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Hillsboro, VA

 

In northwestern Virginia, in a section of the Blue Ridge Mountains, there is a town known as Hillsboro. Hillsboro is nestled in the Short Hill Mountain’s Hillsboro Gap, just ten miles southeast of Harpers Ferry, West Virginia, and roughly fifty-five miles northwest of downtown Washington, D.C. This tiny community is home to around one hundred residents and several gorgeous older structures, including its “Old Stone School.” This lovely building is the central feature of Hillsboro and was originally the Locust Grove Academy. Its east wing was constructed in 1874 and is the oldest part of the building. Today it is the place where many of Hillsboro’s annual events and celebrations are held.

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About Hillsboro, VA Real Estate

This rural community in Loudoun County, once known as the “Gap in the Short Hill,” is comprised of just 0.1 square miles. In addition to its peaceful, laid-back atmosphere, residents also enjoy easy access to major transportation routes, including Virginia State Route 9, known locally as Charles Town Pike. State Route 9 stretches northwest to Martinsburg and Charles Town and connects with Interstate 81. Extending southeast, State Route 9 also conveniently connects to State Route 7 which leads to Alexandria and Leesburg. And on State Route 7, between Alexandria and Leesburg, there are connections to Interstate 395, Interstate 66, and Interstate 495.

Hillsboro is one of the state’s smallest towns, despite having tripled in size in 2016 because of zoning changes. It encompasses the Hillsboro Historic District which has appeared on the National Register of Historic Places since the late 1970s. This well-preserved rural town offers an alluring mid-18th and 19th-century atmosphere. That said, it also offers many benefits of residency, which include amenities like Doukenie Winery, A Country Retreat, Fieldstone Farm, Hillsborough Vineyard and Brewery, and Stoneybrook Farm Market. Also contributing to its appeal are Hillsboro real estate opportunities. Homes for sale in Hillsboro include attached and detached homes, though most Hillsboro properties are single-family residences. Because of the relative diversity of real estate in Hillsboro, listing prices fall across a comprehensive range. If you would like to learn more about available real estate in Hillsboro, Virginia, we would love to assist you, so please do not hesitate to contact us at your earliest convenience.

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Latest Hillsboro Homes for Sale

$598,895
3 Beds 2 Baths VALO2079604 MLS ACTIVE Status
WOW - This Cape Cod style log home, circa 1850, is such a beautiful blend of historical charm mixed with tasteful, modern amenities - set on an idyllic, wooded private lot in the Hillsboro countryside. | Charming Stone Path Leads to the Welcoming Front Porch - Perfect for Rocking Chairs | Entry Area/Living Room have a Wood-Burning Fireplace, Hardwood Floors, and an Open Staircase Leading to Upper and Lower Levels | Main Level Bedroom (which could also be a family room, home office, etc.) and Main Level Full Bath with Beautiful Clawfoot Tub | Sunny Gallery Spans Rear of Main Level & Walks Out to Deck Overlooking Trees | Two Bedrooms on Upper Level have Vaulted Ceilings & Skylights and are Accessed by Separate Staircases | Primary Suite Bathroom has New, Modern Fixtures Including a Second Clawfoot Tub | Lower Level has a Fantastic Kitchen Where Old Meets New - a Huge Fireplace with Woodstove and Beamed Ceiling and also Soapstone Countertops, Open Shelving, Stainless Appliances, and a Farm Sink | Eat-In Kitchen has Ample Table Space | Rear Hall Houses the Laundry, has a Great Walk-In Pantry, and Walks Out to Rear Patio | Lower Level Also Has an Oversized Unfinished Storage Space | Separate Studio/Cottage has a Sleeping Loft and has been used as a Comfortable Guest Space with Portable Toilet, Sink, and Mini Fridge | Minutes from the Appalachian Trail, historic Harpers Ferry, and the Shenandoah & Potomac Rivers, this home was owned by its original family for 170 years and has since been loved by a professional designer who has made elegant, thoughtful updates.

