Refine Search
Map
Sort by
$674,900
3 Beds ⋅ 2 Baths
Tucked into the heart of historic Hillsboro, this 1885 farmhouse blends post–Civil War architecture with modern comfort in one of Loudoun County’s most charming villages. The era saw both farmhouse‑style and Victorian homes built here, and this clapboard farmhouse stands out with higher ceilings, original hardwood floors, and a warm, inviting layout. Inside, you’ll find a living room with wood‑burning stove, an updated kitchen with gas cooking, clever storage, and generous light, plus a dining room with built‑ins and a cozy family room that nods to the old “sleeping porch” tradition with its distinctive windows and porch access. Upstairs, the ensuite primary bedroom is unusually generous for a historic home, offering two walk‑in closets and a renovated bath with custom shower, rain shower head, and clawfoot tub overlooking the backyard. Two additional bedrooms provide comfortable space for guests, family, or a home office, and a renovated main‑level full bath doubles as a laundry room with hex tile, subway‑tiled shower, and stackable washer/dryer. Outside, the home sits on nearly three‑quarters of an acre with a large backyard, garden shed, and valuable off‑street parking—ideal for relaxing, gardening, or entertaining while enjoying the quiet village setting. This historic home has too many upgrades and improvements to list here, including new or newer roof, windows and furnace, see listing documents for a complete list. Beyond the property itself, Hillsboro offers a preserved streetscape, artisan and community events, and convenient access to popular destinations. Wineries and breweries in Loudoun County are close by, and West Virginia attractions such as Harpers Ferry and the Charles Town racetrack & casino are within easy reach. Whether you’re seeking a character‑rich primary residence or exploring the home’s potential for short‑term rental or weekend‑getaway use, this farmhouse captures a timeless village lifestyle with strong regional appeal.

36944 Charles Town Pike, Hillsboro

Listing courtesy of Washington Fine Properties, LLC. Contact:

$1,149,990
5 Beds ⋅ 5 Baths
***OPEN HOUSE SUN AUG 2ND 1-3PM*** Welcome to Birch Hollow, a quiet cul‑de‑sac community surrounded by open common areas, a scenic neighborhood pond, and sweeping mountain views that capture the best of Western Loudoun. This beautifully maintained 6,400+ sq ft home offers a rare blend of privacy, comfort, and thoughtful updates — all priced at its recent appraised value. The main level features a highly desirable layout with three bedrooms, including a spacious and serene primary suite with beautiful natural light and peaceful views. A bright sunroom, dedicated office, and open kitchen‑to‑dining flow make the home feel both comfortable and connected. Over the past three years, the owners have invested in meaningful upgrades including professionally refinished wood floors, brand‑new side entrance steps, a freshly painted and sealed back deck, and a new stone wrap‑around walkway connecting the driveway to the deck. The front walkway has been refreshed and leveled for a cleaner, more welcoming entry, and outdoor speakers were added to enhance relaxation and entertaining. Upstairs, a private en‑suite bedroom offers an ideal guest retreat. The finished basement expands the home’s versatility with a multipurpose room, workshop space with conveying work tables, and additional areas perfect for hobbies, fitness, or recreation. Outdoor living is a standout feature. The home’s position captures peaceful views in every season, and the surrounding common areas make the property feel larger and more open than its acreage suggests. The neighborhood HOA is exceptionally lenient with an already approved plan for an outdoor pool, allowing homeowners to make improvements without restrictive oversight while maintaining shared spaces like the pond and open fields that give Birch Hollow its charm. With its flexible floor plan, premium updates, serene setting, and move‑in readiness, this home offers a rare opportunity to enjoy refined living in one of Hillsboro’s most picturesque communities. *Recent appraisal on hand supporting the list price. Happy to share upon request*

35987 Birch Hollow Ln, Hillsboro

Listing courtesy of Redfin Corporation. Contact:

$1,250,000
5 Beds ⋅ 5 Baths
COMING SOON! LOOKING for a c. 1870's Farmhouse on 21 acres near the historic town of Hillsboro? Welcome home! This charming traditional Virginia Farmhouse offers 3 stories (old log cabin portion & new additions) that offers 4000 sq ft, 5 bedrooms & 4.5 baths, hardwood floors, stone/exposed beams, home office, tin roof, double porches overlooking your inground pool, tennis court, stocked pond & the original stone spring house. The home is located in one of the best areas in the Northern Virginia Wine & Hunt Country....your neighbor is a local vineyard! More details & professional photographs coming soon! Showing appointments are available NOW in ShowingTime.

