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401 Heath Street, Brookline
$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.
133 Wolcott Road, Brookline
$1,649,000
4 Beds ⋅ 3 Baths ⋅ 73572511 MLS
Captivating colonial tastefully designed for elegant entertaining and comfort in mind. Privacy + nature abound in this 4 bedrooms, 3 bathrooms + 2450 square feet of refined living space in a premier Chestnut Hill location. Near Baker Elementary school (grades K-8) + close proximity to Putterham Shops, tennis, golf, wildlife sanctuary, Longwood Medical Area, Arnold Arboretum + Jamaica Pond. First floor has living room with wood burning fireplace, family room, bedroom with full bath + access to expansive outdoor deck. In the heart of the residence is a beautifully renovated kitchen with custom white shaker cabinets, sleek black granite countertops, stainless steel appliances + generous center island. Upper level has a sprawling primary bedroom suite complimented by majestic sunset views + an abundance of attributes such as walk-in closet, separate sitting area + spa-like bath with dual sink vanity, glass enclosed shower + soaking tub/jacuzzi. Additional finished lower level provides versatile space for a fitness gym, home theatre or home office to meet today's evolving lifestyle needs. One car garage, one carport + plenty of additional driveway parking make this an ideal residence to call home.

133 Wolcott Road, Brookline

Listing courtesy of Listing Agent: Mary Lochner from Listing Office: Coldwell Banker Realty - Brookline.
58 Pleasant Street Unit 2, Brookline
$865,000
2 Beds ⋅ 2 Baths ⋅ 73571471 MLS
A Rare Coolidge Corner Opportunity — One Home, So Many Possibilities...Discover a truly distinctive brownstone condo in the heart of Brookline’s highly sought-after Coolidge Corner. Offering the flexibility to live as a 1-bedroom with an exceptionally large private office/flex space—or as a 2-bedroom, this spacious home adapts beautifully to your lifestyle.Set within a charming brownstone, the residence combines classic character with thoughtful updates, including soaring 9-foot ceilings, a spacious kitchen with a vented hood, and two full bathrooms.,The private primary suite is located on its own level, accessed by a distinctive spiral staircase. The open staircase creates a loft-like connection to the main living area, while offering a separate and private-feeling retreat.But the real surprise is outside. Step into your own private outdoor oasis, featuring an expansive deck and covered patio—an uncommon luxury in Coolidge Corner and the perfect setting for morning coffee, entertaining friends, gardening, or simply enjoying your own space. Whether you need a true second bedroom, a dedicated home office, creative studio, guest space, or simply room to spread out, this home gives you options that are hard to find in Brookline .Flexible. Spacious. Private. Full of possibilities. Come see why this unique Coolidge Corner residence deserves a closer look.

58 Pleasant Street Unit 2, Brookline

Listing courtesy of Listing Agent: Sandra Morgan from Listing Office: Amo Realty - Boston City Properties.
71 Sears Road, Brookline
$11,750,000
6 Beds ⋅ 6 Baths ⋅ 73570794 MLS
One of Brookline’s most exceptional offerings in over a decade, this remarkable 1929 Colonial Revival estate is set on two beautifully landscaped acres in the town’s prestigious estate area. The 14-room residence offers 7,500 square feet of living space and showcases timeless architecture and exceptional craftsmanship. Set atop a private drive marked by stately stone pillars, the home is surrounded by sweeping lawns, specimen trees, perennial gardens, and a tranquil man-made freshwater creek. An inviting in-ground pool enhances the serene outdoor setting. Inside are six spacious bedrooms, four full baths, and two half baths, including a luxurious primary suite with a spa-like bath. Elegant formal rooms flow seamlessly into comfortable living areas, ideal for both grand entertaining and everyday living.Offering rare privacy with exceptional convenience, this distinguished property is located less than five miles from Back Bay.

