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318 E Piccadilly St, Winchester
$375,000
4 Beds ⋅ 2 Baths
This delightful brick Colonial, perfectly situated in the heart of downtown Winchester, combines classic architecture with modern updates and an unbeatable location close to every downtown amenity, including restaurants, schools, shopping, parks, and major commuter routes. The home welcomes you with a large foyer featuring newly refinished hardwood floors that extend throughout the entire residence, complemented by fresh paint and an abundance of natural light. The remodeled kitchen is a highlight, boasting sleek white cabinetry and new stainless steel appliances, while a convenient half bath is also located on the main level. Upstairs, you will find four generously-sized bedrooms, all with hardwood floors, and an updated full bathroom featuring a custom-tiled, large walk-in shower with a waterfall shower head. A unique sunroom adjacent to one of the bedrooms offers a flexible space perfect for a sitting area, library, home office, or even an oversized walk-in closet. The property also includes a full unfinished basement & attic for storage, large covered front and back porches for outdoor enjoyment, a private yard, and valuable amenities like prime off-street parking and a detached garage/shed. Other updates include new plumbing, new HVAC (dual zone), new windows, electric and lighting. This is a rare opportunity to own a move-in ready home that perfectly balances downtown living with residential comfort and classic charm.

318 E Piccadilly St, Winchester

Listing courtesy of Colony Realty. Contact:

Selling Office: Long & Foster Real Estate, Inc..

518 Yorktowne Pl, Winchester
$272,000
2 Beds ⋅ 2 Baths
This exquisite end-of-row townhouse, underwent a major renovation in 2025, offers a perfect blend of modern luxury and timeless comfort. With two spacious bedrooms and one and a half elegantly appointed bathrooms, this home is designed for both relaxation and entertaining. Step inside to discover a gourmet kitchen that will inspire your culinary adventures. Featuring upgraded granite countertops, kitchen cabinets and stainless steel appliances, including an over the range microwave and dishwasher, this kitchen seamlessly flows into a combination dining area, perfect for intimate gatherings or lively dinner parties. The inviting living spaces are adorned with new plush carpeting and luxury vinyl plank flooring, creating a warm and welcoming atmosphere throughout. Enjoy the convenience of modern living with essential of new appliances such as a washer, dryer, dishwasher, garbage disposal, refrigerator and electric oven/range, ensuring that every need is met. The thoughtfully designed bathroom features a tub shower, providing a serene retreat for unwinding after a long day. Outside, the property boasts a low-maintenance exterior of brick and newly installed vinyl siding, a rear deck, enhancing its curb appeal while allowing you to spend more time enjoying your home. With parking available in front of the townhouse, you will always feel welcome. This residence not only promises a luxurious lifestyle but also offers the comfort of a well-maintained home in excellent condition. Experience the perfect blend of style, functionality, and comfort in this remarkable property.

518 Yorktowne Pl, Winchester

Listing courtesy of Pifer Realty, LLC. Contact:

Selling Office: J&C Real Estate Solution, LLC.

309 W Tevis St, Winchester
$342,000
3 Beds ⋅ 2 Baths
Discover this Charming One-Level Rambler Featuring an Attached Two-Car Garage and a Thoughtful Layout Designed for Comfortable Living. Enjoy Spacious Bedrooms, Walk-In Closets, and a Warm Gas Fireplace that Anchors the Inviting Living Area. The Home Offers a Spacious Eat-In Kitchen, Providing Ample Room for Cooking, Dining, and Daily Gatherings. Step Outside to a Screened-In Deck, Perfect for Relaxing or Entertaining while Overlooking the Backyard. A Large Driveway Ensures Convenient Parking for Residents and Guests Alike. The Home Needs Cosmetics to Make Shine, Presenting a Fantastic Opportunity to Add Your Personal Touches and Unlock it's Full Potential. Don’t Miss this Exceptional Chance to Create Value and Make this Comfortable Rambler Your Own! Sold As-Is.

309 W Tevis St, Winchester

Listing courtesy of ANR Realty, LLC. Contact:

Selling Office: RE/MAX Roots.

