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16 Oak Street, Wellesley
$2,480,000
5 Beds ⋅ 5 Baths ⋅ 73485740 MLS
Sun-splashed historic renovation of an in-town Colonial offering 5 bedrooms, 3 full baths, and 2 half baths. This stunning home blends timeless character with modern comfort, featuring high ceilings, spacious living areas, and a finished walkout basement ideal for a home office, gym, or entertaining. The chef’s kitchen includes a 72-inch fridge/freezer, a large island, a pantry, and opens to a patio with a fire pit. Additional highlights include a farmer’s porch, a generous mudroom, and an oversized detached 2-car garage with two floors of storage. Updated throughout with new wiring, energy-efficient heating and cooling, insulation, windows, and a tankless hot water system. The large yard offers ample space. Perfectly located just steps to Wellesley’s restaurants, schools, train, and downtown, in General Residence zoning allowing for future development potential of a legal second unit.

16 Oak Street, Wellesley

Listing courtesy of Listing Agent: Joseph T. Fleming from Listing Office: JT Fleming & Company.
148 Weston Rd Unit 304, Wellesley
$2,450,000
2 Beds ⋅ 2 Baths ⋅ 73525506 MLS ⋅ ['The Bristol'] BLDG.
Experience elevated luxury living at The Bristol, Wellesley’s premier boutique condo development designed for those seeking effortless sophistication & every modern convenience. This exceptional, fully furnished, penthouse home showcases soaring 9' ceilings, white oak flooring & impeccably curated finishes throughout. The designer kitchen is both striking & functional, featuring a waterfall island w/ seating for 4, seamless walnut & glass cabinetry, handmade subway tile backsplash, Wolf appliances & Sub-Zero refrigeration. The elegant living room is anchored by a gas fireplace & a private balcony through oversized french doors. The serene primary suite offers a spa-like bath with frameless glass shower, bench seating, double vanity, water closet & linen storage. A 2nd bedroom, full hall bath & laundry complete the thoughtful layout. Expansive private roof deck & custom California Closets & automated Hunter Douglas blinds throughout. 8am-9pm concierge service, 2 deeded garage spaces.

148 Weston Rd Unit 304, Wellesley

Listing courtesy of Listing Agent: Beyond Boston Properties Group from Listing Office: Compass.
79 Alba Rd, Wellesley
$2,450,000
4 Beds ⋅ 5 Baths ⋅ 73505434 MLS
Thoughtfully renovated and expanded in 2022, this stunning home blends classic charm with modern open living. Every detail has been updated with care. The large eat-in kitchen, anchored by an oversized island and featuring a generous pantry, flows seamlessly into the main living space — perfect for everyday living and entertaining.Flexible layout offers space for two home offices. The expansive primary suite features two generous closets and a spa-like en-suite bath. Two additional bedrooms share a second full bath, while a third bedroom enjoys its own en-suite. Convenient laundry completes the upper level. The finished basement delivers it all — a home gym, entertainment area, kids' play space, and dedicated storage. A large one-car garage adds everyday ease. All of this in Wellesley's most walkable neighborhood — steps to Sprague Elementary, Wellesley Middle and High Schools, the commuter rail, and the charming shops of Linden Street, Wellesley Square, and Wellesley Hills.

79 Alba Rd, Wellesley

Listing courtesy of Listing Agent: Steve & Nicole Connolly Group from Listing Office: Coldwell Banker Realty - Wellesley.
48 Patton Road, Wellesley
$2,450,000
5 Beds ⋅ 4 Baths ⋅ 73481582 MLS
Bathed in natural light, this beautifully maintained home offers a seamless open floor plan designed for both everyday living & perfect for entertaining. Spacious fireplaced living room flows effortlessly into a well-appointed kitchen with dining area. Stunning family room overlooks the expansive fenced & beautifully manicured private yard & patio. Five generously sized bedrooms offer ample space for family, guests, or flexible use. A fabulous private office with high ceiling provides the perfect work-from-home retreat, filled with sunlight. Impeccable renovated mudroom keeps belongings neat & tidy in style. Whether hosting gatherings, enjoying quiet moments, or balancing work & life, this home adapts beautifully to every need. Combining space, light & timeless upkeep, it offers an exceptional setting to live, work, and entertain with ease and sophistication. Close proximity to all that Wellesley has to offer; vibrant town center, Morses Pond, trails & the Hardy Elementary School.

