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$425,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 2,477 Sq. Ft.
  • 2 Car Garage
  • Updated 6 hours ago
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Welcome to 106 Chesterfield Court, tucked inside the sought-after Lake of the Woods community. From the moment you pull into the driveway, this 3-bedroom, 2.5-bath Colonial feels warm and inviting, offering 2,477 square feet of thoughtfully designed living space. The main level is ideal for both everyday living and entertaining. A cozy living room with a fireplace sets the tone for relaxed evenings, while the formal dining room provides the perfect space for hosting gatherings and special occasions. Just off the family room, the kitchen shines with granite countertops, stainless steel appliances, and ample cabinet and counter space. The adjoining breakfast room offers a casual dining option and opens to the screened porch-an ideal spot to enjoy your morning coffee or unwind at the end of the day while taking in the peaceful surroundings. Upstairs, the primary suite serves as a comfortable retreat, featuring a spacious bedroom, a private ensuite bath, and a large walk-in closet. Two additional well-sized bedrooms are connected by a convenient Jack-and-Jill bathroom, offering both function and privacy. A dedicated laundry room and a two-car garage add to the home's practicality, while the classic Colonial layout provides timeless appeal. Step outside to a backyard designed for enjoyment, offering space to relax, entertain, or simply enjoy the outdoors. Whether hosting summer cookouts, letting pets play, or creating your own outdoor oasis, this yard provides flexibility and room to make it your own. Step outside and enjoy multiple outdoor living options, including a screened-in porch and a private deck: ideal for relaxing, dining, or enjoying the surroundings. With its comfortable interior spaces and inviting outdoor areas, this home offers a wonderful opportunity to enjoy all that Lake of the Woods has to offer, including its amenities, natural beauty, and community lifestyle. Nestled in a private, secure, gated community, Lake of the Woods is a paradise of possibilities. With two lakes, a golf course, an equestrian center, fire and rescue services, and even a church within its bounds, this community offers a diverse range of activities. From boating, water skiing, kayaking, and golfing to the simple joy of soaking in mesmerizing views from the clubhouse, deck, yard, or beaches, there's something for everyone. Engage your interests by joining over 60 clubs and organizations, or perhaps indulge in a game of bridge or contribute your talents as a volunteer. Lake of the Woods truly caters to your lifestyle. Located in Orange County, enjoy the added advantage of low real estate taxes. With home prices spanning from $300,000+ to over $1,800,000, Lake of the Woods is the ideal haven for both full-time residents and weekenders. Don't just take my word for it - come and see for yourself! Allow me to guide you through a tour of Lake of the Woods, showcasing the very essence of what makes this community so special. Experience firsthand the captivating charm of Lake of the Woods!

Full Property Details for 106 Chesterfield Ct

General

  • Price: $425,000
  • HOA FEE: $191/month
  • HOA FEE FREQ.: Annually
  • Taxes: $2,560 (2025)
  • Status: Active
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: VAOR2013196
  • Updated: 1/30/2026
  • Added to Site: 1 day(s) ago

Interior

  • Rooms/Areas: Living Room, Dining Room, Primary Bedroom, Bedroom 2, Bedroom 3, Kitchen, Family Room, Foyer, Breakfast Room, Study, Other
  • Interior Features: Dining Area, Family Room Off Kitchen, Breakfast Area, Built-Ins, Chair Railings, Crown Moldings, Primary Bath(s), Window Treatments, Wood Floors, Upgraded Countertops, Floor Plan - Open
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Appliances: Washer/Dryer Hookups Only, Dishwasher, Disposal, Icemaker, Oven/Range - Electric, Refrigerator, Exhaust Fan

Rooms

Bathrooms

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

Bedrooms

  • Total Bedrooms: 3
  • Bedrooms Upper: 3

Additional Information

  • Shared Amenities: Bar/Lounge, Baseball Field, Basketball Courts, Beach, Bike Trail, Boat Dock/Slip, Boat Ramp, Club House, Community Center, Common Grounds, Dining Rooms, Dog Park, Fitness Center, Gated Community, Gift Shop, Golf Club, Golf Course, Golf Course Membership Available, Horse Trails, Jog/Walk Path, Lake, Marina/Marina Club, Meeting Room, Mooring Area, Newspaper Service, Party Room, Picnic Area, Pier/Dock, Pool - Outdoor, Putting Green, Recreational Center, Riding/Stables, Security, Swimming Pool, Tennis Courts, Tot Lots/Playground, Wate
  • Shared Pool: Yes
  • Pool: Yes

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 6
  • Parking Features: Paved Driveway
  • Parking Type: Driveway, Attached Garage
  • Garage Description: Garage - Front Entry, Garage Door Opener

Location

  • County: ORANGE
  • Subdivision: LAKE OF THE WOODS
  • Driving Directions: From I-95, take exit 130B West toward Culpeper. Drive about 14.8 miles. Turn left onto Lake of the Woods Way. Left onto Lakeview Pkwy. Left onto Mt. Pleasant. Left onto Birdie, Left onto Westover Pkwy, Left onto Chesterfield Court.

