519 Fairmont Ave, Winchester, VA 22601
Local realty services provided by:Better Homes and Gardens Real Estate Community Realty
Listed by: hannah won, kristin jenkins crockett
Office: samson properties
MLS#:VAWI2010814
Source:BRIGHTMLS
Price summary
- Price:$349,990
- Price per sq. ft.:$166.5
About this home
Expect a long love affair with this home.
Some homes feel like they were built with patience, pride, and a sense of permanence—and this historic Winchester beauty has that feeling the moment you step inside. Set near Old Town Winchester and positioned right next to the approved Cider Hill Neighborhood Design District, it offers something rare: preserved historic character today, with a front-row seat to one of Winchester’s most exciting visions for tomorrow.
Inside, tall ceilings give the rooms an airy, gracious presence, while the preserved woodwork around the door frames and staircases brings in the kind of craftsmanship that is nearly impossible to recreate. Every doorway feels intentional. Every turn of the staircase reminds you this home has a story. Even better, the home features two staircases, plus an additional staircase leading to the attic—an uncommon old-house detail that adds character, convenience, and intriguing future flexibility. The attic offers potential for a finished loft or creative bonus space later, subject to buyer due diligence, permits, and approvals.
With 3 bedrooms and 1 full bath, the home feels warm, grounded, and refreshingly authentic—never cookie-cutter, never stripped of its soul. The kitchen has been refreshed with new drywall and pendant lighting in 2026, adding a clean, current touch while still letting the home’s original personality shine. The bathroom was recently remodeled in 2026, electrical has been updated, new plumbing pipes were run in 2024, and the windows have been replaced within the last three years. The roof was replaced in 2021, the upstairs HVAC was replaced in 2019, and a new hot water heater was installed in 2026. These are the improvements that matter: the ones that help you enjoy the tall ceilings, old-house texture, and beautiful woodwork with added confidence.
The back of the home is just as inviting. Dual rear porches create two easy places to start the morning, wind down in the evening, or enjoy the backyard from a shaded perch. Beyond them, a generous 20 by 20 patio gives you room for outdoor dining, container gardens, a firepit setup, or a relaxed weekend gathering space. The flat lot keeps the yard practical and flexible, with open space that feels simple to use and easy to enjoy.
The location is where this home becomes especially compelling. Old Town Winchester is known for its local dining, shopping, events, museums, and attractions, giving the surrounding area a lively historic-downtown feel. First Fridays bring local artists, live music, sip-and-stroll energy, and special events to the heart of Old Town. Jim Barnett Park adds more than 170 acres of green space and amenities, while the Museum of the Shenandoah Valley offers galleries, gardens, and daily trail access.
Then add Cider Hill. The City of Winchester describes the Cider Hill Neighborhood Design District as an approved future vision focused on revitalizing a historically industrial area into a vibrant mixed-use community through adaptive reuse, enhanced connectivity, and a balance of residential, commercial, and public spaces. In plain language, that means this home is positioned beside an area planned to become more active, more connected, and more useful over time—placing it in the middle of several attractive Winchester destinations as the district evolves.
That combination is hard to duplicate: historic architecture, meaningful updates, outdoor living, a flat backyard, proximity to Old Town, adjacency to a planned mixed-use district, two staircases, and attic access with future upside. This is not a house trying to look historic. It is the real thing, with height, texture, craftsmanship, porches, and practical improvements already in place.
For anyone hoping to find a home with genuine old-house warmth near Winchester’s historic core—and near a city-backed district with a bold future vision—this one is easy to love and hard to forget. Owner is an inactive Virginia realtor....
Contact an agent
Home facts
- Year built:1900
- Subdivision & Development:HISTORIC DOWNTOWN WINCHESTER
- Listing ID #:VAWI2010814
- Added:65 day(s) ago
- Updated:August 07, 2026 at 07:53 AM
Rooms and interior
- Bedrooms:3
- Total bathrooms:1
- Full bathrooms:1
- Dining Description:Dining Area
- Kitchen Description:Built-Ins, Crown Moldings, Dishwasher, Double/Dual Staircase, Oven/Range - Electric, Refrigerator
- Basement:Yes
- Basement Description:Interior Access, Outside Entrance
- Living area:2,102 sq. ft.
