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$1,380,000
6 Beds ⋅ 5 Baths
Calling all hobby farm and wine enthusiasts—this is the one. Set on 10 scenic acres surrounded by rolling hills and vineyards, Heskett Lane offers the perfect balance of peaceful retreat and hands-on living. A mature fruit orchard, vegetable garden, goose pen (yes—Mrs. Goose conveys and lays eggs in the spring), and a 5-car garage create endless opportunities to garden, gather, and grow. When it’s time to unwind, take a short stroll to Loco Lion Brewery or explore seven nearby wineries—all within five miles. (Uber encouraged.) Inside, over 6,000 square feet have been thoughtfully updated to blend comfort and scale. A grand foyer with a curved staircase sets the tone, leading into expansive living spaces designed for entertaining. The oversized kitchen flows seamlessly into the family room, creating a true heart-of-the-home feel. A rare main-level bedroom and full bath—plus nearby laundry—offer flexibility for guests or long-term living. Upstairs, the private primary suite is a retreat of its own, featuring three large closets, a gas fireplace, en-suite bath, and sweeping backyard views. Three additional bedrooms and two baths complete the upper level. The finished lower level adds even more versatility, with a game area, two dens, a living space, full bath, sixth bedroom, and a sauna with red-light therapy. Major updates include a detached 2-car garage (2013), paved driveway (2014), roof (2017), lower-level HVAC (2022), furnace (2023), and upper-level HVAC (2024). Professional photos and floor plan coming soon.

36430 Heskett Ln, Hillsboro

Listing courtesy of Samson Properties. Contact:

Selling Office: Pearson Smith Realty, LLC.

$900,000
5 Beds ⋅ 4 Baths
Welcome home to 15615 Whispering Knoll Court. A stunning 5-bedroom, 3.5-bath retreat nestled on 3.07 private acres in the heart of Hillsboro. Built in 2017, this thoughtfully designed home offers the perfect blend of space, comfort, and modern updates. Situated amongst the beautiful wineries and rolling countryside that Loudoun County is renowned for, and just a short drive to the charming towns of Purcellville and Round Hill, the location is as special as the home itself. Step outside to your brand new screened porch (2025) and take in the picturesque, fully fenced yard complete with a garden and newly planted trees; your own private sanctuary. Inside, the grand two-story living room with gas fireplace sets an impressive tone. Two primary suites (one on the main level and one upstairs, each with en suite baths) offer incredible flexibility for multigenerational living, guest accommodations, or simply planning for the future. The well-appointed kitchen features a large island, granite countertops, generous cabinet space, and stainless steel appliances. Fresh carpet and paint (2026), new washer (2025), new dishwasher (2025), and new microwave (2023), and all other appliances and major systems believed to be 2017. The detached 2-car garage and an 800+ sq ft unfinished basement round out this exceptional property and provide so much room to grow. You must see this rare Hillsboro gem!

15615 Whispering Knoll Ct, Hillsboro

Listing courtesy of Pearson Smith Realty, LLC. Contact:

Selling Office: Compass.

$775,000
2 Beds ⋅ 1 Baths
This delightful Cape Cod home offers a serene retreat with a stunning 10-acre lot, perfect for those who appreciate nature's beauty. Newer Radon remediation and water treatment systems in place. 2013 Roof. 4G INTERNET! So many options with this property, Custom build opportunity, AirBNB, Agritourism. Bring your Chickens & farm animals, over 9 fenced acres of gentle rolling hills, two storage shed and fantastic gardner's area. With 2 cozy bedrooms and a full bath, this residence is designed for comfort and ease. The full basement offers ample storage or potential for customization. LVP flooring throughout. Newly constructed Barn with electric, lights and water. This home is not just a property; it's a lifestyle waiting to be embraced. Discover the perfect blend of comfort and nature in this inviting haven.

36333 Stony Point Rd, Hillsborough

Listing courtesy of Keller Williams Realty. Contact:

Selling Office: Smart Realty, LLC.

