Brookline

Neighborhood Description

Brookline is a town in Norfolk County, Massachusetts and part of the Boston metropolitan area. Brookline borders six of Boston’s neighborhoods: Fenway, Allston, Brighton, Mission Hill, Jamaica Plain and West Roxbury. The city of Newton is to the West of Brookline. Brookline was incorporated in 1705, and now consists of over 20 distinct neighborhoods.

Coolidge Corner, Brookline Village and Washington Square are retail centers bustling with restaurants and stores. Brookline is easily accessible by car, located off the highway Route 9, and by public transportation with the MBTA green line and bus system. According to 2020 United States Census, the population of the town was 63,191.

Browse listings for sale in Brookline below. Contact Us with any questions or to schedule a tour for any listing below

Active Listings

$1,180,000 Active

50 Lancaster Ter 4 Brookline, Massachusetts

3 Beds 2 Baths 1,470 SqFt

This beautiful brick home on desirable Clinton Road, offers a well-maintained residence with many updates and newer systems.The first floor features a spacious living room with fire place, formal dining room, half bath and an eat-in kitchen appointed with a Thermador gas stove top and warming drawer, GE Monogram double oven, two Bosch dishwashers, two sinks & a Sub-Zero refrigerator. The kitchen opens to a sun-filled great room with doors conveniently located to a patio & a lush, private backyard. Also off the kitchen is another patio with a gas hookup for grilling. Upstairs are four generously sized bedrooms, including a primary suite with a newly-renovated en-suite bath and a shared full bath. The finished lower level offers flex spaces--exercise, den, office/play room, full bath, laundry area with a frig/freezer & garage acess. Close to Runkle School, Brookline High, the Chestnut Hill Reservoir, and C & D Green Line trolleys, with easy access to nearby shops, restaurants & Route 9.

$3,258,000 Active

52 Clinton Brookline, Massachusetts

4 Beds 4 Baths 3,265 SqFt 0.33 Acres

Gorgeous 2-bed, 2-bath PENTHOUSE w/private balcony and 2 garage spaces at Cypress Lofts! Enjoy abundant sunlight, high ceilings w/skylights and maple hardwood floors in the open layout living room and dining room. Newly updated kitchen features quartz counters, ample cabinetry, peninsula w/breakfast bar, and stainless steel appliances. Floor-to-ceiling glass sliding doors lead to a private balcony perfect for al fresco dining. Large primary bedroom suite offers treetop views, two closets (one is walk-in), and luxurious en suite bathroom. Second bedroom has an artfully curved wall w/huge windows that offer beautiful views and afternoon sun. Spa-like second bathroom, in-unit washer/dryer, central air conditioning. Cypress Lofts is one of Brookline’s premier luxury buildings, offering prof'l management, concierge, common room w/fireplace, elevator, guest parking, bike racks. Pet-friendly. Ideally located near Brookline Village, Emerson Park, schools, Green Line D-Train, Longwood Medical.

$1,299,999 Active

110-112 Cypress St PH3 Brookline, Massachusetts

2 Beds 2 Baths 1,246 SqFt

Unbeatable location! Enjoy effortless Coolidge Corner living in this beautifully refreshed 700 sq. ft. one-bedroom condo, complete with deeded garage parking and a private balcony. This well-maintained, pet-friendly building features elevators, laundry, and extra storage. Inside Unit 3A, Pergo engineered hardwood floors sweep through the spacious open living and dining areas—with plenty of space for a home office—and continue into the comfortable bedroom. Large windows and sliding glass doors onto the balcony fill the home with light. The tiled kitchen offers generous cabinet space. Enjoy a sparkling updated bathroom, 2025 wall AC, abundant closets, and fresh paint throughout. Your heat, hot water, water, and more are included in the HOA fee. Live just minutes from the C-line and Brookline's best restaurants and shops.

$619,000 Active

123 Sewall Ave 3A Brookline, Massachusetts

1 Beds 1 Baths 700 SqFt

Exquisite architectural details, bespoke finishes, and expansive one-level living distinguish this incredible 2,510 sq ft 4+ bedroom, four bath condominium with two garage parking spaces at Walnut Crossing, one of Brookline’s most coveted newer construction elevator buildings. Two units have been thoughtfully combined to make one exceptional signature residence with southern, eastern and northern exposures enhanced by soaring 9’ ceilings and custom windows imported from Italy. Show-stopping open-plan kitchen, dining and living space w/ quartz countertops, custom European cabinetry & Thermador appliances. Voluminous family room with a Juliet balcony. Four generously sized bedrooms, including two ensuite primaries with walk-in closets, plus a handsome office with luxe built-ins. Four elegant contemporary baths. A+ amenities including private storage, a gym, and a stunning shared roof deck. Premier location near Brookline Village, Longwood, Pill Hill & the Green Line. Truly rare.

