Winchester Homes under $400,000

Winchester Homes under $400,000

Welcome to Winchester, Virginia, a charming city nestled in the picturesque Shenandoah Valley. Known for its rich history and vibrant community, Winchester offers a delightful blend of small-town charm and modern conveniences. From its historic downtown, where cobblestone streets are lined with quaint shops and delightful eateries, to the stunning natural landscapes surrounding the city, Winchester is a place that truly feels like home.

One of the standout features of Winchester is its affordability in the housing market. If you’re searching for a home under $400,000, you’ll be pleased to discover a variety of options that cater to diverse tastes and lifestyles. Whether you’re a first-time homebuyer, a growing family, or looking to downsize, Winchester has something for everyone. You can find charming bungalows, spacious townhomes, and even modern single-family houses, all at budget-friendly prices.

Living in Winchester means you’ll enjoy a wealth of amenities, including excellent schools, beautiful parks, and a thriving arts scene. Outdoor enthusiasts will appreciate the nearby hiking trails, scenic parks, and the stunning views of the Blue Ridge Mountains. Plus, with easy access to major highways, commuting to nearby cities is a breeze.

In Winchester, you’re not just buying a house; you’re investing in a lifestyle. With its welcoming community, rich history, and affordable housing options, Winchester is a wonderful place to call home. Explore your possibilities today and discover the charm of living in this beautiful Virginia city!

Newest Winchester Homes under $400,000

Homesite 111 Shuoner Court, Winchester
$369,990
3 Beds ⋅ 3 Baths
🏡 110 SHUONER Ct – Model Home | We Have MOVE IN READY 2026 Delivery Available St. Paul TBB | 3 BR | 2.5 BA | 1-Car Garage | Finished Lower Level 🔥 Beautiful wooded homesites available! Offering up to 2,000 sq. ft. of modern, open-concept living — customize your home the way you like ✨ Home Highlights 🍽 Open-concept main level – perfect for entertaining 🪨 Granite countertops 🧰 Stainless steel appliances 🪵 Luxury vinyl plank flooring 🛌 Upper Level Retreat 🚿 Deluxe Silver primary bath with rain shower 👕 Spacious walk-in closet 🧺 Bedroom-level laundry 🛏 Two additional bedrooms + full bath 🎬 Finished Lower Level 🛏 4th bedroom 💼 Ideal for guests, home office, gym, or media room 🌟 Additional Features 🌳 Townhome landscaping package 🔌 Deako smart light switches (smart home features) 🏦 Special financing programs available 💰 Builder incentives available with preferred lender 📅 MOVE IN READY 2026 Delivery Available 📲 Contact listing agent for pricing & current incentives 📸 Photos are representative

Homesite 111 Shuoner Court, Winchester

Listing courtesy of New Home Star Virginia, LLC. Contact:

Lot 5 Shuoner, Winchester
$374,990
3 Beds ⋅ 3 Baths
🏡 Your New Home Is Move-In Ready! Discover the St. Paul Townhome, featuring 3 bedrooms, 2.5 bathrooms, a 1-car garage, and a finished lower level—with up to 2,000 sq. ft. of space to make your own. 🌳 Beautiful wooded homesites available! ✨ Room to Gather Enjoy an open-concept main level with granite countertops, stainless steel appliances, and luxury vinyl plank flooring throughout. Whether you’re hosting friends or enjoying a quiet evening at home, this space brings everyone together. 🛌 A Place to Unwind Your primary suite features a spacious walk-in closet and a Deluxe Silver bath with a rain shower. Two additional bedrooms, a full bath, and bedroom-level laundry keep everyday living convenient. 🎬 Space That Fits Your Life The finished lower-level recreation room is ready for your home office, gym, movie nights, or playroom. 🏡 Thoughtful Details Throughout • Beautiful 12" x 24" tile in all full bathrooms and the laundry room • Deako smart light switches and smart home features • Professionally designed landscaping • Energy-efficient construction and modern finishes 💰 Special financing programs and builder incentives available with the preferred lender. 🔑 Ready to make your move? Schedule a tour and see it for yourself! 📲 Contact Jimmy Thomas for current pricing, available homesites, and incentive details. 📸 Photos are representative and may show optional features.

