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38793 Chelten Ln, 
Middleburg, VA 20117

$5,500,000


5

Beds


10

Baths


16,667

Sq Ft


Single Family

Active

Listed by

Jenna Marie Gallant

Ttr Sotheby'S International Realty

Last updated:

January 6, 2026, 02:33 AM

MLS#

VALO2094274

Source:

BRIGHTMLS

About This Home

38793 Chelten Ln

Perched majestically in Virginia's prestigious Hunt Country, "The Looking Glass" estate offers an unparalleled living experience across 30 breathtaking acres. Named for its sweeping panoramic views of the mountains and neighboring vineyard, this Tuscan-inspired masterpiece seamlessly blends old-world charm with modern luxury. The magnificent main residence spans 17,000 square feet, with 11,000 square feet of meticulously designed living space on the first two levels and an additional 6,000 square feet on the lower level with room for further customization. Featuring five sumptuous bedrooms and ten elegant bathrooms, the estate creates an atmosphere of refined opulence through its exceptional construction and meticulous maintenance. The exterior showcases a harmonious blend of stone and stucco, complemented by distinctive arched doorways and windows that define its architectural character. Inside, rich hardwood, natural stone, and luxurious marble flooring extend throughout, while wrought iron staircases add to the estate's old-world ambiance. Outdoor entertaining reaches new heights with a heated pool and spa adjacent to an inviting pavilion featuring a stone terrace and outdoor fireplace—all overlooking the estate's stunning grounds and breathtaking vistas. The property is further enhanced by a spacious 2,500-square-foot guest house offering four bedrooms, generous living spaces, and a full kitchen. Equestrian enthusiasts will appreciate the connecting eight-stall stable with its grand ceiling, convenient wash stall, and well-appointed tack room. "The Looking Glass" represents an extraordinary opportunity to own one of Hunt Country's most distinguished estates.

Home Facts

Single Family

10 Baths

5 Bedrooms

Built in 2003

Price Summary

5,500,000

$329 per Sq. Ft.

MLS #:

VALO2094274

Last Updated:

January 6, 2026, 02:33 AM

Added:

7 month(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

5

Bathrooms

Total Bathrooms:

10

Full Bathrooms:

8

Interior

Living Area:

16,667 Sq. Ft.


Structure

Structure

Architectural Style:

Mediterranean

Building Area:

16,667 Sq. Ft.

Year Built:

2003


Lot

Lot Size (Sq. Ft):

1,306,800


Finances & Disclosures

Finances

Price:

$5,500,000

Price per Sq. Ft:

$329 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.