$725,000
3 Beds ⋅ 3 Baths
Tucked away on 10 private, wooded acres just minutes from Harpers Ferry, this one-of-a-kind 3-bedroom, 2.5-bath home offers an estimated 2,471 square feet of living space and a rare blend of seclusion, natural beauty, and thoughtful updates. As soon as you arrive, you'll feel like you're on vacation. The property sits just off a paved road, with breathtaking views to the south and east. A welcoming foyer opens into the dramatic great room with soaring ceilings, a high-efficiency wood stove that heats two floors, and oversized picture windows that bring in the outdoors. The kitchen is well-appointed with stainless steel appliances, an oversized pantry, and a sunny eat-in area that opens directly to the covered porch, perfect for dining outside in any weather. The expansive front deck stretches across the entire home and wraps around to join the porch, making it easy to relax, entertain, or simply take in the wildlife and star-filled skies. Back inside, the main level offers a flexible bedroom ideal for guests or a home office, conveniently located next to a spacious powder room. Upstairs, you'll find two generously sized bedrooms and two full bathrooms, including a primary suite with vaulted ceilings and tranquil views of nothing but nature. The walk-out lower level offers excellent light and space for a rec room, studio, or workshop. It leads to yet another deck and provides access to the surrounding outdoor space, which is fully private and peaceful. Additional features include luxury vinyl tile flooring and a large outbuilding, perfect for projects, storage, or even parking a boat. Though you’ll feel a world away, you're just 20 minutes from the shops and restaurants of Purcellville and about 15 minutes from the MARC train to Washington, DC. Dulles Airport is under an hour away. Outdoor lovers will appreciate the proximity to the Appalachian Trail, Harpers Ferry National Historical Park, and miles of hiking along the Potomac and C&O Canal towpath. Plus, Loudoun County’s renowned wineries and breweries are all around you. This is more than a home. It’s a lifestyle. Don’t miss your chance to own this private retreat.

34942 Charles Town Pike, Hillsboro

Listing courtesy of Keller Williams Capital Properties. Contact:

Selling Office: Samson Properties.

$475,000
4 Beds ⋅ 1 Baths
Welcome to 36933 Gaver Mill Road, a hidden gem nestled in the picturesque and historic town of Hillsboro, VA, 20132. This single-family detached home, built in 1900, exudes timeless character and offers a serene retreat on a spacious 0.68-acre lot. Being sold "As-Is," this property presents a unique opportunity for those with a vision to restore and enhance its well-deserved charm. Boasting 1,192 square feet of finished living space, the home features four inviting bedrooms and a full bath. The classic wood wraparound porch invites you to relax and take in the tranquil surroundings, while the durable metal roof promises lasting protection. Inside, you'll find hardwood flooring throughout, complemented by ceiling fans that add to the home's comfort and ambiance. The kitchen is equipped with a propane gas stove and range, a refrigerator, and a washer and dryer conveniently located on the main level. Outside, a detached storage building and an additional shed/outbuilding offer versatile storage or workspace options. The property is connected to public water and sewer services and offers access to Comcast internet, supporting modern living needs. Recent updates include a brand-new mini-split HVAC/heat pump system installed throughout the home, ensuring efficient heating and cooling and new shingles on the roof. While the home requires updates and maintenance, it’s brimming with potential perfect canvas for creating your dream home. Located in Western Loudoun County, the property offers the best of both worlds: a peaceful lifestyle in the heart of Hillsboro and convenient access to nearby shopping, restaurants, wineries, breweries, and other attractions. Commuter lots are close by, with an easy commute to Northern Virginia, Maryland, and Washington, DC. The home is approximately 27 miles from Dulles International Airport and about 15 miles from the MARC Train station in Brunswick, MD. Don't miss this opportunity to own a piece of Hillsboro's history and make it your own. Schedule your private home tour today and envision the possibilities that await!

36933 Gaver Ml, Hillsboro

Listing courtesy of Keller Williams Realty. Contact:

Selling Office: Non Subscribing Office.

$400,000
2 Beds ⋅ 2 Baths
Seller is currently accepting back-up offers, feel free to schedule showings. Step into timeless charm at 36952 Charles Town Pike in the heart of historic Hillsboro. This beautifully restored 2-bedroom, 1.5-bath stone-front home blends the character of a bygone era with the comfort of modern living. Thoughtfully renovated down to the studs, it retains its historic warmth while offering updated systems and finishes throughout. The original stone façade speaks to its heritage, while inside, you’ll find a cozy layout featuring rich wood accents and a wood-burning stoves that provide both ambiance and function. Nestled in one of Loudoun County’s most picturesque villages, this home is perfect for those who appreciate craftsmanship, history, and small-town charm—all just minutes from wineries, hiking, and commuter routes. A rare gem where modern renovation meets historical soul.

36952 Charles Town Pike, Hillsboro

Listing courtesy of Innovation Properties, LLC. Contact:

Selling Office: Innovation Properties, LLC.