Winchester Homes with Colonial Style

Winchester Homes with Colonial Style

Winchester, located in Middlesex County, Massachusetts, is a charming city that offers a perfect blend of small-town charm and modern conveniences. Known for its beautiful architecture and rich history, Winchester is a sought-after destination for homebuyers looking for a place that combines a peaceful atmosphere with easy access to urban amenities.

One of the unique features of Winchester is its abundance of homes with Colonial style. True to their historical roots, these homes are characterized by their symmetrical design, central entryway, and multiple stories. With their timeless appeal, Colonial-style homes exude elegance and sophistication, making them a popular choice among buyers who appreciate classic architecture.

When you step inside a Colonial-style home in Winchester, you'll often find spacious rooms, high ceilings, and detailed woodwork. Many of these homes also boast beautiful fireplaces, large windows that let in plenty of natural light, and well-manicured gardens that enhance the overall curb appeal.

Living in a Colonial-style home in Winchester allows residents to experience a sense of nostalgia while enjoying modern comforts. The city offers a range of amenities, including excellent schools, parks, shopping centers, and restaurants. Winchester also provides easy access to major highways and public transportation, making it convenient for commuters to travel to nearby cities like Boston.

If you're looking for a home that combines historical charm with modern living, Winchester's Colonial-style homes are sure to captivate your heart. With their timeless beauty and desirable location, these homes offer a unique opportunity to own a piece of New England's rich architectural heritage.

Newest Winchester Homes with Colonial Style

$1,599,000
3 Beds ⋅ 3 Baths ⋅ 73292202 MLS
Discover classic charm & modern luxury in this beautifully renovated colonial. Nestled in desirable neighborhood close to town, soon-to-be new Lynch Elementary, Winter & Horn Pond! Abundant natural light & hardwood floors throughout. Enjoy the spacious LR w/cozy gas fireplace, stunning home office w/custom built-ins & playroom for family time. Inviting formal dining room & eat-in kitchen perfect for entertaining. Second floor features gorgeous primary suite w/walk-in closet & serene en-suite bath w/steam shower, soaking tub, custom built ins & double vanities. Two additional bedrooms & a full hall bath complete this level. LL offers ample finished living space ideal for a family or recreational room, a separate room perfect for a home gym & a thoughtfully designed laundry room. The large, stylish mudroom & half bath can be conveniently accessed from your fully fenced-in yard & expansive patio. Oversized one-car garage w/ample storage on two levels. Move right in & enjoy this home!

64 Woodside Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$2,695,000
4 Beds ⋅ 5 Baths ⋅ 73292156 MLS
European inspired and masterfully crafted, showcases sophisticated design and top-of-the-line systems. A well appointed floor plan awaits with grand scale rooms and elegant detail. Enter through the magnificent foyer, featuring a beautiful curved staircase that leads into the formal living room and separate family room. Bespoke chef's kitchen comes outfitted with professional grade appliances, fireplace and adjoining mudroom. In addition to 3 en-suite secondary bedrooms, the primary suite rivals the finest hotels offering a spa like bath, complete with bidet and w/I closet. Seamless indoor/outdoor flow through 8 sets of French doors to marble columned loggia, lush landscaping, sparkling salt water heated pool and sound system thru-out. An unparalleled entertainment oasis. Other features include wet bar with built in tap, ideal LL 2nd great room and au-pair suite, additional storage room or gym, heated driveway. All a stones throw from town center and the NEW Winchester Center Station.

18 Middlesex St, Winchester

Listing courtesy of Listing Agent: Candice Macoul from Listing Office: Luxury Living Real Estate.
$4,399,000
7 Beds ⋅ 8 Baths ⋅ 73290667 MLS
Step into this stunning, newly constructed home that redefines modern luxury! Designed w/ both elegance & everyday comfort in mind, this residence blends beauty w/ ease of living. The 8’ arched, handcrafted wrought-iron front doors open to a grand 20' foyer, showcasing soaring 10' ceilings, custom rift-sawn beams, and expansive floor-to-ceiling windows. With 25 years of expertise, the master builder’s commitment to exceptional quality & craftsmanship shines through every detail. Spanning four meticulously finished levels, this home leaves nothing to be desired. Highlights include a chef's kitchen w/ dual islands, vaulted ceilings, 3-bay garage (with space for 6 cars), a charming breakfast nook, butler's & dry pantries, a direct entry first-floor office or in-law suite, & an open, finished attic w/ bath. The expansive lower level offers private entry separate living quarters w/full in-law apartment w/ kitchen, 2nd laundry, bedroom, bath, movie theatre, game room & gym w/flex floor plan!

