Winchester Homes with Colonial Style

Welcome to Winchester, Massachusetts – a charming town nestled in Middlesex County, known for its picturesque landscapes, vibrant community, and rich history. Just a short drive from Boston, Winchester offers the perfect blend of suburban tranquility and urban accessibility. With its tree-lined streets, award-winning schools, and a bustling downtown filled with boutique shops and cozy cafes, this town is an ideal place to call home.

One of the standout features of Winchester is its stunning collection of Colonial-style homes. These timeless residences reflect the town's historical roots and architectural elegance, showcasing classic features such as symmetrical facades, gabled roofs, and inviting front porches. The Colonial homes in Winchester offer a sense of grandeur and warmth, making them perfect for families and individuals seeking a welcoming atmosphere. Many of these homes have been meticulously maintained or thoughtfully updated, providing modern amenities while preserving their historic charm.

Living in Winchester means enjoying a close-knit community with a variety of recreational activities. Residents can explore the beautiful parks, join local sports leagues, or take leisurely strolls along the scenic shores of the Mystic Lakes. The town also hosts numerous cultural events and festivals throughout the year, fostering a strong sense of camaraderie among neighbors.

Whether you’re drawn to the historical allure of Colonial architecture or the vibrant lifestyle of Winchester, this town offers a unique opportunity to experience life in a beautiful, thriving community. Discover your dream home in Winchester and become part of a legacy that celebrates both history and modern living.

Newest Winchester Homes with Colonial Style

$1,599,000

3 Beds ⋅ 2 Baths ⋅ 73590582 MLS

Set on a quiet cul-de-sac in a sought-after Winchester location, 4 Harrington Road is a picture-perfect home that combines timeless appeal with thoughtful updates and an easy, comfortable layout. Just moments from downtown Winchester, multiple commuter rail stations, local schools, and more, the location offers the perfect balance of convenience and neighborhood charm. The first floor is warm and welcoming, featuring a renovated kitchen with breakfast bar, a formal dining room, and a fireplaced family room that opens to a beautiful three-season sunroom. Overlooking the expansive, level backyard, the sunroom is a standout space for morning coffee, casual gatherings, or simply enjoying the outdoors. A full bathroom and dedicated home office add flexibility to the main living level. Upstairs, three bedrooms and a full bathroom provide comfortable accommodations, with the primary bedroom offering direct access to the bath. The lower level presents an opportunity to create additional living space tailored to your needs. A fireplaced room offers a natural starting point for a future family room, while a separate bonus room with laundry could become a playroom, home gym, or creative retreat. With its inviting character, versatile spaces, and exceptional location close to everything Winchester has to offer, 4 Harrington Road is one you will not want to miss!

4 Harrington Road, Winchester

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

$1,399,000

5 Beds ⋅ 2 Baths ⋅ 73588977 MLS

Welcome to 15 Lloyd Street, ideally situated in one of Winchester’s most desirable neighborhoods! This charming, recently updated Colonial offers 5 bedrooms, 1.5 baths, and a flexible layout with plenty of space for everyday living, working from home, and entertaining. The inviting sun-drenched living room features high ceilings and opens to the dining room which has slider access to a large deck, along with an eat in kitchen, 1/2 bath and spacious entry foyer blending together to create a warm and welcoming home to enjoy. The second floor features 4 bedrooms including a spacious primary along with a full hall bath. An additional bedroom and office add great bonus space on the third floor. Some recent 2024 updates include new roof, heating system/HVAC, rebuilt front porch, updated electrical, all new hardwood floors, new window and baseboard trim in LR/FR & more! Walk out lower level offers laundry area & provides potential for future expansion/ family, game room. Additional highlights include a detached garage, off-street parking, and lovely yard to enjoy. Conveniently located in the heart of downtown Winchester close to parks, public transportation, and all that Winchester has to offer. This is a wonderful opportunity to enjoy the charm and convenience of this great home located in one of the town’s most sought-after neighborhoods! **Open houses Saturday & Sunday 1-2:30 both days!** 10/10 & 10/11 please stop by!

