Refine Search
Sort by
219 Taggart Dr, Winchester
$905,264
4 Beds ⋅ 3 Baths
Main Level Living in Raven Pointe on one of 9 lots left! The ever-popular Tracey model with a side load 3-car garage. Home features a flexible floorpan that allows for maximum customization. Home features include large, open kitchen, vaulted ceilings in the living room (12'+), an adjacent sunroom, covered porch with Trex decking, tile showers in all baths and much more. This is a customizable plan and build. Buyers can choose any tile, appliances, cabinets, lighting they like. Basement is large with many finishing options available. Raven Pointe features very low HOA fees ($80 annually) and close proximity to Winchester, the Winchester Country Club and shopping areas (Costco a mile away). Currently, there are homes to walk and tour (already sold). Come see the difference from a custom builder.

219 Taggart Dr, Winchester

Listing courtesy of Merrifield Realty, LLC. Contact:

Selling Office: Unrepresented Buyer Office.

243 Summerfield Dr, Winchester
$835,000
5 Beds ⋅ 5 Baths
Immaculate custom home sitting on a half-acre lot in desirable Raven Pointe! Beautiful hardwood floors flow throughout the main level, leading into a dramatic family room with 20-foot ceilings, custom built-ins, a gas fireplace, and high windows featuring remote-controlled custom shades. The gourmet kitchen boasts granite countertops, soft-close cabinets, stainless steel appliances, double wall ovens, a gas cooktop, and opens seamlessly to a second living area with a warm gas fireplace. Main-level primary suite offers tray ceilings, a custom walk-in closets one with a built-in makeup vanity, and a bathroom with dual vanities and a large walk-in shower. Upstairs, you will find two additional spacious bedrooms, a full bath, plus a private in-law suite with its own en-suite bathroom. The bright walk-out lower level features a spacious rec room, full bathroom, bedroom, and a dedicated office space with a window that can also serve as a versatile bonus room. Enjoy outdoor living from the expansive composite deck or relax on the lower covered patio with ceiling fans giving an outdoor living room feel overlooking a private yard supported by an underground irrigation system. Complete with an oversized 3-car garage and located just minutes from I-81, shopping, and downtown Winchester!

243 Summerfield Dr, Winchester

Listing courtesy of Colony Realty. Contact:

Selling Office: Century 21 Redwood Realty.

103 Derrynan, Winchester
$740,000
4 Beds ⋅ 3 Baths
Welcome to 103 Derrynan Ct! Located in the highly sought-after and walkable Raven Pointe neighborhood, this exceptional 4-bedroom, 3-bath home offers the perfect blend of luxury, quality, and location—set on a premium oversized cul-de-sac lot with a fenced-in backyard, just minutes from historic Old Town Winchester, local shops, restaurants, and commuter routes including I-81, Route 7, and US-50. With over $100K in high-end upgrades, this home is built for comfort, efficiency, and timeless style. Soaring 9-foot ceilings, elegant trim work, and a stunning coffered ceiling in the primary suite elevate the interior with refined craftsmanship. Enjoy the efficiency of whole-house spray foam insulation, gleaming hardwood floors, a high-efficiency forced-air stone fireplace, and a central vacuum system with Hide-A-Hose. The chef’s kitchen opens seamlessly to the living and dining areas, while the spacious screened-in porch and irrigated yard invite effortless indoor-outdoor living. The fully insulated, EV-ready garage features an epoxy floor and service door, and the wide walk-up daylight basement includes a full bath, partial tile flooring, and rough-ins—ready for your custom finish. With 400 amp electric service, fiber internet availability, and unbeatable access to major commuter routes, this home combines top-tier functionality with an ideal location. Located just minutes from Winchester Medical Center, Rock Harbor Golf Course, Shenandoah National Park, and Winchester’s popular Apple Blossom Festival, you’ll enjoy both convenience and lifestyle. Don’t miss this rare opportunity—schedule your tour today!

103 Derrynan, Winchester

Listing courtesy of Burch Real Estate Group, LLC. Contact:

Selling Office: Colony Realty.

