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Classy colonial on the stately Fairmont Avenue with million dollar homes nearby, walking mall in close proximity with a plethora of boutique shops and eateries. The 2000 square feet is designed for comfort and coziness accented by 9ft ceilings, sunlit formal rooms, a well appointed kitchen, spacious bedrooms, adorable loft on 3rd level for a playroom/den/office, and the best part is entering your private courtyard for relaxation, green thumb activity, and entertaining friends and family. Semi-circle driveway and plenty of storage in the basement make a case for you to definitely consider this your downtown home.

216 Fairmont Ave, Winchester

Listing courtesy of RE/MAX Roots. Contact:

Selling Office: Samson Properties.

$464,000

READY FOR BUYER! TURN KEY classic colonial, fully UPDATED, and WALKABLE to downtown! *3 LEVELS totalling 2568 SF* Stroll to the restaurants in Old Town, enjoy the activities at Handley, or walk to the trails at MSV! NEW roof, HVAC, privacy fencing, custom paint and built-in cabinetry, plus new stainless steel appliances, including washer/dryer. Get creative in the FINISHED LOWER LEVEL with walk-out! Perhaps a swanky whiskey lounge, zen yoga studio, quiet kids play area, home office, or 4th bedroom, complete with 1/2 bath (also plumbed for shower). Cozy up to the recently serviced FIREPLACE this winter, and in spring, summer, and fall, relax on the spacious BACK DECK, overlooking a custom pollinator garden and your FENCED, private backyard. Gleaming hardwood floors, tons of windows, and FULLY MODERNIZED throughout! If convenience, walkability, meticulously maintained, move-in ready, and AFFORDABILITY, are your goals, 407 Jefferson is the home for you!

3 Beds ⋅ 3 Baths

READY FOR BUYER! TURN KEY classic colonial, fully UPDATED, and WALKABLE to downtown! *3 LEVELS totalling 2568 SF* Stroll to the restaurants in Old Town, enjoy the activities at Handley, or walk to the trails at MSV! NEW roof, HVAC, privacy fencing, custom paint and built-in cabinetry, plus new stainless steel appliances, including washer/dryer. Get creative in the FINISHED LOWER LEVEL with walk-out! Perhaps a swanky whiskey lounge, zen yoga studio, quiet kids play area, home office, or 4th bedroom, complete with 1/2 bath (also plumbed for shower). Cozy up to the recently serviced FIREPLACE this winter, and in spring, summer, and fall, relax on the spacious BACK DECK, overlooking a custom pollinator garden and your FENCED, private backyard. Gleaming hardwood floors, tons of windows, and FULLY MODERNIZED throughout! If convenience, walkability, meticulously maintained, move-in ready, and AFFORDABILITY, are your goals, 407 Jefferson is the home for you!

407 Jefferson St, Winchester

Listing courtesy of Coldwell Banker Premier. Contact:

Selling Office: Colony Realty.

$459,000

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.

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.

$398,000

Must see this Newly Renovated 4–5-bedroom 2 Full bath, Main level has Brand New Kitchen Cabinets with Granite Counters & Stainless-Steel Appliances. Living room and two Good Size Bedrooms & a Full Bathroom with a Walk-in Shower, Main level Laundry. Up to the 2nd level are Two Bedrooms & Full Bath. 3 Finished levels with a Finished room in the Basement with additional room to Grow. Walkout level to a Large Fenced Backyard. Natural Gas Heat & Gas Hot Water & Central A/C. Relax on either one of the Front or Back Covered Trex Porch, New Roof. The Home is much larger than it appears.

Must see this Newly Renovated 4–5-bedroom 2 Full bath, Main level has Brand New Kitchen Cabinets with Granite Counters & Stainless-Steel Appliances. Living room and two Good Size Bedrooms & a Full Bathroom with a Walk-in Shower, Main level Laundry. Up to the 2nd level are Two Bedrooms & Full Bath. 3 Finished levels with a Finished room in the Basement with additional room to Grow. Walkout level to a Large Fenced Backyard. Natural Gas Heat & Gas Hot Water & Central A/C. Relax on either one of the Front or Back Covered Trex Porch, New Roof. The Home is much larger than it appears.

232 Myrtle Ave, Winchester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Selling Office: Pearson Smith Realty, LLC.