48 Patton Road, Wellesley

Listing courtesy of Listing Agent: The Lara & Chelsea Collaborative from Listing Office: Coldwell Banker Realty - Wellesley.
78 Denton Rd, Wellesley
$2,450,000
6 Beds ⋅ 4 Baths ⋅ 73480266 MLS
Set in everyone's favorite Dana Hall neighborhood, this classic 1920 Colonial blends timeless charm w/ the space and updates you'd hoped for. 6 bedrooms and 3.5 beautifully updated baths (most with heated flooring), this gracious home is designed for gatherings in mind offering plenty of entertaining spaces all while maintaining the warmth and character you'd expect from its era. A welcoming covered front porch sets the tone and leads to a fireplaced entry foyer, you'll fall in love right there! The kitchen features granite countertops, stainless steel appliances (including Sub-Zero & Viking) and connects to an entertainment space w/ wine fridge, additional fridge and freezer drawers and ice maker. The family room features a second fireplace and is large enough for the entire family, the dining room boasts a bay window with room for everyone at the table. Finished basement, oversized mudroom w/ heated floor, fenced yard, A/C, incredible outdoor space and 2-car garage - close to it all!

78 Denton Rd, Wellesley

Listing courtesy of Listing Agent: Betsy Kessler from Listing Office: Rutledge Properties.
40 Chestnut Street, Wellesley
$2,450,000
5 Beds ⋅ 4 Baths ⋅ 73474474 MLS
Sunday Open House Canceled! Brimming with charm and fine detail, 40 Chestnut Street, Wellesley, MA 02481 is a sun-splashed Shingle-style home with a wraparound porch on a coveted Wellesley Farms street. A welcoming foyer with a turned staircase opens to inviting living and dining rooms, plus a sunlit eat-in kitchen with marble countertops and backsplash and premium appliances. 5 bedrooms and 3.5 baths include a primary suite with a sitting room or office, along with two additional bedrooms on the third floor. Enjoy a finished lower level, landscaped grounds, and a patio. Major improvements include a new two-car garage, EV-ready 200-amp underground electrical service, and a high-efficiency Carrier Infinity gas and heat pump HVAC system, plus MassSave insulation, restored windows, Ethernet wiring, refreshed hall bath, and fresh interior paint. Close to Wellesley Square, the commuter rail, Route 9, I-95/128 and the Mass Pike. Classic character and a standout Wellesley address.

40 Chestnut Street, Wellesley

Listing courtesy of Listing Agent: Paul Neavyn from Listing Office: Gibson Sotheby's International Realty.
30 Southgate Road, Wellesley
$2,405,000
4 Beds ⋅ 3 Baths ⋅ 73429178 MLS
Beautifully sited in one of Wellesley's most desirable neighborhoods, this classic Colonial offers easy access to the Brook Path, commuter rail to Boston, top-rated schools, playgrounds, and Wellesley's vibrant downtown. The expansive kitchen features a generous center island & sunny breakfast area with French doors leading to the stunning patio with built-in grill, frig & fire pit. The dining & family rooms flow seamlessly into the kitchen—ideal for everyday living and entertaining. Step into the inviting three-season porch, which opens to a beautifully landscaped, private backyard haven. A charming see-through fireplace adds warmth & character between the living and family rooms. Upstairs, you’ll find 4 bedrooms & 2 baths including a primary bedroom with cathedral ceiling and en suite bath. The finished lower level offers versatile bonus space for game room, home gym, crafts, hobbies, music studio, media room. Don't miss this exceptional home—this is the one you've been waiting for