13732 Harpers Ferry Rd, Hillsboro

Listing courtesy of Corcoran McEnearney. Contact: 5406876321
$779,900
4 Beds ⋅ 5 Baths
PRICE REDUCTION!! APPRAISAL REPORT CAME BACK AT 800K. MOTIVATED SELLER. COME CHECK IT OT. Get ready to fall in love with this open floor plan, on over 1 acre of land. a peaceful escape. Hardwood floor, and plenty of space. Large front porch. A MUST SEE!!

11337 Russell Rd, Hillsboro

Listing courtesy of Smart Realty, LLC. Contact: 3012525515
$1,195,000
3 Beds ⋅ 4 Baths
OPEN SATURDAY, 7/25 FROM 2-4PM - Set on 3+ acres just outside the historic village of Hillsboro, established in 1752, this circa 1833 home began as the Salem Methodist Church and its detached schoolhouse. Both structures were built with local fieldstone walls 23 to 24 inches thick, and a late-1960s addition adds cypress siding. Today, the former church serves as a gracious entrance, with its original doors opening to a great room featuring vaulted ceilings and an expansive wood-burning fireplace. Artfully updated over the years, the home's 3,272 finished square feet still capture its true essence — from the stunning stone flooring in the former church to heart-of-pine and oak floors, black walnut fireplace mantels, and vintage wall sconces. The main house includes 3 bedrooms, 2 full baths, and 2 half baths, plus a 714-square-foot detached guest house. Historic charm and thoughtful updates come together seamlessly across both structures. The grounds are equally compelling, with a front porch, screened porch, expansive patio, manicured gardens, walking trails, and a barn for animals — all just off Route 9, amid the area's award-winning wineries, a short drive from downtown Purcellville.

14127 Harpers Ferry Rd, Hillsboro

Listing courtesy of Corcoran McEnearney. Contact: 7037771170
$2,150,000
5 Beds ⋅ 5 Baths
A Rare Estate Opportunity in the Heart of Western Loudoun's Wine Country **Attention Veterans** This home has a 5.1% rate and it is assumable!!! Welcome to a one-of-a-kind luxury estate in Hillsboro, VA — where custom craftsmanship meets unmatched privacy on over 17 acres of protected conservancy land. Built in 2023 by Carrington Homes, this semi-custom masterpiece delivers over 8,300 square feet of impeccably finished living space, featuring 5 spacious bedrooms and 5 designer bathrooms. Tucked at the end of a long, private driveway and framed by rolling pastoral farmland, this estate offers the kind of seclusion and serenity that's nearly impossible to find this close to everything that matters. Step inside to discover wide-plank upgraded hardwood floors, soaring ceilings, and exquisite architectural trim throughout. The gourmet kitchen serves as the heart of an open-concept floor plan made for effortless entertaining and everyday luxury. Generously proportioned bedrooms and beautifully appointed bathrooms create a sense of comfort and elegance in every corner of the home. Downstairs, a fully finished walkout basement adds even more flexible living and entertaining space. Outside, enjoy the best of both worlds — manicured lawn space blending seamlessly into expansive rolling, wooded, and pastoral grounds, creating your own private countryside escape. High-speed Verizon FIOS keeps you connected, even in this peaceful retreat. Minutes from the historic charm of Purcellville & Hillsboro, award-winning local wineries, and scenic country roads, yet still an easy commute to major corridors — this property offers the rare combination of rural tranquility and everyday convenience. This is more than a home — it's a legacy estate in one of Loudoun County's most coveted locations. Opportunities like this don't come often. Schedule your private tour today.

