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$4,999,000
6 Beds 8 Baths 73555707 MLS
Nature Lovers Paradise on the Charles River! Stunning in every season, each element of this spectacular property is crafted to maximize your enjoyment and access to the great outdoors. Reimagined by renowned architect Patrick Ahern, the exterior boasts a flat grassy backyard and stone patios with unobstructed views. Inside, a gracious and flexible floor plan is filled with light and views from myriad windows, French doors, and private balconies. First floor living with exquisite primary bedroom suite, a great room, expansive living room, dining and updated kitchen w/ light-filled breakfast room, an add’l bedroom suite and choice of offices complete the main floor. Upstairs, 4 more ensuite bedrooms, including a 2nd primary suite option. Large walk-out finished LL w/ bar, gym & media room. 3 car garage and flat courtyard driveway off protected cul de sac within minutes of extensive Wellesley Trails and Town Center. A notch above the rest. Bring your hiking shoes, kayaks, lounge chairs and lawn games!

12 Winding River Cir, Wellesley

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

$3,800,000
5 Beds 6 Baths 73555589 MLS
Recently renovated expansive Cape with over 6200 sq ft of living space on three floors. Beautifully landscaped ½ acre lot in the very desirable and prestigious Peirce Estates. Generously proportioned living, dining, and family rooms, first floor Library/Office, updated eat in kitchen, renovated marble baths and optional first floor main suite. Total 5 Bedrooms, 3 full and 3 half baths. Crystal chandeliers throughout the house. Fully finished basement with checkered Italian marble floors in the front room. Fenced back yard with a deck and a stone fire pit. Attached two car garage. Bates elementary school. Meticulously maintained this home is perfect for peaceful living or entertaining friends.

23 Bellevue, Wellesley

Listing courtesy of Listing Agent: Ritu Chawla from Listing Office: Coldwell Banker Realty - Wellesley.

$2,865,000
5 Beds 6 Baths 73552915 MLS
Exceptional opportunity to own 5,100+ sq. ft. of luxury 2024 construction offering outstanding value in one of Wellesley's most convenient in-town locations. Just steps to Hardy Elementary, Morse's Pond, Fells Library, Wellesley Center & commuter rail. Thoughtfully designed for modern living, this sun-filled home features soaring ceilings, exceptional craftsmanship & four finished levels. Stunning chef's kitchen w/ oversized island & premium appliances flows seamlessly into dramatic family room—ideal for everyday living & entertaining. Elegant dining room, thoughtfully designed mudroom & private bedroom suites on the 2nd, 3rd & lower levels provide exceptional flexibility for guests, au pair, home office or multigenerational living. Gorgeous primary bedroom suite w/ lavish bath. Expansive lower level offers endless possibilities for recreation, fitness or media. A rare opportunity to enjoy the quality, space & convenience of nearly new construction.

265 Weston Rd, Wellesley

Listing courtesy of Listing Agent: Petrone-Hunter Realty Group from Listing Office: Coldwell Banker Realty - Wellesley.

$6,350,000
6 Beds 7 Baths 73547652 MLS
Set within Wellesley’s distinguished Cliff Estates, this contemporary residence, completed in 2025, blends scale, refined design, and modern luxury across three finished levels. A grand foyer with floating stair and walls of windows introduces light-filled interiors with generous ceiling heights. Formal living and dining rooms, supported by a Butler’s station, elevate entertaining. The kitchen anchors daily life with an oversized island, premium appliances, and a separate pantry with patio access. A family room, private office, and first-floor en-suite complete the main level. Upstairs, the primary retreat offers a spa-inspired bath and custom walk-in closet, set apart from a lounge and three en-suite bedrooms. The walkout lower level extends the living space with recreation, media, gym, and an en-suite guest room. Two bluestone patios and a landscaped yard bordered by a mature tree line create a private outdoor setting near shops, dining, trails, and Wellesley Country Club.

9 Bellevue Road, Wellesley

Listing courtesy of Listing Agent: Nekky Parkiotis from Listing Office: Real Broker MA, LLC.

$5,995,000
6 Beds 6 Baths 73545332 MLS
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

Listing courtesy of Listing Agent: Melissa Dailey from Listing Office: Coldwell Banker Realty - Wellesley.