30 Southgate Road, Wellesley

Listing courtesy of Listing Agent: Jane Collinson from Listing Office: Gibson Sotheby's International Realty.
16 Denton Rd, Wellesley
$2,400,000
5 Beds ⋅ 3 Baths ⋅ 73509556 MLS
A stunning Colonial in the coveted Hunnewell district offers the perfect blend of timeless elegance & in-town convenience. Ideally situated just moments from Wellesley Center, this beautifully maintained home showcases sun-filled interiors, gleaming hardwood floors, & refined architectural details throughout. A gracious front entry opens to inviting formal living & dining rooms, while the updated kitchen seamlessly connects to gracious covered porch ideal for everyday living and entertaining. Upstairs, generous bedrooms provide comfort and flexibility, including a serene primary suite. Thoughtful updates enhance the home’s classic charm while meeting modern needs. Outside, a private, landscaped yard offers a peaceful retreat. Enjoy an unparalleled walk-to-everything lifestyle with easy access to shops, restaurants, Fuller Brook path, parks, top-rated schools, and the commuter rail. This exceptional property captures the very best of Wellesley living—sophisticated and convenient!

16 Denton Rd, Wellesley

Listing courtesy of Listing Agent: The Lara & Chelsea Collaborative from Listing Office: Coldwell Banker Realty - Wellesley.
70 Curve St, Wellesley
$2,400,000
5 Beds ⋅ 4 Baths ⋅ 73507852 MLS
Glorious, bright and sunny shingle-style home in wonderful Wellesley Center neighborhood. Built for Katherine Lee Bates, author of America the Beautiful, who lived & wrote here, including in the 3rd-floor sanctuary she called “Bohemia.” Set back & framed by mature trees, the home blends historic character w/ gorgeous updates for modern family living & gracious entertaining. Stunning architectural details throughout, incl. wide open foyer, light-filled updated kitchen, rich fir flooring, oversized windows & charming porches at every turn. 4 corner BRs, including a beautiful primary suite with porch on 2nd floor. Breathtaking 3rd-floor retreat offers soaring ceilings, white shiplap paneling, a flood of natural light, along with a coffee bar, ensuite bath, dressing room, and laundry, ideal as a second primary suite, inspiring studio, home office, or game room. Finished playroom and extra storage in LL. Close walk to Wellesley Center shops, library, train, and Sprague School.

70 Curve St, Wellesley

Listing courtesy of Listing Agent: Roberta Swenson from Listing Office: Rutledge Properties.
98 Great Plain Ave, Wellesley
$2,400,000
4 Beds ⋅ 4 Baths ⋅ 73428733 MLS
Step into 98 Great Plain Avenue—a newly transformed residence where modern sophistication meets classic appeal. Flooded with natural light, this exceptional home features soaring ceilings and a thoughtfully designed open-concept layout tailored to contemporary living. Rich hardwood floors and premium finishes define every inch of the interior, creating a refined yet welcoming ambiance. The chef’s kitchen is a showstopper, complete with sleek granite countertops, custom cabinetry, and top-tier appliances. Expansive living and dining spaces offer seamless flow, ideal for hosting or relaxing in style. Upstairs, tranquil bedrooms and spa-inspired baths provide a restful escape. Outside, enjoy a large, level yard with a beautifully designed terrace—perfect for entertaining, play, or peaceful evenings. A spacious two-car attached garage rounds out this impeccable offering. Don’t miss the chance to own this turnkey gem in a coveted location.

98 Great Plain Ave, Wellesley

Listing courtesy of Listing Agent: Prudence B. Hay from Listing Office: Rutledge Properties.
11 Shadow Ln, Wellesley
$2,367,500
4 Beds ⋅ 5 Baths ⋅ 73552192 MLS
Nestled on a quiet cul-de-sac near Morses Pond and Wellesley's renowned trail network, this modern Colonial offers 3,750 sq ft across three finished levels. A gracious foyer opens to formal living and dining rooms, while the sun-filled family room with fireplace flows seamlessly into the renovated chef's kitchen featuring Viking and Miele appliances, quartz countertops, center island, breakfast nook, and access to the deck overlooking the private fenced backyard. Upstairs, the spacious primary suite offers a luxurious bath and oversized walk-in closet, accompanied by three additional bedrooms, including one en suite, a full bath, and second-floor laundry. The finished lower level features an expansive recreation room, media room, bar area, exercise space, powder room, and abundant storage. Convenient to Wellesley Center, top-rated schools, shopping, commuter routes, and outdoor recreation.

