Winchester Homes under $250,000

Winchester Homes under $250,000

Welcome to Winchester, Virginia, a charming city that perfectly blends rich history with modern living. Nestled in the picturesque Shenandoah Valley, Winchester is known for its stunning landscapes, vibrant arts scene, and a welcoming community that makes it an ideal place to call home. With its historic downtown area, featuring beautifully preserved buildings and a variety of shops and restaurants, Winchester offers a unique blend of small-town charm and urban convenience.

For those seeking affordable housing options, Winchester has a delightful selection of homes priced under $250,000. This makes it an attractive choice for first-time homebuyers, families, and anyone looking to invest in a thriving community without breaking the bank. These homes often come with character and charm, whether you’re interested in a cozy single-family residence or a quaint townhouse.

Living in Winchester means you can enjoy the beauty of nature with easy access to outdoor activities, including hiking, biking, and exploring nearby parks. The city is also rich in cultural experiences, with events like the Shenandoah Apple Blossom Festival and various farmers' markets that bring the community together.

With a strong sense of community, excellent schools, and a variety of amenities, Winchester is a place where you can truly thrive. Explore the homes available under $250,000 and discover the perfect blend of affordability and quality living in this historic Virginia city. Your dream home awaits in Winchester!

Newest Winchester Homes under $250,000

1785 Berryville Pike, Winchester
$199,000
2 Beds ⋅ 1 Baths
This property is zoned RP. It is either a fix me upper or tear down. Located directly on Rt. 7

1785 Berryville Pike, Winchester

Listing courtesy of Link Realty Services LLC. Contact:

23 E Germain St, Winchester
$190,000
3 Beds ⋅ 2 Baths
Welcome to this 3-bedroom, 2-bath home in Winchester, VA! Offering plenty of potential, this property could be an excellent opportunity for a first-time homebuyer or investor. The property also features a shed and workshop, providing additional storage and space for hobbies or projects. The home is being sold AS IS, WHERE IS. Buyers are responsible for performing their own due diligence regarding the property's condition, square footage, lot boundaries, zoning, permits, utilities, and any other matters of importance to the buyer. Bring your vision and explore the possibilities this property has to offer!

23 E Germain St, Winchester

Listing courtesy of Exit Success Realty. Contact:

102 Chamberlain Ct, Winchester
$142,240
3 Beds ⋅ 2 Baths
Welcome to Regency Lakes, an engaging and lively community for residents of all ages, where your dream home awaits. Always wanted Lakefront Property sit on your deck and watch the pristine Lake in this resort community. AT a price unimagined.unbelieveable $142,240. Presenting a beautifully maintained 2016 model featuring three bedrooms and two bathrooms, this home offers an impressive 1,248 square feet of thoughtfully designed living space. Upon entering, you will find a spacious open-concept eat-in kitchen enhanced by beautiful cabinetry and a new refrigerator, perfect for both everyday living and entertaining. The generously sized primary suite serves as a tranquil retreat, complete with a large walk-in shower and ample closet space. Additional bedrooms offer flexibility for visitors, a home office, or a growing family. Outside, revel in the expansive backyard, new storage shed, and full front porch ideal for sipping your morning coffee, complemented by a newly installed concrete driveway. Residents of Regency Lakes enjoy access to an array of premium amenities, including a resort-style pool, fitness center, clubhouse, walking trails, playgrounds, tennis courts, basketball courts, volleyball courts, soccer fields, and three beautiful lakes perfect for fishing. Conveniently positioned near schools, shopping, dining, major highways, and parks, everything you need is just minutes away. Whether you seek relaxation or recreation, this community offers it all. Inquire about financing options and call today to schedule a tour

102 Chamberlain Ct, Winchester

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

23 Jigsaw Pl, Winchester
$229,000
2 Beds ⋅ 2 Baths
Affordable homeowership opportunity in city limits. This town home has been cared for by owner for 35 years. Just needs some TLC to make it your own style. Living & dining with hardwood flooring. Bright kitchen with pantry and all appliances to convey. Plenty of storage with coat closet, 2 utility closets & hall closet. Laundry with shelving and space for freezer or more cabinety. Both bedroooms have double wide closets with double doors. 2 Liquid solar walls are an 80's system of plastic wall panels with internal liquid heated by sun to heat room. Owner has maintained regular servicing for gas heat & central AC. Private back yard with fencing . Not a thoroughfare street. Located convenient to dining, schools, retail, parks & rec, Green Circle Trail, just minutes to Shenandoah Universiry, the medical center, Apple Blossom Mall & Downtown Loudoun Street Walking Mall & commute routes 7, 81 and 37. Call today for a private tour

23 Jigsaw Pl, Winchester

Listing courtesy of Coldwell Banker Elite. Contact:

329 Fairview Ave, Winchester
$247,000
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:

136 Brookland Ct Unit 9, Winchester
$249,900
2 Beds ⋅ 2 Baths
One of the best units in the area! This stunning top-level condo located is the epitome of turnkey. 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:

107 Little River Dr, Winchester
$250,000
2 Beds ⋅ 1 Baths
Affordable Winchester Townhome with Investment Potential! Welcome to 107 Little River Dr, a conveniently located 2-bedroom, 1-bath townhome offering an excellent opportunity for a first-time buyer, downsizer, or investor. This two-level home provides approximately 900+ square feet of living space with a practical layout and plenty of potential to make it your own. Located in the Brookland Heights community, the property offers easy access to Winchester-area shopping, dining, employment centers, and major commuter routes. The low-maintenance townhome lifestyle makes this an attractive option for buyers looking for affordability and convenience. Whether you're searching for a primary residence, rental property, or value-add investment, 107 Little River Dr is worth a look. Bring your vision and unlock the potential of this Winchester opportunity!

107 Little River Dr, Winchester

Listing courtesy of EXP Realty, 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
$240,000
2 Beds ⋅ 2 Baths
Roof replaced in 2020. Water heater: 2026. 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. Sold "AS IS" - inspection for informational purposes. Prior inspection findings available upon request.

103 E Germain St, Winchester

Listing courtesy of RE/MAX Roots. Contact:

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