Weston Homes with Colonial Style

Welcome to Weston, Massachusetts, a picturesque town nestled in Middlesex County, known for its serene landscapes and rich history. With its charming streets lined with lush trees and beautifully maintained homes, Weston embodies the quintessential New England experience. The town boasts an impressive array of amenities, including top-rated schools, vibrant community events, and a strong sense of community spirit that attracts families and professionals alike.

One of the standout features of Weston is its stunning collection of Colonial-style homes. These timeless residences, characterized by their symmetrical facades, gabled roofs, and classic brick or clapboard exteriors, exude a sense of elegance and tradition. Many of these homes are set on expansive lots, offering ample space for outdoor activities and gatherings. Inside, you’ll find spacious layouts with high ceilings, intricate moldings, and inviting fireplaces that create a warm and welcoming atmosphere.

Weston’s Colonial homes are not just aesthetically pleasing; they also reflect the town’s rich heritage and commitment to preserving its historical roots. Living in one of these homes means becoming part of a community that values both its past and its future. Whether you’re sipping coffee on a charming front porch or hosting a family gathering in a grand living room, these homes provide a perfect backdrop for creating lasting memories.

With its blend of history, beauty, and community, Weston is more than just a place to live; it's a lifestyle. Explore the enchanting Colonial homes that await you in this idyllic town and discover the perfect setting for your next chapter.

Newest Weston Homes with Colonial Style

$4,800,000

5 Beds ⋅ 7 Baths ⋅ 73593840 MLS

Set on 5.6 private acres on Weston’s highly desirable south side, this impressive estate offers exceptional privacy and timeless appeal. Tucked at the end of a long, winding driveway, this Federal Colonial blends classic architecture with comfortable living, featuring sun-filled interiors, a dramatic two-story family room with fireplace, a bright sunroom, and a stylish home office. The flexible layout includes a first-floor bedroom suite ideal for guests, while upstairs offers five bedrooms, including a spacious primary suite with fireplace, luxurious bath, dressing area, and multiple walk-in closets, along with four additional bedrooms and three full baths. The finished walk-out lower level with a separate entrance includes a kitchen, bedroom, full bath, exercise and media rooms—perfect for extended living or entertaining. Complete with a five-car garage and located just minutes from the state’s top public schools, with convenient access to Boston.

451 Wellesley St, Weston

Listing courtesy of Listing Agent: Yang Liu from Listing Office: Weston Realty LLC.

$3,295,000

6 Beds ⋅ 6 Baths ⋅ 73589867 MLS

Set on 1.58 professionally landscaped acres in one of Weston’s most desirable neighborhoods, this brick Colonial has been extensively renovated and offers a spacious, highly functional floor plan. The updated kitchen features new appliances, a walk-in pantry, and breakfast area with wet bar, opening to a family room with fireplace. The main level is complete with a formal dining room, front-to-back living room with a second fireplace, and private first-floor office with custom built-in bookcases. Upstairs, all five bedrooms are conveniently located on one floor, including the primary suite with a newly renovated spa-like bath, large walk-in closet, and expansive sunroom ideal as a sitting area or private retreat. The finished lower level offers exceptional flexibility with a large recreation room, additional bedroom or bonus room, two full baths, kitchenette, exercise room, and exterior access to the backyard—ideal for extended family or guests. Surrounded by mature landscaping with private wooded views and paths, the property also includes a two-car garage, spacious mudroom, and two laundry areas. Move-in ready and filled with natural light, this exceptional Weston home offers generous living space in a beautiful setting with convenient access to schools, town center, and Boston.

172 Country Drive, Weston

Listing courtesy of Listing Agent: The Sarkis Team from Listing Office: Douglas Elliman Real Estate - The Sarkis Team.