1829 Harvest Dr, Winchester
$399,990
4 Beds ⋅ 4 Baths
1829 Harvest Drive is an attractive end unit new 3 level townhome with full brick front in Winchester, VA for January move-in. Our modern Adams II floorplan features a 1-car garage, and a bedroom and full bathroom on the first floor. Stained Oak stairs lead you to the main level with LVP Floors. The kitchen is equipped with beautiful quartz countertops, white cabinets, and stainless-steel appliances. The upper floor offers 3 bedrooms including a spacious owner's suite with a private bath and large walk-in closet and a convenient bedroom level laundry. Abrams Crossing at Meadow Branch features a fully walkable location and offers convenient access to I-81 and all major commute routes. It's close to shopping, restaurants, and Winchester Medical Center. Featuring America's Smart Home, D.R. Horton keeps you close to the people and places you value most. Simplify your life with a dream home that features hands-free communication, remote keyless entry, video doorbell, and so much more! It’s a home that adapts to your lifestyle. And with D.R. Horton's simple buying process and ten-year limited warranty, there's no reason to wait. Up to $10,000 total closing cost assistance with closing by 1/31/26. *Photos, 3D tours, and videos are representative of plan only and may vary as built.

1829 Harvest Dr, Winchester

Listing courtesy of D R Horton Realty of Virginia LLC. Contact:

Selling Office: Samson Properties.

2708 Cassidy Ct, Winchester
$650,000
5 Beds ⋅ 4 Baths
Rolling Hills Estates located in the Winchester City area, this beautifully maintained 5-bedroom, 3.5-bath home offers 3,552 sq ft of finished living space on a .35-acre cul-de-sac lot. Featuring a 3-car garage w/220 Car Charger, fully fenced backyard, covered front porch, and a rear Trex deck with lighting and stairs to the yard, this home is built for comfortable living and entertaining. Inside, the main level boasts hardwood flooring, an open floorplan, a gourmet kitchen with granite countertops, stainless steel appliances, island, under counter lighting, tile backsplash, butler’s pantry, wine/beverage fridge, separate dining room, and a cozy family room with fireplace. The play area can be used as an office or library. Upstairs, the spacious primary suite includes an ensuite bath and walk-in closet, along with three additional bedrooms, a full bath, and convenient upper-level laundry. The finished walk-out basement adds a private bedroom and full bath, recreation room, office/flex room, and storage. Minutes from Historic Winchester, Shenandoah University, I-81, Route 7, shopping, restaurants, the exciting Cedar Valley project that is underway includes a 50,325-square-foot Publix Super Market, set to open by March 2027, alongside 327 residential units—comprising townhomes, condominiums, and apartments—and 22,600 square feet of commercial and retail space. A four-level, 376-space parking garage with rooftop recreational facilities, such as pickleball courts, will further enhance the area’s appeal & MORE. Just in time to celebrate the holidays in your next home!

2708 Cassidy Ct, Winchester

Listing courtesy of Hunt Country Sotheby's International Realty. Contact:

Selling Office: Samson Properties.

423 Highland Ave, Winchester
$270,000
3 Beds ⋅ 2 Baths
✨ Charming Winchester Home – Don’t Let This One Slip Away! Welcome to this beautifully refreshed home in the heart of Winchester, offering exceptional value, versatility, and convenience. Thoughtfully updated throughout, this property is move-in ready while still leaving room to make it your own. Enjoy ample off-street parking for up to 8 cars with rear access from West Lane, fresh renovations, brand-new vinyl flooring on the main level, and a new upstairs deck — perfect for morning coffee or evening relaxation. Property Highlights: 🛏️ 3 spacious bedrooms filled with natural light 🛁 2 full bathrooms — one on each level, with main-level laundry for added convenience 🏡 Flexible main-level office or bonus room — ideal as a home office, guest room, or cozy reading nook 🌳 Fully fenced backyard perfect for entertaining, pets, or peaceful outdoor enjoyment 🪴 New upstairs deck offering additional outdoor living space 🚗 Rear-alley parking with entry from West Lane, providing privacy, convenience, and space for up to 8 vehicles Perfectly located near downtown Winchester, shops, dining, and commuter routes, this home combines charm, practicality, and potential — all at an unbeatable price. 📅 Don’t miss this opportunity! Schedule your tour today!