Heating and cooling
- Cooling:Ceiling Fan(s), Heat Pump(s)
- Heating:Electric, Heat Pump(s)
Structure and exterior
- Roof:Asphalt
- Year built:1900
- Building area:2,102 sq. ft.
- Lot area:0.37 Acres
- Architectural Style:Colonial
- Construction Materials:Frame, Stone
- Exterior Features:Patio(s)
- Foundation Description:Permanent
- Levels:3 Story
Schools
- High school:JOHN HANDLEY
- Middle school:DANIEL MORGAN
- Elementary school:JOHN KERR
Utilities
- Water:Public
- Sewer:Public Sewer
Finances and disclosures
- Price:$349,990
- Price per sq. ft.:$166.5
- Tax amount:$2,758 (2025)
Features and amenities
- Laundry features:Washer/Dryer Hookups Only
- Amenities:Built-Ins, Crown Moldings, Double/Dual Staircase
Parking
- Parking description:Gravel Driveway, Off Street
New listings near 519 Fairmont Ave
- Coming Soon
$400,000Coming Soon2 beds 2 baths1853 Rosser Ln, WINCHESTER, VA 22601
MLS# VAWI2011294Listed by: REALTY FC - New
$295,000Active2 beds 2 baths1,200 sq. ft.207 Banbury Ter, WINCHESTER, VA 22601
MLS# VAFV2043868Listed by: ROBERTS REALTY GROUP, LLC - Coming Soon
$650,000Coming Soon4 beds 4 baths1529 Dalton Pl, WINCHESTER, VA 22601
MLS# VAWI2011266Listed by: RE/MAX ROOTS - New
$375,000Active3 beds 2 baths1,678 sq. ft.1004 Pennsylvania Ave, WINCHESTER, VA 22601
MLS# VAWI2011076Listed by: SAMSON PROPERTIES - New
$180,000Active3 beds 1 baths1,054 sq. ft.309 Liberty Ave, WINCHESTER, VA 22601
MLS# VAWI2011268Listed by: KELLER WILLIAMS REALTY - New
$719,000Active7 beds 5 baths4,736 sq. ft.2700 Loyalty Ct, WINCHESTER, VA 22601
MLS# VAWI2011262Listed by: ELCY & CO. REALTY, LLC. 
$359,900Pending3 beds 1 baths1,075 sq. ft.236 Shawnee Ave, WINCHESTER, VA 22601
MLS# VAWI2011258Listed by: RE/MAX ROOTS
$359,990Pending3 beds 4 baths1,756 sq. ft.233 Monteith Dr #homesite 12, WINCHESTER, VA 22601
MLS# VAWI2010858Listed by: DRB GROUP REALTY, LLC- Open Sat, 11am to 1pm
$429,000Active4 beds 2 baths1,844 sq. ft.1310 Whittier Ave, WINCHESTER, VA 22601
MLS# VAWI2011230Listed by: REALTY ONE GROUP OLD TOWNE 
$364,000Active3 beds 4 baths2,592 sq. ft.2055 Cidermill Ln, WINCHESTER, VA 22601
MLS# VAWI2011084Listed by: COLONY REALTY
Protect your home and budget from life's surprises with an Assurant Home Warranty, backed by a partner that supports you through every step of homeownership. Explore Plans.
© 2026 Better Homes and Gardens Real Estate LLC. An Anywhere Real Estate company. All rights reserved. Better Homes and Gardens® Real Estate is a registered trademark owned by Meredith Operations Corporation, licensed to Better Homes and Gardens Real Estate LLC and used with permission. Better Homes and Gardens Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Listing information is deemed reliable but is not guaranteed accurate.
Each office is independently owned and operated.
Any services or products provided by third parties are not provided by, affiliated with or related to Better Homes and Gardens Real Estate LLC, or its affiliated companies.