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$9,200
5 Beds 3 Baths 73554562 MLS
Available 9/1 or a few days earlier - Absolute dream find in Brookline with back yard oasis! This 5 bedroom 3 bath single family home has been thoughtfully renovated with a stunning (and kosher) eat in kitchen that overlooks a beautiful and large back yard/patio. The first floor also contains a full bath, family foyer (mud room), in unit laundry, formal dining room and large living room. Upstairs are 5 bedrooms, including a large primary with en suite bath and walk in closet. Off street parking includes one garage space and the double wide drive, for a total of 3 possible parking spaces. Central AC and Heating. Can be rented partially furnished or not. Located in a sought-after Brookline neighborhood w/in walking distance to Coolidge Corner, Washington Sq, MBTA Green Line, hospitals, universities, & more!

268 Mason Terrace, Brookline

Listing courtesy of Listing Agent: Jonathan Finlay from Listing Office: Longwood Residential, LLC.

$2,750,000
5 Beds 6 Baths 73550700 MLS
This pristine, move-in ready residence offers the best of Brookline with easy access to transit, parks, restaurants, shopping, universities, museums, and the Longwood Medical Area. In the heart of Corey Hill, Coolidge Corner, and Washington Square this property was expertly transformed in 2016 from a multifamily into a stunning multilevel single-family home. The home showcases exceptional craftsmanship and thoughtful design throughout. Oak floors throughout, custom built-ins, two gas fireplaces, and an open-concept kitchen with upgraded appliances, double oven, create inviting spaces for everyday living and entertaining. Every bedroom features an ensuite bath, while two kitchenette areas and a walkout lower-level suite offer exceptional flexibility for multigenerational living, guests, or work-from-home needs. A spacious deck, low-maintenance lot, and two-car garage complete this remarkable home.

16 York Ter, Brookline

Listing courtesy of Listing Agent: Wendy Rocca from Listing Office: Keller Williams Realty Boston Northwest.

$4,495,000
5 Beds 5 Baths 73550033 MLS
SARGENT ESTATES! Privately set on approximately 1 acre in Brookline's coveted neighborhood, this exceptional contemporary residence offers over 6,800 square feet of light-filled living space surrounded by mature trees & natural beauty. A winding drive leads to this 5+ bedroom, 4.5-bath home featuring soaring ceilings, expansive walls of glass & seamless indoor-outdoor living. The custom kitchen opens to an impressive 720-square-foot living and dining room with fireplace & dramatic ceilings, flowing to an expansive deck overlooking the tranquil grounds & swimming pool. The first floor also includes 2 bedrooms, 2 full baths & a half bath. Upstairs, the private primary suite offers an updated bath, walk-in closet, office, sitting room & oversized deck. The walk-out lower level features a large recreation room, playroom, exercise room, 2 bedrooms an office & a full bath. A two-car garage completes this remarkable property just minutes from schools, shops, hospitals & downtown Boston.

108 Codman Rd, Brookline

Listing courtesy of Listing Agent: Jamie Genser from Listing Office: Coldwell Banker Realty - Brookline.

$6,000
5 Beds 2 Baths 73549744 MLS
Available 9/1 or 1 week earlier - Amazing opportunit to rent this fully renovated, 5+ bedroom, 2 full bath condo with 2,468 sq. ft. of living space on the 2nd and 3rd floor in Brookline Village. In addition to 5 spacious bedrooms this home includes 2 bonus rooms ideal for a home office, gym or playroom. The private entrance leads you up to a spacious sun-filled living room, separate dining room, and renovated kitchen with granite countertops, stainless steel appliances, gas stove and dishwasher. The 2nd floor also includes 2 large bedrooms, in-unit laundry, a full bath and balcony. The 3rd floor contains three large bedrooms, full bath and 2 bonus rooms. Additional highlights include 4 parking spaces (one garage), and a large patio shared with the 1st floor. Situated in the heart of Brookline Village, this home is just moments from Brookline High School, Longwood Medical Area, Green Line T stations, shops, restaurants, parks, and many of Brookline's top schools. Easy commute to Boston!

30 Cypress Unit 2, Brookline

Listing courtesy of Listing Agent: Jonathan Finlay from Listing Office: Longwood Residential, LLC.

$5,000
5 Beds 2 Baths 73544386 MLS
Spacious top-floor 5-bedroom apartment in the heart of Coolidge Corner! This beautiful unit features five generously sized bedrooms with ample closet and storage space, soaring ceilings, and abundant natural light throughout. The oversized eat-in kitchen offers extensive cabinet and pantry storage, making it ideal for everyday living. Heat and hot water are included, and common laundry is available in the building. Conveniently located just moments from local restaurants, cafés, grocery stores, and everyday conveniences, including Trader Joe's, Starbucks, and Dunkin'. Professionally managed, students are welcome, pets are negotiable, and the apartment is available 9/1.

