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Discover the perfectly updated turnkey home you’ve been searching for in Historic Winchester. This beautifully maintained property offers 3 bedrooms and 2.5 bathrooms, including a spacious primary suite with a full bath and walk‑in closet, convenient main‑level laundry, and a flat, usable backyard with alley access—ideal for a future garage or additional off‑street parking. Gardeners will love the lush lawn, raised beds, mature plantings, and thoughtfully designed greenhouse. Enjoy morning coffee or evening conversations on the welcoming full front porch or the private back deck. Extensive upgrades over the past decade provide both comfort and peace of mind, all within an unbeatable location close to the downtown pedestrian mall, Jim Barnett Park, the Green Circle Trail, and everything Winchester has to offer. Major Improvements Include: • 2016: New electric, dual‑zone HVAC, plumbing, hot water heater, wall & roof insulation, stainless steel appliances, upgraded kitchen & baths, new deck • 2017: New main‑level washer & dryer • 2019: New 30‑year SmartSide siding and double‑hung windows • Additional recent updates: reglazed decorative “9‑light” window, new greenhouse & raised beds, and freshly repainted front and side porches

3 Beds ⋅ 3 Baths

Discover the perfectly updated turnkey home you’ve been searching for in Historic Winchester. This beautifully maintained property offers 3 bedrooms and 2.5 bathrooms, including a spacious primary suite with a full bath and walk‑in closet, convenient main‑level laundry, and a flat, usable backyard with alley access—ideal for a future garage or additional off‑street parking. Gardeners will love the lush lawn, raised beds, mature plantings, and thoughtfully designed greenhouse. Enjoy morning coffee or evening conversations on the welcoming full front porch or the private back deck. Extensive upgrades over the past decade provide both comfort and peace of mind, all within an unbeatable location close to the downtown pedestrian mall, Jim Barnett Park, the Green Circle Trail, and everything Winchester has to offer. Major Improvements Include: • 2016: New electric, dual‑zone HVAC, plumbing, hot water heater, wall & roof insulation, stainless steel appliances, upgraded kitchen & baths, new deck • 2017: New main‑level washer & dryer • 2019: New 30‑year SmartSide siding and double‑hung windows • Additional recent updates: reglazed decorative “9‑light” window, new greenhouse & raised beds, and freshly repainted front and side porches

244 Parkway St, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact:

Selling Office: Samson Properties.

$429,000

Opportunity is knocking! This 3-unit multifamily property is centrally located in downtown Winchester, just minutes from the Walking Mall. The property is fully occupied and offers immediate rental income with strong upside potential. The property currently has a long term tenants with leases as follows: One month-to-month tenant , One tenant with a lease ending June 5, 2026 , One tenant with a lease ending March 14, 2027. All three units offer the potential for rent increases, providing an excellent value-add opportunity for investors. Conveniently located near shopping, dining, entertainment, and downtown amenities, this property is well-positioned for long-term growth and cash flow.

406-408 S Cameron St, Winchester

Listing courtesy of Samson Properties. Contact:

Selling Office: Pearson Smith Realty LLC.

$425,000

Welcome to 743 Berryville Ave in the heart of Downtown Winchester! This unique and versatile property offers exceptional space and flexibility with two fully equipped living areas on one lot. The main house features 4 bedrooms, 2 full bathrooms, 2 kitchens, and 2 laundry areas—ideal for multi-generational living or added convenience. Enjoy a spacious layout with plenty of room for everyone to spread out comfortably. The highlight of this property is the additional detached unit in the rear, complete with 2 bedrooms, 1 full bathroom, its own kitchen, and laundry—perfect for extended family, guests. A huge parking lot behind the home provides ample off-street parking, a rare find in Downtown Winchester. Buy one property and enjoy the benefit of two fully functional homes on one lot—perfect for a large family who values privacy while staying close together, all in a prime location near shops, dining, and historic Old Town Winchester.