$3,495,000

6 Beds ⋅ 6 Baths ⋅ 73587759 MLS

Privately set on 2.7 acre, this distinguished 16-room landmark residence embodies the timeless elegance and gracious scale of a classic New England estate, thoughtfully enhanced for modern living. A stately entry welcomes you to beautifully preserved architectural details, including dramatic ceilings and windows, exquisite millwork and hardwood floors throughout. Designed equally for grand entertaining and intimate gatherings, the formal living room is anchored by a handsome fireplace, while the richly appointed library, with its own fireplace and built-in bookcases, offers a warm and inviting retreat. A comfortable family room provides a relaxed setting for everyday living. At the heart of the home, the exceptional chef’s kitchen features a generous dining area and beautifully appointed butler’s pantry with direct service to the expansive formal dining room, where a fireplace creates an elegant backdrop for memorable occasions. A first-floor guest bedroom or dedicated home office provides exceptional flexibility. The second floor offers a private bedroom level with a spacious primary with full bath, three additional bedrooms and two more full baths. A separate staircase leads to a private accessory apartment with its own kitchen, sitting room, two bedrooms and full bath—ideal for extended family, guests or staff. Expansive covered porches overlook the heated pool and broad open lawns, creating a beautiful setting for summer entertaining and relaxed outdoor living. Rarely does a property combine such gracious proportions, historic character, versatility and convenience. The 2.7 acres include an approximately 1-acre buildable lot currently going through the town of Weston Flexible Development zoning and subdivision process. Ask listing agent for details.

863 Boston Post Road, Weston

Listing courtesy of Listing Agent: Denise Mosher from Listing Office: Coldwell Banker Realty - Weston.

$5,850,000

5 Beds ⋅ 6 Baths ⋅ 73583804 MLS

Set on 4.66 acres of beautiful, wooded land, 1 Cabin Rd presents a rare opportunity to create something truly special in Weston. Tucked into a private, natural setting, the property offers an exceptional sense of peace, seclusion, and connection to the surrounding landscape. Whether envisioned as the setting for a thoughtfully designed new home, a renovation or expansion, or another long-term vision, the property provides a unique canvas for a buyer looking to create something truly tailored to their needs. With its generous acreage, wooded setting, and privacy, 1 Cabin Rd is an opportunity to imagine what could be created here.

1 Cabin Rd, Weston

Listing courtesy of Listing Agent: Maggie Gold Seelig from Listing Office: MGS Group Real Estate LTD.

$4,995,000

6 Beds ⋅ 8 Baths ⋅ 73579890 MLS

A rare and exceptional six bedroom estate with timeless architectural appeal, Designed by Jan Gleysteen Architects, this custom home showcases unsurpassed craftsmanship, meticulous attention to detail and curated finishes throughout. The first floor welcomes you with the grand foyer's dramatic staircase, a richly appointed mahogany-paneled library, and elegant formal living and dining rooms. The kitchen includes a large island, breakfast room that leads to the family room anchored by a beautiful limestone fireplace and screened in porch. Five en suite bedrooms are highlighted by the expansive primary suite complete with a spa-like bath and generous walk-in closets. The third floor has a sun-filled sitting room with a 6th bedroom. The lower level offers a bonus room with bar, golf simulator room and home gym. Set on one of Weston's most picturesque roads close to trails and major commuting routes to Boston and Cambridge.

448 Concord Road, Weston

Listing courtesy of Listing Agent: Mizner + Montero from Listing Office: Gibson Sotheby's International Realty.

