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

Discover this charming home tucked behind a private gate in one of the area’s most sought-after estate locations. The home has been lovingly maintained and thoughtfully updated with finishes that elevate both style and functionality. A two-story foyer with a sweeping curved staircase sets an elegant tone upon entry. At the heart of the home, a new modern gourmet kitchen offers a large center island and sunlit breakfast area that flows seamlessly to the family room, and opens to an expansive patio and lush yard. A bedroom, den and office complete the first floor. Upstairs, the primary suite is complemented by four additional bedrooms, each with its own en-suite bathroom for exceptional privacy and comfort. A second staircase enhances both convenience and architectural appeal. With its pool and hot tub, the private backyard provides the perfect retreat for gatherings or quiet relaxation. Convenient to top schools, shopping, and commuter routes.

$6,649,000 Active

88 Cutler Ln Brookline, Massachusetts

6 Beds 7 Baths 7,450 SqFt 0.78 Acres

335 Heath Street, combines the charm and architectural integrity of an established Brookline estate with the comfort and craftsmanship suited for modern living. Set on a flat, private lot just under an acre, this exceptional property includes a main house with 4+ bedrooms and an attached 3-bedroom carriage house. Thoughtful amenities enhance everyday life: 2 home offices, a dedicated gym with sauna, a dog-washing station, smart home features w/ camera system, a temperature controlled wine room, and more. Outdoors, a fully fenced, backyard and expansive bluestone patio create the perfect setting for gatherings and play, framed by mature landscaping that ensures both beauty and privacy. A two-car garage and meticulous attention to detail inside and out complete this rare, move-in-ready offering in one of Brooklines most sought-after neighborhoods.

$7,995,000 Active

335 Heath St Brookline, Massachusetts

7 Beds 10 Baths 12,814 SqFt 0.93 Acres

Step into this sun-drenched and expansive 2 bedroom, 2 bath that lives large thanks to an open-concept design and generous windows allowing light to pour in throughout the day. The living and dining areas flow seamlessly to a balcony offering serene park views, creating the perfect setting for entertaining or relaxed everyday living. Key features include a modern, well-proportioned kitchen visible from the main living area, a primary suite with a private bath and ample walk-in closet space, a second bedroom or office, and hardwood floors throughout, with a neutral palette ready for any decor. The private balcony offers outdoor seating and greenery-filled views, overlooking the magically peaceful Griggs Park. Conveniently located near Coolidge Corner, Washington Sq & Brookline Village, this home puts shops, dining, parks, public transit and the LMA all within minutes walk, drive or T ride. One assigned garage parking space and additional storage are included in the sale.

$999,999 Active

80 Park St 23 Brookline, Massachusetts

2 Beds 2 Baths 1,598 SqFt

Welcome to 80onVernon, a boutique collection of 8 new luxury condominiums in Brookline’s Coolidge Corner. Each home offers 3 bedrooms, modern finishes, garage parking, and private outdoor spaces. This unit features two garage parking spaces, two balconies, a den, and a direct access elevator. The building’s sleek exterior, oversized windows, and glass balconies maximize light and park views. Residents enjoy a stylish lobby with secure mail and package areas. Interiors feature 9-foot ceilings, floor-to-ceiling Drutex windows, open living spaces with fireplaces, and kitchens with waterfall-edge stone countertops, Dell Anno cabinetry, and Thermador appliances. Wood accents and designer lighting add warmth and sophistication. Located steps from Saint Mark’s Park, the Coolidge Corner Theatre, Trader Joe’s, and acclaimed restaurants, plus the MBTA Green Line for direct Boston access, 80onVernon blends modern design, everyday convenience, and community charm. Expected Delivery summer 2026.

$3,695,000 Active

80 Vernon 2B Brookline, Massachusetts

3 Beds 3 Baths 2,125 SqFt

This stunning ten-room residence offers 3,838 square feet of elegant living space in the heart of Washington Square. Gut renovated down to the studs by Rincon Development, the home seamlessly blends modern amenities with exquisite period details. The open floor plan is enhanced by soaring ten-foot ceilings and top-of-the-line finishes throughout. Featuring five bedrooms and four bathrooms, the property includes a luxurious primary bedroom suite with a vaulted ceiling, multiple closets, and a spa-inspired bathroom. Within the primary suite is a lofted room that can be an office, gym, private den area. Additional highlights include beautiful outdoor space, three-car parking and radiant heat on the floor of all full bathrooms. Ideally located near shops, restaurants, schools, and the Longwood Medical Area, this home combines sophistication with exceptional convenience.

