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$3,195,000
6 Beds ⋅ 5 Baths ⋅ 73573834 MLS
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

Listing courtesy of Listing Agent: The Lara & Chelsea Collaborative from Listing Office: Coldwell Banker Realty - Wellesley.
$3,595,000
6 Beds ⋅ 5 Baths ⋅ 73569459 MLS
Exquisite renovation of this distinctive property blends historic architectural character with sophisticated luxury living. Set on picturesque grounds with beautiful views of gardens, patios, the historic barn, golf course, and skyline vistas. Gracious, light-filled interiors feature hardwood floors, fireplaces, architectural detail, and beautiful views throughout. The sunny kitchen opens to a family room with gas fireplace, wet bar, and french doors to patio while the adjoining breakfast room/sunroom opens to a deck with sunrise views. A spacious great room with beamed ceilings and fireplace provides exceptional entertaining space. A first-floor office with separate entrance and full bath offers potential for an in-law/nanny suite. A wood paneled library with built-ins and a well-appointed dining room round out the first floor. Upstairs are five bedrooms, a sitting room/nursery, and four renovated baths. The third floor features a game room. The expansive lower level includes a recreation room, exercise room, workshop, mudroom, storage, and access to the two-car garage. A historic barn with electricity and water adds character and offers potential for an ADU. Convenient to Wellesley Hills shops, restaurants, commuter rail, and major routes, this exceptional property combines privacy, character, style, and remarkable views.

151 Oakland Street, Wellesley

Listing courtesy of Listing Agent: The Wilson Group from Listing Office: Compass.
$16,999
6 Beds ⋅ 5 Baths ⋅ 73561755 MLS
Available on 12/1! Enjoy condo-like living with furniture, ground maintenance and snow removal (over 3") included. This gorgeously built colonial offers 6 bedrooms, and 5 full bathroom with rich architecture and professionally landscaped yard. It conveniently situated minutes away from Sprague Elementary School and Wellesley Middle School, Wellesley downtown, Wellesley Commuter Rail Station, and Linden Square. First floor boasts a large, welcoming foyer that flows into coffered ceiling living and family room with fireplace, gorgeous dining room, one full bath and kitchen with custom island and high-end appliances such as sub-zero refrigerator. Second floor offers five spacious bedrooms and three full baths including master suite with two walk-in closets. Finished lower level features playroom, office, walk-out media room to bluestone patio, and one full bath. Furniture included in the rent but may be varied from shown in photos. Pets considered with restrictions.

28 Maurice Rd Unit 28, Wellesley

Listing courtesy of Listing Agent: HyRoad Partners Team from Listing Office: HyRoad Realty, LLC.
$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.
$34,000
6 Beds ⋅ 5 Baths ⋅ 73550778 MLS
Welcome to this exquisitely restored Victorian, where historic charm and contemporary sophistication come together in one of Wellesley's most desirable neighborhoods. Thoughtfully renovated, this exceptional residence offers luxurious living with designer finishes, custom craftsmanship, and an inviting floor plan designed for today's lifestyle. Designed with comfort and flexibility in mind, the home offers spacious bedrooms, multiple living and gathering areas, dedicated workspaces, and modern conveniences including high-speed internet, zoned heating and cooling, heated floors, and Smart TVs, The beautifully landscaped grounds feature a welcoming farmer's porch, expansive outdoor living and dining spaces, and a cozy fire pit—ideal for relaxing evenings, outdoor living, or enjoying New England's changing seasons. Rented furnished only!

28 Longfellow, Wellesley

Listing courtesy of Listing Agent: Kristen DiBella from Listing Office: Boom Realty.
$4,995,000
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.
$3,299,000
6 Beds ⋅ 5 Baths ⋅ 73542007 MLS
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

Listing courtesy of Listing Agent: Elisabeth Preis from Listing Office: Compass.
$5,800,000
7 Beds ⋅ 9 Baths ⋅ 73536264 MLS
Set on a beautifully flat lot in one of Wellesley’s most desirable neighborhoods, this exceptional Colonial offers a rare combination of luxury, space, and timeless design. Located in a special community with a picturesque meadow at its center, providing a peaceful setting. Featuring 7 bedrooms, 7 full and 2 half bathrooms, this thoughtfully designed home offers flexibility for today’s lifestyle. The stunning chef’s kitchen features a center island, top-of-the-line appliances, custom cabinetry, and separate walk-in pantry. Spacious living areas, elegant formal rooms, high ceilings, natural light, and beautiful finishes create an inviting atmosphere. The luxurious primary suite offers a private retreat, while the generous secondary bedrooms provide comfort for family and guests. Multiple spaces allow for work, recreation, and entertaining. The expansive backyard is ideal for outdoor enjoyment, conveniently located near Wellesley’s top-rated schools, town center, train, and major routes.

45 Longmeadow Rd, Wellesley

Listing courtesy of Listing Agent: Lisa Sewall from Listing Office: Coldwell Banker Realty - Wellesley.
$2,250,000
8 Beds ⋅ 5 Baths ⋅ 73503039 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.
$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.
$3,400,000
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.
$4,895,000
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.
$6,250,000
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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