$9,450,000

7 Beds ⋅ 11 Baths ⋅ 73577074 MLS

Magnificent residence sited on 2.78 private and pristine acres in one of Weston’s most coveted locations. Completely renovated with the highest level of finishes offering every modern amenity. This exceptional home offers estate-like living designed equally for comfortable family life and sophisticated entertaining. The modern designer kitchen anchors the center of the home and flows seamlessly into the sumptuous fireplaced family room with access to private deck overlooking the pool and grounds and spacious screened porch, creating an inviting open floor plan. The formal dining room enhanced by a butler’s pantry is complemented by a well-proportioned formal living. Multiple home offices, a generous mudroom, dog-washing room and a large gym are just a few of the exceptional features this home offers. This home offers two luxurious primary suite options, one on each of first and seconds levels providing exceptional flexibility. All bedrooms are generously sized and feature ensuite baths. The lower level provides dedicated play, craft and billiard spaces along with ample storage. A sleek and private two-bedroom accessory dwelling with separate entrance and two-car garage offers additional accommodations. Resort-like grounds are enhanced with a beautiful pool, well equipped cabana, expansive patios, and private tennis court, creating an extraordinary setting for year-round living and entertaining. The incomparable residence provides the ultimate in private living while offering easy access to Boston and Weston’s renowned schools.

73 Chestnut Street, Weston

Listing courtesy of Listing Agent: Deena Powell from Listing Office: Gibson Sotheby's International Realty.

$4,585,000

6 Beds ⋅ 7 Baths ⋅ 73575514 MLS

Introducing an elegant shingle and stone residence prominently situated in the prestigious Weston Estates neighborhood. This custom home is masterfully constructed with fine attention to detail by an acclaimed builder. A striking stone fireplace graces the family room and complements the open concept design. The classic floor plan features a grand two story foyer, charming sun room and fabulous finished lower level. The 6th bedroom suite located on the 3rd floor can be used as an in-home office or as a special getaway for guests. The exceptional grounds are architecturally enhanced with a decorative gazebo with a built-in kitchen. The exquisite backyard has a sprawling stone patio adorned with beautiful perennial gardens and manicured grounds. This unique home has all the desired amenities and gravitas for the most discerning buyer.

21 Westerly, Weston

Listing courtesy of Listing Agent: Mizner + Montero from Listing Office: Gibson Sotheby's International Realty.

$2,495,000

4 Beds ⋅ 5 Baths ⋅ 73574322 MLS

Nestled on one of Weston's most picturesque roads, this young Colonial completed in 2008 offers something truly rare in Weston: a coveted in-town location. The Town Green, Weston Center, the library, the elementary schools, and Land's Sake Farm, with its seasonal harvests and pick-your-own fields, are all just moments from your front door. In a town known for sprawling estates and winding country roads, a home that pairs this level of craftsmanship with such close proximity to the heart of town is a special find. Inside, every detail has been thoughtfully considered, from the sun-drenched interiors to the refined finishes that flow effortlessly from room to room, striking a beautiful balance between elegant and inviting. Spacious gathering areas make entertaining a pleasure, while private retreats throughout the home offer quiet comfort at the end of the day. Meticulously maintained and truly move-in ready, this home reflects pride of ownership in every corner. Beyond the center, enjoy scenic conservation trails, nearby shopping and dining, and easy access to major commuting routes. Rarely does a home offer this blend of quality, character, and town center convenience in one of MetroWest's most desirable communities.

703 Boston Post Rd, Weston

Listing courtesy of Listing Agent: The Shulkin Wilk Group from Listing Office: Compass.

$3,595,000

4 Beds ⋅ 6 Baths ⋅ 73574034 MLS

Architecturally designed, this 2024 modern farmhouse is beautifully sited on a level lot in the coveted south side of Weston. This thoughtfully 4 bed/5.5 bath Single Family is crafted with custom finishes across three levels, the sun-drenched open floor plan features 9' ceilings, crown moldings, and seamless flow. The chef’s kitchen offers custom cabinetry, Quartz “Blue Savoi” countertops, and a breakfast area with patio access, opening to a spacious family room with a stone fireplace. Once you enter the garage you are greeted with a large mudroom, half bath and laundry room. Also featured is a walk in pantry. Upstairs features four ensuite bedrooms, including a luxurious primary suite with fireplace, Carrera marble bath, and double walk-in closets. The finished lower level includes a gym/media room, custom wet bar, and full bath. Expansive backyard with room for a pool or sport court. Close to top schools, major routes, and Wellesley.

55 Oakdale Ave, Weston

Listing courtesy of Listing Agent: Christman Johnsson Group from Listing Office: Hammond Residential Real Estate.

