Wellesley Homes with Colonial Style

Wellesley Homes with Colonial Style

Welcome to Wellesley, Massachusetts—a charming town nestled in Norfolk County, known for its picturesque landscapes and vibrant community spirit. Just 20 miles west of Boston, Wellesley offers a perfect blend of suburban tranquility and urban convenience, making it an ideal location for families, professionals, and retirees alike. With its top-rated schools, lush parks, and a thriving downtown area filled with boutique shops and delightful eateries, Wellesley is a place where you can truly feel at home.

One of the standout features of Wellesley is its stunning collection of Colonial-style homes. These timeless residences, characterized by their symmetrical facades, gabled roofs, and classic brick exteriors, exude an air of elegance and tradition. Many of these homes are set on beautifully landscaped lots, providing ample space for families to enjoy outdoor activities and create lasting memories. Inside, you’ll find spacious layouts, hardwood floors, and charming period details that reflect the rich history of the area.

Living in a Colonial home in Wellesley means embracing a lifestyle steeped in both comfort and sophistication. Whether you’re hosting a gathering in your grand living room or enjoying a quiet evening on your front porch, these homes offer a warm and inviting atmosphere. Plus, with easy access to Boston’s cultural attractions, shopping, and dining, Wellesley provides the perfect backdrop for a vibrant life.

Explore the beauty and charm of Wellesley, where Colonial-style homes await to welcome you to a community that feels like family. Discover your dream home today!

Newest Wellesley Homes with Colonial Style

$4,999,000
6 Beds ⋅ 8 Baths ⋅ 73555707 MLS
Nature Lovers Paradise on the Charles River! Stunning in every season, each element of this spectacular property is crafted to maximize your enjoyment and access to the great outdoors. Reimagined by renowned architect Patrick Ahern, the exterior boasts a flat grassy backyard and stone patios with unobstructed views. Inside, a gracious and flexible floor plan is filled with light and views from myriad windows, French doors, and private balconies. First floor living with exquisite primary bedroom suite, a great room, expansive living room, dining and updated kitchen w/ light-filled breakfast room, an add’l bedroom suite and choice of offices complete the main floor. Upstairs, 4 more ensuite bedrooms, including a 2nd primary suite option. Large walk-out finished LL w/ bar, gym & media room. 3 car garage and flat courtyard driveway off protected cul de sac within minutes of extensive Wellesley Trails and Town Center. A notch above the rest. Bring your hiking shoes, kayaks, lounge chairs and lawn games!

12 Winding River Cir, Wellesley

Listing courtesy of Listing Agent: Christine Lawrence from Listing Office: Rutledge Properties.
$2,865,000
5 Beds ⋅ 6 Baths ⋅ 73552915 MLS
Exceptional opportunity to own 5,100+ sq. ft. of luxury 2024 construction offering outstanding value in one of Wellesley's most convenient in-town locations. Just steps to Hardy Elementary, Morse's Pond, Fells Library, Wellesley Center & commuter rail. Thoughtfully designed for modern living, this sun-filled home features soaring ceilings, exceptional craftsmanship & four finished levels. Stunning chef's kitchen w/ oversized island & premium appliances flows seamlessly into dramatic family room—ideal for everyday living & entertaining. Elegant dining room, thoughtfully designed mudroom & private bedroom suites on the 2nd, 3rd & lower levels provide exceptional flexibility for guests, au pair, home office or multigenerational living. Gorgeous primary bedroom suite w/ lavish bath. Expansive lower level offers endless possibilities for recreation, fitness or media. A rare opportunity to enjoy the quality, space & convenience of nearly new construction.

265 Weston Rd, Wellesley

Listing courtesy of Listing Agent: Petrone-Hunter Realty Group from Listing Office: Coldwell Banker Realty - Wellesley.
$2,395,000
4 Beds ⋅ 5 Baths ⋅ 73552192 MLS
Nestled on a quiet cul-de-sac near Morses Pond and Wellesley's renowned trail network, this modern Colonial offers 3,750 sq ft across three finished levels. A gracious foyer opens to formal living and dining rooms, while the sun-filled family room with fireplace flows seamlessly into the renovated chef's kitchen featuring Viking and Miele appliances, quartz countertops, center island, breakfast nook, and access to the deck overlooking the private fenced backyard. Upstairs, the spacious primary suite offers a luxurious bath and oversized walk-in closet, accompanied by three additional bedrooms, including one en suite, a full bath, and second-floor laundry. The finished lower level features an expansive recreation room, media room, bar area, exercise space, powder room, and abundant storage. Convenient to Wellesley Center, top-rated schools, shopping, commuter routes, and outdoor recreation.