$14,000
5 Beds 6 Baths 73543787 MLS
Completely reimagined, this exceptional 5,700+ sq ft residence is ideally situated on a quiet residential loop just steps from top-ranked Wellesley schools, Linden Square, commuter rail, Whole Foods, and parks. Designed for modern living, the home features sun-filled open-concept spaces, seamless indoor-outdoor flow, and beautifully connected kitchen, wet bar, and family room overlooking a level backyard surrounded by mature trees with a private feel that's rare this close to town. The impressive primary suite offers soaring ceilings, a private terrace, dual walk-in closets, and a spa-inspired bath, while generously scaled bedroom suites provide exceptional flexibility for work, study, and relaxation. A spectacular lower level with kitchenette, theater, lounge, fitness, and recreation areas creates the ideal setting for entertaining and everyday living. Turnkey throughout, this is a rare opportunity to enjoy walkable in-town living without sacrificing space, privacy, or modern comfort.

31 Alba Rd, Wellesley

Listing courtesy of Listing Agent: Zhichao Chen from Listing Office: Space Realty.

$5,350,000
5 Beds 7 Baths 73540738 MLS
Nestled in the heart of Wellesley’s coveted Cliff Estates, this exquisite custom-built residence by a highly regarded builder blends timeless elegance w exceptional craftsmanship. Built in 2013, the home welcomes you w a sun-drenched two-story foyer, formal fireplaced livingroom, sophisticated dining room and a private first-floor office. The expansive family room flows seamlessly into the chef’s kitchen featuring premium finishes and a spacious dining area ideal for everyday living and entertaining. The second level offers a luxurious primary suite w a spa-inspired bath and exceptional walk-in closet, along w four additional bedrooms and conveniently located laundry room. The finished lower level features an entertainment lounge, media room, wet bar, wine cellar, and home gym. Outside, impeccably manicured grounds and a stunning stone waterfall create a private outdoor retreat. Just moments from Wellesley’s top schools, shops, restaurants, and commuter routes. An elegant masterpiece!

14 Bristol Road, Wellesley

Listing courtesy of Listing Agent: The Sarkis Team from Listing Office: Douglas Elliman Real Estate - The Sarkis Team.

$4,395,000
6 Beds 7 Baths 73540282 MLS
Set on one of Wellesley Farms’ most coveted and sought-after streets, this exceptional Colonial offers four levels of elegant living in one of Wellesley’s premier neighborhoods. Beautifully built and thoughtfully designed, the home features generously scaled rooms ideal for both comfortable everyday living and sophisticated entertaining. Sun-filled interiors showcase refined millwork, custom built-ins, rich architectural detail, and timeless craftsmanship throughout. The chef’s kitchen opens seamlessly to a welcoming family room with a fieldstone fireplace and French doors leading to a terrace overlooking private, professionally landscaped grounds. The second floor features a luxurious primary suite plus four additional bedrooms and three full bathrooms. The third level offers an en suite bedroom, ideal for guests, au pair, or home office use. The finished lower level includes a spacious recreation room and exercise room with sauna and full bath. An exceptional Wellesley residence.

8 Valley Road, Wellesley

Listing courtesy of Listing Agent: Dean Poritzky from Listing Office: Engel & Volkers Wellesley.

$10,995,000
5 Beds 6 Baths 73540092 MLS
Not all new construction is created equal. The result of a visionary collaboration between acclaimed architecture firm Of Possible and renowned custom builder NS Builders, 45 White Oak Rd represents a rare opportunity to own a residence where design, craftsmanship, and performance were never compromised. Conceived as a showcase of what is possible when architecture and construction are executed at the highest level, this 7,200+ sq. ft. home balances architectural significance with the warmth and functionality required for everyday living. Expansive walls of glass create a seamless connection to the beautifully landscaped grounds, while custom German white oak millwork, curated natural stone finishes, and exceptional detailing reflect an uncompromising commitment to quality throughout. Designed for both grand entertaining and comfortable daily living, the home offers a level of craftsmanship, sophistication, and performance rarely found in today's market.

45 White Oak Rd, Wellesley

Listing courtesy of Listing Agent: The Sarkis Team from Listing Office: Douglas Elliman Real Estate - The Sarkis Team.

