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$1,575,000
4 Beds ⋅ 3 Baths ⋅ 73574921 MLS
This move-in-ready Chestnut Hill ranch offers privacy, convenience, and easy single-level living on a quiet Newton street. The sun-filled main level features four bedrooms and two full bathrooms, including a private primary suite, a beautifully renovated kitchen (2022), and two updated bathrooms (2023), plus scenic treetop views. The partially finished lower level adds a recreation room, third bathroom, laundry, and generous storage. Major upgrades include a tankless water heater (2022), new roof and two high-efficiency Mitsubishi heat pumps (2023), plus new gutters, paver patio, premium Marvin windows, and sliding glass door (2024). Ideally located near Ward Elementary School, Boston College, Newton Commonwealth Golf Course, and the MBTA Green Line B and C branches, with convenient access to downtown Boston.

18 Travis Dr, Newton

Listing courtesy of Listing Agent: Sandra Andronic from Listing Office: William Raveis R. E. & Home Services.
$2,250,000
3 Beds ⋅ 4 Baths ⋅ 73574038 MLS
Rarely available fully renovated end-unit 3 bed+office / 3.5 bath townhouse at The Residences at Chestnut Hill offers an enviable combination of privacy, space and convenience. Set back from Boylston Street and abutting a tranquil conservation area, this beautifully appointed residence has been thoughtfully renovated offering an abundance of natural light and features generous proportions, including a magnificently renovated kitchen and beautifully updated bathrooms. The main living level boasts 9’ ceilings, a convenient powder room and a chef’s dream kitchen with a center island, custom cabinetry and a charming bay-windowed eat-in area. The kitchen flows seamlessly into a spacious living room anchored by a gas fireplace and custom built-ins, a dining area and a sliding door opening to a private deck overlooking the landscaped side yard. The second floor is comprised of a spacious primary suite with two walk-in closets, in-unit washer/dryer and a luxurious en-suite bath featuring a double vanity, walk-in shower and separate soaking tub with skylight overhead. An oversized guest bedroom with an adjacent full bathroom completes the second floor. The finished lower level offers flexibility with an additional bedroom, full bathroom and a separate office/den area. Additional highlights include a 2-car attached garage, mudroom area, 20’ grand foyer entry, central air, recessed lighting throughout and access to the association's fitness center. Ideally located near an abundance of shopping/restaurants at Chestnut Hill Square/Wegmans, The Shops at Chestnut Hill, The Street and just steps from Lifetime Fitness and the trails of Lost Pond Reservation, this exceptional residence offers effortless suburban living just minutes from Boston.

344 Boylston Street Unit A, Newton

Listing courtesy of Listing Agent: Neda Vander Stoep from Listing Office: Coldwell Banker Realty - Boston.
$3,995,000
4 Beds ⋅ 5 Baths ⋅ 73573585 MLS
Welcome to this stunning center-entrance Colonial in Brookline's Chestnut Hill estate area, set on a level half-acre lot. This expansive home features 4+ bedrooms, 4 full and 1 half baths & offers over 4,895 square feet across three finished levels. The foyer opens to a fireplaced living room and a formal dining room that seats 12. The Chef’s kitchen features a Wolf range, Sub-Zero refrigerator, double wall ovens including steam, Cove dishwashers, two sinks, custom cabinetry & granite counters. A library with built-ins cabinetry sits off the dining room & kithcen. The family room, with gas fireplace opens through French doors to a bluestone patio and a broad, fenced, level yard. Upstairs, the primary suite includes a private balcony, Carrara marble bath, dressing area, and two walk-in closets. Three additional bedrooms and two full baths & laundry complete the floor. The lower level consists of a media/playroom, gym, wet bar, beautiful full bath with glass enclosed shower + another set of laundry. Central air & Sonos throughout, EV charging & 2-car garage. Close proximity to the D Line at Chestnut Hill, shops and restaurants at The Street at Chestnut Hill, Soule Playground, and Dane Park.

