Tucked into the rolling countryside of Western Loudoun, 20919 Watermill Road feels like something out of a storybook—where winding roads lead to hidden gems and every season paints a new masterpiece across the landscape. Set on nearly four picturesque acres, this enchanting property offers the rare blend of charm, privacy, and convenience, perfectly positioned between downtown Purcellville and historic Middleburg—bringing the best of both worlds right to your doorstep. From the moment you arrive, the setting captures your imagination. Panoramic views stretch across the countryside, while a gentle creek winds its way through the property, creating a peaceful backdrop for everyday living. The land itself is a dream—complete with a fenced backyard, a charming shed, and flourishing cherry and apple trees that offer both beauty and bounty throughout the seasons. Just down the road, you’ll find the beloved Philomont General Store and the heart of the community at the Philomont Community Center, adding to the sense of connection and small-town charm that makes this location so special. Inside, the home has been completely updated and is truly move-in ready, blending modern comfort with timeless character. With 4 bedrooms and 2.5 baths, the layout offers both functionality and warmth. There’s a quiet elegance here—reminiscent of a European countryside retreat—where cozy moments and effortless living come naturally. Whether you envision it as a full-time residence, a dreamy weekend escape near Middleburg’s vineyards and horse country, a charming Airbnb, or a smart long-term rental investment, the possibilities are as expansive as the views. And with a price point comparable to a townhouse, this property presents a rare opportunity to own a slice of Loudoun County’s most idyllic landscape. 20919 Watermill Road isn’t just a home—it’s a lifestyle, a retreat, and a place where everyday life feels just a little more magical. For those dreaming of turning this property into a short-term rental, the opportunity here is compelling. With its sought-after location, inviting layout, and strong regional demand, this home is well-positioned to perform. Third-party data suggests potential gross annual revenue between $45,000 and $85,000, depending on seasonality, occupancy, and management style. While performance is not guaranteed, the numbers paint an exciting picture for buyers looking to blend lifestyle and income. Buyers should verify local regulations, permitting, and financials. RECENT UPDATES INCLUDE: Interior Painting (2025), Stair Carpet (2025), Exterior Painting (2024), First Floor Flooring (2023), HVAC Condenser, Coil Unit and Blower (2022), Water Heater (2022), Dishwasher & Oven (2022), Windows (2020), 50 Year Life Roof (2008), & more!
Est. $3,877 per month, based on comparable rentals
Sale and tax history for 20919 Watermill Rd
Sale History
Tax History
Date
Event
Price
BRIGHT MLS #VALO2120774
Jun 2, 2026
Sold
$750,000
$329/sq ft
May 14, 2026
Pending
—
Apr 27, 2026
Contingent
—
Apr 23, 2026
Price Changed
$750,000
$329/sq ft
Apr 8, 2026
Listed
$775,000
$340/sq ft
BRIGHT MLS #VALO2112414
Mar 26, 2026
Listing Removed
—
Feb 21, 2026
Contingent
—
Feb 16, 2026
Price Changed
$774,900
$340/sq ft
Feb 4, 2026
Price Changed
$799,900
$351/sq ft
Jan 14, 2026
Listed
$824,900
$362/sq ft
Jan 10, 2026
Coming Soon
*
Public Records
Jan 8, 2021
Sold
$585,000
$257/sq ft
BRIGHT MLS #VALO425152
Jan 8, 2021
Listing Removed
—
Jan 7, 2021
Sold
$585,000
$257/sq ft
Jan 6, 2021
Pending
—
Dec 13, 2020
Contingent
—
Dec 8, 2020
Price Changed
$575,000
$252/sq ft
Nov 19, 2020
Listed
$600,000
$263/sq ft
+32
Beautiful 4Bed 2.5Bath remodeled single family home. The land--sits on "Birdsong Hill", rolling 3.8 acres overlooking a quiet stream and has amazing views from every room in the house!! Want more privacy, your backyard backs to cow pastures. Front yard is an orchard. .. .9 apple trees, 2 pear trees, 2 tart cherry trees Amenities-- Gigabyte Internet access. Two previous owners were IT professionals, calling this beautiful place home and office. Minutes from several wineries. Paintball park. Equestrian Farms. Large Shed in property. 240V generator interlock for power in case of emergency. The Home -- * Energy Efficiency galore: Structural Shingle Roof with limited lifetime warranty. All Windows Replaced in 2020 with lifetime warranty, even for accidentals. High Efficiency Anderson Exterior Doors Geothermal Heating/Cooling and Water Heater Wifi enabled thermostat/stove/washer/dryer Aesthetic Highlights-- Hardwood flooring throughout the main level. Kitchen boasts stainless steel appliances, resurfaced cabinets with elegant white color, butcher island. Master bed/bath has been completely remodeled. New modern double vanities, designer inspired tile work and frameless glass shower door, new light fixtures and bluetooth speaker exhaust fan! Location-6 miles NE of Middleburg & convenient to Town of Purcellville & Chantilly.
The purpose and intent of the Agricultural Rural-1 Zoning District is to: Implement the Rural North Place Type of the General Plan; Preserve and protect Prime Farmland Soils, recognizing their importance to the agricultural community and overall economic health of the rural economy; Support the use of land that protects, preserves and enhances natural areas and open space, retains farmland, and the vitality of the rural economy, and fosters a high quality of life for residents; Ensure complimentary rural economy uses, including traditional and new agricultural uses, agriculture support and basic services directly associated with on-going agricultural activities, and other uses can be developed in ways that are consistent with the rural character of and are compatible with existing residential development in the AR-1 Zoning District through mitigation or other standards; Recognize the County’s tourism industry is interconnected with the rural economy and rural economy uses in the AR-1 Zoning District by allowing for tourism uses related to agricultural uses, public, civic, and institutional uses; rural activity, and special event uses; Limit residential development to densities that will protect the land resources for agricultural operations, common open space uses, and rural economy uses; Promote consistency between residential development and rural economy uses through lower density residential development or the clustering of residential development and Ensure development incorporates natural, environmental, and heritage resources while preserving important viewsheds that contribute to the rural landscape.