Rare Historical Winchester Investment Opportunity – Three Properties in One Location An outstanding investment opportunity awaits in the heart of Winchester City. This unique portfolio comprises three properties positioned along the same street, offering exceptional potential for developers, investors, or those seeking a landmark project for multi-unit rentals or commercial development. Both existing multi-unit buildings have a total of 5 units. The properties benefit from an approved site plan and historical planning approval, providing a valuable foundation for future development, subject to the necessary consents and any relevant conditions. With the convenience of city-center living on the doorstep, the site is ideally placed close to Winchester’s historic attractions, independent shops, restaurants, cafés, transport links, and highly regarded schools. Opportunities of this scale and location are rarely available. Whether considered as a strategic investment, a redevelopment project, or a long-term development opportunity, this is a compelling chance to secure three properties together in the historic heart of Winchester. Key features: • Three properties located on one street • Prime central Winchester location • Approved site plan • Historical planning approval • Strong investment and development potential • Close to shops, restaurants, schools, transport links, and historic landmarks • Rare opportunity to acquire the properties as one portfolio 3 Physical property addresses are 224 Sharp Street, 225 E. Boscowan Street, and 11 S East Lane Interested parties should make their own inquiries with Winchester City Council and obtain independent legal, planning, and financial advice before proceeding.
Historic District, located between Old Town Winchester and Handley Regional Library, is a historic and walkable Winchester neighborhood with brick sidewalks and Victorian-era streetscapes. The neighborhood’s character concentrates along the Loudoun Street Mall at N Loudoun St and W Boscawen St, where independent cafes, galleries, and small shops set a steady, street-level rhythm. Community pillars include the Bright Box Theater, the Museum of the Shenandoah Valley, and Winchester Little Theatre. Architecture leans toward restored rowhouses, porch-front homes, and converted commercial buildings with period details. Pocket parks and courthouse greens shape daily routines, while seasonal festivals bring extra foot traffic to the pedestrian blocks. Trails and gardens near the museum add a quieter counterpoint to the downtown grid.
Provided by Walk Score and Local Logic
Market insights
224 Sharp St · $750,000
DAYS ON MARKET
69 days
The average home goes pending in 8 days.
SALE-TO-LIST
95.5%
Most homes are selling 5% below list price.
LIST PRICE
$750,000
Median list price in this area is $529,000. (29% lower than this home)
Property details
Interior
Exterior
Finance
Interior features
Plaster walls
Unfinished basement
Has fireplace (1)
Bedrooms
19 single-room units
5 two-bedroom units
5 units currently leased
Flooring
Hardwood floors
Exterior features
Above-grade structures present
Home design
Detached structure
Parking
Off-street parking
Construction
Brick and combination exterior with copper plumbing
Block and stone foundation
Metal roof
Building winterized
Estimated year built
Utilities
120/240V electric service
Electric hot water
Public water
Public septic
Financial info
Ownership: Fee simple
Property condition: Major rehab needed
No existing leases
No rent control
Other
Above-grade finished area estimated at 3,484
Electricity and solar
View estimated energy costs and solar savings for this home
This district is intended for the conduct of business to which the public requires direct and frequent access, but which is not characterized either by constant heavy trucking other than stocking and delivery of light retail goods, or by any other nuisance factors other than occasioned by incidental light and noise of congregation of people and passenger vehicles. This includes such uses as retail stores, banks, theaters, business offices, newspaper offices, and restaurants.
Permitted uses
Include but are not limited to:
Religious facility
Bank
Day care facility
Housing-Single unit
Housing-Multiple units
Bed & breakfast
Office
Fire house
Post office
Kennel
Nov 19, 2023 • Final
B - asbestos abatement
Perform asbestos abatement.
Demolition
Mar 23, 2014 • Final
P - plumbing
Replace the water service line.
Plumbing
Permit history is from public records and may be incomplete or inaccurate. Redfin and its agents make no representations about the property condition or permit status. Buyers should independently verify all information.
Climate risks
1/10 Flood Factor
Minimal risk of a flood reaching the building in the next 30 years
1/10 Fire Factor
Unlikely to be in a wildfire in next 30 years
5/10 Heat Factor
7 days above 102° expected this year, 16 days in 30 years
2/10 Wind Factor
1% chance of strong winds in next 30 years
2/10 Air Factor
0 unhealthy days expected this year, 1 days in 30 years
Provided by First Street
Historical weather
Winchester, VA • 22601
Average low and high temperatures (°F)
37
22
45
27
62
38
69
47
72
53
83
64
88
69
79
60
78
57
67
44
57
38
43
27
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
98/ 100
Exceptional sunlight
Sunscore
This home ranks in the top 13% for direct sun exposure in Winchester. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.
10.1 hrs
6.4 hrs
JuneDecember
Provided by Shadowmap
Redfin Estimate for 224 Sharp St
$719,438
$31K under list price of $750K
Nearby comparable homes
The Redfin Estimate uses 6 recent nearby sales, priced between $350K to $540K.