Wellesley MA Historical Real Estate, Homes for Sale

3 Beds ⋅ 2 Baths ⋅ NEW Status ⋅ 73575899 MLS ⋅ 2,384 SqFt.

Privately set on 1.42 acres at the end of a secluded cul-de-sac, this gracious Colonial offers a rare blend of privacy, natural beauty, and timeless charm. Surrounded by mature trees and picturesque grounds, the home features sun-filled living spaces, an inviting family room with cathedral ceiling, spacious living room, and two fireplaces that bring warmth and character throughout. The generous primary suite provides a peaceful retreat, while central air conditioning and a two-car garage with EV charger add everyday convenience.Outdoor living is equally inviting with a stone patio and expansive deck designed for entertaining or simply unwinding in the tranquil setting. Rarely does a property offer such a serene and private atmosphere while remaining so well connected to everything Wellesley has to offer.

41-A Hunnewell Street, Wellesley

$1,195,000

3 Beds ⋅ 2 Baths ⋅ NEW Status ⋅ 73575416 MLS ⋅ 1,474 SqFt.

Welcome to College Heights. This classic home offers an unbeatable in-town lifestyle, just blocks from Wellesley's shops, restaurants, and commuter rail—your chance to enjoy effortless access to everything, all from a charming, established neighborhood. You are greeted by a covered portico, and inside tall ceilings, hardwood floors, and an easy, open flow set the tone throughout. The updated kitchen impresses with a substantial island, quartz countertops, and generous cooking space, while the sun-filled breakfast area just beyond makes for a bright, welcoming spot to gather. A living room next to the kitchen offers a relaxed retreat for everyday living. Upstairs, you'll find three bedrooms plus a versatile office nook—ideal for remote work or study. A renovated mudroom leads outside to a private yard framed by mature plantings, creating a peaceful outdoor escape. An excellent opportunity to start your next chapter.

56 Curve Street, Wellesley

$1,885,000

4 Beds ⋅ 4 Baths ⋅ NEW Status ⋅ 73575263 MLS ⋅ 3,093 SqFt.

An inviting front porch welcomes you to this traditional New England Colonial, steeped in local history and timeless charm. Step inside the lovely foyer and gracious center hall, where a thoughtful floor plan offers effortless living and entertaining. An abundance of windows fills the home with natural light. The custom-designed kitchen is a chef’s delight, featuring two sinks, two ovens, and generous counter and cabinet space. It opens to the formal dining room with its walk-in bay and the cozy family room, complete with built-ins. Pocket doors lead to the elegant living room, where a gas fireplace and window seat create the perfect setting for relaxing or enjoying a quiet read. Upstairs, the primary bedroom features two closets, a charming bay window, and an en suite bath with a large shower, double vanity and laundry. Two additional generously sized bedrooms and a full bath complete the second floor. The tree-top third-floor retreat, surrounded by a bank of windows, offers a peaceful and inspiring space for an office or studio, along with a fourth bedroom, full bath, and abundant storage. Designed by a Beacon Hill landscape architect, the beautifully landscaped grounds invite you to enjoy the brick patio and thoughtfully designed gardens. Two driveways provide parking for four cars.Ideally located near the Brook Path, Wellesley Hills commuter rail to Boston, restaurants, and cafés, with easy access to major commuting routes, this exceptional home offers the perfect blend of character, comfort, and convenience—an unbeatable offering for your next home.