17 Glenoe Rd, Brookline

Listing courtesy of Listing Agent: Jamie Genser from Listing Office: Coldwell Banker Realty - Brookline.
$3,100,000
5 Beds ⋅ 5 Baths ⋅ 73573502 MLS
A rare combination of character, space, and setting in Chestnut Hill, this beautifully maintained Cape sits on a scenic half-acre with approximately 3,900 SF, 5 bedrooms, and 4.5 baths. Enter into a home filled with classic period details, wide-plank floors, and abundant south-facing light. The gracious living room welcomes with a fireplace and French doors opening to the patio, while the spacious family room features custom built-ins. At the heart of the home, an updated eat-in kitchen flows into a comfortable sitting area and opens directly to the backyard. A convenient mudroom leads to the driveway and two-car garage.Upstairs, the sun-filled primary suite offers an en-suite bath and private balcony, joined by four additional bedrooms, including a second primary, a study, and three full baths. Private guest quarters with separate stair access add flexibility. The lower level offers laundry, recreation space, and storage. Step outside to discover a pool surrounded by mature landscaping, a spacious patio, and peaceful grounds that create a private oasis.Set along beautiful Woodland Road, a leafy, tree-lined neighborhood with a welcoming community atmosphere, the setting is ideal for walking and running beneath towering oaks and mature trees. Dane Park, a wooded town park with trails, is within walking distance, while Wegmans, The Shoppes at Chestnut Hill, SuperLux, and an array of shops and restaurants are just minutes away. Convenient access to major routes also makes commuting easy, including a direct surface-road connection to Cambridge. With its distinctive character, generous scale, flexible layout, and exceptional outdoor setting, this is a property that truly needs to be experienced in person.

284 Woodland Road, Brookline

Listing courtesy of Listing Agent: The Denman Group from Listing Office: eXp Realty LLC.
$2,765,000
5 Beds ⋅ 4 Baths ⋅ 73572599 MLS
Come fall in love with this storybook 5-bed, 3.5-bath Colonial Revival set on 0.3AC in Brookline’s Chestnut Hill. Built in 1926, this charming 4,028SF residence offers a layout tailored for modern living. Streaming southern sunshine, timeless architecture, 3 fireplaces, and oversized windows define the home. Welcoming entry connects the main living spaces. Gracious living room w/ fireplace and built-ins flows into bright conversatory. Opposite is a family room with fireplace, which opens to a bright dining room. Classic butler’s pantry connects to the kitchen. With ample counter space and a cozy eat-in area, the kitchen serves as the heart of the home with direct access to deck and yard. Mudroom and half bath complete floor. Upstairs has bright en-suite primary, 4 additional bedrooms, office, and 2 full baths. Walkout lower level with playroom and laundry. Attached garage. Landscaped grounds create a true sense of privacy. Close to “The Street”, top schools, and Green D line train.

401 Heath Street, Brookline

Listing courtesy of Listing Agent: Hilary Maddox Team from Listing Office: Compass.
$1,790,000
4 Beds ⋅ 3 Baths ⋅ 73572511 MLS
Captivating colonial tastefully designed for elegant entertaining and comfort in mind. Privacy + nature abound in this 4 bedrooms, 3 bathrooms + 2450 square feet of refined living space in a premier Chestnut Hill location. Near Baker Elementary school (grades K-8) + close proximity to Putterham Shops, tennis, golf, wildlife sanctuary, Longwood Medical Area, Arnold Arboretum + Jamaica Pond. First floor has living room with wood burning fireplace, family room, bedroom with full bath + access to expansive outdoor deck. In the heart of the residence is a beautifully renovated kitchen with custom white shaker cabinets, sleek black granite countertops, stainless steel appliances + generous center island. Upper level has a sprawling primary bedroom suite complimented by majestic sunset views + an abundance of attributes such as walk-in closet, separate sitting area + spa-like bath with dual sink vanity, glass enclosed shower + soaking tub/jacuzzi. Additional finished lower level provides versatile space for a fitness gym, home theatre or home office to meet today's evolving lifestyle needs. One car garage, one carport + plenty of additional driveway parking make this an ideal residence to call home.

133 Wolcott Road, Brookline

Listing courtesy of Listing Agent: Mary Lochner from Listing Office: Coldwell Banker Realty - Brookline.
$2,395,000
4 Beds ⋅ 5 Baths ⋅ 73569446 MLS
Set along one of Chestnut Hill’s picturesque tree-lined streets, this handsome brick Tudor offers a thoughtful blend of classic architecture, generous proportions & comfortable everyday living. A welcoming foyer introduces elegant living & dining rooms with hardwood floors & distinctive period details, while the spacious eat-in kitchen, with abundant cabinetry, updated appliances & wet bar, opens naturally to a relaxed family room with direct access to the backyard. Upstairs, four well-proportioned bedrooms include a generous primary suite overlooking the backyard, complete with a sizable walk-in closet & ensuite bath. A second ensuite bedroom, along with two additional bedrooms, provides flexibility for family, guests or a home office. The lower level offers versatile space for recreation, hobbies, storage or future expansion, with convenient access to the garage. Outdoors, a tiered backyard creates a private setting with a pool, deck & lawn, offering multiple spaces for entertaining, relaxing & enjoying the warmer months. Fresh paint, new and refreshed flooring & an updated back deck enhance the home’s appeal while preserving its distinctive character. Ideally situated in the Baker School District, with easy access to Route 9, shopping, dining & the amenities of Chestnut Hill, this is a home with both an inviting sense of place & room to make it your own.