71 Sears Road, Brookline

Listing courtesy of Listing Agent: Chamberlain Group from Listing Office: Coldwell Banker Realty - Brookline.
21 Crowninshield Rd Unit 2-1, Brookline
$2,299,000
4 Beds ⋅ 4 Baths ⋅ 73570781 MLS
Newly staged!!!! This mint condition 3+ bedroom, 3.5 bath corner townhouse is offered for the first time since it was built in 2022. The space has been thoughtfully updated with custom built-in shelving and a striking Italian Aqua Blue matte tile surround framing the gas fireplace—complementing the sun-drenched living room's white oak floors. The chef's kitchen boasts Caesarstone counters, a 5-burner Bertazzoni range, 48" Thermador refrigerator, and Bosch dishwasher, flowing seamlessly into a dining area perfect for gatherings. The generous primary suite features abundant closet space and an en-suite bath with glass shower and premium fixtures. A well-appointed guest bedroom, third-floor bedroom with private bath, and flexible bonus room round out the living space. Step outside to your private patio retreat. Two parking spaces—one garage with storage, one deeded driveway—add everyday convenience. Constructed by a respected family-owned builder with roots dating to 1936.

21 Crowninshield Rd Unit 2-1, Brookline

Listing courtesy of Listing Agent: Bill Gehan from Listing Office: Campion & Company Fine Homes Real Estate.
185 Warren Street, Brookline
$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.
62 Cypress Unit 1, Brookline
$850,000
2 Beds ⋅ 2 Baths ⋅ 73570551 MLS
PRICED TO SELL!! PRICE BELOW TOWN ASSESSED VALUE. RARE 2-UNITS-IN-1 CONFIGURATION | PRIME BROOKLINE VILLAGE LOCATION!! INVESTOR & MULTIGENERATIONAL OPPORTUNITY!Unlock the ultimate flexibility at 62 Cypress St #1, a uniquely structured property featuring two separate apartments contained under one deed: a charming 1-bedroom unit and a self-sufficient studio. Spanning 1,135 square feet of versatile living space, this property is perfect for investors looking to maximize rental income, buyers seeking a multigenerational living setup, or owner-occupants wanting to live in one side while renting out the other to pay down the mortgage. Alternatively, the layout offers the seamless potential to combine both spaces into a 2-bedroom, 2-bathroom residence. Steeped in classic 1895 Brookline charm, the property boasts stunning period details including soaring high ceilings, elegant moldings, tall wood pocket doors, oversized windows, and original hardwood flooring throughout. The primary apartment features a sun-drenched living room with a bay window, a fully renovated eat-in kitchen with granite countertops and stainless appliances, a comfortable spacious bedroom, and a convenient in-unit washer and dryer. The adjacent studio apartment functions perfectly as an independent guest house, passive income stream, or private home office, complete with its own large bay window, full bathroom, and a functional kitchenette. Condo includes 1 parking space and a pet-friendly association. Perfectly situated in the heart of Brookline, you are just steps away from Brookline Village, the Green Line T-station, Emerson Park, and Brookline High School. Enjoy an easy commute or quick access to the world-renowned Longwood Medical Area, local shopping, dining, and major employment centers. This is an incredibly rare opportunity to secure an asset with immediate equity growth and unparalleled lifestyle options in one of Greater Boston's most desirable communities!

62 Cypress Unit 1, Brookline

Listing courtesy of Listing Agent: Luxe Home Team from Listing Office: 1st Knock Realty.
115 Freeman St Unit 1, Brookline
$699,000
1 Beds ⋅ 1 Baths ⋅ 73570524 MLS ⋅ ['Freement Park Condominuums'] BLDG.
It's a rare opportunity to buy a property condo in this beautiful corner lot with picturesque over look from living room and bed room. It is a walking distance of Green C& D line and Boston university, long wood medical center. A great investment with move in condition - and the price for a new owner to someday upgrade the bath and kitchen. Enjoy deeded garage parking. The condo has 3 guest spots for visitors. This special first floor 1-bed/1-bath unit features gleaming hard wood floors throughout, open living and dining area, with ample closet space, plus an additional storage unit in the building's lower level #"1". Laundry in the next two buildings #127 basement. . Price is just reduce significantly. Don't miss this exceptional opportunity to own a remarkable condo!!