$380,000

Charming Home Near Handley High School – Move-In Ready! Welcome to this beautifully updated home in a fantastic downtown location—just a short walk to shops, restaurants, and all that the vibrant city center has to offer. This property features a converted garage that now serves as a versatile studio space, perfect for a home office, art studio, or guest suite. Enjoy a spacious, fenced-in backyard ideal for entertaining, gardening, or relaxing. Recent updates include a new HVAC system, hot water tank, and a brand-new deck—giving you peace of mind and great outdoor living space. Don't miss your chance to own a wonderful home in one of the most desirable locations in town!

Charming Home Near Handley High School – Move-In Ready! Welcome to this beautifully updated home in a fantastic downtown location—just a short walk to shops, restaurants, and all that the vibrant city center has to offer. This property features a converted garage that now serves as a versatile studio space, perfect for a home office, art studio, or guest suite. Enjoy a spacious, fenced-in backyard ideal for entertaining, gardening, or relaxing. Recent updates include a new HVAC system, hot water tank, and a brand-new deck—giving you peace of mind and great outdoor living space. Don't miss your chance to own a wonderful home in one of the most desirable locations in town!

31 W Whitlock Ave, Winchester

Listing courtesy of Link Realty Services LLC. Contact:

Selling Office: Colony Realty.

$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.

$340,000

Buyer Financing Has Fallen Through – Seller is Highly Motivated!!!!. A classic brick ranch in Winchester, VA, has three bedrooms and two full bathrooms. The basement includes a separate entrance, a laundry area, a full bathroom, and an additional bonus room. Recent updates include: finished basement, new HVAC system, complete renovations of both bathrooms, new hardwood flooring, and an updated kitchen with new cabinets and countertops. No HOA restrictions. Don't miss your chance to see this inviting home—schedule a visit!

Buyer Financing Has Fallen Through – Seller is Highly Motivated!!!!. A classic brick ranch in Winchester, VA, has three bedrooms and two full bathrooms. The basement includes a separate entrance, a laundry area, a full bathroom, and an additional bonus room. Recent updates include: finished basement, new HVAC system, complete renovations of both bathrooms, new hardwood flooring, and an updated kitchen with new cabinets and countertops. No HOA restrictions. Don't miss your chance to see this inviting home—schedule a visit!

1005 Pennsylvania Ave, Winchester

Listing courtesy of Spring Hill Real Estate, LLC.. Contact:

Selling Office: MarketPlace REALTY.

$337,000

Life in Historic Winchester just got easier with this modern construction. Built in 2004, this Charming 3 Bedroom, 1.5 Bath home is the best of all worlds. This home has been completely & professionally remodeled in 2025 and the quality of construction shows. Fresh and bright you will find that practically everything is new. Enter to find newly finished gleaming hardwood floors (2025), crisp new paint and trim(2025) throughout. Generous family room flows into completely renovated kitchen. Kitchen is up to date (2025) with Brand New stainless appliances, counters, flooring, sink and handy laundry area with hook-up for washer and dryer, plus a half bath ( with all new fixtures) is tucked away for convenience. Flow through beautiful sliding doors to nicely sized deck overlooking large, fully fenced lawn with space to play and garden. Relaxation happens here! Upstairs, find gorgeous new carpet in all areas, 3 Bedrooms, a beautifully remodeled bathroom with all new fixtures and blinds. Exterior of the home has just been freshly painted, too. New Water Heater 2025. There is no deferred maintenance in this charming home. Located within easy walking distance of Old Town Pedestrian Mall, The Handley Library, Restaurants, Galleries, Museums, Coffee Shops and Boutiques. Call for a tour today.

Life in Historic Winchester just got easier with this modern construction. Built in 2004, this Charming 3 Bedroom, 1.5 Bath home is the best of all worlds. This home has been completely & professionally remodeled in 2025 and the quality of construction shows. Fresh and bright you will find that practically everything is new. Enter to find newly finished gleaming hardwood floors (2025), crisp new paint and trim(2025) throughout. Generous family room flows into completely renovated kitchen. Kitchen is up to date (2025) with Brand New stainless appliances, counters, flooring, sink and handy laundry area with hook-up for washer and dryer, plus a half bath ( with all new fixtures) is tucked away for convenience. Flow through beautiful sliding doors to nicely sized deck overlooking large, fully fenced lawn with space to play and garden. Relaxation happens here! Upstairs, find gorgeous new carpet in all areas, 3 Bedrooms, a beautifully remodeled bathroom with all new fixtures and blinds. Exterior of the home has just been freshly painted, too. New Water Heater 2025. There is no deferred maintenance in this charming home. Located within easy walking distance of Old Town Pedestrian Mall, The Handley Library, Restaurants, Galleries, Museums, Coffee Shops and Boutiques. Call for a tour today.

