Winchester Real Estate

Charming, Updated Rancher in the Heart of Winchester! Welcome home to this impeccably maintained 3-bedroom, 2-bath ranch offering the perfect blend of comfort, character, and convenience—all on one level! From the moment you arrive, you'll appreciate the pride of ownership and thoughtful updates throughout. The spacious kitchen is the heart of the home, offering abundant cabinetry and room to gather with family and friends. Multiple living areas provide the flexibility to create a cozy family room, home office, playroom, or hobby space—giving everyone room to spread out. Major updates provide peace of mind, including a new roof, siding, and side porch—all completed within the last year. Other updates include added storage, updated bathrooms, updated flooring, and lots of other touches throughout. Additional features include a gas furnace, central air conditioning, and an abundance of storage rarely found in homes of this size. Located within the City of Winchester, you'll enjoy the convenience of nearby shopping, dining, parks, and commuter routes while coming home to a property filled with warmth, charm, and timeless character. This lovingly cared-for home is a true hidden gem that's move-in ready and waiting for its next owner. Schedule your private tour today before this one is gone!

1004 Pennsylvania Ave, Winchester

Listing courtesy of Samson Properties. Contact: (540) 348-4911

$389,900

3 Beds ⋅ 3 Baths

Welcome to this lovely and charming home located in the sought-after active adult community of Winchester Landing. Thoughtfully designed to highlight elegant architecture, stylish finishes, and countless upgrades. This home blends sophistication with comfort, creating a lifestyle that feels both refined and effortlessly relaxed. Step inside to a light-filled open layout that seamlessly connects the living, dining, and kitchen areas—perfect for entertaining or relaxed daily life. Hardwood floors on main and upper levels, ceramic tile kitchen flooring. The gourmet kitchen is a true centerpiece, featuring granite countertops, designer cabinetry, added backsplash, and modern fixtures—all opening to spacious living and dining areas ideal for entertaining or everyday comfort. From the dining area, step outside to the covered patio, a peaceful retreat for al fresco dining or unwinding in the shade. The main-level primary suite offers comfort and convenience, complete with a well-appointed en suite bath and a generous walk-in closet. A conveniently located laundry room adds to the home’s easy, single-level living appeal. Upstairs, two additional bedrooms offer flexibility to suit your lifestyle—ideal for guests, a home office, or hobby space. Ideally situated for convenience and lifestyle, this home is just minutes from Old Town Winchester’s charming shops and dining, 2 miles from Winchester Country Club, 3 miles from the dog park and Shenandoah University, and offers easy access to Route 7 and I-81 for commuting or weekend escapes

126 Maury, Winchester

Listing courtesy of LPT Realty, LLC. Contact: 8773662213

$180,000

3 Beds ⋅ 1 Baths

Opportunity awaits at 309 Liberty Avenue in Winchester City. This classic Cape Cod offers the chance to create something truly special in an area experiencing continued growth, infrastructure improvements, and neighborhood investment. The property does require substantial work, making cash financing the most likely option; however, the potential is significant for a buyer with the vision to transform it into a distinctive home while building meaningful sweat equity. The level backyard provides plenty of usable outdoor space, and the rear alley creates the possibility of adding a gated entrance for convenient off-street parking behind the home. A rare opportunity to reimagine a well-located Winchester property and make it entirely your own.

309 Liberty Ave, Winchester

Listing courtesy of Keller Williams Realty. Contact: 7036690099

$1,395,000

Legacy Investment Opportunity: Prime, Turn-Key Asset in Downtown Historic District! 7500 SF over four floors, located on the celebrated Walking Mall, Winchester, VA, the fastest-growing metro area in Virginia! This historic building has been fully modernized and is 100% occupied with a strong leasing history. List Price: $1,395,000. CAP Rate: 7.5%. Annual Net Rent: $106K. The property features a strategic mix of four stabilized leases, including prime ground-floor retail and Class A office suites across the second, third, and fourth floors. This is a very rare income opportunity!