132 Cahille Dr, Winchester
$679,900
4 Beds ⋅ 4 Baths
Prime Winchester location! 3-car garage and spacious driveway! This dream home is located minutes to commuter Routes 7, 50 and 81 and minutes from shopping, dining and entertainment in Old Town Winchester! Nestled in the prestigious Raven Pointe community, this exquisite Colonial home embodies luxury and sophistication. Built in 2005, this lovingly maintained home features a harmonious blend of classic elegance and modern amenities, offering an unparalleled lifestyle. Step through the front door into the gorgeous two story foyer, featuring gleaming hardwood floors and a gorgeous open oak staircase. To the left, is the inviting dining room with extensive millwork (wainscotting, chair rail and crown molding). Throughout the home, you'll find beautiful millwork. To the right, you'll find the ideal office/music/sitting room with lighted double doors and hardwood floors with a carpet insert which creates a very peaceful space. The Gourmet kitchen is a Chef's dream, featuring double ovens, a hood over the cooktop, a spacious eat-in area, updated lighting and a dry bar, perfect for entertaining. Relax in the inviting Family Room, complete with a stacked stone gas Fireplace or step outside to enjoy coffee or your next novel on the Wrap-around Porch. The Powder Room is perfectly located off of the Foyer, tucked between the office and Family Room. Want to get away from it all and relax? Retreat upstairs to the tranquil Primary Suite, which includes a lavish bath with a soaking tub that will make you fall in love with baths again, a standing shower, his and her vanities, water closet and two generous walk-in closets. A beautiful gas fireplace, box ceiling and sitting area, completes your spa-like sanctuary. You won't want to leave! Additionally. upstairs, you'll discover a conveniently located Laundry Room, three Bedrooms all with ample closet space and a Hall Bath which also connects to one of the bedrooms, for your guests or other family member. The fully finished Basement, equipped with wide side entrance walk-up stairs, provides additional living space. On this level you'll find a Home Theatre with cabinetry and a built in wine fridge, a Rec Room that's being utilized as a Home Gym, a Multi-purpose Room/office space, additional storage and a Full Bath featuring a standing shower and ceramic tile flooring. The possibilities are endless for this level! Enjoy the convenience of a three-car, side-entry garage (work-bench conveys) with additional parking on the paved driveway which would accommodate three to four more vehicles for guest parking. Outside, the extensively landscaped 0.28-acre lot features, a manicured front lawn and a serene garden view in the back, complemented by a charming patio and wrap-around porch with a ceiling fan, perfect for outdoor dining or morning coffee. The hardscape and landscaping included with this home is absolutely lovely. Sit back and recharge, relaxing next to the water features in the fenced back yard or toast marshmallows at the firepit. Located in a tranquil suburban setting, this home offers a peaceful retreat while remaining close to vibrant local amenities. Experience the epitome of luxury living in this truly stunning home, where every detail has been thoughtfully curated for your comfort and enjoyment. Don’t miss the opportunity to make this dream home yours! *(Electric fence for the front and back yard will convey). Home also has a chair lift that is NOT currently installed, Sellers will also convey this with the home (if the Buyers are interested.) Internet and cable options - Glow Fiber, Verizon and Comcast are all available at this property.

132 Cahille Dr, Winchester

Listing courtesy of Century 21 Redwood Realty. Contact:

Selling Office: Real Broker, LLC.

106 Doolin Ave, Winchester
$675,500
4 Beds ⋅ 5 Baths
Awarded “Home of the Year” in the prestigious Top of Virginia Homebuilders Association Parade of Homes, this extraordinary sun-drenched estate offers over 3,600 square feet of refined living space on a premier corner lot, with additional unfinished areas ready to be transformed into even more luxury living. Enhanced with fully insulated vinyl siding, the home combines timeless elegance with exceptional energy efficiency and low-maintenance luxury........................................................................................................................................ The upper level features four spacious bedrooms and three beautifully renovated full baths, highlighted by an exceptional owner’s retreat with gleaming hardwood floors, an oversized custom walk-in closet, and a lavish spa-inspired bath. Enjoy dual vanities, a jetted soaking tub, an expansive walk-in shower, a separate water closet, and a dramatic double-sided fireplace shared between the bedroom and bath, creating the perfect private sanctuary. A private princess suite includes brand-new carpeting and its own en-suite bath, while two additional generously sized bedrooms, an updated full bath, and a thoughtfully designed upper-level laundry room with utility sink complete the level........................................................................................................... Designed for both elegant entertaining and everyday comfort, the main level showcases rich hardwood flooring throughout the study, formal dining room, and expansive great room. At the heart of the home is a chef-inspired gourmet kitchen featuring high-end stainless steel appliances, a large center island, double wall ovens, gas cooktop, custom finishes, and seamless flow into the inviting family space anchored by a stunning stone fireplace. Step outside to the covered porch accessible from both the great room and dining room, or unwind in the beautifully landscaped backyard with an elegant patio setting....................................... The walk-up lower level offers an expansive recreation room with bar area, an additional half bath, and abundant unfinished space ideal for a future home theater, fitness studio, wine cellar, or guest suite — allowing you to further customize this spectacular residence to your lifestyle.