4 Beds ⋅ 2 Baths

Welcome to 743 Berryville Ave in the heart of Downtown Winchester! This unique and versatile property offers exceptional space and flexibility with two fully equipped living areas on one lot. The main house features 4 bedrooms, 2 full bathrooms, 2 kitchens, and 2 laundry areas—ideal for multi-generational living or added convenience. Enjoy a spacious layout with plenty of room for everyone to spread out comfortably. The highlight of this property is the additional detached unit in the rear, complete with 2 bedrooms, 1 full bathroom, its own kitchen, and laundry—perfect for extended family, guests. A huge parking lot behind the home provides ample off-street parking, a rare find in Downtown Winchester. Buy one property and enjoy the benefit of two fully functional homes on one lot—perfect for a large family who values privacy while staying close together, all in a prime location near shops, dining, and historic Old Town Winchester.

743 Berryville Ave, Winchester

Listing courtesy of Pearson Smith Realty, LLC. Contact:

Selling Office: The Vasquez Group LLC.

$374,900

Welcome to 317 Gray Ave in Winchester, Virginia. This charming Colonial blends historic character with extensive modern updates, creating the perfect balance of vintage appeal and contemporary comfort. The home features 4 bedrooms, 2 full bathrooms, and 1 half bathroom, along with a recently finished attic that offers flexible additional living space. The primary suite includes a beautifully renovated private bathroom, while another bedroom features direct attic access, ideal for a home office, creative space, or extra storage. One of the bedrooms also offers balcony access overlooking the spacious backyard, adding unique charm to the home. While the property maintains its original hardwood floors and classic character, it has undergone significant improvements, including: • Fully renovated kitchen with quartz countertops, new cabinetry, stainless steel appliances, and backsplash • Upgraded bathrooms, including a new half bath and renovated primary bathroom • Fresh paint throughout • New roof 2025 • Two HVAC systems, One Brand New 2026 and the second HVAC (2023) with zoned heating and cooling. The exterior offers a large fenced backyard with new wire fencing, providing privacy, functionality, and additional convenience. 0.17-acre lot (7,423 sq ft) Long 190-ft deep lot with ALLEY ACCESS. Located just minutes from downtown Winchester, this home offers easy access to shopping, dining, parks, and commuter routes. This property is truly move-in ready and presents a rare opportunity to own a historic home thoughtfully updated with today’s essential upgrades.

4 Beds ⋅ 3 Baths

Welcome to 317 Gray Ave in Winchester, Virginia. This charming Colonial blends historic character with extensive modern updates, creating the perfect balance of vintage appeal and contemporary comfort. The home features 4 bedrooms, 2 full bathrooms, and 1 half bathroom, along with a recently finished attic that offers flexible additional living space. The primary suite includes a beautifully renovated private bathroom, while another bedroom features direct attic access, ideal for a home office, creative space, or extra storage. One of the bedrooms also offers balcony access overlooking the spacious backyard, adding unique charm to the home. While the property maintains its original hardwood floors and classic character, it has undergone significant improvements, including: • Fully renovated kitchen with quartz countertops, new cabinetry, stainless steel appliances, and backsplash • Upgraded bathrooms, including a new half bath and renovated primary bathroom • Fresh paint throughout • New roof 2025 • Two HVAC systems, One Brand New 2026 and the second HVAC (2023) with zoned heating and cooling. The exterior offers a large fenced backyard with new wire fencing, providing privacy, functionality, and additional convenience. 0.17-acre lot (7,423 sq ft) Long 190-ft deep lot with ALLEY ACCESS. Located just minutes from downtown Winchester, this home offers easy access to shopping, dining, parks, and commuter routes. This property is truly move-in ready and presents a rare opportunity to own a historic home thoughtfully updated with today’s essential upgrades.

317 Gray Ave, Winchester

Listing courtesy of Keller Williams Realty. Contact:

Selling Office: EXP Realty, LLC.

$335,000

Welcome to this home where classic charm meets modern versatility! Built in 1948, this property offers warmth, character, and flexible living spaces designed to fit today’s lifestyle. Step inside to a spacious main level featuring a bright and inviting family room, a dedicated dining area, and an eat-in kitchen—perfect for everyday living and entertaining. This home offers 3–4 bedroom options, giving you the flexibility to create a home office, playroom, guest space, or additional bedroom to suit your needs. Needs improved and just envision the unlimited possibilities. Updated HVAC and Hot water Heater recently. Ready to move in. Enjoy the convenience of two full bathrooms, including one privately located off the primary bedroom, while the second is ideally situated off the hallway near the additional bedroom. Upstairs, the full walk-up attic provides an incredible opportunity—easily transform this expansive space into a private third bedroom suite with room for a sitting area, studio, or retreat. ✨ Highlights You’ll Love: Flexible 3–4 bedroom layout Full walk-up attic with expansion potential Primary bedroom with private bath Eat-in kitchen + formal dining space Charming character throughout This home blends timeless charm with endless possibilities, making it perfect for buyers looking to personalize and grow into their space. This home is virtually staged to help you visually see how your furniture can fit in the space.