15 Lloyd Street, Winchester

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

$2,199,000

6 Beds ⋅ 5 Baths ⋅ 73588192 MLS

This distinguished residence on one of Winchester's most notable streets is a celebration of grand proportions, exquisite period craftsmanship, and timeless architectural beauty. High ceilings, four fireplaces, original hardwood floors, and beautifully scaled rooms create a sense of elegance that is increasingly difficult to find. The grand dining room is full of original details, anchored by a large fireplace and a big picture window that fills the room with natural light. A gracious living room offers another fireplace, beautiful hardwood floors, and impressive ceiling height, providing an elegant setting equally suited to intimate evenings and large-scale entertaining. A handsome first-floor study and south-facing sunroom offer quieter retreats, while the original butler’s pantry, complete with its own marble sink and original cabinets, speaks to the home’s history and the gracious way in which it was designed to be lived in. Six bedrooms + three full baths provide exceptional flexibility across the upper levels, with generous proportions and architectural details continuing throughout the home. Bonus space on the top floor and in the partially-finished basement provides room for a second home office, media room, gym or in-law space. The large patio offers privacy and entertaining space, while the grassy backyard has ample room to play. A rare three-story garage, originally designed with both chauffeur's quarters and a greenhouse, presents intriguing possibilities for the next owner. Set along prestigious Everett Avenue, in the Ambrose School District, it's a quick stroll to the town center, bus to Alewife, or Wedgemere Train Station. This residence offers an opportunity to become the next steward of a home whose craftsmanship, scale, and character simply cannot be replicated today.

42 Everett Ave, Winchester

Listing courtesy of Listing Agent: The Pallotta Group from Listing Office: Gibson Sotheby's International Realty.

$2,049,000

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.

$2,399,000

4 Beds ⋅ 4 Baths ⋅ 73587441 MLS

Stately and beautifully built brick Colonial in a premier Flats location, set on a gorgeous, level corner lot just under half an acre. Gracious proportions, soaring ceilings, hardwood floors, beautiful moldings, and exceptional architectural detail are showcased throughout all three levels. The welcoming first floor features a front-to-back living room with fireplace, generously sized dining room, spacious kitchen with center island and eat-in area, study, half bath, sun porch, and convenient first-floor laundry. Upstairs are four large bedrooms, including a spacious primary suite with private ensuite bath, plus a full family bathroom. The finished lower level offers even more living space with hardwood floors, a family room with fireplace, half bath, and bonus room, perfect for a playroom, gym, or home office. Two-car garage, central air, newer heating system, newer roof, and ample storage add to the home's comfort and convenience. A wonderful opportunity to own a substantial and elegant home in one of Winchester's most coveted neighborhoods.

63 Wedgemere Avenue, Winchester

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

$18,000,000

6 Beds ⋅ 7 Baths ⋅ 73585235 MLS

A NEW BENCHMARK FOR LUXURY LIVING IN WINCHESTER. Introducing a truly one-of-a kind estate—an extraordinary new residence created without compromise on approximately one private acre at the end of a cul-de-sac. Encompassing nearly 10,000 SF, 21 rooms, 6 bedrooms and 7 baths, this remarkable property brings together architectural presence, exceptional craftsmanship, advanced technology and resort-caliber amenities rarely found in a single Greater Boston residence.Beyond its gated entrance and heated driveway, sophisticated interiors unfold through grand entertaining spaces, a statement chef’s kitchen, library/office with wet bar, glass-enclosed fitness studio, acoustically designed cinema, wine lounge and underground wine cellar. The exceptional primary suite features a luxurious dressing room and dramatic two-tier panoramic veranda overlooking the grounds.Outside, the estate transforms into a private resort: spectacular pool with waterfall, integrated spa, flame features and automatic cover; covered outdoor kitchen; sunken conversation lounge with central fire feature; covered dining terrace with fireplace; and beautifully designed grounds offering extraordinary privacy.Behind the elegance is equally impressive infrastructure: 18 heating zones, 9 cooling zones, 600-amp electrical service, approximately 2.5M BTU gas capacity, integrated AV/security, automated gated entry and a 3-car climate-conscious auto lounge with porcelain flooring and dual EV charging.Minutes from Winchester Center and convenient to Boston, this is far more than exceptional new construction. It is a meticulously conceived private estate where architecture, technology, wellness, entertainment and resort living converge—created for the buyer seeking something that simply cannot be replicated.

15 Vinson Circle, Winchester

Listing courtesy of Listing Agent: Anthony Marino from Listing Office: The Marino Group Collection.