423 Highland Ave, Winchester

Listing courtesy of Samson Properties. Contact:

Selling Office: Vaze Realty.

7 N Purcell Ave, Winchester
$376,250
3 Beds ⋅ 3 Baths
Welcome to this thoughtfully updated, truly move-in-ready Cape Cod at 7 N Purcell Ave in Winchester! As you step inside, you’ll be greeted by beautiful hardwood floors flowing through the spacious and light-filled living room. The charming eat-in kitchen features modern quartz countertops, a farmhouse-style sink, and plenty of cabinet space—perfect for everyday meals or entertaining. Retreat to the luxurious primary suite, complete with a walk-in closet and a private en-suite bathroom—your ideal space for rest and relaxation. The home offers updated full bathrooms on both levels, as well as brand-new carpet (2025). The finished bonus room in the basement provides wonderful flexibility—use it as a recreation room, home office, den, or anything your lifestyle needs. You’ll also find convenient laundry and storage areas downstairs. Step outside to a fully fenced backyard with a spacious patio, perfect for outdoor entertaining, play, and pets. A detached one-car garage offers additional storage, a work area, and an attic. Major improvements include a new roof and hot water heater (2025), with central AC and furnace approximately 10 years old. Located in a highly convenient area, this home is walking distance to Daniel Morgan Middle School and just minutes from Old Town Winchester’s Walking Mall, shopping, parks, Winchester Medical Center, Shenandoah University, and major commuter routes. Don’t miss your chance to see this wonderful home—schedule your showing today!

7 N Purcell Ave, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

Selling Office: Real Broker, LLC.

1415 Ramseur Ln, Winchester
$130,000
This 0.16-acre lot is a rare opportunity to own a homesite in the desirable Early’s Green at Meadowbranch subdivision, located in the heart of Winchester. Nestled within a beautifully maintained community, this property offers access to fantastic amenities including common grounds, a swimming pool, and tennis courts—perfect for enjoying an active and social lifestyle. Conveniently located near schools, shopping and dining destinations, entertainment, and just minutes from Winchester Medical Center and downtown Winchester, this lot offers both comfort and convenience. Whether you're looking to build your forever home or invest in one of Winchester's most sought-after neighborhoods, this lot is a must-see.

1415 Ramseur Ln, Winchester

Listing courtesy of RE/MAX Roots. Contact:

Selling Office: Coldwell Banker Premier.

510 S Washington St, Winchester
$537,500
3 Beds ⋅ 2 Baths
Welcome to a piece of Winchester History. This historic Colonial Revival residence, built of enduring brick construction, offers an opportunity of owning a significant piece of the city's heritage. Situated on a .20 city acre lot, this property is ideally positioned directly on the route of the Shenandoah Apple Blossom Festival Parade, offering unparalleled viewing opportunities. With winter approaching, it is a perfect time to grab a book from the built-in bookcases and snuggle by the fireplace in the generously sized living room. Spring will bring a perfect opportunity to start those seedlings on the 3 season porch. Head upstairs to a thoughtfully designed floor plan that balances comfort and privacy. The primary bedroom, a private oasis located on the right side of the home, features a cozy window seat and dual closets. Two additional bedrooms are situated on the left, offering optimal separation from the primary suite. One of these bedrooms provides direct access to the balcony for nature views in the backyard. Don't forget the finished attic, a versatile bonus space perfect for a play area, art studio, music room, study, office, or simply extra storage! A partial basement for additional square footage and a laundry room with a shower and sump pump which may provide an opportunity to add a water closet. Off street parking and garage accessible by the alley off of Leicester Street

510 S Washington St, Winchester

Listing courtesy of Century 21 Modern Realty Results. Contact:

Selling Office: Colony Realty.