35 Forest Street, Wellesley

$4,980,000

5 Beds ⋅ 5 Baths ⋅ NEW Status ⋅ 73574731 MLS ⋅ 5,296 SqFt.

From the moment you arrive, you’ll fall in love with this much-admired white brick Colonial, beautifully sited on a charming corner in Wellesley’s coveted Cliff Estates. Set back from the road and surrounded by beautifully landscaped grounds, this exceptional home offers the perfect blend of elegance, comfort, and space for today’s lifestyle. Inside, gracious rooms unfold with everything exactly where you want it—and more than you expect. The inviting fireplaced living room opens to a light-filled sunroom, ideal as a home office or quiet retreat, with French doors leading to the stone patio. The state-of-the-art kitchen features generous stone countertops, new ovens and Sub-Zero refrigeration, a charming dining area with banquette seating, and an exceptional walk-in pantry. A gracious dining room with a window seat and custom built-ins is perfect for entertaining.The oversized family room, with its dramatic barrel ceiling, abundant windows, and doors opening to the yard, is sure to become the heart of the home. An additional study provides yet another flexible space for working from home or relaxing. A glamorous turned staircase leads to the second floor and a stunning primary suite featuring two walk-in closets and a luxurious marble spa bath. Three additional bedrooms and two full baths, including one en-suite, complete this level. The finished lower level offers even more versatile living space with a playroom, exercise area, additional bedroom, and full bath. Oversized three-car garage with added storage space is such a plus! Outside, enjoy professionally landscaped grounds with mature trees and beautiful plantings. Exceptionally maintained and beautifully decorated throughout, this elegant Cliff Estates home offers a rare combination of timeless style, generous living space, and effortless everyday comfort.

97 Arnold Road, Wellesley

$1,799,000

4 Beds ⋅ 4 Baths ⋅ NEW Status ⋅ 73574530 MLS ⋅ 2,714 SqFt.

Perched atop Wellesley's prestigious Cliff Estates, this beautifully renovated Victorian blends timeless architectural charm with modern comfort. Offering 4 bedrooms and 3.5 baths, the home has been thoughtfully updated while preserving its original character and period details. The sun-filled kitchen features a breakfast nook overlooking the landscaped backyard, while elegant living, dining, and music rooms provide ideal spaces for everyday living and entertaining. The second floor includes three spacious bedrooms, including a serene primary suite. The third level offers an additional bedroom, full bath, and a flexible bonus room perfect for a family room, home office, gym, or playroom. Enjoy a private patio, oversized detached two-car garage, and a picturesque setting in one of Wellesley's most sought-after area. A rare opportunity to own a home where historic elegance meets modern living.

8 Cypress Rd, Wellesley

$2,495,000

4 Beds ⋅ 4 Baths ⋅ NEW Status ⋅ 73574271 MLS ⋅ 3,746 SqFt.

Situated in the coveted Cliff Estates, this meticulously reconstructed contemporary home offers a sophisticated, light-filled interior designed for effortless modern living.This 4 bedroom, 4 full bathroom house is perfect for any stage in life. The main level features an open-concept flow anchored by an expansive gourmet kitchen with oversized island, vaulted ceilings and high end stainless steel appliances including a 6 burner Wolf range, Sub zero refrigerator, Bosch dishwasher, 2nd Bosch oven and microwave, Sub zero wine fridge and additional beverage fridges as well as ample counter space and storage in the butlers pantry. This space seamlessly transitions into a spacious dining area and a living room framed by custom built-ins and access to the backyard and patio. The home office is tucked away in the back of the house with custom built ins and two work stations. The upper level comprises the primary suite, complete with a generously proportioned walk-in closet with island and a marble-appointed bathroom with double sinks. There are two additional bedrooms and a full bathroom with double sink and tub/shower. A private fourth bedroom, located a few steps down, serves as an ideal guest or nanny suite with an adjacent full bath. Hardwood floors on all these levels. The lower level extends the footprint with a large family room/play room, a dedicated laundry area, an exercise area, custom storage, and another full bathroom. Set on a professionally landscaped, level lot, the exterior features a private bluestone patio overlooking a manicured lawn. The property combines quiet neighborhood privacy with exceptional convenience, located within one mile of public transit, local shopping, and major commuter routes.

54 Edmunds Rd, Wellesley

$2,195,000

5 Beds ⋅ 5 Baths ⋅ NEW Status ⋅ 73573935 MLS ⋅ 3,200 SqFt.

Completely gut-renovated from top to bottom, this stunning 5-bedroom, 3-bath home offers modern design and exceptional craftsmanship throughout. Renovated by a premier builder using top-quality materials, the home features a bright open-concept layout ideal for both everyday living and entertaining. The spacious kitchen flows seamlessly into the dining and living areas, creating an inviting central gathering space. A first-floor en-suite bedroom provides flexibility for guests, multigenerational living, or a private home office. Upstairs, additional bedrooms offer generous space and comfort. Located in a highly desirable neighborhood with convenient access to major routes, this home offers an easy commute to Boston while providing the comfort of a beautifully renovated residence ready for you to move right in.