115 Freeman St Unit 1, Brookline

Listing courtesy of Listing Agent: Jessie Chan from Listing Office: Primary Homes Realty LLC.
630 Hammond St Unit 104, Brookline
$1,099,000
2 Beds ⋅ 2 Baths ⋅ 73570258 MLS
Welcome to this exceptionally maintained 2-bedroom, 2-bath condominium in a prime Chestnut Hill location. Filled with natural light and featuring high ceilings and hardwood floors throughout, this inviting home offers an ideal combination of elegance, comfort, and convenience. The spacious living room is anchored by a cozy gas fireplace and large windows that flood the space with sunlight. An eat-in kitchen with stainless steel appliances opens seamlessly to the dining area, creating a wonderful layout for both everyday living and entertaining. The thoughtfully designed floor plan includes a generous primary bedroom suite with an en suite bath and custom fitted closets, a well-proportioned second bedroom, a second full bathroom, and the convenience of in-unit laundry. Enjoy seamless indoor-outdoor living with two private patios, perfect for morning coffee, al fresco dining, or relaxing at the end of the day. Additional highlights include two garage parking spaces and dedicated garage storage, providing exceptional convenience and value. Ideally situated near The Street at Chestnut Hill, Chestnut Hill Square, restaurants, shopping, the Green D line, and major commuter routes, this exceptional residence offers the best of one of Greater Boston's most sought-after neighborhoods.

630 Hammond St Unit 104, Brookline

Listing courtesy of Listing Agent: The Kennedy Lynch Team from Listing Office: Hammond Residential Real Estate.
19 Short St Unit 6, Brookline
$599,000
2 Beds ⋅ 1 Baths ⋅ 73566468 MLS
Set on a quiet side street just off Beacon Street, this upper-floor corner 2-bedroom, 1-bath condo offers an ideal balance of classic Brookline character and everyday convenience. High ceilings, hardwood floors, oversized windows, and multiple exposures fill the home with abundant natural light. The spacious layout includes two well-proportioned bedrooms and a comfortable living area. Ideally positioned between Coolidge Corner and Washington Square, the home is surrounded by neighborhood cafés, restaurants, shops, parks, Trader Joe’s, and Whole Foods. The Brandon Hall and Summit Avenue Green Line C stations are just moments away, offering convenient access to Longwood Medical Area, Fenway, Kenmore Square, Boston University, and downtown Boston.

19 Short St Unit 6, Brookline

Listing courtesy of Listing Agent: USLiving Team from Listing Office: Hooli Homes Boston.
12 Kilsyth Road Unit 3, Brookline
$1,440,000
3 Beds ⋅ 2 Baths ⋅ 73566068 MLS
Turnkey elegance in Washington Square! This exceptional, sun-drenched 3-bedroom, 2-full-bath residence spans 1,759 sq. ft. on the quiet 2nd floor of an intimate, professionally managed 4-unit building. Combining classic historic character with premium modern updates, the home features soaring high ceilings, meticulously restored original woodwork, oversized windows, and brand-new hardwood floors throughout. The interior has been expertly plastered and painted.Newly reimagined: We have opened the wall between the kitchen and dining room, creating a seamless, flowing open-concept space that enhances the home's grandeur and makes it ideal for entertaining. Enjoy a just-remodeled kitchen featuring modern finishes and appliances, a spacious formal dining area, a distinct living room, and a connected extra room that can serve as either a large office or a separate entertaining area. Additional highlights include two completely gut-renovated full bathrooms with contemporary finishes, a separate large laundry room, a spacious private porch, central A/C and heating, private basement storage, and the rare bonus of two dedicated parking spaces. Perfectly situated on a serene street just moments from the T, shops, and dining. Exceptional quality and craftsmanship throughout—a must-see!

