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36279 & 36285 E Loudoun St, 
Round Hill, VA 20141

$5,500,000


5

Beds


4

Baths


3,972

Sq Ft


Single Family


Virtual Tour

Pending

Listed by

Paul E. Macmahon

Helen E Macmahon

Sheridan-Macmahon Ltd.

Last updated:

July 8, 2026, 08:06 AM

MLS#

VALO2124302

Source:

BRIGHTMLS

About This Home

36279 & 36285 E Loudoun St

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".

Home Facts

Single Family

4 Baths

5 Bedrooms

Built in 1910

Price Summary

5,500,000

$1,384 per Sq. Ft.

MLS #:

VALO2124302

Last Updated:

July 8, 2026, 08:06 AM

Added:

2 month(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

5

Bathrooms

Total Bathrooms:

4

Full Bathrooms:

3

Interior

Living Area:

3,972 Sq. Ft.


Structure

Structure

Architectural Style:

Colonial

Building Area:

3,972 Sq. Ft.

Year Built:

1910


Lot

Lot Size (Sq. Ft):

3,405,085


Finances & Disclosures

Finances

Price:

$5,500,000

Price per Sq. Ft:

$1,384 per Sq. Ft.

Source:BRIGHTMLS
The information being provided by Bright Mls is for the consumer’s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The information is deemed reliable but not guaranteed and should therefore be independently verified. © 2026 Bright Mls All rights reserved.

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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.