6 Intervale Rd, Wellesley

$3,195,000

6 Beds ⋅ 5 Baths ⋅ NEW Status ⋅ 73573834 MLS ⋅ 6,034 SqFt.

Nestled on a quiet, tree-lined street just moments from Wellesley Town Center and the highly regarded Hunnewell Elementary School, this stunning six-bedroom home offers the perfect blend of luxury, comfort, and convenience. Thoughtfully designed with today’s lifestyle in mind, the expansive open floor plan seamlessly connects elegant living spaces, creating an inviting atmosphere for both everyday living and entertaining. Sun-drenched interiors showcase beautiful craftsmanship, generous proportions, and sophisticated finishes throughout. The chef’s kitchen flows effortlessly into the spacious family room, while formal and informal gathering spaces provide flexibility for every occasion. Six well-appointed bedrooms offer ample room for family, guests, and home offices. Outside, beautifully landscaped grounds provide a private retreat for relaxation and play. Ideally located near shops, restaurants, parks, schools and commuter routes.

1 Kenilworth Circle, Wellesley

$3,995,000

5 Beds ⋅ 6 Baths ⋅ NEW Status ⋅ 73573659 MLS ⋅ 5,059 SqFt.

Nestled in one of the area's most coveted neighborhoods with a seamless commute to Boston, this exceptional residence offers the perfect balance of luxury, privacy, and convenience. Thoughtfully gut-renovated with the finest materials and craftsmanship, the home showcases an open-concept floor plan designed for both elegant entertaining and everyday living. Expansive windows flood the interiors with natural light, creating bright, inviting spaces even on the gloomiest days. At the heart of the home is a stunning designer kitchen complemented by a fully equipped catering butler's pantry. A spacious three-car garage and custom mudroom provide exceptional functionality for modern living. Flexible living spaces include two private offices, while generously sized bedrooms each enjoy their own dedicated bathrooms. The finished walkout lower level is bathed in natural light and offers abundant additional and flexible living space. Professionally landscaped grounds provide remarkable privacy .

39 Fairbanks Ave, Wellesley

$1,730,000

5 Beds ⋅ 4 Baths ⋅ NEW Status ⋅ 73573624 MLS ⋅ 4,471 SqFt.

Welcome to 9 Fells Circle, a beautifully updated home offering bright, spacious, and flexible living in a desirable Wellesley neighborhood. Featuring hardwood floors, a fireplaced living room, formal dining room, spacious family room, updated kitchen and baths, and central air. The unique multi-level layout provides comfortable separation between living and sleeping spaces.The spacious primary bedroom features a finished bonus/flex space just a few steps up, perfect for a private home office, fitness area, sitting room, or additional flexible living space. Generously sized bedrooms, a beautiful yard, and an attached garage complete the home. Conveniently located near Wellesley schools, shopping, dining, and major routes. First showings at the Open Houses this Saturday and Sunday!

9 Fells Circle, Wellesley

$1,375,000

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73572680 MLS ⋅ 1,570 SqFt.

Ideally located at the end of a quiet cul-de-sac, this inviting Colonial is just a short distance from town center, the commuter train, and schools. A welcoming living room with a gas fireplace and custom cabinetry sets the tone as you enter. The spacious, open-concept kitchen and dining area is bright and sunny, with a thoughtfully designed kitchen featuring a center island with seating—perfectly suited for everyday living and entertaining. A French door leads to a versatile den or home office, offering a tucked-away space for work or relaxation. The second and third floors provide flexible bedroom options, with access to an expanded third floor offering additional possibilities. Outside, the fantastic backyard adjacent to the Brook Path, features lush foliage and a level lawn ideal for outdoor fun and games. A wonderful home with space to grow, personalize, and enjoy for years to come!