$2,998,008 Active

69 Walnut St 4 Brookline, Massachusetts

4 Beds 4 Baths 2,510 SqFt

Exquisitely renovated 1876 townhouse showcasing top-of-the-line finishes in a prime Brookline location. Elegant entertaining spaces flow seamlessly into a stunning chef’s kitchen designed for both everyday living and sophisticated gatherings. An expansive deck overlooks a beautifully landscaped yard, creating the perfect backdrop for al fresco dining and outdoor enjoyment. A graceful staircase ascends to the second level, where a serene and luxurious primary suite awaits. The spa-inspired marble en suite bath features dual showers and a separate water closet. Adjacent to the primary bedroom is a library or home office with a fireplace, along with pocket doors leading to a dressing room and convenient laundry area. The skylit staircase continues to the third and top floor, offering three additional bedrooms and a full bath—providing flexibility. The lower level includes a half bath and a self-contained garden apartment with a private entrance. Rental Garage parking is available

$3,799,000 Active

57 Monmouth Brookline, Massachusetts

5 Beds 4 Baths 3,500 SqFt 0.08 Acres

Welcome to The Terraces, a private and elegant association nestled in the historic Beaconsfield neighborhood of Brookline. This two-bedroom, two-bathroom condominium offers generous room sizes, high ceilings, and updated kitchen and bathrooms. The primary bedroom includes an en-suite bath, and the large formal dining room provides flexibility - well suited as an elegant entertaining space or, as other owners have done, reimagined as an additional bedroom. Enjoy your coffee on the private covered porch, just off the kitchen. Conveniently located near the shops & restaurants of Washington Square and the MBTA Green Line (C & D).

$900,000 Active

321 Tappan St 3 Brookline, Massachusetts

2 Beds 2 Baths 1,243 SqFt

Ideally located in Washington Square on a beautiful side street, this lovely three bedroom condominium is perfect for an owner occupant or as an investment property. It is under a quarter mile to the Green Line, restaurants, shops and a grocery store. The professionally managed association includes 8 units with a 2020 roof and 2016 boiler.A well-outfitted foyer with a skylight welcomes you to the unit. It opens to a spacious living room with a bay of windows and exposed brick wall. Down the hall is the updated kitchen with another skylight, granite counters, stainless appliances and a nice-sized dining room. There are three large bedrooms, an updated full bathroom and walk-in closet with laundry. There is also a private storage room in the basement. This unit is a fantastic opportunity for an investor or owner occupant to acquire a well-maintained home in one of Brookline's most coveted and convenient neighborhoods. Extremely convenient to Longwood Medical Area & downtown Boston.

$899,000 Active

16 Garrison Rd 5 Brookline, Massachusetts

3 Beds 1 Baths 1,387 SqFt

Beautifully renovated, sun-filled two bedroom, two bathroom unit at desirable The Terraces in Washington Sq. The expansive foyer is flanked on the right by a gracious living room featuring a fireplace with marble surround.The spacious formal dining room has glass paned doors to the renovated eat-in kitchen with high-end granite countertops, glass backsplash, high-end appliances, and large pantry. A beautiful screened-in porch off the kitchen offers a serene space for al fresco dining. The primary bedroom has spacious closets and an elegant bathroom with large tiled shower, Carrera marble floor, and stackable washer and dryer. The second bedroom has a large closet. The remodeled second bathroom has a tub/shower, Carrera marble floor, and decorative marble tile. Assigned parking. Large windows, high ceilings, wood floors, and decorative molding throughout. Close to 'C' and 'D' Green line trains, supermarkets, and the numerous restaurants and coffee shops in Washington Square.

$1,099,000 Active

325 Tappan St 6 Brookline, Massachusetts

2 Beds 2 Baths 1,356 SqFt

Fantastic opportunity to own a spacious 2-bedroom, 2-bath condo with deeded off-street parking, ideally situated on a picturesque tree-lined street between vibrant Washington Square and the scenic Chestnut Hill Reservoir. The sun-filled open-concept living and dining area offers an inviting space for both everyday living and entertaining. The primary suite features a private full bath and three closets, while the second bedroom is generously sized with ample storage. Additional highlights include high ceilings, hardwood floors, a kitchen with gas cooking, IN-UNIT washer/dryer, and private basement storage. Enjoy unbeatable convenience just moments from shops, restaurants, and parks, with easy access to the MBTA Green Line (B, C, and D) for seamless commuting to Boston College, Boston University, the Longwood Medical Area, and downtown Boston.

$799,000 Active

38 Kilsyth Rd 21 Brookline, Massachusetts

2 Beds 2 Baths 987 SqFt

One of the premier one-bedroom residences in the historic Warwick Building, Unit 741 is among the largest by square footage, with a thoughtful layout maximizing space and privacy. Perched on a high floor in a coveted front corner position, the home showcases sweeping skyline views and exceptional natural light. The elegant and oversized living room impresses with high ceilings, classic molding and a ceiling fan. The kitchen offers ample cabinet and counter space plus room for eat-in dining. The generously sized bedroom comfortably accommodates a king-sized bed; the full bath includes a tub/shower combo. Freshly painted with recently buffed hardwood floors, storage is included. This is a pet friendly elevator building with a roof deck offering panoramic views, laundry facilities, gated garden area, bike storage and professional management. The Green line (C) stop is across the street. Such a convenient location to parks, markets, restaurants, shops and the Longwood Medical area!