11 Shadow Ln, Wellesley

Listing courtesy of Listing Agent: Marjorie Gold from Listing Office: Hammond Residential Real Estate.
28 Clovelly, Wellesley
$2,354,000
4 Beds ⋅ 5 Baths ⋅ 73444251 MLS
Classic Colonial set in Wellesley’s coveted Country Club neighborhood, this classic 4-bedroom Colonial offers timeless appeal, lush surroundings, and a walk-to-everything lifestyle. Beautifully sited amid mature plantings, the home features inviting spaces filled with warmth and character. The gracious dining room with fireplace creates an ideal setting for entertaining, with adjoining sunlit living room, spacious kitchen, adjoining family room and private study provide comfortable everyday living. Upstairs, four well-proportioned bedrooms with an en-suite primary offer flexibility for family and guests. The lower level has a large home gym and private office space. Enjoy a prime location just moments from Wellesley’s vibrant shops, restaurants, and train — all in one of the town’s most sought-after settings. You will love the feeling of privacy, being surrounded by nature yet just moments away from all that Wellesley has to offer.

28 Clovelly, Wellesley

Listing courtesy of Listing Agent: Gail Lockberg from Listing Office: Berkshire Hathaway HomeServices Town and Country Real Estate.
7 Bemis Rd, Wellesley
$2,350,000
5 Beds ⋅ 6 Baths ⋅ 73488948 MLS
Built in 2018 and set on a sun-filled, level lot tucked quietly off the street, this contemporary home offers exceptional privacy with unbeatable convenience, just minutes to Wellesley Hills Station, cafes, Brook Path, and top schools. The thoughtfully designed open layout features a bright kitchen/family room with coffered ceilings, gas fireplace, and top-tier appliances. 5 bedrooms and 4.5 marble-appointed baths offer flexible living for every need. The 2nd floor features a luxurious primary suite with a spa-like primary bath, along with three additional bedrooms ideal for family living. A private 3rd floor suite with full bath provides a perfect retreat for guests or extended family. The walk-out lower level offers 9-foot ceilings, a full bath, and flexible living space. Landscaped grounds include a flat play yard, mature evergreens for privacy, bluestone patios, and elegant stonework. The two-car garage includes an EV charger. A perfect blend of modern luxury and in-town living.

7 Bemis Rd, Wellesley

Listing courtesy of Listing Agent: Dream Team from Listing Office: Dreamega International Realty LLC.
28 Emerson Rd, Wellesley
$2,325,000
3 Beds ⋅ 3 Baths ⋅ 73512437 MLS
Warm and inviting, this brick Tudor with a classic slate roof is ideally situated in Wellesley’s sought-after Poet’s Corner. Thoughtful updates blend effortlessly with the home’s timeless character and architectural detail. A granite and stainless steel kitchen with center island flows beautifully into a newly added family room w/ fireplace and soaring ceiling, creating the perfect hub for everyday living and entertaining, with easy access to the expansive deck and level backyard. The living room with fireplace offers generous space to gather, complemented by a flexible sunroom ideal for a home office or quiet retreat. The second floor features a primary suite with fireplace, walk-in closet, and en suite bath, along with two additional bedrooms and a full bath. C/A, 2-car garage. Enjoy a convenient location just minutes from the Wellesley Rec Center, Warren Park, Lower Falls shops and restaurants, commuter rail, and major routes.

28 Emerson Rd, Wellesley

Listing courtesy of Listing Agent: Betsy Kessler from Listing Office: Rutledge Properties.
53 Audubon Rd, Wellesley
$2,325,000
4 Beds ⋅ 4 Baths ⋅ 73509644 MLS
This much-admired Colonial with amazing curb appeal is located in the coveted Cliff Estates neighborhood in Wellesley Hills! Perfect for comfortable living and gracious entertaining, this home has a large front-to-back living room with fireplace and classic period details. There is a lovely formal dining room and an updated eat-in kitchen with an island, granite countertops, and stainless appliances. The sunny breakfast area opens to a deck and patio. A warm and comfortable family room leads to a reading nook with a window seat and home office. A generous mudroom leads to a two-car attached garage. The second level includes a master suite, two additional bedrooms, and a hall bath. A large, private bedroom suite with full bath over the garage is perfect for guests. The lower level offers a large playroom and great storage space. The private, level backyard with mature plantings and patio is perfect for entertaining. Easy access to schools, shopping & commuter rail.