38149 John Wolford Rd, Hillsboro

Listing courtesy of Pearson Smith Realty, LLC. Contact: listinginquires@pearsonsmithrealty.com
$1,115,000
3 Beds ⋅ 2 Baths
Welcome to elegant, turnkey 13855 Paris Breeze Pl, your exclusive, private happy place. Create a home of ease and beauty in this single level three bedroom, 2018 ranch stunner on 10.3 acres that effortlessly combines light, scale, and comfort. Paris Breeze sits at the convergence of community, wilderness, and agriculture, merging the best of all worlds. Whether it’s enjoying the cool mountain breeze and gazing at the meadow beyond the historic stone wall on the shaded, custom stamped back patio, hiking into your woods on cleared trails to lose your mind and find your soul, hosting cozy neighborhood gatherings around the fire pit, or starting your own viniculture project, this property has it all and does it with style. Paris Breeze features fully upgraded ceiling fans and light fixtures, upgraded primary bath barn doors, a new storage shed, updated landscaping hugging the home perimeter and throughout the front and back yard, newly planted evergreen and native trees, Tree of Heaven removal, and more! Ample cabinet space, pantry, island, and gorgeous modern granite countertops grace the gourmet kitchen. HVAC has been regularly and recently serviced. In the versatile basement, 10ft ceilings lend an expansive feel. The lower level also features a rough in for plumbing and has been framed and wired for a fourth bedroom. Active Radon mitigation was installed in 2024, in addition to a new well pump still under warranty. Two main electric service panels at 200 amps each provide substantial power for a workshop or electricity for the shed. This home sparks joy! You are invited to come to the heart of wine country, imagine yourself unwinding on a soft summer evening after a rain, watching the sun set behind the mountain or stargazing while listening to water flow through the meandering creeks in your woods.

13855 Paris Breeze Pl, Hillsboro

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

$1,799,000
4 Beds ⋅ 5 Baths
Now Offered at $1,799,000 Welcome to a truly one-of-a-kind custom estate, thoughtfully designed by Homes of Atlanta and built in 2014 to combine timeless craftsmanship with exceptional flexibility for today’s lifestyle. Privately situated on 3 picturesque acres with no HOA, this remarkable property is ideal for multigenerational living, automotive enthusiasts, hobbyists, or anyone seeking space without compromise. Rich hardwood flooring, quality finishes, and thoughtfully designed living spaces create an inviting atmosphere. The main level features formal living and dining rooms, a private office, and a spacious gathering area centered around a beautifully appointed kitchen with Thomasville cabinetry, granite countertops, and GE Profile stainless steel appliances. One of the home’s most distinctive features is the private main-level guest suite, complete with its own kitchen featuring matching Thomasville cabinetry and granite countertops, a full bath, bedroom, and additional living space. Use it as a comfortable suite for extended family, guests, or a live-in caregiver—or adapt the space to suit your current lifestyle as a media room, exercise room, family room, game room, or combination of uses. A conveniently located main-level laundry room includes an LG washer and dryer. Upstairs, three generously sized bedrooms each feature a private ensuite bath, including an elegant primary suite designed as a peaceful retreat. An elevator shaft is already in place, providing the opportunity for future elevator installation and enhanced accessibility. The level backyard offers endless possibilities for a future pool, outdoor entertaining, gardens, or simply enjoying the privacy of the surrounding acreage. A charming 16' x 24' outbuilding, designed to complement the detached garage, is currently used for storage but could be transformed into a home office, potting shed, creative studio, fitness space, or fun and relaxing she shed. Car collectors and hobbyists will appreciate the extraordinary heated and cooled detached garage. Equipped with two removable automotive lifts, the building can accommodate up to eight vehicles and includes a convenient half bath. Above the garage is a beautifully finished one-bedroom apartment—ideal for guests, a private office, or independent living. Additional features include: Verizon Fios high-speed internet Private well and conventional septic system Chickens welcome No HOA Offering an exceptional combination of craftsmanship, versatility, and future-forward design, this custom estate presents a rare opportunity to enjoy luxury living with room to grow, gather, and create lasting memories.

16081 Purcellville Rd, Hillsboro

Listing courtesy of Hunt Country Sotheby's International Realty. Contact:

