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$329,000
3 Beds ⋅ 2 Baths
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 with breathtaking mountain and ridge views and the peaceful, private setting you've been dreaming about. This isn't simply an older mountain home with a few cosmetic updates. The property underwent an extensive renovation in 2023, bringing together the charm and character of a chalet in the woods with the comfort and finishes today's buyers are looking for. Major improvements include a new roof, siding, windows, HVAC system and ductwork, water heater, appliances and decks, along with updated flooring and fresh paint throughout. The kitchen was beautifully renovated with quartz countertops, and the bathrooms were updated as part of the transformation. So much of the work has already been done—leaving you more time to simply enjoy the setting. Perfect as an everyday home, weekend getaway or second-home retreat, this is a place made for slowing down. Wake up surrounded by the woods, enjoy your morning coffee against a mountain backdrop, spend quiet evenings by the fireplace, and experience the kind of privacy that's increasingly hard to find within reach of Northern Virginia and the Washington, D.C. area. Here, getting away doesn't mean giving everything up. Strong cell service and high-speed internet options help keep you connected, while nearby Winchester puts shopping, dining and everyday conveniences within reach. Spend the day enjoying the outdoors at The Cove, then head into historic Old Town Winchester to stroll the pedestrian mall, browse locally owned shops, grab a coffee or enjoy dinner at one of its many restaurants. It's a wonderful combination of mountain living, outdoor recreation and a vibrant downtown nearby. WANT EVEN MORE SPACE AND PRIVACY? The home sits on approximately .29 acre, and the adjoining .89-acre parcel is also offered separately for $70,000 — MLS #VAFV2045004. Purchase both for the opportunity to enjoy approximately 1.18 acres combined, creating an even more private mountain retreat surrounded by nature. 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:

$275,000
3 Beds ⋅ 1 Baths
Tucked away in the woods of Shawneeland, this 3-bedroom, 1-bath home sits on nearly half an acre and is just 20 minutes from Winchester City. With some TLC and a little vision, this property has the potential to become a charming retreat and a place to truly make your own. Set on a partially wooded lot, the property offers peaceful surroundings and inviting outdoor spaces, including a front deck and a private rear deck. A storage shed is located in the backyard for convenience. The open-concept main level features a kitchen with upgraded quartz countertops and stainless steel appliances, a living room with a stone wood-burning fireplace, and a dining area. Also on the main level is a spacious bedroom, a full bathroom, and a dedicated laundry area. Upstairs, a spiral staircase leads to two additional bedrooms, creating a cozy and flexible layout. Enjoy the privacy and natural beauty of a wooded setting while remaining conveniently close to Winchester. Approximate updates include new roof in 2023,new water heater in 2022, new water softener in 2022, septic pumped in 2026, new pressure tank in 2024, new microwave in 2026.

132 Dogwood Trl, Winchester

Listing courtesy of RE/MAX Roots. Contact:

$317,265
3 Beds ⋅ 2 Baths
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
**Investor & Fixer-Upper Special Endless Potential on Nearly 1 Acre!** Calling all visionaries, weekend warriors, and Airbnb hosts! This secluded retreat in Shawneeland is your chance to create the mountain getaway, rental, or private homestead you've been dreaming of customized entirely to your style. Offering an estimated 2,000+ sq ft of finished living space with the potential for over 2,400 total sq ft, this home has great bones to build on: new foundation repairs, porch, roof, HVAC, and well pump/bladder (all 2012), hot water heater (2019), and washer/dryer (2016). The spacious porch was even framed with a hot tub in mind just add your finishing touches! A walk-out basement leads to an oversized attached 2-car garage, offering great flexibility for storage, a workshop, or extra living space. Set on a corner lot that was once two separate parcels and is now combined into just shy of 1 acre, this is one of the largest lots you'll find in Shawneeland with room to roam and privacy to spare. And despite the tranquil, wooded setting, you're only about 15 miles from historic, charming downtown Winchester, a destination growing fast in popularity. Bring your tools, your creativity, and your vision, this one is priced for opportunity and sold strictly As Is. No HOA Home is eligable for a FHA 203K loan. Contact agent for details.

159 Aspen Trl Trl, Winchester

Listing courtesy of EXP Realty, LLC. Contact:

$287,000
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:

$379,900
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:

$369,900
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.

107 Pinto Trl, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

$379,900
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:

$319,900
2 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.

212 Falcon Trl, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

$379,900
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.