76 Babcock Street Unit 3, Brookline

Listing courtesy of Listing Agent: Gretchen Devine from Listing Office: Berkshire Hathaway HomeServices Warren Residential.

$2,500,000
5 Beds 4 Baths 73535475 MLS
Set in the coveted estate area of Brookline, this residence offers a rare opportunity to create a truly spectacular home overlooking the serene beauty of the Brookline Reservoir. Rich in architectural character, the home is defined by its striking presence, graceful proportions, and an abundance of original detail. While the home requires renovation, it presents an exceptional canvas for customization. The scale, layout, and architectural integrity provide all the right elements to transform this property into a breathtaking home. The grand living room is a standout feature—anchored by impressive ceiling height, elegant lines, and significant hardwood floors that run throughout the home. Outside, the proximity to the reservoir offers not just picturesque views, but a lifestyle. Home is being sold as is. Buyer to do their own due diligence. 140 Dudley St, the adjacent home, is also for sale.

128 Dudley St, Brookline

Listing courtesy of Listing Agent: Deborah M. Gordon from Listing Office: Coldwell Banker Realty - Brookline.

$1,850,000
5 Beds 4 Baths 73527992 MLS
NO HOA fees.Unique corner townhouse-single family, offering four bedrooms across four sun-filled levels and a Private Patio. Wall-to-wall sliders open to composite decks, filling the home with natural light and showcasing panoramic treetop and sky views. Behind its classic brick exterior, discover a spacious interior with a true wow factor. The kitchen features stainless steel appliances, an induction range, French door refrigerator, and granite countertops. Custom built-ins and generous closets provide huge amount of storage, while Mitsubishi mini-split heat pumps in every room ensure year-round comfort. Lower-level bedrooms offer private walk-out access—ideal for guests or flexible living. Nestled on a picturesque, tree-lined street that blends historic charm with modern design, this home is steps away from the C & D Lines T, grocery stores and restaurants. Enjoy tranquility, style, and urban convenience in one of the area’s most sought-after neighborhood!

184 Rawson Rd Unit 184, Brookline

Listing courtesy of Listing Agent: Azeddine Fadli from Listing Office: Property Navigator.

$2,749,999
5 Beds 6 Baths 73523918 MLS
Luxury Living in Chestnut Hill, Brookline. Spacious 5-bedroom home designed for extended families, aging parents, or long-term guests. Four bedrooms feature private en suite bathrooms, offering comfort and privacy throughout. Two bedrooms are conveniently located on the main level, while two upstairs bedrooms feature skylights filled with natural light. An additional lower-level bedroom creates flexible living options. Enjoy a warm family room with a fireplace, plus a finished lower level complete with a second fireplace, a kitchenette, and flexible space perfect for a family room, theater room, game room, or private guest retreat. Step outside to your private inground pool and enjoy peaceful surroundings near the renowned Brookline Golf Course. Complete with a 2-car garage and close proximity to Boston, medical centers, shopping, dining, and major routes, this home blends luxury, flexibility, convenience, and multigenerational living in the heart of Chestnut Hill.

171 Shaw Rd, Brookline

Listing courtesy of Listing Agent: Melvin A. Vieira Jr. from Listing Office: RE/MAX Real Estate Center.

$3,995,000
5 Beds 5 Baths 73517349 MLS
Handsomely poised overlooking the Brookline Reservoir and nestled back from the street, this distinguished period home offers four finished levels and serene water views on nearly a half-acre with bluestone patio and pool. The gracious entry opens into a grand foyer flanked by sun-drenched rooms. Bay windows in the living room, dining room, family room, and primary suite frame reservoir and garden views. Four fireplaces, high ceilings, crown molding, and custom woodwork throughout. Well-equipped kitchen for serious cooks with breakfast area and counter seating. Private first-floor study. Enchanting screened porch access the dining and living rooms for al fresco dining. Second floor: three bedrooms, two baths, and a primary suite with large dressing room, ensuite bath, and private deck. Third floor: two additional bedrooms and full bath. Lower level: exercise room, sauna, wine cellar and lav. Two-car garage. Minutes from Chestnut Hill shopping, Longwood Medical Area, and universities.

68 Dudley Street, Brookline

Listing courtesy of Listing Agent: Friedler / Marchant Living Group from Listing Office: Hammond Residential Real Estate.

