Date
Details
Price
Change
Source
9/30/2026
Listed
$799,900
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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Property Description
Boasting timeless architectural charm and sweeping countryside views, 119 Cheifton Place offers an extraordinary lifestyle on an expansive two plus acre lot. Frame-worthy curb appeal greets you with lush landscaping, tall shade trees, and a welcoming covered porch, while a wide driveway and attached three-car garage comfortably accommodate all your guests. Inside, an inviting foyer detailed with refined pillars, custom crown molding, and wainscoting sets a sophisticated tone. Host formal dinners in the dedicated dining room, or work in peace behind the glass French doors of the private main-floor office. The expansive family room anchors the main floor with its high vaulted ceilings, cozy stone fireplace, and abundant natural light pouring in through large picture windows. Nearby, the well-appointed kitchen features timeless cherry cabinetry, a center island, stainless steel appliances, and a bright breakfast nook. A flexible den just off the kitchen boasts vaulted ceilings and tons of windows showcasing beautiful views, offering endless possibilities as a playroom, library, or secondary sitting room. A main-level powder room and a spacious laundry room with built-in storage complete this thoughtfully designed main living area. The main-level primary suite serves as a serene retreat, complete with expansive windows, two fabulous walk-in closets, and a spa-like ensuite bath featuring double sinks, a deep soaking tub, and a separate walk-in shower. Two additional generously sized bedrooms and another full bath round out the main floor. Downstairs, the finished walkout basement exponentially expands your living options, flooded with natural light from large windows. This thoughtfully finished lower level offers unprecedented flexibility, featuring a huge recreation room, a media room tailored for movie nights or game days, a bright work space, a private guest bedroom, a third full bath, and an unfinished area perfect for storage. Whether you imagine an in-law suite, a high-end game room, a home gym, or the ultimate entertainment hub, this versatile space delivers endless possibilities. Designed for seamless indoor-outdoor entertaining, the exterior is a private oasis framed by meticulous landscaping. Relax on the rear deck while taking in breathtaking panoramic views of the lush rolling countryside, gather for crisp autumn evenings around the fire pit on the lower brick patio, or unwind in the shade on the covered patio directly off the basement walkout. Impeccably maintained inside and out, this remarkable property is a rare find offering unmatched space, classic design, and resort-style living in a prime location minutes to agritourism, downtown Winchester, schools, shopping and more.
Full Property Details
Full Property Details for 119 Cheifton Pl
General
- Price: $799,900
- Taxes: $3,776 (2025)
- Status: Active
- Type: Single Family
- Source: BrightMLSMidAtlantic
- MLS ID: VAFV2045098
- Updated: 9/30/2026
- Added to Site: 2 day(s) ago
Interior
- Rooms/Areas: Dining Room, Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Kitchen, Family Room, Den, Laundry, Office, Recreation Room, Storage Room, Media Room, Bonus Room, Primary Bathroom, Full Bath, Half Bath
- Interior Features: Bathroom - Soaking Tub, Bathroom - Tub Shower, Bathroom - Walk-In Shower, Breakfast Area, Carpet, Ceiling Fan(s), Crown Moldings, Dining Area, Entry Level Bedroom, Family Room Off Kitchen, Formal/Separate Dining Room, Kitchen - Eat-In, Kitchen - Island, Kitchen - Table Space, Primary Bath(s), Recessed Lighting, Wainscotting, Walk-in Closet(s), Wood Floors, Window Treatments
- Fireplace: Yes
- Number of Fireplaces: 1
- Fireplace(s): Stone, Gas/Propane
- Appliances: Built-In Microwave, Cooktop, Dishwasher, Disposal, Dryer, Washer, Refrigerator, Oven - Wall, Stainless Steel Appliances
- Flooring: Hardwood, Carpet, Ceramic Tile
Rooms
Bathrooms
- Total Bathrooms: 4
- Full Bathrooms: 3
- Half Bathrooms: 1
- Main Floor Baths: 3
- Main - Full Baths: 2
- Main - 1/2 Baths: 1
- Lower Floor Baths: 1
- Lower - Full Baths: 1
Bedrooms
- Total Bedrooms: 4
- Bedrooms Lower: 1
- Bedrooms Main & Up: 3
Other Rooms
- Laundry: Main Floor
Exterior
- Exterior Features: Extensive Hardscape
- Porch/Patio/Deck: Deck(s), Patio(s), Porch(es), Brick
Parking
- Garage: Yes
- Garage Spaces: 3
- Total Spaces: 3
- Parking Type: Attached Garage, Driveway, Off Street
- Garage Description: Garage - Front Entry, Inside Access, Garage Door Opener
Location
- County: FREDERICK
- Subdivision: THE ORCHARD
- Driving Directions: From Winchester, take Rt 11 south to a right on Middle Rd and right on Cheifton Pl. The home is the first one on the left.