$3,150,000 Active

757 Washington Street Unit 2 – PH Brookline, Massachusetts

5 Beds 5 Baths 3,838 SqFt

Sun-splashed and inviting, this fabulous Brookline condo is just two blocks from Coolidge Corner on a quiet, tree-lined street. Formerly a 3-bedroom, this top-floor 2-bedroom home offers lovely treetop views, an open living/dining area, and a fully renovated kitchen with custom cabinetry. The unit features an in-unit laundry, newer windows, custom closets, 2 dedicated storage units, and tandem, off-street parking for 2 cars. A private covered porch is ideal for al fresco dining and warm-weather entertaining. The well-maintained, professionally managed building boasts a 2025 furnace. All of this, plus access to top-rated Brookline schools and the vibrant amenities of Coolidge Corner.

$855,000 Active

58 Dwight St 6 Brookline, Massachusetts

2 Beds 1 Baths 1,045 SqFt

REGENCY PARK! Watch the sunset from this stunning 2 bed penthouse condominium in the highly sought-after modern, hi-rise luxury elevator building, Regency Park! This building is freshly renovated, and you can enjoy sunny, south-west sparkling Reservoir water views from the 15th floor! Optimally located at the foot of Fisher Hill, between Washington Sq and Dean Park, this condominium offers a wonderful opportunity to experience elevated living in a desirable location. Ascending to the fifteenth floor, there is a sense of privacy and tranquility high above the bustle of the city. The sumptuous living area provides a comfortable environment, with natural light enhancing the ambiance, which offer calm retreats for rest and rejuvenation. Residents enjoy 24 hour concierge, indoor pool, fitness center, ping-pong, roof deck and garage parking. Steps away from Green line "T", restaurants, coffee shops, banks, tennis/pickleball. Easy access to all major routes.

$1,150,000 Active

1731 Beacon St 1502 Brookline, Massachusetts

2 Beds 2 Baths 1,263 SqFt

Located on Aspinwall Hill just across from Schick park is this total gut renovated 5 bed, 4 full bath 3,450 sq. ft. duplex that artfully blends luxury with comfort. The expansive foyer leads you to a state-of-the-art chef's kitchen, complete with stone countertops, high-end Thermador appliances & island leading to a breakfast area. There is a generous deck great for entertaining as well as a formal dining area & spacious living room. This level boasts a primary suite with a walk in closet & stunning bath, plus an add'l bedroom & full bath. High ceilings accentuate this level. The lower level has 3 spacious sized bedrooms, 2 full baths along with an office space and laundry room. There is door that leads to a beautiful patio and yard. Beautiful white oak flooring flows throughout. Air conditioning and 2 parking spaces round out this stunning offering. Minutes to shops, transportation and restaurants!

$2,995,000 Active

90 Addington 1 Brookline, Massachusetts

5 Beds 4 Baths 3,450 SqFt

Experience exceptional value in this beautifully refreshed top-floor penthouse in Brookline, where contemporary style blends seamlessly with comfort. This renovated 3-bedroom, 3-bath home offers an impressive layout enhanced by warm, natural light from its desirable south-facing exposure. The open living area welcomes you with a bright, airy feel perfect for relaxing or hosting. A standout chef’s kitchen features refined quartz counters, a generous island, and premium GE Café appliances, including a double oven ideal for everyday meals or entertaining. Each bathroom is thoughtfully designed with spa-like elements, heated smart mirrors, and elegant tile detailing. Modern touches continue throughout, from the spacious bedrooms to the inviting common spaces. This penthouse delivers an ideal mix of luxury and practicality in a prime Brookline setting. Don’t miss this remarkable opportunity!

