Wellesley Real Estate

Welcome to Wellesley, Massachusetts—a charming town that beautifully blends suburban tranquility with vibrant community spirit. Nestled in Norfolk County, Wellesley is renowned for its picturesque landscapes, top-tier educational institutions, and a rich history that dates back to the early 18th century.

With a population of around 30,000 residents, Wellesley offers a warm, welcoming atmosphere that makes it an ideal place for families, young professionals, and retirees alike. The town is home to several highly regarded schools, including Wellesley High School, which consistently ranks among the best in the state. Families will appreciate the strong emphasis on education and community engagement, ensuring that children thrive in both academics and extracurricular activities.

Nature enthusiasts will find plenty to love in Wellesley, from the scenic trails of the Wellesley College Botanic Gardens to the beautiful shores of Lake Waban. The town boasts an array of parks and recreational facilities, perfect for outdoor activities like hiking, biking, and picnicking.

Wellesley’s downtown area is a delightful mix of boutique shops, cozy cafes, and gourmet restaurants, providing residents with an array of dining and shopping options. The community hosts various events throughout the year, fostering a sense of connection among neighbors and making it easy to meet new friends.

In Wellesley, you’ll find a harmonious balance of suburban charm and modern conveniences, making it not just a place to live, but a place to truly call home. Whether you’re exploring the local parks or enjoying a meal in the heart of town, Wellesley offers an exceptional quality of life that is hard to match.

Newest Listings in Wellesley

$3,495,000

73570737 MLS

Welcome to 28 Clovelly Road, Wellesley-buildable lot with plans and building permit in place, ready for you to bring your dream home to life. Set in the highly sought-after Wellesley Country Club area. Conforming 22,579 sq.ft. buildable lot with no existing structure offers the opportunity to design your own home and build a home that reflects your vision and personal style. Use the available plans and building permit or bring your builder. Bring your vision. Build the home you've always dreamed of.

28 Lot A Clovelly, Wellesley

Listing courtesy of Listing Agent: Liza Adib from Listing Office: Berkshire Hathaway HomeServices Town and Country Real Estate.

$1,995,000

4 Beds ⋅ 4 Baths ⋅ 73570070 MLS

This thoughtfully designed Cape-style home offers first floor living with a master bedroom and full bath, large custom designed kitchen with an eat-in area and adjoining pantry. There is a lovely dining room with built-in cabinets that is connected to a fireplaced living room with a stunning bay window. A first floor den has extensive built-in cabinetry and a half bath. Each season can be enjoyed from the screened in porch overlooking a large and professionally maintained yard with mature plantings and total privacy. The lower level is spacious with a finished family room, full bath, and walkout to the backyard. On the 2nd floor are three bedrooms, an office area, a full bath, and large walk-in closet, plus a walk-in attic for extra storage area. Ideally located across from the Wellesley Country Club, town gardens, Centennial Park, and Longfellow Pond, this property has easy access to commuting routes.

186 Oakland Street, Wellesley

Listing courtesy of Listing Agent: Adler Connolly Squared Team from Listing Office: MGS Group Real Estate LTD - Wellesley.

$3,595,000

6 Beds ⋅ 5 Baths ⋅ 73569459 MLS

Exquisite renovation of this distinctive property blends historic architectural character with sophisticated luxury living. Set on picturesque grounds with beautiful views of gardens, patios, the historic barn, golf course, and skyline vistas. Gracious, light-filled interiors feature hardwood floors, fireplaces, architectural detail, and beautiful views throughout. The sunny kitchen opens to a family room with gas fireplace, wet bar, and french doors to patio while the adjoining breakfast room/sunroom opens to a deck with sunrise views. A spacious great room with beamed ceilings and fireplace provides exceptional entertaining space. A first-floor office with separate entrance and full bath offers potential for an in-law/nanny suite. A wood paneled library with built-ins and a well-appointed dining room round out the first floor. Upstairs are five bedrooms, a sitting room/nursery, and four renovated baths. The third floor features a game room. The expansive lower level includes a recreation room, exercise room, workshop, mudroom, storage, and access to the two-car garage. A historic barn with electricity and water adds character and offers potential for an ADU. Convenient to Wellesley Hills shops, restaurants, commuter rail, and major routes, this exceptional property combines privacy, character, style, and remarkable views.

151 Oakland Street, Wellesley

Listing courtesy of Listing Agent: The Wilson Group from Listing Office: Compass.

$5,450,000

5 Beds ⋅ 8 Baths ⋅ 73569281 MLS

Welcome to 44 Whiting Road, an exceptional residence set within Wellesley’s coveted Country Club neighborhood. Built in 2009 by renowned builder McLaughlin/DeBenedictis, this distinguished five bedroom, six full bath center entrance Colonial offers three thoughtfully designed levels of refined living. An inviting grand foyer sets the tone for the stunning open-concept floor plan, anchored by a custom designed gourmet kitchen appointed with high-end appliances, marble countertops, and a generous center island. The kitchen flows effortlessly into a sunlit breakfast room with expansive picture windows and a gracious family room, where a stone-front gas fireplace provides a warm focal point and frames views of the bluestone terrace and beautifully landscaped grounds. A handsome wood-paneled office, elegant formal living room, formal dining room and well-appointed butler’s pantry further enhance the main level.The second floor features four en-suite bedrooms, including a luxurious primary suite with marble bath and a private sitting room. The third floor offers an additional bedroom, full bath, and cedar closet, providing extra flexibility for guests, a bonus room, or private retreat. The lower level is equally impressive, with a spacious recreation room, exercise room, full bath with steam shower, and abundant storage. Outside, the private grounds and bluestone terrace create an inviting setting for both quiet relaxation and sophisticated entertaining. Ideally situated near the Wellesley Country Club and golf, with convenient access to the town’s renowned shops and restaurants. A truly not-to-be-missed opportunity!

44 Whiting Road, Wellesley

Listing courtesy of Listing Agent: Debi Benoit from Listing Office: William Raveis R.E. & Home Services.

$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

73565253 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.

$1,950,000

3 Beds ⋅ 2 Baths ⋅ 73565252 MLS

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.

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.