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$2,950,000
5 Beds 6 Baths 73575300 MLS ['261 Tappan Street Condominium'] BLDG.
Grand townhome residence in the heart of Brookline’s sought-after Washington Square neighborhood, offering an impressive sense of space, style, and privacy along a picturesque, tree-lined street. Built in 2024, this stunning home spans four levels and features 5+ bedrooms, 5.5 bathrooms, beautiful white oak floors, soaring ceilings, abundant natural light, and a chef’s kitchen with designer finishes throughout. The expansive and versatile layout provides exceptional flexibility for everyday living, entertaining, guests, and working from home. Outdoor living is equally impressive, with three private decks, a patio, and yard offering multiple spaces to dine, entertain, or unwind. An attached garage with a 240V outlet for EV charging adds convenience and functionality. Just moments from top-rated schools, Washington Square’s acclaimed restaurants and boutiques, parks, and public transportation, this remarkable residence combines the space and privacy of a single-family home with the ease of townhome living in one of Brookline’s most desirable neighborhoods.

261 Tappan St Unit 1, Brookline

Listing courtesy of Listing Agent: Matt Palmer from Listing Office: Summit Residential.

$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.

$4,500,000
5 Beds 6 Baths 73572602 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 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.

$2,175,000
5 Beds 4 Baths 73571974 MLS
Gracious brick home in Brookline’s coveted Corey Hill neighborhood, freshly painted throughout with newly refinished hardwood floors. Abundant natural light and timeless architectural details create a warm and inviting backdrop for everyday living and entertaining. Generous living and dining rooms, a handsome fireplace, spacious bedrooms, a flexible floor plan, and an oversized attached garage offer exceptional comfort and versatility. Enjoy sweeping views of the Boston skyline and an exceptional location near Summit Park, with convenient access to the T, Coolidge Corner, and Brookline Village. Ideally located near the Longwood Medical Area and Boston’s renowned universities and hospitals. A rare opportunity to own a distinctive home in one of Brookline’s most sought-after neighborhoods.

77 Jordan Rd, Brookline

Listing courtesy of Listing Agent: Allison Blank from Listing Office: Compass.

$3,095,000
5 Beds 3 Baths 73570606 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.

$6,800
5 Beds 4 Baths 73568422 MLS
Fully gutted stunning single-family for rent in Chestnut Hill. This rare-find house features a brand-new open kitchen design,beautiful hardwood floors, quartz countertops, stainless steel appliances, and stunning bathrooms. The whole first floor iscompletely open, 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 within walking distance to Baker Elementary School, shops, the library, and localamenities. Pack your stuff and move in today.

303 Russett, Brookline

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

$4,900
5 Beds 2 Baths 73564222 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, and pet friendly! Available 9/1.

76 Babcock Street Unit 3, Brookline

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

$4,995
5 Beds 2 Baths 73559767 MLS
Available Sep 1. 5 bedrooms penthouse w/ 1,500 sf living space. This unit features stainless steel kitchen with honed black granite countertops,dishwasher, disposal, large double door fridge, gas range, lots of counter and cabinet space, beautiful bamboo floors, 2 full baths,master bedroom, Jacuzzi, decorative fireplace, large porch gets lots of sun (the perks of being on the top floor!), views of the Prudential from the front of the unit. Coin-op laundry in building. HEAT AND HOT WATER INCLUDED IN THE RENT. It is literally steps away from the C-line, and D-line stop and shop and Trader Joe's, shopping, bars, restaurants, park, and many other conveniences. Easy access to the green line train station.

156 Harvard St Unit 8, Brookline

Listing courtesy of Listing Agent: David-Daili Xiao from Listing Office: Engel & Volkers Newton.

$799,000
5 Beds 2 Baths 73557434 MLS ['16 Garrison Condominium Trust'] BLDG.
NEW PRICE - $799,000! A compelling investment opportunity in the heart of Brookline’s Washington Square. Tenants are in place through 8/31/27 at $5,530/month, generating $66,360 in annual rental income and an approx. 6% cap rate. This spacious 5-bedroom, 2-bath condo features a renovated open-concept kitchen with granite countertops, stainless steel appliances and plenty of cabinetry, along with two updated bathrooms, including one with a walk-in shower. Hardwood floors, generously sized bedrooms, in-unit laundry and bike storage add to the appeal. The professionally managed 8-unit association has completed several major improvements, including a new roof in 2020 and boiler replacement in 2016. Located on a quiet, tree-lined side street just steps from Washington Square’s restaurants, cafés, shops, Star Market and parks, with Coolidge Corner and Cleveland Circle nearby. The Green Line and bus routes are less than a quarter mile away, with easy access to Longwood Medical Area, downtown Boston and area universities. Strong rental income, a lease already in place, and a prime Brookline location make this one worth a closer look. Some photos are virtually staged.