$1,275,000 Active

37 Englewood Ave 3 Brookline, Massachusetts

3 Beds 3 Baths 1,814 SqFt

A one of one in Brookline – immerse yourself in this sun-filled penthouse that seamlessly blends timeless character with modern luxury. Upon entering, one is instantly impressed by the ultra-high ceilings, grand staircase, exposed brick wall, and modern lighting fixture. The open-concept layout provides a spacious living, dining, and kitchen area. The fully renovated kitchen features an oversized island, stainless steel appliances, quartz countertops, and a wine fridge. The recently renovated bathroom features an oversized steam shower, timeless vanity, and in-unit laundry. The two bedrooms offer custom closets, high ceilings, and storage space. A private roof deck—complete with water, electricity, and built-in furniture—provides an exceptional outdoor retreat with panoramic views of the city. Additional highlights include one direct off-street parking space and hardwood floors throughout. This pet-friendly, professionally managed building will appeal to the most discern.

$1,157,000 Active

1778 Beacon St 302 Brookline, Massachusetts

2 Beds 1 Baths 1,157 SqFt

Beautifully renovated 1 bedroom in Brownstone. Fantastic Brookline location! Great layout with no wasted space! This condo has many nice features including a Stylish kitchen with quartz countertops and stainless steel appliances. The bathroom has lovely tile and a custom glass shower as well as a heated floor. Additional amenities include great closet space, a fireplace, and air conditioning. There are high ceilings, large windows, & hardwood floors throughout. Convenient location! Easy access to the 3 trainlines on the Greenline T and the MBTA buses. Neighborhood has lots of lively perks including restaurants, supermarkets, shops and the Cleveland Circle reservoir. Close proximity to B.C. and Longwood Medical area.

$489,000 Active

1880 Beacon St 6 Brookline, Massachusetts

1 Beds 1 Baths 474 SqFt

Available for the first time in 72 years, 255 Tappan Street is a beautifully maintained brick two-family home with additional living space. Perfectly positioned near Washington Square and Brookline’s top restaurants and bars, the home sits just off Beacon Street near Brookline High School and the Green Line, offering unbeatable convenience. Star Market is located right at the end of the street. Each unit is turnkey—ready for immediate move-in or rental—making this an exceptional opportunity for both homeowners and investors. Set on nearly 10,000 sq. ft. with a spacious backyard, the property features two 3-bedroom, 2-bath units with generous living and dining areas and well-equipped kitchens. The second-floor unit includes a private deck, while the additional space includes a full kitchen, 1 bedroom, 1 bath, and in-unit laundry. Added highlights include a 2-car garage, extra driveway parking, basement access from all units, and ample storage.

$2,999,999 Active

255 Tappan Street Brookline, Massachusetts

7 Beds 5 Baths 4,171 SqFt 0.23 Acres

Chestnut Hill, Brookline. Designed in 1905 by Chapman & Frazer, this Spanish Colonial estate unites house and garden across approx 1.3 acres. About 9,400 sq ft on four finished levels with 8 beds and 6.5 baths. Chef’s kitchen with oversized island, walk-in pantry, and pro appliances opens to dining and a stone terrace. Formal living and dining pair with a quiet library and a large family room. The serene primary suite offers a spa bath and custom dressing closets. Upper levels add flexible rooms for guests, work, and play. The finished lower level provides media, fitness, recreation, and storage. Courtyards, terraces, and defined garden rooms create a private setting. Historic 1906 Chapman & Frazer auto house. Within the Chestnut Hill North Local Historic District and contributing to the Chestnut Hill National Register District. Near Boston College, The Street, Chestnut Hill Mall, Wegmans, the Green Line, and Longwood Medical. First time available in more than 30 years.

$8,750,000 Active

142 Crafts Road Brookline, Massachusetts

8 Beds 7 Baths 9,400 SqFt 1.33 Acres

Welcome to this inviting 1-bedroom, 1-bathroom home in between Washington Square & Cleveland Circle! Spanning approx. 585 square feet, this urban gem offers a cozy living experience that checks off all the boxes, featuring a private entrance right next to the common outdoor space, perfect for entertaining guests! The kitchen features granite countertops, electric range, microwave and dishwasher. The bedroom includes a walk-in closet, and the bathroom boasts stylish tiled floors, adding a touch of elegance to the home. Several convenient perks including in-unit laundry, split system AC, and 1 off street parking space. Conveniently located near green line public transit, Star Market, with local restaurants and shops just moments away.