$3,398,500
6 Beds 6 Baths 73539779 MLS
Incredible opportunity to own this exceptional new construction home in one of Wellesley’s most sought-after neighborhoods. Crafted by a respected local builder, this home showcases quality craftsmanship and thoughtful design throughout. The sun-filled first floor features a private office or guest room with full bath, elegant dining room, cozy den, and a stunning chef’s kitchen designed for everyday living and entertaining. Upstairs, vaulted ceilings create an airy feel, highlighted by a luxurious primary suite with a spa-inspired bath, steam shower, and marble flooring. Three additional bedrooms, two full baths, and a convenient laundry room complete the second level. The finished lower level offers outstanding flexible living space, including a spacious family room, guest bedroom, full bath, and gym. Enjoy outdoor living on the covered patio overlooking the beautiful yard. Ideally located just minutes to Hardy School, shopping, dining, and major commuting routes!

28 Parker Rd, Wellesley

Listing courtesy of Listing Agent: Gabby Cefalo from Listing Office: Coldwell Banker Realty - Wellesley.

$6,665,000
6 Beds 8 Baths 73537708 MLS
Exceptional new construction with a fresh take on transitional luxury, blending incredible design with warm, livable spaces. Bathed in natural light, this beautifully built home features soaring ceilings, and has layers of impeccable detail. The stunning chef's kitchen serves as the centerpiece of the home, showcasing custom white oak cabinetry, stunning exposed wood beams, top appliances, and an effortless flow into the dining and living areas–perfect for entertaining. The office has a calming palette, ideal for working from home. Retreat to the primary suite, complemented by a spa-inspired marble bathroom. Each additional bath was crafted with high-end materials. The same quality is in the finished lower level playroom and gym. Step outside to a private backyard and covered patio with a fireplace which sets the stage for outdoor living and entertaining. An unparalleled offering in the Dana Hall area of town- close to the Hunnewell School, shops, restaurants and the train!

222 Grove Street, Wellesley

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

$3,195,000
5 Beds 6 Baths 73530659 MLS
Completely reimagined, this exceptional 5,700+ sq ft residence is ideally situated on a quiet residential loop just steps from top-ranked Wellesley schools, Linden Square, commuter rail, Whole Foods, and parks. Designed for modern living, the home features sun-filled open-concept spaces, seamless indoor-outdoor flow, and beautifully connected kitchen, wet bar, and family room overlooking a level backyard surrounded by mature trees with a private feel that's rare this close to town. The impressive primary suite offers soaring ceilings, a private terrace, dual walk-in closets, and a spa-inspired bath, while generously scaled bedroom suites provide exceptional flexibility for work, study, and relaxation. A spectacular lower level with kitchenette, theater, lounge, fitness, and recreation areas creates the ideal setting for entertaining and everyday living. Turnkey throughout, this is a rare opportunity to enjoy walkable in-town living without sacrificing space, privacy, or modern comfort.

31 Alba Rd, Wellesley

Listing courtesy of Listing Agent: Zhichao Chen from Listing Office: Space Realty.

$4,870,000
6 Beds 8 Baths 73524600 MLS
Overlooking the sweeping 18-hole vistas of Wellesley Country Club, this exceptional Colonial estate blends timeless New England elegance with refined modern living. Thoughtfully redesigned over a two-year collaboration with a premier design team, every detail — from the architecture and lighting to the soft blue-gray palette — was carefully curated to complement the surrounding landscape and evoke warmth, balance, and tranquility. The dramatic 20-foot living space creates an unforgettable first impression, where floor-to-ceiling windows frame breathtaking golf course views and ever-changing seasonal scenery. Expansive outdoor living areas extend seamlessly into the natural surroundings, creating an atmosphere that feels both serene and inspiring. Custom finishes, sophisticated interiors, a cathedral-ceiling sunroom, and thoughtfully integrated living spaces bring natural light and landscape views into every corner of the home, offering a sense of beauty, comfort, and calm throughout.

179 Oakland St, Wellesley

Listing courtesy of Listing Agent: Lin Shi from Listing Office: Phoenix Real Estate.