Lot 5 Shuoner, Winchester

Listing courtesy of New Home Star Virginia, LLC. Contact:

611 Fawn Dr, Winchester
$289,900
2 Beds ⋅ 1 Baths
Welcome to this beautifully updated 2-bedroom, 1-bath cottage, perfectly tucked away on two picturesque, serene lots surrounded by mature trees. Offering the perfect blend of charm, privacy, and possibility, this inviting home has been thoughtfully rebuilt and improved over the years and is truly move-in ready. Step inside to find beautiful wood flooring, soaring ceilings in the bedrooms, an updated kitchen, and a cozy fireplace that adds warmth and character. Major improvements, including new siding and a new A/C unit, provide added comfort and peace of mind. Outside, the fully fenced yard creates your own private retreat with plenty of space for pets, gardening, entertaining, or simply enjoying the peaceful surroundings. Relax with your morning coffee on the porch, unwind beneath the trees, and take advantage of the expansive shed for additional storage, hobbies, or outdoor equipment. Situated on two lots with very limited restrictions, the property also offers exciting possibilities for future expansion. Whether you're looking for a peaceful full-time residence, weekend retreat, or a home with room to make your own, this charming cottage is a rare opportunity to enjoy privacy, tranquility, and flexibility all in one beautiful setting.

611 Fawn Dr, Winchester

Listing courtesy of Keller Williams Realty. Contact:

207 Duwamish Trl, Winchester
$349,900
3 Beds ⋅ 3 Baths
STOP RENTING, DITCH THE TOWNHOME PURCHASE & AVOID THE RESALE HOMES! Why pay more to rent? Skip the expensive renovation headaches of resales. Lock in your budget for future years vs. possible unexpected costs like roof replacement, HVAC update or appliance replacements. Why buy a townhome with shared walls when you can own a BRAND-NEW, fully detached single-family home with a yard for the same/lower monthly payment? This pristine, never-lived-in home is completed. Here, you get a new home with pristine structural warranty, brand-new HVAC, a new roof, and total budget certainty for years to come. Nestled in Winchester with an easy commute to NoVA. Home highlights level yard, backs to large wooded common area that no additional homes to be built upon for privacy, walk out basement with ruff in future full bath, windows and slider, public water and cable at street. Kitchen island to be white. Granite in kitchen to be installed.

207 Duwamish Trl, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

116 Cloverdale Ct, Winchester
$395,000
3 Beds ⋅ 3 Baths
***Closing Cost Assistance and Concessions Will Be Considered by Sellers & Concessions of $5000 Offered***Three Level Family Colonial Style Home is Located in the Brentwood Terrace Subdivision w/ Close Access to Route 7 & Route 81 Just Off Greenwood Drive & Valley Mill Rd is Situated on a Beautifully Manicured Private Cul-De-Sac Lot, Front Porch & Deck, Fenced-In Back Yard, & Newly Paved Driveway! 3 Upper-Level Bedrooms & 2 Full Bathrooms. Recent Renovation Updates Include 2 Separate Brand New Upgraded Dual HVAC Systems (2026), New Roof & Windows (2019), Custom Kitchen Cabinetry & Energy Star Appliances, Granite Counter Tops, LVP Flooring, Recessed Lighting, & Updated Half-Bath. Fully Finished Walk-Out Lower-Level Recreation Room w/ Additional Office Space Area & Multi-Purpose Room! Close Proximity to Major Commuter Routes, Schools & Shopping Centers this Home is Turn-Key Move-in Ready!!! Seller Documents/Disclosures Attached.

116 Cloverdale Ct, Winchester

Listing courtesy of RE/MAX Executives. Contact:

606 Elk Trl, Winchester
$289,000
2 Beds ⋅ 2 Baths
PRICED TO SELL! Welcome to 606 Elk Trail in Winchester, where peaceful living meets the beauty of nature. Set in a private, serene setting, this home offers beautiful views, a fenced-in yard, and a spacious double-decker deck that creates the perfect place to relax or entertain while enjoying the surrounding landscape. Inside, the home’s character shines through with large rooms, generous closets, and a charming bay window that brings in plenty of natural light. A major renovation throughout the house includes an upgraded kitchen with stainless steel appliances, updated bathrooms, an updated laundry room, a newly paved driveway, newer water treatment system, extensive exterior landscaping, and repairs to the deck. The home also features dual-zone HVAC, and the septic system was pumped within the last year. All remaining furniture conveys, including a Murphy bed that provides the flexibility to use the space as a third sleeping area when needed. Located in Wilde Acres, residents can enjoy access to a private community lake for swimming and fishing, along with a playground, picnic pavilion, basketball and volleyball courts, and recreational trails. Surrounded by nature yet offering plenty of privacy and comfortable living space, 606 Elk Trail is a unique opportunity to enjoy a home with character, thoughtful improvements, and access to a community built for enjoying the outdoors.