11 Shadow Ln, Wellesley

Listing courtesy of Listing Agent: Marjorie Gold from Listing Office: Hammond Residential Real Estate.
$3,250,000
4 Beds ⋅ 4 Baths ⋅ 73551561 MLS
Nestled in the heart of prestigious Wellesley Farms, this stately 1930 center entrance Colonial offers timeless curb appeal and an exceptional opportunity to reimagine a classic. Boasting approximately 3,712 square feet of living space, this gracious home features five spacious bedrooms, three full baths, and a convenient half bath. With a solid brick exterior, enduring slate roof, and rock-solid bones, this property exudes old-world craftsmanship rarely found today. While the interior awaits your personal vision and updates, the home's elegant proportions, rich architectural details, and prime location provide an incredible canvas to create your dream residence in one of Wellesley's most sought-after neighborhoods.Sold ASIS. Priced to sell.

25 Hundreds Cir, Wellesley

Listing courtesy of Listing Agent: Greer Tan Swiston from Listing Office: Coldwell Banker Realty - Newton.
$1,198,000
3 Beds ⋅ 2 Baths ⋅ 73547038 MLS
Location, Location, Location! Lovingly maintained Victorian home on a beautifully landscaped, fenced, level yard. First floor offers bright and inviting living room, dining room with French doors that lead to a large private brick patio, expanded and updated eat-in kitchen, and a large updated half bathroom. Three bedrooms and an updated full bath are located on the second floor. Additionally, there is a flexible bonus room located on the third floor that can be used as an office/playroom or fourth bedroom. This home is ideally situated just minutes from Linden Square, local shops, restaurants, schools, commuter rail, and Wellesley town center, with easy access to major routes and highways.

296 Linden St., Wellesley

Listing courtesy of Listing Agent: Mariam Priestley from Listing Office: Berkshire Hathaway HomeServices Town and Country Real Estate.
$2,295,000
4 Beds ⋅ 4 Baths ⋅ 73546333 MLS
Beautifully maintained 4 bedroom, 3.5 bath Colonial offering 3,776 square feet of versatile living space in a highly desirable Wellesley location. Built in 1993, this home combines timeless design with the flexibility today's buyers seek. The thoughtfully designed floor plan features spacious living and entertaining areas, a dedicated home office ideal for remote work with generous natural light throughout. The finished walk out lower level provides exceptional bonus space perfect for a recreation room, media room or guest retreat - offering direct access to the outdoors. Upstairs, comfortable bedrooms and well-appointed baths create a welcoming setting for family and guests alike. Ideally situated near commuter rail access, major routes, and all that Linden Square has to offer, including shops, restaurants, and everyday conveniences. This home delivers the perfect balance of comfort and convenience in one of Wellesley's most sought after neighborhoods.

38 Upwey Rd, Wellesley

Listing courtesy of Listing Agent: Erica Lockberg from Listing Office: Berkshire Hathaway HomeServices Town and Country Real Estate.
$1,625,000
3 Beds ⋅ 3 Baths ⋅ 73546159 MLS
Come see the perfect blend of sophisticated design and everyday comfort in this stunning 3-bedroom, 2.5-bathroom brick home situated on a picturesque, tree-lined street. The inviting open floor plan is bathed in natural light, accentuating the gleaming hardwood floor running throughout the entire home. A chef’s kitchen on the first floor featuring high-end appliances, custom cabinets, and ample prep space. An elegant French door leads directly from the dining area to a spacious deck for relaxing & entertaining. A sun-drenched space perfect for a quiet home office/sunroom. Primary bedroom on 2nd floor is your private sanctuary featuring a beautiful ensuite bath with heated floor. Two additional well-sized bedrooms offer flexibility for family, guests or hobby rooms. The versatile lower-level finished space provides ultimate setting for a game/exercise room. Enjoy the convenience of "walk-to" living, whether you are commuting via nearby train station or exploring the vibrant town center.

20 Shaw Rd, Wellesley

Listing courtesy of Listing Agent: Anita Sung from Listing Office: Shea Realty Group.
$1,275,000
3 Beds ⋅ 3 Baths ⋅ 73545904 MLS
Classic charm meets modern luxury in this beautifully updated 3-bedroom, 3-bathroom 1920's Colonial. The main level welcomes you with high ceilings, an open concept layout and an abundance of natural light throughout. Flexible space for living and dining as well as generous family room. Gorgeous modern eat in kitchen with stainless steel appliances and gas cooking. Step outside to your private oasis featuring a gorgeous back deck and a meticulously landscaped terraced yard, perfect for outdoor entertaining and sunset views. Situated in a prime, highly sought-after Wellesley neighborhood, this home offers an unbeatable commuting location with easy access to all major routes and is just moments away from Schofield Elementary School.

