3466 Middle Road

Closed 5/20/26

Sold

Last Sold Price

$465,000

3 beds3 baths2,483 sqft

3466 Middle Rd, Winchester, VA 22602

Single FamilyProperty Type

0.59 acresLot Size

1975Year Built

$187/sq ftPrice per sq ft

2 carsParking Spaces

Description

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...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.

Listed by: Leslie A. Webb 540.303.3176 leslie.webb@longandfoster.com • Long & Foster Real Estate, Inc.

Listing closed: 05/20/2026 12:00 AM • Source: BRIGHT, MLS#: VAFV2038362

Get preapproved with Rocket Mortgage¹

Location

Listing Courtesy of Long & Foster Real Estate, Inc.

Sold By Pearson Smith Realty, LLC

Add your commute

Payment Calculator

Get preapproved with
OriginPoint Mortgage or Rocket Mortgage¹

$2,595 per month

30 year fixed, 6.71% Interest

Principal and Interest

$2,403

Property Taxes

$192

HOA Dues

The Payment Calculator is for illustrative purposes only.

Know your buying power with a preapproval and custom rate in minutes

Property Information for 3466 Middle Road

Property Details

Taxes: $2,308 / year
MLS Type: Residential / Fee Simple
County: Frederick County, VA
Tax ID Number: 62-A-3-1-1
Ownership: Fee Simple
Condo Coop Association: No
HOA: No
Structure Type: Detached
Style: Ranch/Rambler
Levels/Stories: 2
Waterfront: No
Views: Mountain
Garage: Yes
Subdivision: JACKSON WOODS ESTATES
Subdivision: JACKSON WOODS ESTATES (FREDERICK VA)
Legal Subdivision: JACKSON WOODS ESTATES
Total Parking Spaces: 2
Central Air: Yes
Basement: Yes
Above Grade Finished SQFT: 2,104.00
Above Grade Fin SQFT Source: Estimated
Below Grade Finished SQFT: 379.00
Below Grade Fin SQFT Source: Estimated
Below Grade Unfinished SQFT: .00
Below Grade Unfin SQFT Source: Estimated
Total Below Grade SQFT: 379.00
Total Below Grade SQFT Source: Estimated
New Construction: No

Building Information

Stories: 2
Year Built: 1975
Lot Size: 0.59 AC / 25,700 SF

Location

In City Limits: No
School District Name: FREDERICK COUNTY PUBLIC SCHOOLS

School District County ID: 121140907577
SchoolDistrictSource: Listing Agent
County: FREDERICK

Waterfront / Water Access

Water View: No
Water Access: No

Water Oriented: No
Navigable Water: No
Tidal Water: No
Riparian Rights Y/N: No

Association / Community Info

Senior Community: No

Taxes and Assessment

Tax Year: 2025
Tax Assessed Value: $480,800

Year Assessed: 2025
County Tax: $2,308
Improvement Assessed Value: $362,800
City Town Tax: $0
Land Assessed Value: $118,000
Clean Green Assessed: No
Land Use Code: 200R
Zoning: RP
Tax Lot: 1
School Tax: $0
Automatically Update Tax Values Y/N: Yes

Rooms

Main

# Bedrooms Count Main Level: 3
# Bathrooms Count Main Level: 2

# Bathrooms Full Main Level: 2

All Lower Levels

# Bathrooms All Lower Levels: 1
# Bathrooms Full All Lower Levels: 1

Lower Level 1

# Bathrooms Lower Level: 1
# Bathrooms Full Lower Level: 1

Rooms

Stories: Lower 1, Main

Building Info

Year Major Reno Remodel: 2022
Total Finished SQFT: 2,483.00

Total Finished SQFT Source: Estimated
Tax Total Finished SQFT: 2,068.00
Total SQFT: 2,483.00
Total SQFT Source: Estimated
Construction Materials: Brick
Ext Main Mid-res: http://bright-media01.prd.brightmls.com/bright/images/0000/8047/4711/4424/804747114424_512_384_WM_5Mlhw5vtv-i1JJs_.jpg
Basement Type: Connecting Stairway, Full, Outside Entrance, Partially Finished, Side Entrance, Walkout Stairs
Foundation Details: Block
Room and Floor: Bedrooms-Main Level-1, Bedrooms-Main Level-2, Bedrooms-Main Level-3, Bathrooms Full-Main Level-1, Bathrooms Full-Main Level-2, Bathrooms Full-Lower Level 1-1
# Bathrooms Full: 3
Other Structure: Above Grade, Below Grade

