Winchester, MA Homes for Sale under $2,000,000

Set back on a private, serene lot, this contemporary home offers peaceful nature views from nearly every window and a bright, open layout designed for effortless indoor-outdoor living. Cathedral ceilings, hardwood floors, two fireplaces, and French doors create inviting living and dining spaces that extend to decks and patios. The kitchen features teak cabinetry, stone counters, stainless

Anne Spry Barrett Sotheby's International Realty

Classic curb appeal abounds at this expansive five-bedroom colonial in the desirable Winchester Highlands neighborhood. The sun-filled first floor features a gracious floor plan with a thoughtfully designed eat-in kitchen showcasing premium appliances including a Sub-Zero refrigerator and Fisher & Paykel DishDrawer. A dining room, living room with wood-burning fireplace, office, mudroom and

Dara Singleton Better Homes and Gardens Real Estate - The Shanahan Group

Must see! Beautifully renovated & expanded Cape offering flexibility for multigenerational living, complete w/ a legal unit over the garage ideal for in-laws, nanny, guests, or rental income. Thoughtfully designed w/ a seamless blend of private & communal spaces, the main home features an updated kitchen w/ mudroom, laundry & pantry, a spacious living room w/ gas fireplace, dining room, 1st flr

Kim Covino Compass

Discover luxury & convenience in this impeccably maintained 8 room 2-3 bed, 2.5-baths unit in desirable Graystone!! A high end townhome community located just outside Winchester center offering a first floor primary suite! The gourmet kitchen showcases custom cabinetry, granite countertops, top-of-the-line stainless appliances w/new gas stove. The open-concept living & dining area w/ a gas

Kim Covino Compass

Sophisticated and comfortable, this updated Colonial offers beautifully scaled living spaces and a versatile floor plan designed for everyday living and entertaining alike. The sun-filled main level features hardwood floors, elegant architectural details and thoughtfully updated spaces. At the center of the home is a spacious eat-in kitchen with island, abundant prep space, and seamless access to

Pirani & Wile Group Gibson Sotheby's International Realty

Must see! sprawling 2-3 family beautifully renovated & expanded home offering flexibility for multigenerational living, complete w/ a legal unit over the garage ideal for in-laws, nanny, guests, or rental income. Thoughtfully designed w/ a seamless blend of private & communal spaces, the main home features an updated kitchen w/ mudroom, laundry & pantry, a spacious living room w/ gas fireplace,

Kim Covino Compass

Welcome to this spacious West Side home w/a versatile multi-level layout, offering ample room for comfortable living and entertaining. In the main level, you'll be greeted by a warm & inviting atmosphere, w/abundant natural light filtering through the windows. You enter a well-appointed kitchen, w/ample counter space, a breakfast nook and a french door access to the deck surrounded by tall trees.

Elaine Song Coldwell Banker Realty - Lexington

Don't miss this incredible opportunity to own a beautifully maintained 4-bedroom, 2 full bath, 2 half bath home in one of Winchester's most desirable locations. Designed for both everyday living and effortless entertaining, this home offers spacious living areas filled with natural light, an updated kitchen, generously sized bedrooms, and a versatile finished lower level perfect for a family

Team Lillian Montalto Lillian Montalto Signature Properties

Beautifully updated & impeccably maintained 3 BR, 3.5 bath home on a sought-after cul-de-sac w/lovely front & side yards, abutting conservation land for exceptional privacy. The main level features a spacious living room, updated sunroom, granite kitchen w/newer SS appliances, abundant cabinetry, peninsula seating, & dining room w/ access to an inviting deck. Two 1st floor bedrooms & two full

Paula Sughrue Better Homes and Gardens Real Estate - The Shanahan Group

This completely remodeled home is nestled on a dead end street off Brookside Road, offering a serene/ natural setting with unmatched privacy. This home offers 4 bedrooms, and 2.5 baths with three spacious finished levels. The completely reimagined open concept main floor features a stunning kitchen open to dining area and large family room, plus a separate living room, mudroom, half bath and

Kim Covino Compass

A rare Arlington home with a West Coast feel and a lifestyle you do not usually find in Massachusetts. Set above the street with elevated, treehouse-like living spaces, the second-floor main level is made for gathering, with an open living/dining area, wood-burning fireplace, renovated kitchen, and seamless access to an expansive deck for dinner parties, morning coffee, and summer nights outside.

Street Property Team Keller Williams Realty Boston Northwest