Welcome home to 505 Glendobbin Rd – a cherished haven nestled in the heart of one of Winchester's most coveted areas-Apple Pie Ridge. This exquisite residence, proudly held by its original owner, now graces the market for the very first time. A testament to timeless care and affection, this home exudes warmth and character in every corner. Situated strategically for the modern commuter, this home offers seamless access to major routes with the convenience of the nearby hospital, schools, shopping and Winchester's historic district. Unfolding across an expansive canvas of five and a half acres, this property is a sanctuary of privacy and tranquility with plenty of mature trees and open land. The possibilities are endless with the lush landscape- whether it's an intimate family picnic or a grand soirée, this sprawling outdoor oasis is primed for all your entertainment aspirations. Walk up the pathway and under the covered front porch to enter inside, where the legacy of love and meticulous upkeep is palpable. While the home has a traditional floor plan, it offers a unique opportunity for the new owners to modernize at their convenience. However, a formal living and dining room, centrally located kitchen and large family room with deck access make this home move-in ready. Upstairs, the primary bedroom along with en suite, which boasts Carrara marble sink tops and a walk-in closet, provide fantastic space with opportunity to personalize. A large bedroom over the garage would be great for guests, a home office, gym or playroom. The unfinished, walk out basement is great for storage with high ceilings, making it a space that could be easily finished. The curb appeal is truly stunning with a large driveway, oversized garage and deck with mountain views. This is your chance to seize the extraordinary – a home that has been cherished by its original owner and is now ready to embrace its new chapter. Homes of this caliber, in this coveted location, are a true rarity. The opportunity is here, the time is now – come experience 505 Glendobbin Rd today! The home has Anderson Windows. Fence updated (2017), D-box replaced (2012), Whole house paint (2021), New well pump (2023), New AC Unit (2021/2013), New basement furnace (2013), H2O softener (2015), Primary bath tile (2017), Architectural Shingles (2006), 1K gallons buried propane tank-owned.