The latest in luxury property, lifestyle & culture, curated just for you.

  • California
  • Colorado
  • Connecticut
  • Florida
  • Massachusetts
  • Mid-Atlantic
  • Nevada
  • New Jersey
  • New York
  • New York City
  • Texas
  • Vermont

  • California
  • Colorado
  • Connecticut
  • Florida
  • Massachusetts
  • Mid-Atlantic
  • Nevada
  • New Jersey
  • New York
  • New York City
  • Texas
  • Vermont

  • California
  • Colorado
  • Connecticut
  • Florida
  • Massachusetts
  • Mid-Atlantic
  • Nevada
  • New Jersey
  • New York
  • New York City
  • Texas
  • Vermont

  • California
  • Colorado
  • Connecticut
  • Florida
  • Massachusetts
  • Mid-Atlantic
  • Nevada
  • New Jersey
  • New York
  • New York City
  • Texas
  • Vermont
  • Site Map
  • Terms
  • Privacy
  • Cookie Preferences
  • Do Not Sell or Share My Personal Information
  • NYS Housing Discrimination Disclosure Notice & Form
  • NYS Standard Operating Procedure
  • NYS Tenants' Rights to Reasonable Accommodations for persons with disabilities
  • California Consumer Privacy Act Notice
  • Texas Consumer Protection Notice
  • Texas Real Estate Commission Information About Brokerage Services
  • Text of NYC Human Rights Law
  • New York City Commission on Human Rights
  • NYC Source of Income Discrimination Information
  • NYC Source of Income Discrimination Tenant FAQs

THE SOURCE OF THE DISPLAYED DATA IS EITHER THE PROPERTY OWNER OR PUBLIC RECORD PROVIDED BY NON-GOVERNMENTAL THIRD PARTIES. IT IS BELIEVED TO BE RELIABLE BUT NOT GUARANTEED. FOR COLORADO VIEWERS, INFORMATION ABOUT NON-COMMERCIAL PROPERTIES IS PROVIDED EXCLUSIVELY FOR YOUR PERSONAL, NON-COMMERCIAL USE.

575 MADISON AVENUE, NEW YORK, NY 10022. 212.891.7000 © 2026 DOUGLAS ELLIMAN REAL ESTATE. EQUAL EMPLOYMENT OPPORTUNITY PROVIDER. ALL MATERIAL PRESENTED HEREIN IS INTENDED FOR INFORMATION PURPOSES ONLY. WHILE THIS INFORMATION IS BELIEVED TO BE CORRECT, IT IS REPRESENTED SUBJECT TO ERRORS, OMISSIONS, CHANGES, OR WITHDRAWAL WITHOUT NOTICE. ALL PROPERTY INFORMATION, INCLUDING, BUT NOT LIMITED TO SQUARE FOOTAGE, ROOM COUNT, NUMBER OF BEDROOMS, AND THE SCHOOL DISTRICT IN PROPERTY LISTINGS SHOULD BE VERIFIED BY YOUR OWN ATTORNEY, ARCHITECT, OR ZONING EXPERT. EQUAL HOUSING OPPORTUNITY. LISTING DATA REFRESHED ON MAR 19 2026 AT 8:18 AM.

DOUGLAS ELLIMAN IS A LICENSED REAL ESTATE BROKER IN CALIFORNIA WITH LICENSE # 01947727, COLORADO WITH LICENSE # EC100053892, CONNECTICUT WITH LICENSE # REB.0314827, THE DISTRICT OF COLUMBIA WITH LICENSE # REO40000160, FLORIDA WITH LICENSE # CQ1020232, MARYLAND WITH LICENSE # 645270, MASSACHUSETTS WITH LICENSE # 422764, NEVADA WITH LICENSE # 1454643, NEW JERSEY WITH LICENSE # 0572105, NEW YORK WITH LICENSE # 10991211812, TEXAS WITH LICENSE # 9008706, AND VIRGINIA WITH LICENSE # 0226035659.

SCAMMERS ARE IMPERSONATING REAL ESTATE AGENTS AND USING ACTIVE LISTINGS TO REQUEST FAKE DEPOSITS. SHOULD YOU HAVE A QUESTION ABOUT THE LEGITIMACY OF A DOUGLAS ELLIMAN AGENT OR LISTING, PLEASE CONTACT THE AGENT DIRECTLY VIA THE “AGENTS” LINK IN THE TOP MENU. DOUGLAS ELLIMAN WILL NEVER ASK FOR ANY PAYMENT TO RESERVE, HOLD, OR VIEW A PROPERTY. THESE CHARGES ARE PROHIBITED UNDER NEW YORK LAW. IF YOU RECEIVE A SUSPICIOUS REQUEST FOR MONEY, DO NOT SEND FUNDS. REPORT IT TO THE NYS DEPARTMENT OF STATE AND NOTIFY DOUGLAS ELLIMAN. YOU CAN READ THE NEW YORK STATE DEPARTMENT OF STATE'S CONSUMER ALERT HERE.

POWERED BY PURLIN.AI

38793 CHELTEN Ln

middleburg, VA 20117

$5,500,000

  • 5 BR
    8 BA, 2 HALF BA
    approx. 16,667 SF

Interested? Let's Connect

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.

Details

16,667 Sq Ft

30 Private Acres Lot Size

other

$32,173 Annual Tax

Built in 2003

MLS/Listing ID VALO2094274

Amenities & Features

Refrigerator

Instant Hot Water

Dryer

Disposal

Dishwasher

Style - Mediterranean

Hardwood

Stone

Wood

Cooling - Ceiling Fans

Cooling - Central Air

Construction - Stone

Construction - Stucco

Slate

Metal

Lot - Mountainous

Ceiling Fans

Pool - Inground

Pool Spa Combo

Lot - Private

Washer

Dining Area

Intercom

Pantry

Recessed Lighting

Walk-in Closets

Window Treatments

Carpet

Estimate my mortgage

TOTAL MONTHLY COST

$0

  • PRINCIPAL & INTEREST

    $0

  • PROPERTY TAXES

    $0

  • Common Charges

    $0

HOME PRICE
DOWN PAYMENT
TERM
INTEREST

Interested In 38793 CHELTEN Ln?

The data relating to the real estate for sale on this web site comes in part from the Internet Data Exchange Program of the BrightMLS. Real estate listings held by brokerage firms other than Douglas Elliman of VA are marked with the Internet Data Exchange logo and information about them includes the name of the listing brokers. Some properties listed with the participating brokers do not appear on this website at the request of the seller. Listings of brokers that do not participate in Internet Data Exchange do not appear on this website.

All information deemed reliable but not guaranteed. Last date updated: 03/19/2026.
Source: Bright Multiple Listing Service, Inc.

© 2026 Bright Multiple Listing Service, Inc. All rights reserved.