$1,320,000
4 Beds ⋅ 4 Baths
Mountain views, open pastures, and 10 beautiful acres create the perfect Western Loudoun retreat. Live or Airbnb with so many potential!! Located just minutes from historic Hillsboro and downtown Purcellville, this updated property offers nearly 4,000 finished square feet, privacy, and endless possibilities. Originally built in 1969, the home has been extensively updated over the years. Major improvements include HOt Water heater (2025) Washer & Dryer (2024), Windows and Doors (2013), complete Electrical Rewiring (2013), a 20'x50' addition (2014), a remodeled kitchen with cabinets and appliances (2014), new septic system (2014), Roofs on the house and garage (2014), Siding on the garage and sunroom (2014), Replacement HVAC system (2020), Barn Roof (2021), and a finished 20'x50' lower level completed in 2022. Additional improvements include upgraded insulation, backup generator system, and attic insulation upgrades. The main level features hardwood floors, high ceilings, abundant natural light, and beautiful views from nearly every room. The updated kitchen opens to the living and dining areas, while the family room offers a wood-burning fireplace. The spacious sunroom with vaulted ceilings is the perfect place to enjoy the surrounding countryside year-round. The primary suite offers peaceful views and a private bath. A secondary bedroom includes a private bath, while the third bedroom is served by a full hall bath. An oversized laundry room provides additional storage and everyday convenience. The walkout lower level includes a fourth bedroom, full bath, and large recreation room. Approximately 1,000 square feet of unfinished space offers storage or future expansion opportunities. Outdoor living includes a front porch, rear patio with pergola, mature landscaping, and scenic mountain views. The property is currently enrolled in open space use and offers numerous opportunities. The three-stall barn conveys as-is. The detached 1,540-square-foot garage and workshop includes a heated section and provides exceptional space for vehicles, hobbies, equipment, or a home business. Currently operates as a successful AIRBNB| VRBO (short-term rental), this unique property offers opportunities as a private residence, weekend retreat, equestrian property, or investment opportunity. Conveniently located just off Route 9 with easy access to Airport, Purcellville, Hillsboro, wineries, breweries, and commuter routes.

13471 Sagle Rd, Hillsboro

Listing courtesy of Samson Properties. Contact: 7033788810
$719,000
4 Beds ⋅ 3 Baths
Historic charm with modern updates! A century old and beautifully maintained, this Loudoun Heights farmhouse sits on 1.6 acres of landscaped grounds. The scenic setting welcomes you in with mature trees, a rose hedge, crape myrtles, established blackberries, and an irrigated garden, all framed by landscape lighting and a paved driveway. A generous front porch invites you to slow down and relax before stepping inside, where refinished original hardwood floors run throughout the home, paired with fresh paint and restored windows. The foyer opens to a formal dining room with a bright bay window, plus a separate formal living room for entertaining or everyday enjoyment. The family room flows naturally into the kitchen and casual eat-in dining area, with sliding doors leading to the deck for grilling and gathering. The kitchen has been updated with granite countertops and upgraded appliances including a gas cooktop, refrigerator, and dishwasher. A powder bath features new granite, vanity, and mirror, and the spacious laundry room includes a remodeled shower, refreshed cabinetry and closets, and an upgraded washer and dryer. Upstairs, the primary suite offers a fully remodeled en suite bath, with additional on the secondary upstairs bath. Interior closets throughout the home have also been remodeled. Outdoors, a screened porch with a television and sun-blocking shade extends your living space into the picturesque grounds. Another standout is the stone garage with its own heating and cooling, offering endless possibilities such as a studio, workshop, or guest space. Major systems have been brought current as well, with new first-floor HVAC, the garage HVAC, water heater, gutter guards, a generator that backs up one of the 2-200amp panels with automatic transfer switch, and 50-amp RV service. The location puts you minutes from Harpers Ferry and its restaurants, shops, and historic landmarks, as well as a short drive to historic Hillsboro and numerous parks, trails, wineries, and breweries. A rare combination of history, acreage, and turn-key living in a sought-after corner of Loudoun County.

37151 Branchriver, Hillsboro

Listing courtesy of Keller Williams Realty. Contact: 7036690099
$1,595,000
4 Beds ⋅ 5 Baths
Gorgeous homes in an idyllic setting - Welcome to The Ridges! 1-2 acre Home sites in the Western Loudoun countryside in Hillsboro. Base price shown is for the Magnolia Way Floorplan and we have many other plans including those with first floor primary suites, farmhouse kitchens, multi-generational options and our new Transitional Collection. All homes include exceptional standard features including 10' main level ceilings, hardwood floors, upgraded cabinetry and countertops, extensive trim package, and HardiePlank exterior. Plans are ready to be customized! Visit our DECORATED MODEL HOMES AND SALES OFFICE-16670 & 16658 Huntwick Place, Hamilton , VA 20158. Directions from Leesburg: Route 7 west to Hamilton Station Rd exit. Turn right on Hamilton Station Rd. Right on Colonial Hwy. Right on Ivandale St. and proceed under Rte 7. Ivandale Farm is on the right near the intersection of Ivandale Rd. and Piggott Bottom Rd. Open Daily 11-5. Ask about Closing Cost Credit! HOA fees are estimates Features, square footage, beds & baths are per base floor plans.

