Chestnut Hill MA Real Estate & Homes for Sale

Nestled in the heart of Chestnut Hill, this 6BD, 4.5BA c1892 home features timeless design and period detail. Architecture enhanced by bespoke details, intricate millwork, crown moldings, and 6 fireplaces. Spanning 5,689SF+, layout ideal for entertaining and modern living. Living room with FP and 3-season porch. Family room with custom built-ins, FP, and large windows. Dining room with built-ins, FP, and pantry. State-of-art kitchen with island and window-lined eat-in. Mudroom and bath complete floor. 2nd floor features primary wing with spa-like bath, en-suite bed, 2 add'l beds, full bath, and laundry. 3rd floor provides 2 beds and full bath. Basement offers ample storage. Oversized 2-car garage. Driveway snowmelt system. .67-acre lot provides peaceful setting close to city conveniences, including 'The Street', local restaurants & shops. Minutes to top public & private schools. Ideal for commuters, Green "D' line a block away. Quick access to Longwood, Boston, Cambridge, and Logan.

Recently renovated & LEAD COMPLIANT two-family home in the highly sought after Chestnut Hill area of Brookline, just across from beautiful Soule Recreation Park. First-floor unit gets tons of natural light and features 2bds/1ba, living room & separate dining room, kitchen w/ pantry and rear deck. Second-floor owner's unit has undergone extensive renovations creating a bright, airy & inviting atmosphere featuring 3bds/2ba, an enclosed front facing porch that would be perfect for a home office, kitchen w/ pantry, separate family room and office on third floor, plus rear deck. Both units have in-unit laundry, hardwood floors throughout & there is ample storage space in the basement. 2-car garage plus driveway parking for up to 3 cars. A perfect commuter location w/ Green D line located nearby & easy access to route 9 w/ routes to Longwood Medical Area, Boston or west to the Pike & route 128. Excellent location near grocery, shopping, restaurants, coffee shops & gyms! Don't miss this one!

Beautiful Center entrance Colonial that is enhanced by a beautiful setting and land consisting of 29,814sf. The home is comprised of 6 bedrooms, 5 1/2 bathrooms and located on a private roadway. The major addition in 1998 likely added significant space and features to the property. It seems like it's ready for it's next phase to enhance its charm and functionality further. Home is listed for its assessed value surrounded by many exclusive properties .Easy to show.Call Linda

A rare and unique opportunity to make this 1950s International Style Modern home with private tennis court your very own estate. Sited on 1.78 acres of lush grounds, mature trees, and stairs that lead to your very own secret garden. Add your own creative style to this extraordinary bucolic setting just minutes from urban amenities. Close to the Chestnut Hill D line stop,"The Street" shopping, restaurants, world renowned hospitals, and 12.7 miles to Logan Airport. Rendered photos are of the Chestnut Hill Historic approved plans. Transferable CAD plans. Buyer to do their own due diligence.

A bespoke jewel of a home steeped in historical value. The former 'Gardener's Cottage' for the Webster Estate in Old Chestnut Hill has been seamlessly blended into a larger footprint with contemporary additions including a gym, steam room, 5 fireplaces & a masterful 1900 bottle wine room. The large open Chef's kitchen boasts an oversized center island and stainless appliances. Multiple windows and French doors afford plenty of light and easy access to the expansive rear corner yard with pool, jacuzzi & Har-Tru tennis court. Choice living areas include a stunning sunroom and a more formal living room and dining area which opens dramatically off the main foyer. The second level primary suite offers a striking vaulted ceiling, grand stone fireplace, office with large balcony and a luxe spa bathroom. A family game room downstairs hosts an impressive home theatre. A charming Nanny's suite located above the garage with a private entrance completes this magical estate, moments to Longwood CC.