$3,800,000
5 Beds 7 Baths 73514279 MLS
Stunning new construction offering exceptional design and modern living. Entertaining is elevated with this open-concept layout featuring a chef’s kitchen, living room, dining area, and fireplaced family room—seamlessly leading to a private deck with a built-in stone gas grill. No detail is overlooked; the walls boast custom woodwork and high-end finishes throughout. This thoughtfully crafted home features five bedrooms, each with its own en suite bath, including a luxurious second-floor primary suite with a custom walk-in closet. The first-floor bedroom with en suite provides ideal flexibility for guests or a home office. The oversized basement includes a full bath, along with a separate exercise room. Conveniently located near shopping, dining, and all amenities in Needham and Wellesley, with easy access to major commuter routes.

11 Skyline Drive, Wellesley

Listing courtesy of Listing Agent: Christine Norcross & Partners from Listing Office: William Raveis R.E. & Home Services.

$4,295,000
5 Beds 6 Baths 73510191 MLS
Coveted in town/Dana Hall location! Incredible opportunity to live in a beautiful colonial with a complete renovation/addition. Over 5000 sq ft on 4 full floors. Large open floor plan for kitchen family room. Coffered ceilings, built-in banquette and walk-in pantry are just a few design features in this space. Formal living and dining room with private study and large mudroom with built-ins complete the first floor. Main suite with large walk-in closet and vaulted ceiling. 4 additional bedrooms and 3 full baths with laundry room. Oversized 3rd floor perfect for 2nd home office or bonus space. Lower level with room for guests with full bath plus exercise room and large playroom along with great storage. Your opportunity to customize now. Large flat yard! Block party neighborhood just short distance to Brook Path, Wellesley Center, Wellesley College, Nehoiden Golf Course and Hunnewell School.

17 Midland Road, Wellesley

Listing courtesy of Listing Agent: Melissa Dailey from Listing Office: Coldwell Banker Realty - Wellesley.

$5,497,000
5 Beds 7 Baths 73509134 MLS
A rare standard of craftsmanship in Wellesley's coveted Generals neighborhood. This custom Neoclassical Colonial — completed in 2017, 6,300+ SF across four elevator-served levels — was built without compromise: whole-house radiant heat, grain-matched white oak floors, bespoke millwork, and soaring 9-foot ceilings throughout including the lower level. The chef's kitchen anchors the home with soapstone countertops, dual dishwashers, and a walk-in pantry. Five en-suite bedrooms, including a primary suite with spa bath designed for genuine restoration. The lower level delivers a private executive office, home gym, wine storage, and a Bowers & Wilkins Diamond cinema — a complete retreat beneath the main living spaces. Outdoors: custom patio, outdoor fireplace, hot tub, arborvitae-screened privacy, and two EV chargers. Two-car garage. Steps to Morses Pond, Hardy Elementary, Linden Square, and Wellesley Square. Minutes to commuter rail.

48 Marshall Rd, Wellesley

Listing courtesy of Listing Agent: Team Coyle from Listing Office: Compass.

$2,250,000
8 Beds 6 Baths 73503038 MLS
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

Listing courtesy of Listing Agent: Jill Boudreau from Listing Office: eXp Realty LLC - Corporate Office.

$3,500,000
5 Beds 6 Baths 73499362 MLS
Beautiful New Construction in desirable Wellesley Hills near Warren Park. The inviting front porch & enhanced driveway w/cobblestones sets the tone of the home's warmth & craftsmanship. It's 5,800 sq.ft. of living over 4 levels. No detail has been overlooked, from the layout, custom built-ins, coffered ceiling & shiplap accents. The Chef's kitchen has Thermador appliances, large center island and sunny eat-in area that abuts a spacious family room. Flexible first floor w/office or living room & a formal dining room. 5 bedrooms, including a Primary Suite w/walk-in closet & spa-like bath. The expansive lower level has a full bath offering plenty of space for a playroom & gym. The oversized mudroom w/custom built-ins, easy access to the stone patio will not disappoint. A 2 car garage w/overflow parking space, making coming & going a breeze. It's an ideal commuter location near the Hills Train and short distance to shops, restaurants, & Hills Library. Delivery date is mid-June!

144 Washington Street, Wellesley

Listing courtesy of Listing Agent: Patricia Bradley from Listing Office: Rutledge Properties.