53 Audubon Rd, Wellesley

Listing courtesy of Listing Agent: The Madden David Real Estate Group from Listing Office: Coldwell Banker Realty - Wellesley.
99 Parker Road, Wellesley
$2,315,000
4 Beds ⋅ 3 Baths ⋅ 73536634 MLS
Nestled on a tranquil tree-lined street, this sun-filled expanded & spacious Cape will impress you at every turn! The front porch surrounded by lush landscaping is the perfect spot for morning coffee or lazy afternoons. When you step inside you will be amazed by the amount of living space. The open concept family room includes a wall of windows highlighting the scenic view, a magnificent stone fireplace & leads to the newly renovated stylish kitchen; creating an airy atmosphere for family gatherings. Relax, read & work from home in the beautiful library with soaring ceiling & custom built-ins. Rare first floor bedroom is ideal for guests/ au-pair. The second floor has the primary bedroom w/ a dressing room, full bathroom w/ double vanity & two additional bedrooms & full bath/ laundry. Fantastic lower level is a surprise with a playroom, game room & bonus room- wow! Outdoor setting is a nature lovers dream with lovely views & patio for entertaining. Beloved neighborhood near Perin Park.

99 Parker Road, Wellesley

Listing courtesy of Listing Agent: The Lara & Chelsea Collaborative from Listing Office: Coldwell Banker Realty - Wellesley.
81 Audubon Road, Wellesley
$2,300,000
5 Beds ⋅ 4 Baths ⋅ 73482350 MLS
Welcome home to this wonderful Colonial. The fireplaced living room has beautiful cabinets and the adjacent sunny office space makes working from home a pleasure. The dining room with a custom built-in, is ready for holidays and celebrations, while the newly updated kitchen truly serves as the heart of the home. Featuring ample cabinetry, Cambria quartz countertops, stainless steel appliances, and generous prep space, it opens directly to a stunning family room with a beautifully designed wet bar. The oversized mudroom is a dream for busy households, complete with heated floors, built-ins, and plenty of closet space to keep you organized. Upstairs, the second floor offers three spacious bedrooms, while the third floor provides two additional bedrooms.There is a show stopping closet in the primary. The finished lower level adds even more flexibility with a gym and playroom. Outside, the large yard offers plenty of grassy space to play and pergula atop a bluestone patio. Wow!

81 Audubon Road, Wellesley

Listing courtesy of Listing Agent: Teri Adler from Listing Office: MGS Group Real Estate LTD - Wellesley.
25 Hillside Rd, Wellesley
$2,280,000
5 Beds ⋅ 6 Baths ⋅ 73553688 MLS
Nestled in the prestigious Wellesley Farms neighborhood, this enchanting brick estate is set on over 35,000 square feet of beautiful grounds, offering exceptional privacy and timeless elegance. A grand foyer welcomes you into a thoughtfully designed home featuring five spacious bedrooms and four full bathrooms. Rich architectural details, grand living spaces, and refined finishes create an atmosphere of warmth and sophistication. Generous formal and casual living areas accommodate every lifestyle. Spanning four impressive levels of living space, the home offers remarkable flexibility with ample room for work, recreation, guests, or a private retreat. Expansive windows frame picturesque views of the lush property, seamlessly blending indoor comfort with outdoor beauty. Located in one of Wellesley’s most desirable neighborhoods, this exceptional estate presents a rare opportunity to enjoy gracious living, classic charm, and an extraordinary setting just minutes from town, commuter rail, and top-rated schools.