$559,000 Active

1450-1454 Beacon 741 Brookline, Massachusetts

1 Beds 1 Baths 713 SqFt

Experience modern luxury wrapped in Victorian elegance on the coveted Naples Rd in the heart of Coolidge Corner! This charming 6 bed, 6.5 bath Victorian is just steps from the highly sought-after Devotion School and minutes to the Green Line, shops, restaurants, parks, and the Longwood Medical Area. Sun-filled interiors feature 9+ ft ceilings and an open layout throughout. First floor offers a spacious living room with fireplace, dining room, family room, and an amazing kitchen with top end Thermador appliances. Luxurious primary suite with dressing room and spa-like bath sits on the second floor along with two oversized bedrooms. Walk-out lower level includes en suite bedroom, rec room, and wet bar; third floor adds two bedrooms and loft. Beautifully landscaped yard and large driveway with 2-car garage offer even greater convenience. Rare opportunity for modern family living in a premier neighborhood in a top-tier school district!

$4,200,000 Active

36 Naples Rd Brookline, Massachusetts

6 Beds 7 Baths 6,266 SqFt 0.13 Acres

Rarely available 3BR/2BA top-floor condo in a stunning Gothic Revival residence on the National Registry of Historic Places. This 1,635 sq. ft. home was completely renovated in 2012, seamlessly blending historic character with modern luxury. Enjoy a bright, open layout featuring a quiet home office nook perfect for remote work, central AC, in-unit laundry, and basement storage. Step outside to your own private patio and fenced yard—a true urban oasis. This unit includes 2 dedicated parking spaces and is part of a boutique, owner-occupied 4-unit association. Unbeatable Location: Steps to C & D Green Lines and bus routes to Longwood Medical & Harvard. Walking distance to Pierce Elementary, Brookline High, and the vibrant shops/dining of Brookline Village, Washington Square, and Coolidge Corner. Pet-friendly and perfectly positioned for the best of Brookline living. Welcome home! Open Houses Saturday 4/18 & Sunday 4/19 from 12-2PM. Offers due Tuesday 4/21 by 12 noon.

$1,575,000 Active

447 Washington St 3 Brookline, Massachusetts

3 Beds 2 Baths 1,635 SqFt

Welcome to Longwood Towers. One of Brookline’s most sought-after full-service condo complex. This bright eight-floor 1-bed/1-bath renovated unit features gleaming wood floors throughout, contemporary kitchen with granite countertop & stainless appliances, comfortable bedroom, updated bathroom and in-unit W/D. Impressive amenities : grand lobby with 24/7 concierge & doorman, valet parking, fitness center & professional maintained grounds. Specious clubroom with full kitchen is ideal for casual use or private gatherings. Positioned between Longwood Medical Area & Coolidge Corner. Quick access on Green D Line to Fenway, Back Bay, Prudential Center, Midtown, Financial District and Amtrak station. Pet-friendly building welcomes two pets (under 40 lbs). Strong rental history makes this equally attractive to owner-occupants and investors.

$769,000 Active

20 Chapel St C807 Brookline, Massachusetts

1 Beds 1 Baths 815 SqFt

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.

$6,995,000 Active

198 Clyde Street Brookline, Massachusetts

4 Beds 5 Baths 6,521 SqFt 0.94 Acres

Great condo alternative!Located on a prime side street convenient to the Medical Area, Coolidge Corner, and the Village, this semi-attached, townhouse-style single-family home offers low-maintenance living and exceptional convenience. The inviting living room features a fireplace and custom built-ins and opens to a spacious dining room and an efficient kitchen with granite countertops and stainless steel appliances. This opens to a mahogany deck—ideal for al fresco dining—overlooking a private yard filled with three-season perennial plantings, a true gardener’s delight and peaceful retreat. The second floor includes a generous primary bedroom with a wall of closets, a second bedroom, and a full hallway bath. Oak hardwood floors run throughout the home. The lower level has laundry and direct access to garage, with workbench and storage. Well maintained and thoughtfully designed, this property is ideal for singles, small families, or empty nesters. Close to Lawrence School.

$1,375,000 Active

11 Kent Square 11 Brookline, Massachusetts

2 Beds 2 Baths 1,276 SqFt 0.06 Acres

This newly renovated 4-bedroom residence is perfectly located in Brookline, with balcony views overlooking your private pool, the Brookline Golf Course, and the Boston skyline.Designed for those who value privacy and elevated living, this home offers a rare blend of space, comfort, and presence—just moments from world-class hospitals and top-ranked schools.Set on over 16,000 sq ft of land with 4,585 sq ft of living space, the home features 4 en-suite bedrooms, an open-concept layout, two fireplaces, and a refined office nook.The finished lower level with kitchenette is ideal for entertaining or extended living, while the two-car garage with EV hookup adds modern convenience.

$2,998,000 Active

171 Shaw Rd Brookline, Massachusetts

4 Beds 6 Baths 4,585 SqFt 0.37 Acres

Stunning 8 rm brick Georgian Colonial has exceptional curb appeal, ideally located on a highly desirable street in Coolidge Corner, w/in Ridley School district. This sun-filled home has been thoughtfully updated, sits has on a corner lot with a charming yard enhanced by beautiful, mature plantings. Classic period details abound, including rich wood accents, coffered ceiling, and elegant dentil molding. The main level is well-suited for entertaining & features a cook’s kitchen, a graciously proportioned living room with a detailed fireplace, a dining room with direct access to a covered deck. A bright, heated sunroom provides flexible space for office or playroom. The second level offers an en suite primary bedroom with a deck, two additional bedrooms, full bath, another room for a nursery/office. The basement, with a high ceiling, has excellent potential. There is a walk-up attic. Superbly located near the “T,” parks, Coolidge Corner, the Longwood Medical, Charles River, and Cambridge.