12 Kilsyth Road Unit 3, Brookline

Listing courtesy of Listing Agent: Michael Lukatsky from Listing Office: Dream Home Realty.
215 Crafts Rd Unit 2, Brookline
$725,000
2 Beds ⋅ 1 Baths ⋅ 73565940 MLS ⋅ ['Lisa Condominium'] BLDG.
SELLER OFFERING UP TO $14,000 IN BUYER CLOSING COST CREDIT, INCLUDING TOWARD A 2-1 TEMPORARY MORTGAGE RATE BUYDOWN! ALL OTHER TERMS NEGOTIABLE. Financing incentive subject to lender approval and applicable loan guidelines. Welcome to 215 Crafts Road, a bright 2-bedroom condo on a tree-lined street in Brookline's Chestnut Hill neighborhood. This second-floor home offers approx. 930 sq. ft., hardwood floors, abundant natural light, and open living/dining space. The updated kitchen features stone countertops, stainless steel appliances, gas cooking, and ample cabinetry. Enjoy two private decks for dining or relaxing outdoors.Features include in-unit laundry, basement storage, one assigned off-street parking space, 2019 replacement windows, and a newer hot water tank. Set in a self-managed three-unit association with a low condo fee. Near Brookline and Chestnut Hill Reservoirs, Washington Square, Cleveland Circle, the Green Line, and Route 9 shopping and dining.

215 Crafts Rd Unit 2, Brookline

Listing courtesy of Listing Agent: Western Atlantic Group from Listing Office: Compass.
77 Pond Ave Unit 509, Brookline
$560,000
1 Beds ⋅ 1 Baths ⋅ 73565520 MLS ⋅ ['Brook House'] BLDG.
Welcome to this exceptional one-of-a-kind 1Bed/1Bath with balcony and one garage parking space at Brook House Condominium, ideally situated just steps from Brookline Village T Station, offering effortless access to the Longwood Medical Area, downtown Boston, and nearby universities. This fully renovated unit features top-of-the-line appliances, including Sub-Zero and a Wolf gas range, along with a custom cedar closet and exceptional high-end finishes throughout.The Brook House is a well-maintained, full-service building with outstanding amenities, including 24-hour security, onsite management, package service with notifications, an outdoor swimming pool, a fitness center, a clubroom, tennis, pickleball, and basketball courts, and a courtyard with grills and seating areas.

77 Pond Ave Unit 509, Brookline

Listing courtesy of Listing Agent: Miki Honda from Listing Office: Deland Real Estate, LLC.
1896 Beacon St Unit PH3, Brookline
$975,000
3 Beds ⋅ 2 Baths ⋅ 73563483 MLS ⋅ ['1896 Beacon Street Condominium'] BLDG.
New price! Offering both classic charm and detail with a modern touch, this spacious 3 bedroom 2 bathroom home has everything on your wish list. The living room features classic built-ins, bowed windows and a cozy fireplace. Directly off of the living room with french doors is a bedroom that also functions well as a office or flex space. Down the hall are 2 additional comfortable bedrooms and 2 renovated bathrooms. The kitchen features white shaker cabinets, granite countertops, an island, stainless steel appliances and a convenient pantry closet. The kitchen opens up to a comfortable dining area. A large walk-in closet with laundry completes this space. Additional features include plenty of closet space, hardwood floors throughout, deeded parking, screened-in porch, basement storage and a condo fee that includes heat and hot water. Ideal Beacon Street location close to Washington Square, Chestnut Hill, restaurants, shopping, Green line and all that Brookline has to offer.