3 Beds ⋅ 2 Baths

Welcome to this home where classic charm meets modern versatility! Built in 1948, this property offers warmth, character, and flexible living spaces designed to fit today’s lifestyle. Step inside to a spacious main level featuring a bright and inviting family room, a dedicated dining area, and an eat-in kitchen—perfect for everyday living and entertaining. This home offers 3–4 bedroom options, giving you the flexibility to create a home office, playroom, guest space, or additional bedroom to suit your needs. Needs improved and just envision the unlimited possibilities. Updated HVAC and Hot water Heater recently. Ready to move in. Enjoy the convenience of two full bathrooms, including one privately located off the primary bedroom, while the second is ideally situated off the hallway near the additional bedroom. Upstairs, the full walk-up attic provides an incredible opportunity—easily transform this expansive space into a private third bedroom suite with room for a sitting area, studio, or retreat. ✨ Highlights You’ll Love: Flexible 3–4 bedroom layout Full walk-up attic with expansion potential Primary bedroom with private bath Eat-in kitchen + formal dining space Charming character throughout This home blends timeless charm with endless possibilities, making it perfect for buyers looking to personalize and grow into their space. This home is virtually staged to help you visually see how your furniture can fit in the space.

514 Cather Ave, Winchester

Listing courtesy of EXP Realty, LLC. Contact:

Selling Office: Pearson Smith Realty, LLC.

$330,000

Welcome to this charming home in the heart of Winchester offering character, natural light, and a highly walkable location. This home features 3 bedrooms and 2 full bathrooms, with all bedrooms located on the upper level. At the top of the stairs you’ll find a spacious primary bedroom filled with natural light, creating a bright and inviting retreat. Large windows throughout the home allow sunlight to fill the living spaces, giving the home an airy feel. It also has alley access allowing for off-street parking. The living room offers generous space for relaxing or entertaining, while the kitchen provides a functional layout for everyday cooking. A finished attic space with high ceilings and windows on three sides adds additional flexibility for a home office, hobby space, or reading area. This home has charm of construction with tall ceilings and pocket doors. The walk-out unfinished basement with backyard access provides excellent storage. Outside, the backyard receives great sun exposure and includes a new storage shed for additional convenience. Recent updates include a brand-new roof; March 2026. This includes brand new shingles and metal roofing. Located in a quiet, tree-lined neighborhood with wide sidewalks, this home is just two blocks from Handley Regional Library and within walking distance to shops, dining, and entertainment at the Old Town Winchester Walking Mall. Nearby dining includes Pizzoco Pizza Parlor just around the corner. Enjoy a convenient in-town location close to parks, local amenities, and downtown attractions while still tucked within a peaceful residential setting. Home was once two apartments thus third bedroom is open and owner liked it like that. It was a form living area for upper apt. Home sold as-is.

3 Beds ⋅ 2 Baths

Welcome to this charming home in the heart of Winchester offering character, natural light, and a highly walkable location. This home features 3 bedrooms and 2 full bathrooms, with all bedrooms located on the upper level. At the top of the stairs you’ll find a spacious primary bedroom filled with natural light, creating a bright and inviting retreat. Large windows throughout the home allow sunlight to fill the living spaces, giving the home an airy feel. It also has alley access allowing for off-street parking. The living room offers generous space for relaxing or entertaining, while the kitchen provides a functional layout for everyday cooking. A finished attic space with high ceilings and windows on three sides adds additional flexibility for a home office, hobby space, or reading area. This home has charm of construction with tall ceilings and pocket doors. The walk-out unfinished basement with backyard access provides excellent storage. Outside, the backyard receives great sun exposure and includes a new storage shed for additional convenience. Recent updates include a brand-new roof; March 2026. This includes brand new shingles and metal roofing. Located in a quiet, tree-lined neighborhood with wide sidewalks, this home is just two blocks from Handley Regional Library and within walking distance to shops, dining, and entertainment at the Old Town Winchester Walking Mall. Nearby dining includes Pizzoco Pizza Parlor just around the corner. Enjoy a convenient in-town location close to parks, local amenities, and downtown attractions while still tucked within a peaceful residential setting. Home was once two apartments thus third bedroom is open and owner liked it like that. It was a form living area for upper apt. Home sold as-is.