72 Beverly Rd, Brookline

Listing courtesy of Listing Agent: Ovesen Group from Listing Office: Coldwell Banker Realty - Brookline.
$3,999,999
6 Beds ⋅ 6 Baths ⋅ 73568425 MLS
Tucked at the end of a desirable cul-de-sac in Chestnut Hill, this classic shingle-style residence offers four beautifully finished levels of living with a timeless traditional design. Hardwood floors, gracious room proportions, and a warm, inviting floor plan create a home equally suited for everyday living and entertaining.Featuring 6 bedrooms and 6 full bathrooms, the residence offers exceptional flexibility for family, guests, home offices, and additional living spaces. The finished walk-out lower level adds another dimension of usable space with direct access outdoors, while the three-car garage provides both convenience and ample storage.Beautifully landscaped grounds enhance the home’s curb appeal and sense of privacy, with the property set on approximately 25,000 square feet of land. Combining substantial living space, classic New England architecture, and a sought-after Chestnut Hill cul-de-sac location, this is a special opportunity to enjoy comfort, scale, and timeless character.

31 Kesseler Way, Newton

Listing courtesy of Listing Agent: Samantha Stumpo from Listing Office: Serhant.
$1,995,000
4 Beds ⋅ 3 Baths ⋅ 73549795 MLS
Fantastic move-in-ready 4 bedroom, 2.5 bathroom in Chestnut Hill. Set on a 15,000+ level private lot, LEAD FREE, perfect for INVESTOR or END USER, close to schools, shops, restaurants, public transportation, golf & Skyline Park with its trails, playgrounds, fields and other amenities. Filled with natural light, the main level has beautiful hardwoods, a fireplaced living room, lovely dining room, eat-in kitchen, family room, home office and guest bathroom. Upstairs are 4 very generous bedrooms. and a full hallway bathroom.The primary bedroom has vaulted ceilings, sky lights and, in addition to the large ensuite bathroom, a second separate dressing room with its own sink and vanity. The home's lower level has high ceilings and unlimited potential to be used as a gym, movie theatre or what ever your needs maybe. There is central a/c.The backyard is level and private, with an expansive deck off the kitchen and family room for entertaining. A 2 car garage and large driveway complete this offering

75 Hammond Pond Parkway, Brookline

Listing courtesy of Listing Agent: Amy Sassoon from Listing Office: Coldwell Banker Realty - Brookline.
$2,399,000
4 Beds ⋅ 3 Baths ⋅ 73547641 MLS
Prepare to be impressed by this beautifully renovated 4 Bed 3 Bath mid-century modern ranch in Chestnut Hill Brookline on the edge of the golf course! Set on over a half acre of beautiful landscaping surrounding the flat back yard lead to the golf course. Breathtaking renovations highlight modern living with soaring exposed beam ceilings, a dramatic living room with a wood-burning fireplace, and a wall of windows overlooking the screened porch, deck, and tranquil Japanese rock garden. The renovated kitchen features sleek cabinetry, updated countertops, appliances, a peninsula, pantry, and eat-in area. The main level offers three spacious bedrooms, including a large primary suite, while the finished walkout lower level includes a great room with kitchenette, fourth bedroom, full bath, studio, bonus room, patio access, and abundant storage. Perfect location with quick access to 9 & I-93 and a quick hop to local restaurants, shopping, Wegman's, and much more!

365 Newton St, Brookline

Listing courtesy of Listing Agent: Rose Hall from Listing Office: Blue Ocean Realty, LLC.
$2,899,900
4 Beds ⋅ 4 Baths ⋅ 73543931 MLS
An architectural masterpiece, this stunning custom-built contemporary home showcases modern design at its finest. Featuring soaring ceilings, an open-concept layout, and gallery-style lighting, the home is filled with natural light from expansive walls of windows offering breathtaking views. The gourmet kitchen is equipped with Miele appliances, perfect for both everyday living and entertaining. A fireplaced library on the main level provides a warm and inviting retreat. Enjoy spectacular sunsets from the sunroom or the private second-story balcony off the luxurious primary suite. The finished walk-out lower level offers exceptional additional space, featuring a dedicated gym area, a spacious game room, multiple bonus rooms that can be used as guest rooms, or office spaces, and abundant storage throughout. Step outside to a beautifully landscaped outdoor retreat with exterior stairs leading to a serene, courtyard garden, creating a peaceful setting for relaxation or entertaining.

