Winchester Homes under $500,000

Winchester Homes under $500,000

Welcome to Winchester, Virginia – a charming city steeped in rich history and surrounded by picturesque landscapes. Nestled in the beautiful Shenandoah Valley, Winchester offers a delightful blend of small-town charm and modern amenities, making it an ideal place to call home. Known for its vibrant downtown area, residents can enjoy an array of boutique shops, local eateries, and cultural attractions, including the renowned Museum of the Shenandoah Valley and the historic Old Town district.

For those looking to settle in this enchanting city without breaking the bank, Winchester boasts an impressive selection of homes priced under $500,000. Whether you’re a first-time homebuyer, a growing family, or looking to downsize, you’ll find a variety of options that suit your needs. From cozy single-family homes with spacious backyards to charming townhouses nestled in friendly communities, Winchester offers diverse properties that cater to every lifestyle.

The city's strong sense of community is reflected in its numerous parks, recreational facilities, and family-friendly events throughout the year. With a low cost of living, excellent schools, and a welcoming atmosphere, it’s no wonder that Winchester is attracting families and professionals alike.

Explore the possibilities of homeownership in Winchester, where affordability meets quality living. With homes under $500,000, you can embrace the beautiful landscapes, rich history, and vibrant community that make this city a truly special place to live. Come discover your dream home in Winchester today!

Newest Winchester Homes under $500,000

626 Bruce St, Winchester
$399,044
3 Beds ⋅ 2 Baths
Thoughtfully renovated home in the City, (although the backyard feels more like a private oasis) This one has all the renovations! Gorgeous Kitchen complete with Custom built in buffet, Quartz countertops, pantry cabinet and all the pretty features you are dreaming of! Brand new Appliances, recessed lighting, new lighting and plumbing fixtures throughout, LVP, vanities, Workshop/storage room. Enormous family room with custom built in cabinetry and a wood stove for the chilly winter nights. (current owners have not used) This lower level features a fully renovated full bath as well (maybe you use the whole space as your PRIMARY??!!) laundry room, and space for a play room/office. The true prize is beyond the double doors to the covered patio. This backyard will steel the show! Large shed for storage, deck for entertaining, grilling OR chilling! To the left of the home is an expansive field called Friendship Park (owned by the Friendship fire hall) This is what gives this home the feeling of privacy that's hard to find in the city.

626 Bruce St, Winchester

Listing courtesy of Roberts Realty Group, LLC. Contact:

161 Brookland Ct Unit 6, Winchester
$244,900
2 Beds ⋅ 2 Baths
Come see this top-level condo in Parkplace! This unit features a light-filled living room with cathedral ceilings, two skylights, newly installed LED wafer lighting, and a cozy gas fireplace perfect for chilly winter nights. The primary bedroom includes a walk-in closet and a private bathroom with a walk-in shower. The spacious guest bedroom boasts a beautiful bay window that lets in abundant natural light. Enjoy spring and summer days relaxing on your private deck. The unit offers newly installed luxury vinyl plank flooring throughout, plus a large storage closet located right outside your door. Conveniently located near I-81, dining, and shopping—making it ideal for commuters!

161 Brookland Ct Unit 6, Winchester

Listing courtesy of Colony Realty. Contact:

709 Ross St, Winchester
$394,900
3 Beds ⋅ 3 Baths
Pretty as a Picture. Designed for Peace of Mind. With its gorgeous sage-green siding, welcoming paver walkway, and thoughtfully landscaped exterior, this beautiful new-construction home makes a wonderful first impression. Step inside to an open living and dining area that feels connected and inviting, complemented by a kitchen with granite countertops and the everyday convenience of a main-level powder room, laundry, and attached one-car garage. The Kitchen is very spacious with lots of prep space and is highlighed with Brand New stainless appliances and handy breakfast bar area. Served by a large dining area, this space is light and bright with sunny windows and contemporary lighting. Upstairs, you'll find three comfortable bedrooms, including a Private Primary bedroom with it's own private bath and 2 large closets, along with a second full hall bath. Outside, the level backyard offers room to relax, garden, entertain, or simply enjoy a little fresh air. And the front porch is inviting you for a morning cup of coffee to take in the sights of this lovely neighborhood. Located in Frederick County but throw a rock and it will land in Winchester giving you the benefit of convenience with Fred Co taxes. Minutes from Jim Barnett Park, Restaurants, Winchester's Old Town Mall, commuter routes, Winchester Medical Center, and shopping...this affordable New Construction has it all. From its charming curb appeal to its practical layout, this home offers the fresh start of new construction, modern comfort, and the peace of mind that comes with a Brand New Home. Come see how beautiful a fresh start can be at 709 Ross Street.