520 N Braddock St, Winchester

Listing courtesy of MarketPlace REALTY. Contact:

Selling Office: Realty ONE Group Old Towne.

$326,000

Beautifully charming and completely move-in ready, this updated 4-bedroom, 2-bath home offers the perfect blend of style, comfort, and functionality. Step inside to find updated flooring and an open-concept main living area designed for today's lifestyle. The heart of the home is the stunning kitchen, featuring granite countertops, white cabinetry, updated fixtures, and a spacious center island with barstool seating—perfect for casual dining, entertaining, or gathering with family and friends. All four bedrooms are generously sized with ample closet space, while both bathrooms have been tastefully updated with modern finishes. Outside, enjoy a large backyard with plenty of room to relax, play, or entertain. The one-car garage is complemented by an oversized driveway that easily accommodates 3–4 additional vehicles, providing exceptional convenience for guests and everyday living. Stylish updates, spacious living areas, and a move-in-ready condition make this home one you won't want to miss.

4 Beds ⋅ 2 Baths

Beautifully charming and completely move-in ready, this updated 4-bedroom, 2-bath home offers the perfect blend of style, comfort, and functionality. Step inside to find updated flooring and an open-concept main living area designed for today's lifestyle. The heart of the home is the stunning kitchen, featuring granite countertops, white cabinetry, updated fixtures, and a spacious center island with barstool seating—perfect for casual dining, entertaining, or gathering with family and friends. All four bedrooms are generously sized with ample closet space, while both bathrooms have been tastefully updated with modern finishes. Outside, enjoy a large backyard with plenty of room to relax, play, or entertain. The one-car garage is complemented by an oversized driveway that easily accommodates 3–4 additional vehicles, providing exceptional convenience for guests and everyday living. Stylish updates, spacious living areas, and a move-in-ready condition make this home one you won't want to miss.

629 National Ave, Winchester

Listing courtesy of Samson Properties. Contact:

Selling Office: Samson Properties.

$285,000

Charming home ideally located just minutes from the heart of historic Winchester! Whether you're looking for convenient access to shopping, dining, entertainment, or commuter routes, this home offers an exceptional location paired with valuable updates for peace of mind. Relax on the inviting covered front porch, the perfect place to enjoy your morning coffee or unwind at the end of the day. The property also features an amazing yard with plenty of space for gardening, entertaining, pets, or simply enjoying the outdoors. Inside, you'll find comfortable living spaces, 2 bedrooms, a partially finished basement, and a walk-up attic providing excellent storage and flexibility. Recent major improvements help make homeownership worry-free, including a new roof (2025), new AC condenser (2022), and new water heater (2021). Enjoy being close to Winchester's vibrant downtown pedestrian mall, local restaurants, coffee shops, parks, museums, and year-round community events that make the city such a desirable place to call home. Commuters will appreciate the easy access to Routes 50, 7, 522, and I-81, providing convenient travel throughout the Shenandoah Valley and beyond. A wonderful opportunity to own a well-maintained home with character, outdoor space, and an unbeatable location.

2 Beds ⋅ 1 Baths

Charming home ideally located just minutes from the heart of historic Winchester! Whether you're looking for convenient access to shopping, dining, entertainment, or commuter routes, this home offers an exceptional location paired with valuable updates for peace of mind. Relax on the inviting covered front porch, the perfect place to enjoy your morning coffee or unwind at the end of the day. The property also features an amazing yard with plenty of space for gardening, entertaining, pets, or simply enjoying the outdoors. Inside, you'll find comfortable living spaces, 2 bedrooms, a partially finished basement, and a walk-up attic providing excellent storage and flexibility. Recent major improvements help make homeownership worry-free, including a new roof (2025), new AC condenser (2022), and new water heater (2021). Enjoy being close to Winchester's vibrant downtown pedestrian mall, local restaurants, coffee shops, parks, museums, and year-round community events that make the city such a desirable place to call home. Commuters will appreciate the easy access to Routes 50, 7, 522, and I-81, providing convenient travel throughout the Shenandoah Valley and beyond. A wonderful opportunity to own a well-maintained home with character, outdoor space, and an unbeatable location.

