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$499,900 Just Listed

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 3,388 Sq. Ft.
  • 2 Car Garage
  • Updated 21 hours ago
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This classic Colonial home, ideally situated in a desirable Winchester neighborhood, offers 3 spacious bedrooms and 2.5 baths. Rich in charm, this home boasts a traditional layout with over 3300 sq feet on 3 levels. There is a Bonus room that would be perfect for use as a 4th bedroom, home office, or guest space. Improvements include a Brand new architectural shingle roof, newer water heater, and a well maintained dually zoned HVAC system with a new condenser unit. You will LOVE the Gleaming wood floors throughout the main level! Bathrooms are updated with luxury vinyl plank and tile flooring. The Kitchen is elegant with vintage style cabinetry, granite countertops, gas stove cooking, a roomy pantry, and an island, all overlooking the large landscaped backyard. A great place to entertain, the rear outdoor space has a stunning patio with a cozy pergola, relaxing water fountains, and a warm fire pit area to gather around. Not to mention the Fully fenced rear has lots of majestic trees for a feeling of privacy and peace. The Unnfinished basement has a rough-in and it's just waiting for your dream project! This location has effortless access to vibrant downtown, with a variety of restaurants, entertainment, and cultural attractions! Ideal location for commuters! A Must See Schedule a Showing Today!

Full Property Details for 102 Settlers Cir

General

  • Price: $499,900
  • HOA FEE: $11/month
  • HOA FEE FREQ.: Annually
  • Taxes: $1,847 (2025)
  • Status: Active
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: VAFV2042324
  • Updated: 6/12/2026
  • Added to Site: 1 day(s) ago

Interior

  • Rooms/Areas: Living Room, Dining Room, Primary Bedroom, Bedroom 2, Bedroom 3, Kitchen, Family Room, Basement, Laundry, Bathroom 2, Bonus Room, Primary Bathroom, Half Bath
  • Interior Features: Bathroom - Tub Shower, Breakfast Area, Carpet, Ceiling Fan(s), Chair Railings, Crown Moldings, Dining Area, Family Room Off Kitchen, Floor Plan - Traditional, Formal/Separate Dining Room, Kitchen - Eat-In, Kitchen - Island, Kitchen - Table Space, Pantry, Primary Bath(s), Recessed Lighting, Upgraded Countertops, Walk-in Closet(s), Wood Floors
  • Appliances: Built-In Microwave, Dishwasher, Disposal, Dryer, Extra Refrigerator/Freezer, Oven/Range - Gas, Refrigerator, Stainless Steel Appliances, Washer, Water Heater
  • Flooring: Carpet, Engineered Wood, Luxury Vinyl Plank, Luxury Vinyl Tile, Rough-In

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

Other Rooms

  • Laundry: Upper Floor

Exterior

  • Exterior Features: Extensive Hardscape, Exterior Lighting, Gutter System, Outbuilding(s), Play Equipment, Water Fountains
  • Porch/Patio/Deck: Patio(s), Porch(es)

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 2
  • Parking Type: Attached Garage, Driveway, Off Street
  • Garage Description: Garage - Front Entry, Inside Access, Garage Door Opener

Location

  • County: FREDERICK
  • Subdivision: PIONEER HEIGHTS
  • Driving Directions: From East of Winchester: Rte 7 to Left on Greenwood Rd. to Left onto Battlefield Dr . Turn Left on Asbury Rd to Right on Settlers Cir. Home on Right.

School Information

  • School District: Frederick County Public Schools

Community

  • Association: Yes
  • Assoc. Fees Include: Snow Removal

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Ceiling Fan(s), Central A/C, Zoned
  • Cooling Fuel: Electric
  • Heating Type: Forced Air, Zoned
  • Heating Fuel: Natural Gas
  • Water Heater: Natural Gas

Utilities

  • Sewer: Public Sewer
  • Water: Public

Structural Information

  • Architectural Style: Colonial
  • Structure Type: Detached
  • Construction: Vinyl Siding
  • Basement: Yes
  • Basement Desc.: Unfinished, Rough Bath Plumb
  • Foundation: Block
  • Roof: Architectural Shingle
  • Stories Description: Main, Upper 1
  • Square Feet: 3,388
  • Sq. Ft. Source: Estimated
  • Living Area: 2,268 Sq. Ft.
  • Finished Above Grnd: 2,268 Sq. Ft.
  • Year Built: 1996
  • Year Built Source: Assessor
  • Property Condition: Excellent

Lot Features

  • Lot Size (Acres): 0.27
  • Lot Size (Sq. Ft.): 11,761
  • Lot Size Source: Estimated
  • Zoning: RP
  • Lot Description: Landscaping, Level, Rear Yard
  • Fencing (Description): Rear, Wood

Financial Considerations

  • Price Per Sq. Ft.: $220.41
  • Association Fee: $130
  • Assoc Fee Freq.: Annually
  • Assessment Year: 2025
  • City/TownTax Freq: Annually
  • County Tax: $1,847
  • County Tax Freq: Annually
  • Tax w/Assessment: $384,700
  • Tax Amount: $1,847
  • Tax Year: 2025
  • Tax Total Finished Sq. Ft.: 2268

Disclosures and Reports

  • Ownership: Fee Simple
  • Exclusions: Surf swing hanging from backyard tree
  • Inclusions: Playset platform with slide, pergola with canopy, water fountains, shed box in corner of backyard
  • Lot Number: 75

Listed by ERA Oakcrest Realty, Inc., Jodi Costello

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Listing agent

— 102 Settlers Cir —

  • Jodi Costello

    ERA Oakcrest Realty, Inc.

Listing Office Email: info@oakcrestrealty.com

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 102 Settlers Cir

School District:Frederick County Public Schools, Winchester, VA
NameGradesDistance
Redbud Run Elementary School
250 First Woods Drive, Winchester, VA 22603
PK-50.5 mi
James Wood Middle School
1313 Amherst Street, Winchester, VA 22601
6-84.2 mi
Millbrook High School
251 First Woods Drive, Winchester, VA 22603
9-120.8 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 102 Settlers Cir Get Price Alerts and Save Property

Date
Details
Price
Change
Source
6/12/2026
Listed
$499,900
122.52%
MLS
8/31/2016
Sold
$224,652
—
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 102 Settlers Cir

Year
Property Taxes
Change
Tax Assessment
Change
2024
$794
—
$384,700
24%
2024
$794
-50%
$311,200
—
2023
$1,587
-3%
$311,200
16%
2022
$1,632
—
$267,500
—
2021
$1,632
3%
$267,500
3%
2020
$1,590
—
$260,600
—
2019
$1,590
6%
$260,600
6%
2018
$1,504
2%
$246,500
—
2017
$1,479
10%
$246,500
10%
2016
$1,343
7%
$223,800
—
2015
$1,253
1%
$223,800
6%
2014
$1,239
—
$211,800
—
2013
$1,239
—
$211,800
—
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.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by ERA Oakcrest Realty, Inc., Jodi Costello

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102 Settlers Circle, Winchester, VA 22602 (MLS# VAFV2042324) is a Single Family property with 3 bedrooms, 2 full bathrooms and 1 partial bathroom. 102 Settlers Circle is currently listed for $499,900 and was received on June 12, 2026. Want to learn more about 102 Settlers Circle? Do you have questions about finding other Single Family real estate for sale in Winchester? You can browse all Winchester real estate or contact a Coldwell Banker agent to request more information.

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