Properties listed in Winchester

Imagine arriving home to peace & serenity at The Ledges, a hilltop oasis on Winchester's West side. This tranquil retreat offers carefree living & your private sanctuary. Relax in the fireplace living room, sliders to your private deck & expansive views. The main bedroom en suite, is conveniently located on the first floor. Second level…

Beautiful & magnificent, this colonial single family offers a perfect blend of timeless elegance and contemporary amenities. Situated at the end of a serene cul-de-sac & private hilltop oasis just minutes from the new Lynch Elementary School opening in 2025. Enjoy proximity to Horn Pond recreation areas & seasonal views of Winter Pond. Featuring 5…

Discover this beautiful split-level home featuring 4 spacious bedrooms and 2 bathrooms. The open floor plan seamlessly connects the inviting living room, dining area, and well-equipped kitchen, perfect for entertaining. Natural light floods the sunroom, offering a tranquil retreat that leads directly to a new deck ideal for outdoor relaxation. The main level boasts 3…

Welcome to this well loved 4-bedroom expanded Cape, on quiet cul-de-sac, cared for by the original owners for nearly 65 years! Located in the brand new Lynch Elementary School district, just steps from Winchester HS, Skillings Field, less than a mile from the Commuter Rail and downtown Winchester. Great for commuters. First floor features mudroom…

Back Bay meets Winchester in this victorian style attached residence in a premier Flats/ downtown location. This lovingly modernized home offers central air, first floor laundry, gas heating & cooking & tremendous closet space. The kitchen seamlessly transitions to the deck & huge manicured fenced in yard perfect for kids, pets & all outdoor fun.…

Welcome to this impeccably maintained & beautifully updated Colonial on large lot near the town center. This home blends charm w/ modern convenience, featuring 3 spacious bedrooms & 1.5 baths w/ a great floor plan. The first level features a sun-drenched living room that flows into an inviting dining room; updated kitchen overlooks the rear…

Fully renovated 4BR/4BA single-family home in Winchester with three levels of living space, ideal for remote work. Features include hardwood floors, quartz kitchen countertops, stainless steel appliances, custom vent hood, and first-floor laundry. Four brand-new tiled bathrooms. Basement walkout suite with full bath, kitchenette, and W/D hookup—great for in-law or au-pair. Mini-split cooling throughout, 2…

Fully furnished beautiful new construction home located on the West Side of Town and proudly situated on over an acre lot with gorgeous views! 5 bedroom 4.5 bath,5,820SF custom built colonial with three-car attached garage with side entrance into oversized mudroom. Main level features gourmet kitchen with high-endappliances, oversized island, dining area, adjacent family room…