$2,795,000 Active

108 Crowninshield Brookline, Massachusetts

3 Beds 2 Baths 2,069 SqFt 0.14 Acres

Bright and well-maintained 2-bed unit in the heart of Brookline’s desirable Coolidge Corner neighborhood. This charming Unit features an efficient layout, abundant natural light, and hardwood floors throughout. Updated kitchen with modern cabinetry and appliances, plus a clean, well-kept bath. Professionally managed building with elevator, laundry facilities, and secure entry. Enjoy unbeatable convenience with the Green Line (C branch) just outside your door, along with shops, restaurants, and cafes nearby. Ideal for owner-occupants or investors seeking a prime location with strong rental appeal. Don’t miss this opportunity to own in one of Brookline’s most sought-after areas!The lease ends on 6.30.2026 and rent is $3450.

$699,000 Active

1454 Beacon St 342 Brookline, Massachusetts

2 Beds 1 Baths 929 SqFt

Rare opportunity to own a beautifully updated penthouse studio in the heart of Coolidge Corner, just steps to everything. This bright and spacious home offers an open layout with new flooring, fresh paint, and abundant natural light. The eat-in kitchen is thoughtfully updated with new cabinetry, granite countertops, tile backsplash, and modern fixtures. The oversized bathroom features a full tub and excellent storage, complemented by three large closets and additional basement storage. Professionally managed brick building with strong owner occupancy. An exceptional value—ideal for first-time buyers or investors seeking a prime Brookline location with easy access to Longwood Medical, Fenway, and downtown Boston. Heat and hot water included in the condo fee.

$400,000 Active

75 Park Street 8 Brookline, Massachusetts

1 Baths 395 SqFt

Elegant brick center-entrance Colonial on a desirable tree-lined street, offering 10 rooms, 4–5 bedrooms, and 4.5 baths. Front-to-back living room with fireplace and great natural light, formal dining room, and eat-in kitchen open to a large family room. First-floor study/office. Central air. Two-car garage plus additional storage garage that accommodates a small car . The lower level includes a family room, workout room, and laundry. Located in the Heath School district, this home offers a private, quiet setting just minutes to schools, parks, shopping, and all that Brookline and Boston have to offer.

$3,200,000 Active

98 Spooner Road Brookline, Massachusetts

4 Beds 5 Baths 3,628 SqFt 0.23 Acres

Ideally located in the heart of Washington Square, this stunning four-unit brownstone blends classic Back Bay architecture with a complete down-to-the-studs renovation designed for modern living. Thoughtfully crafted by an award-winning architect, the residence showcases dramatic open-concept living, elevated by exceptional finishes and meticulous attention to detail. The home offers three bedrooms, two-and-a-half designer baths, and a sleek, state-of-the-art kitchen with custom cabinetry and top-tier appliances.Rich hardwood floors run throughout, while one parking space adds rare convenience. Just moments from Washington Square and Cleveland Circle with seamless access Longwood Medical, Downtown Boston and so much more!

$1,550,000 Active

1762 Beacon St 1 Brookline, Massachusetts

3 Beds 3 Baths 1,871 SqFt

Rare oversized 1-bedroom residence in the heart of Coolidge Corner offering an exceptional blend of scale, flow, and refined comfort rarely found at this price point. A gracious entry hallway opens to a sun-drenched living room and distinct dining area, creating a seamless layout ideal for both elevated entertaining and everyday living. The expansive bedroom offers outstanding proportions, flexibility, and excellent closet space. Eat-in kitchen with abundant cabinetry and generous workspace enhances both functionality and convenience, complemented by in-unit laundry. High ceilings, hardwood floors, and oversized windows fill the home with natural light throughout. Professionally managed, well-maintained building with strong owner occupancy. Unbeatable location just steps to premier dining, boutique shopping, parks, the Green Line, and top-rated schools, with effortless access to Longwood Medical Area and downtown Boston. Exceptional opportunity for end-users and investors alike.

$600,000 Active

116 Park Street 2 Brookline, Massachusetts

1 Beds 1 Baths 837 SqFt

Offers due 5pm Monday April 13.Set in the highly desirable Baker School neighborhood in the sought after Chestnut Hill/ S.Brookline area, this charming Colonial offers timeless character & exceptional potential. With inviting presence on a picturesque residential street, the home features sun filled interiors & functional layout ideal for modern living. The main level includes a bright living room, a well proportioned dining room & a spacious den or flexible space for everyday living or entertaining. The kitchen is practical & thoughtfully appointed. Upstairs, three generously sized bedrooms & a full bathroom offer comfortable living w/ ample natural light & storage. Additional highlights include a large backyard perfect for outdoor enjoyment or future expansion, shed, insulated windows & the home is de-leaded. Ideally located within Brookline, Chestnut Hill, West Roxbury and Jamaica Plain neighborhoods, with convenient access to Longwood Medical Area & Downtown.

$1,250,000 Active

87 Bonad Rd Brookline, Massachusetts

3 Beds 2 Baths 1,482 SqFt 0.11 Acres

Location, Location, Location! Sunny and bright 2-bedroom, 1 full and 1 half-bath condo in the heart of Coolidge Corner.This property features hardwood floors, 8-foot ceilings, an open floor plan, and a private balcony off the main bedroom. Additional amenities include laundry facilities in the building, central air conditioning, and extra storage. This elevator building is pet-friendly with some restrictions. Enjoy the close proximity to shops, restaurants, and the convenience of the C and D Green lines. Open House Saturday 11 April and Sunday 12 April, 1:00 to 3:00 pm.

