36279 & 36285 E Loudoun St, Round Hill, VA 20141
Local realty services provided by:Better Homes and Gardens Real Estate Valley Partners
Listed by: paul e. macmahon, helen e macmahon
Office: sheridan-macmahon ltd.
MLS#:VALO2124302
Source:BRIGHTMLS
Price summary
- Price:$5,500,000
- Price per sq. ft.:$1,384.69
About this home
Greystone
A truly exceptional offering, Greystone stands as a rare and storied estate, held within the same family for over a century and gracefully positioned atop one of Loudoun County’s most captivating hilltop settings. From its commanding vantage point, the property enjoys sweeping, cinematic views across the rolling Virginia countryside to the distant Blue Ridge Mountains—an ever-shifting panorama of light, sky, and season.
A long, paved, tree-lined approach sets the tone, rising gently to reveal the residence—an elegant stone and frame home of enduring character and quiet distinction. Rooted in history yet timeless in appeal, the home unfolds with a sense of warmth and understated grandeur. Inside, exposed beams, and beautifully aged heart pine floors are complemented by three fireplaces and an abundance of natural light, creating interiors that are both refined and deeply inviting. Expansive windows frame the surrounding landscape, bringing the outside in at every turn.
The residence offers five bedrooms and three and a half baths, with thoughtfully updated kitchen and baths that honor the home’s architectural heritage while providing modern comfort and ease.
Greystone lives as a true country estate, where the supporting structures are as compelling as the main residence. A charming guest house, complete with two bedrooms, two baths, and its own detached garage, offers a private and welcoming retreat. The grounds further feature a detached two-car garage, a swimming pool nestled within mature landscaping, a large garden shed, and the quiet remnants of a former tennis court—subtle traces of a bygone era of country leisure.
The land itself is remarkable—gently rolling, framed by mature trees and established plantings, and offering both beauty and versatility. Comprising three separate parcels, totaling 78.17 acres with frontage on both sides of East Loudoun Street, the property presents a rare opportunity for stewardship, expansion, or thoughtful future use. Two parcels are currently enrolled in land use, with crop rights in place.
Greystone is more than a residence; it is a legacy—an opportunity to own a piece of Loudoun County’s history, defined by its extraordinary setting, timeless architecture, and enduring sense of place. Properties of this caliber, offering such provenance, scale, and views, seldom come to market.
Zoned AR1. Offered "AS IS"....
Contact an agent
Home facts
- Year built:1910
- Listing ID #:VALO2124302
- Added:56 day(s) ago
- Updated:June 30, 2026 at 09:08 AM
Rooms and interior
- Bedrooms:5
- Total bathrooms:4
- Full bathrooms:3
- Half bathrooms:1
- Flooring:Hardwood, Tile/Brick
- Dining Description:Dining Area, Dining Room
- Bathrooms Description:Primary Bath(s)
- Kitchen Description:Breakfast Area, Built-Ins, Cooktop, Dishwasher, Disposal, Exhaust Fan, Kitchen - Eat-In, Kitchen - Gourmet, Kitchen - Table Space, Microwave, Oven - Wall, Refrigerator, Upgraded Countertops, Wet/Dry Bar
- Bedroom Description:Entry Level Bedroom, Primary Bedroom
- Basement:Yes
- Basement Description:Interior Access, Outside Entrance, Rear Entrance, Unfinished
- Living area:3,972 sq. ft.
Heating and cooling
- Cooling:Ceiling Fan(s), Central A/C, Zoned
- Heating:Electric, Forced Air, Heat Pump(s), Oil
Structure and exterior
- Roof:Architectural Shingle, Slate
- Year built:1910
- Building area:3,972 sq. ft.