225 Fox Dr, Winchester
$395,000
3 Beds ⋅ 2 Baths
Welcome to 225 Fox Drive — a beautifully maintained all-brick rancher offering comfort, efficiency, and convenience in one ideal package. This 3-bedroom, 1.5-bath home features a bright and upgraded kitchen with quartz countertops, new cabinetry, stainless steel appliances, and an induction stove. Hardwood floors flow throughout the main level, adding warmth and timeless charm. A full walk-up basement provides excellent potential for storage, hobbies, or future expansion. Modern upgrades make this home truly stand out, including Enphase Solar Panels (22 panels), an EV charger, and an RV charger, delivering impressive energy efficiency and future-ready functionality. Step outside to a peaceful, fully fenced backyard (installed in 2022) complete with a fire pit, gazebos, and a patio—perfect for unwinding or entertaining guests. The detached garage/workshop, newly rewired in 2024, offers fantastic additional space for projects or storage. Located just one mile from Winchester Medical Center and within walking distance of The Museum of the Shenandoah Valley Walking Trails, this home combines quality updates with everyday convenience in an ideal city location. A true must-see!

225 Fox Dr, Winchester

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

Selling Office: First Decision Realty LLC.

400 Handley Ave, Winchester
$615,900
3 Beds ⋅ 3 Baths
Welcome to this beautifully preserved American brick Foursquare, an exceptional home that perfectly blends early 20th-century charm with modern updates. Nestled in one of Winchester’s most sought-after neighborhoods, this home is just two blocks from the annual Apple Blossom Parade , a short stroll to Old Town Winchester’s historic walking mall, and Handley High School. From the moment you arrive, you’ll be captivated by the classic architecture, large covered front and rear porches, and the lovingly landscaped yard featuring mature azaleas, crepe myrtles, and perennial blooms—a low-maintenance garden that bursts with color year after year. On the Main level, the home showcases original heart pine floors, intricate moldings, and solid wood doors with original hardware, all beautifully maintained. The inviting living room flows effortlessly into the formal dining room, creating an ideal setting for entertaining. The updated kitchen features quartz countertops, stainless steel appliances, recessed lighting, and a charming coffee bar with access to the rear porch. A convenient half bath completes the main level. Upstairs, with two staircases providing access, you’ll find three spacious bedrooms, each with original flooring and trim, and a full bath featuring a classic clawfoot soaking tub and separate shower. The four season sunroom off the primary bedroom provides a serene retreat with abundant natural light—perfect for reading, morning coffee, or simply relaxing. A laundry room on this level adds everyday convenience. The fully finished third-floor attic offers a remarkable, light-filled space with built-in storage, a wet bar with sink and mini-fridge, and a full bath with tiled floors and glass shower doors. This versatile area could serve as an art studio, guest suite, teen retreat, or home office—the possibilities are endless. Outside, you’ll enjoy two classic southern-style brick porches ideal for outdoor dining and entertaining. The property also includes a one-car garage and driveway. Modern upgrades include newer central heating and air conditioning, updated wiring, and back-up oil radiant heat for added comfort. Positioned on the corner of West Cecil Street and Handley Avenue, this home offers both charm and convenience, surrounded by other beautifully maintained properties and a walkable neighborhood. Schedule your appointment today !

400 Handley Ave, Winchester

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

Selling Office: Smart Realty, LLC.

352 Sheridan Ave, Winchester
$599,000
4 Beds ⋅ 3 Baths
Just steps from Handley High School, this charming all-brick rancher offers the kind of space, character, and updates that rarely come available in downtown Winchester. Set on a wonderful tree-lined street, this home welcomes you with bright, airy living spaces and an easy, comfortable flow. The kitchen has been thoughtfully updated with new appliances and stylish finishes, blending modern convenience with timeless appeal. Throughout the main level, generous room sizes and abundant natural light create a warm, inviting atmosphere you’ll feel the moment you walk in. Downstairs, the large basement features brand-new flooring, another bedroom and a full bathroom plus a large sitting area, perfect for a theater room. Important upgrades have been completed for peace of mind, including a newer electrical panel (2019), a radon mitigation system, upgraded lighting with LED recessed fixtures, and the addition of Mysa thermostat systems for smart, efficient comfort throughout the home. Outdoors, the property blooms through every season with established landscaping and a fully fenced backyard designed for play, pets, and peaceful moments. Stylish, solid, and beautifully updated, this home offers the convenience of city living with the comfort of a thoughtfully redesigned interior. It’s truly a place you’ll love coming home to.

352 Sheridan Ave, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

Selling Office: Realty ONE Group Old Towne.