1896 Beacon St Unit PH3, Brookline

Listing courtesy of Listing Agent: Andrew M. McKinney from Listing Office: Donnelly + Co..
1584 Beacon St Unit A, Brookline
$549,000
1 Beds ⋅ 1 Baths ⋅ 73562784 MLS
Beautifully renovated in 2010 South-facing HANDSOME BRICK BUILDING, perfectly situated between Washington Square and Coolidge Corner, high above Beacon Street. Spacious light-filled rooms, gleaming hardwood floors throughout, tall ceilings, large windows overlooking tree tops. New granite and stainless kitchen, beautiful new bathroom, in unit laundry and central AC, large closets and huge private storage room in the basement. Low condo fee, Near T and shops, easy access to Longwood Medical.

1584 Beacon St Unit A, Brookline

Listing courtesy of Listing Agent: Zhonghui Zhu from Listing Office: Keller Williams Realty.
99 Pond Ave Unit 520, Brookline
$849,000
2 Beds ⋅ 2 Baths ⋅ 73562627 MLS ⋅ ['The Brookhouse'] BLDG.
Stunning renovated 2 Bed 2 Bath for purchase at the Brook House! Clean and modern High end finishes featuring cherry hardwood floors, crown moulding through-out, recess lighting, open floor plan with a garage parking spot. Kitchen has gas oven, granite counter tops, and sleek backsplash. Both bathrooms are renovated. Off the living room is a large balcony with calm serene views of courtyard. The Brook House is an elevator full-service offering exceptional amenities, including central air conditioning, a heated outdoor swimming pool, two fitness centers, tennis courts, basketball courts, 24-hour security, and on-site professional management. Building is pet friendly. Located in an unbeatable A+ location, the building is just a short walk to the Green Line (D & E), multiple bus routes, and the Longwood Medical Area,. Easy access to restaurants, supermarkets, getting into Boston. Don't miss this opportunity to enjoy luxury amenities, scenic views, and one of Brookline's most convenient locations!

99 Pond Ave Unit 520, Brookline

Listing courtesy of Listing Agent: Sheryl Lezberg from Listing Office: Captivating Realty.
103-105 Colbourne Crescent, Brookline
$2,500,000
7 Beds ⋅ 4 Baths ⋅ 73562477 MLS
Owner is Broker.

103-105 Colbourne Crescent, Brookline

Listing courtesy of Listing Agent: Aaron Adler from Listing Office: Appraisals Unlimited, Inc.
292 Clinton Rd, Brookline
$3,700,000
6 Beds ⋅ 5 Baths ⋅ 73561991 MLS
292 Clinton Road is a timeless Victorian residence, built in 1892 and prominently situated in Brookline’s Fisher Hill neighborhood. Rich in architectural detail, this meticulous home has been thoughtfully updated while preserving elegance and craftsmanship. A welcoming front porch leads to a gracious foyer with soaring ceilings, abundant natural light and original woodwork. Designed for grand entertaining and comfortable everyday living, the first floor features a fireplaced living room, dining room, family room with a bay window, a renovated Chef’s kitchen, pantry, mudroom and half bath. A stunning staircase leads to the second level, with a charming sun-drenched landing and a wall of glass. The primary suite offers a custom walk-in closet, and renovated en-suite bath, accompanied by two additional good-sized bedrooms with en-suite baths and a second-floor laundry room. The third floor offers flexibility with three additional bedrooms, a full bath, and a spacious room ideal for a home office.

