West Side Homes for Sale

Expanded Colonial Ranch offering over 5,000 sq ft of versatile living space, set on a beautifully landscaped 1/2-acre lot on a quiet cul-de-sac near Winchester Country Club. The first floor features a welcoming formal living room just off the entry, a spacious primary suite with two walk-in closets and a private bath, a guest bedroom with en-suite bath, and a third bedroom or home office.

Leigh Ventura Compass

Stunning 5BD/4.5BA contemporary estate on a private cul-de-sac in Winchester’s most coveted neighborhood. Modern design with soaring two-story ceilings, skylights, wide-plank hardwoods, and a dramatic stone fireplace. Gourmet chef’s kitchen with all-white waterfall island, Sub-Zero appliances, and butler’s pantry. Luxe primary suite with dual walk-in closet, spa bath, and private terrace. Fully

Andersen Group Realty Keller Williams Realty Boston Northwest

Stunning Absolutely! Custom-built 6-bedroom house on a large and tranquil lot. This beautiful home welcomes you with a magnificent 18" foyer and features an amazing family room with 18” high coffered ceilings and 3 sides tall and bright windows and a large gourmet kitchen with a big island and double ovens. Traditional living and dining room maintain its good sense of typical New England

Weidong Li WINN Real Estate & Consulting

Pristine Home nestled in Winchester's Sought After West Side Neighborhood and on a Cul de Sac! Open Floor Plan, Very Spacious Granite and Stainless Chef's Kitchen w/Breakfast Bar and Sun-filled Family Room featuring Floor to Ceiling Windows w/ French Doors open to New Composite Deck, Serene Level Backyard w/ Stone Patio, Lush Perennials and Mature Trees to Relax and Enjoy! Elegant Dining Room

Giordana Fiorvanti-Smith Berkshire Hathaway HomeServices Commonwealth Real Estate

This expansive contemporary residence exudes elegance & sophistication and offers the perfect layout for gatherings & everyday living. This gorgeous home, nestled into a cul-de-sac on the West side was custom designed with soaring ceilings & large scale rooms offering unparalleled views! Enjoy meals in the updated kitchen w/ high end appliances & direct access to deck overlooking private yard.

Kim Covino Compass

This stunning, freshly painted, home is located in a picturesque and unique setting, elevated on a small hill with a private half-acre lot in a tranquil cul-de-sac, near the Winchester/Lexington border. It’s far from road traffic, offering exceptional privacy. The residence spans four levels, featuring 5 bedrooms, 3.5 bathrooms, and two separate laundry areas. The expansive grounds showcase

Andersen Group Realty Keller Williams Realty Boston Northwest

Your very own private oasis tucked away in a cul-de-sac-like neighborhood just mins. to Winchester Center! Set on a deep, tree-lined lot, this stunning home offers 5 beds, 3.5 baths, & over 3,000 sq. ft. The versatile floor plan offers ground-level entry w/ a 2 car garage, 2 bedrooms (which can also function as work/play space,) & full bath/laundry area. The upper level is the heart of the home –

Gorfinkle Group eXp Realty

Welcome to The Ledges—an exceptional custom-designed “E” style end-unit townhouse offering over 10 rooms of refined living space and a distinctive layout found in no other unit. Thoughtfully maintained and tastefully updated, this residence features an expansive open floor plan with cathedral ceilings, elegant crown molding, and a gourmet chef’s kitchen equipped with premium appliances. The first

Ngoc Anh Goldstein Leading Edge Real Estate

Unleash Your Vision in Winchester’s Coveted West Side! Don't miss this rare chance to transform this Mid-Century Modern ranch on a generous 15,024 square foot idyllic lot in one of Winchester’s most desirable neighborhoods. Whether you renovate, expand, or enjoy this home as it is, this 3-bed, 1.5-bath home offers endless potential. Nestled on a quiet, tree-lined street abutting conservation land

Joanne Sexeny Coldwell Banker Realty - Lexington

Incredibly well maintained, nicely updated 3-4 bedroom Colonial in a wonderful neighborhood in desirable VO School district! The first floor has an oversized kitchen w/cherry cabinets, all granite counters & breakfast bar that opens to a great room with FP and a recently added family room w/vaulted ceiling, computer cubby and 10' slider to a deck overlooking a beautiful landscaped yard & 2

Hudson Santana Keller Williams Realty Boston Northwest

Stunning 5 bed 3.5 bath customized colonial situated on a gorgeous street with 1/2 acre lot! This sun-drenched home is filled w/ natural light & is perfectly designed for both everyday living & entertaining. The first floor features a spacious, updated kitchen w/ an oversized island, dining room w fplc & two beautiful great rooms on either side of the home w/ vaulted ceilings, skylights &

Kim Covino Compass

Come see this spacious 5-bedroom home offered at a NEW PRICE of $1,769,000! Located near the end of a quiet cul-de-sac in a wonderful neighborhood, this home offers privacy, space and natural beauty, just a short distance to Winchester Center and surrounding towns. Walking distance to the Vinson-Owen school, which has consistently been rated as one of the best elementary schools in the state.

Darryl Brian RE/MAX Bentley's

Renovated Contemporary Split-entry 3 Level home in the highly sought-after Vinson- Owen Elementary and West-side neighborhood. 15 minutes to Downtown Boston. 5 bedrooms, 2 full baths, Living, Dining PLUS family room & 2nd finished room ( play or office) ground level room heated & A/C walk access to outdoor deck & fire pit. Open concept kitchen area. Hardwood floors, 2 fireplace, 2 garage space,

salim chowdhury TAJ Mahal Realty LLC

Great value in Town! Discover the perfect blend of luxury and comfort in this stunning 6-bedroom home. Sunlight pours into the open-concept layout, highlighting a gourmet kitchen with stone countertops, an oversized island, and high-end Viking appliances. The inviting living room, featuring a shiplap fireplace, opens to a spacious composite deck. The primary suite is a private retreat with a

Alina Wang Coldwell Banker Realty - Lexington

Prepare to be captivated by the elegance of 11 Viking Rd. This magnificent home, boasting over 7,000 square feet of luxurious living space, offers an unparalleled opportunity for discerning buyers seeking the ultimate in comfort, style, and sophistication.Step inside and discover a world of meticulous details and thoughtful design. With 7 generously sized bedrooms and 7.5 exquisitely appointed

The McLaren D'Agostino Team Compass

Stunning 8800 sq ft brand-new contemporary in one of Winchester's favorite neighborhoods. A gracious foyer w/ high ceiling welcomes you to this elegant home loaded with natural light and architectural detail. Custom features include a gourmet eat-in kitchen w/ granite countertops, high-end appliances, secondary prep area, and fabulous outside dining options from the oversized deck. The

Dan Li Keller Williams Realty

This newly constructed home faces Old Village Dr. & redefines modern luxury! Designed w/ both elegance & everyday comfort in mind, this residence blends style w/ ease of living. The 8’ arched, handcrafted wrought-iron front doors open to a grand 20' foyer, showcasing soaring 10' ceilings, custom rift-sawn beams, and expansive floor-to-ceiling windows. With 25 years of expertise, the master

Kim Covino Compass