$499,900 Active

1763 Beacon Street A Brookline, Massachusetts

1 Beds 1 Baths 585 SqFt

$559,000 Active

3 Englewood Ave 9 Brookline, Massachusetts

1 Beds 1 Baths 680 SqFt

Open house Sunday, noon-130PM... A stone's throw from the restaurants and cafes of Washington Square and C line trolley is this spacious, beautifully renovated one bedroom condo with updated kitchen and bathroom. Kitchen offers extensive cabinetry, stainless appliances (incl Bosch dishwasher), granite counters, deep sink, microwave. Pet-friendly HOA. Freshly painted throughout with Benjamin Moore neutral colors. Full-sized washer-dryer in unit. Huge storage closet off living room. High ceilings. Ample windows. Positioned at the quiet rear of the building. Extremely low real estate taxes (reflect residential exemption). Very close to Whole Foods and Star Market.

$489,000 Active

19 Westbourne 2 Brookline, Massachusetts

1 Beds 1 Baths 670 SqFt

Rare new to market listing in the highly desired Amory House Condominiums with a roof top pool deck with amazing views of Boston skyline make this a can't miss. Completely updated kitchen a focal point of this home, features shaker cabinets complemented by quartz countertops and a backsplash, and new stainless steel appliances creating a stylish and functional space for culinary adventures. Updated bath and hardwood flooring throughout create a truly move in scenario. Large spacious bedroom and living room with a private patio overlooking the well manicured property add additional space and value. Parking is a front door space just steps to the entrance adds convenience not found in other units. Meticulously maintained property with a meeting or function room, laundry on your floor , exercise room with sauna and shower add all the amenities you need. Short walk to Boston University, Trader Joes, Coolidge Corner shops, and restaurants adjacent dog park and playground for you and yours

$715,000 Active

125 Pleasant St 201 Brookline, Massachusetts

1 Beds 1 Baths 798 SqFt

New to Market! Don’t miss this rare opportunity to own a beautifully maintained, sun-filled 3BR, 1.5BA condo in one of Brookline’s most sought-after locations. This inviting home features an open and airy floor plan with high ceilings, oversized windows, and abundant natural light throughout. Well-appointed kitchen boasts maple cabinetry, granite countertops, stainless steel appliances, gas cooking, and a spacious island with bar seating—perfect for both everyday living and entertaining. Additional highlights include two deeded side-by-side parking spaces (a true rarity in Brookline), low condo fees, new siding, roof, and gutters, fully deleaded. Enjoy an unbeatable location across from Heath School, just moments from public transportation, Brookline Reservoir, local shops, cafés, and restaurants, plus a free shuttle to Medical Area and Green Line stops. Move-in ready, this home offers the ideal combination of location, value, and style—a must-see!

$799,000 Active

55 Reservoir Rd 2 Brookline, Massachusetts

3 Beds 2 Baths 1,087 SqFt

Welcome to 799 Heath Street, Unit 2 - an inviting and elegant 4-bedroom, 2.5-bathroom townhouse nestled in the prestigious Chestnut Hill neighborhood of Brookline. This exquisite residence offers 2,366 square feet of modern luxury and comfort, designed with discerning tastes in mind. Step into the main level, where a gourmet kitchen and dining area set the stage for culinary delights and entertaining. The spacious living room, featuring custom woodwork and newly installed blinds, provides a perfect setting for relaxation and gatherings. Upstairs, a serene master suite awaits, alongside two additional bedrooms that offer ample space and privacy. The first level showcases a versatile bonus room, ideal for a home office or personal gym, with direct access to the attached two-car garage. Take advantage of the private outdoor space, perfect for enjoying tranquil moments or hosting intimate gatherings. Perfectly located for quick trips to neighborhood shops and markets!

$1,599,000 Active

799 Heath Street 2 Brookline, Massachusetts

4 Beds 3 Baths 2,366 SqFt

Explore this sophisticated and elegant vintage one-bedroom brownstone condo available for sale. Located in the vibrant heart of Coolidge Corner. It's conveniently close to an array of shops, restaurants, and public transportation options, including bus and train services to downtown Boston and the Longwood Hospital/Medical area. The condo fee covers heat & hot water and offers a generous storage unit in the basement. The condo is bathed in natural light, showcasing classic features like gleaming hardwood floors, high ceilings, a stunning decorative fireplace, a bow front with oversized windows & elegant crown moldings. These traditional elements are seamlessly integrated with modern conveniences such as an open layout, a beautifully updated eat-in kitchen boasting granite countertops, stainless steel appliances, and cherry cabinets. The spacious corner bedroom is adorned with a wall of windows and a large California closet. The building provides laundry facilities and bicycle storage.