19 W Germain St, Winchester

Listing courtesy of MarketPlace REALTY. Contact:

Selling Office: Real Broker, 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.

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.

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.

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.

$325,000

Completely renovated four-bedroom, two-bath home in Winchester. Upgraded kitchen with new 42-inch cabinets, quartz countertops, and brand new appliances. Tastefully painted, new windows, new flooring, new HVAC, upgraded electric fixtures, and plumbing. Totally remodeled bathrooms. Very spacious walkout basement with a bedroom and bath. Huge flat backyard with a stone patio. Excellent commuter location just a block from Route 7 and I-81

Completely renovated four-bedroom, two-bath home in Winchester. Upgraded kitchen with new 42-inch cabinets, quartz countertops, and brand new appliances. Tastefully painted, new windows, new flooring, new HVAC, upgraded electric fixtures, and plumbing. Totally remodeled bathrooms. Very spacious walkout basement with a bedroom and bath. Huge flat backyard with a stone patio. Excellent commuter location just a block from Route 7 and I-81

414 Elm St, Winchester

Listing courtesy of First Decision Realty LLC. Contact:

Selling Office: The Vasquez Group LLC.

$295,000

Wonderful Light filled 2 story Mid-Century Bungalow Updated for Modern Living while Maintaining its Original Charm and Style. An inviting Front Porch with Fabulous Wood Floors runs the length of the front of the home. Enter and Enjoy Beautiful Laminate Plank Floors and Arched Doorways and Recessed Lighting throughout the Main Floor. The Eat In Kitchen maintains it’s Cottage Core Aesthetic. 2 Bedrooms and 1 full Bath that Features Charming Modern Cottage Tile. Walk through the kitchen to the backdoor and you can sit in the Screened in back porch and look out on your beautiful improved level yard dotted with a few mature trees that add to the charming landscape. Dual Aspect Windows in the main living area, kitchen and bedrooms provide a cross-breeze when opened. HVAC 2024. There is also approx 688 additional square ft of Unfinished Basement that provides many possibilities. The following Updates and Additions include An HVAC System installed to provide to provide Air conditioning for the first time in this home (installed 2024). This Goodman A/C Unit also provides Electric Heat – (replacing original baseboard heater and furnace system) . Recessed lighting was added throughout the main floor and on front porch. Yard was improved and a Charming Shed was added in 2024. Water Heater Replaced in 2019. A breezeway was built in 2025 to connect the carport to the back porch Entrance. Outdoor motion sensor lighting in the carport and back of the house. The basement provides the opportunity to build out rooms and there are 2 working a/c vents in place in two areas of the basement ready for you to build your desired space be it hobby room, office, or a gym. Windows on both levels have been replaced, This property sits on .3 acres and is located within the limits of the Historic City of Winchester close to parks, shopping, restaurants, Shenandoah University, Historic Downtown and all located in the beautiful Shenandoah Valley.

Wonderful Light filled 2 story Mid-Century Bungalow Updated for Modern Living while Maintaining its Original Charm and Style. An inviting Front Porch with Fabulous Wood Floors runs the length of the front of the home. Enter and Enjoy Beautiful Laminate Plank Floors and Arched Doorways and Recessed Lighting throughout the Main Floor. The Eat In Kitchen maintains it’s Cottage Core Aesthetic. 2 Bedrooms and 1 full Bath that Features Charming Modern Cottage Tile. Walk through the kitchen to the backdoor and you can sit in the Screened in back porch and look out on your beautiful improved level yard dotted with a few mature trees that add to the charming landscape. Dual Aspect Windows in the main living area, kitchen and bedrooms provide a cross-breeze when opened. HVAC 2024. There is also approx 688 additional square ft of Unfinished Basement that provides many possibilities. The following Updates and Additions include An HVAC System installed to provide to provide Air conditioning for the first time in this home (installed 2024). This Goodman A/C Unit also provides Electric Heat – (replacing original baseboard heater and furnace system) . Recessed lighting was added throughout the main floor and on front porch. Yard was improved and a Charming Shed was added in 2024. Water Heater Replaced in 2019. A breezeway was built in 2025 to connect the carport to the back porch Entrance. Outdoor motion sensor lighting in the carport and back of the house. The basement provides the opportunity to build out rooms and there are 2 working a/c vents in place in two areas of the basement ready for you to build your desired space be it hobby room, office, or a gym. Windows on both levels have been replaced, This property sits on .3 acres and is located within the limits of the Historic City of Winchester close to parks, shopping, restaurants, Shenandoah University, Historic Downtown and all located in the beautiful Shenandoah Valley.