16 Garrison Road Unit 7A, Brookline

Listing courtesy of Listing Agent: Irina Spiegel from Listing Office: Coldwell Banker Realty - Brookline.

$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 and 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.

$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.

$2,700,000
5 Beds 4 Baths 73519268 MLS
Luxury upper-level duplex residence on a quiet one-way street in the heart of Washington Square, offering approximately 3,500 sq. ft. of thoughtfully designed living space. This elegant home features 5 bedrooms, 4 full bathrooms, and an open floor plan ideal for both everyday living and entertaining. The sun-filled living and dining area showcases a marble fireplace and opens to a spacious private deck with sweeping Boston skyline views. The chef's kitchen is equipped with premium appliances, including a Wolf range, a breakfast bar, and abundant workspace. The spacious primary suite features a private balcony, marble bath with an oversized Jacuzzi tub, radiant heated floors, and custom closets. A second ensuite bedroom also offers a private balcony, while additional bedrooms provide flexibility for guests, a home office, or family living. Additional highlights include four private outdoor decks and balconies, hardwood floors, central air, laundry on the 2nd floor, custom built-ins and closets, a built-in surround sound system, Nest thermostats, abundant natural light, and two outdoor parking spaces. An elevator provides convenient access from the parking area to the main entrance. Ideally located just moments from Washington Square's restaurants, cafés, shops, the MBTA Green Line (C Branch), and the Driscoll School, this exceptional residence offers a rare combination of luxury, space, and convenience in one of Brookline's most desirable neighborhoods.

91 University Rd Unit 2, Brookline

Listing courtesy of Listing Agent: Yukiko Oyama-Morris from Listing Office: Oyama Investments, Ltd..

$3,495,000
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 seasonal 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.

$3,545,000
5 Beds 5 Baths 73516646 MLS
Spectacular single-family alternative. This side-by-side Contemporary Luxury townhouse, newly constructed in 2017, features all the luxury you would expect. Sprawling living room and dining. The eat-in kitchen has custom cabinetry, Thermador appliances, and marble countertops. The kitchen has direct access to the large private/exclusive backyard, which spans two levels. There is a large patio and garden. There are 5 bedrooms and 4.5 baths. Large Primary has cathedral ceilings and an ensuite, featuring a double shower, double vanity, soaking tub, and radiant floor heating. Adjoining the primary is a large family/sitting room with sliders to the patio overlooking the back garden. There is a finished lower level with a large family room and a large bedroom, both with glass sliders for direct outdoor access. There is a convenient kitchenette as well. Playground directly across. Minutes to school, shopping, restaurants, and T. Convenient to Longwood Medical and Boston. 92 Walk Score.

90 Columbia Unit U90, Brookline

Listing courtesy of Listing Agent: Sheila White from Listing Office: Compass.

$3,545,000
5 Beds 5 Baths 73508728 MLS
Spectacular single-family alternative. This side-by-side Contemporary Luxury townhouse, newly constructed in 2017, features all the luxury you would expect. Sprawling living room and dining. The eat-in kitchen has custom cabinetry, Thermador appliances, and marble countertops. The kitchen has direct access to the large private/exclusive backyard, which spans two levels. There is a large patio and garden. There are 5 bedrooms and 4.5 baths. Large Primary has cathedral ceilings and an ensuite, featuring a double shower, double vanity, soaking tub, and radiant floor heating. Adjoining the primary is a large family/sitting room with sliders to the patio overlooking the back garden. There is a finished lower level with a large family room and a large bedroom, both with glass sliders for direct outdoor access. There is a convenient kitchenette as well. Playground directly across. Minutes to school, shopping, restaurants, and T. Convenient to Longwood Medical and Boston. 92 Walk Score.

90 Columbia Unit U90, Brookline

Listing courtesy of Listing Agent: Sheila White from Listing Office: Compass.

$1,710,000
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.

$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.

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