Lot / Land Information

Lot Size Source: Estimated
Parcel ID: 18794515

Parking

Type Of Parking: Attached Garage, Off Street, On Street
Num of Attached Garage Spaces: 2

Total Garage Spaces: 2
Parking Features: Asphalt Driveway
Garage Features: Additional Storage Area, Garage Door Opener, Oversized, Garage - Rear Entry, Inside Access

Interior Features

Interior Features: Breakfast Area, Ceiling Fan(s), Combination Kitchen/Living, Dining Area, Entry Level Bedroom, Kitchen - Eat-In, Kitchen - Island, Primary Bath(s), Upgraded Countertops, Walk-in Closet(s)
Fireplace: Yes

Fireplaces Count: 1
Fireplace Features: Wood
Appliances: Dishwasher, Disposal, Dryer, Exhaust Fan, Oven/Range - Electric, Refrigerator, Washer, Water Heater, Water Conditioner - Owned
Accessibility Features: Other

Exterior Features

Exterior Features: Exterior Lighting
Pool: No Pool

Utilities

Heating: Yes
Cooling Type: Central A/C

Cooling Fuel: Electric
Heating Type: Heat Pump(s)
Heating Fuel: Electric
Hot Water: Electric
Water Source: Conditioner, Well
Sewer Septic: On Site Septic

Confidential Data

Listing Office

List Agent AOR: Blue Ridge Association of REALTORS
List Agent URL: www.lesliewebb.lnf.com

Property History for 3466 Middle Road

Date	Event & Source	Price	Appreciation
May 20, 2026	Closed BRIGHT #VAFV2038362	$465,000	—
May 19, 2026	Closed (Public Record) Public Record #1940158152	$465,000	+8.1% / yr
Apr 19, 2026	Pending BRIGHT #VAFV2038362		—
Apr 19, 2026	Active Under Contract BRIGHT #VAFV2038362		—
Mar 26, 2026	Price Change BRIGHT #VAFV2038362	$489,999	—
Mar 18, 2026	Price Change BRIGHT #VAFV2038362	$499,999	—
Mar 5, 2026	Price Change BRIGHT #VAFV2038362	$509,900	—
Feb 19, 2026	Price Change BRIGHT #VAFV2038362	$519,900	—
Feb 10, 2026	Price Change BRIGHT #VAFV2038362	$524,900	—
Jan 21, 2026	Listed (Active) BRIGHT #VAFV2038362	$529,900	—
Jan 10, 2026	Pending BRIGHT #VAFV2038362		—
Jan 3, 2026	Listed (Active) BRIGHT #VAFV2038362	$529,900	—
Aug 1, 2022	Closed BRIGHT #VAFV2007376	$405,000	—
Aug 1, 2022	Closed Williamsburg Multiple Listing Service #BMTVAFV2007376	$405,000	—
Jun 27, 2022	Pending BRIGHT #VAFV2007376		—
Jun 23, 2022	Listed (Active) BRIGHT #VAFV2007376	$385,000	—
Jun 15, 2022	Listed (Active) Williamsburg Multiple Listing Service #BMTVAFV2007376	$385,000	—
Dec 6, 2021	Closed BRIGHT #VAFV2002070	$347,000	—
Oct 14, 2021	Active Under Contract BRIGHT #VAFV2002070		—
