Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$299,999

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1,362 Sq. Ft.
  • Updated 12 days ago
See This Home
Save This Home
See This Home
Save This Home
Awesome Colonial Revival just four blocks from Winchester's beloved walking mall! This 1921 charmer has been completely transformed with a total make-over you'll love. Brand new stainless steel appliances make cooking a joy, while fresh vinyl laminate flooring flows throughout for easy living. New LED fixtures brighten every room, and classy bathroom updates add that spa-like touch. Tucked away on a quiet one-way street, you get the best of both worlds - peaceful neighborhood living with downtown walkability, in an up and coming neighborhood. Three comfortable bedrooms and two full baths give your family room to spread out. No HOA means more freedom and money in your pocket every month. Move-in ready and waiting for you to make it home. EXCLUSIVE BENEFITS WITH THIS HOME: "¢ First Responder & Military Appreciation Discount - saves you thousands! "¢ 12-Month Home Warranty included for extra peace of mind "¢ 24-Month Satisfaction Guarantee - if you're not happy, we'll buy it back or sell it for free!* "¢ 24-Hour Open House - Call for Times!

Full Property Details for 553 Highland Ave

General

  • Price: $299,999
  • Taxes: $1,211 (2025)
  • Status: Active
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: VAWI2009182
  • Updated: 5/22/2026
  • Added to Site: 243 day(s) ago

Interior

  • Number of Rooms: 8
  • Appliances: Built-In Microwave, Dishwasher, Washer, Dryer, Stove, Refrigerator, Stainless Steel Appliances, Oven - Double, Water Heater

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2
  • Main Floor Baths: 2
  • Main - Full Baths: 2

Bedrooms

  • Total Bedrooms: 3
  • Bedrooms Main & Up: 3

Other Rooms

  • Laundry: Has Laundry

Additional Information

  • Security/Safety: Smoke Detector

Exterior

  • Exterior Features: Outbuilding(s), Secure Storage
  • Porch/Patio/Deck: Porch(es)

Parking

  • Total Spaces: 1
  • Parking Features: Crushed Stone, Fenced
  • Parking Type: Alley, On Street, Driveway

Location

  • County: WINCHESTER CITY
  • Driving Directions: From Liberty Avenue, turn onto Highland Avenue and the house will be on your right. Highland is a one way street, so you need to enter at Liberty.

School Information

  • School District: Winchester City Public Schools
  • Elementary School: Virginia Avenue Charlotte Dehart
  • Middle School: Daniel Morgan
  • High School: John Handley

Heating & Cooling

  • Cooling Type: Ductless/Mini-Split
  • Cooling Fuel: Electric
  • Heating Type: Other, Programmable Thermostat
  • Heating Fuel: Electric
  • Water Heater: Electric

Utilities

  • Sewer: Public Sewer
  • Water: Public

Structural Information

  • Architectural Style: Traditional
  • Structure Type: Detached
  • Construction: Combination
  • Foundation: Concrete Perimeter
  • Roof: Metal
  • Windows: Energy Efficient, Screens, Vinyl Clad
  • Stories Description: Main
  • Square Feet: 1,362
  • Sq. Ft. Source: Estimated
  • Living Area: 1,362 Sq. Ft.
  • Finished Above Grnd: 1,362 Sq. Ft.
  • Year Built: 1921
  • Year Built Source: Estimated

Lot Features

  • Lot Size (Acres): 0.09
  • Lot Size (Sq. Ft.): 3,920
  • Lot Size Source: Estimated
  • Zoning: HR1
  • Lot Description: Private, Rear Yard
  • Fencing (Description): Board, Masonry/Stone

Green Features

  • Energy Efficient: Appliances

Financial Considerations

  • Price Per Sq. Ft.: $220.26
  • Assessment Year: 2025
  • Tax w/Assessment: $152,300
  • Tax Amount: $1,211
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple

