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$1,395,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 6 Beds
  • 4 Full Baths
  • 1 Partial Bath
  • 6,326 Sq. Ft.
  • 3 Car Garage
  • Updated 2 hours ago

Next open house:

Open House: 1:00 PM - 3:00 PM

Saturday 6/27 1:00 PM - 3:00 PM

16555 Chestnut Overlook Drive,Purcellville, VA 20132

16555 Chestnut Overlook DrivePurcellvilleVA20132

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Join us at 16555 Chestnut Overlook Drive on:

  • Open House: 2:00 PM - 4:00 PM

    Sunday 6/28 2:00 PM - 4:00 PM

    16555 Chestnut Overlook Drive,Purcellville, VA 20132
    16555 Chestnut Overlook DrivePurcellvilleVA20132
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Nestled on over 3 private acres with breathtaking mountain views, this exceptional home offers the perfect blend of space, comfort, and modern updates. With more than 6,000 square feet of living space, a desirable three-car side-loading garage, and a thoughtfully designed floor plan, this home is ideal for both everyday living and entertaining. The main level features an open-concept layout filled with natural light, a private home office, and a stunning sunroom that captures the surrounding views and creates the perfect place to relax year-round. The beautifully renovated kitchen (2023) serves as the heart of the home, with beautiful finishes, an abundance of counter space, and a large pantry. Upstairs, the spacious primary suite is a true retreat, complete with a private balcony overlooking the mountains, generous walk-in closets, and a luxurious ensuite bath featuring dual vanities, a soaking tub, and separate shower with amazing views to enjoy each morning. Four large additional bedrooms and two full bathrooms provide ample space for family and guests. The finished lower level offers incredible flexibility with a large recreation room, full bathroom, and additional bedroom that could serve as a guest suite, home gym or additional office. Step outside to the expansive brand-new deck (2025), the perfect place to unwind at the end of the day while taking in spectacular sunset views over the mountains. The fully fenced backyard also features a garden with raised beds, peaceful fire pit area and a cute and practical storage shed. Recent improvements include a new hot water heater (2024), kitchen renovation (2023), HVACs (2020 + 2021), a new well pump and lines (2025), and roof (2018), providing peace of mind for years to come. Ideally located just minutes from sought-after Loudoun County schools, shopping, dining, local wineries and breweries, the W&OD Trail, Loudoun Golf & Country Club, and Route 7. Best of all, enjoy the freedom and flexibility of no HOA while still being close to everything Loudoun County has to offer.

Full Property Details for 16555 Chestnut Overlook Dr

General

  • Price: $1,395,000
  • Taxes: $10,063 (2026)
  • Status: Active
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: VALO2129548
  • Updated: Today (6/26/2026)
  • Added to Site: Today

Interior

  • Interior Features: Bathroom - Soaking Tub, Bathroom - Walk-In Shower, Breakfast Area, Built-Ins, Ceiling Fan(s), Chair Railings, Combination Kitchen/Living, Crown Moldings, Dining Area, Water Treat System, Walk-in Closet(s), Wood Floors
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Appliances: Built-In Microwave, Cooktop, Dishwasher, Dryer, Refrigerator, Washer, Oven - Wall, Oven - Double

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

Exterior

  • Porch/Patio/Deck: Deck(s), Patio(s), Porch(es)

Parking

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

Location

  • County: LOUDOUN
  • Subdivision: CHESTNUT HILLS
  • 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
  • Cooling Fuel: Electric
  • Heating Type: Forced Air
  • Heating Fuel: Propane - Leased
  • Water Heater: Electric

Utilities

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

Structural Information

  • Architectural Style: Colonial
  • Structure Type: Detached
  • Construction: Masonry
  • Basement: Yes
  • Basement Entrance: Yes
  • Basement Desc.: Full, Fully Finished, Outside Entrance, Rear Entrance
  • Foundation: Other
  • Stories Description: Lower 1, Main, Upper 1
  • Square Feet: 6,326
  • Sq. Ft. Source: Estimated
  • 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: Trees/Woods, Mountain
  • Lot Size (Acres): 3.22
  • Lot Size (Sq. Ft.): 140,263
  • Lot Size Source: Assessor
  • Zoning: JLMA3

Financial Considerations

  • Price Per Sq. Ft.: $335.5
  • Assessment Year: 2026
  • City/TownTax Freq: Annually
  • County Tax: $10,063
  • County Tax Freq: Annually
  • Tax w/Assessment: $1,250,050
  • Tax Amount: $10,063
  • Tax Year: 2026
  • Tax Total Finished Sq. Ft.: 6058

Disclosures and Reports

  • Ownership: Fee Simple
  • Inclusions: Desk/bookshelf combo in lower level bedroom
  • Lot Number: 3

Listed by Pearson Smith Realty, LLC, Victoria Ro

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Listing agent

— 16555 Chestnut Overlook Dr —

  • Victoria Ro

    Pearson Smith Realty, LLC

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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
6/26/2026
Listed
$1,395,000
65.6%
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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*These costs are estimates, and the interest rates assume exceptional credit standing.

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NMLS#: 1598647

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Listed by Pearson Smith Realty, LLC, Victoria Ro

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16555 Chestnut Overlook Drive, Purcellville, VA 20132 (MLS# VALO2129548) is a Single Family property with 6 bedrooms, 4 full bathrooms and 1 partial bathroom. 16555 Chestnut Overlook Drive is currently listed for $1,395,000 and was received on June 26, 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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