5-Bedroom Homes for Sale in Chestnut Hill

Nestled on a beautiful tree-lined street in Olde Chestnut Hill, this spectacular home offers an open and elegant floor-plan perfect for living and entertaining. Thoughtfully renovated in 2012, this home masterfully blends timeless architectural charm with modern amenities. High ceilings, abundant natural light, and beautifully crafted moldings and millwork create a sense of warmth throughout.The

Taylor Blacker Luxury Residential Group, LLC

Tucked away at the end of a quiet dead-end street, 120 Cabot Street is a breathtaking French chateau-style residence that transports you to Europe while offering the best of Boston luxury. With soaring 11-foot ceilings and exquisite architectural details, this home exudes elegance, from its gracious living and dining rooms with floor-to-ceiling French doors to its gourmet kitchen, complete with a

George Sarkis Douglas Elliman Real Estate - The Sarkis Team

Welcome to 130 Cabot Street— a distinguished estate on a generous corner lot in Chestnut Hill. This exceptional property boasts 6 bedrooms, 7 bathrooms, private entry guest suite, private office, home gym, 3 car garage, wine cellar, and a finished walkout lower-level media room. Additional features include high ceilings, 3 fireplaces, and a 1st floor primary suite with walk-in closets. The

Michael Carucci Gibson Sotheby's International Realty

Innovative architectural design and the finest in contemporary finishes come together in this 6518 square foot luxury new construction residence situated on a private and manicured 0.75 acres in a well established, Brookline residential neighborhood. From the moment you enter through the massive glass doors, you sense the seamless connection of generously proportioned and meticulously designed

The Shulkin Wilk Group Compass

One of the most sought after addresses in Chestnut Hill. This unique international style contemporary home is sited on 1.78 acre lot with lush grounds and mature trees creating unparalleled privacy. This rare find is an opportunity to make this home your own and the property of a lifetime. Located on a private road, a true urban/suburban location that makes for easy and luxurious living. Quick

Erin Baumgartner Compass

This distinguished residence is nestled on a quiet, tree-lined street in one of Brookline’s most sought-after neighborhoods. Combining timeless elegance with modern luxury, this home was thoughtfully renovated and designed with a layout that blends comfort and sophistication. The main entry leads to the formal living and dining rooms, a sunlit sitting room and spacious family room. The chef’s

Maggie Gold Seelig MGS Group Real Estate LTD

Welcome to 88 Essex Road, a breathtaking home located on over an acre of land, on a private road in the heart of Chestnut Hill, Newton. This residence features 5+ spacious bedrooms and an open and airy layout. The first floor includes an expansive chef’s kitchen which is open to a bright breakfast area and family room, while the spacious living and dining rooms flow seamlessly to a patio, perfect

Maggie Gold Seelig MGS Group Real Estate LTD

Once-in-a-lifetime opportunity in Olde Chestnut Hill - this grand turn of the century victorian home is situated on almost 1 acre and offers mature trees and plantings, a large private back yard, and a separate 2+ car barn. Walking distance to many area amenities and public transportation, this elegant home is perfectly sighted away from the street and offers supreme privacy. Many restored

Michael Harper MGS Group Real Estate LTD

Privately nestled on a cul-de-sac in the prestigious Chestnut Hill, Brookline area this exceptional 7-bedroom Estate seamlessly blends timeless elegance with modern luxury. Spanning over 7,100SF, the home offers expansive living areas, dedicated office spaces, a gourmet kitchen with high-end appliances, and a luxurious primary suite with a spa-like bath. Multiple en-suite bedrooms provide comfort

Elegant & Sophisticated describe this meticulously designed private residence in a sought after Chestnut Hill neighborhood of Brookline. This 5 bed/5.5 bath home has been totally renovated with state of the art finishes and technology. The main level offers a stunning gourmet chef's kitchen & family room that lead out to a gorgeous outdoor living area featuring a heated blue stone patio, hot tub,

Jeff Groper Coldwell Banker Realty - Newton

Center Entrance Colonial on over 12,000 sq ft of elevated land in Hayes School (former Heath) district. This 8-room, 4-bed, 2.5-bath home features a fp formal living room, a sun-filled 3-season porch opening to a lovely backyard, a separate dining room, an eat-in kitchen with adjacent den, and a half bath on the main level. The second floor offers four bedrooms, a full bath, and a pull-down attic

Eileen Strong O'Boy Hammond Residential Real Estate

Located in Chestnut Hill, this beautiful south facing Colonial Revival-style residence has a magnificent yard and gardens with a patio. The front entrance opens to an elegant foyer leading to an living room with exquisite original detail and fireplace, and conservatory with windows on all sides. The dining room, also with fireplace opens to a sun-filled sitting room. The updated kitchen

Debby Belt Hammond Residential Real Estate

5 Eliot Avenue offers investors the opportunity to purchase a fully leased residential three-family property located in Brookline, Massachusetts. Two units are comprised of two-bedroom, one-bathroom units, with (one) three-bedroom, two-bathroom unit. The three-bedroom, two-bathroom unit spans two floors and includes in-unit laundry, +/-1,600 square feet, mini-split systems, and allows

Carleton Ashley Compass

This beautifully renovated single-family home in Chestnut Hill combines timeless elegance with modern amenities. Spanning four levels, it features five spacious bedrooms and three full bathrooms with custom finishes, plus two well appointed half baths. The open-concept living areas include a formal living room and a den, both with oversized windows. The chef's kitchen includes stainless steel

The Mazer Group Compass

Rare opportunity for investors/developers to own Chestnut Hill brick two family located near Longwood Medical area, Northeastern U, BU, BC, VA Medical Hospital and bustling shops/restaurants. Public transportation via bus 60 (Boylston/Route 9) is right outside and with close proximity to train (green line D train). Scenic Brookline Reservoir and Jamaica Pond nearby. Both units are currently

Mary Lochner Hurwitz Coldwell Banker Realty - Brookline

This stunning Chestnut Hill estate blends historic charm with modern convenience. Showcasing exquisite millwork and bespoke details, the home offers a gracious living room with a fireplace and three-season porch, a family room with custom built-ins and oversized windows, and a formal dining room with a butler’s pantry and fireplace. The chef’s kitchen features an oversized island, a window-lined

Maggie Gold Seelig MGS Group Real Estate LTD

Nestled between Fisher Hill & Chestnut Hill, 265 Dean offers the perfect blend of urban convenience & suburban comfort. This 6+ bedroom Colonial Revival was fully gutted in 2021 to meet modern family needs while preserving its historic charm. Expansive chef's kitchen features Sub-Zero & Thermador appliances. It opens to a bright family room with custom built-ins. A larger formal living room

Jeff Hamilton Columbus and Over Group, LLC

Chestnut Hill. Magnificent landmark brick Georgian-style residence and carriage house on nearly an acre of spectacular park-like grounds with rolling lawns, mature trees, and extraordinary gardens. This premier residence, with timeless elegance and nearly 7,000 square feet, is appointed with custom designed living space, exceptional architectural detail, and is well suited for grand scale

Alexandre Lecarme Hammond Residential Real Estate

Shingle style stunner located in Brookline's estate area. Put your touches on this 7000 sq ft home w/ a timeless architectural style built by one of Greater Boston's premier builders. This home is filled w/ large picture windows overlooking the beautifully landscaped one acre grounds. High ceilings & filled with sunlight. Enter this home thru a gallery perfect for an art collection. First floor

Melissa Dailey Coldwell Banker Realty - Wellesley