This bright full floor 2 bed, 2 full bath condo in Chestnut Hill is a charmer. It's situated on a dead end, private street near all of the popular shops, restaurants, medical facilities, gyms and conservation land. .8 miles to the Chestnut Hill "T". This unit has hardwood throughout, many updates including 2023 kitchen upgrades with white cabinetry, subway tile backsplash and ss appliances, some interior paint and new shower tiles (2024) The front porch area and back patio are "exclusive use" to Unit #1.This well managed condo association with low condo fees has taken great care of the building. Over the years they repaired or replaced items of necessity including gutters, interior and exterior paint, reinforced/repaired back porches and more. One garage space is assigned to this unit and a 15' x 15' storage unit. Lots of parking on this private street 24 hour a day, every day. What are you waiting for? Lovely unit, fantastic location, lots of storage and parking.

Nestled within Chestnut Hill's esteemed estate neighborhood, this distinguished manor on a .93 acre lot exudes timeless elegance reminiscent of the French Renaissance. The layout of the main house, an architectural gem built in 1993, presents a remarkable opportunity for customization, with space well-suited for 5-6 en suite bedrooms. Meticulously maintained, the property has recently completed a significant amount of improvements including a new HVAC system, updated electrical, flooring, insulation, plumbing, and a full restoration of the roof and exterior. Additionally, the attached carriage house evokes a bygone era and offers a haven of leisure with space for recreation and relaxation. While 335 Heath beckons for revitalization, there is boundless potential. Immerse yourself in the possibilities that await within this remarkable and historic estate.

Spectacular, one-of-a-kind, free-standing home in the heart of Chestnut Hill. Although part of the Hammond Pond Place condominium association, there is no condo fee, and it lives like a single family home. This young contemporary-style residence has a beautiful open-concept floor plan. Among its many features are walls of windows, soaring ceilings, and a gas fireplace. The large dining area has an atrium door that opens to a two-tiered deck with a hot tub. The custom kitchen has maple cabinets, granite counters, and separate pantry storage. The second level has four generously sized bedrooms, including a luxurious primary suite w/an oversized walk-in closet and spa-like bathroom. The lower level offers space for a playroom, gym & ample storage. There is a direct entry 2 car garage that leads into the mudroom. Fabulous private outdoor space, for grilling & entertaining. Convenient to Chestnut Hill shopping and major routes.

Spectacular, one-of-a-kind, free-standing home in the heart of Chestnut Hill. Although part of the Hammond Pond Place condominium association, there is no condo fee, and it lives like a single family home. This young contemporary-style residence has a beautiful open-concept floor plan. Among its many features are walls of windows, soaring ceilings, and a gas fireplace. The large dining area has an atrium door that opens to a two-tiered deck with a hot tub. The custom kitchen has maple cabinets, granite counters, and separate pantry storage. The second level has four generously sized bedrooms, including a luxurious primary suite w/an oversized walk-in closet and spa-like bathroom. The lower level offers space for a playroom, gym & ample storage. There is a direct entry 2 car garage that leads into the mudroom. Fabulous private outdoor space, for grilling & entertaining. Convenient to Chestnut Hill shopping and major routes.

This incredibly crafted residence, built in 2022 and designed by Boston's premier luxury female builder, exceeds all expectations of a luxury home. Grand entertaining and luxurious living is the name of the game with a vast, open, first floor with palatial rooms, a grand 2-story foyer, and a sitting room " not to mention a custom kitchen and separate prep kitchen with luxury-level appliances. Also enjoy a first-floor library, au-pair suite, and expansive mudroom. The second floor features the primary suite we've all dreamed of " an immense bedroom with sitting area, fully custom walk-in closet, spa-like bathroom, water closet, and makeup counter. Four additional large en-suite bedrooms and a laundry room with counter space and built-ins complete the second level. This incredible home also boasts a custom wine room, expansive storage space, an acre of manicured grounds, and much more.

