Shawneeland Homes for Sale

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:

Shawneeland Homes for Sale

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