709 Ross St, Winchester

Listing courtesy of MarketPlace REALTY. Contact:

318 Stonehenge Rd, Winchester
$399,900
3 Beds ⋅ 2 Baths
Looking for a ranch-style home with plenty of potential and NO HOA? Offered for the first time by its original owner, this home offers convenient main-level living plus a finished bonus room above the garage, accessed by interior stairs located just off the kitchen. This additional finished space offers plenty of flexibility for a home office, hobby room, playroom, or whatever best fits your needs. Inside, you’ll find hardwood flooring in the foyer and living room, along with a gas fireplace that adds warmth and character to the main living space. The spacious primary suite features a walk-in closet, jetted tub, and an upgraded tiled walk-in shower with a built-in seat. A ramp at the front entrance provides easier access into the home. Outside, enjoy a nice, level yard along with an attached 2-car garage. The most recent updates that have already been completed are the HVAC system replaced in 2019 and a roof that was replaced approximately 6-7 years old. This home is being sold AS-IS and has been priced with its current condition in mind. While it could benefit from cosmetic updates such as fresh paint, new carpet, and some updating in the kitchen, the home can be enjoyed as it is today, allowing the next owner to make improvements and updates over time. It’s a great opportunity to move in, settle in, and make the home your own at your own pace. Convenient Winchester location close to restaurants, shopping and highways.

318 Stonehenge Rd, Winchester

Listing courtesy of NextHome Realty Select. Contact:

411 Mosby St, Winchester
$439,900
3 Beds ⋅ 1 Baths
Welcome home to this charming all-brick rancher, offering timeless appeal, beautiful hardwood floors throughout, and wonderful potential to make it your own! The inviting living room features a wood-burning fireplace, while the dining area provides a comfortable space for everyday meals and entertaining. The updated kitchen boasts granite countertops, and the remodeled bathroom adds a fresh, modern touch. Enjoy relaxing in the sun porch or entertaining outdoors on the stamped concrete patio, surrounded by gorgeous mature trees in the backyard. Replacement windows and architectural shingles, approximately nine years old, provide additional peace of mind. The walk-up attic offers exciting possibilities for additional living space, while the unfinished basement features a rough-in for a future bathroom and the opportunity to expand your finished living area. With three bedrooms, classic brick construction, and room to grow, this home is full of possibilities. Don't miss the opportunity to make it yours!

411 Mosby St, Winchester

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

317 S Kent St, Winchester
$399,000
4 Beds ⋅ 2 Baths
Welcome to this charming brick home located in the heart of Winchester! Filled with historic character, this home features beautiful hardwood floors throughout, spacious living areas, and oversized bedrooms. Enjoy relaxing on the covered front porch or entertaining on the covered back porch overlooking the large backyard. The home's timeless charm and generous room sizes offer a wonderful opportunity to make it your own. Location is a highlight! Situated right next to Ruth Jackson Memorial Park, within walking distance of Patsy Cline Memorial Park, and directly across the street from the Green Circle Trail, you'll have easy access to walking, biking, and outdoor recreation. Plus, you're just a short stroll from local shops, restaurants, Shenandoah University, and all that downtown Winchester has to offer. Historic charm, spacious living, and a fantastic location make this home a wonderful opportunity!

