Wellesley Homes with Colonial Style

Wellesley Homes with Colonial Style

Welcome to Wellesley, Massachusetts, a picturesque town nestled in Norfolk County that perfectly marries suburban charm with urban convenience. Known for its stunning landscapes, top-rated schools, and vibrant community, Wellesley offers a serene lifestyle just a stone's throw from Boston. With its tree-lined streets, inviting parks, and a rich history, this town is a haven for families, professionals, and retirees alike.

One of the standout features of Wellesley is its architectural beauty, particularly the abundance of Colonial-style homes that grace the neighborhood. These timeless residences reflect the town's rich heritage and are characterized by their elegant symmetry, classic brick facades, and inviting front porches. Many of these homes boast spacious interiors with high ceilings, hardwood floors, and intricate moldings, providing a perfect blend of historical charm and modern amenities.

Living in a Colonial-style home in Wellesley means you’ll enjoy not only the aesthetic appeal but also the sense of community that this town fosters. Take leisurely strolls through the beautiful neighborhoods, visit the local shops and cafes, or partake in community events that bring residents together. Wellesley is also home to top-notch educational institutions, including Wellesley College, making it an ideal place for families looking to invest in their children's future.

Whether you’re searching for your dream home or looking to settle down in a welcoming community, Wellesley’s Colonial-style homes offer a unique opportunity to embrace a lifestyle steeped in tradition and elegance. Come discover the charm of Wellesley, where your dream home awaits!

Newest Wellesley Homes with Colonial Style

$1,395,000
4 Beds ⋅ 3 Baths ⋅ 73566903 MLS
Welcome to this inviting 4 bedroom, 2.5 bath home featuring a desirable open floor plan. The updated kitchen with high end appliances, showcases quartz countertops, a spacious island, and a seamless connection to the living areas, creating an ideal space for both daily living and entertaining. A generous dining room sits just off the kitchen and family room, offering an easy layout for gatherings with friends and family. Upstairs, you’ll find three well-sized bedrooms and two full baths, including a serene primary suite with marble bath. The expansive backyard provides a private outdoor retreat with ample space for recreation, dining, and relaxation. The landscaped setting enhances the outdoor experience while maintaining a sense of privacy. Thoughtfully designed and move-in ready, this home blends comfort, versatility and indoor-outdoor living. Conveniently located near shops, restaurants, commuter rail, and major highways for an easy commute into Boston! Come see all this home has to offer and discover this great opportunity to make it your own.

560 Worcester St, Wellesley

Listing courtesy of Listing Agent: Debi Benoit from Listing Office: William Raveis R.E. & Home Services.
$1,295,000
2 Beds ⋅ 3 Baths ⋅ 73566505 MLS
Custom-built in 2011, this young colonial offers the perfect blend of modern comfort and timeless style on a quiet street in desirable Wellesley neighborhood. The spacious living room with gas fireplace flows seamlessly into the kitchen/dining area with stainless appliances, granite countertops, and direct access to the side yard for effortless indoor-outdoor living. The second floor includes two generous en-suite bedrooms with tiled baths, spacious walkin-in closets, and a convenient laundry. The walk-up third floor has bonus living space. The unfinished lower level features tall ceilings and endless potential for a playroom, gym, or home office. Complete with central air a new tankless water heater, one-car garage with EV charger, and abundant storage, this move-in ready home delivers low-maintenance living in an unbeatable Wellesley location.

5 Oakdale Avenue, Wellesley

Listing courtesy of Listing Agent: Jane Neilson from Listing Office: Douglas Elliman Real Estate - Wellesley.
$1,475,000
3 Beds ⋅ 2 Baths ⋅ 73566375 MLS
Presenting a wonderful opportunity in Wellesley Hills! Charming, well maintained three bedroom colonial sited on .34 acres within walking distance to shops and restaurants. A thoughtful design for a young family or empty nesters looking to downsize. The first level offers a spacious front to back living room with fireplace and custom builtins, formal dining room with custom cabinets, a sun filled kitchen opening to the family room, plus a large sunroom with access to the exterior. The second floor offers the primary with two walk in closets, two additional bedrooms and a small study/office area. The bonus room with skylights on the third level offers great space for an office or play room. Enjoy the private back yard which also includes a fenced in kennel/play area.

7 Grantland Rd, Wellesley

Listing courtesy of Listing Agent: The Bohlin Group from Listing Office: Compass.
$1,980,000
4 Beds ⋅ 4 Baths ⋅ 73565625 MLS
Location! Location! Location! Ideally located in the popular Wellesley Square neighborhood, just steps to the Brook Path, library, commuter train, shops, dining, and highly regarded Wellesley schools. This bright and spacious Colonial offers 4 bedrooms and 4 full baths, with hardwood floors throughout. The impressive two-story foyer opens to an inviting floor plan ideal for comfortable living and entertaining. The extra-large updated kitchen features abundant cabinetry, granite countertops, modern finishes, and a 2025 Bosch stove. A major whole-house renovation and floor plan redesign was completed in 2014, including a spacious family room addition, main bedroom suite, and ductless heating/cooling with 7 units. Two heat-pump systems provide additional efficiency. New roof (2015). Recent updates include attic and crawl-space insulation (2025), driveway extension (2025), fresh interior paint (2026), and driveway recoating (2026). Enjoy a good-sized backyard and an exceptional location close to everything Wellesley has to offer.

