Winchester Homes with Cape Style

Welcome to Winchester, Massachusetts—an enchanting town nestled in Middlesex County, just a stone's throw away from the vibrant city of Boston. Known for its picturesque streets, rich history, and a strong sense of community, Winchester offers an idyllic setting for those seeking a blend of suburban tranquility and urban convenience. With its charming downtown filled with boutique shops, delightful eateries, and lush parks, it's no wonder that Winchester is often regarded as one of the best places to live in the state.

One of the standout features of Winchester's real estate market is its stunning collection of Cape-style homes. These quintessential New England residences are characterized by their steeply pitched roofs, dormer windows, and inviting front porches, exuding a timeless appeal that resonates with both history enthusiasts and modern families alike. Cape-style homes in Winchester often boast spacious layouts, perfect for entertaining guests or enjoying cozy family gatherings. Many of these homes have been lovingly updated to include modern amenities while preserving their classic charm, making them a perfect fit for today’s discerning buyers.

Living in Winchester means access to top-rated schools, beautiful parks, and a tight-knit community that hosts year-round events. Whether you’re strolling along the scenic Mystic Lakes or exploring the historic sites, you’ll find that Winchester is a place where memories are made. If you’re considering a move to this delightful town, a Cape-style home could be your perfect sanctuary, offering both character and comfort in a community that feels like home.

Newest Winchester Homes with Cape Style

$1,699,000

3 Beds ⋅ 4 Baths ⋅ 73549106 MLS

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 baths, including an en-suite, offer exceptional flexibility. The 2nd floor primary suite is a private retreat w/ a vaulted ceiling, oversized walk-in closet, spacious bath w/ double vanity. This level offers an additional storage closet & unfinished room w/expansion potential. En-suite bedrooms on both the 1st & 2nd floors provide a versatile floor plan. The bright walk-out lower level includes a large family room w/ access to an expansive deck, mudroom, laundry room, half bath, & bonus room ideal for overnight guests. Replacement windows & beautiful storage shed complete this move in ready home.

2 Olde Lyme Road, Winchester

Listing courtesy of Listing Agent: Paula R. Sughrue from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.

$1,899,000

6 Beds ⋅ 5 Baths ⋅ 73507137 MLS

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, dining room, 1st flr bedrm & full bath, plus a flexible suite w/ kitchenette, sitting room & full bath. Upstairs offers 3 add' bedrooms & a full bath. The finished lower level includes a family room, office, exercise space, bonus room w/ walkout, workshop, storage & cedar closet. Additional highlights include an oversized 2-car garage with EV charger, elevator lift, solar array, & direct access to the apartment featuring vaulted ceilings, gas fireplace, full kitchen, laundry & private deck. Set on an oversized level lot with mature landscaping, deck, patio & gazebo on a quiet cul-de-sac!

16 & 16A Glenwood Ave, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.

$929,900

4 Beds ⋅ 2 Baths ⋅ 73498603 MLS

This Expanded Cape features a fireplace living room, built in bookcases, and glistening hardwood floors throughout. The spacious kitchen has a dining area which opens to the living room for an entertaining atmosphere. The 2nd floor Master bedroom suite has a balcony to enjoy your morning coffee. The inviting 3 season porch with flagstone floor is a nice place for family to congregate and get to gather. The living room, graced with crown molding, offers a welcoming space for relaxation and entertainment. The home features four bedrooms and two full bathrooms, providing ample space for a comfortable lifestyle. The inclusion of a walk-in closet adds a practical and desirable element, offering generous storage and organization. Please come and visit this fine home close to shops, highways and schools!

380 Cross Street, Winchester

Listing courtesy of Listing Agent: Rajive Dogra from Listing Office: Coldwell Banker Realty - Lexington.

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