Shawneeland Homes for Sale

NEW PRICE! NOW $299,000 YOUR MOUNTAIN ESCAPE MAY BE CLOSER THAN YOU THINK. Leave the traffic, noise and pace of everyday life behind—without getting on a plane! Tucked among the trees in the scenic Shawneeland community, 129 Rappahannock Trail is a beautifully renovated chalet-style retreat offering breathtaking mountain and ridge views, privacy and a peaceful setting. This isn't simply an older mountain home with a few cosmetic updates. Extensively renovated in 2023, the property combines the charm of a mountain chalet with modern comforts and finishes. Improvements include a new roof, siding, windows, HVAC system and ductwork, water heater, appliances and decks, along with updated flooring, fresh paint, a beautifully renovated kitchen with quartz countertops and updated bathrooms. Offering three bedrooms plus a den, two full baths, over 2,200 square feet of living space, a walkout lower level and multiple outdoor decks, this unique property is well suited for a primary residence, weekend getaway, second home or potential short-term rental investment. Enjoy morning coffee overlooking the mountains, evenings surrounded by nature and the privacy of a wooded setting on a quiet, no-through street. Strong cell service and Wi-Fi options help keep you connected, while historic downtown Winchester, shopping, dining and outdoor recreation are all within reach. **WANT EVEN MORE SPACE AND PRIVACY?** The adjoining .89-acre parcel is available separately for $70,000 (MLS #VAFV2045004), offering an opportunity to expand your mountain retreat. Whether you're looking for a peaceful escape or exploring vacation rental possibilities, this extensively renovated property offers exceptional appeal at its newly reduced price. Short-term rental use is subject to applicable regulations and approvals. Close enough to escape for the weekend. Special enough that you may never want to leave.

129 Rappahannock Trl, Winchester

Listing courtesy of Loudoun Ridge Realty, LLC. Contact:

$324,950

3 Beds ⋅ 2 Baths

A view you'll never tire of coming home to! Tucked among mature trees and established landscaping in the desirable Shawneeland community, this charming 3-bedroom, 2-bath home offers a wonderful combination of privacy, natural beauty and comfortable one-level living. Here, the surrounding scenery becomes part of everyday life, changing with the seasons and providing a beautiful backdrop throughout the year. Step onto the deck with your morning coffee and take in the peaceful surroundings and picturesque views across the Winchester landscape. From the colors of fall to the beauty of a setting sun, there is always something new to appreciate. Inside, the home offers 1,248 finished square feet of living space with 3 bedrooms, 2 bathrooms, an open plan kitchen/dining room and a spacious family room which provdes access to the beautiful front deck. The home benefits from fresh paint throughout several areas of the main level adding to the home’s bright, welcoming feel. The practical ranch-style layout provides comfortable everyday living, while the attached one-car garage adds convenience and storage. The home has also benefited from several important updates in recent years, including the HVAC system, water heater, pressure tank, and updated washer and dryer, with the roof replaced in 2021. Beyond the property itself, enjoy the natural surroundings and established character of Shawneeland, with community amenities including fishing, playgrounds, picnic areas and a four-hole golf course. And with NO HOA, homeowners can enjoy an added level of freedom that's increasingly difficult to find. Just beyond the peaceful surroundings of home, the shops, restaurants, coffee houses and historic charm of Winchester are only a short drive away. Spend an afternoon strolling the Old Town Walking Mall, meet friends for dinner, or enjoy one of the many events that bring the area to life throughout the year. Commuters will appreciate easy access to major routes including Routes 50 and 7, as well as I-81, providing convenient connections throughout the Winchester area and beyond. Travel east toward Clarke and Loudoun Counties, including Berryville, Purcellville and Leesburg, or connect with major corridors serving the greater Northern Virginia region. At 151 Huron Trail, the view isn't something you simply notice when you arrive—it becomes part of the way you live. Come experience the privacy, changing seasons and spectacular sunsets for yourself. Enjoy your tour!

151 Huron Trl, Winchester

Listing courtesy of Pearson Smith Realty, LLC. Contact:

$265,000

3 Beds ⋅ 1 Baths

Located in the wooded community of Shawneeland, approximately 20 minutes from Winchester City, this 3-bedroom, 1-bath home sits on nearly half an acre, offering the potential to become a charming retreat and a place to truly make your own. Recent updates include a roof replaced in 2023, water heater and water softener installed in 2022, pressure tank replaced in 2024, and septic system pumped in 2026. A new microwave was also added in 2026. The main level features an open-concept layout with a kitchen offering quartz countertops and stainless steel appliances, a dining area, and a living room with a stone wood-burning fireplace. A bedroom, full bathroom, and dedicated laundry area are also located on the main level. Upstairs, a spiral staircase leads to two additional bedrooms. Outside, the partially wooded lot includes a front deck, rear deck, and backyard storage shed. The setting offers a measure of privacy while remaining within driving distance of Winchester and its shopping, dining, and everyday conveniences. With its wooded location, existing features, and several key system updates, this property offers potential for buyers seeking an opportunity to renovate and personalize a home to their own preferences.