- Lot area:78.17 Acres
- Lot Features:Adjoins - Public Land, Backs to Trees, Crops Reserved, Front Yard, Landscaping, Level, No Thru Street, Not In Development, Partly Wooded, Poolside, Private, Rear Yard, Road Frontage, Rural, Secluded, SideYard(s), Subdivision Possible, Trees/Wooded
- Architectural Style:Colonial
- Construction Materials:Stone, Wood Siding
- Exterior Features:Outbuilding(s), Play Area, Porch(es), Screened, Sidewalks, Tennis Court(s)
- Foundation Description:Stone
- Levels:4 Story
Utilities
- Water:Well
Finances and disclosures
- Price:$5,500,000
- Price per sq. ft.:$1,384.69
- Tax amount:$10,913 (2026)
Features and amenities
- Laundry features:Dryer, Washer
- Amenities:200+ Amp Service, Attic, Built-Ins, Ceiling Fan(s), Exposed Beams, Wet/Dry Bar
- Pool features:Gunite, In Ground
Parking
- Parking description:Additional Storage Area, Asphalt Driveway, Circular Driveway, Detached Garage, Garage - Front Entry
- Garage:Yes
- Garage spaces:2
New listings near 36279 & 36285 E Loudoun St
- Coming Soon
$1,299,999Coming Soon4 beds 5 baths19725 Woodtrail Rd, ROUND HILL, VA 20141
MLS# VALO2129816Listed by: THOMAS AND TALBOT ESTATE PROPERTIES, INC. - New
$999,999Active4 beds 4 baths3,300 sq. ft.17951 Stoneleigh Dr, ROUND HILL, VA 20141
MLS# VALO2129186Listed by: SAMSON PROPERTIES - New
$1,599,000Active6 beds 5 baths5,750 sq. ft.35443 Glencoe Ct, ROUND HILL, VA 20141
MLS# VALO2128892Listed by: BERKSHIRE HATHAWAY HOMESERVICES PENFED REALTY 
$749,900Active4 beds 4 baths3,138 sq. ft.17292 Magic Mountain Dr, ROUND HILL, VA 20141
MLS# VALO2128758Listed by: LONG & FOSTER REAL ESTATE, INC.
$709,500Active4 beds 3 baths2,050 sq. ft.35094 Scotland Heights Rd, ROUND HILL, VA 20141
MLS# VALO2128356Listed by: CORCORAN MCENEARNEY
$1,199,900Pending5 beds 4 baths4,017 sq. ft.35054 Mcknight Ct, ROUND HILL, VA 20141
MLS# VALO2128240Listed by: KW METRO CENTER
$1,369,000Pending4 beds 6 baths5,074 sq. ft.17780 Stoneleigh Dr, ROUND HILL, VA 20141
MLS# VALO2127860Listed by: NOVA HOME HUNTERS REALTY
$795,000Active4 beds 3 baths2,510 sq. ft.35529 Hudson St, ROUND HILL, VA 20141
MLS# VALO2126944Listed by: ON THE MARKET PROPERTIES
$1,250,000Pending6 beds 5 baths5,819 sq. ft.34905 Gidney Ct, ROUND HILL, VA 20141
MLS# VALO2126786Listed by: KELLER WILLIAMS REALTY
$719,000Pending4 beds 4 baths2,647 sq. ft.17551 Lethridge Cir, ROUND HILL, VA 20141
MLS# VALO2127486Listed by: SAMSON PROPERTIES
Protect your home and budget from life's surprises with an Assurant Home Warranty, backed by a partner that supports you through every step of homeownership. Explore Plans.
© 2026 Better Homes and Gardens Real Estate LLC. An Anywhere Real Estate company. All rights reserved. Better Homes and Gardens® Real Estate is a registered trademark owned by Meredith Operations Corporation, licensed to Better Homes and Gardens Real Estate LLC and used with permission. Better Homes and Gardens Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Listing information is deemed reliable but is not guaranteed accurate.
Each office is independently owned and operated.
Any services or products provided by third parties are not provided by, affiliated with or related to Better Homes and Gardens Real Estate LLC, or its affiliated companies.