Winchester City Public Schools Homes under $400,000

Winchester City Public Schools Homes under $400,000

Welcome to Winchester, Virginia, where the charm of a historic city meets the modern conveniences of family living. One of the key highlights of this vibrant community is the esteemed Winchester City Public Schools. Renowned for its commitment to academic excellence, the district offers a nurturing environment for students, with a diverse range of programs designed to inspire and engage young minds. From innovative STEM initiatives to robust arts and athletics, families can rest assured that their children will receive a well-rounded education tailored to their individual needs.

For those considering making Winchester their home, you'll be delighted to discover a variety of charming properties available under $400,000. This price point opens up a world of possibilities, offering a range of options from cozy single-family homes to inviting townhouses. Many of these residences feature modern amenities while still retaining the historical character that Winchester is known for. Imagine settling into a home with spacious yards, perfect for family gatherings, or a quaint front porch where you can enjoy your morning coffee while soaking in the picturesque views of the Blue Ridge Mountains.

Living in Winchester means not only enjoying the benefits of a strong educational system but also embracing a community rich in history and culture. With its friendly neighborhoods, local parks, and vibrant downtown area, Winchester is the perfect place to plant your roots. Explore your options today and discover why so many families are choosing to call Winchester home!

Newest Winchester City Public Schools Homes under $400,000

329 Fairview Ave, Winchester
$255,000
3 Beds ⋅ 2 Baths
329 Fairview Ave is a two-story Winchester single-family home with a bright, window-lined sunroom and a classic covered front porch. Plank flooring runs through the main living areas, where soft neutral walls and generous windows keep each room filled with natural light. The kitchen pairs crisp white cabinetry with ample counter space, a dishwasher, and a built-in microwave above the range. Carpeted bedrooms provide comfortable retreats, and the bathrooms include a tub with a dark tile surround and a wood vanity set against black-and-white mosaic floor tile. Out back, a grassy yard leaves room to garden or unwind outdoors.

329 Fairview Ave, Winchester

Listing courtesy of Open Door Brokerage, LLC. Contact:

322 Highland Ave, Winchester
$289,900
4 Beds ⋅ 3 Baths
SINGLE-FAMILY LIVING IN WINCHESTER WITHOUT THE BIG PRICE TAG! Welcome to 322 Highland Ave, an opportunity to get the space of a 4-bedroom detached home at an approachable price point. With four bedrooms and 2.5 baths, there’s room to spread out, work from home, create a guest room, or simply enjoy the flexibility that extra bedrooms provide. This home is a great option for buyers who have been searching for more space without stretching into the price range of many larger single-family homes in the area. More house. More bedrooms. More possibilities. Come see the value for yourself!

322 Highland Ave, Winchester

Listing courtesy of EXP Realty, LLC. Contact:

2660 Daniel Ter, Winchester
$335,000
2 Beds ⋅ 2 Baths
Well maintained three story, all brick townhome located in the City of Winchester. This home is on a quiet street and conveniently located close to shopping and restaurants. There are hardwood floors throughout the main level consisting of the kitchen/dining area, living room, and half bath. There are two nice sized bedrooms and one full bath on the upper level, along with separate laundry. (Maytag washer and dryer purchased in 2024 convey with property) The lower level has a finished living space with electric baseboard heat and could be comfortably used as a family room, office, or additional bedroom. Directly off the finished lower level are a one car garage and storage area. (The new freezer located in garage also conveys) This townhome comes with plenty of parking, whether it is street parking in front, a private concrete driveway in the rear, or the rear loading garage. (Townhome is being freshly painted throughout.) Townhomes in this subdivision rarely come to market, so don't wait! PROFESSIONAL PHOTOS COMING SOON.

2660 Daniel Ter, Winchester

Listing courtesy of MarketPlace REALTY. Contact:

1308 Commerce, Winchester
$299,900
3 Beds ⋅ 1 Baths
Charming, cheerful, and filled with natural light, this inviting 3-bedroom, 1-bath rancher makes a delightful first impression. Fresh yellow siding, mature trees, blooming hydrangeas, and classic boxwoods create beautiful curb appeal, while convenient main-level living makes the home as practical as it is welcoming. Inside, gleaming hardwood floors and abundant sunlight lend warmth to every room. The beautifully updated bath features a walk-in shower, and the centrally located kitchen offers generous cabinetry and plenty of room for shared meals. Ideally situated between the formal living room and cozy den, the kitchen provides an easy flow for everyday living and entertaining. Rich wood walls and a wood stove give the den its distinctive character. Adding a special piece of Winchester history, the paneling was salvaged from the former Lee-Jackson Hotel banquet room. Downstairs, the climate-controlled, partially finished lower level offers wonderful possibilities for a recreation room, playroom, home gym, or office, along with ample workshop and storage space. A relaxing screened porch overlooks the spacious backyard with peonies and a cherry tree, creating a peaceful spot to enjoy the outdoors. Lovingly cared for by the same family since it was built, this sweet home has been recently painted throughout and features roof (July 2025), new HVAC system (July 2026), update bathroom (2024) and newer 20-year tilt in windows, and updated lighting. Whether you are searching for your first home or looking to downsize, this special property is well worth a visit. Schedule your tour today!