2964 Grace St, Winchester

Listing courtesy of United Real Estate. Contact:

Selling Office: Non Subscribing Office.

$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.

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.

$279,000

This is a completely restored Winchester classic within walking distance to the downtown area and Handley High school. Located at the end of street. Home improvements include new HVAC, plumbing, electric and appliances. Interior pictures will follow as soon as painting has been completed.

This is a completely restored Winchester classic within walking distance to the downtown area and Handley High school. Located at the end of street. Home improvements include new HVAC, plumbing, electric and appliances. Interior pictures will follow as soon as painting has been completed.

20 E Hart St, Winchester

Listing courtesy of Link Realty Services LLC. Contact:

Selling Office: Realty ONE Group Old Towne.

$270,000

Estate sale, professionally cleaned and ready for move -in located between Loudoun & Cameron Streets, convenient to old town Winchester, shopping, restaurants, fun old towne events, commuter routes. Brick and Vinyl exterior, walkout basement large rear deck ideal for enjoying sunsets or entertaining. Second floor bedrooms and main level living room are carpeted. Kitchen, hallway and bath rooms are tiled. Sale AS-IS.

Estate sale, professionally cleaned and ready for move -in located between Loudoun & Cameron Streets, convenient to old town Winchester, shopping, restaurants, fun old towne events, commuter routes. Brick and Vinyl exterior, walkout basement large rear deck ideal for enjoying sunsets or entertaining. Second floor bedrooms and main level living room are carpeted. Kitchen, hallway and bath rooms are tiled. Sale AS-IS.

13 E Hart St, Winchester

Listing courtesy of MarketPlace REALTY. Contact:

Selling Office: Unrepresented Buyer Office.

$266,000

Welcome to this centrally located home in the heart of Winchester. With easy access to I-81, this home is in a great commuter's location. Just a quick walk or drive away are the charming shops and restaurants of Historic Old Town Winchester. The main level features hardwood floors, a living room with wood-burning brick fireplace and a formal dining room, featuring a charming a built in China cabinet. Upstairs are 3 bedrooms with double closets. and a full bathroom. Enjoy the convenience of a first floor full bathroom as well. This home offers a spacious backyard and plenty of parking space for your family and friends.

Welcome to this centrally located home in the heart of Winchester. With easy access to I-81, this home is in a great commuter's location. Just a quick walk or drive away are the charming shops and restaurants of Historic Old Town Winchester. The main level features hardwood floors, a living room with wood-burning brick fireplace and a formal dining room, featuring a charming a built in China cabinet. Upstairs are 3 bedrooms with double closets. and a full bathroom. Enjoy the convenience of a first floor full bathroom as well. This home offers a spacious backyard and plenty of parking space for your family and friends.

320 Highland Ave, Winchester

Listing courtesy of Samson Properties. Contact:

Selling Office: Keller Williams Realty.

$181,000

Great investor opportunity in the heart of Winchester! The LOWEST priced detached house within a 10-mile radius!! This 3-level home with a 2-car detached garage on a level treed lot is ideal for investors looking to fix and flip or fix and hold, with Shenandoah University only 3 miles away and Winchester Medical Center only 4 miles away. This detached 1933 front porch Cottage home on .20 acre lot sold strictly 'As-Is.' The house has one bedroom on the main level with a full bathroom, living room, and kitchen, plus a finished upper level with a 2nd large bedroom and an unfinished basement on public water and sewer with no HOA. Fabulous location just minutes to the historic city center and major commuting routes. Walking distance to historic Winchester shops, restaurants, and breweries. Close to Jim Barnett Park and the MSV hiking trails.