The Chestnut Hill Reservoir provides a picturesque backdrop for this open concept, lavish one bedroom with a chef's kitchen, expansive windows & soaring ceilings. A spacious & sophisticated living/dining area offers panoramic views of the reservoir. The kitchen is equipped with a Sub-Zero, Wolf Stove, dishwasher, ample cabinet space, & a welcoming island. This thoughtfully designed home includes a sun-filled bedroom, luxurious bathroom with an enclosed glass shower, in-unit laundry, AC, & parking spot #70. The condo offers a variety of amenities: gym, function room, snow removal, landscaping, & attentive on-site staff. Living at The Waterworks combines the tranquility of Chestnut Hill with the vibrant city life, w/ downtown Boston just a short distance away. Located near the C & D lines makes it easy to access Boston's renowned restaurants, cultural attractions, Newton Centre, Coolidge Corner, & the Longwood Medical area. Find your niche in one of Boston's most desirable neighborhoods.

The Chestnut Hill Reservoir provides a picturesque backdrop for this open concept, lavish one bedroom with a chef's kitchen, expansive windows & soaring ceilings. A spacious & sophisticated living/dining area offers panoramic views of the reservoir. The kitchen is equipped with a Sub-Zero, Wolf Stove, dishwasher, ample cabinet space, & a welcoming island. This thoughtfully designed home includes a sun-filled bedroom, luxurious bathroom with an enclosed glass shower, in-unit laundry, AC, & parking spot #70. The condo offers a variety of amenities: gym, function room, snow removal, landscaping, & attentive on-site staff. Living at The Waterworks combines the tranquility of Chestnut Hill with the vibrant city life, w/ downtown Boston just a short distance away. Located near the C & D lines makes it easy to access Boston's renowned restaurants, cultural attractions, Newton Centre, Coolidge Corner, & the Longwood Medical area. Find your niche in one of BOSTON's most desirable neighborhoods.

Gorgeous Brand new construction in the heart of Chestnut Hill. Conveniently located less than a mile from the Chestnut Hill Mall, the Chestnut Hill Square & the street, all containing a multitude of cafes, restaurants and shops. Close proximity to both Skyline Park and Hammond Pond, offering a variety of parks and trails for outdoor leisure. This 4 bed 4.5 bath is a hidden gem, tucked away off the Main Street yet still has Easy access to Route 9. Boasting 3000+ square feet of living space, featuring a heated garage with 2 assigned parking spots. First floor includes a half bath and beautiful open floor plan kitchen and living room that flows out onto the deck and private fenced garden. Second floor includes two spacious bedrooms, each with their own walk in closet and full baths. Third floor holds two spacious bedrooms, with their own walk in closet and full baths. As well as a dedicated laundry room and office. Massive windows offer natural light that flows in throughout the property.

Spectacular NEW CONSTRUCTION townhouse now available in the Chestnut Hill neighborhood of Brookline! Meticulously designed 4 bed, 2.5 bath with luxury finishes. Main level boasts open concept gourmet kitchen and dining roomfeaturing a Thermador appliance package,living room with custom woodwork and fireplace,laundry room and half bath. Topfloor has three generously sized bedrooms and two full baths, including a stunning master suite with lavishbathroom and two closets. Bonus bedroom on first level perfect for an office,gym or playroom with access to garage and yard. This impeccable home truly has it all and more: two car garage, laundry room on main level, and private fenced in outdoor space with patio. Minutes to shops at Chestnut Hill Mall and The Street, easy access to Route 9,restaurants & transportation. A must see!

Spectacular NEW CONSTRUCTION townhouse with single family feel now available in the Chestnut Hill neighborhood of Brookline! Meticulously designed 4 bed, 2.5 bath with luxury finishes. Main level boasts open concept gourmet kitchen and dining roomfeaturing a Thermador appliance package,living room with custom woodwork and fireplace,laundry room and half bath. Topfloor has three generously sized bedrooms and two full baths, including a stunning master suite with lavishbathroom and two closets. Bonus bedroom on first level perfect for an office,gym or playroom with access to garage and yard. This impeccable home truly has it all and more: two car garage, laundry room on main level, and private fenced in outdoor space with patio. Minutes to shops at Chestnut Hill Mall and The Street, easy access to Route 9,restaurants & transportation. A must see!