1308 Commerce, Winchester

Listing courtesy of Colony Realty. Contact:

828 Woodland Ave, Winchester
$298,900
2 Beds ⋅ 2 Baths
PRICED TO SELL!!! This all-brick Ranch 2-3 bedrooms, 1.5 bathrooms, kitchen has been updated with granite countertops. Full basement partly finished basement, with workshop on a walk out to back yard. The outside shop is ready to set up shop with plenty of room for storage, and it has Electric! Great yard to enjoy all the seasons and relaxing. All this and so much more for $298,900.00.

828 Woodland Ave, Winchester

Listing courtesy of Samson Properties. Contact:

1013 Orchard Hill Dr, Winchester
$299,900
3 Beds ⋅ 2 Baths
Updated, move-in ready, and waiting for you to make it your own! Welcome to 1013 Orchard Hill Dr. Tucked away in a charming, established Winchester neighborhood with no HOA, this inviting townhome combines a clean, comfortable style with many of the big-ticket improvements already taken care of. Outside, you'll find a brand-new roof and vinyl siding, fresh landscaping, and an updated rear deck complete with durable vinyl railing. Step inside to a spacious main level with an easy, open flow between the living and dining areas. The living room is warm and welcoming, centered around a wood-burning fireplace with built-in cabinetry on both sides, the perfect spot to settle in on a cool evening. The adjoining galley-style kitchen offers plenty of functionality with the laundry conveniently located just off the kitchen. Beyond the dining area, the home gets even better with a large bonus sunroom, complete with additional built-ins and an entire wall of pantry storage. Whether you envision it as a casual gathering space, home office, hobby area, or simply a place to enjoy the extra room, this flexible space adds even more versatility to the home. Upstairs, new carpeting runs throughout, complemented by fresh paint in the entire home. The brand-new full bathroom features a tub/shower combination and new vanity, giving the space a crisp, updated feel. The best part? The major exterior work has already been done, the home is clean and move-in ready, and there's still plenty of opportunity to bring your own style to the interior. Priced competitively, 1013 Orchard Hill Dr offers an opportunity to enjoy a desirable Winchester setting, the freedom of no HOA, and a home where the important updates have already been taken care of. Come see it for yourself and imagine what you'll do with the rest!

1013 Orchard Hill Dr, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

116 E Cork St, Winchester
$389,000
2 Beds ⋅ 1 Baths
A RARE DOWNTOWN GEM IN THE HEART OF HISTORIC WINCHESTER! Discover the charm and convenience of this beautifully restored circa-1900 row house, ideally located just one block from Winchester’s iconic Walking Mall. Enjoy an exceptional walkable lifestyle with an array of restaurants, coffee shops, boutiques, and nightlife right outside your door. Thoughtfully renovated from top to bottom, this home combines historic character with modern comfort, featuring updated plumbing and electrical systems, beautiful hardwood flooring, and a spacious gourmet kitchen with granite countertops and convenient direct access to the rear deck—perfect for outdoor dining and entertaining. Additional highlights include a front-loading washer and dryer, ceramic tile bath, high-end window treatments, and a generous walk-in closet. The transformation continues outside, where the fully restored and freshly painted exterior has just been completed, including a newly painted metal roof, along with a freshly restained rear deck and front porch. Fresh interior paint throughout adds to the bright, polished presentation. Beautifully updated, exceptionally located, and full of character, this special downtown property is truly move-in ready and a must-see!

116 E Cork St, Winchester

Listing courtesy of Keller Williams Realty. Contact:

1 E Hart St, Winchester
$299,900
4 Beds ⋅ 3 Baths
Enjoy downtown Winchester living with plenty of flexibility! This 4-bedroom, 2.5-bath townhome offers a functional layout in a convenient location close to restaurants, shopping, schools, Handley games, and all that downtown Winchester has to offer. The main level features a comfortable living area, kitchen with eat-in space, and access to a beautiful Trex deck overlooking the fully fenced backyard. Upstairs, you'll find three bedrooms and a full bath. The finished walk-out lower level adds even more versatility with a fourth bedroom, full bath, and laundry area. Step outside to a stamped concrete patio and fenced yard with storage shed. With multiple outdoor living spaces, off-street parking, and an incredibly convenient location, this home offers plenty of possibilities inside and out.

