Welcome to 540 Monticello Street, a turnkey Multi-Unit Investment Opportunity in Prime Downtown Winchester Location! Presenting a Triplex in the heart of Downtown Winchester—a rare opportunity for investors seeking strong cash flow in a highly desirable and commuter-friendly location. Just minutes from I-81 and I-66, and less than an hour from Northern Virginia, this property offers convenience, charm, and long-term value. The building features two 2-Bedroom, 1-Bath Units – Each offers large Kitchens, updated finishes, and their own Laundry Rooms. One of the units is ground level, and the other 2nd-Level unit has access to its own deck space. The largest unit of the three features two finished levels, connected with an interior staircase, 5-Bedrooms, 2 Full Baths, 2 Living Rooms, a Full kitchen, Laundry, and access to it's own private patio & deck. It's a unique two-level layout, perfect for multi-tenants and/or premium rental rates. Recent renovations throughout the last few years include: Luxury vinyl plank (LVP) flooring, fresh paint, and updated kitchens and baths Newer appliances in each unit The roof less than 3 years old New HVAC installed (2025) Designated parking for all units With all units currently leased, this is a true turnkey investment with reliable income and minimal immediate maintenance needs. This well-maintained building features three fully occupied units, bringing in a current gross annual rental income of $45,300. Whether you're looking to grow your portfolio or occupy a unit while renting the others, or the potential for a short-term rental, this property checks all the boxes!
Rare Opportunity: Turnkey Duplex in Winchester – Vacant, Updated, and Ready for Your Next Move! A rare and an exceptional opportunity to own a two-unit duplex in Winchester City— vacant and ready for your plans. Whether you’re an investor seeking strong cash flow or an owner-occupant looking to live in one unit and rent the other, this property offers flexibility, income potential, and low maintenance. Located at 26-A Jackson Avenue, Units A & B, Winchester, VA 22601, this well-maintained duplex features two spacious units, each offering 2 bedrooms, 1.5 bathrooms, laundry rooms with washer and dryer hookups, private fenced backyards, and off-street dedicated parking. Built with comfort and practicality in mind, both units have been updated and are move-in ready, creating an excellent opportunity to begin generating income immediately or design your own living and rental arrangement. The home sits in a residential area of Winchester, convenient to downtown, shopping, restaurants, and major commuter routes. With projected rents of approximately $1,600 per month per unit, the income potential is strong, while the vacant status allows for quick occupancy or tenant placement. Properties like this are rare in Winchester. Offering updated interiors, private outdoor space, and strong rental demand, this duplex presents the perfect blend of stability and opportunity. Whether you’re building your portfolio or looking for a practical owner-occupied investment, this property checks every box. Schedule your private showing today and explore the possibilities this Winchester duplex has to offer.
Income-Producing Duplex in Prime Winchester Location – Unique Investment Opportunity! Just two blocks south of Old Town Winchester’s Walking Mall, this charming duplex sits on a quiet residential street—offering the best of both location and lifestyle. With a strong rental history and over $54,000 in rental income in 2024, this property delivers a solid 6% cap rate, making it an ideal opportunity for both investors and owner-occupants. It is rented short term (13 – 26 weeks) to traveling medical professionals. Both units come fully furnished. The property features two well-maintained units: Unit 1: 2 Bedrooms 2 Bathrooms Direct Walkout Basement. Unit 2: 2 Bedrooms 1 Bathroom. Both units include: Spacious living rooms, formal dining areas, and full kitchens. Finished third-floor bonus spaces—perfect for offices, guest rooms, or play areas. Beautiful hardwood floors throughout. Front and side porches offering private outdoor spaces. Full, private, unfinished basements with laundry—ample storage or future finishing potential. With four years of verifiable rental income, this turnkey property offers flexibility: live in one unit and rent the other or continue renting both for maximum returns. The 2-bed/2-bath unit’s walkout basement provides added value and accessibility. Don’t miss your chance to own a rare, income-producing property in the heart of Winchester—location, charm, and cash flow all in one.
Versatile on Valley! So many possibilities! This versatile duplex is full of charm and opportunity! The original 1936 home features beautiful wood floors, tall ceilings, fireplace, sunroom, and a stunning staircase that adds timeless character. The front unit is perfect for an owner-occupant who wants to enjoy historic charm while generating income from the back unit, or you can rent out both units for a strong investment. The rear unit is already leased to a reliable tenant, providing immediate cash flow. The new roof and gutters were installed just last year and both full bathrooms have been updated to include walk-in tiled showers. The heating fuel was converted to natural gas and new boilers were installed in 2011. Each unit has separate utilities except for water and sewer. With its unique character, flexible layout, and proven rental history, this property offers endless possibilities for living, investing, or both!
All brick 3 unit complex with off street parking and near Old Town Mall..2nd floor has 2BD/1BA with unfinished attic, main floor is 1BR/1BA (Both have rear balcony) and basement unit has access to storage area and includes1BD/1BA. All units have washer/dryer (Basement unit washer/dryer belongs to tenant). Owner/Agent and home inspection report available upon request.