$700,000 Active

55 Sewall 1C Brookline, Massachusetts

2 Beds 2 Baths 842 SqFt

Beautiful attached single-family townhouse on one of Brookline Village’s most coveted streets. Ideally located just minutes from Emerson Park, Pierce School, the library, and the Brookline Hills “T,” this home offers both charm and convenience. The tastefully updated eat-in kitchen featuring high-end appliances, custom cabinetry, and generous pantry, opens to a lovely rear porch perfect for relaxing or entertaining. Rich in character, the interior showcases high ceilings, elegant moldings, hardwood floors, and abundant natural light throughout. The main level includes a full dining room and spacious living room. The second floor offers three bedrooms, two full bathrooms, and in-unit laundry, while the third floor has one bedroom, office and ample storage. The basement, with its high ceiling, presents excellent potential for future finished space. Additional highlights include a welcoming front porch, a private backyard, a garage parking space, and additional outdoor parking space.

$2,395,000 Active

50 Waverly Street Brookline, Massachusetts

4 Beds 2 Baths 2,383 SqFt 0.14 Acres

Located on a prime side street convenient to the Medical Area, Coolidge Corner, and the Village, this semi-attached, townhouse-style single-family home offers low-maintenance living and exceptional convenience. The inviting living room features a fireplace and custom built-ins and opens to a spacious dining room and an efficient kitchen with granite countertops and stainless steel appliances. This opens to a mahogany deck—ideal for al fresco dining—overlooking a private yard filled with three-season perennial plantings, a true gardener’s delight and peaceful retreat. The second floor includes a generous primary bedroom with a wall of closets, a second bedroom, and a full hallway bath. Oak hardwood floors run throughout the home. The lower level has laundry and direct access to garage, with workbench and storage. Well maintained and thoughtfully designed, this property is ideal for singles, small families, or empty nesters. Close to Lawrence School and Longwood Playground/tennis courts.

$1,375,000 Active

11 Kent Square Brookline, Massachusetts

2 Beds 2 Baths 1,276 SqFt 0.06 Acres

Coolidge Corner meets Longwood Medical in one of Brookline’s most iconic full-service residences. Welcome to Longwood Towers, where historic grandeur & elevated living come together seamlessly. This 2 bed/2 bath renovated luxury home features a freshly painted & thoughtfully refreshed interior w/an open, light-filled layout, a great open-concept living space to meet & exceed. Chef-caliber kitchen w/granite counters & stainless appliances, in-unit W/D, Central A/C, gleaming wood floors, & tons of closet space. The building delivers at every level w/a showpiece grand lobby, 24-hour concierge, fitness center, clubroom, & prof maintained grounds. Unmatched convenience w/the Green Line (D) directly across the street, mins to Longwood Medical, & surrounded by Brookline’s best parks, shopping & fit for foodie dining. A rare opportunity to own in a building that defines both presence & lifestyle. Bright corner exposure & oversized windows flood the home w/natural light.

$1,175,000 Active

20 Chapel St B309 Brookline, Massachusetts

2 Beds 2 Baths 1,115 SqFt

Fantastic penthouse condo offering 808 square feet of well-designed living space with a great one-bedroom, one-bath layout and abundant natural light. A spacious bedroom, updated kitchen with granite countertops and new appliances, generous private extra storage, in-unit laundry, central a/c, ceiling fans and two-car parking (one assigned and one deeded) provide comfort and exceptional convenience. The condo is pet-friendly. This professionally managed community offers outstanding amenities including a fitness center, a cozy library, a board room, bike storage, on-site superintendent and beautifully landscaped park-like grounds. Ideally located near the Longwood Medical Area, the walking and running trails of Olmstead Park, and the charming shops and restaurants of Brookline Village, with easy access to the Green Line (T). This condo offers the perfect balance of tranquility and urban accessibility.

$665,000 Active

75 Glen Rd B5 Brookline, Massachusetts

1 Beds 1 Baths 808 SqFt

Make this beautiful one floor air conditioned unit with huge bright rooms and high ceilings your new home! Located in Sargent Estates, with beautiful grounds including outdoor in-ground pool and concierge. This beautiful three acre association surrounded by historic stone walls and beautiful old trees is just minutes from Longwood Medical Center, Brookline Village, and the Emerald Necklace. Just half a mile walk to the Brookline Hills D line stop, as well as gorgeous Jamaica Pond. It’s also just a hop and skip away from various eating establishments and a market. Enjoy your deeded garage parking spot plus plenty of guest parking. Association includes a sauna, and a huge community room with kitchen. The unit has beautiful wood floors and updated kitchen, ceilings over eight feet high, bath, lav, and plenty of closet space with custom shelving. The association is professionally managed yet low condo fees. Basement deeded storage.

