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Barbara G. McMurry
Senior Vice President
REALTOR®, GRI, ePro, SFR
(434) 996-4120

16555 Chestnut Overlook Drive, Purcellville, VA 20132

$1,425,000
  • 16555 Chestnut Overlook Drive, Purcellville, VA 20132 Main Photo

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New to the Market ACTIVE
BEDS6 BATHS4 full 1 partial SQUARE FEET6,058 MLS#VALO2125662
STATUSACTIVE PROPERTY TYPEResidential - Single Family SUBDIVISIONCHESTNUT HILLS SCHOOLLOUDOUN COUNTY PUBLIC SCHOOLS

Property Description

Prepare to be captivated. A tree-lined approach reveals a sweeping expanse of manicured lawn, specimen trees, and mountain views framing this brick Colonial in Chestnut Overlook, set on one of the neighborhood’s premium lots offering five bedrooms on the upper level, six bedrooms total, and a floor plan that balances scale, comfort, and architectural presence. The impact of the approach is immediately echoed upon entry with a transom-topped front door and sidelights opening to a deep two-story foyer filled with natural light and extensive molding, a true introduction space defined by presence. A split staircase rises to the upper level while also turning toward the rear of the home, naturally separating formal and casual living areas, while sand-in-place wood floors run throughout the main level creating a warm, continuous backdrop for the home's living spaces. Formal living and dining rooms flank the foyer, both designed at an entertainment scale and finished with crown molding, chair rail, and shadow box detailing in the dining room, along with a generous powder room with linen storage on the main level. Beyond the formal rooms, the home transitions into a relaxed and cohesive living experience where the great room is anchored by a stacked stone fireplace with pellet stove insert, flowing seamlessly with the kitchen and sunroom to create a unified rear living environment designed for everyday living and entertaining. The kitchen features white cabinetry, quartz countertops, subway tile backsplash, large center island with five-burner cooktop, double ovens, built-in planning desk, and oversized walk-in pantry, while the mudroom offers custom cubbies, hooks, vertical shiplap, and a full laundry station with washer and dryer. The sunroom provides three walls of windows with transoms and opens to an expansive Trex deck with picture-frame border detailing, multiple seating zones, and stairs leading to a flagstone landing, while also on the main level is a private office with French doors and molding offering a quiet workspace. The upper level is accessed from either the dramatic open foyer staircase or the convenient rear staircase located just off the kitchen, and features five bedrooms including a primary suite at the rear of the home with long mountain and tree views, luxury vinyl plank flooring, recessed lighting, ceiling fan, oversized walk-in closet, and a private balcony offering an indulgent retreat ideal for morning coffee, sunsets, and stargazing; the primary bath includes dual vanities, dressing vanity, soaking tub, private water closet, and oversized walk-in shower. Secondary bedrooms are generously sized with two sharing a Jack-and-Jill bath with upgraded double vanity and quartz counters, one accessing the hall bath, and the fifth enjoying private entry. The finished lower level includes a large recreation room with high ceilings and recessed lighting and a full bath that is accessible from both the recreation area and the sixth bedroom with walk-in closet, providing exceptional flexibility for guests or extended living. The backyard extends the living experience with open lawn, mature trees, layered landscaping, fire pit, and a culinary garden with raised beds, irrigation, composting, cross-fencing, and wildlife protection. The three-car garage features a premium polyaspartic floor coating, and significant system updates provide peace of mind including a roof replaced in 2018, HVAC updates including upstairs heat pump, newer hot water heater, water filtration and softener system, and a new well pump installed in 2025. The setting offers privacy and space while remaining minutes from downtown Purcellville, Route 7, wineries, dining, and shopping.

16555 Chestnut Overlook Drive | MLS# VALO2125662

This single family home located at 16555 Chestnut Overlook Drive, Purcellville, VA 20132 is currently listed for sale with an asking price of $1,425,000. This property was built in 2005 and has 6 bedrooms and 4 full and 1 partial baths with 6058 sq. ft. Chestnut Overlook Drive is located in the CHESTNUT HILLS subdivision within the LOUDOUN COUNTY PUBLIC SCHOOLS school district. Search CHESTNUT HILLS real estate on bmcmurry.montaguemiller.com today.