102 N Purcell Ave, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact:

Selling Office: Unrepresented.

$280,000

Beautifully Maintained Bungalow in a Prime Location! SELLER MOTIVATED! This home offers 2 bedrooms and 1 full bath on the main level, showcasing pride of ownership throughout. Ideally located just blocks from shopping, coffee shops, and all the conveniences the city has to offer, this property combines comfort with unbeatable accessibility. Enjoy a spacious eat-in kitchen with plenty of room for a dining table—perfect for everyday living and entertaining. A convenient side entrance makes hosting family barbecues easy and enjoyable. The living room features durable vinyl plank flooring, adding both style and functionality. The home has been thoughtfully updated with modern interior and exterior lighting, along with updated appliances, ensuring a move-in ready experience. The basement significantly expands the living space, offering two additional rooms and a full bathroom, providing incredible flexibility for guests, a home office, recreation space, or extended living. There is also ample room for storage. Situated on a quiet end street, this home is ideal for first-time buyers, those looking to downsize, or anyone seeking the convenience of main-level living with bonus space below. Don’t miss this opportunity to own a versatile and well-cared-for home in a fantastic location!

2 Beds ⋅ 2 Baths

Beautifully Maintained Bungalow in a Prime Location! SELLER MOTIVATED! This home offers 2 bedrooms and 1 full bath on the main level, showcasing pride of ownership throughout. Ideally located just blocks from shopping, coffee shops, and all the conveniences the city has to offer, this property combines comfort with unbeatable accessibility. Enjoy a spacious eat-in kitchen with plenty of room for a dining table—perfect for everyday living and entertaining. A convenient side entrance makes hosting family barbecues easy and enjoyable. The living room features durable vinyl plank flooring, adding both style and functionality. The home has been thoughtfully updated with modern interior and exterior lighting, along with updated appliances, ensuring a move-in ready experience. The basement significantly expands the living space, offering two additional rooms and a full bathroom, providing incredible flexibility for guests, a home office, recreation space, or extended living. There is also ample room for storage. Situated on a quiet end street, this home is ideal for first-time buyers, those looking to downsize, or anyone seeking the convenience of main-level living with bonus space below. Don’t miss this opportunity to own a versatile and well-cared-for home in a fantastic location!

704 Watson Ave, Winchester

Listing courtesy of Samson Properties. Contact:

Selling Office: Smart Realty, LLC.

$219,000

This two-story home offers classic charm with a covered front porch, fenced backyard, and upper-level balcony. Located just minutes from downtown, 369 Charles Street features a recently updated kitchen with modern cabinetry, granite countertops, and stainless steel appliances. The main level features updated flooring, while the upstairs level provides access to a private, covered balcony. Two full bathrooms have been recently renovated with a tiled walk-in shower and new fixtures. Alley access and a spacious backyard offer potential for off-street parking or additional improvements. Sold as-is. Ideal for investors. The property was built before 1978, and Lead-Based Paint May Be Present.

3 Beds ⋅ 2 Baths

This two-story home offers classic charm with a covered front porch, fenced backyard, and upper-level balcony. Located just minutes from downtown, 369 Charles Street features a recently updated kitchen with modern cabinetry, granite countertops, and stainless steel appliances. The main level features updated flooring, while the upstairs level provides access to a private, covered balcony. Two full bathrooms have been recently renovated with a tiled walk-in shower and new fixtures. Alley access and a spacious backyard offer potential for off-street parking or additional improvements. Sold as-is. Ideal for investors. The property was built before 1978, and Lead-Based Paint May Be Present.

369 Charles St, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact:

Selling Office: EXP Realty, LLC.

$180,000

Office / Retail space in the Opequon Center on Valley Ave. in South Winchester. Unit fronts on main project entry way. 963 square feet with open area, small office, kitchenette, and restroom. Condomium unit with common area services and exterior building maintenance. Professionally managed. Reputable service and professional neighbors. Unit is clean and offered "as is". Please review Opequon Center website for condo documents and other important information. Listing agent must be present at all showings.

3042 Valley, Unit 102, Winchester

Listing courtesy of Merrifield Realty, LLC. Contact:

Selling Office: Realty FC.

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