$4,650,000
5 Beds 6 Baths 73516969 MLS
An artful balance of historic character & modern design, this 5,423SF 5BD, 5.5BA 1891 Colonial Revival was meticulously renovated in 2017 and is set on .41AC of landscaped grounds. Oversized windows, tall ceilings, bespoke millwork, detailed crown moldings, & 4 fireplaces highlight the home’s craftsmanship. Welcoming entry w/ FP connects main floor. Bright living room w/ FP and dining room w/ French doors that lead to wraparound deck. Renovated open kitchen w/ island, pantry, and eat-in. Adjoining family room w/ gas FP & built-ins. 1/2BA & mudroom complete level. Upstairs is the primary suite w/ FP, spa-like bath, & walk-in closet, en-suite bedroom, add’l bedroom, full bath, & laundry. Flexible 3rd floor flex w/ 3 add’l rooms & bathroom - ideal as bedrooms, offices, or play space. Walkout lower level w/ private entrance, en-suite bedroom, 2nd kitchen, family room, & storage. Private setting w/ tiered grounds, bluestone patio, & extensive lawn framed by mature trees & seasonal plantings

50 Sumner Road, Brookline

Listing courtesy of Listing Agent: Hilary Maddox Team from Listing Office: Compass.

$2,765,000
5 Beds 4 Baths 73516948 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.

$3,295,000
5 Beds 3 Baths 73508555 MLS
Set on .92AC in Brookline’s Estate area, this 5BD, 3BA home was ahead of its time. Built in 1850 as the carriage barn of the Old Greenhill Estate, it was converted to a single-family and extensively reimagined with open living spaces, expansive glass, and a strong connection to the landscape. 2,834SF home enjoys southwest light throughout, with long sight lines to the outdoors & rooms that feel distinct yet flow naturally together. Oversized windows & glass doors open to backyard. Kitchen connects to the dining area w/ fireplace, while a family room with built-ins & a vaulted living room with 2nd fireplace offer flexible gathering spaces. 2 main-level bedrooms and a full bath add versatility. 2nd floor offers primary suite w/ treetop views and en-suite bath. 2 add’l bedrooms, full bath, and laundry complete 2nd floor. LL w/ mudroom, storage, & access to 2-car garage. Outside, mature trees, open lawns, seasonal gardens, and privacy create a rare setting just minutes from Boston.

185 Warren Street, Brookline

Listing courtesy of Listing Agent: Hilary Maddox Team from Listing Office: Compass.

$4,250,000
5 Beds 5 Baths 73504708 MLS
Beautifully restored 1900s French-style residence on an acre of land in Brookline’s coveted Fisher Hill. Over 6,000 sq ft of living space featuring 5 bedrooms and 4.5 bathrooms. Inviting foyer with fireplace & custom bookshelves, an impressive great room with 15’ ceilings & fireplace, an elegant living room with period details including a fireplace, and a dining room with French doors to a stone terrace. House features a chef’s kitchen with high-end appliances and two spacious first-floor primary suites offering serene terrace views. The second floor has two bedrooms and a full bathroom. There is also a fifth bedroom with a private entrance, perfect for au pair or in-law. Four fireplaces, stone terraces, sweeping lawns, and lush landscaping complete this exceptional property, close to Brookline Reservoir, Chestnut Hill shops, Green Line public transportation, major highways & Boston.

540 Chestnut Hill Ave, Brookline

Listing courtesy of Listing Agent: The Duffy Group from Listing Office: Compass.

$1,860,000
5 Beds 4 Baths 73492913 MLS
Fully gutted stunning single family for rent in Chestnut Hill. This rare find house features brand new open kitchen design,beautiful hardwood floors, quartz countertop, stainless steel appliances, stunning bathrooms. The whole first floor iscompletely opened, with one study room and an office. The lower level is fully finished with a wet bar, one full bathroom,with its own entrance in the back, which can be used as a perfect in-law suite. The second floor has three bedrooms and twofull bathrooms. Master bedroom has its own master bathroom with a shower room and a soaking tub. Walk to the thirdfloor, it serves as an additional living area with lots of storage rooms.The house system is brand-new installed in 2019,with central A/C and heating.This house is walking distance to Baker Elementary School, shops, the Library and localamenities. Photos shown was the staging last year.

303 Russett Road, Brookline

Listing courtesy of Listing Agent: Zhou Chen from Listing Office: Blue Ocean Realty, LLC.

$2,698,000
5 Beds 4 Baths 73492578 MLS
This classic brick Colonial, set on one of Brookline’s most coveted streets near the Brookline Reservoir, offers stunning views and exceptional spaces for both family living and entertaining. This 5-bedroom, 3.5-bath home features a front-to-back living room with a gas fireplace, a gracious dining room with its own fireplace, and an eat-in kitchen that opens to a covered deck and patio—perfect for entertaining. The main level also includes a private home office, a powder room, and a sun-filled, oversized family room with direct access to a second patio. Upstairs on the 2nd and 3rd levels are five bedrooms and an additional home office, including a spacious primary suite with an ensuite bath, walk-in closet, and private deck. The lower level offers a dedicated exercise area, laundry room, abundant storage, and an attached two-car garage. Ideally located near The Street, Wegmans, Longwood Medical Area, public transportation, and Boston.

