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$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.
$1,348,000
3 Beds ⋅ 2 Baths ⋅ 73522956 MLS
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, and the property is served by a 4-bedroom septic system, 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

Listing courtesy of Listing Agent: Christine Norcross & Partners from Listing Office: William Raveis R.E. & Home Services.
$2,150,000
5 Beds ⋅ 3 Baths ⋅ 73522184 MLS
Gracious Victorian w/an incredible Barn & workshop, a distinctive property zoned GR offering unmatched versatility. The inviting front porch sets the tone of warmth & charm of this beautifully renovated home brimming w/vintage details such as stain glass windows, turned staircase & 9' ceilings. Gorgeous chef's kitchen w/white shaker cabinetry, 2 copper sinks, high-end appliances, quartz & large center island for gathering. The expansive family & living rm w/cozy fireplace offers plenty of space for entertaining. 2nd floor has a home office and 3 bedrooms including a luxurious spa-like bath. The 3rd floor has a generous 4th bedroom or bonus room. Enjoy summer BBQs on the stone patio. There a garage plus extraordinary barn w/a heated workshop & room enough for 6 cars. Income option w/the apartment at ground level w/a separate entrance & patio. Own a part of Wellesley's history. Conveniently located near the train, town center, schools, restaurants & more, all the best of Wellesley!

33 Linden Street, Wellesley

Listing courtesy of Listing Agent: Patricia Bradley from Listing Office: Rutledge Properties.
$1,799,000
4 Beds ⋅ 3 Baths ⋅ 73519258 MLS
Home. Location. Land. Four bedroom colonial on a half acre lot with a short distance to town, train and Hunnewell School! Kitchen opens to an oversized family room with fireplace and bar area for entertaining. Kitchen with stainless appliances and breakfast bar plus room for dining table with access to deck. Front to back living room with 2nd fireplace. Formal dining room with built-ins for showcasing dishware. Stunning sunroom with cathedral ceilings and three sides of windows perfect for office space or relaxing. Oversized main bedroom with en-suite bath with double vanities plus multiple large closets. Private balcony. All three additional bedrooms similar in size with full bath. Huge walk out lower level with 2 finished rooms and great storage or future expansion. 2 car garage. Storage shed and patio is part of this incredible fully fenced in yard! Wonderful urban suburban location.

98 Brook Street, Wellesley

Listing courtesy of Listing Agent: Melissa Dailey from Listing Office: Coldwell Banker Realty - Wellesley.
$3,195,000
5 Beds ⋅ 5 Baths ⋅ 73518756 MLS
Crafted in 2022 by one of Wellesley's most coveted builders, this stunning 5-bedroom Colonial sits in one of Wellesley's most sought-after pockets, east of Weston and north of Route 9, quiet and tucked away yet minutes to highway access, close to top schools, playgrounds, and nature walks. Thoughtfully designed living space boasts exquisite finishings throughout. The chef's kitchen with gas cooking, pantry, and second sink flows into a fire-placed family room. A formal living room, first-floor study, and custom built-ins round out the main level. Upstairs, the primary suite stuns with a spa bath, steam shower, radiant heated floors, and a custom walk-in closet. Additional bedrooms feature generous storage and second-floor laundry adds convenience. The finished lower level offers a home gym, kitchenette, rec room, and private fifth bedroom with full bath. A stone patio and level yard invite al fresco living. Radiant-heated mudroom, two-car garage, and EV charging complete this home.

7 Massasoit Road, Wellesley

Listing courtesy of Listing Agent: Donna Scott Group from Listing Office: Coldwell Banker Realty - Wellesley.
$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.
$3,150,000
4 Beds ⋅ 5 Baths ⋅ 73513990 MLS
Exceptional 2016 construction in one of Wellesley’s most sought-after neighborhoods near town, top-rated schools, scenic trails, and Morses Pond. Built by a premier local builder known for superior craftsmanship and elevated building standards, this sun-filled 4-bedroom home offers thoughtful open design and custom details throughout. Elegant living room with tray ceiling and bay window, spacious dining room with paneled wainscoting, and chef’s kitchen with custom cabinetry, granite countertops, high-end stainless steel appliances, and oversized island opening to a family room with stone-faced gas fireplace, built-ins, and private covered porch and patio. Luxurious primary suite with spa-like bathroom, radiant heated floors, and oversized shower. Second ensuite bedroom. Finished lower level with full bath and oversized windows plus finished third floor ideal for office, gym, or playroom. Flexible living space in a prime Wellesley location.

35 Marshall Rd, Wellesley

Listing courtesy of Listing Agent: Cook Real Estate Partners from Listing Office: Keller Williams Elite.
$1,160,000
4 Beds ⋅ 2 Baths ⋅ 73511385 MLS
Top condition 4 bed room, single family, 1.5 bath on the corner of a cul-de- sac. Great location with easy access to Routes 9, 16 & 30. Updated kitchen and baths. Insulated windows Finished basement with large laundry/storage room.

2 Marigold Ave, Wellesley

Listing courtesy of Listing Agent: William Gath from Listing Office: Realty Executives Boston West.
$1,799,999
5 Beds ⋅ 4 Baths ⋅ 73510295 MLS
Welcome to Wellesley Farms!! Situated in a highly sought-after neighborhood, this beautifully renovated, energy-efficient home is set back from the street and enhanced with new windows and system upgrades.The sun-filled kitchen with cathedral ceilings flows into the family and dining rooms, perfect for both everyday living and entertaining. A stunning great room features custom built-ins and a wood-burning fireplace. Additionally, the floor plan offers the flexibility for a private guest bedroom or home office. A luxurious primary suite on the second floor, complete with a dual-head shower, freestanding soaking tub, and walk-in closet.The finished lower level offers a custom mudroom as you enter from the 2 car garage, and endless possibilities for a game room or home gym with a full bath.Close to Warren Park, Reidy Field, Sprague Elementary and restaurants/shops makes this Wellesley location so special. Seller can accommodate a quick closing.

7 Garden Rd, Wellesley

Listing courtesy of Listing Agent: Timothy E. Driscoll from Listing Office: South Shore Sotheby's International Realty.
$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.
$2,885,000
5 Beds ⋅ 4 Baths ⋅ 73507050 MLS
Located on one of Wellesley’s most coveted roads in Cliff Estates, 100 Albion is a beautifully appointed pillared white Colonial set on .77 acres of professionally landscaped grounds. Blending timeless architecture with modern living, the main level offers a gracious fireplaced living room with a large picture window, an elegant dining room, a private office, and an expansive kitchen centered around a large island. These spaces flow seamlessly into a spacious fireplaced family room with custom cabinetry and out to a brand-new deck ideal for indoor/outdoor entertaining. The first floor also includes a well-placed laundry room with a full bath. Upstairs are five bedrooms, including a serene primary suite with a walk-in closet, along with four additional bedrooms and two full baths. The finished walk-out lower level features a full bath and bar, providing versatile living space. Exceptional curb appeal, a circular driveway, and beautifully landscaped grounds complete this impressive home.

100 Albion Rd, Wellesley

Listing courtesy of Listing Agent: Debi Benoit from Listing Office: William Raveis R.E. & Home Services.
$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.
$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.
$1,595,000
3 Beds ⋅ 3 Baths ⋅ 73499017 MLS
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

Listing courtesy of Listing Agent: Amy Jacobson from Listing Office: William Raveis R.E. & Home Services.
$1,100,000
3 Beds ⋅ 3 Baths ⋅ 73497359 MLS
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

Listing courtesy of Listing Agent: Frank Celeste from Listing Office: Gibson Sotheby's International Realty.
$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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