292 Clinton Rd, Brookline

Listing courtesy of Listing Agent: Luan White from Listing Office: Coldwell Banker Realty - Brookline.
37-39 Beaconsfield Road, Brookline
$2,999,000
9 Beds ⋅ 5 Baths ⋅ 73561142 MLS
RENOVATED Side-by-Side 2-FAMILY in BROOKLINE near Washington Square. Townhome Style Layouts, Each Unit has a Private Entry & Each home enjoys Private Outdoor Space, Deck + Terrace + Patio. Central A/C with separate HVAC. The Large DRIVEWAY, holds 3 Car Parking in Tandem. Strong Rental History! One Unit (#37) is 1600SF, 4BR/2BA, located on the right side and can be "Owner Occupied" while you collect rent ($7,225/month) next door at #39 w/Lease thru 8/31/27. That Penthouse Duplex is Spacious & Renovated with 5 Bedrooms/3 Bathrooms. The Living/Dining showcase a Wall of Windows, overlooking a Tree-lined Beaconsfield Road. Each room is Bright & Sundrenched across 3000 Square Feet. The finishes throughout are Condo-Quality! Beautiful Hardwood Floors, Central A/C, In-Unit Washer/Dryer. Entering the Kitchen, The Delighted Chef in YOU feels at home with a Gas Cooking & High-End Appliances like VIKING + SUB-ZERO. On the left side, #39 has generously-sized Bedrooms with a WOW Primary Suite --Walk in Closet--Primary Bathroom. Cherry Wood Cabinets surround a Double Vanity. The Cherry on Top? The Vanity has Custom Storage on ALL sides...Left | Right | Center...PRIME LOCATION with Access to Washington Square's Restaurants, Botique Shops and Star Market. Just minutes to the Beaconsfield Green Line (T) station, D Line + C Line. Only 10 min walk to Brookline High School or The Brookline Reservoir. Beaconsfield is a side street, making this an exceptional Investment Opportunity.

37-39 Beaconsfield Road, Brookline

Listing courtesy of Listing Agent: Collin Bray from Listing Office: Century 21 Cityside.
811 Heath St Unit Rear, Brookline
$2,100,000
4 Beds ⋅ 5 Baths ⋅ 73560438 MLS
TWO CAR GARAGE: This exceptional contemporary townhome offers 3,193 square feet of sophisticated living space in the heart of Chestnut Hill. Located in the highly desirable Brookline school district, this four-bedroom, four-and-a-half-bath residence combines refined contemporary design, premium finishes, and the comfort of single-family living with the convenience of condominium ownership.Bathed in natural light from oversized black-framed windows, the open-concept main level features 8-inch white oak hardwood flooring, soaring ceilings, and a beautifully appointed chef's kitchen with custom cabinetry, quartz countertops, premium stainless steel appliances, a six-burner Bosch gas range, and an oversized center island overlooking the dining and living areas. Sliding glass doors open to a private patio and fenced yard, creating seamless indoor-outdoor living, while a stylish tiled powder room completes the main level.The second level features two spacious en-suite bedrooms, including a luxurious primary suite with a custom walk-in closet and spa-inspired bath featuring elegant tilework and a frameless glass shower. The top level offers two additional en-suite bedrooms, a striking glass-enclosed office, and a dedicated laundry room.Additional highlights include designer lighting, a tiled mudroom with custom built-ins, abundant storage, and two assigned heated garage parking spaces.Moments from The Street Chestnut Hill, Chestnut Hill Square, Hammond Pond Reservation, Skyline Park, Route 9, Longwood Medical Area, and downtown Boston. Never occupied, this extraordinary residence offers a rare opportunity to own a turnkey luxury home in one of Brookline's most sought-after neighborhoods.

811 Heath St Unit Rear, Brookline

Listing courtesy of Listing Agent: Marjorie Gold from Listing Office: Hammond Residential Real Estate.
1724 Beacon St Unit 1, Brookline
$599,000
2 Beds ⋅ 1 Baths ⋅ 73559842 MLS
Beautifully updated 2 bedroom condo in the heart of Brookline's coveted Washington Square. This move in ready garden level home features soaring ceilings, hardwood floors, recessed lighting, and central air throughout. The thoughtfully designed kitchen offers oak cabinetry, granite countertops, and a movable island, while the updated bath includes a Jacuzzi tub. Both bedrooms are generously sized with custom California Closets, and the home includes a private, designated full-size laundry area plus two tandem off-street parking spaces. Professionally managed, this pet-friendly association offers low condo fees, high owner occupancy, and lead certification. Unbeatable location just steps to the Green Line C & D branches, Star Market, neighborhood cafés, restaurants, and shops, with convenient access to Longwood Medical Area, downtown Boston, Boston University, Boston College, and major highways.