1810 Blythe Way, Winchester
$406,300
4 Beds ⋅ 4 Baths
1810 Blythe Way is an attractive new 3 level townhome with full brick front in Winchester, VA for November move-in. Our modern Adams floorplan features a 1-car garage, and along with a bedroom and full bathroom on the first floor. Stained Oak stairs lead you to the main level with LVP Floors. The kitchen is equipped with beautiful Quartz countertops, white cabinets, and stainless-steel appliances. The upper floor offers 3 bedrooms including a spacious owner's suite with a private bath and large walk-in closet and a convenient bedroom level laundry. Abrams Crossing at Meadow Branch features a fully walkable location and offers convenient access to I-81 and all major commute routes. It's close to shopping, restaurants, and Winchester Medical Center. Featuring America's Smart Home, D.R. Horton keeps you close to the people and places you value most. Simplify your life with a dream home that features hands-free communication, remote keyless entry, video doorbell, and so much more! It’s a home that adapts to your lifestyle. And with D.R. Horton's simple buying process and ten-year limited warranty, there's no reason to wait. Up to $6,500 total closing cost is tied to the use of DHI Mortgage. *Photos, 3D tours, and videos are representative of plan only and may vary as built.*

1810 Blythe Way, Winchester

Listing courtesy of D R Horton Realty of Virginia LLC. Contact:

Selling Office: Non Subscribing Office.

703 National Ave, Winchester
$469,000
3 Beds ⋅ 3 Baths
Fully renovated in 2025, this 3-bedroom, 2.5-bath home is ideally located within Winchester city limits—just a short walk to the vibrant downtown walking mall with its shops, dining, and entertainment, as well as Jim Barnett Park for outdoor recreation. Thoughtful updates and fresh landscaping enhance its curb appeal. Inside, you’ll find brand-new bathrooms with updated lighting, vanities, toilets, faucets, tubs, and showers. The home features new vinyl plank and ceramic tile flooring, a completely redesigned kitchen with new cabinets, granite countertops, a center island, and stainless steel appliances. The entire interior has been freshly painted in a neutral palette and finished with new interior doors and custom trim. Additional improvements include all new electrical entrance and wiring (plugs, switches, and lights), new insulation/sheetrock, a brand-new water heater, and two new HVAC units. Exterior upgrades completed in 2025 include new siding, a new roof (30-year architectural shingles), most windows replaced, and new decking and rails on both the front and rear porches—perfect for relaxing or entertaining. A storage shed conveys as-is. *Agent is related to owner* The information contained herein is for informational purposes only. RE/MAX Roots makes no representation as to the accuracy or reliability of the information. The buyer is to verify information provided and related to the property that is material to a buyer’s decision to purchase the property. All documents and other information attached to this listing are provided as a courtesy and should be researched and verified by the buyer agent.

703 National Ave, Winchester

Listing courtesy of RE/MAX Roots. Contact:

Selling Office: ERA Oakcrest Realty, Inc..

1802 Blythe Way, Winchester
$399,990
4 Beds ⋅ 4 Baths
1802 Blythe Way is an attractive new 3 level end townhome with full brick front in Winchester, VA for January move-in. Our modern Adams floorplan features a 1-car garage, and along with a bedroom and full bathroom on the first floor. Stained Oak stairs lead you to the main level with LVP Floors. The kitchen is equipped with beautiful Quartz countertops, white cabinets, and stainless-steel appliances. The upper floor offers 3 bedrooms including a spacious owner's suite with a private bath and large walk-in closet and a convenient bedroom level laundry. Abrams Crossing at Meadow Branch features a fully walkable location and offers convenient access to I-81 and all major commute routes. It's close to shopping, restaurants, and Winchester Medical Center. Featuring America's Smart Home, D.R. Horton keeps you close to the people and places you value most. Simplify your life with a dream home that features hands-free communication, remote keyless entry, video doorbell, and so much more! It’s a home that adapts to your lifestyle. And with D.R. Horton's simple buying process and ten-year limited warranty, there's no reason to wait. Up to $10,000 total closing cost assistance with closing by 12/31/25. *Photos, 3D tours, and videos are representative of plan only and may vary as built.