106 Doolin Ave, Winchester

Listing courtesy of RE/MAX Allegiance. Contact:

Selling Office: Pearson Smith Realty LLC.

140 Cahille Dr, Winchester
$640,000
4 Beds ⋅ 3 Baths
Welcome to effortless main-level living in this beautifully appointed home, where spacious interiors, elegant finishes, and exceptional functionality come together seamlessly. Thoughtfully designed with three bedrooms on the main level, this residence offers the convenience of single-level living while providing an expansive finished lower level for additional recreation, entertaining, and guest accommodations. <br><br> Filled with natural light, the open and airy floor plan showcases soaring ceilings, updated flooring installed in 2019, updated fixtures, rich hardwood flooring, and timeless architectural details throughout. The stunning great room serves as the heart of the home, featuring vaulted ceilings, oversized windows, and a striking stone fireplace that creates a warm and inviting atmosphere. Adjacent to the great room, the dining area offers an elegant setting for everyday living and special occasions alike. <br><br> The gourmet kitchen serves as a natural gathering place, featuring granite countertops, abundant cabinetry, stainless steel appliances, gas cooking, and an expansive breakfast bar ideal for casual meals and entertaining. The adjoining breakfast area overlooks the backyard and connects effortlessly to the surrounding living spaces. <br><br> The private primary suite serves as a peaceful retreat, highlighted by a beautifully renovated en suite bathroom completed in 2024. Thoughtfully updated with modern finishes, dual vanities, a spacious glass-enclosed shower, and stylish fixtures, the space offers a spa-like experience at home. Two additional bedrooms on the main level provide comfortable accommodations for family, guests, or a dedicated home office. Additional bathrooms were also updated in 2024, adding to the home's move-in ready appeal. A conveniently located laundry room further enhances everyday functionality. <br><br> The fully finished lower level dramatically expands the home's living space and offers exceptional versatility. An enormous recreation room provides endless possibilities for entertaining, movie nights, game days, fitness equipment, or creating multiple gathering spaces. A spacious fourth bedroom and full bathroom create an ideal guest suite, while a dedicated bonus room and separate workshop offer outstanding flexibility for hobbies, crafts, projects, storage, or a home workspace. <br><br> Outdoor living is equally impressive. A spacious screened porch serves as a true extension of the home, providing the perfect place to relax and enjoy the outdoors in comfort. Complete with a ceiling fan and ample room for conversation seating, this inviting retreat can be enjoyed throughout much of the year. The large Trex deck offers additional space for grilling, dining, and entertaining while overlooking the beautifully landscaped yard. Mature plantings and attractive curb appeal create a welcoming first impression and enhance the home's overall charm. <br><br> Residents enjoy a well-maintained neighborhood with an active homeowners association and access to highly regarded schools. Ideally positioned for convenience, the home is just minutes from shopping, dining, healthcare facilities, and everyday amenities, while offering easy access to Route 7, Route 50, Interstate 81, and Northern Virginia commuting corridors. Historic Old Town Winchester is just a short drive away, offering charming boutiques, locally owned restaurants, entertainment venues, farmers markets, and year-round community events. Combining spacious main-level living, extensive finished lower-level space, thoughtful updates, and an exceptional location, this home delivers the perfect blend of comfort, convenience, and Shenandoah Valley living.

140 Cahille Dr, Winchester

Listing courtesy of Keller Williams Realty. Contact:

Selling Office: Re/Max Roots.

How much is your home worth?

Get instant property value now!