36660 Heskett Ln, Hillsboro

Listing courtesy of Pearson Smith Realty, LLC. Contact: listinginquires@pearsonsmithrealty.com
$1,405,000
4 Beds ⋅ 4 Baths
Gorgeous homes in an idyllic setting - Welcome to The Ridges! 1-2 acre Home sites in the Western Loudoun countryside in Hillsboro. Base price shown is for the Huntwick Farm Floorplan and we have many other plans including those with first floor primary suites, farmhouse kitchens and multi-generational options All homes include exceptional standard features including 10' main level ceilings, hardwood floors, upgraded cabinetry and countertops, extensive trim package, and HardiePlank exterior. Plans are ready to be customized! Visit our DECORATED MODEL HOMES AND SALES OFFICE-16670 & 16658 Huntwick Place, Hamilton , VA 20158. Directions from Leesburg: Route 7 west to Hamilton Station Rd exit. Turn right on Hamilton Station Rd. Right on Colonial Hwy. Right on Ivandale St. and proceed under Rte 7. Ivandale Farm is on the right near the intersection of Ivandale Rd. and Piggott Bottom Rd. Open Daily 11-5. Ask about Closing Cost Credit! HOA fees are estimates Features, square footage, beds & baths are per base floor plans.

36660 Heskett, Hillsboro

Listing courtesy of Pearson Smith Realty, LLC. Contact: listinginquires@pearsonsmithrealty.com
$999,000
3 Beds ⋅ 3 Baths
THE MANN HOUSE — A RARE OPPORTUNITY ON 12 ACRES The Mann House is a 1740 log and stone estate on 12.08 acres in western Loudoun County, with frontage on Catoctin Creek. Built by John Mann on land originally purchased from Thomas Fairfax — cousin of Lord Fairfax — it's one of Virginia's oldest privately held homes, owned by just five families in nearly 300 years. A Property With Options Live in it, work it, or build a business around it. Zoned AR1, the property supports agricultural, equestrian, and low-density commercial uses. The land is suited to a hobby farm (goats, llamas, bees), boutique vineyard, farm winery, wellness retreat, bed and breakfast, short-term rental, or boutique wedding venue (subject to Loudoun County approval). Located just minutes from Loudoun's wine trail and Hillsboro's scenic corridor, with rolling pastures, wooded trails, and creek frontage. Historic designation may also qualify the property for state and federal tax credits on approved restoration or preservation work. The Home Three bedrooms, 2.5 bathrooms, 2,071 square feet. The original character is intact: hand-hewn log walls, wide-plank pine floors, two massive fieldstone fireplaces, and authentic wood paneling throughout. The kitchen has been updated with Argentine and Brazilian marble countertops, custom cabinetry, stainless steel appliances, and a striking exposed beam overhead — built for gathering. A stone-lined root cellar offers wine storage or a unique historic feature, and the original spring house, summer kitchen, and historic outbuildings remain on the property. Built to Support a Bigger Vision The infrastructure has been intentionally sized and updated to support both family living and business use: Well: 963-foot deep private well connected to an underground river, rated for up to six (6) bedrooms. Big Blue whole-house filtration, flushing filtration system, and new pressure tank (February 2025). Septic: Designed for a six (6) bedroom residence — providing ample capacity for expansion or commercial use. Holding tank and main tank upgraded with new pump, power, and alarm in Fall 2023. Electrical: Two 200-amp panels (42-pole main + 24-pole secondary dedicated to kitchen and HVAC), plus Dominion Energy WiFi-monitored smart meter (2023). HVAC: Two split-system 5-ton heat pumps (one per level), main level replaced 2020, upper level replaced 2023. Ductwork professionally cleaned with UV purification system (2024). Roof: Standing seam metal on both the main residence and rustic log cabin — a true "install once" investment-grade roofing system. Recent Updates New LG stacking washer and dryer (September 2025) New Bosch dishwasher (December 2025) New pressure tank (February 2025) Full plumbing, electrical, and HVAC inspections completed by Appleton Campbell (October–December 2024) Ductwork UV purification system installed (December 2024) Bath faucets and shower heads replaced (2023) The Bottom Line The Mann House offers the privacy and character of early colonial Virginia with the comfort and reliability buyers expect today — and well, septic, and electrical capacity built for far more than a 3-bedroom home. It's a legacy estate ready for family living, business vision, or both. Offered at $999,000