Oct 14, 2021	Pending BRIGHT #VAFV2002070		—
Oct 14, 2021	Active Under Contract BRIGHT #VAFV2002070		—
Oct 8, 2021	Listed (Active) BRIGHT #VAFV2002070	$369,000	—
May 1, 2020	Expired BRIGHT #VAFV155936	$319,000	—
Apr 22, 2020	Closed (Public Record) Public Record #668031902	$290,000	-2.1% / yr
Apr 17, 2020	Withdrawn BRIGHT #VAFV155936	$319,000	—
Feb 26, 2020	Listed (Active) BRIGHT #VAFV155936	$329,000	—
Sep 28, 2018	Closed (Public Record) Public Record #631931733	$300,000	+6.8% / yr
Sep 28, 2018	Closed BRIGHT #1005182725	$300,000	—
Sep 15, 2018	Pending BRIGHT #1005182725		—
Jan 29, 2018	Listed (Active) BRIGHT #1005182725	$349,900	—
Jul 18, 2016	Closed (Public Record) Public Record #582408575	$259,900	+6.6% / yr
Jul 18, 2016	Closed BRIGHT #1001327701	$259,900	—
Jun 16, 2016	Pending BRIGHT #1001327701		—
May 3, 2016	Listed (Active) BRIGHT #1001327701	$269,900	—
Jul 31, 2014	Withdrawn BRIGHT #1007565246		—
Jun 12, 2014	Withdrawn BRIGHT #1007565246	$249,900	—
Jan 22, 2014	Listed (Active) BRIGHT #1007565246	$269,900	—
Jun 26, 2009	Closed (Public Record) Public Record #281955609	$165,000	-8.2% / yr
Apr 16, 2008	Withdrawn BRIGHT #VAFV138498	$279,000	—
Apr 16, 2008	Withdrawn BRIGHT #VAFV138498		—
Jun 20, 2007	Listed (Active) BRIGHT #VAFV138498	$314,900	—
Jun 23, 2004	Closed (Public Record) Public Record #541382898	$252,900	—
Jun 22, 2004	Closed BRIGHT #VAFV117458	$252,900	—
Feb 7, 2004	Pending BRIGHT #VAFV117458		—
Dec 19, 2003	Withdrawn BRIGHT #VAFV143472		—
Dec 19, 2003	Listed (Active) BRIGHT #VAFV117458	$259,900	—
Jul 8, 2003	Withdrawn BRIGHT #VAFV143254	$219,900	—
Jul 8, 2003	Listed (Active) BRIGHT #VAFV143472	$259,900	—
Apr 2, 2003	Listed (Active) BRIGHT #VAFV143254	$219,900	—
Nov 10, 1999	Closed BRIGHT #VAFV122624	$145,000	—
Nov 10, 1999	Pending BRIGHT #VAFV122624		—
Sep 7, 1999	Listed (Active) BRIGHT #VAFV122624	$154,900	—
Aug 30, 1999	Expired BRIGHT #VAFV130084	$154,900	—
Mar 28, 1999	Listed (Active) BRIGHT #VAFV130084	$154,900	—
Feb 20, 1999	Expired BRIGHT #VAFV130806	$154,900	—
Jan 19, 1999	Listed (Active) BRIGHT #VAFV130806	$154,900	—
Dec 14, 1998	Expired BRIGHT #VAFV130390	$159,900	—
Jul 17, 1998	Closed MLS Now #93800290	$17,900	—
Jul 16, 1998	Expired BRIGHT #VAFV130688	$159,900	—
Jul 14, 1998	Listed (Active) BRIGHT #VAFV130390	$159,900	—
Apr 20, 1998	Listed (Active) MLS Now #93800290	$17,500	—
Oct 7, 1997	Listed (Active) BRIGHT #VAFV130688	$164,900	—