1802 Blythe Way, Winchester

Listing courtesy of D R Horton Realty of Virginia LLC. Contact:

Selling Office: Spring Hill Real Estate, LLC..

2812 Ridgetop Ct, Winchester
$525,000
4 Beds ⋅ 4 Baths
HUGE PRICE IMPROVEMENT! Welcome to this beautiful "picture perfect" brick front 4-bedroom, 3.5-bath home in the desirable Rolling Hills community of Winchester, VA. Perfectly located at the end of a cul-de-sac in an established (and sought after) neighborhood, this one-owner property has been meticulously maintained and is ready for its next chapter. Inside, you’ll find a spacious and inviting layout that includes a bright living room with a beautiful fireplace, perfect for relaxing or entertaining. High ceilings (9 foot!) on BOTH the main and top level makes the space feel even larger! The kitchen has been thoughtfully upgraded and is truly a chef’s dream, featuring a gas stove, double oven, and high-quality finishes. Upstairs, generous bedrooms provide comfort and privacy, while the primary suite (with a tray ceiling!) offers a relaxing retreat. The home also boasts a mostly finished basement, providing flexible space for a recreation room, home office, or gym. There is a full bathroom down there too! Recent updates include a NEW roof and a newer deck, ideal for enjoying the outdoors. The pride of ownership extends beyond the interior, with a beautifully landscaped yard enhanced by hand selected trees and thoughtful plantings, offering both curb appeal and a peaceful setting. Centrally located to shopping, dining, schools, and major commuter routes, yet tucked away in a quiet neighborhood, this property provides the perfect balance of convenience and tranquility. Don’t miss this opportunity to own a truly special home in one of Winchester’s most sought-after communities.

2812 Ridgetop Ct, Winchester

Listing courtesy of RE/MAX Distinctive Real Estate. Contact:

Selling Office: RE/MAX Distinctive Real Estate.

312 Fox Dr, Winchester
$380,000
3 Beds ⋅ 1 Baths
Welcome to this charming all brick ranch style home nestled on a spacious 0.34-acre lot conveniently located in the City of Winchester. Built in 1959, this home has been well maintained and offers approximately 1,105 sq ft of living space with 3 bedrooms and 1 full bath, hardwood floors, a low maintenance yard that is well manicured, and a 1-car attached carport. This home presents an excellent opportunity to personalize and upgrade to your taste, so don’t miss out!! This well established neighborhood provides easy access to amenities, schools and commuter routes, placing you minutes from downtown Winchester and conveniences. Winchester sits in the Shenandoah Valley and offers easy access to outdoor recreation: hiking, nature, trails, pretty scenery. It has a smaller city/town feel but is not too isolated as you have the benefits of more space and slower pace, but still plenty of amenities. Because of its location, it is attractive for people wanting to escape the high cost metro areas but still be within reach. Enjoy the pedestrian walking mall, restaurants, shops, farmers markets, festivals, and historical architecture.

312 Fox Dr, Winchester

Listing courtesy of Keller Williams Realty. Contact:

Selling Office: Tempo Realty.

214 S Braddock St, Winchester
$382,000
5 Beds ⋅ 2 Baths
This property is currently zoned as fully commercial but has the potential to be changed to: Mixed Use or Fully Residential with proper city approval. Additional information from city located in documents. This home will need a Kitchen. Situated in Downtown Winchester, 214 S Braddock is waiting for your ideas! Built in 1865, this home features historic charm including exposed brick walls, beautiful hardwood floors, crown molding, original fireplaces, and super high ceilings, this space is sure to impress! This home is a lot larger than it appears from the outside! Large front porch leads to a space that would be ideal for a enjoying your coffee in the morning or relaxing after a long day! The first floor features 3 open/flex spaces plus a room with a wet bar that could be used as a breakroom and a full bathroom. Upstairs there are an additional two spaces with great natural light, a full bathroom, and an additional LARGE room that has an adjoining room for even more possibilities. The basement has a ton of storage options and also a door that leads to the parking lot with 5 coveted spaces reserved for tenants and their clients. Some updates have been made, but the owner will consider some upgrade requests.

214 S Braddock St, Winchester

Listing courtesy of Keller Williams Realty. Contact:

Selling Office: Weichert, REALTORS.

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