317 S Kent St, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

1591 Woodstock Ln, Winchester
$215,000
2 Beds ⋅ 1 Baths
“Woodstock Homestead” - This 1930’s colonial home features 1,400 sq ft, 2-bedrooms, 1-bathroom with a 1-car detached garage and sits approximately 2 miles from Old Town Winchester. The main level includes a living room with an oversized window for natural light, alongside a screened-in back porch. Below, a partially finished basement provides extra space for an office, storage or a workshop. This home retains its original historic footprint but needs extensive repairs and updates. It is being sold "as is," making it a rehab opportunity for an investor or a buyer looking for a significant sweat-equity project. The standout feature of the property is the flat .60-acre lot, providing an exceptionally large and functional backyard for this location. Situated with easy access to Interstate 81, the property combines major commuter convenience with close proximity to local dining and shopping downtown. Come see how much potential this unique property has to offer—schedule your appointment today!

1591 Woodstock Ln, Winchester

Listing courtesy of Real Broker LLC- Winchester. Contact:

115 Ware Pl, Winchester
$399,900
3 Beds ⋅ 2 Baths
Beautifully updated and ready for its next owner! This three-bedroom, two-bath home on Winchester’s desirable east side features fresh paint throughout, new luxury vinyl flooring, and new carpet. The refreshed kitchen shines with new quartz countertops and stainless steel appliances, while new light fixtures add a stylish finishing touch. Both bathrooms have been completely renovated, bringing a fresh, modern feel to the home. The unfinished lower level offers ample room for storage, hobbies, or future expansion. Enjoy outdoor living on the deck and make the backyard your own retreat. Conveniently located near shopping, dining, Route 7, and I-81, this home combines thoughtful updates with everyday convenience. Schedule your showing today!

115 Ware Pl, Winchester

Listing courtesy of Compass West Realty, LLC. Contact:

133 Blackfeet Trl, Winchester
$249,000
2 Beds ⋅ 1 Baths
If you've been dreaming of a peaceful mountain retreat without sacrificing convenience, this is the one! Tucked away on approximately 1.94 wooded acres in the Shawneeland community, this absolutely stunning and beautifully updated Lindal Cedar Chalet offers the perfect combination of rustic charm, modern updates, and privacy, all just 25 minutes from Winchester! Originally constructed in the late 1960s, this home is truly something special. Step inside and immediately fall in love with the warmth and character of the exposed cedar walls, gorgeous wood floors, soaring vaulted ceilings, and impressive fireplace that serves as the heart of the home. The open floor plan, updated kitchen, and expansive newer windows bring the outdoors in, filling the home with natural light and breathtaking wooded views. There's plenty of room to relax and unwind. Upstairs, two charming bedrooms nestled beneath vaulted ceilings offer picturesque treetop views, making you feel as though you're living in your very own treehouse! Outside, enjoy morning coffee on the front deck, unwind on the screened rear porch, or simply take in the beauty and peaceful surroundings of your private wooded setting. Situated at the end of a quiet, no-through street, this property offers a wonderful sense of seclusion. As an added bonus, the Shawneeland community offers access to an approximately 18-acre lake with a beach, opportunities for fishing, swimming, and canoeing, and a community playground. And when you're ready to venture out, you're just a short drive from shopping, dining, wineries, breweries, and the charm of Old Town Winchester! Whether you're searching for a full-time residence, weekend getaway, or your own private escape from the everyday hustle, this extraordinary chalet offers a lifestyle that's hard to find, especially at this price point!

133 Blackfeet Trl, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

3894 Northwestern Pike, Winchester
$399,900
3 Beds ⋅ 1 Baths
A rare opportunity to own 16.5 wooded acres just minutes from Winchester! Tucked away in a peaceful, private setting, this warm and inviting farmhouse has been cherished by the same family since it was built and is ready for its next chapter. Whether you're dreaming of a quiet country retreat, a place to enjoy nature and wildlife, recreational or hunting opportunities, or simply room to spread out, this property offers the space and freedom to make it your own. With 16.5 unrestricted acres, there may even be potential for an additional homesite or future subdivision, subject to verification and approval by Frederick County. The farmhouse offers timeless character and the welcoming feel of a home filled with generations of memories. Notable improvements include roof updates approximately five years ago, a well pump and water heater replaced around 2023, and a new oil furnace installed in 2025. THE LAND IS THE STAR HERE! Enjoy wooded acreage, natural beauty, privacy, and the convenience of being just a short drive from shopping, dining, and everything Winchester has to offer. Properties offering this much unrestricted acreage in such a convenient location don't come along every day. Bring your vision and discover the possibilities!