1724 Beacon St Unit 1, Brookline

Listing courtesy of Listing Agent: Laura Springer from Listing Office: Coldwell Banker Realty - Milton.
86 Chestnut St, Brookline
$1,699,000
9 Beds ⋅ 4 Baths ⋅ 73559809 MLS
Investors, take note! Don't miss this exceptional opportunity to own a three-family property in one of Brookline's most sought-after locations. Situated near Brookline Village, this property is just a 12-minute walk to the Green Line, providing convenient access to Fenway, Downtown Boston, and beyond. The MBTA Route 60 bus to the Longwood Medical Area is just steps from the front door. Enjoy a highly walkable neighborhood with easy access to grocery stores, restaurants, parks, walking trails, and all the amenities that make Brookline such a desirable place to live.Add your own modern day updates, and with repairs, this classic property has the potential to truly shine! Large driveway accommodates multiple cars for easy off street parking.! Located in a community renowned for its exceptional schools, vibrant neighborhoods!

86 Chestnut St, Brookline

Listing courtesy of Listing Agent: Sarah McIntyre from Listing Office: Red Tree Real Estate.
40 Winchester St Unit 8, Brookline
$429,000
1 Beds ⋅ 1 Baths ⋅ 73559243 MLS ⋅ ['40 Winchester St Condo'] BLDG.
Charming 1 bedroom condo in Coolidge Corner -Top floor — walk to the C Line, buses & Mass Pike, plus all the shops/restaurants of Coolidge Corner & Washington Square. Low condo fee keeps carrying costs down, and owner-occupants may qualify for Brookline's residential tax exemption for added savings. Move-in ready with a freshly updated kitchen (stainless appliances, new sink, granite counters) and updated bath (new vanity, medicine cabinet, toilet, lighting). Bright living room with decorative plasterwork, molding, bow windows & recessed lighting; new ceiling fan/light. High ceilings throughout. Large front closet plus two bedroom closets for great storage. A smart, low-maintenance way to stop renting and start owning in one of Brookline's best locations.

40 Winchester St Unit 8, Brookline

Listing courtesy of Listing Agent: Jay Liu from Listing Office: Jiang Hua Liu.
1490 Beacon St Unit 3, Brookline
$639,000
1 Beds ⋅ 1 Baths ⋅ 73559050 MLS ⋅ ['Colonial Arms'] BLDG.
Sunlit and sprawling condo in the heart of Brookline right on Beacon Street between Coolidge Corner and Washington Square. This large 900+ sq ft one bedroom features: gracious foyer with beautiful arched entryways, sparkling hardwood floors, high ceilings, separate dining area and excellent closet space plus TWO additional storage spaces in basement. Tree top views make this feel like a true urban oasis, and pristinely maintained courtyard adorned with gorgeous flowers and perfectly manicured grass space. The unit is well-maintained but could use a kitchen/bath refresh to make it sparkle. Best of all, incredible location with the T right at your doorstep and directly adjacent to the steps to Corey Hill Park atop Summit Ave which has a playground and magical views of the city... and then minutes to all the conveniences of both Washington Square and Coolidge -- endless shops, restaurants, grocery stores and more. Plus convenient to Longwood Medical, Fenway, Downtown, both BC & BU and more! Wonderful opportunity for an owner-occupant or an investor. Very solid rental history and previously rented for $2750/month. Must see!