132 Dogwood Trl, Winchester

Listing courtesy of RE/MAX Roots. Contact:

$311,265

3 Beds ⋅ 2 Baths

***Price reduction*** NEW PHOTOS! Landscaping done! Professional cleaning done! New Flooring in bedrooms! Welcome to this charming three-bedroom, two-bathroom raised ranch nestled on a quiet, tree-lined street in one of the area’s most close-knit neighborhoods. Full of character and potential, this home boasts a classic floor plan just waiting for your cosmetic updates and personal design vision. A brand new roof and pressure tank! The main level features a bright living area filled with natural light, a dedicated dining space, and original hardwood flooring. Three comfortably sized bedrooms complete the upper level, including a primary bedroom with its own private en-suite bath. The full basement offers so much room to expand with a laundry area, a finished area for a possible sleeping room, ample heavy shelving units for crafting, storage or a workshop, and a walkout with sliding doors. Beyond the front door lies a vibrant, amenity-rich community known for its warm atmosphere. Neighborhood residents enjoy access to a spring-fed/man-made lake featuring a sandy beach area, swimming, fishing, and a boat ramp (gas motors are not permitted). Cherokee Beach is open to residents without a beach pass, additional smaller ponds and scenic streams located throughout the community, two community playgrounds, wooded nature walks and trails, pavilion spaces, open sports areas, and picnic spots, and covered/lighted mailbox stations and covered school bus stops.

148 Doe Trl, Winchester

Listing courtesy of Keller Williams Realty Advantage. Contact:

$295,000

2 Beds ⋅ 3 Baths

A Little Vision. A Lot of Potential. Nearly an Acre to Make It Happen! Tucked away in the wooded surroundings of Shawneeland, this spacious property offers a rare opportunity to create something truly special. Whether you envision a peaceful mountain retreat, a full-time residence, or an investment property, the possibilities are yours to explore! Situated on a generous corner lot of nearly one acre, originally two separate parcels combined into one, this property offers exceptional space, privacy, and flexibility. With approximately 2,000+ square feet of finished living space and the potential for over 2,400 total square feet, there's plenty of room to bring your vision to life. Several major improvements have already been completed, including foundation repairs, roof, porch, HVAC, and well pump/bladder (2012), along with a hot water heater (2019). The expansive porch was framed with a future hot tub in mind, creating an exciting opportunity for an outdoor retreat. A walk-out basement and oversized attached two-car garage provide additional versatility for a workshop, hobbies, storage, or future improvements. Enjoy the serenity of a wooded setting while remaining approximately 15 miles from the shops, restaurants, and historic charm of downtown Winchester. Looking for a renovation project with potential? This could be the opportunity you've been waiting for! Bring your contractor, creativity, and imagination to transform this property into something extraordinary. NO HOA! Property may qualify for FHA 203(k) renovation financing, offering eligible buyers the opportunity to finance both the purchase and qualifying improvements. Contact the listing agent for additional details. Property is being sold strictly AS IS. An opportunity to create value and make this home uniquely yours!

159 Aspen Trl Trl, Winchester

Listing courtesy of EXP Realty, LLC. Contact:

$280,000

3 Beds ⋅ 1 Baths

Located in the desirable Shawneeland community, this freshly updated three bedroom home is situated on a great corner lot with scenic views and plenty of possibilities to make it your own. The home features an updated kitchen, breakfast area, along with a detached two story garage/shed offering additional parking and storage. Step outside and enjoy relaxing evenings on the deck while taking in peaceful surroundings. Shawneeland offers an array of community amenities, including fishing, private access, playgrounds, and a four-hole golf course. With it's spacious lot, thoughtful updates, versatile outdoor space, and inviting setting, this quaint home is ready for it's next owner to make it their very own.

700 Tomahawk Trl, Winchester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$360,000

3 Beds ⋅ 3 Baths

Nestled in the Shawneeland community, this delightful Colonial home, built in 2021, offers a perfect blend of modern comfort and timeless appeal. With three spacious bedrooms and two and a half bathrooms, this residence is designed for both relaxation and entertaining. Step inside to discover warm hardwood floors that flow throughout the main living areas, creating an inviting atmosphere. The heart of the home features a cozy breakfast area, perfect for morning gatherings or casual meals. The kitchen offers appliances, including an electric oven/range, refrigerator, microwave, and dishwasher, making meal prep a breeze. The primary suite is a true retreat, complete with an en-suite bathroom that offers both privacy and convenience. Additional bedrooms provide ample space for guests or a home office, catering to your lifestyle needs. The full, unfinished basement presents a blank canvas, ready for your personal touch—imagine a game room, home gym, or extra storage. With a walkout level, windows, and plumbing for a future bathroom, this space has great potential. Outside, the generous 0.32-acre lot offers plenty of room for outdoor activities or gardening, while the driveway provides convenient parking. Enjoy the tranquility of suburban living while being just a short drive from local amenities. This home is not just a place to live; it’s a place to create lasting memories. Don’t miss the opportunity to make it yours! PRICE ADJUSTMENT!!!! Schedule your appointment NOW!