$579,900 Active

22 Chestnut Place 210 Brookline, Massachusetts

1 Beds 2 Baths 828 SqFt 3.28 Acres

Welcome to this charming 3-bedroom, 2-bath home ideally situated in the heart of Brookline. Featuring a fully renovated kitchen and bathrooms, beautiful hardwood floors throughout, and an updated heating system, this home seamlessly blends timeless character with modern convenience. A versatile bonus room offers the perfect space for a fourth bedroom or home office. Just a few blocks from the Brookline Hills Green Line T station, commuting into downtown Boston is effortless, while nearby shops, restaurants, hospitals, and parks provide an exceptional neighborhood lifestyle. One of the home’s most unique features is its direct abutment to the highly regarded Lincoln School, offering rare proximity to one of the area’s top educational institutions. Set on a generous lot, the property features a large yard and a finished patio area ideal for grilling and entertaining. A truly convenient location in one of Boston’s most desirable communities. Best value in town!

$1,400,000 Active

428 Boylston St Brookline, Massachusetts

3 Beds 2 Baths 1,748 SqFt 0.13 Acres

Discover 39 Worthington Road in Brookline's coveted Cottage Farm neighborhood. This fully renovated masterpiece boasts 7 bedrooms and 5.5 bathrooms with impeccable craftsmanship and attention to detail. The interior, designed by a renowned interior designer has been featured in various publications. Wonderful spaces for entertaining and comfortable living include a large custom-designed chef's kitchen open to a gracious family room with custom millwork built-ins along with a large library with over 12' ceilings. There is a luxurious primary suite with a spa-like bath, walk-in closets, a sun-filled study, & access to a terrace. The lower level includes a gym, playroom, and more. Nestled on a double, extra-large expansive landscaped lot complete with a hockey rink (and equipment) and full outdoor kitchen, privacy and serenity, and indoor/outdoor living abound. The ideal setting and location that defines urban-suburban living close to all Boston/Cambridge/Brookline has to offer.

$8,995,000 Active

39 Worthington Rd Brookline, Massachusetts

7 Beds 6 Baths 7,080 SqFt 0.52 Acres

One of the most idyllic and coveted corner lots in Coolidge Corner, this 4 bed, 3.5 bath home was gut-renovated & designed with a focus on beauty, warmth, & sustainability to create a serene retreat. The expansive windows invite light into the home that offers southern, eastern & western exposure. The elegant foyer boasts soaring ceilings & marble flooring. A family room & office on the 1st floor open via French doors to the yard. A sweeping staircase, restored from the original home, leads to the heart of the residence: an open-plan living/dining area flooded with light. This space features a modern gas fireplace & sleek kitchen with custom cabinetry, stone island, & breakfast retreat. Mahogany decks invite seamless indoor-outdoor living. The spa-inspired primary suite boasts a sauna, glass shower, & Japanese Ofuro tub. 3 add’l bedrooms, modern baths, side-by-side parking, yard & advanced technologies—smart shades, Sonos, radiant heat, passive solar—complete this remarkable property.

$3,325,000 Active

102 Fuller St 2 Brookline, Massachusetts

4 Beds 4 Baths 3,345 SqFt

Excellent opportunity to purchase a spacious 2 bed 2 bath at 99 Pond Avenue at the Brook House for sale! Unit features large balcony, quiet serene views of courtyard. The unit comes Two car tandem garage parking # 316&A. The Brook House is a full service luxury building that has onsite management, 24/7 security, heated swimming pool, fully equipped health club with steam/sauna featuring cardio workout area, weight rooms, residents lounge with WIFI, outdoor barbecue areas, tennis and paddleball courts, basketball. Building is pet friendly. Walk/jog/bike/ paths at your door, steps to D and E “T” lines and many bus lines. Walk to Brookline Village, shopping, restaurants, Longwood medical community and many universities.

$725,000 Active

99 Pond Ave 222 Brookline, Massachusetts

2 Beds 2 Baths 1,300 SqFt

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.

$3,699,000 Active

71 Grove St Brookline, Massachusetts

5 Beds 5 Baths 5,068 SqFt 0.32 Acres

Luxury Brook House, Well maintained spacious, bright, modern studio with bonus deeded garage parking space #295 making your investment more valuable, Large sliding glass door encompassing one wall of living area, City views, Juliet balcony off of living area, Updated modern kitchen, Abundant closet space includes a large walk-in closet, 24/7 security/concierge, On-site management, Package delivery room, Enjoy a great lifestyle with top notch amenities: full scale fitness center with cardio/weight/exercise rooms, steam/sauna, heated outdoor swimming pool, tennis/pickleball/basketball courts, table tennis, resident lounge with wifi, herb garden and barbecue areas, C&D Green train lines and bus lines across the street, Close proximity to Brookline Village and Coolidge Corner with an array of many shops, restaurants and a movie theater, Convenient to Longwood Medical area and downtown Boston, Perfect for investors or first time buyers. *living area virtually staged.

$449,000 Active

44 Washington St. 605 Brookline, Massachusetts

1 Baths 500 SqFt

Welcome to the epitome of elegance-Chateauesque 1890's "Brookline Castle" has been gut renovated to its full grandeur!The one-of-a-kind exterior stonework is a rarity in Brookline. Open up to a gorgeous foyer, with rich woodworking & walnut hardwood floors throughout. The kitchen & dining area features oversized windows that flood the space with natural sunlight.The chefs kitchen boasts custom cabinetry, sparkling white Bianco Carrara marble countertops, intentionally designed for functionality & style.Adjacent to the kitchen and dining area is the living room, with a beautiful gas fireplace and marble mantle. Spanning 3 floors, 4 spacious bedrooms & 3 baths all fitted with marble tile & marble mosaics, the private elevator runs thru the entire building and brings you to every level of your new home. The roof has calming views of nature & foliage.The location is highly sought after, just steps to the supermarket, restaurants, cafes, T-stop, Coolidge Corner & Longwood.