7 Dexter Road, Wellesley

$2,695,000

5 Beds ⋅ 4 Baths ⋅ UNDER AGREEMENT Status ⋅ 73571045 MLS ⋅ 4,054 SqFt.

Set on a picturesque cul-de-sac in Wellesley’s coveted Poet's neighborhood, this exceptional home offers an ideal blend of sophisticated living and everyday comfort. An inviting open floor plan creates a seamless flow between the kitchen, dining, and living spaces, while thoughtfully designed formal and informal rooms provide flexibility for both entertaining and relaxed family living. Chef's kitchen with doubles ovens includes a breakfast room with a window seat and custom built- in cabinet and opens to the family room with doors leading to the expansive and private backyard. A dedicated home office offers a quiet and private workspace features French doors to the blue stone patio. An oversized mudroom keeps belongings neat and tidy. Five generously sized bedrooms including a serene Primary suite with soaring ceiling, picture windows and double walk in closets. Four other bedrooms provide exceptional versatility for family, guests, and additional living needs. Lower level features a playroom and potential to fully finish another 640 sq.ft. for added value. Ideally located in one of Wellesley’s most desirable neighborhoods, this special property offers an outstanding combination of space, functionality, and location. Picture perfect in a dream neighborhood!

104 Fairbanks Avenue, Wellesley

$1,995,000

4 Beds ⋅ 4 Baths ⋅ UNDER AGREEMENT Status ⋅ 73570070 MLS ⋅ 3,216 SqFt.

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

$3,595,000

6 Beds ⋅ 5 Baths ⋅ CONTINGENT Status ⋅ 73569459 MLS ⋅ 6,525 SqFt.

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

$4,695,000

6 Beds ⋅ 5 Baths ⋅ UNDER AGREEMENT Status ⋅ 73568535 MLS ⋅ 7,013 SqFt.

Picture-perfect and beautifully renovated, this fabulous sun-filled home is ideally located in Wellesley’s highly desirable Country Club neighborhood. From the moment you arrive, its exceptional curb appeal and timeless elegance make an unforgettable first impression. Inside, an abundance of natural light highlights the sophisticated design, beautiful finishes, and thoughtful attention to detail throughout.The gracious open-concept layout offers an effortless blend of formal and casual living, with elegant entertaining spaces flowing seamlessly into inviting family areas. The beautifully appointed kitchen is the heart of the home, designed for both everyday living and memorable gatherings. Two first floor custom built offices are ideal for work from home spaces. Spacious bedrooms provide comfort and privacy, while the luxurious primary suite offers a peaceful retreat. With six bedrooms and generous living spaces, the home is perfectly suited to modern family life and entertaining. A fabulous newer garage adds incredible versatility, including a dedicated gym/loft and ample space for vehicles, equipment, and storage. The impressive lower level features a recreation room, arts & craft area, au pair suite/bedroom with an adjacent full bathroom. Every room feels fresh, refined, and welcoming, creating that rare combination of sophisticated style and comfortable living. Set in one of Wellesley’s most sought-after neighborhoods, this exceptional residence offers an idyllic setting close to all that Wellesley has to offer. Much admired home!!!!

32 Arlington Road, Wellesley

$1,395,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73566903 MLS ⋅ 1,800 SqFt.

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

$1,475,000

3 Beds ⋅ 2 Baths ⋅ UNDER AGREEMENT Status ⋅ 73566375 MLS ⋅ 2,496 SqFt.

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

$1,980,000

4 Beds ⋅ 4 Baths ⋅ UNDER AGREEMENT Status ⋅ 73565625 MLS ⋅ 3,136 SqFt.

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

$1,950,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73565252 MLS ⋅ 1,595 SqFt.

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

$1,675,000

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 73562667 MLS ⋅ 2,086 SqFt.

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

$1,980,000

4 Beds ⋅ 3 Baths ⋅ PRICE CHANGED Status ⋅ 73562429 MLS ⋅ 3,330 SqFt.

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

$1,099,999

4 Beds ⋅ 2 Baths ⋅ UNDER AGREEMENT Status ⋅ 73557701 MLS ⋅ 1,514 SqFt.

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

$3,250,000

4 Beds ⋅ 4 Baths ⋅ UNDER AGREEMENT Status ⋅ 73551561 MLS ⋅ 3,712 SqFt.

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

$1,450,000

3 Beds ⋅ 3 Baths ⋅ PRICE CHANGED Status ⋅ 73547678 MLS ⋅ 2,447 SqFt.

Set on a quiet residential cul-de-sac, this thoughtfully renovated 3-bedroom, 3-bath home offers a host of upgrades designed for effortless everyday living. The kitchen flows naturally into the sun-drenched dining room, where windows on three sides and one of three wood-burning fireplaces add warmth and character to the space. Together they look out over an expansive backyard, where a paver patio and mature landscaping create a private outdoor retreat perfect for entertaining or simply unwinding after a long day. Downstairs, the finished lower level adds tremendous flexibility with a secondary living room, a private office, a full bathroom, ample storage, and direct access to the garage. Close to Wellesley's town center, middle school, and high school, this is a home that truly has it all.

