Chestnut Hill MA Real Estate & Homes for Sale

Located in Chestnut Hill, this stunning home boasts 4 beds, 2.5 baths, and a perfect blend of functionality & luxury. The kitchen, a masterpiece of design, features a grand 10-foot island equipped w/beverage drawers & a secondary dishwasher, ideal for hosting gatherings. Recently renovated in 2020, the home maximizes space on each floor. The first level showcases a sunlit dining room, a spacious living room w/ gas fireplace, a mudroom, & a private home office. The primary suite, a recent addition, offers breathtaking sunrise views, a cozy gas fireplace, & a spa-like ensuite bath. The lower level, beautifully finished, provides versatile living options, including an exercise room and a home theater area, along w/abundant storage. Situated on a large, private lot, the property boasts a professionally landscaped yard, mature trees, & a blue stone patio, perfect for outdoor gatherings. Enjoy the convenience of nearby amenities as well as easy access to the Longwood Medical Area & Boston.

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.

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.

Conveniently located in the heart of Chestnut Hill is a recently renovated 2-bedroom, 1-bathroom condo. This sunny and bright condo features hardwood floors throughout and a window in every room. The condo attributes a new modern, updated eat-in kitchen with white shaker cabinets, stone countertops, and newer stainless-steel appliances. The ample bedrooms are similar in size. The condo has so many closets! Heat, hot water, 1 deeded parking space, snow removal, and grounds are included in the condo fee. The Woodside Condominium Community features an inground pool, tennis courts, barbeque area, visitor parking laundry in building and a playground. This condo is near many options for public transportation, 51 bus and easy highway access. The condo is minutes away from so many local shops, restaurants, outdoor space and VFW Parkway! This is a gem you don't want to miss!

Nestled on a picturesque street in Chestnut Hill, South Brookline, this 4 bed, 3.5-bath sanctuary blends charm with modern luxury. Meticulously maintained over 32 years, this home boasts warmth and character. Enter through the mudroom to an graceful living room with a wood mantel fireplace, flowing into a dining room and bonus room for gatherings. Kitchen offers ample counter space and sizable table area. Half bath and home office complete the main floor. Upstairs, has four bedrooms, including an extra-large en-suite main bathroom with a walk-in closet and cathedral ceiling. A pull-down staircase leads to a full attic. The lower level features a 3/4 bath, laundry & bonus room, and a large entertainment space directly accessing the sunkissed and lush yard. A private oasis with a stone patio, irrigation and plentiful storage. Steps from the 86-acre Allendale Woods, this home offers outdoor adventures, gardening, walking trails..

Explore luxury, comfort, and convenience in South Brookline's prestigious Baker School district. This Cape-style home boasts an open floor plan with a wood-burning fireplace, a spacious kitchen that opens to a sunlit dining area and expansive deck, perfect for entertaining. It features three large bedrooms, a full bath and half bath on the main level, plus additional space on lower level including a fourth bedroom, full bath, gym, rec room, bonus room, and laundry. The large walk-up attic offers ample storage. Enjoy a two-car garage with direct home access, an outdoor grill on a natural gas line, and a wide driveway, situated on a vast 13,950 square foot Corner Lot! So much abundant space, there's room for everyone to relax and unwind in style! With easy access to the Longwood Medical Area, downtown Boston, and Chestnut Hill, this home is ideal for those desiring space and elegance in a sought-after location.

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 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!

This contemporary masterpiece in Brookline boasts solid, soundproof construction in a tranquil setting among the trees. With an open floor plan that allows for maximum customization of the space " 71 Grove features enormous picture windows that offer abundant natural light, massive living and dining areas, and a state-of-the-art custom kitchen that is sure to impress. Take advantage of 5 total bedrooms including a primary suite bathroom with a soaking tub and spacious shower. Entertain on one of two large outdoor decks complete with stone fire pit. Additional features include a balcony, two-car garage, heated driveway, and in-law suite. Take advantage of easy access to area shops and restaurants and close proximity to the Fenway area and downtown Boston. The ultimate living experience awaits.

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.

Rare is the opportunity to own a custom built home so soon after initial occupancy. Barely 3 years ago this home was completed and delivered as one of the finest creations in the coveted Country Club neighborhood of Chestnut Hill. Nestled amidst a lush and protected landscape of mature plantings, this stunning, transitional home sits on over an acre of level land. The timeless home sits centrally within the lot offering an impressive 3 floors of living area. The signature architectural element is a 12' wall of windows facing south to allow sunlight throughout the seasons. The design was completed by the firm of Marcus Gleysteen while the masterful build was the work of a team of refined experts at Brendon Properties. Woven together, the finished product blends exceptional craftsmanship with state of the art technology to create a residence of unparalleled sophistication. Check the property's custom website for many more details, videos and specs.

