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$539,900 Just Listed

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 3,561 Sq. Ft.
  • 2 Car Garage
  • Updated 1 day ago
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Welcome to 114 Settlers Circle, a spacious 5-bedroom, 3.5-bathroom home nestled on a quiet street in a prime east-side Winchester location. Classic curb appeal greets you with a timeless brick front, framed by gorgeous mature trees that offer natural shade, privacy, and lush beauty. Step inside to an elegant two-story foyer flanked by formal living and dining rooms, setting the stage for easy entertaining. The main level shines with gleaming hardwood floors throughout most of the living areas and flows effortlessly into a sun-filled kitchen. Outfitted with a convenient breakfast bar and pantry, the kitchen centers around a bright eat-in nook surrounded by wall-to-wall windows, seamlessly opening to a family room complete with a cozy gas fireplace. A convenient half bath rounds out the main floor. Upstairs, you will find a spacious primary suite featuring a large walk-in closet and a beautifully appointed attached bath with dual/split vanities and a relaxing corner soaking tub. The upper level also includes three additional bedrooms, another full bath, and convenient upper-level laundry. Brand-new carpet flows across both sets of stairs and three of the upper bedrooms-including the primary-while the fourth bedroom features classic hardwood flooring. The mostly finished basement features fresh carpet and offers endless possibilities for versatile living. A large recreation room provides the perfect layout for movie nights, an extra living area, a playroom, home office, or a dedicated workout space. It also boasts a private fifth bedroom alongside a full bathroom, ideal for extended family or overnight visitors. Practical functionality continues with an unfinished storage room and a fantastic workshop complete with built-in cabinetry and framed pegboard for tool organization. The outdoor setting is a true standout, featuring a covered deck off the main level where you can unwind rain or shine. Tucked seamlessly into a canopy of mature trees, the backyard offers exceptional privacy in a peaceful, serene environment. Lower-level access leads directly out to a covered patio and open deck, creating an ideal layout for outdoor entertaining or quiet mornings surrounded by nature. Complete with an attached 2-car garage for easy parking and extra storage, this move-in ready home delivers space, comfort, and character in an unbeatable location.

Full Property Details for 114 Settlers Cir

General

  • Price: $539,900
  • HOA FEE: $11/month
  • HOA FEE FREQ.: Annually
  • Taxes: $2,300 (2025)
  • Status: Active
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: VAFV2044852
  • Updated: 9/17/2026
  • Added to Site: 1 day(s) ago

Interior

  • Rooms/Areas: Living Room, Dining Room, Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Bedroom 5, Kitchen, Family Room, Foyer, Laundry, Recreation Room, Storage Room, Workshop, Primary Bathroom, Full Bath, Half Bath
  • Interior Features: Bathroom - Soaking Tub, Bathroom - Tub Shower, Bathroom - Stall Shower, Carpet, Ceiling Fan(s), Chair Railings, Crown Moldings, Dining Area, Family Room Off Kitchen, Formal/Separate Dining Room, Kitchen - Eat-In, Kitchen - Table Space, Pantry, Primary Bath(s), Recessed Lighting, Walk-in Closet(s), Wood Floors, Breakfast Area
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Fireplace(s): Gas/Propane
  • Appliances: Built-In Microwave, Dishwasher, Oven/Range - Electric, Refrigerator, Washer, Dryer
  • Flooring: Carpet, Ceramic Tile, Hardwood

Rooms

Bathrooms

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

Bedrooms

  • Total Bedrooms: 5
  • Bedrooms Upper: 4
  • Bedrooms Lower: 1

Other Rooms

  • Laundry: Upper Floor

Exterior

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

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 downtown Winchester, take Berryville Ave/Rt 7 east to a right on Valley Mill Rd, left on Asbury Rd and a right on Settlers Cir. The house will be on the right.

School Information

  • School District: Frederick County Public Schools
  • Elementary School: Redbud Run
  • Middle School: James Wood
  • High School: Millbrook

Community

  • Association: Yes

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Central A/C
  • Cooling Fuel: Electric
  • Heating Type: Forced Air
  • Heating Fuel: Natural Gas
  • Water Heater: Electric

Utilities

  • Sewer: Public Sewer
  • Water: Public

Structural Information

  • Architectural Style: Colonial
  • Structure Type: Detached
  • Construction: Brick, Vinyl Siding
  • Basement: Yes
  • Basement Desc.: Interior Access, Connecting Stairway, Partially Finished, Walkout Level, Windows, Workshop
  • Foundation: Slab
  • Roof: Asphalt
  • Walls/Ceilings: Vaulted Ceilings
  • Windows: Bay/Bow, Palladian
  • Stories Description: Lower 1, Main, Upper 1
  • Square Feet: 3,561
  • Sq. Ft. Source: Assessor
  • Living Area: 3,290 Sq. Ft.
  • Finished Above Grnd: 2,476 Sq. Ft.
  • Finished Below Grnd: 814 Sq. Ft.
  • Year Built: 1996
  • Year Built Source: Estimated

Unit Information

Unit 1

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

Lot Features

  • Property View: Trees/Woods
  • Lot Size (Acres): 0.32
  • Lot Size (Sq. Ft.): 13,787
  • Lot Size Source: Estimated
  • Zoning: RP

Financial Considerations

  • Price Per Sq. Ft.: $218.05
  • Association Fee: $130
  • Assoc Fee Freq.: Annually
  • Assessment Year: 2025
  • City/TownTax Freq: Annually
  • County Tax: $2,300
  • County Tax Freq: Annually
  • Tax w/Assessment: $479,100
  • Tax Amount: $2,300
  • Tax Year: 2025
  • Tax Total Finished Sq. Ft.: 3290

Disclosures and Reports

  • Ownership: Fee Simple
  • Lot Number: 69

Listed by Colony Realty, Daniel J Whitacre

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Listing agent

— 114 Settlers Cir —

  • Daniel J Whitacre

    Colony Realty

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 114 Settlers Cir

School District:Frederick County Public Schools, Winchester, VA
NameGradesDistance
Redbud Run Elementary School
250 First Woods Drive, Winchester, VA 22603
PK-50.6 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
9-120.9 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 114 Settlers Cir Get Price Alerts and Save Property

Date
Details
Price
Change
Source
9/17/2026
Listed
$539,900
80.57%
MLS
8/15/2016
Sold
$299,000
—
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 114 Settlers Cir

Year
Property Taxes
Change
Tax Assessment
Change
2026
$2,539
10%
$479,100
—
2025
$2,300
115%
$479,100
14%
2024
$1,072
-50%
$420,400
—
2023
$2,144
2%
$420,400
22%
2022
$2,101
—
$344,400
—
2021
$2,101
12%
$344,400
12%
2020
$1,870
—
$306,600
—
2019
$1,870
6%
$306,600
6%
2018
$1,760
2%
$288,500
—
2017
$1,731
9%
$288,500
9%
2016
$1,591
7%
$265,200
—
2015
$1,485
3%
$265,200
8%
2014
$1,436
—
$245,400
—
2013
$1,436
—
$245,400
—
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.

Estimate the Cost for 114 Settlers Cir

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Listed by Colony Realty, Daniel J Whitacre

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114 Settlers Circle, Winchester, VA 22602 (MLS# VAFV2044852) is a Single Family property with 5 bedrooms, 3 full bathrooms and 1 partial bathroom. 114 Settlers Circle is currently listed for $539,900 and was received on September 17, 2026. Want to learn more about 114 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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