West Side, MA homes for sale & real estate

West Side, MA Homes for Sale

Spacious 2-bedroom, 2-bath condo at Crescent Park offering 1,168 square feet of one-level living. This bright unit features an open-concept living and dining area with direct access to a private balcony. The kitchen includes ample cabinetry and a separate pantry. The primary bedroom offers a walk-in closet and en-suite bathroom. While the unit could benefit from some cosmetic updates, it presents a great opportunity to add value and personalize to your taste. Enjoy close by elevator access, nearby trash room, in-unit laundry, additional storage, a designated parking space, clubhouse, fitness room, and in-ground pool. Conveniently located on the Winchester/Woburn line, across from Sogno and

West Side, MA Homes for Sale

Royal Barry Wills former home! – An architectural treasure nestled on over 1 acre of land in one of Winchester’s most serene and private settings. Designed by the renowned architect Royal Barry Wills, this iconic Cape Cod residence showcases timeless elegance with its signature gambrel roof, cypress shingle exterior, and classic New England design. Inside, three magnificent fireplaces, exquisite millwork, and a beautiful stained-glass door create a sense of warmth and refinement. The inviting eat-in kitchen opens to a charming screened porch, perfect for quiet mornings or evening gatherings overlooking the lush rose gardens. Three spacious bedrooms w/ a large primary suite on t

West Side, MA Homes for Sale

Must see! Nestled along Winchesters beloved Winter Pond, this beautiful home offers a rare opportunity to live the waterfront dream just 7 miles from Boston! Featuring an oversized lot with breathtaking panoramic water views & offering a lifestyle that could include kayaking, paddle boarding, ice skating, fishing etc. .along with serenity and privacy so hard to find. This home offers ample living space that flows nicely between the formal living room, dining room, kitchen, office and family room, all of which have picturesque views. Many recent updates including kitchen, baths, roof, heating & de-leading; making this lovely home move in ready! 3 to 4 bedrooms, 2 1/2 baths w/ a f

West Side, MA Homes for Sale

Located on a peaceful street in the welcoming Morningside neighborhood, where kids still play in the streets, this 3-bed home has been thoughtfully expanded and updated. From the front door you'll be drawn immediately to the light filled great room with soaring ceilings, long leafy views, and access to the deck that provide seamless indoor/outdoor living. The chef's kitchen features birch cabinets, granite counters and stainless appliances. With three wood burning fireplaces, there are plenty of options for a cozy movie night. Privately situated down the hall is the primary with ensuite bath, two additional bedrooms, and family bath. The finished basement offers a 2nd family room, space for

West Side, MA Homes for Sale

Elegantly sited on Morningside Hill, this home is a luxury-built masterpiece. Thoughtfully designed & artfully crafted, it exudes opulence & cozy comfort. A gracious entry hall welcomes you into sophisticated living, highlighted by a breathtaking two-story living room adorned with countless windows. The chef's kitchen, a culinary haven, is equipped with state-of-the-art Thermador appliances, oversized island, coffee bar, walk-in pantry, & wine tower. A finished walk-out lower level is plumbed for a kitchen & offers versatile space for media, recreation, or future use as a separate living area. Ensuite bathrooms offer marble & designer finishes. You will love th

West Side, MA Homes for Sale

An extremely rare new construction in the Flats, this stunning 6BD/4.5BA home is a ground-up rebuild blending modern luxury with timeless warmth in one of Winchester’s most coveted neighborhoods. Designed for elevated living, it features a chef’s kitchen with quartz counters, custom cabinetry, a large island, and built-in bar, opening to a sunlit dining area ideal for both casual meals and elegant entertaining. The soaring family room stuns with cathedral ceilings, exposed beams, and a floor-to-ceiling stone fireplace—perfect for cozy evenings or lively gatherings. The serene primary suite offers a wood-accented ceiling, sitting area, and spa bath with dual vanities and a