37275 Charles Town Pike, Hillsboro

Listing courtesy of Pearson Smith Realty, LLC. Contact: listinginquires@pearsonsmithrealty.com
$1,299,900
4 Beds ⋅ 5 Baths
Owners offering $10,000 closing cost credit with acceptable contract offer! Welcome home to this stunning colonial peacefully situated on a 1.71 acre lot with over 5,300 square feet of living space & a Tesla solar roof system that was installed in 2025. This premium solar roof system has a Powerwall battery back up supply to provide power during power outages! The covered front porch greets you as you enter into the front foyer. Spacious living room, formal dining room & privately tucked place library on the main level ideal for working from home. Grand two story family room with stone surround gas fireplace & tons of light. Expansive gourmet kitchen with center island, stainless steel appliances, upgraded backsplash & morning room extension with access to rear yard for future outdoor space. Main level mudroom with additional exit to the outside & half bath too. Large primary suite with coffered ceiling, walk-in closet & luxurious bath with soaking tub & separate shower. The second bedroom features private bath. Third & fourth bedrooms share a spacious third bath. Walk-up lower level with recreation room with new carpet in 2025, 5th bedroom/den, fourth full bath, den/craft room & storage room. Oversized three car garage with car charger & expanded driveway allowing for additional parking. This home is peacefully located on a paved cul-de-sac street with a large rear yard providing ample open space as well as trees providing privacy.

14963 Creek Point Ct, Hillsboro

Listing courtesy of Pearson Smith Realty, LLC. Contact: listinginquires@pearsonsmithrealty.com
$169,900
"All negotiation, Questions through owner" Welcome to this stunning 2.5-acre lot with breathtaking mountain views! Perfectly situated and prepared for your dream build, this property offers the ideal canvas for your custom home. Bring your builder and start turning your vision into reality!" "Buyers Please do your own research" If you have any questions or concerns about the property, please contact the relevant county authorities, including the zoning office, tax department, environment and development section to confirm that your intended use of the property is permitted. My client seller bought this lot as raw land, and unfortunately, I don't have any additional documents or information to provide beyond what is publicly available. Please see document section for old documents. Bring your builder and build a house.

15375 Ashbury Overlook Ln, Hillsboro

Listing courtesy of Smart Realty, LLC. Contact: 3012525515
$350,000

Stony Point Rd, Hillsboro

Listing courtesy of Inmobiliaria De Las Casas LLC. Contact: 5713539363
$349,999
Welcome to your future mountain retreat in Western Loudoun County! This 2.53 acre building lot on the beautiful Short Hill Mountain lot boasts sweeping, hard-to-find views and total privacy. Long-range elevated views of The Valley make this lot perfect for a custom home, investment build, or a multitude of other possibilities under AR1 zoning. Properties with this combination of terrain, access, and scenery are extremely limited. The lot features mature timber, natural contours for multiple potential homesites, and the peace and seclusion for a premium build location. Adjacent parcels are available as well.

Digging Bear Ln, Hillsboro

Listing courtesy of Samson Properties. Contact: 7033788810
$7,500,000
A rare and distinguished offering in the heart of Loudoun County's celebrated wine corridor, 868 Estate Vineyards stands among Virginia's most decorated and dynamic wine estates. Fresh off a standout showing at the 2026 Virginia Governor's Cup — two Gold Medals (2023 Meritage, 2022 Meritage) and two Silvers (Cabernet Franc, Sauvignon Blanc) — the estate continues to build on its landmark win of the 2020 Governor's Cup for its 2017 Vidal Blanc Passito, cementing its place among the Commonwealth's most consistently awarded producers. Set across approximately 120 rolling acres, with 21 acres currently under vine, the property offers both immediate production strength and meaningful room to grow. The vineyard reflects thoughtful site selection and varietal diversity, with plantings that include Chambourcin, Chardonel, Petit Verdot, Cabernet Franc, Tannat, Sauvignon Blanc, Petit Manseng, Merlot, Viognier, and Nebbiolo. Substantial additional acreage supports future vineyard expansion, agritourism, or complementary estate improvements — giving the next steward room to scale while preserving the property's pastoral character. The recognition runs deep. The 2023 Sauvignon Blanc earned Best in Class at the 2025 Loudoun Wine Awards and a Gold at the Virginia Governor's Cup, joined by Golds for the 2022 Meritage and 2022 Chardonnay. The 2023 Meritage also earned a Gold Medal and 93 points from the American Wine Society. A comprehensive list of awards and scores is available upon request. The winery is fully equipped as a turnkey production and hospitality operation, including a temperature-controlled steel tank room, barrel aging room, and dedicated case storage, with vineyard and winery equipment, machinery, tanks, barrels, and wine inventory included in the sale. Guest-facing amenities are equally compelling: a well-established tasting room with a loyal regional following, a covered pavilion, a large permanent canopy built for weddings and private events, and a pergola and outdoor gathering spaces overlooking the vines — supporting diversified revenue through retail sales, wine club membership, private events, and destination tourism. Adding further depth are several significant structures: an 1840 manor house awaiting restoration, a winemaker's cottage with supporting outbuildings, and the former acclaimed farm-to-table restaurant, Grandale Farm, complete with commercial kitchen infrastructure and poised for reinvention as a culinary destination. Few Virginia wineries offer this combination of vineyard scale, award-winning production, event capacity, and culinary potential within a single integrated estate. The sale includes two LLCs encompassing the real estate, vineyard plantings, and operational winery assets — a seamless, turnkey acquisition. 868 Estate Vineyards is more than a winery purchase; it's the opportunity to steward an established, statewide-recognized brand with significant growth potential and lasting legacy in one of Virginia's most vibrant wine regions.