Property Features

Property Type: Residential - Single Family
Basement: Yes
Basement: Fully Finished, Outside Entrance, Rear Entrance, Interior Access, Connecting Stairway
Cooling: Central A/C, Ceiling Fan(s)
Fireplaces: 1
Fuel Type: Propane - Leased, Pellets
Garage: 3
Heating: Central, Forced Air, Pellet Stove
Home Style: Georgian, Colonial
Lot Size: 3.22 Acres
Roof Type: Architectural Shingle
Stories: 3.0
Taxes: $9,628
Year Built: 2005

Feature Descriptions

Additional Structures: Above Grade, Below Grade
Appliances: Built-In Microwave, Cooktop, Dryer - Electric, Dryer - Front Loading, Exhaust Fan, Icemaker, Oven - Double, Oven - Wall, Refrigerator, Stainless Steel Appliances, Washer, Water Conditioner - Owned, Water Heater
Days on Site: 3
Exterior: Extensive Hardscape
Exterior: Masonry, Brick
Fencing: Wood, Rear, Board
Fireplace: Insert, Mantel(s), Wood
Flooring: Carpet, Ceramic Tile, Hardwood
Interior: Bathroom - Soaking Tub, Bathroom - Stall Shower, Bathroom - Tub Shower, Bathroom - Walk-In Shower, Breakfast Area, Built-Ins, Carpet, Ceiling Fan(s), Chair Railings, Combination Kitchen/Living, Crown Moldings, Dining Area, Double/Dual Staircase, Family Room Off Kitchen, Floor Plan - Open, Kitchen - Eat-In, Kitchen - Gourmet, Kitchen - Island, Pantry, Primary Bath(s), Recessed Lighting, Stove - Pellet, Upgraded Countertops, Wainscotting, Walk-in Closet(s), Water Treat System, Window Treatments, Wood Floors
Lot Dimensions: 3.22 Acre(S)
Parking Features: Asphalt Driveway, Crushed Stone
Parking Notes: 13 Total Parking Spaces
Rooms: Living Room, Dining Room, Primary Bedroom, Bedroom 2,Bedroom 3,Bedroom 4,Bedroom 5,Kitchen, Family Room, Den, Foyer, Sun/Florida Room, Laundry, Recreation Room, Storage Room, Utility Room, Bedroom 6,Bathroom 1,Bathroom 2,Bathroom 3,Primary Bathroom, Half Bath
Sewer: On Site Septic, Septic < # of BR
Special View Info: Mountain, Trees/Woods
SQFT Above Finished: 4158
SQFT Below Finished: 1900
SQFT Total Finished: 6058
Structure Type: Detached
Total Garage/Parking Spaces: 13
Water: Well
Windows: Double Hung, Screens, Storm, Transom

Room Sizes

Foyer: 17 x 11 Level - Main
Living Room: 15 x 12 Level - Main
Dining Room: 17 x 13 Level - Main
Family Room: 21 x 19 Level - Main
Den: 15 x 12 Level - Main
Sun/Florida Room: 16 x 11 Level - Main
Kitchen: 27 x 17 Level - Main
Half Bath: 6 x 4 Level - Main
Laundry: 9 x 5 Level - Main
Primary Bedroom: 37 x 18 Level - Upper 1
Primary Bathroom: 18 x 12 Level - Upper 1
Bedroom 3: 14 x 13 Level - Upper 1
Bedroom 4: 14 x 13 Level - Upper 1
Bedroom 5: 17 x 11 Level - Upper 1
Recreation Room: 41 x 34 Level - Lower 1
Bedroom 6: 17 x 14 Level - Lower 1
Bathroom 3: 7 x 7 Level - Lower 1
Bedroom 2: 24 x 16 Level - Upper 1
Bathroom 1: 11 x 5 Level - Upper 1
Bathroom 2: 10 x 5 Level - Upper 1
Storage Room: 20 x 17 Level - Lower 1
Recreation Room: 26 x 16 Level - Lower 1
Utility Room: 14 x 5 Level - Lower 1

Local Schools

High School: WOODGROVE
Middle School: HARMONY
Elementary School: MOUNTAIN VIEW
School District: LOUDOUN COUNTY PUBLIC SCHOOLS

Listed By / Shown By

Listed By

Agency Name: On The Market Properties
Agency Phone: 7034084261

Shown By

Agent Name: Barbara G. McMurry
Agent Phone: (434) 996-4120
Agency Title: Montague Miller & Co. Realtors

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Estimated Payment

$ 4,389.39 per month $3,171.43 Principal & Interest $802.33 Property Tax $415.63 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 06/05/2026. The listing information on this page last changed on 06/05/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Fri 06/05/2026 12:00:09 AM EST) or CAAR MLS (last updated Thu 06/04/2026 11:10:52 PM EST) or Staunton MLS (last updated Thu 06/04/2026 11:40:31 PM EST) or HRAR MLS (last updated Thu 06/04/2026 11:28:52 PM EST) or Lynchburg MLS (last updated Thu 06/04/2026 9:32:57 PM EST) or Bright MLS (last updated Thu 06/04/2026 11:50:29 PM EST). Real estate listings held by brokerage firms other than Montague Miller & Co. Realtors may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
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Agency License Information: Montague, Miller & Co. is licensed in the state of Virginia.



Agent License Information: Barbara G. McMurry, CRB,GRI,ePro,SFR Senior Vice President Montague Miller & Company REALTORS 500 Westfield Road Charlottesville, Virginia 22901 Lic. Broker in the Commonwealth of Virginia

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