About this home

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.

Facts and features

Schools

• Orchard View Elementary School

  elementary · K-5 · 0.3 mi

  3

• Sherando High School

  high · 9-12 · 4.2 mi

  4

• James Wood Middle School

  middle · 6-8 · 5.0 mi

  3

• Mountain View Christian Academy

  elementary · K-12 · 1.9 mi

• Eukarya Christian Academy

  elementary · K-12 · 2.5 mi

• Bass-Hoover Elementary School

  elementary · K-5 · 3.1 mi

  2

Price history

• Sep 30, 2026 · Listed$799,900
• Jul 29, 2003 · Sold$85,000

Tax history

• 2026$4,169 tax · $786,700 assessed
• 2025$3,776 tax · $786,700 assessed
• 2024$3,510 tax · $688,400 assessed
• 2023$3,510 tax · $688,400 assessed
• 2022$3,419 tax · $560,500 assessed
• 2021$3,419 tax · $560,500 assessed
• 2020$3,017 tax · $494,700 assessed
• 2019$3,017 tax · $494,700 assessed

Home value

$783,400

• Cotality$783,400
• Quantarium$798,532
• Collateral Analytics$692,000

Where it is