44 Windemere Rd, Wellesley

$1,198,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73547038 MLS ⋅ 1,813 SqFt.

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. Open House Sunday 9/13 from 1pm - 3pm!

296 Linden St., Wellesley

$1,275,000

3 Beds ⋅ 3 Baths ⋅ BACK ON MARKET Status ⋅ 73545904 MLS ⋅ 1,848 SqFt.

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

$4,995,000

6 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 73545332 MLS ⋅ 7,738 SqFt.

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

$1,399,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73545066 MLS ⋅ 1,320 SqFt.

**** 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

$1,490,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73542088 MLS ⋅ 2,218 SqFt.

Meticulously updated and turnkey move in!32 Bobolink Rd combines classic charm with modern conveniences. Recent improvements including a new roof, updated HVAC systems & interior upgrades,unbeatable location close to all the Wellesley top schools, parks, shopping, and commuter routes.Bright and spacious raise ranch house which located on a quiet street. Gleaming hardwood floors , open concept updated kitchen with maple cabinets and granite countertops. The spacious living and dining areas flow effortlessly into a welcoming family room with sliding doors leading to a private patio—perfect for entertaining or relaxing outdoors. Master bedroom comes with a bonus room, two more bedrooms on the 1st level with lots of storage space. Lower level is a finished basement, comes with one more bedroom, full bath, laundry, mudroom and access to the attached two car garages. Fenced in yard, minutes from Schofield Elementery School. Don't miss your chance to make 32 Bobolink Rd your new home!

32 Bobolink Rd, Wellesley

$3,299,000

6 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 73542007 MLS ⋅ 4,424 SqFt.

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

$1,485,000

3 Beds ⋅ 2 Baths ⋅ UNDER AGREEMENT Status ⋅ 73539867 MLS ⋅ 1,835 SqFt.

This charming Bungalow with an inviting front porch complete with a swing, will steal your heart. A gracious foyer leads to a sun-filled open concept living room & kitchen for easy everyday living. The separate dining room is perfect for entertaining. The versatile first floor includes a full bath & laundry room and a bonus room offering flexibility as a home office, guest room, playroom & a mudroom. The 2nd floor has 3 generous bedrooms and a luxurious spa-like bath room featuring double sinks, a soaking tub, & a stall shower. Step outside to enjoy a terrific fenced in backyard and deck—ideal for pets and relaxing summer evenings with family & friends. Perfectly situated a short distance to the vibrant Linden Square shops & restaurants, public schools, and Commuter Train. Experience the best of both worlds, where urban convenience meets the peace, space and charm of the suburbs. It is the home you have been waiting for and one not to miss!

20 Hill Top Rd, Wellesley

$1,300,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73537936 MLS ⋅ 1,640 SqFt.

Lovely Cottage on Morses Pond with stunning waterfront views, it's as if you are on a vacation everyday. Extensively renovated & thoughtfully reimagined to showcase the natural beauty of its surroundings with an easy open concept design. The 1st floor's spacious living room has a fireplace & built-ins that flow seamlessly to a timeless white shaker cabinetry kitchen w/SS appliances, marble & center island w/ seating. The adjacent dining room with a large bay window & window seat, is a wonderful spot for your morning coffee or sunset dinners. The 2nd floor has 3 well proportioned bedrooms all with terrific closet space, a full bath & laundry. Bonus rooms in the walk out lower level, offer flexibility for a home office, playroom or workroom. Outdoor fun all year round in a vibrant neighborhood, enjoy kayaking, canoeing to ice skating from your backyard. Relax at the end of the day on the wrap around deck watching the swans drift by on the pond. Surround yourself with nature and take in the tranquility of this special home.