$699,000 Active

119 Park Street 7 Brookline, Massachusetts

1 Beds 1 Baths 751 SqFt

Spacious and renovated 1 bed/1.5 baths at 50/60 LONGWOOD AVE. The building features 24 hour concierge, elevators, onsite management, pool and patio space, fitness center, and community room. . Fantastic layout with extremely large and open living room, separate designated dining area off the kitchen, and private balcony. Abundant walk in closet. Garage parking. Location is the phenomenal as easy walk to Longwood Medical Area, Lots of parks, restaurants, C AND D GREENLINE, TRADER JOES. Heart of Coolidge Corner.

$675,000 Active

60 Longwood Ave 307 Brookline, Massachusetts

1 Beds 2 Baths 955 SqFt

Ideally located, this lovely Victorian style condo offers the perfect combination first floor -one level living in a charming 4-unit building. Nothing better than 10-foot ceilings and oversized windows to make your space luxurious and bright. With recent upgrades over the years, this condo offers an updated & well-designed bathroom with both a tub and separate shower; double sinks & towel warmer. The kitchen offers quality-built cabinets, gas cooking, exhaust vent, and plenty of space to enjoy your coffee overlooking the garden. Plant your herbs and enjoy the lush landscape. With direct access to the common yard from the kitchen, easy access for pets & cookouts. Fabulous proximity to the new Cypress St. playground, Brookline HS, MBTA Green Line, Longwood medical, Coolidge Corner & Brookline Village. This move-in ready condo offers one parking space, to the right of the unit and 2 guest spaces in the general lot. Well managed complex with basement storage.

$998,000 Active

72 Cypress St 1 Brookline, Massachusetts

2 Beds 1 Baths 1,115 SqFt

Welcome to this exceptional 2+bedroom, 3.5-bathroom townhome in the heart of Brookline’s coveted Chestnut Hill neighborhood. Spanning three floors of thoughtfully designed living space, this home features a private elevator, central air, and in-unit laundry for ultimate comfort and convenience. Enjoy seamless entry with direct access from the garage for 2 parkings spaces, and relax outdoors on multiple balconies offering natural light and a connection to the serene surroundings. Each bedroom is generously sized, including a spacious primary suite with a spa-like bath. Located moments from scenic nature trails and just steps to the upscale shops, dining, and amenities at The Street, The Square, and the Chestnut Hill Mall—this is urban-suburban living at its finest. Don’t miss this rare opportunity to own a turnkey home in one of Brookline’s most desirable location. Welcome Home!

$1,750,000 Active

771 Heath St 771 Brookline, Massachusetts

2 Beds 4 Baths 3,070 SqFt

New Construction by a highly respected local developer. Welcome to modern luxury living in a historic neighborhood of Brookline. The Bartlett features 24 two- and three-bedroom residences that are the ultimate synergy of clean design, location, and amenities. This two-bedroom unit is appointed with Bosch appliances, 9-foot high ceilings and garage parking with EV charger available. This unit has a bright, open floor plan with easy access to a balcony with lovely views. Unit 305 has two bedrooms and two full baths, with in unit laundry. Located in the heart of Washington Square and approximately 1.1 miles to Coolidge Corner, The Bartlett is close to many restaurants, shopping options, multiple “T” locations, and other public transportation. Truly a unique offering in a sought-after location.

$1,233,850 Active

45 Bartlett Crescent 305 Brookline, Massachusetts

2 Beds 2 Baths 946 SqFt

$3,649,000 Active

80 Vernon 3B Brookline, Massachusetts

3 Beds 3 Baths 2,125 SqFt

2025 NEW CONSTRUCTION in Coolidge Corner. PH-1, 3 Beds, 3.5 Baths, 2056 SF, Single Level Living. Elevator + 2 Covered Garage Parking. Experienced Architect, Designer & Build Team. 4 PRIVATE Outdoor Areas! EXCLUSIVE ROOF DECK, "600SF" has Gas, Water, Electric. VIEWS to Back Bay are SERENE&PEACEFUL. Your Own Concierge "24/7" "Simplified Concierge" named BEST of BOSTON, Handling ALL Services. 10 Ft Ceilings, Floor to Ceiling “Statement" Windows, Sundrenched Corner Home facing EAST/WEST. Bird’s Eye Sunsets alongside Views of Iconic Coolidge Corner Movie Theatre. Finishes are Sophisticated. Opulence is Necessary. Appliances are Sub-Zero/Wolf, Quartz Stone Waterfalls down a 10ft Island. Spa Quality Baths, Double Vanity, Oversized Showers & Soaking Tub. Pet Friendly, Professionally Managed & Deeded Private Storage Included. CENTER of it ALL Means Dining, Shopping, Hospitals & Schools. Featured in “AD” Architectural Digest: Alaïa [ah-LAY-ah]. Newest Premier Boutique Luxury Condo Building.