*** ATTENTION INVESTORS - OFFERED AT A NEW PRICE!! *** You will want to check out this fantastic opportunity - with a history of POSITIVE CASH FLOW these two ADJACENT PROPERTIES on a combined total of 1.91-acres in Winchester (just minutes from Valley Health Campus, shopping, restaurants and Rt. 37) may be what you are looking for! These two parcels are to be sold TOGETHER; they are not offered separately, and all for an updated package deal at $475,000! *** 386 Round Hill Road sits on 1.51 acres and consists of 3 UNITS - 2 units are on the main level and one unit is on upper level... each unit has 2 BR, 1 BA, a Living area, Kitchen and laundry hook-up area, and this building totals approximately 2736 SF). Unit 2 is a bit bigger with some additional bonus rooms. 402 Round Hill Road is approximately 1008 SF and features 2 BR, 1 BA, Living Room, formal Dining Room, Kitchen and laundry area (with hook-up only); this property sits on 0.40-acre and includes a covered back porch and the detached garage. Tenants pay utilities. Each unit is separately metered. Each parcel has its own well and septic system. Current tenants would love to stay. ALL units are currently rented! Contact listing agent for information on individual lease terms and rental rates.
Welcome to 540 Monticello Street, a turnkey Multi-Unit Investment Opportunity in Prime Downtown Winchester Location! Presenting a Triplex in the heart of Downtown Winchester—a rare opportunity for investors seeking strong cash flow in a highly desirable and commuter-friendly location. Just minutes from I-81 and I-66, and less than an hour from Northern Virginia, this property offers convenience, charm, and long-term value. The building features two 2-Bedroom, 1-Bath Units – Each offers large Kitchens, updated finishes, and their own Laundry Rooms. One of the units is ground level, and the other 2nd-Level unit has access to its own deck space. The largest unit of the three features two finished levels, connected with an interior staircase, 5-Bedrooms, 2 Full Baths, 2 Living Rooms, a Full kitchen, Laundry, and access to it's own private patio & deck. It's a unique two-level layout, perfect for multi-tenants and/or premium rental rates. Recent renovations throughout the last few years include: Luxury vinyl plank (LVP) flooring, fresh paint, and updated kitchens and baths Newer appliances in each unit A roof less than 3 years old Designated parking for all units With all units currently leased, this is a true turnkey investment with reliable income and minimal immediate maintenance needs. This well-maintained building features three fully occupied units, bringing in a current gross annual rental income of $43,200. Whether you're looking to grow your portfolio or occupy a unit while renting the others, or the potential for a short-term rental, this property checks all the boxes!
In town location for this completely remodeled multi unit property. This property contains 4 homes and 2 apartments that have been completely refinished. The main home is currently lived in by the owner and is attached to a indoor swimming pool. The other 3 homes and 2 apartments are leased and are bringing over$10,500 monthly. If you choose rent the main house income would be much higher. . Update, main house is now rented and income is $15,000 per month. This property is also improved with large block garage and a separate 4 car garage with over 18' ceilings. Perfect for the automotive enthusiast or you can continue to rent.
Back on the market due to NO fault of the Seller! Currently a single family home with a private “guest apartment”, but zoned multi-family with the potential for up to 4 units and potentially $4000.00+ in monthly rental income! Fantastic opportunity! The private guest suite currently has 2 bedrooms. The 3rd floor also has an additional 2 bedrooms, full bathroom and could laundry room that could be a potential rental space. Fantastic opportunity! This home is one block from the beautiful, outdoor Old Town mall, and located on the coveted Apple Blossom parade route! Be in the center of the most exciting Bloom parties, with front and center seats to view the parade and host all of your friends and family. Nestled in the center of Winchester’s Historic District, this stately home offers the perfect balance of circa 1890 J.B Russel stunning architecture and new modern finishes. Surrounded by beautiful woodwork, brick-exposed walls, arched walls and doorways and soaring 12-foot ceilings, this home exudes elegance. The renovations done in the last 2 years have stayed true to the home's original architecture, while modernizing it and adding luxurious features throughout. The kitchen renovation was just completed, and consisted of enlarging the original space to include beautiful two-tone cabinetry, marble countertops, high-end appliances and an expansive center island with additional seating. Large families or out of town guests will sleep comfortably in one of the 7 bedrooms. One of the bedrooms is conveniently located on the main level, featuring a fireplace, wet bar and renovated attached bathroom. The remaining bedrooms are on the top two floors, with more charming fireplaces and additional features such as adjoining sitting rooms and a sunroom. The opulent primary bedroom is a light and bright room, featuring a fireplace and walk-in closet with custom built-in cabinetry. Total relaxation awaits you in the luxurious primary bathroom, with dual sinks, heated floors, a large walk-in shower and copper tub. This serene room also gives access to a private balcony, overlooking the beautifully landscaped grounds. This home is an entertainer's dream, with plenty of formal spaces throughout for gathering friends and family. Additionally, the 2200+ square foot finished basement offers a unique space that could have multiple uses. The brick floors and walls, beamed ceilings and overall dark ambiance give this space a vintage Speak Easy look. A recipient of the 2023 Winchester Lucille Lozier Award, all of the renovations were completed in accordance with the Winchester Historic Architecture Board.
For Sale – 1.89 + Acres Redevelopment Site located just off Valley Avenue in southern Winchester. Property consists of 2 parcels and includes a single family detached rental and one unimproved lot. Lot is zoned MR and Improved parcel is zoned B-2. Property is ideally suited for multi-family development. All properties are leased. Call listing broker for additional information. Do not disturb tenants. Showings of house and duplex by appointment only and only after a ratified contract.
Winchester is located in Virginia. Winchester, Virginia has a population of 28,194. Winchester is less family-centric than the surrounding county with 26.15% of the households containing married families with children. The county average for households married with children is 26.15%.
The median household income in Winchester, Virginia is $61,321. The median household income for the surrounding county is $61,321 compared to the national median of $69,021. The median age of people living in Winchester is 36.6 years.
The average high temperature in July is 85.7 degrees, with an average low temperature in January of 21.3 degrees. The average rainfall is approximately 38.3 inches per year, with 21.9 inches of snow per year.