30R Morses Pond Road, Wellesley

$1,299,000

4 Beds ⋅ 2 Baths ⋅ UNDER AGREEMENT Status ⋅ 73535428 MLS ⋅ 2,233 SqFt.

Wonderful opportunity to own an affordable two-family home in Wellesley. Don't miss this charming two-family home nestled in a desirable neighborhood setting — rich in character and architectural detail with a stunning wrap-around porch that sets it apart. Each unit offers 2 bedrooms, updated electrical service, and a large detached 2-car garage adds exceptional value. Commuters will love the easy highway access, while the generous 13,000 SF lot offers ideal outdoor space with lots of possibilities.

31 Lantern Lane, Wellesley

$1,895,000

4 Beds ⋅ 3 Baths ⋅ PRICE CHANGED Status ⋅ 73533550 MLS ⋅ 2,896 SqFt.

Tucked away on a quiet private lane in the heart of Wellesley Hills, this beautifully updated farmhouse seamlessly blends timeless character with modern comfort. Offering exceptional privacy while just moments from the train, shops, restaurants, and everyday conveniences, this distinctive home delivers the best of walkable village living.A welcoming front porch sets the tone for the warm and inviting interiors, where high ceilings, abundant natural light, and thoughtful architectural details create an effortless flow throughout. The spacious kitchen opens to a sun-filled family room, forming the heart of the home and an ideal setting for both everyday living and entertaining. Elegant living and dining rooms feature fireplaces, crown moldings, and classic details that reflect the home's rich heritage.The serene primary suite serves as a private retreat, highlighted by a stylishly renovated bath. Three additional bedrooms and convenient second-floor laundry complete the upper level.Adding to the home's versatility is an exceptional bonus space above the detached two-car garage, perfect for a home office, fitness studio, creative workspace, guest overflow, or potential future accessory dwelling unit. Outdoors, multiple porches, a patio, and beautifully landscaped grounds provide inviting spaces for relaxation, gathering, and enjoying the peaceful setting.A rare offering that combines historic charm, modern updates, flexible living space, and an unbeatable Wellesley Hills location.

40 Kimlo Rd, Wellesley

$2,500,000

4 Beds ⋅ 5 Baths ⋅ UNDER AGREEMENT Status ⋅ 73533506 MLS ⋅ 2,998 SqFt.

Set on a naturalized landscaped oversized lot in a sought-after Wellesley location, this sun-filled Arts and Crafts residence blends timeless character with refined versatility. Thoughtfully expanded with custom architectural details, the home offers primary suites on both the first and second floors, generous additional bedrooms and baths, and flexible spaces for work, guests, or quiet retreats. Skylights, fireplaces, and vaulted ceilings bring warmth, light, and scale throughout, and the landscaped grounds and specimen plantings complete the setting.•4 bedrooms, including primary suites on both the first and second floors•3 full baths and 2 half baths•Skylights, fireplaces, and vaulted ceilings throughout•Thoughtful expansion featuring custom architectural details•Spacious two-car garage with attached workroom•Lower level provides generous storage and oversized playroom •Outdoor patio. Plant lovers paradise . Near Town center/Dana Hall, Hunnewell School, library. West facing sunsets.

42 Temple Road, Wellesley

$2,599,000

5 Beds ⋅ 4 Baths ⋅ UNDER AGREEMENT Status ⋅ 73529084 MLS ⋅ 5,428 SqFt.

Located in the coveted Cliff Estates, this beautifully expanded 13-room, 5,428 sq ft Garrison Colonial with contemporary addition is ideally set on a quiet cul-de-sac and surrounded by nature. The thoughtfully designed first floor features an updated kitchen with oversized island, pantry, abundant storage, and seamless flow into the spacious family room with custom windows and built-ins. Formal living and dining rooms, study, and two fireplaces create warm and inviting spaces for everyday living and entertaining. A first-floor guest bedroom with en-suite full bath offers flexibility for guests or extended family. Upstairs includes 4 spacious bedrooms, highlighted by the primary suite with double-sink bath and dual walk-in closets. Finished lower level offers three large and flexible office, play or fitness rooms plus a half-bath. Elevated deck overlooks private tree-lined yard.