$3,325,000 Active

14 Green Street PH1 Brookline, Massachusetts

3 Beds 4 Baths 2,056 SqFt

This spectacular new-construction floor-through is flooded with light from all sides, and offers the perfect blend of luxury, modern elegance, and functional space! It features high ceilings, beautiful white oak floors, a fireplace, heated bathroom floors, two balconies, and a gorgeous chef’s kitchen with Thermador appliances, ample counter space, and a walk-in pantry. It also boasts direct private elevator access, two-car EV-ready garage parking, and extra storage in the basement. The primary suite has two walk-in closets, corner windows, and a spa-like bath. And the fourth bedroom is adjacent to a full bathroom in a separate space behind a pocket door, so it can also function flexibly as an office, den, or private guest suite. With a state-of-the-art access system that grants entry via code, phone, fob, or facial recognition, and set on a lovely quiet street steps from everything Coolidge Corner & Brookline Village have to offer, this is premier living at its finest!

$2,550,000 Active

24 Auburn U2 Brookline, Massachusetts

4 Beds 3 Baths 1,855 SqFt

Sundrenched Penthouse! Exceptional residence with south-facing panoramic views and nearly 1,300SF of well designed living space. 2 Bedrooms, 2 Bathrooms, and 2 deeded garage parking spaces. Open-concept living and dining area is highlighted by floor-to-ceiling windows, wood floors, and crown moldings. Updated kitchen features off-white cabinetry, granite counters & stainless steel appliances. Primary suite has double closets plus an additional walk-in closet with custom built-ins and leads to an en-suite bathroom. 2nd bedroom has double closets and two floor-to-ceiling south-facing windows that fill the space with natural light. Residents enjoy a wealth of amenities including a 24-hour concierge, security cameras, a health club with steam and sauna, a heated outdoor pool, tennis and basketball courts, BBQ areas, a WiFi lounge, and an on-site management office. Across from the MBTA Green Line and just moments from the shops & restaurants of Brookline Village & The Longwood Medical Area.

$869,000 Active

77 Pond Ave 1506 Brookline, Massachusetts

2 Beds 2 Baths 1,260 SqFt

Elegant “Manhattan-style” floor-through Penthouse condominium offering 4 bedrooms, 2 full baths, and 2,276 sq ft of sun-filled living space. A gracious foyer with decorative fireplace opens to a bright living room with built-in seating and flows into a spacious family room featuring a fireplace and custom bookcases. The banquet-sized dining room showcases wainscoting and a built-in china cabinet, perfect for entertaining. A large eat-in kitchen with decorative fireplace provides wonderful everyday living space, The hallway leading to the bedrooms is graced by classic archways that enhance the home’s sense of character and flow. Enjoy the year-round sunroom and common rook deck with views of downtown Boston! Defining features of this home include refined millwork, crown moldings, high ceilings, and hardwood floors exemplifying timeless architectural detail. Additional highlights include in-unit laundry, storage, and parking for 1 car. Close to T, Reservoir, Longwood Med. and Boston..

$1,440,000 Active

487 Boylston St. 3 Brookline, Massachusetts

4 Beds 2 Baths 2,276 SqFt

A once-in-a-lifetime opportunity to own a revived Tudor masterpiece, where historic grandeur meets modern sanctuary. Nestled gracefully on a hill amongst trees & over looking the Robert T. Lynch Golf Course, this residence exudes light, warmth, and timeless sophistication. The heart of the home is a sun-filled kitchen with dual marble islands, Sub-Zero and Thermador appliances, and a dining area that opens seamlessly to the two-story deck, backyard, and heated pool—perfect for both comfortable living and extraordinary entertaining. The grand living room showcases a hand-carved and restored fireplace, oversized windows, and French doors, blending classic craftsmanship with refined modernity. Upstairs, a full-floor primary suite offers a spa bath, sitting area, fireplace and three generous closets . With dual street access, 8+ car parking, and proximity to The Street Chestnut Hill, top schools, world-class hospitals, and Harvard’s Arboretum, this home defines coveted Chestnut Hill living