28 Kesseler Way, Newton

Listing courtesy of Listing Agent: Xianbin Yin from Listing Office: Harmony Hill Realty LLC.
$2,199,000
4 Beds ⋅ 4 Baths ⋅ 73529380 MLS
Welcome home to this impeccably maintained 4BR English Tudor offering the perfect blend of historic charm and modern updates. Set back on a lush 0.43-acre lot, enjoy panoramic views of the Brookline Golf Course directly across the street. This property is entirely turn-key for today’s active family, featuring an expansive 12-room layout with soaring ceilings, a sunlit family room, and central A/C. Outdoor living shines with a classic screened porch and a private brick patio nestled in an oversized, professionally landscaped yard. Situated in a premier neighborhood steps from the acclaimed Baker School (K-8), local shopping at Putterham Circle, and an effortless commute to Longwood Medical Center and downtown Boston. Move right in and enjoy the quintessential Brookline lifestyle!

518 Newton St, Brookline

Listing courtesy of Listing Agent: Shi Earls from Listing Office: Winterspring Real Estate, LLC.
$8,200,000
6 Beds ⋅ 9 Baths ⋅ 73526856 MLS
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

Listing courtesy of Listing Agent: Maggie Gold Seelig from Listing Office: MGS Group Real Estate LTD.
$4,495,000
5 Beds ⋅ 8 Baths ⋅ 73524035 MLS
A custom-designed home showcasing exceptional craftsmanship, and a seamless blend of luxury living & grand-scale entertaining. Dramatic floor-to-ceiling windows bathe the interiors in natural light, while soaring 10+ foot ceilings and a versatile floor plan create an extraordinary living experience throughout. At the heart of the home is a spectacular chef’s kitchen featuring custom Sapele wood cabinetry, striking Onyx countertops, and top-of-the-line Miele appliances. The expansive living & family rooms each feature sleek linear gas fireplaces, offering both sophistication & comfort. The lavish primary suite is a private retreat, complete with dual spa-inspired bathrooms — one featuring a steam room & the other a soaking tub, along with two walk-in closets & direct access to an oversized deck. Additional highlights include four generous bedrooms, a gym w/full bath & sauna, 2nd family room & an elevator. Enjoy the stunning landscaped yard w/salt water pool & cabana, a heated driveway.

17 Edge Hill Rd, Newton

Listing courtesy of Listing Agent: The Kennedy Lynch Team from Listing Office: Hammond Residential Real Estate.
$4,998,500
4 Beds ⋅ 5 Baths ⋅ 73520842 MLS
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 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

9 Singletree Rd, Brookline

Listing courtesy of Listing Agent: Deborah M. Gordon from Listing Office: Coldwell Banker Realty - Brookline.
$6,400,000
4 Beds ⋅ 5 Baths ⋅ 73500458 MLS
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

Listing courtesy of Listing Agent: Tracy Campion from Listing Office: Campion & Company Fine Homes Real Estate.
$3,399,000
7 Beds ⋅ 7 Baths ⋅ 73494324 MLS
Location ! Location! Location! This stunning Colonial effortlessly blends timeless architecture w/ modern luxury, offering exceptional living space.Main level showcases a gracious family room w/ beamed ceilings & a fireplace, a chef’s kitchen w/ a butler’s pantry & a sun-drenched breakfast area that opens to a patio & a professionally landscaped, fenced-in backyard ideal for indoor-outdoor entertaining. A formal living room, dining room, ensuite bedroom, powder room & a mudroom w/ direct access to a 2 car garage complete this level. 2nd floor the expansive primary suite features a spa-like bathroom, a walk-in closet & a serene sitting area/ office. Spacious bedrooms w/ en suite baths & a well-designed Jack& Jill bath. Lower level adds exceptional versatility with a gym, wet bar, playroom, bedroom suite, & abundant storage ideal for multigenerational living. New 2026 Boiler installed. Bonus attic offers additional space potential for expansion/customization. A true gem in desirable area

22 Scotney Road, Newton

Listing courtesy of Listing Agent: Esin Susol Team from Listing Office: William Raveis R. E. & Home Services.
$8,995,000
6 Beds ⋅ 7 Baths ⋅ 73479457 MLS
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

Listing courtesy of Listing Agent: The Kennedy Lynch Team from Listing Office: Hammond Residential Real Estate.
$9,985,000
5 Beds ⋅ 8 Baths ⋅ 73478330 MLS
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

Listing courtesy of Listing Agent: Maggie Gold Seelig from Listing Office: MGS Group Real Estate LTD.
$5,627,000
9 Beds ⋅ 6 Baths ⋅ 73469901 MLS
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

Listing courtesy of Listing Agent: Michael Harper from Listing Office: Coldwell Banker Realty - Boston.
$16,980,000
7 Beds ⋅ 11 Baths ⋅ 73445544 MLS
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

Listing courtesy of Listing Agent: Tracy Campion from Listing Office: Campion & Company Fine Homes Real Estate.

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