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$1,425,000 Coming Soon

  • For Sale
  • Coming Soon
  • Single Family
  • 6 Beds
  • 4 Full Baths
  • 1 Partial Bath
  • 6,058 Sq. Ft.
  • 3 Car Garage
  • Updated 1 day ago
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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.

Full Property Details for 16555 Chestnut Overlook Dr

General

  • Price: $1,425,000
  • Taxes: $9,628 (2026)
  • Status: Coming Soon
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: VALO2125662
  • Updated: 6/1/2026
  • Added to Site: 3 day(s) ago
  • Expected Market Date: 6/5/2026

Interior

  • Rooms/Areas: 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
  • Interior Features: 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
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Fireplace(s): Insert, Mantel(s), Wood
  • 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
  • Flooring: Carpet, Ceramic Tile, Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 5
  • Full Bathrooms: 4
  • Half Bathrooms: 1
  • Upper Floor Baths: 3
  • Upper - Full Baths: 3
  • Main Floor Baths: 1
  • Main - 1/2 Baths: 1
  • Lower Floor Baths: 1
  • Lower - Full Baths: 1

Bedrooms

  • Total Bedrooms: 6
  • Bedrooms Upper: 5
  • Bedrooms Lower: 1

Other Rooms

  • Laundry: Main Floor

Exterior

  • Exterior Features: Extensive Hardscape
  • Porch/Patio/Deck: Balcony, Deck(s), Patio(s), Porch(es)

Parking

  • Garage: Yes
  • Garage Spaces: 3
  • Total Spaces: 13
  • Parking Features: Asphalt Driveway, Crushed Stone
  • Parking Type: Attached Garage, Driveway
  • Garage Description: Garage - Side Entry, Garage Door Opener, Oversized, Other

Location

  • County: LOUDOUN
  • Subdivision: CHESTNUT HILLS
  • Cross Streets: Allder School Rd
  • Driving Directions: From 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.

School Information

  • School District: Loudoun County Public Schools
  • Elementary School: Mountain View
  • Middle School: Harmony
  • High School: Woodgrove

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Central A/C, Ceiling Fan(s)
  • Cooling Fuel: Electric
  • Heating Type: Central, Forced Air, Pellet Stove
  • Heating Fuel: Propane - Leased, Pellets
  • Water Heater: Propane

Utilities

  • Sewer: On Site Septic, Septic < # of BR
  • Water: Well

Structural Information

  • Architectural Style: Georgian, Colonial
  • Structure Type: Detached
  • Construction: Masonry, Brick
  • Basement: Yes
  • Basement Entrance: Yes
  • Basement Desc.: Fully Finished, Outside Entrance, Rear Entrance, Interior Access, Connecting Stairway
  • Foundation: Permanent, Slab
  • Roof: Architectural Shingle
  • Walls/Ceilings: 9'+ Ceilings, Dry Wall, 2 Story Ceilings, Vaulted Cei
  • Windows: Double Hung, Screens, Storm, Transom
  • Doors: French, Six Panel, Storm
  • Stories Description: Lower 1, Main, Upper 1
  • Square Feet: 6,058
  • Sq. Ft. Source: Assessor
  • Living Area: 6,058 Sq. Ft.
  • Finished Above Grnd: 4,158 Sq. Ft.
  • Finished Below Grnd: 1,900 Sq. Ft.
  • Year Built: 2005
  • Year Built Source: Assessor
  • Property Condition: Excellent

Unit Information

Unit 1

  • Bathrooms-Lower: 1
  • Bedrooms-Lower: 1

Lot Features

  • Property View: Mountain, Trees/Woods
  • Lot Size (Acres): 3.22
  • Lot Size (Sq. Ft.): 140,263
  • Lot Size Source: Assessor
  • Street/Road Desc.: Black Top
  • Zoning: JLMA3
  • Fencing (Description): Wood, Rear, Board

Financial Considerations

  • Price Per Sq. Ft.: $342.71
  • Assessment Year: 2026
  • City/TownTax Freq: Annually
  • County Tax: $9,628
  • County Tax Freq: Annually
  • Tax w/Assessment: $1,250,050
  • Tax Amount: $9,628
  • Tax Year: 2026
  • Tax Total Finished Sq. Ft.: 6058

Disclosures and Reports

  • Ownership: Fee Simple
  • Exclusions: Drapes, Deck Fire Pit, and The Deck Furniture
  • Lot Number: 3

Listed by On The Market Properties, Curt Andrew Schaber and On The Market Properties, Samantha V. Fisher

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Listing agents

— 16555 Chestnut Overlook Dr —

  • Curt Andrew Schaber

    On The Market Properties

  • Samantha V. Fisher

    On The Market Properties

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 16555 Chestnut Overlook Dr

School District:Loudoun County Public Schools
NameGradesDistance
Woodgrove High School
36811 Allder School Road, Purcellville, VA 20132
9-120.4 mi
Harmony Middle School
38174 West Colonial Highway, Hamilton, VA 20158
6-82.5 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 16555 Chestnut Overlook Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
6/01/2026
Listed
$1,425,000
69.16%
MLS
5/26/2006
Sold
$842,400
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 16555 Chestnut Overlook Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$9,628
-3%
$1,196,080
5%
2023
$9,953
12%
$1,137,440
14%
2022
$8,902
18%
$1,000,270
30%
2021
$7,544
-1%
$769,820
5%
2020
$7,590
2%
$733,310
3%
2019
$7,438
-2%
$711,810
1%
2018
$7,610
-1%
$701,420
3%
2017
$7,658
1%
$680,690
3%
2016
$7,567
—
$660,890
-1%
2015
$7,573
1%
$667,250
3%
2014
$7,478
2%
$647,460
7%
2013
$7,315
—
$607,030
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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NMLS#: 1598647

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Listed by On The Market Properties, Curt Andrew Schaber and On The Market Properties, Samantha V. Fisher

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16555 Chestnut Overlook Drive, Purcellville, VA 20132 (MLS# VALO2125662) is a Single Family property with 6 bedrooms, 4 full bathrooms and 1 partial bathroom. 16555 Chestnut Overlook Drive is currently listed for $1,425,000 and was received on June 01, 2026. Want to learn more about 16555 Chestnut Overlook Drive? Do you have questions about finding other Single Family real estate for sale in Purcellville? You can browse all Purcellville real estate or contact a Coldwell Banker agent to request more information.

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