School Information

  • School District: Orange County Public Schools
  • Elementary School: Locust Grove
  • Middle School: Locust Grove
  • High School: Orange

Community

  • Association: Yes
  • Assoc. Name: LAKE OF THE WOODS ASSOCIATION
  • Assoc. Fees Include: Common Area Maintenance, Custodial Services Maintenance, Insurance, Management, Pier/Dock Maintenance, Pool(s), Recreation Facility, Reserve Funds, Road Maintenance, Security Gate, Snow Removal

Heating & Cooling

  • Cooling Type: Heat Pump(s), Ceiling Fan(s), Zoned
  • Cooling Fuel: Electric
  • Heating Type: Heat Pump(s), Zoned
  • Heating Fuel: Electric, Wood
  • Water Heater: Electric

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Cable TV Available, Electric Available, Phone Available, Sewer Available, Water Available

Structural Information

  • Architectural Style: Colonial
  • Structure Type: Detached
  • Construction: Vinyl Siding, Combination, Brick
  • Foundation: Crawl Space
  • Windows: Bay/Bow
  • Doors: Storm
  • Stories/Levels: 2
  • Stories Description: Main, Upper 1
  • Square Feet: 2,477
  • Sq. Ft. Source: Estimated
  • Living Area: 2,477 Sq. Ft.
  • Finished Above Grnd: 2,477 Sq. Ft.
  • Year Built: 1990
  • Year Built Source: Assessor
  • Property Condition: Excellent

Lot Features

  • Lot Size (Acres): 0.36
  • Lot Size (Sq. Ft.): 15,702
  • Lot Size Source: Estimated
  • Zoning: R3
  • Lot Description: Landscaping

Horse Property

  • Horse Property: Yes
  • Horse Facility Desc.: Arena, Horse Trails, Horses Allowed, Paddock, Riding Ring, Stable(s)

Water Features

  • Navigable Water: Yes
  • Water Access: Yes
  • Water Access Desc: Boat - Powered, Canoe/Kayak, Fishing Allowed, Personal Watercraft (PWC), Public Access, Swimming Allowed, Waterski/Wakeboard
  • Water Front Type: Lake

Financial Considerations

  • Price Per Sq. Ft.: $171.58
  • Association Fee: $2,295
  • Assoc Fee Freq.: Annually
  • Assessment Year: 2025
  • City/TownTax Freq: Annually
  • County Tax: $2,560
  • County Tax Freq: Annually
  • Tax w/Assessment: $413,000
  • Tax Amount: $2,560
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Section: 13
  • Lot Number: 27

Listed by EXP Realty, LLC, Kathleen Annette Ayers and EXP Realty, LLC, Patricia E Licata

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Listing agents

— 106 Chesterfield Ct —

  • Kathleen Annette Ayers

    EXP Realty, LLC

  • Patricia E Licata

    EXP Realty, LLC

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 106 Chesterfield Ct

School District:Orange County Public Schools
NameGradesDistance
Locust Grove Primary School
31230 Constitution Highway, Locust Grove, VA 22508
PK-25.5 mi
Locust Grove Elementary School
31208 Constitution Highway, Locust Grove, VA 22508
3-55.6 mi
Locust Grove Middle School
6368 Flat Run Road, Locust Grove, VA 22508
6-84.3 mi
Orange Co. High School
201 Selma Road, Orange, VA 22960
9-1220.3 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 106 Chesterfield Ct Get Price Alerts and Save Property

Date
Details
Price
Change
Source
1/29/2026
Listed
$425,000
91.01%
MLS
10/25/2017
Sold
$222,500
—
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 106 Chesterfield Ct

Year
Property Taxes
Change
Tax Assessment
Change
2025
$2,046
—
$270,100
—
2024
$2,046
—
$270,100
—
2023
$2,046
—
$270,100
—
2022
$2,046
4%
$270,100
-1%
2021
$1,964
—
$272,800
—
2020
$1,964
4%
$272,800
16%
2019
$1,887
—
$234,700
—
2018
$1,887
—
$234,700
—
2017
$1,887
—
$234,700
—
2016
$1,887
8%
$234,700
8%
2015
$1,748
—
$217,400
—
2014
$1,748
12%
$217,400
—
2013
$1,565
—
$217,400
—
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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Listed by EXP Realty, LLC, Kathleen Annette Ayers and EXP Realty, LLC, Patricia E Licata

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106 Chesterfield Court, Locust Grove, VA 22508 (MLS# VAOR2013196) is a Single Family property with 3 bedrooms, 2 full bathrooms and 1 partial bathroom. 106 Chesterfield Court is currently listed for $425,000 and was received on January 29, 2026. Want to learn more about 106 Chesterfield Court? Do you have questions about finding other Single Family real estate for sale in Locust Grove? You can browse all Locust Grove real estate or contact a Coldwell Banker agent to request more information.

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