14001 Harpers Ferry Rd, Hillsboro

Listing courtesy of Hunt Country Sotheby's International Realty. Contact: (540) 687-8500
$7,500,000
5 Beds ⋅ 10 Baths
A rare and distinguished offering in the heart of Loudoun County's celebrated wine corridor, 868 Estate Vineyards stands among Virginia's most decorated and dynamic wine estates. Fresh off a standout showing at the 2026 Virginia Governor's Cup — two Gold Medals (2023 Meritage, 2022 Meritage) and two Silvers (Cabernet Franc, Sauvignon Blanc) — the estate continues to build on its landmark win of the 2020 Governor's Cup for its 2017 Vidal Blanc Passito, cementing its place among the Commonwealth's most consistently awarded producers. Set across approximately 120 rolling acres, with 21 acres currently under vine, the property offers both immediate production strength and meaningful room to grow. The vineyard reflects thoughtful site selection and varietal diversity, with plantings that include Chambourcin, Chardonel, Petit Verdot, Cabernet Franc, Tannat, Sauvignon Blanc, Petit Manseng, Merlot, Viognier, and Nebbiolo. Substantial additional acreage supports future vineyard expansion, agritourism, or complementary estate improvements — giving the next steward room to scale while preserving the property's pastoral character. The recognition runs deep. The 2023 Sauvignon Blanc earned Best in Class at the 2025 Loudoun Wine Awards and a Gold at the Virginia Governor's Cup, joined by Golds for the 2022 Meritage and 2022 Chardonnay. The 2023 Meritage also earned a Gold Medal and 93 points from the American Wine Society. A comprehensive list of awards and scores is available upon request. The winery is fully equipped as a turnkey production and hospitality operation, including a temperature-controlled steel tank room, barrel aging room, and dedicated case storage, with vineyard and winery equipment, machinery, tanks, barrels, and wine inventory included in the sale. Guest-facing amenities are equally compelling: a well-established tasting room with a loyal regional following, a covered pavilion, a large permanent canopy built for weddings and private events, and a pergola and outdoor gathering spaces overlooking the vines — supporting diversified revenue through retail sales, wine club membership, private events, and destination tourism. Adding further depth are several significant structures: an 1840 manor house awaiting restoration, a winemaker's cottage with supporting outbuildings, and the former acclaimed farm-to-table restaurant, Grandale Farm, complete with commercial kitchen infrastructure and poised for reinvention as a culinary destination. Few Virginia wineries offer this combination of vineyard scale, award-winning production, event capacity, and culinary potential within a single integrated estate. The sale includes two LLCs encompassing the real estate, vineyard plantings, and operational winery assets — a seamless, turnkey acquisition. 868 Estate Vineyards is more than a winery purchase; it's the opportunity to steward an established, statewide-recognized brand with significant growth potential and lasting legacy in one of Virginia's most vibrant wine regions.