25 Hillside Rd, Wellesley

Listing courtesy of Listing Agent: The Lara & Chelsea Collaborative from Listing Office: Coldwell Banker Realty - Wellesley.
21 Cunningham Road, Wellesley
$2,280,000
4 Beds ⋅ 3 Baths ⋅ 73493643 MLS
Charm blends effortlessly with modern style at this classic gem. Rich wood trim, light floors, and thoughtful custom details define the quality here. The dramatic family room—with its soaring ceilings, elegant built-ins, and expansive windows—serve as an impressive gathering place. There is also a stunning dining/breakfast room that offers flexible space. Stone counters and stainless appliances lend to the beauty of the eat-in kitchen. The formal living room is anchored by a fireplace and the at-home-office is the perfect spot to work from home. Upstairs, the primary suite is a true retreat: a private sitting room, walk-in closet, and a spa-inspired bath. Three additional bedrooms and a well-appointed bath accommodate family or guests with ease. A magazine worthy playroom in the lower level. Outdoor entertaining is easy with the expansive blue stone patio and sitting area. The property is set on a cul-de-sac with walking trails. Fabulous commuting location and near shops and the train.

21 Cunningham Road, Wellesley

Listing courtesy of Listing Agent: Teri Adler from Listing Office: MGS Group Real Estate LTD - Wellesley.
50 Upson Rd, Wellesley
$2,280,000
4 Beds ⋅ 4 Baths ⋅ 73429146 MLS
Nestled in Wellesley’s most upbeat neighborhood, this architect built residence offers elegant lifestyle within a vibrant community. Upon entry the flow of natural light, flawless floor plan, & master craftsmanship provides a seamless blend of comfort & practicality. 1st floor incl. a spacious living room w/ box beam ceilings, holiday sized formal dining room, stunning gourmet eat-in kitchen w/ large granite island, fine white cabinetry, pantry & top tier appliances. The family great room w/ gas fireplace and massive windows connects to a serene outdoor patio. A 1st floor office & associated 1/2 bath offers flex options for usage. Upstairs encounter a stunning primary ensuite w/ dual walk in closets & all marble bath w/ luxurious soaking tub & oversized walk in shower plus 3 more sizable bedrooms w/ 2 full baths + laundry room on this level. Large well engineered basement w/ high ceilings provides significant storage & expansion options. Meticulous landscaping and lush grounds. Turnkey

50 Upson Rd, Wellesley

Listing courtesy of Listing Agent: The Shulkin Wilk Group from Listing Office: Compass.
319 Oakland St, Wellesley
$2,270,000
5 Beds ⋅ 5 Baths ⋅ 73541195 MLS
They don't build them like this anymore! Wraparound porch, two staircases, tons of custom millwork, and period details woven into every room. Originally built in 1900, this home was expertly renovated and seriously expanded in 2002. The new kitchen is a showstopper with a beautiful eat-in area flowing into a step-down family room. Then you find the yard. Big, open, and private in a way that feels like a secret this close to town. Formal dining room, sitting room, crafted woodwork throughout, office around the corner. Upstairs the primary suite delivers. Soaring ceilings, bespoke detailing, a bath that holds its own. Four more bright bedrooms, marble counters in every bathroom, laundry up here too. Third floor is a fantastic bonus space for play or work. Finished basement rec room has its own kitchenette, bath, serious storage, and another laundry setup. Great location for easy commutes AND enjoyment of natural spaces with the abutting aquaduct trail, Longfellow Pond and Centennial Park

319 Oakland St, Wellesley

Listing courtesy of Listing Agent: Kathleen Hughto from Listing Office: Rutledge Properties.
12 Leighton Rd, Wellesley
$2,250,000
8 Beds ⋅ 4 Baths ⋅ 73494576 MLS
Proudly presenting this breathtaking fourteen-room home, where timeless elegance meets exceptional opportunity in one of Wellesley’s most desirable Dana Hall neighborhoods. W/ its charming curb appeal, this home exudes history, grace, & character—evoking memories of a bygone era. Rich in original details, leaded glass windows, inviting front & back porches, fire-placed living rooms, soaring ceilings, cherry floors, built-ins & exquisite moldings. Currently configured as a two-family w/ a proven rental history, this home is ideal for investors, multi-generational living, or those looking to convert back to a grand single-family residence or luxury condos. The detached garage offers potential for an ADU, guest cottage, studio, or additional income. Ready for your personal touches, this home enjoys an in-town location steps from the Brook Path, dining, shops, & commuter rail. A rare chance to own a distinctive asset in one of Wellesley’s most sought-after neighborhoods!