35820 Charles Town Pike, Hillsboro

$850,000
3 Beds 2 Baths VALO2079530 MLS ACTIVE Status
**OPEN HOUSE SAT 9/21, 11AM-2PM**Nestled at the end of a peaceful cul-de-sac, this stunning, mostly wooded 10-acre property offers the perfect blend of seclusion and community living. Built in 2018, this custom-designed home offers three bedrooms and two bathrooms, with the convenience of main-level living. Surrounded by lush woodlands and boasting breathtaking views of both trees and mountains, this property is ideal for those seeking a tranquil retreat that still enjoys the benefits of a well-established neighborhood. As you approach the property, you'll immediately appreciate its prime location at the end of the cul-de-sac, ensuring minimal traffic and a sense of privacy. The backyard is inviting, featuring a lovely covered porch that is perfect for morning coffee or evening relaxation. From the porch, you’ll enjoy panoramic views of the surrounding woods and distant mountains—ideal for watching the sunset or simply unwinding with a book. Additionally, the backyard includes a custom-built firepit, offering a great spot for gathering with family and friends for late-night conversations under the stars. Step inside, and you'll find that this home was designed with both style and functionality in mind. With an open-concept layout, the main living areas are spacious and filled with natural light, thanks to large windows that offer views of the surrounding landscape. The gleaming hardwood floors throughout the main living spaces provide warmth and elegance, complementing the home’s modern design. The family room, a central feature of the home, is the perfect place to relax. It boasts a cozy fireplace, ideal for cold winter nights, and French doors (with a retractable screen) that lead directly to the backyard. These doors not only fill the room with light but also offer easy access to the porch and the outdoors, making it ideal for indoor-outdoor living. For those who love to cook and entertain, the gourmet kitchen will be a dream come true. At the heart of the kitchen is a massive island topped with stunning granite, providing ample workspace for meal preparation as well as a perfect spot for casual dining or entertaining guests. The abundance of cabinetry offers plenty of storage space, keeping the kitchen clutter-free, while the breakfast nook, surrounded by windows, provides a cozy spot to enjoy your morning coffee while taking in the natural beauty of the property. The home offers three well-appointed bedrooms, each designed for comfort and privacy. The primary suite, located on the main level, is a true retreat. It features large windows that let in plenty of light and offer views of the wooded landscape. The en-suite bathroom is elegantly designed, featuring a double vanity with granite countertops and a separate walk-in shower. The additional two bedrooms are equally spacious, offering plenty of room for family members or guests. They share a well-designed second bathroom that also features granite countertops, modern fixtures, and a combination tub/shower. One of the standout features of this home is the walk-up basement, which offers over 2,000 sf of unfinished space. Already framed out, this area provides endless possibilities for customization. Whether you envision a home theater, gym, additional bedrooms, or even a second family room, the basement offers the space and flexibility to create exactly what you need. Saratoga ISP provides reliable connectivity. Despite its peaceful setting, the property is conveniently located just a short drive from local amenities, including shopping, dining, and schools and close enough to enjoy Music in the Gap in Hillsboro, relax at one of the many wineries or breweries, shop at a local organic farm or hike the Appalachian Trail. Whether you're looking for a quiet place to raise a family or a serene retirement home, this property offers the best of both worlds—peaceful country living with easy access to everything you need.

13855 Paris Breeze Pl, Hillsboro

$1,300,000
3 Beds 4 Baths VALO2079138 MLS ACTIVE Status
Get ready to fall head over heels for this captivating 26-acre farm in the heart of Virginia's renowned wine country! Nestled just beyond the charming town of Hillsboro, this property is a true gem, boasting a stunning Federal-style farmhouse dating back to 1812. Adorned with double front porches, mountain and vineyard views, this storybook setting will take your breath away from the moment you arrive. But the magic doesn't stop there! A wooden peg barn, a pond, corn crib, a hand hewn log cabin from the late 1700's and various other structures, offer endless possibilities for your country living dreams. Whether you envision running a thriving agro business from home or simply embracing the tranquility of rural life, this remarkable farm is the perfect canvas to bring your vision to life. Escape the hustle and bustle of city life and immerse yourself in the rich history and natural beauty of this one-of-a-kind property. Don't miss your chance to make this captivating setting your own - come experience the magic of country living in the heart of Loudoun's renowned wine country! Special Features of this Property: Land is 26.15 acre AR1. Land Use status renewed with Loudoun County in 2023. Land is NOT IN EASEMENT New Furnace 2020 25k in new paint work inside+out Stocked pond was re-dug in 1990 New septic system 2018. septic pumped 2023. inspected by county+ new floats installed 2024 Chimneys re-pointed 2018. (3) working fireplaces New 200 amp electric service installed to house in 2017 Pex plumbing pipes installed throughout 2017 25k new well dug 2022. 680’ deep. new water filtration+softener Outbuildings include Bank Barn + Corn Crib + Spring House + Smoke House. New roofs on outbuildings installed 2010 New 200 amp electric service and electricity in Barn -2019 Chestnut hardwood floors throughout main portion of circa 1812 house (not in kitchen) 3 story garage framed in oak with pine hardwood floors + bonus room above and walk out basement New hot water heater 2024 Hand hewn log cabin circa late 1700s- near pond - awaiting restoration - last occupied in the 1940s