Spectacular NEW CONSTRUCTION townhouse now available in the Chestnut Hill neighborhood of Brookline! Meticulously designed 4 bed, 2.5 bath with luxury finishes. Main level boasts open concept gourmet kitchen and dining roomfeaturing a Thermador appliance package,living room with custom woodwork and fireplace,laundry room and half bath. Topfloor has three generously sized bedrooms and two full baths, including a stunning master suite with lavishbathroom and two closets. Bonus bedroom on first level perfect for an office,gym or playroom with access to garage and yard. This impeccable home truly has it all and more: two car garage, laundry room on main level, and private fenced in outdoor space with patio. Minutes to shops at Chestnut Hill Mall and The Street, easy access to Route 9,restaurants & transportation. A must see!

Spectacular NEW CONSTRUCTION townhouse with single family feel now available in the Chestnut Hill neighborhood of Brookline! Meticulously designed 4 bed, 2.5 bath with luxury finishes. Main level boasts open concept gourmet kitchen and dining roomfeaturing a Thermador appliance package,living room with custom woodwork and fireplace,laundry room and half bath. Topfloor has three generously sized bedrooms and two full baths, including a stunning master suite with lavishbathroom and two closets. Bonus bedroom on first level perfect for an office,gym or playroom with access to garage and yard. This impeccable home truly has it all and more: two car garage, laundry room on main level, and private fenced in outdoor space with patio. Minutes to shops at Chestnut Hill Mall and The Street, easy access to Route 9,restaurants & transportation. A must see!

Brand new construction in the heart of Chestnut Hill, offering proximity to the Chestnuthill mall, restaurants, cafes, movie theater, shopping, grocery stores, a gym, hiking trails & conservation area and a golf course! This 4 bed 4.5 bath is a hidden gem with easy access to Route 9 & 3000+ square feet of living space, featuring a heated garage with 2 parking spots. 1st floor includes a half bath and beautiful open floor plan kitchen/ living room that flows out onto the deck and private fenced garden. 2nd & 3rd floor includes four spacious bedrooms, each with their own walk in closet and full baths. As well as a dedicated tiled laundry room and bonus room/office. Basement has tiled mudroom entry, from garage with walkup to first floor. Massive windows offer natural light that flows in throughout the property. This Townhouse Condo is an ideal alternative to single family with the added convenience, covering water, sewer, master insurance, and snow removal all managed by the HOA.

Property in Boston. Spectacular North-Easterly views of Chestnut Hill Reservoir, Cassidy Park and the City from this 1,990sf penthouse loft-like Watermark unit. Open-plan, 9'_6" ceilings, wood floors. Living room: Walls of glass, gas fireplace flanked by glass doors that lead to 800+sf open air patio. Dining room with access to outside, has built-in shelves and opens to living room. Kitchen has bar seating for three, open to living spaces. Main bedroom has 10-foot ceilings, large walk-in closet and sumptuous bathroom. Second bedroom has its bath ensuite. Third bedroom doubles as office with exterior access to the patio. Half bath is available for guests. Unit control of 4 zones of HVAC. Laundry is in unit. Two deeded garage parking and storage. Take elevator from garage to unit level. Concierge service weekdays, fitness center. Running/walking path at Chestnut Hill Reservoir across the street. Convenient to the Cleveland Circle and the MBTA (C &D) Green line.Truly a rare find

The rarest of rare! No expense has been spared to create this sophisticated home. This stunning unit is renovated to the highest standard with quality craftmanship throughout. Top of line finishes and thoughtfully designed choices created this perfect condominium. This grand home showcases tremendous space, light and well-proportioned rooms and allows entertaining on an elegant scale. This exquisite condo at the coveted Chestnut Hill Towers offers stylish luxurious amenities and an immaculately maintained building in the middle of most vibrant neighborhood in Chestnut Hill. 24-hour doorman underscore it all. From the moment you drive up to the imposing porte-cochere, the Towers offers the ultimate in privacy, service and luxury. Minutes to Longwood, Back Bay, Beacon Hill, South End and Downtown Boston/Financial District. Virtual tour is attached to this listing.