12 Leighton Rd, Wellesley

Listing courtesy of Listing Agent: Petrone-Hunter Realty Group from Listing Office: Coldwell Banker Realty - Wellesley.
13 Cavanaugh Rd, Wellesley
$2,250,000
4 Beds ⋅ 3 Baths ⋅ 73446579 MLS
A true gem in one of Wellesley’s most coveted neighborhoods, this beautiful, impeccably maintained four-bedroom, 2.5-bath home blends timeless character w/ modern elegance. A stunning 2013 two-story renovation & addition offers a spacious, sun-filled family room & private primary suite featuring vaulted ceilings, gas fireplace, walk-in closet, & luxurious spa bath w/ soaking tub & large shower. The open floor plan boasts a gourmet kitchen w/ custom white cabinetry, expansive center island, breakfast bar, stainless appliances, gas range, beverage fridge & abundant counter space, flowing seamlessly into the family room & out to large patio & lush yard. Other highlights include central a/c, gleaming hardwood floors throughout, mudroom, 2nd floor laundry & detached garage. Enjoy life in a vibrant, welcoming neighborhood w/ block parties & strong sense of community, just steps from Bates Elementary School. Be home for the holidays - call today!

13 Cavanaugh Rd, Wellesley

Listing courtesy of Listing Agent: Petrone-Hunter Realty Group from Listing Office: Coldwell Banker Realty - Wellesley.
279 Oakland Street, Wellesley
$2,230,000
5 Beds ⋅ 4 Baths ⋅ 73509829 MLS
Timeless Garrison nestled on a picturesque half-acre lot. Extensively renovated and expanded in 2005, this beautifully updated 4,000+ sq ft home blends classic New England charm with modern luxury just steps to Longfellow Pond. Thoughtfully designed with exceptional space & inviting gathering areas, the chef’s kitchen with oversized island opens to a fireside sitting area, the expansive family room flows seamlessly to an elegant fireplaced living room with French doors leading to a private stone patio. Upstairs, the serene primary suite features a walk-in closet and double vanity, along with three additional bedrooms & dedicated home office. The finished lower level offers a recreation room, full bath, & oversized laundry. Meticulously maintained with major system updates, including newer furnaces, central air, & hot water heater. Close to Needham & Wellesley MBTA, this exceptional home offers a rare blend of lifestyle, location, and design. Fiske Elementary is a Blue Ribbon school

279 Oakland Street, Wellesley

Listing courtesy of Listing Agent: Christine Norcross & Partners from Listing Office: William Raveis R.E. & Home Services.
120 Forest St, Wellesley
$2,225,000
5 Beds ⋅ 4 Baths ⋅ 73494133 MLS
Enjoy phenomenal walkability with a 0.6-mile stroll to Wellesley High School, Brook Path and easy access to shops, dining, and commuter rail, all from this 5-bedroom, 4-bath home in the sought-after Country Club neighborhood. Blending timeless charm with modern comfort, wainscoting, arched doorway, and original moldings create a warm, inviting feel. The formal living room features a cozy wood-burning fireplace, while the impressive 20x18 family room offers a coffered ceiling, built-ins, and a wet bar with beverage refrigerator—perfect for entertaining! Thoughtfully updated--granite counter tops, Wolf gas stove, refrigerator (2022), washer/dryer (2022) and meticulously maintained, this home includes elegant living and dining spaces plus a sunken, sun-drenched corner office. Designed for today’s lifestyle with room to relax and recharge. Set on nearly a half-acre, the flat backyard is ideal for play or pets,complemented by a bluestone patio for outdoor dining. A truly move-in ready home.