140 Dudley St, Brookline

Listing courtesy of Listing Agent: Deborah M. Gordon from Listing Office: Coldwell Banker Realty - Brookline.

$12,000
5 Beds 4 Baths 73484867 MLS
close to the T, coffee shops, restaurants&shopping from a stunning renovated architectural gem on a private cul-de-sac on a premier Chestnut Hill St. Unobstructed Park views from luxury outdoor kitchen Bluestone patio with 8" outdoor gas fireplace, indoor sauna, home gym,Wine Cellar, Billiards room, paneled Library, luxury details, modern systems and heated driveway.Open1st floor features entertainment space, and radiant living room spans the depth of the house boasting a huge fireplace and beautiful moldings.Sunroom with 3 exposures opens onto side patio while the large dining room's bay windows, wood burning fireplace, and original paneling are serviced by an astonishing Chef's kitchen featuring custom cabinetry and top line appliances.The 2nd floor's expansive master suite boasts a walk in closet, marble bathroom w/gas fireplace.Two more large bedrooms, full bathroom, office and laundry room.3rd floor holds a media room, 2 additional bedrooms, playroom.This home has it all!

460 A Heath Street, Brookline

Listing courtesy of Listing Agent: Samantha Stumpo from Listing Office: Serhant.

$3,390,000
5 Beds 4 Baths 73484859 MLS
Ideally situated on a private cul-de-sac in Chestnut Hill, this stunning architectural gem offers timeless elegance & modern luxury. Just minutes to the T, restaurants, coffee shops, & shopping, it boasts unobstructed park views from a Bluestone patio with a luxury outdoor kitchen and 8' gas fireplace perfect for entertaining. Inside, enjoy a sauna, home gym, wine cellar, billiards room, & a richly paneled library.First floor offers a radiant living room with fireplace and detailed moldings, a sunroom with three exposures, & a formal dining room with bay windows, original paneling, and wood-burning fireplace.The chef’s kitchen impresses with custom cabinetry and top-of-the-line appliances. Upstairs, the expansive primary suite features a gas fireplace, walk-in closet, and marble bath.Two additional large bedrooms, full bath, office, and laundry complete the second level.The third floor includes a media room, two bedrooms, and a playroom.Heated driveway & luxury systems throughout.

460 Heath Street, Brookline

Listing courtesy of Listing Agent: Samantha Stumpo from Listing Office: Serhant.

$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.

$1,850,000
5 Beds 4 Baths 73477599 MLS
Condo Alternative! No HOA fees.Unique corner townhouse-single family, offering four bedrooms across four sun-filled levels and a Private Patio. Wall-to-wall sliders open to composite decks, filling the home with natural light and showcasing panoramic treetop and sky views. Behind its classic brick exterior, discover a spacious interior with a true wow factor. The kitchen features stainless steel appliances, an induction range, French door refrigerator, and granite countertops. Custom built-ins and generous closets provide huge amount of storage, while Mitsubishi mini-split heat pumps in every room ensure year-round comfort. Lower-level bedrooms offer private walk-out access—ideal for guests or flexible living. Nestled on a picturesque, tree-lined street that blends historic charm with modern design, this home is steps away from the C & D Lines T, grocery stores and restaurants. Enjoy tranquility, style, and urban convenience in one of the area’s most sought-after neighborhood!

184 Rawson Rd, Brookline

Listing courtesy of Listing Agent: Azeddine Fadli from Listing Office: Property Navigator.

$10,985,000
5 Beds 8 Baths 73466750 MLS
Elegant living meets modern style in this stunning light-filled 5+ bedroom Chestnut Hill residence. This property is in a class of its own, with graciously proportioned rooms, open layout and luxurious fixtures/finishes. Minutes to all Boston and Brookline offer, this entire property has been built to the highest standards by an esteemed local builder. The 1st floor features a gracious living/dining room, chef's kitchen with double island, family room, breakfast room, office, mudroom and 2 powder rooms. The 2nd floor has a spectacular primary suite (with spa-like bath and custom dressing room) and 4 additional ensuite bedrooms. The lower level has a recreation room and opportunity for a golf simulator/flex room, gym and wine room. There is a 3-car attached heated garage, full landscape/garden design, permit for a pool and ability to build a pool house/ADU, if desired. State-of-the-art systems like Lutron lighting and Sonos sound complete this masterpiece. Not to be missed!

222 Warren Street, Brookline

Listing courtesy of Listing Agent: Maggie Gold Seelig from Listing Office: MGS Group Real Estate LTD.

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