54 Johnson Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$2,890,000
4 Beds ⋅ 4 Baths ⋅ 73290646 MLS
Beautifully renovated 4 bedroom home in sought after Winchester Flats! Featuring a picturesque combination of stylish comfort and modern design. The 1st floor welcomes with an oversized custom mudroom leading to a spacious chef's kitchen featuring upgraded Wolf appliances including gas range, steam oven, and 2 built-in beverage fridges. The family room invites with custom built-in window seats, vaulted ceiling, and a scenic view of the manicured yard. The dining room impresses with show-stopping wallpaper and wainscoting, while the chic living room and home office with built-in desks create a space for all occasions.The 2nd floor features a beautiful primary suite with walk-in closet and ensuite bath with dual vanity, while 3 more spacious bedrooms, 2 full bathrooms, and laundry room provide the ideal set up for family living. The finished lower level boasts additional living space and ample storage, and outside enjoy the ease of a 2 car garage, large yard, and long driveway. Must see!

56 Salisbury St, Winchester

Listing courtesy of Listing Agent: The McLaren Team from Listing Office: Compass.
$3,895,000
5 Beds ⋅ 5 Baths ⋅ 73290640 MLS
Experience the epitome of luxury living in this exceptional, high-end renovation of a breathtaking Winchester gem, located in one of the town’s most coveted neighborhoods. Enjoy stunning lake views from numerous rooms & the expansive 1000SF deck! Thoughtfully redesigned by RENEW, a company committed to blending historical integrity with modern design, paying meticulous attention to every detail. This home boasts a new floor plan w/ fabulous kitchen featuring a LaCornue 5 burner stove, 9' Calacatta marble island & fplc w/ adj family rm. 5 spacious bedrooms & 4.5 baths, including a magnificent primary suite w/ marble turret shower. The finished lower level offers a custom wine cellar, perfect for entertaining w/direct entry access to yard. Every detail in this home has been beautifully crafted w/ hand-selected, top-tier finishes throughout. 3-car garage, & close proximity to Winchester's town center, the commuter train to Boston, Mystic Lakes beach, playgrounds & scenic walking trails.

6 Lakeview Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$2,168,000
4 Beds ⋅ 5 Baths ⋅ 73289485 MLS
Offer accepted,Open House cancel!Stunning custom-built colonial home from 2017! This property boasts an open floor plan with soaring ceilings, abundant natural light, and hardwood floors paired with recessed lighting throughout. The first floor features a spacious layout centered around a show-stopping kitchen, crafted by Bespoke of Winchester, equipped with BlueStar/Sub-Zero stainless steel appliances. A large bedroom with an ensuite bathroom—ideal for an in-law suite or master option—and a half bath/powder room complete the main level. The second floor offers a grand master suite with a luxurious walk-in closet (with an additional washer/dryer hookup) and a spa-inspired ensuite bathroom. Two more bedrooms, each with ensuite baths, and an office space are also located on this level. The extra-deep two-car garage and double driveway provide ample parking. The expansive, private backyard backs directly onto the Fells Reservation, offering a tranquil setting to enjoy nature and entertain

57 Winford Way, Winchester

Listing courtesy of Listing Agent: Sino-US Realty Team from Listing Office: Keller Williams Realty.
$2,350,000
6 Beds ⋅ 4 Baths ⋅ 73289247 MLS
Welcome to your dream home, nestled in a tranquil cul-de-sac! This property combines luxury and functionality, featuring multiple living areas perfect for entertaining. At the heart of the home is a gourmet kitchen with a Wolf cooktop, dual ovens, two Sub Zero refrigerators, and butler's pantry with a wine cooler—ideal for culinary enthusiasts. The family room boasts cathedral ceilings with a slider leading to the deck that accesses the fenced-in yard. The six spacious bedrooms can comfortably support your family’s needs. Enjoy the convenience of both upstairs and downstairs laundry rooms. The custom gym in the lower level offers an excellent space for fitness enthusiasts, while the additional unfinished square footage can be used to suit your needs as a playroom, media room, or game room. This home also features an electric car charger, catering to eco-conscious living. This property offers everything you need for modern living, combining elegance and practicality in one package!

5 Pilgrim Dr, Winchester

Listing courtesy of Listing Agent: Andersen Group Realty from Listing Office: Keller Williams Realty Boston Northwest.
$3,100,000
5 Beds ⋅ 6 Baths ⋅ 73289050 MLS
Your dream home in the perfect location awaits at a phenomenal new price! This brand-new residence has an unparalleled blend of luxury & comfort. Close to the vibrant town center, schools & train. The stunning open floor plan offers a high-end kitchen anchored by a large island with seating, a dining area & a wet bar with a beverage fridge & ice maker. This flows easily to the spectacular family room with high vaulted ceilings, loads of natural light, a fireplace & access to a spacious deck. A dining room, living room, mudroom & powder room complete this floor. Custom mahogany doors, custom molding, trim, & cabinets will delight any discerning buyer. Upstairs, the large primary suite is an oasis with an elegant large bath, a big walk-in closet & soaking tub. 3 other bedrooms complete this floor, including an en-suite guest room. Third floor is has a 5th bedroom & bath, plus a study or playroom. The basement has a massive media room, wet bar, gym & full bath. Big yard, oversized garage.