14001 Harpers Ferry Rd, Hillsboro

Listing courtesy of Hunt Country Sotheby's International Realty. Contact: (540) 687-8500
$525,000
3 Beds ⋅ 3 Baths
PLEASE NOTE that the Owner has listened to the current market, Price has been reduced to $525,000. It is a property of beautifully preserved quality on ¾ of an acre in an urban setting. Most unusual! When compared to equivalent historic properties it is now very competitively priced! This fine, brick dwelling originating from the18th c. is situated in Hillsboro on Maryland's peaceful Eastern Shore. Hillsboro, nestled along the Tuckahoe River, conveniently located to all that is important to the Eastern Shore's sought-after lifestyle. Public landing with dock and kayak lauch is just a block away. The WILLIAM SMITH HOUSE, built in 1794, exemplifies the world of a successful Grain Merchant living in an important hub for grain and tobacco. The house has been altered slightly through the many decades, but the character of the original building dominates the architecture and "feel" of its 1794 era. Its charm and elegance remain. The rooms are commodious and inviting. The grand center ENTRANCE HALL is punctuated by the graceful stair, fine woodwork and doors. The LIVING ROOM, as expected, is spacious and comfortable with fireplace (now gas fired), original floors, and bookshelves. The DINING ROOM, of a grand size, features a fireplace (now gas), cabinetry and glass front cupboards. Two steps down from the dining Room the fully equipped KITCHEN is found with wood floor, exposed rafters and back stairway. Open from the kitchen is the GATHERING ROOM with wood floor and wide views of the grounds and gardens. A paver path from this room leads to the driveway and parking. An open DECK offers a secluded retreat off the kitchen wing BEDROOMS and BATHS are found on second floor. Two of which have fireplaces although decorative at this time. Access to the bedroom level is either from the main grand stairway or via the back stairs. Adding to the charm is the back stair hall in the primary bedroom wing located over the kitchen and "gathering" room. The baths are delightful. A surprise outbuilding is to the rear of the grounds. A perfect spot for an office, studio or storage. Another smaller outbuilding offers more storage. The grounds feature tall mature trees and fencing. The William Smith House is all one would expect built in a gracious era with a colorful history. WHERE IS HILLSBORO?? Hillsboro lies a short distance from both Denton, Caroline County and Easton in Talbot County. Chestertown, in Kent County, is just 40 minutes. Annapolis, the Capitol of Maryland, is less than an hour. Unique shops, sailing facilities, live theater and restaurants abound. Hillsboro is from 1- 2 hours from the "rest of the world" for BWI, National and Philadelphia airports are a swift drive away. Dulles a bit further. A private airport is found in Easton. - 15 minutes. Atlantic Ocean resorts are about an hour. Adkins Arboretum is 1.5 miles. Adkins is a 400-acre native garden and preserve, provides exceptional experiences in nature to promote environmental stewardship. The Hillsboro Public Landing on the Tuckahoe is just a block from property. This property and lifestyle is an enriching experience” It awaits its next steward(s).

22005 Main St, Hillsboro

Listing courtesy of Maryland Heritage Properties. Contact: (443) 480-7342
$1,375,000
4 Beds ⋅ 4 Baths
Gorgeous homes in an idyllic setting - Welcome to The Ridges! 1-2 acre Home sites in the Western Loudoun countryside in Hillsboro. Base price shown is for the Glen Springs Floorplan and we have many other plans including those with first floor primary suites, farmhouse kitchens, multi-generational options and our new Transitional Collection. All homes include exceptional standard features including 10' main level ceilings, hardwood floors, upgraded cabinetry and countertops, extensive trim package, and HardiePlank exterior. Plans are ready to be customized! Visit our DECORATED MODEL HOMES AND SALES OFFICE-16670 & 16658 Huntwick Place, Hamilton , VA 20158. Directions from Leesburg: Route 7 west to Hamilton Station Rd exit. Turn right on Hamilton Station Rd. Right on Colonial Hwy. Right on Ivandale St. and proceed under Rte 7. Ivandale Farm is on the right near the intersection of Ivandale Rd. and Piggott Bottom Rd. Open Daily 11-5. Ask about Closing Cost Credit! HOA fees are estimates Features, square footage, beds & baths are per base floor plans.

36660 Heskett Ln, Hillsboro

Listing courtesy of Pearson Smith Realty, LLC. Contact: listinginquires@pearsonsmithrealty.com
$55,000
Seller is waiting for perk results from Caroline county health department

E/S MD RT480 Unknown, Hillsboro

Listing courtesy of Wright Real Estate. Contact: (410) 924-3111