8 Wilson St, Wellesley

Listing courtesy of Listing Agent: Nana Lo from Listing Office: S.Y.K. Corporation.
$1,950,000
3 Beds ⋅ 2 Baths ⋅ 73565252 MLS
Bring your vision to life in one of the area’s most desirable neighborhoods. Situated on nearly an acre in the heart of the Bates neighborhood, this property offers exciting possibilities. Transform the current home or start fresh and create something entirely your own. Enjoy a wonderful setting close to Bates Elementary, Boulder Brook conservation land, walking and hiking trails, and nearby tennis courts. An exceptional chance to make your mark in a location that is hard to beat. Demo permit in hand. Buyer and buyer’s agent are responsible for conducting their own due diligence.

53 Elmwood Rd, Wellesley

Listing courtesy of Listing Agent: Donahue Maley and Burns Team from Listing Office: Compass.
$3,050,000
5 Beds ⋅ 5 Baths ⋅ 73563790 MLS
Rarely does a new construction opportunity of this scale arise in Wellesley Hills. Spanning an impressive 6,000 square feet, this 5-bedroom, 5-bathroom residence offers a level of space and volume that is nearly impossible to find at this price point. The sun-drenched interior features exquisite millwork and a thoughtful, modern floor plan. The first floor is designed for effortless living, boasting a formal living and dining room, a dedicated office or guest bedroom with a full bath, and a stunning chef’s kitchen equipped with Thermador appliances that flows into an inviting fireplaced family room that overlooks the very private grounds. Upstairs, you’ll find four generous bedrooms with large finished closets, including a sumptuous primary suite featuring three closets and a spa-like bathroom. The lower level has a play room, mud room, and full bath. Outside, a beautiful, secluded patio offers a private oasis for alfresco dining. If you’ve been searching for a high-design new build that doesn’t compromise on square footage, this is the one. Experience the luxury of extra space in a premier Wellesley location.

23 Wareland Rd, Wellesley

Listing courtesy of Listing Agent: Donahue Maley and Burns Team from Listing Office: Compass.
$1,675,000
4 Beds ⋅ 4 Baths ⋅ 73562667 MLS
Opportunity knocks for home-owners and builders alike! Nestled in the heart of Wellesley’s coveted Historic District on prestigious Cottage Street, this picturesque 1870s New England Colonial offers a blend of timeless historic character with unmatched expansion opportunity in a highly sought-after location. The main home offers 4 beds, 3 baths, and an incredible canvas for a buyer ready to bring their personal touch, or execute a complete vision without paying for someone else’s cosmetic choices.Step outside to discover a secluded backyard retreat built for relaxation and entertaining. A fabulous deck overlooks the private, fenced-in yard, and a dedicated pool house completes the oasis with the 4th bath, providing ultimate convenience for guests and poolside gatherings.What truly sets this residence apart is the substantial planning already secured for the next owner: the property comes with an approved 2025 Historic District Commission (HDC) Certificate of Appropriateness for a stunning custom expansion designed by renowned Royer Architects, allowing you to bypass the lengthy municipal review process and move straight toward building equity.The location delivers ultra-easy lifestyle access to the best of Wellesley: you are just steps from the scenic Brook Path for morning walks and a pleasant stroll from Wellesley’s vibrant town center with boutique shopping, top-tier dining, and the commuter rail station. Situated in the highly sought-after, state-of-the-art HUNNEWELL Elementary School district.Whether you choose to move in, refresh the interiors, or build out the approved expansion, this home represents a rare chance in an unbeatable neighborhood.

29 Cottage Street, Wellesley

Listing courtesy of Listing Agent: Paula Carens from Listing Office: Paula Carens.
$2,095,000
4 Beds ⋅ 3 Baths ⋅ 73562429 MLS
Welcome to this timeless New England Colonial, perfectly situated in one of Wellesley's most sought-after neighborhoods. Filled with natural light, the main level offers an inviting living room, elegant dining room, spacious kitchen with a sunny breakfast nook, and an expansive family room that opens effortlessly into a beautiful four-season sunroom overlooking the private backyard. Upstairs, the impressive primary suite features a vaulted ceiling, walk-in closet, spa-inspired bath, and a peaceful sitting area. Three additional generously sized bedrooms, a full bath, and a convenient second-floor laundry room complete the upper level. The finished lower level provides an oversized recreation room along with excellent storage space. Surrounded by mature landscaping, abutting conservation land and 3.3 miles of trails. Ideally located in close proximity to top rated Fiske elementary school, parks, shopping, dining, and major commuter routes.

42 Sheridan Rd, Wellesley

Listing courtesy of Listing Agent: Aphrodite Karpouzis from Listing Office: Gibson Sotheby's International Realty.
$1,099,999
4 Beds ⋅ 2 Baths ⋅ 73557701 MLS
A timeless Wellesley treasure nestled on the sought-after Wellesley–Natick line. Rich with character and vintage charm, this beloved home offers a rare opportunity to embrace its cozy cottage appeal or reimagine it into the home of your dreams. Original architectural details, warm living spaces, and a welcoming atmosphere create the perfect canvas for homeowners, renovators, or builders alike. Whether you envision preserving its nostalgic charm with thoughtful updates or creating a stunning custom residence, the possibilities are endless. Enjoy a peaceful neighborhood setting with easy access to Wellesley's vibrant downtown, top-rated schools, commuter rail, shopping, dining, and nearby conservation trails. Opportunities like this are increasingly rare—a home filled with history, character, unlimited potential in one of MetroWest's most desirable locations. Bring your imagination and discover everything 7 Schaller Street has to offer.

7 Schaller Street, Wellesley

Listing courtesy of Listing Agent: Sable Homes Metro-West Team from Listing Office: William Raveis R.E. & Home Services.
$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.
$2,849,000
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.
$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.
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