Winchester Homes with Cape Style

Welcome to Winchester, a charming town located in Middlesex County, Massachusetts. Known for its picturesque New England charm, Winchester offers a perfect blend of small-town tranquility and urban convenience. With top-rated schools, beautiful parks, and a thriving community, Winchester is a highly sought-after place to call home.

If you appreciate classic Cape Cod architecture, you'll feel right at home in Winchester. Cape-style homes are a common sight in this area, characterized by their cozy and inviting design. These homes typically feature steep roofs, dormer windows, and a symmetrical facade, giving them a timeless appeal that never goes out of style.

Whether you're looking for a quaint Cape-style home or a modern property with all the amenities, Winchester has something to offer for every homebuyer. From historic residences with character to newly constructed houses with sleek finishes, the real estate market in Winchester is diverse and vibrant.

If you're considering making Winchester your new home, reach out to a local real estate agent who can help you explore the available options and find the perfect property to suit your lifestyle. Don't miss the opportunity to experience the beauty and warmth of Winchester living – it's a decision you won't regret.

Newest Winchester Homes with Cape Style

$1,985,000

4 Beds ⋅ 4 Baths ⋅ 73589478 MLS

Set on over an acre of beautifully landscaped grounds abutting acres of woodland, this extensively renovated Contemporary Cape offers exceptional privacy and a peaceful connection to nature. A thoughtfully designed open floor plan features hardwood floors, a fireplaced living room, elegant dining room, and a beamed-ceiling family room adjoining the remodeled kitchen with stone counters, stainless appliances, and island. A private great room off the foyer, with windows on three walls and a slider to the spacious deck, offers a wonderful retreat. French doors open to the expansive deck overlooking the fenced backyard and wooded surroundings. Upstairs, four bedrooms include a primary suite with custom closets and private bath. The finished walkout lower level offers flexible space for a home office, gym, or guests, with separate entrance and full bath. Stone walls, mature landscaping, a long private driveway, and two-car garage complete this exceptional home.

30 Surrey Rd, Winchester

Listing courtesy of Listing Agent: Anne Spry from Listing Office: Barrett Sotheby's International Realty.

$1,999,000

5 Beds ⋅ 4 Baths ⋅ 73588059 MLS

Welcome to this beautifully appointed and exceptionally spacious home, ideally situated in a quiet, desirable West Side Winchester neighborhood within the sought-after Vinson-Owen School district. Offering an impressive combination of elegant living spaces, flexible accommodations, and thoughtful upgrades, this home provides room for everyone while easily adapting to a variety of lifestyles. At the heart of the home is the expansive granite kitchen, designed for both everyday living and entertaining. Custom cabinetry, Thermador double ovens, a Dacor warming drawer, Sub-Zero refrigerator, wine refrigerator, recessed lighting, and an impressive 50-square-foot center island create a wonderful gathering space with plenty of room for cooking, dining, and entertaining. The kitchen flows into a comfortable family room featuring a custom-built entertainment center and electric fireplace. A gracious formal dining room showcases handcrafted molding and classic wainscoting, while additional first-floor living spaces provide tremendous flexibility for a formal living room, playroom, home office, den, or whatever best suits your needs.One of the home's most appealing features is the first-floor bedroom suite with a full bath, offering exceptional versatility for extended family, guests, an au pair, or anyone seeking the convenience of first-floor living. A dedicated laundry room on this level adds even more functionality. With multiple living areas and flexible rooms throughout the first floor, there are countless ways to create private spaces for additional family members while still enjoying plenty of room to gather together.Upstairs, the generously sized primary suite provides a relaxing retreat with vaulted ceilings, recessed lighting, double closets, and a beautifully tiled private bath with double sinks. Three additional spacious bedrooms, another full bath, and additional office space provide abundant room for family, guests, work-from-home needs, hobbies, or study areas.With its generous proportions, flexible floor plan, multiple bedroom and living configurations, and outstanding West Side location, this is a home designed to grow and change with its owners. Enjoy the peace and privacy of a quiet neighborhood while being part of the wonderful Winchester community. This is more than simply a beautiful house—it is a home offering the space, versatility, and comfort today's buyers are looking for.

21 Amberwood Dr, Winchester

Listing courtesy of Listing Agent: Gayle Winters & Co. Team from Listing Office: Compass.

$1,325,000

4 Beds ⋅ 2 Baths ⋅ 73579538 MLS

1st OPEN HOUSE! SUNDAY, OCTOBER 4th, 11:30am-1:00pm! Timeless New England charm meets prime Winchester living at 9 Priscilla Lane. Tucked along a quiet, tree-lined neighborhood on Winchester’s East side, this inviting 4-bedroom home offers the perfect balance of suburban tranquility, outdoor adventure, and seamless connectivity.Inside, the sun-drenched home features rich hardwood floors, a gorgeous kitchen, wood burning fireplace, flexible living areas, and an intuitive layout designed for both daily relaxation and effortless entertaining. Step outside to an expansive, private backyard—a sunlit haven perfect for weekend barbecues, garden projects, or crisp New England evenings.Outdoor enthusiasts will love living moments away from the endless hiking, trail running, and scenic escapes of the Middlesex Fells Reservation. For commuters, rapid access to I-93 and Route 128/I-95, combined with nearby Commuter Rail stations, makes reaching Boston, Cambridge, or local tech hubs exceptionally fast and direct. Complete with proximity to top-rated Winchester public schools and vibrant downtown dining and shops, this property delivers the quintessential North Shore lifestyle in an unmatched location. MAKE 9 PRISCILLA LANE YOUR HOME TODAY!

9 Priscilla Ln, Winchester

Listing courtesy of Listing Agent: Robert Del Greco from Listing Office: Compass.

$1,599,000

4 Beds ⋅ 2 Baths ⋅ 73572661 MLS

Price Change!! **Open House this weekend or call for private showings** Great offering~ Extensively rebuilt and expanded, this impeccably maintained 4 Bed 2 BA home offers a spacious and versatile floor plan. The impressive 28’ x 20’ great room w/living area and dining area 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 room w/ fplc, plus 2 spacious bedrooms & full bath. offering flexibility for various uses. Upstairs are two additional generously sized bedrooms with hardwood floors and ample closet space, along with a full 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

Private showings available! Resort living just steps from the town center! Completely remodeled with 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 primary 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.

Start Your Search

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

Winchester Homes with Cape Style

Newest Winchester Homes with Cape Style

How much is your home worth?

How much is your home worth?