Listed by Your Home Sold Guaranteed Realty - East LLC, Teri Domanski

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

Listing agent

— 553 Highland Ave —

  • Teri Domanski

    Your Home Sold Guaranteed Realty - East LLC

Listing Office Email: jp@yhsgrtn.com

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 553 Highland Ave

School District:Winchester City Public Schools
NameGradesDistance
Virginia Ave. Charlotte Dehart Elementary School
550 Virginia Avenue, Winchester, VA 22601
PK-40.3 mi
Daniel Morgan Middle School
48 South Purcell Avenue, Winchester, VA 22601
7-80.9 mi
John Handley High School
425 Handley Boulevard, Winchester, VA 22601
9-121.4 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 553 Highland Ave Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/22/2026
Price Reduced
$299,999
-5.96%
MLS
1/02/2026
Price Reduced
$319,000
-1.24%
MLS
12/05/2025
Price Reduced
$323,000
-3.29%
MLS
10/30/2025
Price Reduced
$334,000
-0.3%
MLS
10/03/2025
Listed
$335,000
134.27%
MLS
9/06/2024
Sold
$143,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 553 Highland Ave

Year
Property Taxes
Change
Tax Assessment
Change
2025
$1,211
100%
$152,300
13%
2024
-100%
$134,800
—
2023
$1,119
20%
$134,800
34%
2022
$936
—
$100,600
—
2021
$936
20%
$100,600
20%
2020
$777
—
$83,500
—
2018
$777
7%
$83,500
5%
2018
$726
15%
$79,800
—
2016
$632
—
$79,800
15%
2016
$632
—
$69,500
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 553 Highland Ave

$
Down Payment
%
$
%

$
$

*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Your Home Sold Guaranteed Realty - East LLC, Teri Domanski

Similar Properties near 553 Highland Ave

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

406 Highland Ave, Winchester, VA 22601 - Photo 1 Price Reduced
-$10,510 (-3.38%)
$299,990
Open House

406 Highland Ave  Winchester, VA 22601

  • Single Family
  • Active
  • Updated 3 hours ago
  • 3
    Beds
  • 2
    Total Baths
  • 2,211
    Sq. Ft.
Listed by Century 21 Redwood Realty, Lisette B. Turner
105 Buckskin Trail, Winchester, VA 22602 - Photo 1 Price Reduced
-$5,100 (-1.67%)
$299,900

105 Buckskin Trail  Winchester, VA 22602

  • Single Family
  • Active
  • Updated 2 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,100
    Sq. Ft.
Listed by Long & Foster Real Estate, Inc., Bruce A Elsey
115 Hickory Ln, Winchester, VA 22603 - Photo 1 Just Listed
$299,000

115 Hickory Ln  Winchester, VA 22603

  • Single Family
  • Active
  • Updated 5 hours ago
  • 2
    Beds
  • 1
    Total Bath
  • 1,643
    Sq. Ft.
Listed by ERA Oakcrest Realty, Inc., Tiffany J Hunter and ERA Oakcrest Realty, Inc., Tracie Clawson
580 York Ave, Winchester, VA 22601 - Photo 1
$290,000

580 York Ave  Winchester, VA 22601

  • Single Family
  • Active
  • Updated 11 days ago
  • 2
    Beds
  • 1
    Total Bath
  • 817
    Sq. Ft.
Listed by The Vasquez Group LLC, Yoselin P Mejia

Just Listed near 553 Highland Ave

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

108 Reedville Ct, Stephens City, VA 22655 - Photo 1 Just Listed
$639,900
Open House

108 Reedville Ct  Stephens City, VA 22655

  • Single Family
  • Active
  • Updated 10 hours ago
  • 4
    Beds
  • 4
    Total Baths
  • 4,733
    Sq. Ft.
Listed by RE/MAX Roots, Roxanna D Grimes
102 Romney Pl, Stephens City, VA 22655 - Photo 1 Price Reduced
-$5 (0%)
$399,895

102 Romney Pl  Stephens City, VA 22655

  • Single Family
  • Active
  • Updated 4 hours ago
  • 5
    Beds
  • 3
    Total Baths
  • 2,360
    Sq. Ft.
Listed by ANR Realty, LLC, Ana Lucia Ron
1286 Macedonia Church Rd, Stephens City, VA 22655 - Photo 1 Just Listed
$519,000

1286 Macedonia Church Rd  Stephens City, VA 22655

  • Single Family
  • Active
  • Updated 2 days ago
  • 4
    Beds
  • 4
    Total Baths
  • 2,824
    Sq. Ft.
Listed by Colony Realty, Daniel J Whitacre
105 Lemley Dr, Stephens City, VA 22655 - Photo 1 Just Listed
$569,990