185 Loudoun St N, Winchester

Listing courtesy of Coldwell Banker Premier. Contact:

$969,000

5 Beds ⋅ 4 Baths

A rare opportunity to live on Lake Serene - Welcome to your private waterfront retreat on Lake Serene, where resort-style outdoor living meets timeless modern craftsmanship. Rarely does an opportunity like this come along. Tucked among the trees on one of Frederick County's most sought-after private lakes, this beautifully renovated waterfront home offers the perfect balance of luxury, recreation, and everyday comfort. Completely transformed in 2016 with a 2-story addition along with thoughtful updates & remodeling, the home features a stunning custom Chef's kitchen with rich cherry cabinetry, elegant soapstone countertops, and quality finishes include KitchenAid gas range and Viking range hood. Designed for gathering with family and friends we have 5 bedrooms and 3.5 beautifully remodeled bathrooms, numerous living areas on two spacious levels making this THE gathering place! Offering one level living for all daily activity the main level is host to gorgeous family room with soaring ceilings, kitchen, dining room, living room with fireplace, laundry, 3 bedrooms & 2.5 baths. The lower level offers additional space to spread out with game room, recreation room, wet bar and two additional bedrooms and storage. Step outside and discover your own private retreat. Extensive hardscaping, an oval in-ground heated pool, multiple outdoor entertaining spaces, and mature landscaping create a resort-like setting that's perfect for summer afternoons or evening sunsets with views of the lake. A detached 2-bay garage also has a finished area w/ fireplace which was originally utilized as an office now acts as a pool house. Life at Lake Serene is about more than the home itself. Enjoy boating, kayaking, fishing, paddleboarding, or simply relaxing by the water. Inventory on Lake Serene is exceptionally limited, with many properties remaining in the same families for generations. Even more uncommon is finding a home that has already been tastefully updated—allowing you to begin enjoying the lake lifestyle immediately instead of planning years of renovations. Whether you're searching for a full-time residence or the ultimate weekend escape, this exceptional waterfront property offers a rare opportunity to own one of the area's most desirable lake homes. Come experience why life is simply better at Lake Serene.

485 Lake Serene Dr, Winchester

Listing courtesy of MarketPlace REALTY. Contact:

$350,000

4 Beds ⋅ 2 Baths

Country living without the long commute! This 4-bedroom, 2-bath ranch sits on 2.15 private acres just minutes from Winchester, offering the perfect blend of peaceful surroundings and everyday convenience. Backing to woods with your own private walking paths, this property also enjoys distant mountaintop views that can be appreciated from both the backyard and the primary bedroom. Many of the major improvements have already been completed, including new windows in the original portion of the home (2025), a new water softener (2025), an updated bathroom featuring a walk-in shower and new sink vanity (2025), fresh interior paint (2025), a roof that's approximately five years old, heat pump (2018), siding (2017), and a recent septic inspection with the recommended repairs completed in July 2026 for added peace of mind. Inside, you'll find an eat-in kitchen with stainless steel appliances, a wood stove, four bedrooms, and two full bathrooms, providing comfortable one-level living with plenty of flexibility for guests, or a home office. Step outside to enjoy the spacious fully fenced yard, concrete patio, storage shed, established landscaping, including a variety of wild berries amongst the property. Whether you're exploring your own waling paths, gardening, or simply taking in the peaceful surroundings and mountaintop views, this property offers the space, privacy, and lifestyle you've been looking for. Many of the major improvements have already been completed, allowing the next owner to focus on making the home their own while enjoying the privacy, acreage, and peaceful setting from day one. Located mins from town off of Rt. 50, close to shopping, dining, and Winchester Medical Center. A short drive to the local major highways/I-81.

852 Mcdonald Rd, Winchester

Listing courtesy of NextHome Realty Select. Contact: (540) 667-9097

$369,900

2 Beds ⋅ 2 Baths

Welcome home to comfortable, low-maintenance living in the desirable 55+ community of Woodbrook Village! This well-maintained end-unit home offers the perfect blend of space, privacy, and convenience. Featuring two spacious bedrooms, two full bathrooms, and a cozy yet open floor plan, this home provides plenty of room to relax, entertain, and enjoy everyday living. The updated kitchen offers newer appliances, ample cabinetry, and easy access to the main living and dining areas. Freshly cleaned carpets make the home feel clean, comfortable, and move-in ready. The screened porch is the perfect place to enjoy your morning coffee, read a good book, or unwind while overlooking the peaceful wooded backdrop. As an end unit, the property offers an added sense of privacy. A two-car garage provides generous parking and additional storage space. The HOA makes life even easier by covering water and sewer, lawn maintenance, snow removal, trash pickup, access to the community center, and more. Location is key! Woodbrook Village is conveniently situated just minutes from shopping, dining, medical facilities, and everything Winchester has to offer. Fiber internet is also being installed throughout the neighborhood, adding even more convenience for streaming, working from home, and staying connected. Enjoy a carefree lifestyle in a welcoming community without sacrificing space, privacy, or convenience. And at a price that con not be beat! This wonderful home is ready for its next owner!