22 Tanglewood Road, Wellesley

$1,100,000

5 Beds ⋅ 2 Baths ⋅ UNDER AGREEMENT Status ⋅ 73514443 MLS ⋅ 1,712 SqFt.

Amazing opportunity in an established neighborhood with convenient access to Route 9! Situated on a .27-acre lot, this property offers incredible potential for investors, builders, or buyers looking to create their dream home. The existing structure will most likely require a tear-down, making this the perfect chance to design and build new in a desirable location. Don’t miss this rare opportunity to bring your vision to life! BEST & HIGHEST DUE BY MONDAY MAY 11, 2026 AT 4;00 PM

9 Larch Rd, Wellesley

$2,250,000

8 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 73503039 MLS ⋅ 5,559 SqFt.

Ideally located in the heart of Wellesley Center, 9–11 Hampden Street is a rare offering of gracious proportion, charm and timeless detail. With nearly 5,600 sq. ft. of living space across three sun-splashed finished floors, this stately residence offers 8 bedrooms and versatile living areas awaiting a discerning buyer’s vision. Sited on .37 acres, with a freshly painted interior, it is equally compelling as a grand single-family home or as an investment with its current 2-family configuration. Rich in history, the property was long associated with Helen Temple Cooke, pioneering educator and head of the Dana Hall School from 1899-1955. Currently owned for a second time by Dana Hall, the home blends historic character with an unrivaled in-town location - just a block to the train, shops, restaurants, and the beloved Brook Path. A unique opportunity to create a signature residence or phenomenal addition to your investment portfolio in one of Wellesley’s most coveted neighborhoods!

9-11 Hampden Street, Wellesley

$2,250,000

8 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 73503038 MLS ⋅ 5,559 SqFt.

Ideally located in the heart of Wellesley Center, 9–11 Hampden Street is a rare offering of gracious proportion, charm and timeless detail. With nearly 5,600 sq. ft. of living space across three sun-splashed finished floors, this stately residence offers 8 bedrooms and versatile living areas awaiting a discerning buyer’s vision. Sited on .37 acres, with a freshly painted interior, it is equally compelling as a grand single-family home or as an investment with its current 2-family configuration. Rich in history, the property was long associated with Helen Temple Cooke, pioneering educator and head of the Dana Hall School from 1899-1955. Currently owned for a second time by Dana Hall, the home blends historic character with an unrivaled in-town location - just a block to the train, shops, restaurants, and the beloved Brook Path. A unique opportunity to create a signature residence or phenomenal addition to your investment portfolio in one of Wellesley’s most coveted neighborhoods!

9-11 Hampden Street, Wellesley

$1,575,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73499017 MLS ⋅ 3,012 SqFt.

Wake up to sparkling water views from every room. Sip morning coffee and enjoy the wildlife from your deck. River views can be enjoyed from nearly every room and are especially striking from the expansive glass-enclosed sunroom where the landscape changes with the season. Recent upgrades include a new roof, HVAC, full interior and exterior painting, windows, doors, and more. The open, flexible layout is ideal for entertaining, creative living, and working from home. Set among lush perennial gardens, this unique home offers abundant privacy and a peaceful natural backdrop. A truly special home in an extraordinary natural setting. Ideally located with easy access to Wellesley Center and minutes from South Natick, Elm Bank Reservation, and the historic Bacon Free Library.

30 S River St, Wellesley

$1,100,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73497359 MLS ⋅ 2,165 SqFt.

A great opportunity for a buyer who understands the value of sweat equity and is willing to make some improvements! This delightfully charming Cape style home offers a versatile open concept floor plan. The first floor flows seamlessly to two separate fireplace living areas as well as a dining room with hardwood flooring throughout. The updated kitchen boasts granite countertops, stainless appliances, ample storage and breakfast bar and opens to a large rear deck, perfect for entertaining. Upstairs boasts a large en-suite Primary bedroom, two additional bedrooms, another full bath along with an office/den bonus space. There are plenty of custom built-ins, cabinets and quaint nooks that make this an adorable gem of a home. The acreage is combined lots 6 & 6R and offers a half acre of privacy or possible room to grow. The home needs some exterior and basement improvements to reimagine it to your dream! Terrific location, moments to Fiske elementary school & easy access to Rt.9,128.

