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$1,699,000
5 Beds ⋅ 4 Baths ⋅ 73500976 MLS
Located in the Dana Hall neighborhood of Wellesley, this expansive 5-bedroom, 4-bath home offers a highly desirable and flexible layout, complemented by a detached guest suite, ideal for extended family, an au pair, or visiting guests. The beautifully updated kitchen features ample storage, quality finishes, and seamless flow to sun-filled living spaces, creating an inviting setting for everyday living and casual gatherings. Generously sized bedrooms and a clean, well-lit basement round out the interior. A sparkling pool anchors warm-weather entertaining, while the expansive deck overlooking the large, flat, fenced-in yard provides generous space for grilling, dining, lounging, and hosting. Mature landscaping enhances privacy and curb appeal, and the location offers close proximity to top-rated schools, shops, commuter routes, and recreation. 29 Cottage Street delivers the complete package—flexible living, beautiful indoor-outdoor spaces, and a layout that supports every stage of life.

29 Cottage St, Wellesley

Listing courtesy of Listing Agent: James Gulden from Listing Office: Redfin Corp..
$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.
$2,200,000
3 Beds ⋅ 2 Baths ⋅ 73494065 MLS
Fabulous opportunity to build your dream home or renovate the existing home in the coveted Bates neighborhood. This expansive 40,000 square foot lot is steps to the elementary school, Boulder Brook conservation land, hiking trails & tennis courts. Buyer & buyers agent to do their own due diligence.

53 Elmwood Rd, Wellesley

Listing courtesy of Listing Agent: The Lara & Chelsea Collaborative from Listing Office: Coldwell Banker Realty - Wellesley.
$3,245,000
5 Beds ⋅ 5 Baths ⋅ 73472096 MLS
Incredible new construction opportunity in one of Wellesley’s most sought-after neighborhoods, ideally located within walking distance to the newly built John D. Hardy Elementary School and nearby Perrin Park. This exceptional home offers a fabulous floor plan featuring soaring ceilings, exquisite millwork, abundant natural light, and designer fixtures and finishes throughout. The first floor showcases a grand foyer, open-concept chef’s kitchen with breakfast area, fire-placed family room, formal dining room, and a versatile first-floor study or bedroom. The second level includes four beautifully appointed bedrooms, highlighted by a spacious primary suite, one en-suite bedroom, and a shared double vanity bathroom. The finished lower level provides flexible space for a gym, additional bedroom, and family room. A two-car garage with high ceilings, mudroom, stunning stone patio, and level backyard complete this remarkable property.

38 Parker Rd, Wellesley

Listing courtesy of Listing Agent: William Natoli from Listing Office: Serhant.
$3,695,000
6 Beds ⋅ 5 Baths ⋅ 73469127 MLS
Located in the Country Club neighborhood on 1.15 acres, overlooking Wellesley Country Club greens, with sweeping scenic golf course views. Renovated in 2022, this home blends historic character with refined luxury, featuring wide pine floors, 6 fireplaces, and walls of windows overlooking the greens. Gracious living spaces include an inviting fire-placed great room, sophisticated library, dining room, home office with separate entrance w/full bath (or 6th bedroom). Primary suite with vaulted ceilings and radiant bathroom, 4 additional bedrooms (two ensuite), 4th bedroom access to third-floor game room. The finished lower level features a large billiards/family room, gym, workshop, mudroom & storage. Bluestone patio and wraparound deck capture panoramic views, spectacular sunrises and sunsets, fruit trees and a 19th-century unfinished barn with electricity and water & a fenced in paddock. Abutts conservation land, 2 car garage, cobblestone parking, stoned walls, can be sold furnished.

151 Oakland Street, Wellesley

Listing courtesy of Listing Agent: Beth Dickerson from Listing Office: Gibson Sotheby's International Realty.
$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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