Winchester Homes with Colonial Style

Welcome to Winchester, Massachusetts—a charming town nestled in Middlesex County that perfectly blends historical charm with modern conveniences. Known for its picturesque landscapes, vibrant community, and top-rated schools, Winchester is an ideal destination for families and professionals alike. Just a short commute from Boston, this town offers the tranquility of suburban living while keeping you connected to the bustling city life.

One of the most captivating features of Winchester is its stunning array of Colonial-style homes. These timeless residences exude character and elegance, showcasing the rich architectural heritage that defines the area. With their classic symmetry, gabled roofs, and inviting front porches, Colonial homes in Winchester provide a warm and welcoming atmosphere that resonates with both history enthusiasts and modern homeowners. Many of these properties have been meticulously maintained or thoughtfully updated, blending traditional charm with contemporary amenities.

Living in Winchester means enjoying a vibrant community filled with parks, local shops, and a variety of dining options. The town’s commitment to preserving its historic charm while fostering growth is evident in its thriving downtown area and community events. Whether you’re strolling along the scenic streets or exploring the beautiful parks, you’ll quickly discover why Winchester is such a sought-after place to call home.

If you’re looking for a home that captures the essence of New England charm and offers a sense of community, Winchester’s Colonial-style homes are waiting to welcome you. Embrace the opportunity to live in this delightful town where history and modern living harmoniously coexist.

Newest Winchester Homes with Colonial Style

$1,799,000

3 Beds ⋅ 4 Baths ⋅ 73555777 MLS

Welcome home to this beautifully renovated gem, perfectly positioned on a corner lot in the highly sought-after LINCOLN ELEMENTARY SCHOOL district! Warm, inviting, and truly move-in ready, this home offers the open-concept first floor today’s buyers are looking for—featuring a stunning kitchen that flows effortlessly into the dining and living areas, plus a sunken family room ideal for relaxing or entertaining. Step outside to enjoy the beautifully fenced-in yard, offering a private outdoor retreat for play, pets, gardening, or gatherings. Everyday convenience continues with a mudroom located directly off the driveway, multiple off-street parking spaces, and a two-car garage. The finished lower level includes a full bathroom and versatile flex space perfect for a recreation room, home gym, playroom, or media room. Upstairs, you’ll find three bedrooms, including a lovely primary suite with a spacious bedroom, walk-in closet, and full bath. Thoughtfully renovated from top to bottom, this home features all new systems for peace of mind and effortless modern living. Located just a short walk to Winchester’s vibrant town center and commuter rail.

1 Town Way, Winchester

Listing courtesy of Listing Agent: Vita Realty Group from Listing Office: Compass.

$849,000

3 Beds ⋅ 2 Baths ⋅ 73555218 MLS

Walkable to nearly everything, 15 Clark St presents and exceptional opportunity to enjoy refined living in one of Winchester's sought-after neighborhoods. This sun-drenched duplex offers 3 bedrooms, 1.5 bathrooms, and approx 1,336 sq ft of thoughtfully curated living space. Rich hardwood and pine floors, soaring natural light, and an effortless flow in layout create a warm and sophisticated atmosphere. The beautifully appointed kitchen features modern appliances and generous space for everyday living and entertaining. Upstairs, the spacious primary bedroom is complemented by two additional bedrooms ideal for family, guests, or dedicated home office. Central A/C, second-floor laundry, and off-street parking enhance everyday convenience. Moments from Elliot Park, Middlesex Fells Reservation, top-rated schools, acclaimed restaurants, boutique shopping, Winchester commuter rail, and major routes, this home embodies the very best of Winchester living.

15 Clark St, Winchester

Listing courtesy of Listing Agent: Jeffrey Hsu from Listing Office: Coldwell Banker Realty - Milton.

$2,225,000

4 Beds ⋅ 4 Baths ⋅ 73554545 MLS

Rarely available in one of Winchester’s most desirable neighborhoods, this beautifully maintained Colonial offers the perfect blend of modern comfort and convenience. Set on a quiet cul-de-sac surrounded by historic homes, this late 1990s residence provides newer construction, a thoughtfully designed floor plan and an exceptional location just minutes from Winchester Center, commuter rail, Lincoln Elementary School and the Middlesex Fells Reservation with miles of trails, hiking, running and The Sheepfold dog park. The traditional yet open layout features an updated kitchen, spacious living and dining areas, refreshed baths, fresh paint and updated mechanical systems. A versatile bonus room with a private staircase offers endless possibilities as a home office, media room, guest space, playroom or fitness area. The finished lower level with half bath adds valuable living space. Enjoy outdoor living on the wraparound deck overlooking a private backyard with mature landscaping.

