Wellesley Real Estate

Welcome to Wellesley, Massachusetts – a charming town that beautifully blends suburban tranquility with a vibrant community spirit. Nestled in Norfolk County, Wellesley is renowned for its picturesque landscapes, top-tier educational institutions, and a strong sense of community. With a population of around 30,000 residents, this idyllic town offers a perfect retreat from the hustle and bustle of nearby Boston, just a short drive away.

Wellesley boasts a rich history, reflected in its stunning architecture and well-preserved historical sites. The town is home to prestigious colleges, including Wellesley College, which is celebrated for its beautiful campus and commitment to empowering women through education. The local school system is consistently ranked among the best in the state, making Wellesley an ideal place for families seeking quality education for their children.

Outdoor enthusiasts will find plenty to love in Wellesley. The town is dotted with lush parks, scenic walking trails, and serene lakes, including the popular Lake Waban and the picturesque Wellesley Town Forest. Whether you’re enjoying a leisurely stroll, biking, or simply soaking in the natural beauty, Wellesley provides an abundance of recreational opportunities.

The vibrant downtown area is a hub of activity, featuring charming boutiques, delightful cafes, and a variety of dining options that cater to all tastes. Community events and farmer’s markets foster a strong sense of belonging, making Wellesley not just a place to live, but a place to thrive.

With its perfect blend of natural beauty, rich history, and a close-knit community, Wellesley is truly a gem in Massachusetts. Come discover why so many choose to call this enchanting town home!

Newest Listings in Wellesley

$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.

$1,449,000

3 Beds ⋅ 3 Baths ⋅ 73562598 MLS

Great Location! Special Wellesley setting bordering conservation land & Fuller Brook! Light-filled 3BR/2.5BA Dutch Colonial offering privacy, character, and exceptional convenience to Wellesley Center, commuter rail, WHS, libraries, shops, parks & Brook Path. Spacious living room with fireplace, dining room opening to deck, and well-appointed kitchen with breakfast bar, pantry storage, Café induction range and stainless appliances. Recent improvements include, Hardie Plank siding, triple-pane ENERGY STAR windows (2023), new dishwasher (2025), refinished hardwood floors (2026), freshly painted deck (2026), and fresh interior paint. MantelMount TV system adds a polished entertainment solution. Upstairs features primary bedroom with double closets, two additional bedrooms and full bath with radiant floor heat. Walk-out lower level offers flexible family/bonus space with second fireplace/Jøtul pellet stove, full bath, laundry and storage. Level wooded lot with native landscaping, raised garden beds and detached one-car garage. A rare combination of peaceful natural setting and outstanding Wellesley access. Schedule a private showing today!

81 Seaver St, Wellesley

Listing courtesy of Listing Agent: Alex Langos from Listing Office: Coldwell Banker Realty - Cambridge.

$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.

$2,895,000

6 Beds ⋅ 5 Baths ⋅ 73559946 MLS

Welcome to a picture-perfect Dutch Colonial in Wellesley's coveted Dana Hall neighborhood! Walk to everything - Wellesley Square restaurants and shops, the commuter rail, the newly constructed and top rated Hunnewell Elementary School, Library, Whole Foods, and the Brook Path. Fully renovated in 2026 - This charming home filled with natural light lives like new construction with elevated finishes throughout. New Hardie shingle siding, roof, Andersen windows, electrical, plumbing, efficient HVAC, and fully insulated. The heart of the home is a stunning, magazine-worthy kitchen featuring a generous center island, eat-in area, walk-in pantry, quartz countertops, and top of the line appliances (Wolf + GE Monogram), with a generous mudroom attached. The formal living and dining rooms are stunning. Upstairs, you'll find four bedrooms and three bathrooms featuring upgraded finishes. The primary suite features a vaulted ceiling, an en-suite bathroom, and his / her closets with custom built-in storage. The primary bathroom boasts a large double vanity and marble walk-in shower. Retreat to the lower level family room / playroom / gym which includes a generous walk-out to the backyard, two large bedrooms, and a full bathroom with walk-in shower. Backyard includes a new bluestone patio, mature decorative trees, lush lawn (with irrigation), and an elegant privet hedge. Driveway and 1.5 car garage on Dexter Rd - A low traffic cul-de-sac with only seven houses.A one of a kind opportunity!

21 Wellesley Ave, Wellesley

Listing courtesy of Listing Agent: Endri Angjeli from Listing Office: Arrive Real Estate.

$1,695,000

73557831 MLS

OPEN BUILDING LOT in exclusive Wellesley Farms! Bring your dreams and ideas and get started on designing and building your custom home in one of the finest neighborhoods in Wellesley. Conforming, flat and fenced 22,388 sq ft lot with no existing structure. Town water, sewer, electricity and gas at street. 20,000 SF zoning, 170' of frontage. Geotechinical Data Report completed. SHOVEL READY!

33 Boulder Rd, Wellesley

Listing courtesy of Listing Agent: Christine Lawrence from Listing Office: Rutledge Properties.

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