208 Beaver Trl, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

$369,000
3 Beds ⋅ 2 Baths
Price Improvement - Now $369,000! Seller will replace carpeting prior to closing, providing the new owner with fresh, move-in-ready flooring. 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 moulding. 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!

120 Hawk Trl, Winchester

Listing courtesy of Samson Properties. Contact:

$339,900
3 Beds ⋅ 2 Baths
"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:

$310,000
3 Beds ⋅ 2 Baths
Adorable rancher in Shawneeland with access to a lake, trails, beach, and fishing. Ideally you wish for spacious living quarters,3 bedrooms, 2 full baths, and a walkout basement with a finished room for gym/office/den..well we have all that and more so come take a gander and make it your own before the summer ends.

204 Cochise Trl, Winchester

Listing courtesy of RE/MAX Roots. Contact:

$290,000
3 Beds ⋅ 2 Baths
Professional photos coming soon. Welcome home to 132 Geronimo Trail! Situated in a quiet and highly desirable neighborhood, this charming single-family home is perfect for first-time buyers, downsizers, or anyone seeking a peaceful retreat. This 1,232 square-foot rancher features 3 bedrooms, 2 full bathrooms, eat-in kitchen, living room, a brick fireplace with highly a efficient wood-burning insert, and laminate flooring throughout. Enjoy sun and shade from the comfortable deck and spacious yard with plenty of room for outdoor gatherings, gardening, or creating your own private oasis. The community features acres of greenspace, a large lake, several ponds, and playgrounds. Don't miss the opportunity to make this cozy retreat your own!

132 Geronimo Trl, Winchester

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

$339,900
3 Beds ⋅ 2 Baths
Welcome home to this charming retreat in the Shawneeland community of Winchester, Virginia. This beautifully reimagined rambler has been fully remodeled from top to bottom, offering 3 bedrooms and 2 bathrooms of modern finishes wrapped in relaxed mountain-community living. Move in and start enjoying it right away! Step outside and breathe it all in. A delightful front porch welcomes you home, while a private side porch is the perfect spot for morning coffee, evening cocktails, or simply soaking in the serenity. Inside, everything is new. Gleaming luxury vinyl plank flooring flows throughout, anchoring a fresh, contemporary feel. The brand-new kitchen features quartz countertops, stainless steel appliances, a deep sink, and crisp cabinetry ready to inspire your inner chef. Both bathrooms have been fully updated with tile and stylish, modern fixtures. The outdoor spaces are just as inviting. Natural privacy creates a peaceful, tucked-away feeling, while decorative garden beds are ready for green thumbs to dig in. A storage shed keeps tools and gear neatly out of sight. And for even more flexibility, a charming additional dwelling unit opens up a world of possibilities — home office, art studio, she-shed, man cave, or creative retreat. The only limit is your imagination! Major investments have already been made for you: new roof, siding, windows, hot water heater, and driveway. Behind the scenes, the property has also received significant upgrades to its essential systems — a new whole-house water filtration system, vertical well pressure tank with new fittings and hardware, and a new submersible pump wire with updated grounding conductors for the well; and a new D-box, header, and resealed tank for the septic system. That means low maintenance and real peace of mind for years to come. Shawneeland offers residents access to a community lake, ponds, and recreational amenities amid the natural beauty of the Shenandoah Valley — all just minutes from the conveniences of town. Schedule your visit today!

224 Hawk, Winchester

Listing courtesy of Weichert, REALTORS. Contact:

$285,000
3 Beds ⋅ 2 Baths
Charming and Move-In Ready Ranch in a Peaceful Setting! Welcome home to this beautifully refreshed single-level ranch nestled on a spacious, tree-lined lot. This inviting home features a bright and functional layout with updated finishes throughout. The kitchen offers grey cabinetry, granite countertops, and stainless steel appliances, creating a clean and modern space perfect for everyday living and entertaining. The home boasts fresh paint, updated flooring, and abundant natural light that flows throughout the living areas. Comfortable bedrooms and a well-appointed bathroom provide a practical and cozy living environment. Step outside to enjoy the porch overlooking a peaceful yard surrounded by mature trees, offering privacy and a relaxing outdoor setting. A storage shed provides additional space for tools or equipment and is equipped with electric. Perfect for first-time buyers, downsizers, or anyone seeking quiet living with modern updates, this move-in-ready home combines charm, comfort, and convenience.

110 Duwamish Trl, Winchester

Listing courtesy of Main Street Realty. Contact: