38793 Chelten Ln, Middleburg, VA 20117
Local realty services provided by:CENTURY 21 Alliance
38793 Chelten Ln,Middleburg, VA 20117
$4,995,000
- 5 Beds
- 10 Baths
- 16,667 sq. ft.
- Single family
- Active
Listed by: jenna marie gallant
Office: ttr sotheby's international realty
MLS#:VALO2094274
Source:BRIGHTMLS
Price summary
- Price:$4,995,000
- Price per sq. ft.:$299.69
About this home
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....
Contact an agent
Home facts
- Year built:2003
- Listing ID #:VALO2094274
- Added:405 day(s) ago
- Updated:June 16, 2026 at 01:50 PM
Rooms and interior
- Bedrooms:5
- Total bathrooms:10
- Full bathrooms:8
- Half bathrooms:2
- Flooring:Carpet, Hardwood, Heated, Stone, Tile/Brick
- Dining Description:Combination Dining/Living, Dining Area, Formal/Separate Dining Room
- Bathrooms Description:Primary Bath(s), WhirlPool/HotTub
- Kitchen Description:Breakfast Area, Built-Ins, Carpet, Dishwasher, Disposal, Extra Refrigerator/Freezer, Instant Hot Water, Kitchen - Gourmet, Oven/Range - Gas, Pantry, Recessed Lighting, Refrigerator, Stainless Steel Appliances, Stove
- Bedroom Description:Carpet, Entry Level Bedroom, Walk In Closet(s)
- Basement:Yes
- Basement Description:Partially Finished, Walkout Level, Windows
- Living area:16,667 sq. ft.
Heating and cooling
- Cooling:Ceiling Fan(s), Central A/C
- Heating:Heat Pump(s), Propane - Leased, Zoned
Structure and exterior
- Roof:Metal, Slate
- Year built:2003
- Building area:16,667 sq. ft.
- Lot area:30 Acres
- Lot Features:Backs to Trees, Landscaping, Mountainous, Private
- Architectural Style:Mediterranean
- Construction Materials:Stone, Stucco
- Exterior Features:Balconies- Multiple, Extensive Hardscape, Patio(s)
- Levels:3 Story
Schools
- High school:JOHN CHAMPE
- Middle school:MERCER
- Elementary school:ALDIE
Utilities
- Water:Well
- Sewer:Private Sewer
Finances and disclosures
- Price:$4,995,000
- Price per sq. ft.:$299.69
- Tax amount:$32,173 (2025)
Features and amenities
- Laundry features:Dryer, Dryer - Gas, Dryer In Unit, Has Laundry, Washer, Washer In Unit
- Amenities:Built-Ins, Cable TV, Carpet, Ceiling Fan(s), Curved Staircase, Efficiency, Intercom, Recessed Lighting, Window Treatments
- Pool features:In Ground, Pool/Spa Combo
Parking
- Parking description:Additional Storage Area, Attached Garage, Detached Garage, Garage Door Opener, Oversized, Paved Driveway
- Garage:Yes
- Garage spaces:5
New listings near 38793 Chelten Ln
- New
$1,825,000Active4 beds 5 baths4,874 sq. ft.21185 St Louis Rd, MIDDLEBURG, VA 20117
MLS# VALO2128316Listed by: THOMAS AND TALBOT ESTATE PROPERTIES, INC. - New
$1,395,000Active3 beds 3 baths2,792 sq. ft.36006 Little River Turnpike, MIDDLEBURG, VA 20117
MLS# VALO2128060Listed by: THOMAS AND TALBOT ESTATE PROPERTIES, INC. 
$2,850,000Active4 beds 5 baths4,499 sq. ft.36190 Turkey Roost Rd, MIDDLEBURG, VA 20117
MLS# VALO2126154Listed by: THOMAS AND TALBOT ESTATE PROPERTIES, INC.
$1,950,000Active3 beds 2 baths3,956 sq. ft.406 E Washington St, MIDDLEBURG, VA 20117
MLS# VALO2126668Listed by: THOMAS AND TALBOT ESTATE PROPERTIES, INC.
$1,525,000Active4 beds 5 baths3,365 sq. ft.37143 Adams Green Ln, MIDDLEBURG, VA 20117
MLS# VALO2126322Listed by: THOMAS AND TALBOT ESTATE PROPERTIES, INC.
$1,495,000Active4 beds 4 baths4,158 sq. ft.12 Orange Dr, MIDDLEBURG, VA 20117
MLS# VALO2125854Listed by: HUNT COUNTRY SOTHEBY'S INTERNATIONAL REALTY
$750,000Active4 beds 3 baths2,490 sq. ft.22202 Newlin Mill Rd, MIDDLEBURG, VA 20117
MLS# VALO2126344Listed by: PAUL WESLEY REAL ESTATE
$2,999,999Active3 beds 3 baths2,946 sq. ft.34520 Atoka Chase Ln, MIDDLEBURG, VA 20117
MLS# VALO2126254Listed by: WASHINGTON FINE PROPERTIES, LLC
$1,849,000Pending3 beds 4 baths3,825 sq. ft.22065 Whitetail Ridge Ln, MIDDLEBURG, VA 20117
MLS# VALO2125122Listed by: WASHINGTON FINE PROPERTIES, LLC
$1,300,000Pending3 beds 4 baths3,250 sq. ft.23357 Wildwood Ln, MIDDLEBURG, VA 20117
MLS# VALO2121878Listed by: PEARSON SMITH REALTY, LLC
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 Century 21 Real Estate LLC. All rights reserved. CENTURY 21®, the CENTURY 21 Logo and C21® are service marks owned by Century 21 Real Estate LLC. Century 21 Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Each office is independently owned and operated. Listing information is deemed reliable but not guaranteed accurate.