Winchester Homes under $250,000

Winchester Homes under $250,000

Welcome to Winchester, Virginia—a charming city where history meets modern living! Nestled in the picturesque Shenandoah Valley, Winchester boasts a rich heritage, vibrant community, and stunning natural landscapes that make it a desirable place to call home. Known as the "Apple Capital of Virginia," this city is not only famous for its delicious fruits but also for its warm and welcoming atmosphere.

Winchester's historic downtown is a delightful blend of quaint shops, local eateries, and cultural attractions, including the renowned Museum of the Shenandoah Valley. Residents enjoy a variety of outdoor activities, with nearby parks, hiking trails, and the scenic Blue Ridge Mountains just a short drive away. The city’s strong sense of community is evident in its numerous festivals, farmers' markets, and events that bring neighbors together throughout the year.

For those seeking affordable housing options, Winchester offers an impressive selection of homes under $250,000. Whether you're a first-time homebuyer or looking to downsize, you’ll find charming single-family homes, cozy townhouses, and even some delightful fixer-uppers that are bursting with potential. With its affordable real estate market, Winchester provides a unique opportunity to invest in a home while enjoying the benefits of city living and the tranquility of the surrounding countryside.

Discover the beauty and charm of Winchester, VA, where your dream home awaits at an unbeatable price. Come explore this vibrant city and see for yourself why it is the perfect place to put down roots!

Newest Winchester Homes under $250,000

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:

136 Brookland Ct Unit 9, Winchester
$249,900
2 Beds ⋅ 2 Baths
Welcome to easy, low-maintenance living at 136-9 Brookland Court, a stunning top-level condo located in the highly desirable Parkplace Condominiums of Winchester, VA. Brimming with chic vibes, clean finishes, and an abundance of natural light, this updated home boasts a bright, spacious layout with vaulted ceilings. The sunlit living room serves as a captivating centerpiece, featuring skylights, a cozy gas fireplace, an open dining area, and direct access to a private balcony perfect for relaxing outdoors. In the kitchen, cook with style thanks to the airy architectural height and sleek stainless steel appliances. Down the hall, you'll find a bright, spacious primary bedroom that serves as a true retreat, offering a generous walk-in closet and a beautifully updated ensuite primary bath complete with a modern walk-in shower. A second large bedroom highlights charming bay windows, double closets for extra storage, and is served by another updated full bath. Enjoy the ultimate everyday convenience with an in-unit washer and dryer, off-street parking, and an unbeatable location close to schools, shopping, dining, and major commuter routes. Your monthly condo fee provides total peace of mind by covering water and sewer, along with neatly maintained common areas, professional lawn care, snow removal, and trash services. Offering the ideal combination of comfort, style, and low-maintenance convenience, this top-floor residence represents prime Winchester living at its best.

136 Brookland Ct Unit 9, Winchester

Listing courtesy of Colony Realty. Contact:

123 Averrell Ave, Winchester
$139,000
3 Beds ⋅ 3 Baths
Welcome to relaxed and comfortable living in the desirable Regency Lakes community of Winchester, where this remarkably large and expansive manufactured home stands out exceptionally from neighboring properties by offering vastly superior square footage, an extended exterior profile, and a deep, generous footprint. Step inside to discover a truly massive, open-concept living area featuring stunning floor-to-ceiling stone accent fireplaces, soaring ceilings, and abundant space for oversized furniture and grand entertaining. A chef-styled kitchen boasts an immense array of rich wooden cabinetry, a brand-new gas cooktop, an expansive center prep island, and a seamless flow into the adjoining dining room. Recent updates further elevate the home, including new carpet (installed in 2023) and new wood floors in the guest room. Combining this unmatched scale with a functional floor plan designed to maximize everyday living, a wide covered front porch, and a private storage shed on a wonderful lot, the home provides quick access to local parks, schools, commuter arteries, and historic downtown Winchester for a lifestyle far bigger than the rest. This residency pays a ground rent of $953 that includes the following community amenities: swimming pool, whirlpool/spa/hot tub, clubhouse, fitness center, tennis courts, basketball and volleyball courts, a playground, picnic areas, horseshoes, fishing, waterfront sites, RV storage, on-site management, pet-friendly spaces, and regular community activities.