$2,695,000 Active

324 Tappan Street 2 Brookline, Massachusetts

4 Beds 4 Baths 2,746 SqFt 0.16 Acres

Exceptional opportunity to own a spacious true three-bedroom, two-bath residence at the Brook House, featuring serene views of Leverett Pond from every window and a private enclosed balcony. The unit offers a desirable open floor plan, enhancing both comfort and functionality. A rare feature in a luxury building, the third bedroom adds significant value and flexibility—ideal for accommodating guests, caregivers, nanny or a home office without compromising living space. Each room has its own thermostat. The unit comes Two car tandem garage parking # 332&A. Brook House amenities include 24/7 security, heated swimming pool, fully equipped health club with steam/sauna featuring cardio workout area, weight rooms, residents lounge with WIFI, outdoor barbecue areas, basketball. Building is pet friendly. Walk/jog/bike/ paths at your door, steps to D and E “T” lines and many bus lines. Walk to Brookline Village, shopping, restaurants, Longwood medical community and many universities.

$1,120,000 Active

99 Pond Ave 417 Brookline, Massachusetts

3 Beds 2 Baths 1,590 SqFt

First time on the market since the 1900s, this grand Victorian is set in Brookline’s historical district and offers a rare opportunity for a buyer or premiere builder to restore its timeless charm. Nestled on a tree-lined street in a coveted neighborhood, this residence offers over 5,000 sq ft of versatile living space, including 8 beds and 4 full baths. Inside, period details like soaring ceilings, intricate millwork, & original hardwood floors blend with a light-filled layout. The elegant foyer flows into spacious living & dining rooms framed by oversized windows, while the kitchen & breakfast area overlook the private yard. Upstairs, a serene primary suite and additional bedrooms provide flexibility, with the top floor offering space for a studio, home office, or playroom. Set on a 0.21-acre lot, the home is surrounded by mature landscaping & offers space for outdoor entertaining or a garden. Near Coolidge Corner, schools, and MBTA, this is a rare chance to own a Brookline classic.

$2,750,000 Active

16 Kennard Rd Brookline, Massachusetts

8 Beds 6 Baths 5,076 SqFt 0.21 Acres

Welcome home to the BEST one bedroom in the building! Recently updated unit with all new finishes. One of the few high end buildings in Brookline with 24/7 concierge and security, includes a fitness room, outdoor pool, private storage, common outside deck and private balcony. Garage Parking space included. Elevator building with large laundry room. This Coolidge Corner location is just 5 minutes from the T to Fenway Park and downtown Boston. Also near Longwood Medical area hospitals, Trader Joes and Coolidge Corner theatre. A beautiful condo ready to move in and enjoy. Text for showings.

$669,900 Active

50 Longwood Ave 718 Brookline, Massachusetts

1 Beds 2 Baths 976 SqFt

Attention developers, builders, and end-users: Rare opportunity to create something truly special in one of Brookline’s most coveted Chestnut Hill neighborhoods. Sited on an expansive 18,000+ sq ft lot, this property offers exceptional potential for renovation, expansion, or new construction. The existing 3 bed, 2 bath ranch is sited on level land, with gentle slopes at the front and rear - ideal for a variety of design possibilities. Surrounded by mature oak-lined streets, 130 Fairway stands out with lush tree coverage along the side and rear, offering remarkable privacy. Located in the sought-after Heath School district, with convenient access to top public and private schools, Longwood Medical Area, Chestnut Hill shops and dining, the reservoir, parks, Green Line, and I-95 and the Mass Pike. Bring your vision and unlock the full potential of this exceptional property!

$1,750,000 Active

130 Fairway Rd Brookline, Massachusetts

3 Beds 2 Baths 1,811 SqFt 0.42 Acres

Beautifully Renovated Mid-Century Modern Gem! Nestled on a sprawling 24,459 SF landscaped lot, this home blends timeless mid-century design with modern updates. The grand living room wows with soaring beam ceilings, a wall of windows, and views of the screened porch and serene backyard. The newly renovated kitchen features sleek cabinetry, countertops, appliances, and a peninsula with easy access to the deck. The main level boasts three spacious bedrooms, two updated baths, and a cozy wood-burning fireplace. The primary suite overlooks the lush yard, offering a peaceful retreat. The finished lower level is ideal for guests or extended family, with a great room, kitchenette, patio access, a fourth bedroom, full bath, studio, bonus room, and abundant storage. New flooring, fresh paint, updated baths, and select windows/doors complete this move-in-ready home. A rare find combining architectural charm, modern comfort, and flexible spaces—this one’s a must-see!

$2,560,000 Active

367 Newton St Brookline, Massachusetts

4 Beds 3 Baths 3,243 SqFt 0.56 Acres

If you're dreaming of effortless living in a vibrant neighborhood, this Chestnut Hill condo will steal your heart. Picture mornings on your private deck overlooking lush landscaping, afternoons strolling to local favorite spots at The Street, and evenings enjoying nearby restaurants or a newly released movie. With a bright, open layout, this 2-bed, 2-bath condo features sleek wood floors, a renovated kitchen with quartz countertops and updated baths for a modern touch. The primary suite offers a tranquil retreat with its en-suite bath, while the in-unit washer/dryer and central A/C add everyday convenience. Elevator access to garage parking or minutes to the “T” make commuting or exploring Boston a breeze. Whether it’s shopping at Bloomingdale’s, grabbing coffee at Blue Bottle or hitting the gym at Equinox, everything you need is just minutes away. This beautiful condo is pet-friendly with trustee approval. Welcome to easy living!

