Wellesley Hills Real Estate

Welcome to Wellesley Hills, a picturesque gem nestled within the charming town of Wellesley, Massachusetts, in the heart of Norfolk County. Known for its idyllic suburban charm, Wellesley Hills offers a unique blend of serene residential living and vibrant community spirit, making it an ideal place to call home.

Wellesley Hills is characterized by its stunning tree-lined streets, historic homes, and beautifully manicured gardens. The area boasts a rich history, with many properties reflecting classic New England architecture that adds to its quaint appeal. Residents enjoy a strong sense of community, with local events and gatherings fostering connections among neighbors.

Nature enthusiasts will delight in the proximity to parks and recreational areas, including the scenic Wellesley College campus and the lush grounds of the nearby Elm Bank Reservation. These spaces provide ample opportunities for outdoor activities, from leisurely strolls to invigorating hikes. Additionally, the town's commitment to maintaining green spaces ensures that residents can enjoy the beauty of the outdoors right at their doorstep.

Wellesley Hills is also conveniently located near top-rated schools, making it a desirable area for families seeking quality education. With a vibrant downtown area filled with boutique shops, delightful cafes, and gourmet restaurants, residents have access to a rich array of dining and shopping options.

Whether you’re drawn to the community’s rich history, its beautiful natural surroundings, or its welcoming atmosphere, Wellesley Hills offers an exceptional lifestyle that perfectly balances tranquility and convenience. Discover your dream home in this charming enclave today!

Newest Listings in Wellesley Hills

$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.

$5,350,000

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.

$1,925,000

4 Beds ⋅ 3 Baths ⋅ 73533550 MLS

Presenting this extraordinary, beautifully updated 1800s modern farmhouse in highly convenient Wellesley Hills. Privately set on a tucked-away lane w/ minimal traffic yet just a short walk to the train, shops & restaurants, this unique home features high ceilings, lovely appointments & a wonderful sense of connection throughout. A welcoming front porch & foyer open to sun-filled living spaces including a family room off the kitchen perfect for everyday living & entertaining. Dining & living rooms are enhanced by fireplaces & crown moldings. The primary suite offers a serene retreat w/ a stylish newer bath. Three additional bedrooms & second floor laundry. Wonderful, spacious living space above the 2-car garage provides versatility for home office, gym, studio, or possible ADU. Relax on the porches, patio & grounds—a special home that must be experienced in person.

40 Kimlo Rd, Wellesley

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

$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.

$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.

$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.

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