Winchester Homes with Cape Style

Welcome to Winchester, Massachusetts – a charming town nestled in the heart of Middlesex County, just a stone's throw away from the vibrant city of Boston. Known for its rich history, picturesque landscapes, and tight-knit community, Winchester offers a perfect blend of suburban tranquility and urban convenience. With its tree-lined streets, beautiful parks, and top-rated schools, it’s no wonder that families and professionals alike are drawn to this enchanting locale.

One of the standout features of Winchester's real estate market is its stunning collection of Cape-style homes. These delightful residences, characterized by their steeply pitched roofs, dormer windows, and cozy layouts, exude charm and warmth. Whether you’re a first-time homebuyer or looking to downsize, Cape-style homes in Winchester provide an inviting atmosphere, perfect for creating lasting memories with family and friends.

Many of these homes are set on spacious lots, offering ample outdoor space for gardening, play, or simply enjoying the tranquil surroundings. Inside, you’ll find well-designed floor plans that maximize both comfort and functionality, often featuring charming details like hardwood floors, built-in shelving, and inviting fireplaces.

Living in Winchester means embracing a lifestyle filled with community spirit and recreational opportunities. Residents enjoy easy access to local shops, restaurants, and cultural attractions, along with a variety of outdoor activities, from hiking in the nearby Middlesex Fells Reservation to enjoying summer concerts in the park.

If you’re searching for a home that combines classic New England charm with modern amenities, look no further than Winchester’s Cape-style homes. Experience the warmth and allure of this historic town, where every street tells a story and every home welcomes you with open arms.

Newest Winchester Homes with Cape Style

$1,549,000

3 Beds ⋅ 3 Baths ⋅ 73556633 MLS

Completely remodeled with exceptional custom finishes throughout, this stunning expanded cape with 3 levels, 3/4 bedrooms, 2.5-baths will exceed your expectations. The first floor features a spacious bedroom w/ full bath, an inviting living room w/ beautiful fireplace surrounded & custom built-ins, while the chef's kitchen is designed to impress with high end finishes, a large island and vaulted breakfast nook. The open floor plan flows into the dining room, complete with a custom built-in wine bar, ensuring easy entertaining. The second floor provides two very large bedrooms with great closet space and a tastefully remodeled hall bath. The beautifully finished lower level offers incredible flexibility with a cozy family room, kitchenette, laundry and 1/2 bath, with potential for a 4th BR, making it ideal for entertaining, guests, or extended living space. Step outside to an extraordinary backyard that feels like a resort! Enjoy the professionally landscaped grounds, lush gardens, and an expansive patio creating the ultimate outdoor oasis-featuring a built-in grill, pizza oven, bar seating, a hot tub, greenhouse, and shed. The retractable awnings make for comfortable shaded entertaining. It is truly a backyard that you will use all year round! Ideally located just outside Winchester center, enabling you to enjoy all the benefits of being close to town! This turn-key home is a must see, don't miss this one of a kind, move in ready home with so many recent upgrades!

50 Holland Street, Winchester

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

$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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