$799,000 Active

25 Holly Ln 1D Brookline, Massachusetts

2 Beds 2 Baths 1,039 SqFt

Welcome to this top floor unit in this classic brownstone in the heart of Brookline’s highly sought-after Washington Square. This beautifully maintained three-bedroom residence seamlessly blends classic character with thoughtful modern updates. Renovated eat-in kitchen and bathrooms provide contemporary comfort, while original details such as hardwood floors, elegant wainscoting, and crown molding preserve the home’s timeless appeal. The spacious layout is filled with natural light thanks to abundant windows and skylights, creating a warm and inviting atmosphere throughout the home. The updated kitchen offers both functionality and style, making it ideal for everyday living and entertaining. Enjoy the convenience of in-unit laundry and step outside to your private deck—perfect for morning coffee or relaxing at the end of the day. A unique feature is the exclusive roof rights, offering the opportunity to build a private roof deck with sweeping city views—an exceptional outdoor retreat.

$1,499,000 Active

14 Claflin Road 3 Brookline, Massachusetts

3 Beds 2 Baths 1,520 SqFt

$775,000 Active

1731 Beacon St 512 Brookline, Massachusetts

1 Beds 1 Baths 925 SqFt 0.23 Acres

Rare, fully renovated home (2025) offering 3,250+ SF, exceptional skyline views from Cambridge to Back Bay and four private outdoor spaces. This condominium exemplifies a refined standard of living, presenting a luxurious residence distinguished by amazing design and crafted with top tier materials. Large rear addition provides over 2,175 SF on the main living level (2nd floor) with 3 bedrooms, 2.5 baths, central kitchen, formal dining room, living room, home office, laundry and two balconies. 3rd floor primary suite features a sitting room with wet bar and an expansive roof deck with gas BBQ connections. Lower level mudroom has direct entry from two attached garage parking spaces (wired for EV charging). Plus a private 470+/- SF yard. Architect plans available to add a private elevator from garage to living level.

$3,395,000 Active

197 Winchester Street 1 Brookline, Massachusetts

4 Beds 4 Baths 3,261 SqFt

Exceptional New Construction in the Heart of Washington Square. Experience sophisticated urban living in this stunning, newly constructed elevator building, complete with garage parking and premium finishes throughout. Step into a bright, open-concept floor plan featuring 9-foot ceilings, expansive floor-to-ceiling windows, and a seamless flow between the living, dining, and kitchen areas — perfect for both relaxing and entertaining. The gourmet kitchen boasts high-end appliances, modern cabinetry, and elegant finishes that elevate every detail. Enjoy the convenience of in-unit laundry, and a large private patio. Three are three spacious bedrooms with two luxurious baths designed for ultimate comfort. This pet-friendly residence offers everything a modern city dweller could desire, combining comfort, style, and functionality. A commuter’s dream, the home is ideally located just moments from two “T” lines, offering easy access to downtown and beyond.

$2,064,000 Active

45 Bartlett Crescent 201 Brookline, Massachusetts

3 Beds 2 Baths 1,595 SqFt

$1,990,000 Active

303 Russett Road Brookline, Massachusetts

5 Beds 4 Baths 3,000 SqFt 0.11 Acres

Spacious 1 BED 1.5 BATHROOM AT 50/60 LONGWOOD. Open KITCHEN w/ STAINLESS STEEL APPLIANCES, W/ BREAKFAST BAR. VIEWS OF BOSTON. LARGE WALK IN CLOSETS, HARDWOOD FLOORS THRU-OUT, CENTRAL AC. BUILDING FEATURES 24 CONCIERGE, SWIMMING POOL, CLUB ROOM, GYM, ONSITE MANAGEMENT. BUILDING IS LOCATED IN COOLIDGE CORNER, EASY WALK TO LONGWOOD MEDICAL AREA, BOTH C AND D GREENLINE, TRADER JOES, & LOTS OF PARKS. STAND ALONE PARKING SPOT.

$645,000 Active

50 Longwood Ave 712 Brookline, Massachusetts

1 Beds 2 Baths 973 SqFt

Set atop a classic brick row house in Brookline’s coveted Cottage Farm/St. Mary’s neighborhood, this bright top-floor 2BR offers approx. 1,102 sq ft of well-designed living. Features include high ceilings, hardwood floors, oversized windows, and exposed brick. The spacious south-facing eat-in kitchen provides abundant cabinetry, generous counter space, and pantry storage. Bedrooms are positioned on opposite sides of the living room for added privacy. In-unit washer/dryer and 1 exclusive outdoor parking space offer everyday convenience. Just 1 block to the Green Line and moments to Beacon St dining, 0.4 mile to BU, Kenmore Sq, Longwood, Fenway Park, and Amory Park.

$945,000 Active

8 Euston St 8 Euston St U: 5 5 Brookline, Massachusetts

2 Beds 1 Baths 1,102 SqFt

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