606 Elk Trl, Winchester

Listing courtesy of Keller Williams Realty/Lee Beaver & Assoc.. Contact:

508 Emily Ln, Winchester
$300,000
3 Beds ⋅ 3 Baths
Cozy, updated, and close to everything! Welcome to 508 Emily Lane, a move-in-ready townhome offering comfortable living in an established Winchester community. New windows, siding, and a back door add fresh appeal to this inviting three-bedroom home with two full baths and a convenient half bath. The spacious eat-in kitchen features an island and room to gather over meals, while the cozy living room is the perfect spot to unwind. Upstairs, the primary bedroom offers its own full bath, with two additional bedrooms providing space for guests, a home office, or your everyday needs. A fenced backyard extends your living space outdoors for morning coffee, gardening, or relaxing at the end of the day. Enjoy easy access to Old Town Winchester, shopping, restaurants, schools, and urgent care, with I-81 and Route 7 just minutes away. Thoughtful updates, welcoming spaces, and a convenient location make this home one to see. Schedule your showing today!

508 Emily Ln, Winchester

Listing courtesy of Pearson Smith Realty, LLC. Contact:

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:

307 Mountain Falls Blvd, Winchester
$339,900
3 Beds ⋅ 2 Baths
Welcome to 307 Mountain Falls Boulevard—where comfortable one-level living meets a peaceful country setting! Situated on just over an acre, this well-maintained 3-bedroom, 2-bath rancher is freshly painted, move-in ready, and waiting for its new owners. Step inside to an easy, functional floor plan with everything you need conveniently located on one level. The home offers a spacious living area, comfortable bedrooms, and an attached two-car garage with a brand-new garage doors. Outside, there’s plenty of room to spread out, garden, entertain, or simply enjoy the privacy and natural surroundings. A picturesque creek runs through the property, adding a little extra charm to the setting. Located near the front of Wilde Acres/Mountain Falls, you can enjoy a more relaxed setting while still being within a reasonable drive of Winchester for shopping, dining, medical facilities, and everyday conveniences. Even better, some of the big-ticket maintenance items have already been taken care of—the home has been freshly painted, the septic inspection and pumping are complete, new walkways installed, porches painted and more. If you’ve been looking for one-level living in a country setting, this could be the one!

307 Mountain Falls Blvd, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. 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:

316 Crow Dr, Winchester
$240,000
2 Beds ⋅ 1 Baths
Lovely home offering flexible living space, wooded surroundings, and more room to make everyday life your own. Set within the Wilde Acres/Mountain Falls community, this Winchester property features a split-foyer layout with distinct living areas and a full basement, providing added flexibility for relaxing, entertaining, hobbies, working from home, storage, and more. Beyond the home, enjoy outdoor recreation within the community, spend a day exploring the Shenandoah Valley, or head into historic Old Town Winchester for restaurants, shops, events, and the pedestrian mall. Jim Barnett Park, Apple Blossom Mall, and additional shopping and services provide even more options for recreation and everyday needs. When plans take you farther, I-81, I-66, Route 50, Route 7, and Route 522 provide connections toward Northern Virginia, Front Royal, and destinations throughout the Shenandoah Valley. With adaptable space at home, wooded surroundings, outdoor opportunities, and Winchester conveniences within reach, this property gives you more ways to enjoy where you live. Photos may be virtually staged

316 Crow Dr, Winchester

Listing courtesy of Keller Williams Realty. Contact:

121 Duwamish Trl, Winchester
$329,900
3 Beds ⋅ 2 Baths
Renovatin construction being finished. Beautiful ceramic tile in family room and kitchen. Gleaming hardwoods in living room. One secondary bedroom with new carpet. Two fireplaces. Freshly planted grass. Beautiful view of big front yard thru huge bay window. Newer roof.

121 Duwamish Trl, Winchester

Listing courtesy of CENTURY 21 New Millennium. Contact:

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