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

Lovely first-floor two-bedroom unit at Chestnut Hill Village. Sits pretty in a quiet setting. Recently fully renovated kitchen and bathroom. Replacement windows, hardwood flooring throughout the entire unit. Spacious closets in each bedroom. Heat and hot are included in the condo fee, this is perfect for owner occupant or investor. Pool and tennis court, 2 deeded parking spaces. It is perfectly located close to many shops and restaurants on Center st West Roxbury as well as 1 mile away from route 9 and Chestnut Hill Mall. Pet friendly. Great condo association with plenty on reserve funds. Please contact listing agent for showings.

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

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.

A rare opportunity to own a beautiful new construction home in a quiet, desirable Chestnut Hill neighborhood, with a private back yard! Featuring a custom chef's kitchen with Subzero/Wolf appliances. Two dishwashers and a walk in pantry. A welcoming, spacious foyer flows into an open concept dining room with a custom built wet bar. A sunlit kitchen is open to the family room and leads to an oversized deck overlooking beautiful conservation land. A full bedroom/office with a large mudroom complete the first floor. Second floor has 4 en-suite bedrooms and a large laundry room. A charming primary suite boasts a cozy fireplace and two expansive closets, offering both warmth and ample storage for your comfort and convenience. Luxurious bath with heated floors, soaking tub and tiled shower. Finished lower level offers a comfortable bedroom and a spacious open area, ideal for living and entertaining.

Fantastic 3 bed, 2.5 bath townhouse that lives like a single family with large front & side yard & private front door entrance overlooking Tanglewood Road. The main level of the home features a spacious master suite with walk in closet, spa-like master bath with double vanity, custom tub & steam shower. Kitchen with new oven & microwave granite counters & bar seating open to the living & dining rooms with wood burning fireplace & slider to private deck. A half bath finishes off the main level. Upstairs you will find two bedrooms, a full bath with custom walk-in tub & a separate laundry room. The finished lower level, with heated tile floors & wet bar, offers additional living space for a family room or potential home theater. Other features include gas heat, gas cooking, central A/C, hardwood floors, whole house water filtration system, 2 car garage, 1 outdoor parking space. Nearby amenities include Wegmans, LifeTime Fitness, The Shops at Chestnut Hill, The Street Chestnut Hill & more.

Fantastic 3 bed, 2.5 bath townhouse that lives like a single family with large front & side yard & private front door entrance overlooking Tanglewood Road. The main level of the home features a spacious master suite with walk in closet, spa-like master bath with double vanity, custom tub & steam shower. Kitchen with new oven & microwave granite counters & bar seating open to the living & dining rooms with wood burning fireplace & slider to private deck. A half bath finishes off the main level. Upstairs you will find two bedrooms, a full bath with custom walk-in tub & a separate laundry room. The finished lower level, with heated tile floors & wet bar, offers additional living space for a family room or potential home theater. Other features include gas heat, gas cooking, central A/C, hardwood floors, whole house water filtration system, 2 car garage, 1 outdoor parking space. Nearby amenities include Wegmans, LifeTime Fitness, The Shops at Chestnut Hill, The Street Chestnut Hill & more.

Recently renovated home, this modern style 2 bedroom condo is a true gem. LOW HOA $243! High ceilings and sun lit rooms, it offers a refreshing living experience. Prime location, situated in a highly sought-after Chestnut Hill neighborhood, this home has easy access to major route such as Rt 128/95, Mass Pike, MBTA, and as a bonus BWH Shuttle is right across the street. Low HOA of $243. Beautifully completed open concept Livingroom and kitchen layout with modern stainless-steel appliances. The modern, sleek kitchen is a focal point, featuring an island/ breakfast bar where friends and family can gather. Stylish hardwood floors throughout, and central AC & heating for the home. Closing proximity to Brookline schools systems. Also a heated private garage parking comes with the home. Reach out for a private showing!

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.

Classic New England Townhouse at Fairgreen Place convenient to the heart of Chestnut Hill. This 6-room, 2 bedroom, 3 bath home has classic architectural details creating a warm and inviting atmosphere. The main entrance welcomes you with a spacious foyer leading to formal living and dining areas, a sunlit kitchen with a charming bay window and direct access to the 1 car garage. The spacious living room features a wood burning fireplace and access out to the private fenced bluestone patio area. The den complete with gas fireplace and adjoining full bath, offers flexible living options. Upstairs, two spacious bedrooms with en-suite baths await, alongside a laundry room, office area with extra storage, and a cedar closet. Near Chestnut Hill's best shops and restaurants, this townhouse blends classic charm with contemporary living.