Chestnut Hill Real Estate | Chestnut Hill Homes for Sale

7 Beds ⋅ 11 Baths ⋅ 73445544 MLS ⋅ ACTIVE Status

Introducing Paine Estate, a grand Georgian Revival architectural treasure located in the highly coveted Chestnut Hill neighborhood of Brookline. This outstanding property has been extensively renovated, now combining traditional style and modern amenities with a thoughtful floor plan ideal for comfortable family living and grand entertaining. Exceptional features include a grand entry hall, elegant formal sunken living room overlooking the picturesque gardens, fireplaced dining room, gourmet chef's kitchen, family room, handsome wood paneled library and an expansive great room. 6 bedrooms include the luxurious primary suite complete with separate bathrooms and dressing rooms and balcony. Additional features include a mudroom, exercise/club room, au-pair suite and wine cellar. This majestic home is surrounded by over 2 acres of beautifully landscaped grounds featuring an outside kitchen and dining area, a formal parterre garden and plunge pool. Magnificent opportunity not to be missed!

1014 Boylston Street, Brookline

$9,985,000

5 Beds ⋅ 8 Baths ⋅ 73478330 MLS ⋅ ACTIVE Status

Set on .74 acres in one of Brookline’s most coveted neighborhoods, this newly constructed estate blends timeless architecture with exceptional modern design. With impeccably finished living spaces and full AV wiring, it offers 5 bedrooms, 6 full and 2 half baths, and a layout ideal for today’s lifestyle. The heart of the home is a showstopping chef’s kitchen with top-tier appliances, custom cabinetry, and a large island opening to sun-filled living and dining areas. A seamless indoor-outdoor flow connects to the private, flat tree-lined lot—perfect for entertaining or relaxation. Highlights include a luxurious primary suite with spa bath, generous secondary bedrooms, family room and a versatile finished lower level, attached 3-car garage with heated driveway, permitting for a pool. Built by a renowned local builder, this move-in-ready residence offers unmatched style, craftsmanship, and comfort in one of Brookline’s most desirable settings. Just bring your toothbrush!

68 Clyde Street, Brookline

$8,995,000

6 Beds ⋅ 7 Baths ⋅ 73479457 MLS ⋅ ACTIVE Status

Exquisite in every detail, this magnificent brick Georgian boasts modern style design, suitable for grand scale entertaining & comfortable family living. A large, elegant foyer w/sweeping staircase & venetian plaster walls, opens to an elegant living room w/fireplace. A sunroom, just off the foyer, offers spectacular views of the level, acre+ lot w/ frontage on Cramond Street. There is a majestic dining room w/acoustic padded walls & a handsome family room w/custom cabinetry. The fully renovated chef’s kitchen features a center island, butler’s pantry & dining nook—truly exceptional w/top-grade appliances. The 2nd level has a luxurious primary suite w/fireplace & spa-like bath. There are 3 additional bedrooms, 3 full baths, an office & a laundry room on this level. The 3rd floor offers 2 additional bedrooms & a full bath. The lower level has a large media room, gym room, full bath, 2nd laundry room, mudroom & access to the 2-car garage. Easy access to highways, schools & airport.

188 Heath St, Brookline

$8,200,000

6 Beds ⋅ 9 Baths ⋅ 73526856 MLS ⋅ ACTIVE Status

Set on over 1.2 acres with a 1.62-acre experience via a neighboring easement, this exceptional Chestnut Hill estate offers a tranquil oasis on one of the area’s most coveted and secluded streets. Originally built in 1900 and thoughtfully renovated over time, the residence spans more than 9,300 square feet with six bedrooms, six full bathrooms, and three half bathrooms. Its richly detailed living spaces were designed for both elegant entertaining and everyday comfort. Gracious formal rooms, soaring ceilings, and exquisite millwork overlook beautifully landscaped grounds featuring a heated, in-ground pool, a basketball court, and ample parking. Once home to Alvan T. Fuller, the 50th Governor of Massachusetts, the property carries remarkable historic provenance. The grounds were originally designed by Frederick Law Olmsted, further contributing to the property’s timeless character. This is a rare opportunity to own a historic estate of this scale in an unbeatable location.

40 Singletree Rd, Brookline

$7,995,000

8 Beds ⋅ 9 Baths ⋅ 73590108 MLS ⋅ ACTIVE Status

334 Hammond Street presents a rare opportunity to own a distinguished Georgian Revival residence, lovingly maintained and thoughtfully evolved by the same family for the past 25 YEARS. Set back from the road behind its classic brick façade, this circa-1900 home is remarkably understated from the street, revealing an unexpected sense of scale and versatility within. Generously proportioned rooms, beautifully preserved architectural character, and restored Palladian windows speak to the home’s history, while thoughtful updates and a more contemporary rear addition reflect the way it has evolved for modern living. With 8 bedrooms, expansive gathering spaces, and a finished lower level complete with an in-law suite, the floor plan offers exceptional flexibility for family, guests, work, and entertaining. One of the property’s most distinctive features is the detached indoor swimming pool, creating a private retreat that can be enjoyed in every season. Carefully cared for through the years, 334 Hammond Street offers the character and presence of a historic Newton home together with the space and adaptability to serve its next generation for years to come!

