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16555 Chestnut Overlook DrivePurcellville, VA 20132Price: $1,399,000

  • Price: $1,399,000
  • Est. Mortgage of $/month
  • 6 Days on Market
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$
%
$/month over payments
Federal 30-year interest rate: 6.48% last updated on Jun 4, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.
  • $1,399,000List Price
  • 6Bedrooms
  • 5Bathrooms
  • 6,058Square Feet
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.
Listed by Curt Andrew Schaber of On The Market Properties

Driving Directions

Railey Vacations
Railey Vacations
Office: 301-387-2124
5 Vacation Way
McHenry, MD 21541

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More Info

Location Information

  • Date Listed06/05/2026
  • ZoningJLMA3
  • UsmAreaPurcellville

School Information

  • Junior HighHarmony
  • High SchoolWoodgrove
  • Elementary SchoolMountain View

Parking

  • Parking FeaturesAsphalt Driveway, Crushed Stone
  • Parking TypesAttached Garage, Driveway
  • Total Garage And Parking Spaces13

Property

  • Road ResponsibilityState
  • Road Surface TypeBlack Top
  • Property ConditionExcellent
  • New Construction YNN
  • FencingWood, Rear, Board

Exterior

  • RoofArchitectural Shingle
  • FoundationPermanent, Slab
  • Window FeaturesDouble Hung, Screens, Storm, Transom
  • Exterior FeaturesExtensive Hardscape

Utilities

  • Water SourceWell
  • SewerOn Site Septic, Septic < # of BR
  • Central Air YNYes
  • Cooling FuelElectric
  • Water HeaterPropane
  • Heating FuelPropane - Leased, Pellets
  • Heat SystemCentral, Forced Air, Pellet Stove
  • Internet ServicesDSL

Basic Information

  • MLS NumberVALO2125662
  • Ownership InterestFee Simple
  • List Price$1,399,000
  • Square Feet6,058
  • Acreage3.22
  • Year Built2005
  • MLS Property TypeResidential
  • StatusACT

Location

  • Address16555 Chestnut Overlook Drive
  • Area Total6,058
  • SubdivisionChestnut Hills
  • TownPurcellville
  • StateVA
  • Zip20132
  • CountyLoudoun

Interior

  • FlooringCarpet, Ceramic Tile, Hardwood
  • Appliances Included
    • 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
  • Heating YNYes
  • CoolingCentral A/C, Ceiling Fan(s)
  • Basement YNYes

Property Information

  • Lot Size Square Feet140,263
  • Above Grade Finished Area4158
  • Below Grade Area Total1,900
  • Below Grade Finished Area1900

Amenities

  • PoolNo Pool
  • PricePerSqFt336
  • Other AmenitiesBasement, Fireplace, Garden, Mountain View

Other

  • Additional Parcels YNN
  • ExclusionsDrapes, Deck Fire Pit, and The Deck Furniture

Tax Information

  • Total Taxes Payment FrequencyAnnually
  • Tax Total Finished Sq Ft6,058
  • Tax Assessment Amount1250050
  • Tax Year2026
  • Taxes$9,628
  • County Tax$9,628
  • County Tax Payment FrequencyAnnually
  • Assessment Year2026

Building

  • ViewMountain, Trees/Woods
  • Rooms
    • Bathroom 1
    • Bathroom 2
    • Bathroom 3
    • Bedroom 2
    • Bedroom 3
    • Bedroom 4
    • Bedroom 5
    • Bedroom 6
    • Den
    • Dining Room
    • Family Room
    • Foyer
    • Half Bath
    • Kitchen
    • Laundry
    • Living Room
    • Primary Bathroom
    • Primary Bedroom
    • Recreation Room
    • Storage Room
    • Sun/Florida Room
    • Utility Room
  • Door FeaturesFrench, Six Panel, Storm
  • Walls Ceilings9'+ Ceilings, Dry Wall,2 Story Ceilings, Vaulted Ceilings
  • Interior FeaturesBathroom - 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
  • High School DistrictLoudoun County Public Schools
  • Broker NameOn The Market Properties
  • Building Number16555
  • Cross StreetAllder School Rd
  • DirectionsFrom Leesburg take Route 7 west approximately 7 mile and Exit onto SR-287 Berlin Tpke. Turn left onto Berlin Tpke. Travel 0.2 miles and turn right onto Hirst Rd. Travel 1.2 miles and turn right on Purcellville Rd. Travel 1 mile and turn left onto Allder School Rd. Travel 0.4 miles and turn left onto Chestnut Overlook Dr. 16555 Chestnut Overlook will be 700 ft on your right.
  • Num Attached Garage Spaces3
  • Lower Levels Total Baths1
  • Lower Level1 Total Baths1
  • Lower Level1 Full Baths1
  • Lower Level1 Bedrooms1
  • Lower Levels Total Bedrooms1
  • Lower Levels Total Full Baths1
  • Main Level Total Baths1
  • Main Level Half Baths1
  • Upper Levels Total Full Baths3
  • Upper Levels Total Bedrooms5
  • Upper Levels Total Baths3
  • Upper Level1 Bedrooms5
  • Upper Level1 Full Baths3
  • Upper Level1 Total Baths3
  • Story ListLower 1, Main, Upper 1
  • Structure Design TypeDetached
  • Construction MaterialsMasonry, Brick
  • Property StyleGeorgian, Colonial
  • Bedrooms6
  • BasementFully Finished, Outside Entrance, Rear Entrance, Interior Access, Connecting Stairway
  • Full Bath4
  • Bathroom5
  • Half Baths1
  • Laundry TypeMain Floor
  • Levels3
  • Fireplace FeaturesInsert, Mantel(s), Wood
  • Fireplace YNYes
  • Fireplace1
  • Garage TypeGarage - Side Entry, Garage Door Opener, Oversized, Other
  • Garage Spaces3
  • GarageYes
  • Patio And Porch FeaturesBalcony, Deck(s), Patio(s), Porch(es)
  • Garage SQFT630

Copyright 2026 BRIGHT, All Rights Reserved.  Information Deemed Reliable But Not Guaranteed. The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Railey Vacations participates, and is provided by BRIGHT through a licensing agreement. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.Data last updated June 10, 2026. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale.

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