This meticulously updated home blends timeless character with modern comfort, offering flexibility as a two-family or multi-generational single-family residence. Prior owners embraced multi-generational living, appreciating the spacious layout and exquisite built-ins that grace both living and dining rooms with elegance and timeless appeal. A grand central staircase links all 3 levels, while sun-drenched living areas flow seamlessly onto expansive, covered front porches. The first floor features a gas fireplace, and the second is warmed by a wood-burning Yodel stove. Both kitchens are thoughtfully renovated with vintage flair and include butler’s pantries. Thoughtful upgrades to all major systems ensure preserved historic integrity without compromising convenience. Lush landscaping with mature fruit trees, a generous backyard, & a two-car garage enhance the property’s appeal. Just steps from Winchester Center and the commuter rail, this home offers refined living in a prime location.

Step into comfort and sophistication in this beautifully curated Colonial, where thoughtful design meets everyday luxury. A spacious kitchen anchors the main level, showcasing quartz countertops, a generous breakfast bar & seating area complemented by a central island. The kitchen flows effortlessly into a family room lit by skylights, wood fireplace & soaring ceilings. Just beyond, a step-up private office offers a private & inspiring space for the at-home professional. The separate dining room is ideal for entertaining, while the eat-in kitchen provides a casual space for daily meals. Upstairs, a vaulted-ceilinged primary bath impresses with dramatic windows and a serene ensuite bath. All 4 bedrooms are spacious with plenty of natural light. The finished lower level is a dream—complete with a bonus room, game room, exercise room, and full bath—versatile enough to suit any lifestyle. Outside, the private backyard features a stunning stone patio, professional landscaping, & a hot tub.

Stately Colonial on 3.94 acres nestled in the Wyndcliff cul-de-sac, this elegant 4-bd, 3.5 bth property offers privacy, space, and timeless style. A dramatic foyer opens to a sitting room & formal DR. The e-i-k features granite counters, ss appliances, a new island cooktop & butler’s pantry. The FR impresses w/ skylights, a gas fp, surround sound & sliders to an expansive deck offering peaceful wooded views. Radiant heat warms the entire first floor. Upstairs enjoy a unique primary suite with a Jacuzzi tub and walk-in shower, 3 addtl bdrms,office, laundry & balcony. The heated lower level with separate entrance offers in-law/au pair potential (w/ town approval perfect ADU potential),w/ full bath and 2nd garage access. Many recent upgrades include roof, 5-bd septic system & well water tank. Both garages are heated-perfect for a car enthusiast, lush perennial gardens,trails in the backyard & attic for extra storage. Mins away from shops, restaurants & Nara Park. Commuter's dream.

Ideally situated on 2 private acres, this stylish, turnkey center-entrance Colonial offers timeless appeal & modern comfort. With hdwd floors throughout, 3 finished levels & a thoughtfully designed layout, this welcoming home checks all the boxes! The sun-filled frnt-bk FR is a standout, w oversized boxed bay windows, fp & built-in wetbar - perfect for gathering w family & friends; it opens seamlessly to the updated E-I kitchen, showcasing stainless appliances, classic, white subway tile backsplash & direct access to a private deck that overlooks the expansive, open bkyd. Generous 25' fp'd LR is flooded w light; french doors lead to an inviting screened porch- ideal for summer dining or relaxing afternoons. Upstairs are 4 spacious brs, including a serene primary suite, and a newly carpeted LL offers ideal flex space. Meticulously maintained, this home boasts an extensive list of updates (roof, septic, etc..) & sidewalks to the new middle school and town conservation land. Exceptional!

Bright, spacious, and full of potential, this 4-bedroom, 2-bath home offers over 2,200 sq ft in a quiet, scenic setting. Filled with natural light, it features a sunny living room with hardwood floors, crown molding, and a fireplace, plus a vaulted-ceiling family room with skylights, open to the kitchen. An atrium door leads to a composite deck overlooking a private, level yard—ideal for relaxing or entertaining. The main level also includes a first-floor primary bedroom with two closets and a dedicated office. Upstairs, you will find two additional bedrooms and a full bath with tub and shower. Additional highlights include Harvey tilt-in windows, a front porch, a 2-car garage with loft storage and a rear door for lawn tractor access, washer and dryer, sump pump, and lawn tractor. This home is move-in ready with the opportunity to modernize at your own pace. A rare chance to own in a town known for its top-rated schools. Property is being sold strictly as-is.