Winchester Homes with Cape Style

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

$1,299,000
4 Beds ⋅ 2 Baths ⋅ 73574477 MLS
Custom-built and thoughtfully designed for comfortable one-level living, this spacious ranch offers a flexible floor plan, ample living spaces, and convenient access to the walking trails and recreational amenities of nearby Horn Pond. The main level features a gracious formal living room with a wood-burning fireplace, an elegant dining room with custom paneling, and an updated eat-in kitchen with direct access to the picturesque backyard. Three generously sized bedrooms and a full bath complete the main level. Upstairs, a fourth bedroom is complemented by an unfinished storage room with excellent potential for a fifth bedroom, home office, or additional living space.The walkout lower level adds even more flexibility with a family room featuring a second fireplace, half bath, dedicated laundry room, mudroom, and direct access to the oversized two-car garage. Two additional storage areas provide the opportunity to create a home office, gym, playroom, workshop, or finished living space. With substantial square footage throughout, there is plenty of room to adapt the home to your needs. Beautiful custom moldings, well-proportioned rooms, abundant natural light, and a well-designed floor plan add warmth and character throughout. Recent improvements include a new roof, spray foam insulation, updated windows, and newer appliances. Outside, the park-like backyard is a true retreat, highlighted by a spectacular 20' x 40' in-ground pool, patio area, and exceptional privacy while abutting the Lynch School fields. Just moments from the Horn Pond Recreation Area, enjoy convenient access to walking trails, scenic views, playgrounds, fishing, and year-round outdoor recreation. With the newly constructed Lynch Elementary School nearby, along with shopping and major commuting routes, this home offers an ideal blend of privacy, recreation, and everyday convenience.

253 Pond St, Winchester

Listing courtesy of Listing Agent: Pirani & Wile Group from Listing Office: Gibson Sotheby's International Realty.
$1,699,000
3 Beds ⋅ 2 Baths ⋅ 73572661 MLS
Extensively rebuilt and expanded, this impeccably maintained 3/4 Bed 2 BA home offers a spacious and versatile floor plan. The impressive 28’ x 20’ great room features vaulted ceilings, bay window, and a gas fireplace which flows nicely from the updated kitchen. Step outside to a new oversized Azek deck with plenty of room for grilling, dining, and relaxing. The main level also includes formal living and dining rooms, plus a bedroom & full bath. The formal dining room offers flexibility to serve as a fourth bedroom, if desired. Upstairs are two generously sized bedrooms with hardwood floors and ample closet space, along with a spacious hall bath featuring a skylight. Additional highlights include a finished lower level, laundry and storage areas, and direct access to a two-car garage. Beautifully landscaped grounds feature perennial gardens, flowering trees, natural stone walls, and exceptional privacy—nestled into one of Winchester’s most desired neighborhoods, all just 7 miles from Boston with convenient access to the town center, Fells trails, major routes and highways. Please see feature/ update list attached.

4 Churchill Road, Winchester

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