12048 Harpers Ferry Rd, Hillsboro

$1,350,000
4 Beds 4 Baths VALO2078144 MLS ACTIVE Status
Stunning Evergreen Homes Build in Longmoor Farm Estates! From sunrise to sunset you will enjoy the beauty of this home, community and Western Loudoun County location! Welcome to this like-new custom-built home by Evergreen Homes, located in the highly sought-after community of Longmoor Farm Estates. This exceptional property is sited on a sprawling 3.01-acre lot, offering panoramic views that are nothing short of breathtaking. Look west and enjoy the Blue Ridge Mountain views and sunset. Built in 2021 by Evergreen Homes, this home shows like new! Open and bright floor plan with light wood flooring on the main level and dual staircase leading to the expansive upper level** Cozy front porch and glass front door will greet you! Enjoy two (2) main level offices or a 5th bedroom on the main level perfect for play, study or guests * Inviting family room with Gas fireplace with Stone surround and coffered ceilings opens to the expansive gourmet kitchen with huge walk-in pantry, 5 burner gas cooktop, dual wall ovens, stainless appliances, which is perfect for every day living and entertaining. The main level features a thoughtfully designed floor plan with numerous builder upgrades that enhance both style and functionality. Enjoy your favorite tunes with the bluetooth surround sound system. The open-concept living spaces are perfect for modern living, with high-end finishes and ample natural light throughout. The upper level boasts a Primary Suite wood flooring, walls of windows, dual walk in closets and luxury bath with double sinks, spacious shower and soaking tub ** 3 generously sized secondary bedrooms with shared bath and ensuite. Custom Shades in all bedrooms ** Laundry stays on the upper level in this beautiful home! The unfinished lower, walkout level with walls of windows provides a blank canvas for you to add your personal touch and create the space of your dreams—whether it’s a home theater, gym, full bath, recreation room or additional living quarters. BONUS -- Custom, lighted Basketball Court for hours of enjoyment during the day and evening hours. 1000 Gallon Propane Tank Owned and served through Valley Energy. With no HOA, you’ll have the freedom to truly make this property your own. Plus, stay connected with Fios Internet Service available at the home, ensuring high-speed connectivity for work or play. Don't miss the opportunity to own this exceptional property in Longmoor Farm Estates!

16508 Hillsboro Rd, Hillsboro

$719,000
3 Beds 3 Baths VALO2077490 MLS ACTIVE Status
Main level living in town! Perched on a gentle hilltop affording spectacular sunrise and sunset views, this classic 4-sides brick 3BR 3BA rancher is perched on 1.2 acres and has been extensively remodeled. New energy star windows throughout, refinished hardwood flooring on main level, new septic, new fencing, new HVAC, new high efficiency wood stove, new whole house humidifier, new interior paint including all trim work, energy efficient lighting, new blinds, new crown molding, updated baths and frameless glass shower doors in all bathrooms, new tankless water heater, motion activated closet lighting, new decorator ceiling fans, lower level expansion to include 3rd full bath, newly finished activities areas with recessed LED lighting, new LVP wood flooring, new high efficiency wood stove & tile surround, built-in book cases, a lighted cedar closet, new wet bar area, new separate laundry area with new washer, dryer & laundry sink. New garage door openers 2023. New roof 2019. Exterior upgrades include new gravel driveway and large parking pad 2024 flanking brick retention walls, new drainage system. Extensive landscaping and extensive hardscaping added in 2023. Good news! Property is scheduled to be connected to public water and sewer in 2024. Existing well may also be used for back up. Historic Hillsboro is a gem of a town offering weekly free concerts in Summer, fireworks in July, and various fun events year round are all just steps away at the Old Stone School. Residents also receive priority status for eligibility to attend the LCPS Hillsboro Charter Academy. House has fast fiber optic internet already installed. Hillsboro is also designated as an Appalachian Trail Community. Conveniently located close to Purcellville, Leesburg, Dulles Greenway, the W&OD Trail and a plethora of wineries and breweries. Come enjoy the Western Loudoun lifestyle that everyone is talking about! Gym equip in garage can convey.

