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  • 377 Old Winchester Rd. Boyce VA 22620

5850 Upton Street, MCLEAN, VA 22101 (MLS # VAFX2297168)

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Realtor Matthew Wahlstrom
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PRICE $4,495,000 dsIDX morgage calculator
BEDS 6
BATHS 8
HOME SIZE 8,223 sqft
LOT SIZE 16,989 sqft
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Located in the highly sought-after Chesterbrook Estates neighborhood, this exceptional residence by MR Custom Homes offers a rare blend of luxury, scale, and thoughtful design. Sited on a desirable 17,109 sq. ft. lot on a dead-end street, the home features over 8,223 finished sq. ft. of beautifully appointed living space with ELEVATOR SHAFT rough-in and 3 CAR GARAGE . Inside, an expansive dining room with dramatic wainscoting and oversized windows sets an elegant tone, complemented by a private library ideal for a home office and a sun-filled family room designed for comfortable everyday living and effortless entertaining. The gourmet kitchen is a true centerpiece, featuring high-end appliances, custom cabinetry, and generous prep and gathering space, seamlessly connecting to the breakfast area, screened porch, and expansive flagstone patio for exceptional indoor-outdoor living. A main-level bedroom with a full en-suite bath provides ideal accommodations for guests or multigenerational living, while a dedicated wine room adds a refined touch for both entertaining and storage. Upstairs, the luxurious primary suite serves as a private retreat with dual walk-in closets, a private office, and a spa-like bath. Three additional spacious bedrooms each offer en-suite baths. The lower level is designed for both relaxation and recreation, featuring a large recreation room with a full wet bar, an exercise room, and an additional bedroom with a full en-suite bath"”perfect for an au pair or extended-stay guests"”along with abundant storage. A rare highlight is the combination of a two-car garage plus an additional one-car garage, offering ample parking and storage. Ideally located near major commuter routes, shopping and dining. Only 1 traffic light to cross the Chain Bridge into DC! Chesterbrook ES, Longfellow MS, McLean HS.

DAYS ON MARKET 1 LAST UPDATED 5/4/2026
TRACT CHESTERBROOK ESTATES YEAR BUILT 2026
GARAGE SPACES 3.0 COUNTY FAIRFAX
STATUS Active PROPERTY TYPE(S) Single Family

SCHOOLS
School District FAIRFAX COUNTY PUBLIC SCHOOLS
Elementary School CHESTERBROOK
Jr. High School LONGFELLOW
High School MCLEAN


ADDITIONAL DETAILS
AIR Ceiling Fan(s), Central Air, Electric, Multi Units, Zoned
AIR CONDITIONING Yes
APPLIANCES Built-In Range, Cooktop, Dishwasher, Disposal, Double Oven, ENERGY STAR Qualified Appliances, ENERGY STAR Qualified Water Heater, Gas Oven, Gas Range, Gas Water Heater, Humidifier, Ice Maker, Microwave, Oven, Range, Range Hood, Refrigerator, Stainless Steel Appliance(s)
BASEMENT Exterior Entry, Finished, Full, Interior Entry, Sump Pump, Walk-Out Access, Yes
CONSTRUCTION Brick, HardiPlank Type
EXTERIOR Lighting
FIREPLACE Yes
GARAGE Yes
HEAT Central, Forced Air, Natural Gas, Zoned
INTERIOR Bar, Built-in Features, Ceiling Fan(s), Crown Molding, Eat-in Kitchen, Elevator, High Ceilings, Kitchen Island, Open Floorplan, Pantry, Recessed Lighting, Soaking Tub, Tray Ceiling(s), Walk-in Closet(s)
LOT 0.39 acre(s)
LOT DESCRIPTION Back Yard, Cul-de-sac, Front Yard
PARKING Garage Door Opener, On Street, Garage, Driveway, Basement, Inside Entrance, Attached
POOL DESCRIPTION None
SEWER Public Sewer
STORIES 3+
STYLE Transitional
SUBDIVISION CHESTERBROOK ESTATES
TAXES 26242
VIEW Yes
VIEW DESCRIPTION Garden
WATER Public
MORTGAGE CALCULATOR
   

TOTAL MONTHLY PAYMENT

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CONTACT US ABOUT 5850 UPTON STREET
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Listing provided by Keller Williams Realty
The multiple listing data appearing on this website, or contained in reports produced therefrom, comes in part from Metropolitan Regional Information Systems ("MRIS"). The information provided is for the viewer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties the viewer may be interested in purchasing. All real estate listings include detailed information about them that includes the name of the listing brokers and therefore may reference real estate listing(s) held by a brokerage other than the broker and/or agent who owns this web site.

All listing data, including, but not limited to, square footage and lot size is believed to be accurate, but the listing agent, listing broker and respective Multiple Listing Services and their affiliates do not warrant or guarantee such accuracy. Therefore, all data should be personally verified through personal inspection by and/or with the appropriate professionals. Listing data last updated 5/5/26 5:59 AM PDT.

The listing information on this web site is from various brokers who participate in IDX.

Copyright 2026 MRIS. All rights reserved.

This IDX solution is (c) Diverse Solutions 2026.

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MJ HOME SALES – Better Service. Better Real Estate

Pearson Smith Realty  |  43777 Central Station Drive, #Suite 390, Ashburn, VA 20147
Mobile: 703-863-7357   |   Office: 703-967-1096 |   Fax: 571-386-1081   |   www.mjhomesalesva.com

  • About Us
  • Selling
  • Buying
  • Investing in Real Estate
  • Marketing
  • Get Pre-Qualified
  • 377 Old Winchester Rd. Boyce VA 22620
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