.6 mi
- 3/10James Wood Middle SchoolGrades: 6-8Distance: 3.8 mi
- 6/10Sherando High SchoolGrades: 9-12Distance: 4.7 mi
Schools provided by the listing agent
- District: Frederick County Public Schools
Source: Bright MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
A local agent can set up tours, give advice and negotiate with sellers.
A local lender can help you make sure your offer is ready when you are.
- Virginia
- Frederick County
- Winchester
- 22602
- 3466 Middle Rd
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