Date	Event & Source	Price
05/20/2026	Closed BRIGHT #VAFV2038362	$465,000
05/19/2026	Closed (Public Record) Public Record #1940158152	$465,000 +8.1% / yr
04/19/2026	Pending BRIGHT #VAFV2038362	—
04/19/2026	Active Under Contract BRIGHT #VAFV2038362	—
03/26/2026	Price Change BRIGHT #VAFV2038362	$489,999
03/18/2026	Price Change BRIGHT #VAFV2038362	$499,999
03/05/2026	Price Change BRIGHT #VAFV2038362	$509,900
02/19/2026	Price Change BRIGHT #VAFV2038362	$519,900
02/10/2026	Price Change BRIGHT #VAFV2038362	$524,900
01/21/2026	Listed (Active) BRIGHT #VAFV2038362	$529,900
01/10/2026	Pending BRIGHT #VAFV2038362	—
01/03/2026	Listed (Active) BRIGHT #VAFV2038362	$529,900
08/01/2022	Closed BRIGHT #VAFV2007376	$405,000
08/01/2022	Closed Williamsburg Multiple Listing Service #BMTVAFV2007376	$405,000
06/27/2022	Pending BRIGHT #VAFV2007376	—
06/23/2022	Listed (Active) BRIGHT #VAFV2007376	$385,000
06/15/2022	Listed (Active) Williamsburg Multiple Listing Service #BMTVAFV2007376	$385,000
12/06/2021	Closed BRIGHT #VAFV2002070	$347,000
10/14/2021	Active Under Contract BRIGHT #VAFV2002070	—
10/14/2021	Pending BRIGHT #VAFV2002070	—
10/14/2021	Active Under Contract BRIGHT #VAFV2002070	—
10/08/2021	Listed (Active) BRIGHT #VAFV2002070	$369,000
05/01/2020	Expired BRIGHT #VAFV155936	$319,000
04/22/2020	Closed (Public Record) Public Record #668031902	$290,000 -2.1% / yr
04/17/2020	Withdrawn BRIGHT #VAFV155936	$319,000
02/26/2020	Listed (Active) BRIGHT #VAFV155936	$329,000
09/28/2018	Closed (Public Record) Public Record #631931733	$300,000 +6.8% / yr
09/28/2018	Closed BRIGHT #1005182725	$300,000
09/15/2018	Pending BRIGHT #1005182725	—
01/29/2018	Listed (Active) BRIGHT #1005182725	$349,900
07/18/2016	Closed (Public Record) Public Record #582408575	$259,900 +6.6% / yr
07/18/2016	Closed BRIGHT #1001327701	$259,900
06/16/2016	Pending BRIGHT #1001327701	—
05/03/2016	Listed (Active) BRIGHT #1001327701	$269,900
07/31/2014	Withdrawn BRIGHT #1007565246	—
06/12/2014	Withdrawn BRIGHT #1007565246	$249,900
01/22/2014	Listed (Active) BRIGHT #1007565246	$269,900
06/26/2009	Closed (Public Record) Public Record #281955609	$165,000 -8.2% / yr
04/16/2008	Withdrawn BRIGHT #VAFV138498	$279,000
04/16/2008	Withdrawn BRIGHT #VAFV138498	—
06/20/2007	Listed (Active) BRIGHT #VAFV138498	$314,900
06/23/2004	Closed (Public Record) Public Record #541382898	$252,900
06/22/2004	Closed BRIGHT #VAFV117458	$252,900
02/07/2004	Pending BRIGHT #VAFV117458	—
12/19/2003	Withdrawn BRIGHT #VAFV143472	—
12/19/2003	Listed (Active) BRIGHT #VAFV117458	$259,900
07/08/2003	Withdrawn BRIGHT #VAFV143254	$219,900
07/08/2003	Listed (Active) BRIGHT #VAFV143472	$259,900
04/02/2003	Listed (Active) BRIGHT #VAFV143254	$219,900
11/10/1999	Closed BRIGHT #VAFV122624	$145,000
11/10/1999	Pending BRIGHT #VAFV122624	—
09/07/1999	Listed (Active) BRIGHT #VAFV122624	$154,900
08/30/1999	Expired BRIGHT #VAFV130084	$154,900
03/28/1999	Listed (Active) BRIGHT #VAFV130084	$154,900
02/20/1999	Expired BRIGHT #VAFV130806	$154,900
01/19/1999	Listed (Active) BRIGHT #VAFV130806	$154,900
12/14/1998	Expired BRIGHT #VAFV130390	$159,900
07/17/1998	Closed MLS Now #93800290	$17,900
07/16/1998	Expired BRIGHT #VAFV130688	$159,900
07/14/1998	Listed (Active) BRIGHT #VAFV130390	$159,900
04/20/1998	Listed (Active) MLS Now #93800290	$17,500
10/07/1997	Listed (Active) BRIGHT #VAFV130688	$164,900