6 Willow Street, Wellesley

$2,890,000

4 Beds ⋅ 4 Baths ⋅ UNDER AGREEMENT Status ⋅ 73482936 MLS ⋅ 3,334 SqFt.

Incredible opportunity to own a rare, conforming one-acre lot in the heart of Cliff Estates! This 4-bedroom, 4-bath home offers exceptional potential and is ready for its next chapter. Bring your vision and reimagine the possibilities in this highly desirable location. Easy to show!

162 Hampshire Rd, Wellesley

$2,890,000

4 Beds ⋅ 4 Baths ⋅ UNDER AGREEMENT Status ⋅ 73482935 MLS ⋅ 3,334 SqFt.

Incredible opportunity to own a rare, conforming one-acre lot in the heart of Cliff Estates! This 4-bedroom, 4-bath home offers exceptional potential and is ready for its next chapter. Bring your vision and reimagine the possibilities in this highly desirable location. Easy to show!

162 Hampshire Rd, Wellesley

$2,299,000

5 Beds ⋅ 4 Baths ⋅ UNDER AGREEMENT Status ⋅ 73473045 MLS ⋅ 3,398 SqFt.

5 bedroom home on Morses Pond with the most incredible water views. Swim, paddle board, kayak or fish from your own backyard. Large open kitchen family room with full picture windows offering stunning views of the pond. Kitchen with stainless appliances and large island. Dining room/sunroom with access to deck with more water views. Living room with fireplace and built-ins. First floor den. Main suite also focuses on water views with new bathroom as well as walk-in closet. 2 additional bedrooms on 2nd floor with another updated bath. Large office on the 2nd floor. 3rd floor with 2 additional bedrooms- one with Juliet balcony and 3rd full bathroom. Lower level perfect for storage plus playroom/ exercise area. NEW: boiler, wet bar, flooring, master bath, 2nd floor bath and powder room. Recent updates make this home ready to move right in. Enjoy peaceful living and enjoy this view all 4 seasons of the year.

31 College Road, Wellesley

$3,400,000

10 Beds ⋅ 9 Baths ⋅ ACTIVE Status ⋅ 73445436 MLS ⋅ 10,318 SqFt.

Rare Investment Opportunity in the Heart of Wellesley Square! Offered for the first time in almost 80 years, this exceptional TWO BUILDING/multi-family property is a rare find in one of Metro Boston’s most desirable communities. Situated on a quiet street just steps from vibrant Wellesley Square, this unique offering includes two buildings with a total of 7/8 units, providing excellent long-term income and countless possibilities for the savvy investor or owner-occupant. Live in one unit and let the other units work for you, or hold as a high-performing rental property with significant upside. This is an excellent opportunity to own in a prime Wellesley location — enjoy restaurants, boutique shops, the Commuter Rail, Wellesley College, and the Wellesley Library. Enjoy unbeatable access to Routes 16, 9, 95, and the Mass Pike, making commuting and travel effortless. Whether you're looking to invest, convert, or plant roots in a world-class community, this property delivers!

5-7 Abbott Street, Wellesley

$4,895,000

7 Beds ⋅ 7 Baths ⋅ PRICE CHANGED Status ⋅ 73376559 MLS ⋅ 7,262 SqFt.

Much admired 7 bedroom, 7000+sf estate home on an acre of manicured lawns on famed Cliff Road. Built and re designed by two of New England’s most acclaimed architects, this home boasts the grandeur of stately proportions and sumptuous millwork with a newly renovated and superbly equipped chef’s Kitchen and butler’s pantry with adjacent family room. A banquet sized dining room and gracious living room both with fireplaces and french doors lead to the private grounds with stone walls, built in grill and multiple sitting areas. Handsome mahogany study with fireplace, ensuite bedroom with newly renovated bath plus a separate sun room complete the 1st floor. Up a curved staircase befitting the most prestigious of homes you will find 6 bedrooms and 4 full baths including the primary suite with, luxurious bath and laundry. Lower level with recreation room and state of the art wine cellar, 3 car heated garage, heated driveway and whole house generator. A once in a lifetime opportunity!

200 Cliff Rd, Wellesley

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