$6,680,000

5 Beds ⋅ 9 Baths ⋅ 73573009 MLS

Privately sited on a cul-de-sac in Weston’s coveted South Side, this custom-built residence offers beautifully appointed living space across three finished levels, set on 1.38 acres. Designed by award-winning architect Bart O’Brien and built by Whitman Homes, the home brings together architectural distinction, exceptional craftsmanship, and professionally reimagined grounds to create a setting of impressive scale, privacy, and livability. A dramatic two-story foyer introduces formal living and dining rooms with custom millwork, hardwood floors, and multiple fireplaces. At the heart of the home, a light-filled family room with soaring ceilings and a commanding wall of windows opens seamlessly to a chef's kitchen with professional-grade appliances, center island, and two butler's pantries. A richly appointed library/home office and covered porch and bluestone patio complete a main level built for entertaining and everyday living. Five en-suite bedrooms include a luxurious primary suite with fireplace, custom walk-in closets, and beautifully appointed baths. The expansive walkout lower level extends directly to the backyard and features a great room with wet bar, media room, exercise room, and wine cellar. An attached three-car garage completes the residence. The grounds have undergone a significant professionally engineered, town-approved transformation — replacing formerly rocky terrain with an expansive, level, grassed backyard framed by mature trees and refreshed landscaping. The result is a rare combination of usable, private outdoor space for recreation, entertaining, and daily life, seldom found on estate lots of this scale. Ideally set on Weston's South Side bordering Wellesley — moments from Weston and Wellesley town centers, conservation trails, and the Weston public school district, with convenient commuter access to Boston. A distinguished offering in Weston, MA 02493 — where architecture, craftsmanship, and beautifully reimagined grounds come together.

25 Holly Cir, Weston

Listing courtesy of Listing Agent: Team Coyle from Listing Office: Compass.

$6,695,000

6 Beds ⋅ 8 Baths ⋅ 73572991 MLS

Enter through a long tree lined driveway and arrive at this extraordinary Shingle Style Estate on a sprawling 2.58 acre lot in one of Weston's most desirable Southside neighborhoods.This turn key Modern Classic residence offers over 9000sf of sun-filled interior space, 6 en suite bedrooms, a 4 car garage, an oversized chef's kitchen open to a fireplaced family room with french doors leading to stone terraces and a lushly landscaped backyard perfect for entertaining. Bordering conservation land and offering total privacy, this beautiful Nantucket style home built in 2016 offers magnificent level acreage and has potential for a pool and sports court. A lavish lower level features high ceilings, with an entertainment lounge, a glass walled wine cellar, a spectacular gym, full bath and flex space for a media room. The luxurious primary suite has vaulted ceilings, a fireplace, a balcony overlooking the breathtaking grounds and a spa like bathroom with steam shower. This home offers a rare combination of land, location and flawless move in condition. Enjoy fast access to Weston's top ranked public and private schools, all commuter routes and an amazing lifestyle in one of Greater Boston's premier communities.

250 Country Drive, Weston

Listing courtesy of Listing Agent: Rosemary McCready from Listing Office: Compass.

$2,850,000

3 Beds ⋅ 5 Baths ⋅ 73569214 MLS

Completely renovated and expanded in 2023 this custom home offers an exceptional amount of flexible living space -- far beyond a traditional three-bedroom layout -- with multiple rooms across several levels offering endless possibilities for working, entertaining, exercising, relaxing, and pursuing hobbies at home. Abutting a picturesque seasonal brook, the home features large windows that fill the interior with natural light and capture beautiful views. Quality finishes, generous living areas, and a beautiful natural setting make this a truly special Weston home.

28 Bogle, Weston

Listing courtesy of Listing Agent: Valentina Ossikine from Listing Office: Blue Seagull Realty.

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.

Weston Homes with Colonial Style

Newest Weston Homes with Colonial Style

How much is your home worth?

How much is your home worth?