334 Hammond St, Newton

$6,400,000

4 Beds ⋅ 5 Baths ⋅ 73500458 MLS ⋅ ACTIVE Status

A magnificent home located in the highly coveted estate section of Brookline directly across from the famed Country Club. 198 Clyde Street is a wonderful cape style estate perfectly adapted to modern living. The property offers 6,521 square feet of living space located on just under 1 acre of impeccably landscaped grounds. Beautifully appointed interiors include grand formal living and dining rooms overlooking the outdoor space, a gourmet kitchen, and a spectacular family room with double-height ceilings. The luxurious primary suite is complete with separate dressing rooms and bathrooms and direct access to an outdoor sitting area. The exterior is as wonderful as the interior with multiple outdoor patios, a sprawling lawn and a pergola. Additional features include a 2-car garage, laundry room, home office, wine cellar, wood paneled den and a custom hockey training area. This outstanding home is minutes from Larz Anderson, Dexter/Southfield, Park School, and The Street at Chestnut Hill.

198 Clyde Street, Brookline

$5,627,000

9 Beds ⋅ 6 Baths ⋅ 73469901 MLS ⋅ ACTIVE Status

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 historical details include a formal foyer with grand staircase, multiple fireplaces, and reclaimed hardwood flooring. Flooded with natural light this gracious home offers a large eat-in kitchen that overlooks the back yard, a banquet sized formal dining room, and a double parlor that is ideal for entertaining. The second floor of the home is complete with 4+ bedrooms, including a bright primary bedroom with en suite bath and study. The top floor boasts 3+ bedroom, large laundry room. Abundant storage throughout, partially finished basement, plus an outdoor covered loggia in the heart of Chestnut Hill

394 Hammond St, Newton

$4,980,000

5 Beds ⋅ 7 Baths ⋅ 73579970 MLS ⋅ ACTIVE Status

Welcome to 90 Suffolk Road, a truly special Chestnut Hill residence where classic architecture, beautiful proportions, and a warm, welcoming feel come together on approximately one private acre. From the moment you arrive, there is a sense of space, privacy, and timeless elegance that makes this house feel like home. Sunlight fills the gracious main level, where generously sized rooms flow naturally from one to the next. The spacious cooks kitchen is made for gathering, while the elegant living and dining rooms provide the perfect setting for entertaining. A fireplaced den or office offers a cozy retreat, and the living room fireplace adds warmth and character. A beautifully appointed in-law suite with full bath provides exceptional flexibility for guests or extended family visits. A wraparound deck overlooks the expansive grounds. Upstairs, the primary suite is a peaceful retreat, with a spa-like bath, two custom walk-in closets, and beautiful views across the property. Three additional spacious bedrooms and 2 bathrooms complete the second level. The walk-out lower level adds another dimension to the home, with a comfortable family room, playroom, and bonus office space. The grounds are magical—private and lush, and offering a rare sense of space in one of Chestnut Hill's most sought-after neighborhoods. Close proximity to Boston, public transportation, major hospitals, schools, and shopping.

90 Suffolk Rd, Newton

$4,795,000

4 Beds ⋅ 5 Baths ⋅ 73520842 MLS ⋅ ACTIVE Status

Nestled on a private 0.92-acre lot in the prestigious Chestnut Hill neighborhood, this exceptional custom-designed Mid-Century Modern ranch, inspired by the timeless architecture of Frank Lloyd Wright, offers a rare blend of sophistication, privacy, and seamless indoor-outdoor living. Thoughtfully designed with gracious proportions and walls of glass, the home is filled with natural light and overlooks beautifully landscaped grounds. A spectacular four-season breakfast room with four skylights complements the chef’s kitchen featuring top-of-the-line appliances, three ovens, two dishwashers, and custom cabinetry. The luxurious primary suite serves as a private sanctuary with dual showers and vanities, smart toilets, separate dressing areas, a soaking tub, and an attached office/library. The versatile lower level with separate entrance offers excellent potential for an in-law suite. Sliding glass doors line the rear of the home, opening to a serene outdoor retreat with an elegant patio and heated pool. Superb Chestnut Hill location with easy access to Boston, shopping, dining and Medical Centers.

9 Singletree Rd, Brookline

$4,650,000

6 Beds ⋅ 7 Baths ⋅ 73532609 MLS ⋅ ACTIVE Status

Exceptional 2016 brick Colonial offering 6,359 sq. ft. of beautifully finished living space with 6 bedrooms, 6.5 baths, including a main-level bedroom suite, and a heated 3-car garage. Set on a private, professionally landscaped .38-acre level lot on a quiet, tree-lined street in desirable Chestnut Hill, this meticulously maintained home offers generous scale, modern amenities and move-in-ready condition.A grand two-story foyer introduces the light-filled main level, where 10' ceilings, hardwood floors and detailed millwork complement well-proportioned rooms. An elegant living room with fireplace connects to the formal dining room and a butler’s pantry with sink, dishwasher and extensive cabinetry.The open kitchen features a center island, premium appliances, custom cabinetry and dining area, and flows directly into the spacious family room with fireplace and floor-to-ceiling windows overlooking the grounds. French doors open to stone patios and the expansive lawn perfect for outdoor entertaining. A powder room and mudroom with built-in cubbies and access to the garage complete this floor.Upstairs, hardwood floors continue throughout. The spacious primary suite features a fireplace, large walk-in closet, generous bath and oversized windows overlooking the grounds. Four additional bedrooms, including two with ensuite baths and one currently used as an office, plus a full bath, laundry room and open landing with Juliet balcony complete the second floor.The expansive finished lower level provides additional space for recreation, work and entertaining, including a home theater/game room with bar, exercise room, private office, full bath, wine room ready for customization and ample storage, with bulkhead access to the backyard.Solar panels installed in 2026 provide energy savings and net-metering benefits. Convenient to public and private schools, shopping, dining, golf, and Boston, this substantial Chestnut Hill residence offers an exceptional combination of space, privacy, condition and modern functionality.

129 Rangeley Rd, Brookline

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