105 Lemley Dr  Stephens City, VA 22655

  • Single Family
  • Active
  • Updated 5 days ago
  • 5
    Beds
  • 4
    Total Baths
  • 3,127
    Sq. Ft.
Listed by D R Horton Realty of Virginia LLC, Victoria Jane Clark

Price Reduced near 553 Highland Ave

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

102 Romney Pl, Stephens City, VA 22655 - Photo 1 Price Reduced
-$5 (0%)
$399,895

102 Romney Pl  Stephens City, VA 22655

  • Single Family
  • Active
  • Updated 4 hours ago
  • 5
    Beds
  • 3
    Total Baths
  • 2,360
    Sq. Ft.
Listed by ANR Realty, LLC, Ana Lucia Ron
107 Oak Ridge Dr, Stephens City, VA 22655 - Photo 1 Price Reduced
-$5,100 (-1.05%)
$479,900
Open House

107 Oak Ridge Dr  Stephens City, VA 22655

  • Single Family
  • Active
  • Updated 1 day ago
  • 4
    Beds
  • 3
    Total Baths
  • 3,184
    Sq. Ft.
Listed by Coldwell Banker Premier, Stuart A Sinclair
120 Bookers Crst Dr, Stephens City, VA 22655 - Photo 1 Price Reduced
-$15,000 (-3.16%)
$459,990
Open House

120 Bookers Crst Dr  Stephens City, VA 22655

  • Single Family
  • Active
  • Updated 1 day ago
  • 4
    Beds
  • 3
    Total Baths
  • 1,906
    Sq. Ft.
Listed by D R Horton Realty of Virginia LLC, Victoria Jane Clark
101 Southdown Cir, Stephens City, VA 22655 - Photo 1 Price Reduced
-$10,000 (-2.22%)
$439,500

101 Southdown Cir  Stephens City, VA 22655

  • Single Family
  • Active
  • Updated 3 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 1,912
    Sq. Ft.
Listed by Dream Real Estate, Mary A Casselano and Dream Real Estate, Samuel H Smith Jr.

Recent Sales near 553 Highland Ave

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

424 Highland Ave, Winchester, VA 22601 - Photo 1 Sold
$279,000

424 Highland Ave  Winchester, VA 22601

  • Single Family
  • Closed
  • 2
    Beds
  • 1
    Total Bath
  • 759
    Sq. Ft.
Listed by Long & Foster Real Estate, Inc., Jacqueline Hitchcock
Sold by Nova Home Hunters Realty, Charles Witt
423 Highland Ave, Winchester, VA 22601 - Photo 1 Sold
$270,000

423 Highland Ave  Winchester, VA 22601

  • Single Family
  • Closed
  • 3
    Beds
  • 2
    Total Baths
  • 1,300
    Sq. Ft.
Listed by Samson Properties, Carlos da Rocha Soares Sr.
Sold by Vaze Realty, Beltmarys del Milagro Rodriguez Sposito
621 Butler Ave, Winchester, VA 22601 - Photo 1 Sold
$300,000

621 Butler Ave  Winchester, VA 22601

  • Single Family
  • Closed
  • 4
    Beds
  • 2
    Total Baths
  • 1,803
    Sq. Ft.
Listed by RE/MAX Roots, Kaitlyn Behr
Sold by Five Star Real Estate, Justin Goodman
625 Watson Ave, Winchester, VA 22601 - Photo 1 Sold
$299,900

625 Watson Ave  Winchester, VA 22601

  • Single Family
  • Closed
  • Updated 6 days ago
  • 3
    Beds
  • 1
    Total Bath
  • 1,806
    Sq. Ft.
Listed by RE/MAX Roots, Jennifer Sacco
Sold by RE/MAX Real Estate Connections, Renzo C Falla

553 Highland Avenue, Winchester, VA 22601 (MLS# VAWI2009182) is a Single Family property with 3 bedrooms and 2 full bathrooms. 553 Highland Avenue is currently listed for $299,999 and was received on October 03, 2025. Want to learn more about 553 Highland Avenue? Do you have questions about finding other Single Family real estate for sale in Winchester? You can browse all Winchester real estate or contact a Coldwell Banker agent to request more information.

Tour this property