22 Cedar St, Wellesley

Listing courtesy of Listing Agent: The Shulkin Wilk Group from Listing Office: Compass.
$5,995,000
6 Beds ⋅ 6 Baths ⋅ 73545332 MLS
One of Wellelsey's signature properties! Rarely available 18 room estate w/ 4 floors of living situated in the heart of Peirce Estates. Stunning foyer w/ curved staircase. Sunken living room w/ coffered ceilings & stone fireplace. Oversized dining room w/ bay window plus large butler's pantry. Kitchen w/ stainless appliances, center island & breakfast nook. One of a kind family room filled w/ built-in bookcases, coffered ceiling, fireplace & wet bar perfect for entertaining & everyday living. Wood panel den/office. Main bedroom w/ 2 walk-in closets & fireplace. 3 additional beds & 2 baths. Large sitting room/bonus room w/ fireplace completes 2nd floor. Third floor w/ 2 more beds & bath plus another large bonus room with built-in bunk beds. Lower level w/ playroom, game room & bar room. Over 7700 sq ft with almost one acre of privacy abutting the reservoir. Fieldstone patio. 400 amp service. 3 car garage & steel beam construction. Your chance to own one of Wellesley's most iconic homes!

43 Monadnock Road, Wellesley

Listing courtesy of Listing Agent: Melissa Dailey from Listing Office: Coldwell Banker Realty - Wellesley.
$1,399,000
3 Beds ⋅ 2 Baths ⋅ 73545066 MLS
**** Attention Builders, Developers and End Users**** The project that you have been waiting for! Brimming with charm and potential, this classic colonial is nestled into a highly sought after Wellesley neighborhood. Charm abounds at this 3 Bedroom, 2 Bath home. Incredible upside/ investment potential. Renovate or build new. The home features a formal living room with fireplace, dining room, three season porch and kitchen. Hardwood floors and period details. One car garage and lovely private yard with mature plantings. Very close proximity to The Bates School, Kelly Memorial Park and fields, Boulder Brook Reservation, Fells Market and all that Wellesley has to offer.

10 Wilde Rd, Wellesley

Listing courtesy of Listing Agent: Moira Lown from Listing Office: Coldwell Banker Realty - Wellesley.
$3,295,000
5 Beds ⋅ 5 Baths ⋅ 73542063 MLS
This exceptional new construction home is the perfect blend of transitional elegance and modern design. It is crafted with impeccable attention to detail. Warm, rich white oak accents, custom millwork, and designer finishes create an inviting atmosphere throughout. A show stopping chef’s kitchen features sleek custom cabinetry, quartz countertops, a massive center island. The kitchen flows seamlessly into the fireplaced family room, where soaring windows fill the space with natural light. An elegant dining room is topped with a contemporary tray ceiling, adding architectural interest and sophistication. Each bathroom offers unique finishes including a striking quartzite sink in the powder room. The luxurious primary is complete with a spa-inspired bath featuring a soaking tub, steam shower, and rain head. An outstanding lower level with a gym area, playroom, and wet bar. Ideally situated in a highly convenient location with every amenity just moments away.

18 Rockland Street, Wellesley

Listing courtesy of Listing Agent: Adler Connolly Squared Team from Listing Office: MGS Group Real Estate LTD - Wellesley.
$3,299,000
6 Beds ⋅ 5 Baths ⋅ 73542007 MLS
Set on a tree-lined block in the coveted Cliff Estates enclave, this to-the-studs 2025-26 renovation + expansion of a classic NE Colonial is a singular achievement of brilliant design, timeless elegance, and refreshing livability. The expansive living spaces are distinguished by beautifully curated fixtures and finishes, from the fluted marble fireplace to bespoke lighting and hardware. Anchored by a breathtaking central island and 42” Wolf range, the kitchen opens to a spacious family room, dining, and separate great room which all embrace views of the lushly landscaped nearly ½-acre lot. Versatile 1st fl ensuite guest room / office. Four gracious 2nd fl inc. four gracious bedrooms and three elegant new baths inc. a luxe primary suite + laundry. Amazing skylit 3rd fl with new 2026 dormer inc. a 6th bedroom or office + auxiliary living area. Walkout lower level w direct-entry garage, mudroom, ½ bath, open-plan LR or gym + sliders to covered patio and grassy yard. Premier location.

209 Bristol Rd, Wellesley

Listing courtesy of Listing Agent: Elisabeth Preis from Listing Office: Compass.
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