3894 Northwestern Pike, Winchester

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

182 Front Dr, Winchester
$429,900
3 Beds ⋅ 2 Baths
Come check out this Lovely Brick Rancher in an older, established neighborhood close to shopping and commuting. The home is in great condition, recently painted, with new laminated flooring and brand-new appliances. All-brick home that has been meticulously taken care of. Three bedrooms with two baths, including a full, partially finished basement. Huge rec room perfect for a Theater room or man cave. The living room includes a gas fireplace, gas tank would need to be installed. Off the kitchen is a large family room for entertaining. Would also make a perfect sitting room and dining room. The basement has a really nice Rec Room and was remodeled in 2016. A nice flat lot (almost a half acre) with a deck for enjoying the beautiful fall evenings. There is one car garage and a good-size driveway. Roof was put on in 2019 and HVAC was 2016. New Hot water heater in 2024. New Washer and dryer in 2023. In 2026 the basement was waterproofed and a new well pump was installed. Home has both city and a well but the sellers did not use the well. Septic is connected to the city. On the HVAC system when it's 25 degrees out, the oil furnace will automatically cut on. There is a main-level laundry. Washer and Dryer is set up in the Basement but could be moved. All that's left is to move in.

182 Front Dr, Winchester

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

1 Swansong Pl Unit TEAGAN 24-F2, Winchester
$399,990
3 Beds ⋅ 4 Baths
New personalized TOWNHOMES by Van Metre Homes at SNOWDEN BRIDGE in Stephenson, VA that will be ready for move in MID 2027 based on build time. Discover the Teagan 24-F2—a two-car, front-load garage townhome with three bedrooms, two full bathrooms, and two half bathrooms. Thoughtfully designed, this townhome makes every day extraordinary—from the lower-level walkout rec room, perfect for relaxation or entertainment to the heart-of-the-home kitchen with a walk-in pantry and a cozy reading nook. The primary suite features an oversized walk-in closet for added comfort and organization, making this home a perfect blend of space and convenience. The Teagan 24-F2 offers build-to-order opportunities on select homesites, allowing you to personalize your new home. Explore a variety of professionally curated interior design packages at different price points to match your style and budget. Certain homesites also offer optional structural enhancements. Contact a Van Metre New Home Advisor to learn how you can bring your vision to life! Being a new build, your home is constructed to the highest energy efficiency standards, comes with a post-settlement warranty, and has never been lived in before! Take advantage of closing cost assistance by choosing Intercoastal Mortgage and Walker Title. Self-schedule a tour today by visiting our website! ----NterNow self-touring is available on select homesites at Snowden Bridge, no agent or appointment required. Buyers may visit independently during daylight hours. For access instructions and availability, contact a Van Metre New Home Advisor directly or visit our website. ------Experience life at Snowden Bridge, a premier master-planned community minutes from Downtown Winchester, where stunning Shenandoah Valley views and endless possibilities await. This vibrant neighborhood offers unparalleled amenities for every lifestyle, from a 15,000-square-foot indoor sportsplex to refreshing swimming pools, playgrounds, scenic paved trails, and more. Families enjoy the convenience of an onsite daycare center and elementary school, while a dog park and picnic pavilion add to the charm. Perfectly situated near major commuter routes like Route 7, I-81, and I-66, Snowden Bridge keeps you effortlessly connected to Northern Virginia. Here, modern conveniences meet a warm, welcoming community, making it the perfect place to call home. -----*Other homes sites and delivery dates may be available. Pricing, offers, and availability are subject to change without notice. Images, renderings, and site plans are for illustrative purposes only and may not reflect actual homes or features. Some renderings may depict a similar home. Additional Terms and Conditions may apply. Please see a Van Metre New Home Advisor for details.

1 Swansong Pl Unit TEAGAN 24-F2, Winchester

Listing courtesy of Pearson Smith Realty, LLC. Contact:

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