36930 Gaver Mill Rd, Hillsboro

$999,000
3 Beds 2 Baths VALO2070102 MLS ACTIVE Status
Welcome to historic Derry's Tavern. Currently a residence, this AR1 zoned property is a delight to see and experience. A plethora of uses for the 10 AC parcel might include running a business from your home with little to no restrictions with plenty of storage space for commercial vehicles, Rich in history, yet offering the comforts of today's living. Ideal setting for a business operating out of the home, log cabin, or the barn. Every room is spacious with high ceilings and natural light fills the spaces from the large windows. The log cabin is structurally sound and just waiting for your creativity. and is believed to be from the 1780-1790s era. Surprisingly, there is plenty of storage space throughout the home. The original staircase wraps around two fireplaces and is usable, however, we ask that you use the "newer" 1947 one for safety purposes. At the top of the original stairs is the original sleeping quarters with the original wide-plank flooring. The 3rd BR has been updated with newly refinished stained and sanded HDWD flooring. A newer septic drainfield was installed, propane heat & AC added, with most older plumbing & wiring replaced. In 2022, updates include a new roof, exterior paint & some interior paint along with both baths completely redone. The kitchen was modernized in 2005-ish and features pull-out trays in the lower cabinet units, soft close doors and drawers and individual lazy susan turnstiles in the corner cabinets. Granite counter-tops and back-splash make for easy clean-up. In 2023, the microwave , dishwasher, kitchen faucet and washer & dryer were replaced. The terraced flower gardens outside the sunroom window provide a mesmerizing backdrop for the birds, bees, cats, and occasional wildlife visit. The vegetable gardens offer irrigation and high fencing for ease in care & protection from midnight raids by deer. An 35,000 gallon in-ground pool is ready for the summer season and pool equipment has been replaced and updated. This property is such a delight to see with so much that could be written - that a visit is more than worth your time.

35180 Charles Town Pike, Hillsboro

$2,100,000
7 Beds 7 Baths VALO2069316 MLS ACTIVE Status
**PRICE IMPROVEMENT** -- What are you waiting for?! Sellers motivated, and you won't find a better deal on RARE 26.59 ACRES! ESCAPE TO SERENITY: A WESTERN LOUDOUN FARM RETREAT Welcome to your dream home at Longmoor Farm Estates in Purcellville, VA! Nestled on over 26 acres of picturesque countryside, this stunning custom estate offers unparalleled luxury and privacy, surrounded by high-end custom homes on large parcels. As you drive up the long circular driveway, you'll be greeted by the elegance of this stately high-end siding estate. Step through the elegant wooden stained glass front door, and prepare to be amazed by the soaring ceilings and bright floor plan that spans over 8600 square feet across three levels. From sophisticated millwork to brazilin teak hardwood flooring, every detail has been meticulously crafted to create an atmosphere of refined elegance. The family room serves as the centerpiece of the home, with a floor-to-ceiling stone gas-burning fireplace and walls of windows offering breathtaking views and abundant natural light. Work or school from home effortlessly in the sizable library/study with custom cabinetry and Comcast internet available service. Entertaining is a breeze in the gourmet kitchen, featuring top-of-the-line stainless steel appliances, generous cabinetry, and a large window overlooking the expansive 26.59-acre lot. The main level primary suite boasts a large walk-in closet and luxury bath with a jetted tub, providing a tranquil retreat after a long day. With front and rear staircases providing ease of access, friends and family will have plenty of private space in the generously sized bedrooms and baths on the upper levels, as well as a separate media room complete with high-end wood-paneled walls and surround sound. Entertaining continues in the finished lower level, featuring a billiard room, custom bar, and full kitchen with walls of windows flooding the space with natural light. An exercise room can also serve as an additional bedroom with a private bath, perfect for extended family, au pairs, or guests. However, they may prefer to stay in the attached studio apartment where you also have the option for a farm sitter. Outside, the custom landscaping adds to the allure of the property, while the 4-stall barn with a tack room and riding ring/paddock make it perfect for horse lovers. The lot is ideal for outdoor activities and potential pool installation, with 3-board blackboard fencing offering both functionality and charm. With NO HOA and Comcast high-speed internet service available, this is country living at its finest, with all the modern conveniences you could desire. Recent 2021 improvements include an 18k generator, trim paint & repair, paved driveway, new appliances, new AC units, and carpet. Don't miss your chance to make this move-in ready estate your private oasis just miles from the towns of Middleburg and Purcellville in the Loudoun County School District, zoned for Mt. View Elementary, Harmony Middle, and Woodgrove High School. -- Come experience the lifestyle you've always dreamed of!