111 Tanglewood Ln, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact: (540) 665-0360

$385,000

3 Beds ⋅ 2 Baths

New construction one-level home on a spacious 1-acre lot! Currently under construction and anticipated to be completed in early October 2026, this thoughtfully designed 3-bedroom, 2-bath ranch offers the ease of single-level living with an open-concept floor plan, luxury vinyl plank flooring, granite countertops, upgraded stainless steel appliances, and an attached two-car garage. The open kitchen flows seamlessly into the dining and living areas, creating a bright, welcoming space that's ideal for everyday living and entertaining. The private primary suite, spacious secondary bedrooms, modern finishes, and abundant cabinet space combine comfort, style, and functionality throughout the home. Whether you're buying your first home, downsizing, retiring, or simply looking for the convenience of one-level living, this home offers a comfortable, low-maintenance lifestyle on a beautiful 1-acre lot with room to enjoy the outdoors. Construction is anticipated to be completed in early October 2026. Buyers may still have the opportunity to make certain finish selections, depending on the stage of construction. Contact the listing agent for current construction updates, available selections, and additional details. Taxes currently reflect the land only.

300 Panther, Winchester

Listing courtesy of Preslee Real Estate. Contact: 5402274416

$235,000

2 Beds ⋅ 2 Baths

This home includes two bedrooms, each with an attached bathroom, and is over 1,500 square feet. It features an open floor plan with cathedral ceilings, exposed beams, and hardwood floors. The front family room boasts winter mountain views. The rear sunroom is perfect for enjoying the backyard wildlife. Shawneeland offers a private community beach, lake, playgrounds, and trails. The property was built before 1978; lead-based paint may be present.

114 Inca Trl, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact: (540) 665-0360

$127,750

Rare opportunity to own three adjoining fully wooded parcels in the quiet and peaceful Shawneeland community. Numerous residential and recreational possibilities exist with ownership of these tracts. Located just a few miles west of Winchester in the Rosenberger area of the county. Access is secured via extensive road frontage on paved Wolf Spring Trail. Utilities are close by making for easy and affordable hookups. Ideal location for a mountain top retreat or family compound. Stunning year round panoramic views of the valley below and surrounding mountains. Beautiful rock formations dot the landscape of these lots and the topography ranges from mild to steep. The acreage sprawls across the eastern slope of Great North Mountain. This land is zoned (R5) Residential Recreational Community District. The intention of the Residential Recreational Community District is to provide for a carefully planned recreational community which takes advantage of unique natural features and settings. Enjoy hiking, camping, and recreation of all types on this land. Only minutes from all the amenities and entertainment Winchester has to offer. Less than an hour from Northern Virginia.

Wolf Spring Trl, Winchester

Listing courtesy of Whitetail Properties Real Estate, LLC. Contact: 2172859000

$384,900

3 Beds ⋅ 3 Baths

Welcome to 109 Nootka Way, a beautifully maintained end-unit townhome offering the perfect blend of modern style, comfort, and low-maintenance living. Built just a year and a half ago, this like-new home features 3 spacious bedrooms, 2.5 baths, and 1,509 square feet of thoughtfully designed living space. The open-concept main level is filled with natural light and provides an inviting space for both everyday living and entertaining. The well-appointed kitchen flows seamlessly into the dining and living areas, creating a functional and welcoming layout. Upstairs, you’ll find a generous primary suite with an en-suite bath, two additional bedrooms, a full hall bath, and convenient upper-level laundry. As an end unit, the home enjoys added privacy, extra windows, and abundant natural light throughout. A rear-entry one-car garage provides secure parking and additional storage. Located in a desirable Winchester community with easy access to shopping, dining, commuter routes, and everyday conveniences, this move-in-ready home offers the benefits of newer construction without the wait.

109 Nootka Way, Winchester

Listing courtesy of Samson Properties. Contact: (540) 348-4911

$635,690

3 Beds ⋅ 4 Baths

Rare Dual Primary Suites on the Main Level! Backing to trees, this stunning new Matisse at Hiatt Pointe at Snowden Bridge offers the perfect blend of comfort and flexibility for active adults 55+. Personalize your finishes and move in this spring! Enjoy a gourmet kitchen with SS appliances including hood, quartz countertops, an oversized island, and walk-in pantry. The open layout features 10' ceilings, a gas fireplace, and a screened porch overlooking the wooded homesite. The finished lower level adds a rec room, third bedroom, and full bath. Enjoy resort-style amenities including a gated entrance, clubhouse, fitness center, pickleball, bocce, pool, and hot tub. Ask about builder incentives!

3168 Ruby Royce Dr, Winchester

Listing courtesy of Brookfield Mid-Atlantic Brokerage, LLC. Contact: (703) 420-3322

Winchester Real Estate

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