School Information
- School District: Frederick County Public Schools
Heating & Cooling
- Central air: Yes
- Cooling Type: Central A/C, Ceiling Fan(s)
- Cooling Fuel: Electric
- Heating Type: Forced Air
- Heating Fuel: Propane - Leased
- Water Heater: Propane
Utilities
- Sewer: On Site Septic
- Water: Well
Structural Information
- Architectural Style: Ranch/Rambler
- Structure Type: Detached
- Construction: Vinyl Siding, Brick
- Basement: Yes
- Basement Entrance: Yes
- Basement Desc.: Full, Interior Access, Partially Finished, Outside Entrance, Connecting Stairway, Walkout Level, Windows
- Foundation: Concrete Perimeter
- Walls/Ceilings: Vaulted Ceilings
- Doors: French
- Stories Description: Lower 1, Main
- Square Feet: 5,536
- Sq. Ft. Source: Estimated
- Living Area: 4,160 Sq. Ft.
- Finished Above Grnd: 2,784 Sq. Ft.
- Finished Below Grnd: 1,376 Sq. Ft.
- Year Built: 2005
- Year Built Source: Estimated
Unit Information
Unit 1
- Bathrooms-Lower: 1
- Bedrooms-Lower: 1
Lot Features
- Property View: Scenic Vista
- Lot Size (Acres): 2.14
- Lot Size (Sq. Ft.): 93,348
- Lot Size Source: Estimated
- Zoning: RA
- Lot Description: Corner, Landscaping
Financial Considerations
- Price Per Sq. Ft.: $287.32
- Tax w/Assessment: $786,700
- Tax Amount: $3,776
- Tax Year: 2025
Disclosures and Reports
- Ownership: Fee Simple
- Inclusions: Bose speaker system & UV light system in HVAC
Listed by Colony Realty, Daniel J Whitacre
We Value Your Privacy
We Value Your Privacy
We Value Your Privacy
Listing agent
— 119 Cheifton Pl —
Daniel J Whitacre
Colony Realty
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 119 Cheifton Pl
School District:Frederick County Public Schools, Winchester, VA
| Name | Grades | Distance |
|---|---|---|
Orchard View Elementary School 4275 Middle Road, Winchester, VA 22602 | K-5 | 0.3 mi |
James Wood Middle School 1313 Amherst Street, Winchester, VA 22601 | 6-8 | 5 mi |
Sherando High School 185 South Warrior Drive, Stephens City, VA 22655 | 9-12 | 4.3 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 119 Cheifton Pl
Tax History
Tax History for 119 Cheifton Pl
Year
Property Taxes
Change
Tax Assessment
Change
2026
$4,170
100%
$786,700
—
2024
100%
$786,700
14%
2024
-100%
$688,400
—
2023
$1,755
-49%
$688,400
23%
2022
$3,419
—
$560,500
—
2021
$3,419
13%
$560,500
13%
2020
$3,018
—
$494,700
—
2019
$3,018
5%
$494,700
5%
2018
$2,868
2%
$470,100
—
2017
$2,821
10%
$470,100
10%
2016
$2,564
7%
$427,400
—
2015
$2,393
5%
$427,400
10%
2014
$2,283
—
$390,300
—
2013
$2,283
—
$390,300
—
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
Estimate the Cost for 119 Cheifton Pl
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- Single Family
- Active
- Updated 6 days ago
- 4Beds
- 3Total Baths
- 3,150Sq. Ft.
- Single Family
- Active
- Updated 4 days ago
- 4Beds
- 3Total Baths
- 4,503Sq. Ft.
- Single Family
- Active
- Updated 8 days ago
- 4Beds
- 5Total Baths
- 5,102Sq. Ft.
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- Single Family
- Active
- Updated 1 day ago
- 4Beds
- 4Total Baths
- 5,280Sq. Ft.
- Single Family
- Active
- Updated 3 days ago
- 2Beds
- 2Total Baths
- 1,448Sq. Ft.
- Single Family
- Active
- Updated 2 days ago
- 3Beds
- 2Total Baths
- 1,944Sq. Ft.
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- Single Family
- Active
- Updated 2 days ago
- 4Beds
- 2Total Baths
- 2,400Sq. Ft.
- Single Family
- Active
- Updated 3 days ago
- 3Beds
- 2Total Baths
- 1,344Sq. Ft.
- Single Family
- Active
- Updated 2 hours ago
- 3Beds
- 3Total Baths
- 2,039Sq. Ft.
- Single Family
- Active
- Updated 4 days ago
- 3Beds
- 2Total Baths
- 1,493Sq. Ft.
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119 Cheifton Place, Winchester, VA 22602 (MLS# VAFV2045098) is a Single Family property with 4 bedrooms, 3 full bathrooms and 1 partial bathroom. 119 Cheifton Place is currently listed for $799,900 and was received on September 30, 2026. Want to learn more about 119 Cheifton Place? 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.