6 Davey Ln, Winchester

Listing courtesy of Listing Agent: Gretchen Papineau from Listing Office: Coldwell Banker Realty - Andovers/Readings Regional.

$1,150,000

4 Beds ⋅ 3 Baths ⋅ 73554139 MLS

Classic center-entrance Colonial set on a cul-de-sac with a wonderful sense of flow and everyday function. The main level offers formal living and dining rooms, a spacious front-to-back fireplaced family room with first-floor laundry and half bath, plus a bright kitchen with island, dining area, and direct access to the deck. Upstairs, the primary suite includes a walk-in closet and private bath, complemented by three additional bedrooms and a full bath. A two-car under garage connects to the unfinished basement, offering excellent storage and future possibilities. Central air, gas heat, hardwood floors, and a level lot complete this inviting home.

11 Williams Cir, Winchester

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

$1,599,000

4 Beds ⋅ 4 Baths ⋅ 73554036 MLS

New roof and fresh exterior paint just completed! This move-in-ready 4-bedroom, 2 full bath, 2 half bath home has been thoughtfully updated and meticulously maintained, offering the perfect blend of timeless charm, modern updates, and exceptional outdoor living in one of Winchester's most sought-after neighborhoods. Recent improvements include a brand-new roof, freshly painted exterior, all-new deck railings, a freshly painted finished lower level with brand-new carpeting, and the seller will replace the second-floor HVAC system, providing valuable peace of mind for the next owner. Inside, you'll find sun-filled living spaces, an updated kitchen, generously sized bedrooms, and a versatile finished lower level ideal for a family room, home office, gym, or playroom. The true showstopper is the spectacular backyard retreat. Designed for entertaining and everyday enjoyment, the private outdoor oasis features a heated saltwater pool with a beautiful waterfall, an expansive patio, mature landscaping, and an outdoor entertaining area rough-plumbed for a future outdoor kitchen—making it easy to create the backyard you've always envisioned. Ideally located just minutes from Winchester Center, top-rated schools, shopping, dining, parks, and commuter routes, this is a rare opportunity to own a turnkey home with outstanding updates, exceptional outdoor amenities, and an unbeatable Winchester location.

241 Ridge St, Winchester

Listing courtesy of Listing Agent: Team Lillian Montalto from Listing Office: Lillian Montalto Signature Properties.

$950,000

3 Beds ⋅ 1 Baths ⋅ 73549935 MLS

Warmth, charm, and an exceptional location come together in this inviting 3-bedroom home. Beautiful wood floors, natural woodwork, French doors, and custom built-ins add character throughout. Generous living spaces provide room to gather, relax, and entertain, while the home's classic appeal offers the perfect opportunity to enjoy today or personalize over time. A detached 2-car garage adds convenience and additional storage, and a half bath is located in the unfinished basement. Just 1 mile from Winchester Center, enjoy easy access to restaurants, coffee shops, boutiques, the public library, and commuter options with close proximity to Boston. The recently built elementary school and renovated high school feature state-of-the-art facilities. Nearby Horn Pond offers scenic walking trails, kayaking, birdwatching, and waterfront views.

47 Water Street, Winchester

Listing courtesy of Listing Agent: The Mary Scimemi Team from Listing Office: Leading Edge Real Estate.

$2,999,000

5 Beds ⋅ 4 Baths ⋅ 73548103 MLS

Must see this stunning move in ready waterfront gem! Perfectly sited at the end of Wedgemere on Winter Pond, offering over 80 feet of direct water frontage w/ expansive yard and breathtaking views from nearly every room. Located in the exclusive Flats neighborhood, this home presents a rare opportunity to enjoy water activities such as kayaking, paddle-boarding, fishing, ice skating and hockey all while being just minutes from Winchester Center and the train to Boston; homes like this rarely come to market. Custom designed and lovingly owned by the original family, this home is now ready for its next chapter. Offering a beautiful flowing layout w/ gleaming hardwood floors, large rooms, featuring floor-to-ceiling bay windows with stunning views, 5 bedrooms, 2 full & 2 half baths, 4 fireplaces, a walk-out lower level rec room, & a gorgeous fenced yard with steps to the water. Truly a special setting that seamlessly combines privacy, views & accessibility in Winchesters TOP neighborhood!

10 Dartmouth Street, Winchester

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

$1,064,000

4 Beds ⋅ 2 Baths ⋅ 73547513 MLS

Welcome to this meticulously renovated four-bedroom Colonial, ideally situated on a quiet dead-end street just steps from downtown Winchester, the commuter rail, and the newly built Lynch Elementary School. The sun-filled first floor features gorgeous floors, a charming living room, a dining room that opens to a spacious deck, a stunning updated kitchen with new countertops and appliances, as well as a mudroom and a full bath. The fenced backyard is perfect for entertaining. Upstairs, four bedrooms each offer generous closet space. The lower level--with new half bath, new carpet, laundry and storage--is ideal for a media space or playroom. Newer roof, tankless water heater, and a new 200-amp electrical panel provide peace of mind. Close proximity to Horn Pond Reservation, trails, and parks, and easy access to Boston via rail and bus. A rare chance to own a fully updated home in a truly special neighborhood.