$3,299,000

7 Beds ⋅ 8 Baths ⋅ 73585058 MLS

Ideally situated in one of Winchester’s most serene neighborhoods, this exceptional residence offers impressive scale, thoughtful design, and remarkable versatility in a quiet, peaceful setting. It also represents one of Winchester's best values, with tremendous square footage and an au-pair/in-law apartment. Surrounded by beautiful homes and a sense of established elegance, this is a property designed to feel both private and welcoming. Thoughtfully expanded and beautifully built, the home offers 7 bedrooms and 7.5 baths, with generous living spaces designed for both everyday comfort and effortless entertaining. At the heart of the home, a stunning chef’s kitchen opens seamlessly to a dramatic fireplaced living room with soaring cathedral ceilings, creating a warm and inviting gathering space filled with natural light. There is also a family room, also with a fireplace and large picture windows, allowing for an abundance of sunlight. Explore further and you'll find a huge butler's pantry, a must-have feature in today's homes. There is also a wet bar with a beverage fridge. This is a home that has been very thoughtfully designed for how today's buyers actually live, but what truly distinguishes it is the flexibility of design. A private two-bedroom suite offers its own living area, office, wet bar, and full bath, providing an exceptional option for an au pair, extended stays, guests, returning college students or a more private living arrangement. The finished lower level adds even more space for recreation, fitness, entertaining, or simply spreading out. Beautifully proportioned rooms, exceptional functionality, and a serene neighborhood setting come together to create a home that feels substantial yet comfortable, sophisticated yet wonderfully livable. The natural light is exceptional, and outside, an oversized lot offers plenty of play space and a deck to hang out on. Just moments from Mullen Field, close to the town center and trains and an easy trip to Lexington or Cambridge, 1 Plymouth offers a rare opportunity to enjoy exceptional space and privacy in one of Winchester’s most sought-after neighborhoods.

1 Plymouth Rd., Winchester

Listing courtesy of Listing Agent: The Pallotta Group from Listing Office: Gibson Sotheby's International Realty.

$1,529,000

4 Beds ⋅ 4 Baths ⋅ 73584817 MLS

An exceptional opportunity in one of Winchester’s most desirable neighborhoods, directly across from the Winchester Country Club. Set on a beautiful .39-acre lot, this distinctive 4-bedroom, 3.5-bath Colonial offers approximately 2,709 sq. ft. of living space, a 2-cargarage, generous room proportions, and a flexible floor plan ready for its next chapter. Offering wonderful possibilities with its generous proportions, flexible floor plan, and impressive setting, the property presents an ideal canvas for buyers looking to renovate and personalize a home to their exact vision. Reimagine the existing spaces with sophisticated modern finishes, create a timeless renovation that complements the home’s character, or explore the possibilities for a more extensive transformation. The spacious lot also provides plenty of room to enhance the outdoor experience with thoughtfully designed landscaping, gardens, patios, entertaining areas, or other outdoor amenities. Beyond the property itself, the location stands out, with the Winchester Country Club just across the street and downtown Winchester conveniently nearby, offering restaurants, cafés, shops, services, and commuter rail access to Boston. Convenient access to Winchester public schools, major routes, and nearby public transportation makes commuting and exploring the Greater Boston area easy. Bring your architect, contractor, and creativity and transform this property into something truly special. With its substantial lot, desirable neighborhood setting, proximity to downtown, and access to everything Winchester has to offer, 25 Arlington Street presents a rare chance to create a home that reflects your own style in an exceptional location.

25 Arlington St, Winchester

Listing courtesy of Listing Agent: Domingo Medina from Listing Office: Coldwell Banker Realty - Lexington.

$1,950,000

5 Beds ⋅ 4 Baths ⋅ 73584117 MLS

Welcome to 26 Mayflower Road, located in one of Winchester’s sought-after neighborhoods alongside Winchester Country Club. From the beautifully landscaped grounds to the updated front door, garage doors, and recently redone front steps, this home offers wonderful curb appeal from the moment you arrive. Inside, the main level is warm, inviting, and filled with natural light, featuring a comfortable living room with wood-burning fireplace, an open kitchen and dining area, and a sun-filled family room that opens directly to a private brick patio. Whether you're enjoying your morning coffee, grilling, gathering with friends, or simply relaxing at the end of the day, the indoor-outdoor flow makes this home especially easy to enjoy. The spacious primary suite offers double closets and a beautiful bath with double vanity sinks, soaking tub, and tiled walk-in shower. An attached guest/in-law suite with its own private entrance, full bath, and kitchenette provides exceptional flexibility for guests, extended family, an au pair, or a private work-from-home space. The finished lower level adds even more room to spread out, with two additional living spaces and a full bathroom—perfect for a teen suite, home office, gym, playroom, or media space. Outside, beautiful landscaping, irrigation, and the expansive brick patio create a private setting for entertaining or simply enjoying the outdoors. Ideally located near commuter routes, the MBTA Commuter Rail, shopping, restaurants, schools, and downtown Winchester, this is a home that offers the space and flexibility to fit the way you live, all in a location that makes getting where you need to go easy.