123 Averrell Ave, Winchester

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

302 Doe Trl Trl Sw, Winchester
$235,000
2 Beds ⋅ 1 Baths
COME SEE THIS CUTE HOME AND MAKE IT YOURS. LOCATED IN SHAWNEE LAND, EASY DRIVE TO SHOPPING, SCHOOLS, HOSPITAL. SHAWNEE LAND HAS SEVERAL LAKES FOR EJOYMENT.HOME IS SOLD "AS IS", YOU CAN PUT YOUR TOUGHEST THOUGH OUT.

302 Doe Trl Trl Sw, Winchester

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

305 Raccoon Dr, Winchester
$169,900
1 Beds ⋅ 1 Baths
Cozy 1-bedroom, 1-bathroom cabin located on a level, nicely shaded lot, ready for your enjoyment. Offering the perfect combination of rustic character, comfort, and natural beauty. Step outside onto the screened-in porch and enjoy your morning coffee, unwind with a good book, or simply take in the sights and sounds of the surrounding woods. This peaceful setting offers a wonderful opportunity to slow down and enjoy nature while still having all the comfort you need. Whether you're searching for a weekend getaway, a cozy full-time residence, or an investment property with rental potential, this versatile cottage is full of possibilities. Newer upgrades include an electrical panel, UV light, and exterior and interior painting/siding. Won’t last long at this price point!

305 Raccoon Dr, Winchester

Listing courtesy of Dandridge Realty Group, LLC. Contact:

1125 Conway St, Winchester
$250,000
2 Beds ⋅ 1 Baths
Welcome to 1125 Conway Ave, a charming bungalow in Winchester City that's move-in ready and full of character! This cozy 2-bedroom, 1-bath home features beautiful hardwood floors and numerous recent updates, including a new roof, fresh interior paint, kitchen remodel, hallway and bathroom flooring, and a new stainless steel refrigerator. The deck has also been restored, providing a great spot to relax or entertain. Conveniently located near shopping, dining and everyday amenities, with quick access to I-81 from Winchester's east side—making it an excellent option for commuters. Whether you're a first-time buyer, downsizing, or looking for a low-maintenance home in the city, this bungalow is worth a look. Schedule your showing today!

1125 Conway St, Winchester

Listing courtesy of NextHome Realty Select. Contact:

103 E Germain St, Winchester
$245,000
2 Beds ⋅ 2 Baths
Roof replaced in 2020. NEW PRICE! Welcome to 103 E Germain St, a charming end-of-row townhouse just blocks from downtown Winchester! Enjoy easy access to restaurants, shops, breweries, entertainment, and historic attractions while enjoying low-maintenance living. The bright main level features an open floor plan, beautiful hardwood flooring, a spacious living room, kitchen, and dining area, plus a convenient half bath. Upstairs offers two generously sized bedrooms with ample closet space and a full bath. Step outside to the Trex deck and manageable backyard, perfect for relaxing or entertaining. Off-street parking for two vehicles is a rare bonus in this downtown location. Whether you're a first-time buyer, downsizer, or investor, this home offers comfort, convenience, and an excellent location with easy access to I-81 and Northern Virginia. Enjoy everything Winchester has to offer, including the vibrant Old Town district, locally owned restaurants and boutiques, breweries, cultural attractions, and historic landmarks. Schedule your private showing today! All sizes are approximate.

103 E Germain St, Winchester

Listing courtesy of RE/MAX Roots. Contact:

187 Valley Mill Rd, Winchester
$220,000
2 Beds ⋅ 1 Baths
Great investment opportunity for this centrally located rambler! Just minutes from Route 7 and I-81, this property offers convenient access to shopping, restaurants, and everyday amenities. The current tenant is under lease through 11/13/26, providing immediate rental income for an investor. With some sweat equity and a few updates, there is potential to increase the rental income significantly. Looking for a home of your own? This property could also be a great opportunity for a first-time homebuyer looking to build equity and make it their own. The home features LVP flooring throughout and a spacious, flat yard with plenty of room to enjoy the outdoors. Whether you're looking to add to your investment portfolio or find a home with room to grow, this one is worth a look!