59 Bacon St, Winchester

Listing courtesy of Listing Agent: The Pallotta Group from Listing Office: Leading Edge Real Estate.
$1,999,000
6 Beds ⋅ 4 Baths ⋅ 73288857 MLS
Step into a world of timeless elegance in this beautifully preserved home, where classic architectural details seamlessly blend with modern comfort. The inviting front porch welcomes you. Inside, high ceilings complement a living room w/beamed ceilings & custom built-ins, a gracious dining room, & a light-filled, eat-in kitchen. The cozy family room offers a charming window seat. A quaint stone patio overlooks a serene, lush backyard, creating your own private oasis! The 2nd floor has 3 spacious bedrms & an updated bath, while the 3rd floor offers 2 more bedrms & a bath. Additional private bedrm w/it's own staircase & bath lends itself to a perfect guest suite. The finished basement adds flexibility for an office, playrm, or gym. With a 2-car garage, exceptional upkeep, & a prime location of just steps to Winchester's vibrant downtown, top-rated schools, & commuter rail, this move-in-ready home is perfect! Outdoor lovers will enjoy the nearby Fells Reservation for hiking & recreation.

7 Herrick St, Winchester

Listing courtesy of Listing Agent: McGlynn & Nigro Team from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.
$2,599,000
5 Beds ⋅ 5 Baths ⋅ 73288818 MLS
Stunning new construction! Energy star rated, high efficiency 5 bed 4.5 bath home perfectly situated in a prime East Side location! The first floor welcomes you w/ an open, airy layout, featuring a stylish mudroom, pantry, bath & home office. The gourmet, high-end kitchen flows seamlessly into the living room, complete w/ a cozy fireplace; the dining area extends out to a deck, overlooking a beautifully landscaped yard & patio. The second floor boasts four spacious bedrooms & three full baths, including a lavish primary suite w/ a spa like bathroom. A well-appointed laundry room is also conveniently located on this floor. The third-floor suite is a true retreat, offering two versatile rooms ideal for extended family, office, or lounge, complete w/ a wet bar, an oversized bath & a 5th bedroom with abundant closet space. The expansive lower level adds even more living space, featuring a large family room and an additional full bath, perfect for entertaining. This home truly has it all

50 Winford Way, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$1,599,000
4 Beds ⋅ 4 Baths ⋅ 73287535 MLS
Attention buyers/builders looking for a unique opportunity to complete the renovation of this stately 1932 brick colonial in the “The Flats.” This 4 bedroom, 3 1/2 bath home has been partially gutted/framed so the unglamorous work has already been done for you! The 1st floor, which is open down to the studs, plumbed & wired, includes a large living room w/ gas-ready fireplace, home office, kitchen overlooking a deck, mudroom, dining room & half bath. This floor includes new Andersen windows. The 2nd floor features 3 bedrooms w/ hardwood floors. The front-to-back primary suite includes a new bath that has been framed, wired & plumbed. A spacious family bath is plumbed, wired & partially demoed. The basement which includes new Andersen windows, is framed, wired & plumbed & includes a bedroom, family room, full bath, laundry, & storage. Updates include a 3-zone HVAC system (2015), new roof (2014), rebuilt chimney, new Andersen windows, Leafguard Gutters, & Azek trim & deck.

41 Foxcroft Rd, Winchester

Listing courtesy of Listing Agent: Paula R. Sughrue from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
$1,899,000
5 Beds ⋅ 3 Baths ⋅ 73287432 MLS
Meticulously maintained 2005 classic hip roof colonial located on a quaint 4 home street close to Winchester center, the Tri-Community bike path, Horn Pond, Packer tennis courts & Wedge pond! Warm and welcoming 10 Room, 5 bed, 2.5 bath home with impeccable finishes throughout. First floor offers a great flow w/ 9 ft ceilings, formal living and dining room with custom architectural details, gourmet eat in chef’s kitchen with custom cherry cabinets, granite counters & Sub Zero & Viking stainless appliances. A large family room w/gas fireplace is perfectly situated off kitchen.The 2nd floor has 4 spacious bedrooms with custom-built closets, including the primary suite w spacious bath, soaking tub & tiled shower. The private 3rd floor flex space showcases high vaulted ceilings, and is plumbed for a 3rd bath. Oversized attached 2 car garage w/ cabinets/built-in storage. Enjoy the sunny 40 ft farmhouse porch off the eat-in kitchen overlooking the charming manicured Beacon Hill-style yard

2 Fairfield Place, Winchester

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