46 Clark St, Winchester

Listing courtesy of Listing Agent: Andersen Group Realty from Listing Office: Keller Williams Realty Boston Northwest.

$1,899,000

5 Beds ⋅ 4 Baths ⋅ 73545952 MLS

Sophisticated and comfortable, this updated Colonial offers beautifully scaled living spaces and a versatile floor plan designed for everyday living and entertaining alike. The sun-filled main level features hardwood floors, elegant architectural details and thoughtfully updated spaces. At the center of the home is a spacious eat-in kitchen with island, abundant prep space, and seamless access to the patio and private backyard. A formal dining room, oversized fireplaced living room, first-floor bedroom, mudroom, and half bath provide both functionality and flexibility. Upstairs are two impressive primary suites with cathedral ceilings, walk-in closets, and private baths, along with two additional bedrooms, full bath, and laundry room. The finished lower level includes a spacious family room with fireplace and ample storage. An attached 2-car garage and a convenient location just minutes to Winchester Center’s vibrant shops, restaurants, commuter rail, and major routes.

79 Grove St, Winchester

Listing courtesy of Listing Agent: Pirani & Wile Group from Listing Office: Gibson Sotheby's International Realty.

$2,500,000

5 Beds ⋅ 3 Baths ⋅ 73544924 MLS

Welcome to 9 Plymouth Rd — a classic 1959 single-family home tucked at the end of a private road on a dead-end street, set on a private 0.52-acre lot abutting conservation land in one of Winchester's most sought-after neighborhoods. This well-appointed 11-room residence offers 5 bedrooms, 3 full baths, and 1 half bath, giving your family room to spread out and settle in. Thoughtfully updated for year-round comfort, the home features central AC, central humidification, and an air exchanger. Outside, enjoy beautifully landscaped gardens, a spacious deck overlooking the private yard, lush irrigated grounds with an invisible dog fence, and a hot tub for unwinding after a long day. A wood-burning fireplace adds warmth and character to the living space. Located just minutes from top-rated schools, Winchester Center, and convenient commuter access to Boston, this is a rare opportunity to enjoy privacy, nature, and timeless New England living in an exceptional location.

9 Plymouth Rd, Winchester

Listing courtesy of Listing Agent: Steph Crawford Group from Listing Office: Real Broker MA, LLC.

$1,350,000

4 Beds ⋅ 3 Baths ⋅ 73541775 MLS

Architecturally distinctive and beautifully renovated throughout, this unique home blends historic character with the comfort of modern living. The inviting living room is enhanced by a large bay of windows and seamlessly connects with the dining room featuring classic wainscoting, and a decorative fireplace. The thoughtfully updated kitchen offers granite countertops, SS appliances, a breakfast bar island, laundry, and steps out to the deck and fully fenced, private backyard. A versatile main level bedroom provides direct access to the first of three full bathrooms, while the primary suite on the second level offers a walk-in closet and an updated bathroom with a dual sink vanity and tiled shower. French doors open to the inviting family room with a bay window. Set on a large corner lot with two driveways and a detached two-car garage accessed from quiet Englewood Road, this home offers a prime location moments from the Fells Reservation, the town center, commuter rail, and Muraco ES.

423 Washington St, Winchester

Listing courtesy of Listing Agent: Danielle Fleming from Listing Office: MA Properties.

$999,900

4 Beds ⋅ 2 Baths ⋅ 73541288 MLS

A rare Winchester opportunity under $1M, 258 Cross Street blends timeless character, meaningful updates, everyday function, and exciting long-term upside. Set on a level, fenced corner lot, this 4 bed, 2 bath Colonial offers the space buyers need today with the flexibility to evolve over time. Inside - hardwood floors, crown molding, arched openings, bay windows, and detailed trim add warmth, while the updated kitchen features stone counters, upgraded cabinetry, stainless appliances, gas cooking, and great natural light. Both full baths have been tastefully updated, including a larger bath with double vanity, tiled shower, and soaking tub. Four bedrooms on the upper levels create options for guests, office, fitness, hobbies, or future needs. Brand new AC, central heat, full basement with laundry/storage, patio, fenced yard, shed, and 4-car parking add real utility. Previously prepared conceptual expansion plans are available for review. Minutes from the iconic, and picturesque downtown

258 Cross Street, Winchester

Listing courtesy of Listing Agent: Justin Blankenship from Listing Office: Fiv Realty Co.

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