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 3466 Middle Road

Taxable ValueLand$118,000Additions$362,800Total$480,800

Tax Record2026$2,548 ($212 / month)

Home Facts

Beds3Baths3Total Finished SqFt3,582 SqFtAbove Grade Finished SqFt1,688 SqFtFinished Basement SqFt1,894 SqFtStories1Lot Size24,276 SqFtStyleSingle Family ResidenceYear Built1975Year Renovated2007ZoningRPCountyFREDERICKAPN62A3-1-1

Schools near 3466 Middle Road

This home is within Frederick County Public Schools.


Rating	School	Type	Grades	Distance
3/10	Orchard View Elementary School	Public - Serves this home	PK to 5	1.6 mi
3/10	James Wood Middle School	Public - Serves this home	6 to 8	3.8 mi
4/10	Sherando High School	Public - Serves this home	9 to 12	4.6 mi


Rating	School	Distance
3/10	Orchard View Elementary School PublicPK to 5 Serves this home	1.6 mi
3/10	James Wood Middle School Public6 to 8 Serves this home	3.8 mi
4/10	Sherando High School Public9 to 12 Serves this home	4.6 mi

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

Similar Homes

New listings in 22602

$635,000 | 104 Yarrow Court, Winchester, VA 22602

1/71

Open: 9/19 10:00AM - 01:00PMNew

$635,000

4
Bedrooms: 3
Bathrooms: 3,437
Square Feet: 0.27
Acres

104 Yarrow Court, Winchester, VA 22602

$629,900 | 222 Summerfield Drive, Winchester, VA 22602

1/52

Open: 9/20 12:00PM - 02:00PMNew

$629,900

3
Bedrooms: 2
Bathrooms: 2,077
Square Feet: 0.28
Acres

222 Summerfield Drive, Winchester, VA 22602

1/29

New

$317,265

3
Bedrooms: 2
Bathrooms: 1,550
Square Feet: Unavailable
Acres

148 Doe Trail, Winchester, VA 22602

$479,900 | 109 Julee Drive, Winchester, VA 22602

1/49

New

$479,900

5
Bedrooms: 3
Bathrooms: 3,276
Square Feet: 0.20
Acres

109 Julee Drive, Winchester, VA 22602

Coming Soon

$225,000

3
Bedrooms: 1
Bathrooms: 1,008
Square Feet: Unavailable
Acres

310 Crest Circle, Winchester, VA 22602

$539,900 | 114 Settlers Circle, Winchester, VA 22602

1/76

New

$539,900

5
Bedrooms: 4
Bathrooms: 3,290
Square Feet: 0.32
Acres

114 Settlers Circle, Winchester, VA 22602

$525,000 | 322 Lehigh Drive, Winchester, VA 22602

1/27

Coming Soon

$525,000

3
Bedrooms: 2
Bathrooms: 1,823
Square Feet: 0.26
Acres

322 Lehigh Drive, Winchester, VA 22602

$625,000 | 220 Greenfield Avenue, Winchester, VA 22602

1/11

Coming Soon

$625,000

3
Bedrooms: 2
Bathrooms: 2,260
Square Feet: 1
Acres

220 Greenfield Avenue, Winchester, VA 22602

$389,160 | 141 Sioux Loop, Winchester, VA 22602

1/44

NewNew Construction

$389,160

4
Bedrooms: 4
Bathrooms: 1,889
Square Feet: 0.04
Acres

141 Sioux Loop, Winchester, VA 22602

Nearby home values

Address	Sold price	Beds	Baths	Sqft	Lot (Sqft)
This home: 3466 Middle Road, Winchester, VA 22602	$465,000	3	3	2,483	25,700
101 Stuart Drive, Winchester, VA 22602	–	3	3	2,590	21,758
163 Stuart Drive, Winchester, VA 22602	$379,900	3	3	2,972	18,295
164 Stuart Drive, Winchester, VA 22602	$297,000	4	3	2,645	26,812
162 Stuart Drive, Winchester, VA 22602	–	3	2	1,568	25,330
105 Stuart Drive, Winchester, VA 22602	$205,000	3	2	1,902	0
160 Stuart Drive, Winchester, VA 22602	$215,000	2	2	1,662	0
104 Stuart Drive, Winchester, VA 22602	$435,000	3	2	2,200	24,394
156 Stuart Drive, Winchester, VA 22602	$437,500	3	4	4,402	43,560
106 Stuart Drive, Winchester, VA 22602	–	3	2.5	1,792	24,647
2641 Jones Road, Winchester, VA 22602	$250,000	3	2	1,447	23,529
157 Stuart Drive, Winchester, VA 22602	$270,000	3	3	2,593	26,136
115 Stuart Drive, Winchester, VA 22602	–	3	3	2,173	43,560
3426 Middle Road, Winchester, VA 22602	$535,000	5	3.5	4,230	70,567
2631 Jones Road, Winchester, VA 22602	$275,000	2	2	952	21,628
155 Stuart Drive, Winchester, VA 22602	$320,000	3	4	3,402	0

Explore Nearby Homes

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Long & Foster Real Estate, Inc.

© 2026 Bright MLS. All rights reserved. All information is deemed reliable, but accuracy is not guaranteed. Listing information is from various brokers who participate in IDX and not all listings may be visible on the site. The property information being provided is for the consumer’s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated on 05/20/2026 09:27 PM

Know your buying power with a preapproval and custom rate in minutes

Explore Nearby Homes

Homes in Nearby 22602 Neighborhoods

Homes in Nearby 22602 Cities

Homes in Nearby 22602 Zip Codes