120 Forest St, Wellesley

Listing courtesy of Listing Agent: Jackie Potdevin from Listing Office: William Raveis R.E. & Home Services.
11 Sterling Rd, Wellesley
$2,200,000
5 Beds ⋅ 4 Baths ⋅ 73506000 MLS
Set in Wellesley’s sought after Dana Hall neighborhood, 11 Sterling Road blends timeless charm with modern living on .57 acres of private, beautifully landscaped grounds. This 5-bedroom home offers 3 full baths and 1 half bath, with an open floor plan tailored for today’s lifestyle. Sun-filled interiors feature a fireplace living room, formal dining room with large picture windows, and a welcoming den/family room with its own fireplace-ideal for both everyday living and entertaining. The kitchen, equipped with stainless steel appliances, flows seamlessly into the main living areas. The second floor includes a spacious primary suite with full bath and three additional bedrooms and another full bath, while the third floor provides a private ensuite fifth bedroom—perfect for guests or a home office. A finished lower level adds versatile space for recreation, fitness, or work. Ideally located near town, schools, and commuting routes. Don't miss this opportunity to make this home your own!

11 Sterling Rd, Wellesley

Listing courtesy of Listing Agent: Debi Benoit from Listing Office: William Raveis R.E. & Home Services.
2 Cavanagh Rd, Wellesley
$2,175,000
3 Beds ⋅ 3 Baths ⋅ 73488484 MLS
On an oversized corner lot, on one of Wellesley’s most beloved streets, this updated classic Colonial embodies timeless style while providing abundant space. Experience an ideal neighborhood setting where you'll enjoy block parties, evening strolls & easy access to the elementary school nearby. A sought-after open layout has spacious kitchen & family room with eat-in area overlooking the large, level, fenced yard & beautiful grounds. Formal dining room is perfect gathering place.The front-to-back living room provides elegant entertaining space plus the sunroom offers serene and flexible retreat for work/play. A brand-new mudroom adds exceptional storage and stylish organization. Upstairs are three well-appointed bedrooms, incl. primary suite. The finished lower level adds valuable living space with 2nd family room plus add'l room for crafts, office, or hobbies. Complete with hard-to-find 2-car garage, 2 Cavanagh Road combines charm, functionality, and an exceptional location!

2 Cavanagh Rd, Wellesley

Listing courtesy of Listing Agent: Molly Campbell Palmer from Listing Office: Gibson Sotheby's International Realty.
5 Tennyson Rd, Wellesley
$2,150,000
5 Beds ⋅ 4 Baths ⋅ 73481579 MLS
Set on a tree-lined street in everyone’s favorite Poet’s Corner neighborhood, this 1930s Colonial blends timeless character with modern comfort. A handsome slate roof and welcoming façade set the tone for the gracious interiors within. The home offers five bedrooms and three-and-a-half baths, including a serene primary suite with ensuite bath. The floor plan features front and back staircases, central air, and a finished third floor with two generously sized bedrooms and an updated bath—ideal for guests, teens, or a home office. Outside, enjoy a charming brick patio, fenced yard, and easy access to Warren Park, major routes, and Boston.

5 Tennyson Rd, Wellesley

Listing courtesy of Listing Agent: Betsy Kessler from Listing Office: Rutledge Properties.
21 Madison Rd, Wellesley
$2,130,000
4 Beds ⋅ 4 Baths ⋅ 73529338 MLS
Beautifully renovated and thoughtfully updated, this stunning four-bedroom home offers the perfect blend of timeless charm and modern comfort. Nestled on a picturesque setting the property enjoys exceptional privacy, peaceful views, and a true connection to nature. Sun-filled interiors feature spacious living areas, refined finishes, and an inviting floor plan designed for both everyday living and effortless entertaining. The renovated kitchen opens seamlessly to warm and welcoming family spaces, while oversized windows bring the outdoors in at every turn. Generously sized bedrooms, updated baths, and flexible living areas provide comfort and versatility for today’s lifestyle. Outside, expansive outdoor spaces create the ideal backdrop for relaxing, dining, or enjoying the tranquil natural surroundings. Rarely does a home combine such beautiful renovations with an idyllic setting, all while remaining close to top schools, commuting routes & all Wellesley has to offer.

21 Madison Rd, Wellesley

Listing courtesy of Listing Agent: The Lara & Chelsea Collaborative from Listing Office: Coldwell Banker Realty - Wellesley.
8 Wilson St, Wellesley
$2,108,000
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.

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