147 Doe Trl, Winchester

Listing courtesy of Coldwell Banker Premier. Contact:

$349,900

3 Beds ⋅ 3 Baths

STOP RENTING, DITCH THE TOWNHOME PURCHASE & AVOID THE RESALE HOMES! Why pay more to rent? Skip the bidding wars and 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.

103 Tonto Trl, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

$349,900

2 Beds ⋅ 1 Baths

STOP RENTING, DITCH THE TOWNHOME PURCHASE & AVOID THE RESALE HOMES! Why pay more to rent? Skip the bidding wars and 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.

101 Tonto Trl, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

$349,900

3 Beds ⋅ 3 Baths

STOP RENTING, DITCH THE TOWNHOME PURCHASE & AVOID THE RESALE HOMES! Why pay more to rent? Skip the bidding wars and 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.

123 Killbuck Trl, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

$369,000

3 Beds ⋅ 2 Baths

Welcome to 120 Hawk Trail in Shawneeland! Built in 2014, this beautifully maintained 2,800+ square foot home offers modern comfort and convenience while enjoying the established character of a mature setting and peaceful wooded surroundings. A covered front porch greets you each day, while the two-car garage with two single doors provides a highly desirable feature in Shawneeland, along with plenty of additional storage. Inside, the spacious living room showcases a high tray ceiling, crown molding, hardwood floors, and large windows that fill the space with natural light. Entertain in the separate formal dining area, enhanced by chair rail and panel molding. Cooking and meal preparation are a pleasure in the well-appointed kitchen, featuring stainless steel appliances, abundant cabinetry, and generous workspace. A bright and cheery breakfast area overlooking the large, open backyard creates a cozy spot for everyday meals, morning coffee, or casual gatherings. Designed for everyday living, the three-bedroom floor plan includes a private primary suite with its own full bathroom and large closet. A second full bathroom is conveniently located near the living areas and additional bedrooms. Both bathrooms feature tile flooring and updated vanities. Downstairs, with direct access to the garage, the full basement is ready for finishing to your specifications, with a rough-in for a future bathroom. Create a recreation room, home gym, office, workshop, guest space, or simply take advantage of the generous storage space. A separate utility area includes the washer and dryer. Outside, the nearly 1/3-acre private, tree-lined lot offers plenty of space for grilling, entertaining, gardening, or simply relaxing surrounded by nature. Lovingly maintained by its original owner, this home features fresh paint, updated lighting and bathroom fixtures, and ceiling fans throughout. Enjoy the many Shawneeland amenities, including fishing ponds, hiking trails, playgrounds, and picnic areas, while Winchester's shopping, dining, medical services, and entertainment are conveniently nearby. Modern construction, 2,800+ square feet, a two-car garage, beautiful interior details, a full basement ready for your plans, and a peaceful wooded setting - come see what makes 120 Hawk Trail so special! Seller will replace carpeting prior to closing, providing the new owner with fresh, move-in-ready flooring.The home is also offered for rent at $1,995 per month.

120 Hawk Trl, Winchester

Listing courtesy of Samson Properties. Contact:

$319,900

3 Beds ⋅ 2 Baths

Motivated seller bring offers! "Escape To Archwood" Whether you're looking for a weekend retreat or a primary residence this 3-bedroom, 2-bathroom Chalet Style home is it! With incredible mountain views, privacy and room to stretch out this home can be your happy place! Open concept on the upper level with vaulted ceilings and a large kitchen with stainless steel appliances. Primary bedroom with a sliding door to the deck and private bathroom that has a large standing shower. Pull down steps to a walk-up loft area perfect for storage. Lower level has 2 bedrooms, full bathroom and laundry area. Huge lower and upper decks perfect to drink your morning coffee or relax in the evenings while you enjoy the breathtaking views! Storage shed out back. This home was fully renovated in 2019. New LVP flooring was just installed in the kitchen, living room and hallway area. Many parts of the deck and the vinyl siding off the left side of the upper deck were replaced in 2025. New pressure tank installed in August 2026. New water treatment system installed in September of 2026. New well pump installed in September of 2026. Home is sold as is where is.

904 Archwood Trl, Winchester

Listing courtesy of Samson Properties. Contact:

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