1490 Beacon St Unit 3, Brookline

Listing courtesy of Listing Agent: Fleet Homes Group from Listing Office: Keller Williams Realty.
65 Francis Unit A, Brookline
$2,695,000
5 Beds ⋅ 5 Baths ⋅ 73558493 MLS ⋅ ['65-67 Francis St'] BLDG.
Last Unit Available! Thoughtfully renovated, this 2025 Coolidge Corner condominium blends classic charm with modern comfort. A welcoming mudroom opens to a sunlit kitchen with generous counter space, perfect for cooking or hosting. The main level features a cozy family room with fireplace, cheerful breakfast nook, and powder room. Upstairs, a curved staircase leads to a reading nook, laundry, and serene primary suite with walk-in closet and double-vanity ensuite. A second ensuite bedroom completes the floor. The finished lower level offers a spacious rec room, wet bar, two additional bedrooms (one ensuite), and another full bath, with direct walk-out to the backyard and parking. Filled with natural light and designed for everyday living and entertaining, this move-in ready home is located near Brookline’s shops, cafés, schools, parks, and medical centers.

65 Francis Unit A, Brookline

Listing courtesy of Listing Agent: Rozita Tabatabaei from Listing Office: William Raveis R.E. & Home Services.
16 Garrison Road Unit 7A, Brookline
$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.
1600 Beacon St Unit 904, Brookline
$521,000
1 Baths ⋅ 73557405 MLS ⋅ ['Washington Square Condominium'] BLDG.
Prime Washington Square location. This bright and sunny, modern, extra large studio offers 557 square feet of living space, plus a separate room ideal for a home office. This 9th floor freshly painted unit with new floors features southern exposure, a maple kitchen with granite countertops and stainless steel appliances, two large closets, and pleasant treetop views. The professionally managed building offers a concierge, two elevators, fitness center, common laundry room, bicycle storage, and a shared rear patio. Rooms are virtually staged.

1600 Beacon St Unit 904, Brookline

Listing courtesy of Listing Agent: Olga Perelman from Listing Office: Olga Perelman.
1600 Beacon St Unit 902, Brookline
$875,000
2 Beds ⋅ 2 Baths ⋅ 73556341 MLS ⋅ ['Washington On The Square'] BLDG.
Discover sophisticated urban living at 1600 Beacon Street, unit #902 in the heart of Washington Square! This amazing southern exposure 9th floor, 2-bedroom, 2 bath corner unit comes with garage parking. The unit is on the 9th floor in an elevator building and offers an open floor plan with a beautiful kitchen, stainless steel appliances, cherry cabinets, stone counters and backsplash. The unit has been freshly painted, with new maple wood floors in the master bedroom. The living area has wood flooring as well and beautiful city panoramic views throughout. There is central air, gas heat and extra deeded storage. The association is professionally managed, has a concierge, full-time cleaning man and on-site maintenance person several days a week. There is an exercise room, bike storage, outside common sitting area and on-site laundry. Pets are allowed for owner occupants. This premier location is near the Green line C & D train, bus line, restaurants, coffee shops, Star market, Whole foods , Trader Joe’s, Longwood medical area, Boston College, Newton, Boston, Cambridge and major commuting routes. Come see what easy living looks like!

1600 Beacon St Unit 902, Brookline

Listing courtesy of Listing Agent: Luan White from Listing Office: Coldwell Banker Realty - Brookline.
5 Kendall, Brookline
$140,000
73556302 MLS

5 Kendall, Brookline

Listing courtesy of Listing Agent: Aziz Turkan from Listing Office: NextGen Realty, Inc..
3 Kendall, Brookline
$95,000
73556286 MLS
Turnkey café/restaurant opportunity in a highly visible location with a bright, inviting interior and modern finishes. This well-maintained space features an open dining area, stylish décor, updated flooring, a professional coffee bar, commercial kitchen equipment, refrigerated display cases, prep area, storage, and a clean customer restroom. Large front windows provide abundant natural light and excellent street presence, while the efficient layout allows for smooth daily operations. Ideal for a café, bakery, dessert shop, sandwich shop, breakfast spot, or other food service concept. A rare opportunity to own a beautifully built-out business with a welcoming atmosphere and excellent potential for an owner-operator or investor.

3 Kendall, Brookline

Listing courtesy of Listing Agent: Aziz Turkan from Listing Office: NextGen Realty, Inc..

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