187 Valley Mill Rd, Winchester

Listing courtesy of Samson Properties. Contact:

403 Stag Trl, Winchester
$115,000
Ever dreamed of owning your own private A-frame cabin in the woods? Whether you're searching for the perfect weekend retreat, a unique short-term rental opportunity, or a peaceful getaway to enjoy with family, friends, or clients, this charming mountain cabin is full of potential. Tucked away in a quiet, wooded setting with easy year-round access, this hidden gem offers the perfect balance of privacy and convenience. Relax on the spacious front deck surrounded by mature trees with peaceful wooded views, or unwind on the rear deck while taking in breathtaking long-range mountain views that truly feel like a million-dollar backdrop. Inside, you'll find a cozy A-frame cabin that is being sold furnished. The current owner has enjoyed it as a weekend getaway, and it's ready for the next owner to complete the vision and create their own mountain retreat. The loft provides additional sleeping space while maintaining the classic A-frame design. Located approximately 30 minutes from Historic Downtown Winchester, about 30 minutes from Front Royal, and roughly 1½ hours from Fairfax, this property is close enough for an easy weekend escape while feeling worlds away from the hustle and bustle. Residents enjoy low real estate taxes, low HOA dues, and community amenities including a scenic pond and waterfall. As more homes continue to be built throughout the community, this peaceful mountain neighborhood is quickly becoming a hidden gem with strong future potential. Property is being sold furnished and strictly As-Is.

403 Stag Trl, Winchester

Listing courtesy of Colony Realty. Contact:

135 S Kent St Unit 202, Winchester
$250,000
1 Beds ⋅ 1 Baths
Step into the charm of Historic Downtown Winchester with this beautifully renovated Urban Lofts Condominium, where history and modern living come together. Located in a home built in 1825, this unique property is just a short stroll to Winchester's favorite restaurants, boutique shopping, coffee shops, museums, and downtown events. Renovated in 2021, the condo offers stylish updates while preserving its historic character. The kitchen features quartz countertops, stainless steel appliances, a new refrigerator, and a new island with an integrated sink that creates the perfect gathering space. Fresh paint, modern lighting, a beautifully updated bathroom, and a built-in bookcase add to the home's appeal. The exposed brick fireplace serves as a striking architectural feature, adding warmth and character to the living room. (Fireplace is decorative only.) Whether you're looking for your own place in the heart of downtown or an investment opportunity, this low-maintenance condo offers the best of both worlds; historic charm, modern finishes, and an unbeatable location where you can leave the car behind and enjoy everything Winchester has to offer.

135 S Kent St Unit 202, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

136 Brookland Ct Unit 6, Winchester
$244,900
2 Beds ⋅ 2 Baths
Discover the charm of Parkplace Condominiums, where comfort meets convenience in a vibrant community. This inviting 2-bedroom, 2-bathroom unit features modern stainless steel appliances, including a built-in microwave, dishwasher, and electric oven, making meal prep a delight. Enjoy the ease of in-unit laundry with washer and dryer hookups, ensuring your daily routines are seamless. Nestled in a friendly neighborhood, residents benefit from well-maintained grounds with included lawn care, snow removal, and trash services. The community is close to local parks, perfect for leisurely strolls or weekend picnics. Excellent schools are just a stone's throw away, providing quality education options for all ages. With a strong sense of community and convenient access to public services, Parkplace is more than just a home; it's a place to create lasting memories. Experience the warmth and comfort of this lovely unit, where every detail is designed for your enjoyment.

136 Brookland Ct Unit 6, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

157 Brookland Ter Unit 6, Winchester
$239,000
2 Beds ⋅ 2 Baths
Fantastic location! This spacious second-floor condo offers more square footage than most units in the community and features an open, light-filled layout, and durable flooring throughout with NO carpet. The thoughtfully designed floor plan includes a large living room, separate dining area, two generously sized bedrooms, and two full bathrooms. The primary suite offers a private bath, a large closet, and plenty of room for a king-sized bed. The kitchen was remodeled in recent years with quality cabinets, quartz countertops, undercabinet lighting, and new appliances. A separate laundry room with a full-size washer and dryer adds everyday convenience. Step outside to the private deck overlooking the common area and mature trees, creating a peaceful outdoor retreat. An additional private storage unit, conveniently located right next to the condo, provides valuable extra space for seasonal items, bicycles, or other belongings. Condo fee covers common area maintenance, trash, water, sewer and snow removal. One assigned parking space per unit. Seller to provide a credit towards painting of $3,000.

157 Brookland Ter Unit 6, Winchester

Listing courtesy of MarketPlace REALTY. Contact:

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