$5,695,000
5 Beds 7 Baths 73499334 MLS
Once in a lifetime opportunity to own in Wellesley's most coveted premier historic location, Pond Road. Featuring the finest custom craftsmanship throughout, professionally engineered mechanical systems, smart house and professionally designed ultra high end finishes. Over 9400 sq ft of living space on 3 floors. The floor plan everybody wants with a 1200 sq ft great room and over 10 foot ceilings. Oversized mudroom and pantry. First floor includes white oak herring bone hardwoods. 2nd floor ceilings 14-20 feet! An incredible main suite. All bedrooms en-suite with walk-in closets. Plus a 2nd floor lounge room or incredible guest suite. Lower level is unprecedented with 17 ft ceiling in 1/2 court basketball/ rec room (size of space also work for squash) with viewing room including wet bar. Theatre/media room with additional wet bar plus a gym with full bath including steam shower. Large flat yard. Close to Wellesley trails and town center.

196 Pond Road, Wellesley

Listing courtesy of Listing Agent: Melissa Dailey from Listing Office: Coldwell Banker Realty - Wellesley.

$3,400,000
10 Beds 9 Baths 73445436 MLS
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

Listing courtesy of Listing Agent: Linda Glennon from Listing Office: Conway - Hanover.

$3,795,000
6 Beds 6 Baths 73401549 MLS
New home in Cliff Estates with the ideal floor plan and one of Wellesley's favorite designers creating the perfect interior! Gracious foyer with large kitchen family room off of the back of the home. Oversized kitchen island with fireplace in family room. First floor private study. Living room with another fireplace and dining room both with custom millwork. Mudroom with cubbies and closet. Second floor with excellent main suite with sitting area, large walk -in closet and spa-like bath. 3 additional bedrooms with walk-in closets and 2 full baths. Third floor great space with bedroom and full bath plus a bonus room/office. Lower level with 6th bedroom and 5th full bath. Great playroom with beverage bar and lots of storage! Large flat yard with plenty of room for backyard parties along with a fun bridge in back of property. A must see!

201 Lowell Road, Wellesley

Listing courtesy of Listing Agent: Melissa Dailey from Listing Office: Coldwell Banker Realty - Wellesley.

$5,100,000
7 Beds 7 Baths 73376559 MLS
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

Listing courtesy of Listing Agent: Donahue Maley and Burns Team from Listing Office: Compass.

$2,899,000
6 Beds 6 Baths 73344384 MLS
Welcome home to this spacious and elegant colonial farmhouse nestled on its own private hill in the coveted Cliff Estates. The home perfectly blends the charm and character of an original farmhouse (including 8 original fireplaces) with modern features that suit today's lifestyle, such as multiple options for home office spaces. Five bedrooms (including primary suite) are located on the second floor. Sixth bedroom with full bathroom and bonus room on third floor is perfect for guests or in-laws to have privacy. Main level flows nicely with kitchen, butler's pantry, dining room, family room, office, sunroom, mudroom, laundry and 2 half baths. French doors from the kitchen and family room lead outside to a backyard oasis. A level yard with a lovely patio makes this a perfect place to relax outdoors on over 1/2 acre of private land.

42 Edmunds Road, Wellesley

Listing courtesy of Listing Agent: Rachel Lieberman from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.

$6,950,000
8 Beds 9 Baths 73329026 MLS
Presenting a spectacular multi-acre estate set behind a private entry in Wellesley. This stately Georgian Colonial is the centerpiece of the compound on a scenic road and is surrounded by a parklike setting that couples luxury with sophistication. The stately exterior is captivating with stunning architectural detail. Inside the grand home boasts a two story foyer with a sweeping bridal staircase, soaring ceilings and elegant wood detail. There is a beautiful white kitchen with skylights and adjacent is a sun filled family room. All the formal living areas are spectacular, lending themselves naturally for large scale entertaining. A private apartment offers flexibility along with the ample bedroom and bathroom count on the second level. The pool, cabana with a bathroom and kitchen and tennis court are all accents to the rolling gardens. Included in this offering are two one-acre buildable lots that can be separated or kept as part of the property.

200 Pond Road, Wellesley

Listing courtesy of Listing Agent: Meghan Sutherland from Listing Office: MGS Group Real Estate LTD - Wellesley.

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