This sprawling condominium with western exposure and awe-inspiring views is truly a rare find at the Towers of Chestnut Hill. This corner unit showcases wonderful space, light and well-proportioned rooms and expands nearly 1000 sq. ft. and feels even larger. Truly panoramic unobstructed views from every room allow the perfect backdrop for entertaining. From the moment you drive up to the circular drive, the Towers offers the ultimate in privacy, service and luxury. The Towers of Chestnut Hill sits on 17 beautiful acres in the finest area in Chestnut Hill. 24-hour doorman underscore it all. strong, healthy HOA. Solid investment.

Just completed stunning new construction residence with custom luxury finishes throughout in desirable Chestnut Hill Newton under $2.5 million. Professionally designed home by premier local builder features an ideal open floor plan, high ceilings, floor to ceiling windows and gorgeous outdoor spaces, offering 5 bedrooms, 5 full and 1 half baths including a main level guest suite/office with full bath and walk-in closet. Multiple living spaces on the main level provide access to large wrap-around porches, decks and patios. The oversized entertainer's kitchen includes top-of-the-line Miele appliances, a mammoth island, breakfast area, walk-in pantry, and butler's pantry with a seven-foot tall wine fridge. Bedroom level contains four large bedrooms, all with private baths including a gorgeous primary suite with fireplace, private balcony and full length walk-in closet. A stunning roof deck off top floor bonus space offers amazing views. Two car garage plus workout room on entry level.

This light filled Chestnut Hill residence features a fabulous open layout and luxurious finishes. The welcoming foyer leads to the dining and living areas, with breathtaking French Doors that open onto a deck and overlook the private yard, pool and sauna. The large gourmet eat in kitchen is open to the family room. A wet bar, en suite office/bedroom, powder room, and mudroom complete the first floor. On the 2nd floor, the glorious primary suite includes a generously sized bedroom with large marble spa-like bath, spacious dressing rooms and private balcony. Also on this level are 4 additional bedrooms (3 are en suite) and large laundry room. The lower level has a generous recreation room, exercise spaces, full bath, guest bedroom and storage areas. Above the attached 3 car garage is a full guest suite with bedroom and living room. This private home is move in ready with a sophisticated AV system and just minutes from shopping and restaurants with easy access to Boston. Not to be missed!

This is a stunning and spacious 2-bedroom, 2-bathroom condo with 1510 sq ft. It features beautiful gleaming floors, large Eat in Kitchen, maple cabinets, granite counters, and stainless steel appliances. The open floor plan living room and dining room have a wall of windows and a balcony with a slider that allows an abundance of light! The primary bedroom is generously sized with a full bath and several closets, including a walk-in closet. The second bedroom is spacious and has closet. This is a full-service building with 24/7 concierge, clubroom, library, fitness room, and extra storage. There is a resident superintendent and on-site management to ensure safety and convenience. The location is convenient to: shopping, supermarkets, restaurants, movie theater and a bus stop right out front that goes to Kenmore Square.Parking space #110 is outside spot, #10 is the carport space.

Welcome to Imperial Towers, one of Chestnut Hill's most sought after full service luxury elevator buildings.This exceptional, south facing 5th floor 1 bedroom, 1.5 bath unit has 1240 sq ft of living area and offers an additional large den/office that can serve as a guest room. Beautiful updated kitchen and bathrooms. The en-suite, large size main bedroom accommodates generous furnishings and beams with natural sunlight through the large picture window. Every room is spacious and offers abundant storage. Other features include; TWO outdoor parking spaces, ample guest parking, gym, sauna, clubroom, library, and storage. Beautifully appointed lobby, outdoor pool, manicured grounds and impeccable 24/7 security, concierge and on-site management office. Lifetime Fitness and Equinox are just next door, together with Wegmans Shopping Center, the Capital Grille and Chestnut Hill Mall. Bus 60 to Longwood, Fenway/Kenmore at your doorstep