26 Mayflower Road, Winchester

Listing courtesy of Listing Agent: Nicole M. Condon from Listing Office: The Simply Sold Realty Co..

$1,195,000

3 Beds ⋅ 2 Baths ⋅ 73582171 MLS

Introducing 4 Stone Ave, a charming 3 bed, 1.5 bath Colonial Style home, one block from Muraco School, and minutes from the Middlesex Fells Reservation, offering over 2,575 acres of pristine woodlands, reservoirs, and scenic trails perfect for outdoor recreation. Beautiful updates complement the home’s original oak woodwork, including stained oak Harvey windows with tilt in sashes. The spacious front foyer opens into the living room with a wood burning fireplace. The formal dining room leads out to a serene private rear deck, overlooking a fully fenced yard with native plantings. The sizable kitchen highlights electric cooking, a built in microwave, and peninsula providing additional seating. A side addition added a large front to back family room with abundant natural light, providing even more livable space on the first floor. A private home office with classic French door completes this level. Upstairs, you’ll find a 2021 renovated full bathroom, three sizable bedrooms, and extensive storage space including 25FT attic closet. The walk out basement offers W/D, an above grade, finished room perfect for a home gym or office, and unfinished storage space. A one car garage, off street parking for 3 additional cars and cost efficient solar panels add everyday practicality. Just minutes from vibrant Winchester Center, this home offers access to local shops, cafés, highly rated restaurants, two MBTA commuter rail stations and Winchester’s acclaimed public school system, along with easy access to I-93, Route 128 and Route 3.

4 Stone Ave, Winchester

Listing courtesy of Listing Agent: The Synergy Group from Listing Office: The Synergy Group.

$1,750,000

4 Beds ⋅ 3 Baths ⋅ 73581571 MLS

Welcome to One Overlook Way in Winchester. This spacious 4+ bedroom center-entrance Colonial is tucked away on a short cul-de-sac off High Street, in a premier location close to Ambrose Elementary School and the Winchester Country Club. The foyer opens to a thoughtfully designed floor plan with wonderful flow for everyday living and entertaining. The generously sized eat-in kitchen features stone countertops and stainless steel appliances and connects to the beautiful dining room. The kitchen also opens naturally into the cozy family room - with gas fireplace, custom built-ins and access to the back and side yard, the family room will be well utilized! A larger front-to-back living room with fireplace and box windows is located off the foyer and is complemented by an adjoining oversized library or playroom. Upstairs, the spacious primary suite offers a private bath with double vanity, full shower and great closet space. Three additional bedrooms feature hardwood floors, generous closets and access to a shared full bath. The third-floor bonus space provides flexible room for guests, a home office or storage. The finished lower level adds even more usable space, with a fireplace and room for exercise, hobbies or relaxation. Enjoy the outdoors in this large, level yard with established plantings, brick patio and plenty of space to entertain. There is a two-car garage plus 300+sf of unfinished space above the garage. Please ask the agent for more information. This home truly has it all. This is one home you do not want to miss.

1 Overlook Way, Winchester

Listing courtesy of Listing Agent: Lynne Russo from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.

$1,080,000

3 Beds ⋅ 1 Baths ⋅ 73578621 MLS

Opportunities and possibilities for builders or handyman!! At 6 Reservoir Street, Winchester, a distinguished single-family residence on an expansive 10818 square foot lot. This property represents a unique opportunity for refined living within a desirable community. The residence encompasses three well-proportioned bedrooms plus walk-up to a generously sized attic and one full bathroom. Traditional wrap-around porch in front, and large deck at the rear accessed from the driveway which enters from the street behind. Great location close by to the reservoir and Fells Reservation with easy highway access as well. Sell by owner and AS IS conditions.

6 Reservoir Street, Winchester

Listing courtesy of Listing Agent: Dongjun Lou from Listing Office: HMW Real Estate, LLC.

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