37016 Longmoor Farm Ln, Hillsboro

$2,100,000
7 Beds 7 Baths VALO2065950 MLS ACTIVE Status
**PRICE IMPROVEMENT** -- This is it folks... Sellers motivated, and you won't find a better deal on RARE 26.59 ACRES! ESCAPE TO SERENITY: A WESTERN LOUDOUN FARM RETREAT Welcome to your dream home at Longmoor Farm Estates in Purcellville, VA! Nestled on over 26 acres of picturesque countryside, this stunning custom estate offers unparalleled luxury and privacy, surrounded by high-end custom homes on large parcels. As you drive up the long circular driveway, you'll be greeted by the elegance of this stately high-end siding estate. Step through the elegant wooden stained glass front door, and prepare to be amazed by the soaring ceilings and bright floor plan that spans over 8600 square feet across three levels. From sophisticated millwork to brazilin teak hardwood flooring, every detail has been meticulously crafted to create an atmosphere of refined elegance. The family room serves as the centerpiece of the home, with a floor-to-ceiling stone gas-burning fireplace and walls of windows offering breathtaking views and abundant natural light. Work or school from home effortlessly in the sizable library/study with custom cabinetry and Comcast internet available service. Entertaining is a breeze in the gourmet kitchen, featuring top-of-the-line stainless steel appliances, generous cabinetry, and a large window overlooking the expansive 26.59-acre lot. The main level primary suite boasts a large walk-in closet and luxury bath with a jetted tub, providing a tranquil retreat after a long day. With front and rear staircases providing ease of access, friends and family will have plenty of private space in the generously sized bedrooms and baths on the upper levels, as well as a separate media room complete with high-end wood-paneled walls and surround sound. Entertaining continues in the finished lower level, featuring a billiard room, custom bar, and full kitchen with walls of windows flooding the space with natural light. An exercise room can also serve as an additional bedroom with a private bath, perfect for extended family, au pairs, or guests. However, they may prefer to stay in the attached studio apartment where you also have the option for a farm sitter. Outside, the custom landscaping adds to the allure of the property, while the 4-stall barn with a tack room and riding ring/paddock make it perfect for horse lovers. The lot is ideal for outdoor activities and potential pool installation, with 3-board blackboard fencing offering both functionality and charm. With NO HOA and Comcast high-speed internet service available, this is country living at its finest, with all the modern conveniences you could desire. Recent 2021 improvements include an 18k generator, trim paint & repair, paved driveway, new appliances, new AC units, and carpet. Don't miss your chance to make this move-in ready estate your private oasis just miles from the towns of Middleburg and Purcellville in the Loudoun County School District, zoned for Mt. View Elementary, Harmony Middle, and Woodgrove High School. -- Come experience the lifestyle you've always dreamed of!

37016 Longmoor Farm Ln, Hillsboro

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