1 E Hart St, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

5 E Hart St, Winchester
$284,900
2 Beds ⋅ 3 Baths
Enjoy the convenience of downtown Winchester living in this charming 2-bedroom, 2-bath townhome, ideally located within walking distance of restaurants, shopping, school games and more. The main level features a comfortable living area and an eat-in kitchen with doors leading to a beautiful Trex deck, perfect for morning coffee, grilling or relaxing at the end of the day. Upstairs, both bedrooms offer their own en-suite baths, with the primary bedroom also featuring a walk-in closet. The finished basement adds valuable bonus space with plenty of flexibility for a rec room, home gym, office or additional living area. From there, walk out to a beautiful stamped concrete patio and fully fenced backyard with a storage shed. With two great outdoor living spaces, a finished lower level and a location that makes it easy to enjoy everything downtown Winchester has to offer, this townhome packs a lot into a convenient footprint.

5 E Hart St, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

3 S Euclid Ave, Winchester
$305,500
3 Beds ⋅ 2 Baths
Charming 1955 home offering timeless character, inviting curb appeal, and a versatile floor plan! This 3-bedroom, 2-full-bath home features one bedroom conveniently located on the main level, along with a dedicated office that provides a great space for working from home, hobbies, or additional flex space. One of the two full bathrooms is brand new, adding a fresh modern touch to this classic home.

3 S Euclid Ave, Winchester

Listing courtesy of Main Street Realty. Contact:

621 Patterson Ave, Winchester
$357,000
4 Beds ⋅ 3 Baths
Some homes simply feel right the moment you arrive—and this charming Cape Cod in an ideal in‑town Winchester location is one of them. Offering 3–4 bedrooms and 2.5 bathrooms, the layout flows with an easy, everyday comfort. The main level features two convenient bedrooms, a bright and inviting living room, a dedicated dining area, and a renovated kitchen with new cabinets and stainless‑steel appliances. In 2021, the home received a thoughtful refresh, including new vinyl plank flooring throughout, renovated bathrooms, new light fixtures, updated receptacles/switches/covers, a new roof, and updated plumbing for added peace of mind. Upstairs, two additional rooms and a full bathroom provide flexible space—whether you envision a fourth bedroom, office, or bonus retreat. With over 2,000 sq ft of finished living space, the home also includes a finished basement with a full bath and direct walkout access to the backyard, creating an ideal setting for a second living area, guest space, or recreation zone. Outdoors, a spacious deck and fully fenced backyard with privacy fencing offer a comfortable retreat perfect for relaxed evenings, weekend grilling, and easy gatherings. All of this is just moments from downtown Winchester’s shopping, restaurants, and everyday conveniences. Schedule your tour today and experience the feeling for yourself.

621 Patterson Ave, Winchester

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

2817 Papermill Rd, Winchester
$325,000
3 Beds ⋅ 2 Baths
Welcome to 2817 Papermill Road, a beautifully maintained home that reflects true pride of ownership from the moment you arrive. Situated on an impressive approximately 0.35-acre lot, this property offers a wonderful combination of space, comfort, and convenience all while being just minutes from everything Winchester has to offer. The home has been thoughtfully cared for and kept in excellent condition, creating a warm and welcoming atmosphere that is ready for its next owner to enjoy. Outside, the spacious lot provides plenty of room to relax, entertain, garden, play, or simply enjoy having some extra breathing room without sacrificing the convenience of being in the city. One of the property's standout features is the abundance of parking available in front of the home, making it easy to accommodate multiple vehicles and guests. Whether you're hosting family and friends or simply appreciate having extra parking space, this home delivers. Location is another major highlight. Enjoy convenient access to Downtown Winchester, shopping, restaurants, schools, parks, everyday necessities, and major commuter routes, while still coming home to a property with plenty of outdoor space to call your own. With its generous lot, well-cared-for condition, ample parking, and convenient Winchester location, 2817 Papermill Road offers a combination that's increasingly hard to find. Come see what makes this home special—you may just find the space, location, and feeling of home you've been looking for.

2817 Papermill Rd, Winchester

Listing courtesy of Weichert, REALTORS. Contact:

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