Welcome to 2 Chestnut Street, an exquisite new construction home in progress by Mark Stephen Development. Situated off coveted Main Street in one of Winchester’s most sought-after neighborhoods, this residence is thoughtfully designed to blend timeless charm with modern conveniences. The home will feature five spacious bedrooms, five full bathrooms, a first-floor office, and a basement offering flexible space for an additional office, playroom, exercise room, or living area. The open-concept kitchen will include premium appliances, a grand nine-foot island, and custom cabinetry, while the primary suite will boast luxurious his-and-her closets and a spa-like bathroom with a soaking tub and marble-tiled shower. A third-floor bonus space adds versatility. With mature landscaping providing privacy and a spacious patio for outdoor living, this property is conveniently located near Winchester town center, top-rated schools, offers easy access to Boston, and promises an unparalleled lifestyle

Nestled in a sought-after neighborhood, this stunningly reimagined home combines timeless charm and modern comfort, just a short walk to downtown. The inviting foyer welcomes you from a wrap-around porch into an open yet intimate layout connecting the kitchen, dining, and family rooms. A mudroom with marble checkered flooring and a walk-in pantry with a beverage fridge add practical luxury. The second floor offers three spacious bedrooms, including a serene primary suite with a walk-in closet and luxurious en-suite, plus a second bathroom and adjacent laundry room. The third floor features a private retreat with a bedroom, full bath, and flexible space for an office or sitting area. The lower level provides options for a playroom, exercise room, or office. Outdoor living shines with a bluestone patio accessed from the family room, perfect for entertaining. A detached two-car garage completes this exceptional property.

Completely renovated colonial style home on a quiet cul-de-sac within walking distance to downtown Winchester! This home features 5 bedrooms, 3.5 bathrooms and an attached 2 car garage. The first floor offers kitchen, dining, living room and den/study. The flexible first floor also has a bedroom with en suite bath and an office/additional bedroom. Completing the first floor are a half bath and full mudroom. The second floor has 3 generous bedrooms with ample closet space. The primary bedroom has a large walk in closet and spacious bathroom with dual sink vanity. Excellent yard space and back patio for exterior living.

Nestled in a desirable neighborhood, this home offers the opportunity to embrace the timeless elegance of the mid-century era. Lovingly maintained in its original condition, the ranch style provides the coveted option for one-level living. Enter the main level into the fireplaced living room, with large picture window and hardwood floors. Adjacent to the kitchen is the dining room with hardwood floors and window peeking into the family room, flooded with natural light and a cozy wood stove. Three comfortable bedrooms and full bath complete the main level. Additional features include the unfinished lower level with 3/4 bath, offering opportunity for additional finished space, and the convenience of a one car attached garage. Whether you're looking to restore it to its full glory or update it to your personal taste, this home offers endless potential while preserving its unique vintage appeal.

This inviting ranch house is cheerful and functional. Sunlight floods the open living and dining rooms, while custom plantation shutters offer privacy. Hardwood floors, a gas fireplace, and arched doorways add character and warmth to the space. The well-equipped kitchen features granite countertops, glass-front cabinetry and access to a side deck for al fresco dining. Three bright bedrooms and a full bath complete the 1st floor. The third bedroom, highlighted by wainscoting, is currently used as a den. The downstairs family room, complete with a wood-burning fireplace, a built-in bar and updated full bathroom, is perfect for recreation. The basement also offers ample storage, making it easy to keep your home organized. The even backyard is ready to host outdoor activities or quiet relaxation. Located in a highly sought after neighborhood, this home is 2 blocks from Ambrose Elementary School and just over a mile from the train station and Winchester's lively downtown. Welcome home!