$2,799,000 Active

1125 W Roxbury Pkwy Brookline, Massachusetts

4 Beds 4 Baths 3,859 SqFt 0.56 Acres

Beautifully designed two-level condo at 1856 Beacon Street, Brookline, offering approximately 913 sq. ft. of thoughtfully planned living space and available with or without furniture. This home features two bedrooms and one and a half baths, both recently gut renovated with stylish tile and modern fixtures. The main level offers a bright, open living area, a dining space that opens to a small private balcony, and an efficiently designed kitchen with light wood cabinetry, granite countertops, and stainless steel appliances including a gas range and over-the-range microwave. Hardwood floors throughout add warmth and charm, while a new water boiler ensures year-round comfort. The property also includes one parking spot for added convenience. Ideally located on the MBTA Green Line C Branch, just moments from Washington Square and Cleveland Circle, with cafés, restaurants, shops, and the scenic Chestnut Hill Reservoir nearby.

$725,000 Active

1856 Beacon St. 2C Brookline, Massachusetts

2 Beds 2 Baths 913 SqFt

Experience unexpected luxury in this unique corner townhouse-single family, offering four bedrooms across four sun-filled levels. Wall-to-wall sliders open to composite decks, filling the home with natural light and showcasing panoramic treetop and sky views. Behind its classic brick exterior, discover a spacious interior with a true wow factor. The kitchen features stainless steel appliances, an induction range, French door refrigerator, and granite countertops. Custom built-ins and generous closets provide huge amount of storage, while Mitsubishi mini-split heat pumps in every room ensure year-round comfort. Lower-level bedrooms offer private walk-out access—ideal for guests or flexible living. Nestled on a picturesque, tree-lined street that blends historic charm with modern design, this home is steps away from the C & D Lines T, grocery stores and restaurants. Enjoy tranquility, style, and urban convenience in one of the area’s most sought-after neighborhoods.

$2,000,000 Active

184 Rawson Rd Brookline, Massachusetts

5 Beds 4 Baths 2,460 SqFt 0.09 Acres

Introducing Paine Estate, a grand Georgian Revival architectural treasure located in the highly coveted Chestnut Hill neighborhood of Brookline. This outstanding property has been extensively renovated, now combining traditional style and modern amenities with a thoughtful floor plan ideal for comfortable family living and grand entertaining. Exceptional features include a grand entry hall, elegant formal sunken living room overlooking the picturesque gardens, fireplaced dining room, gourmet chef's kitchen, family room, handsome wood paneled library and an expansive great room. 6 bedrooms include the luxurious primary suite complete with separate bathrooms and dressing rooms and balcony. Additional features include a mudroom, exercise/club room, au-pair suite and wine cellar. This majestic home is surrounded by over 2 acres of beautifully landscaped grounds featuring an outside kitchen and dining area, a formal parterre garden and plunge pool. Magnificent opportunity not to be missed!

$19,000,000 Active

1014 Boylston Street Brookline, Massachusetts

7 Beds 11 Baths 13,343 SqFt 2.11 Acres

Welcome to this beautifully renovated 2025 Coolidge Corner unit, where timeless charm meets modern comfort. A welcoming mudroom opens to a sunlit kitchen with generous counter space, perfect for cooking together or hosting friends. The cozy family room with fireplace and a cheerful breakfast nook make the main level inviting, while a powder room adds convenience. A graceful curved staircase leads to a reading nook, laundry closet, and a serene primary suite with walk-in closet and ensuite bath featuring a double vanity. A second bedroom with its own ensuite completes this floor. The finished lower level offers flexible space for relaxation and fun with a rec room, wet bar, two bedrooms (one ensuite), and another full bath. Direct walk-out access leads to the patio, backyard and parking area. Move-in ready and filled with natural light, this home is designed for everyday living and entertaining, all just steps from Brookline’s cafés, shops, schools, medical facilities and parks.

$2,845,000 Active

65 Francis Brookline, Massachusetts

4 Beds 5 Baths 2,900 SqFt 0.14 Acres

Substantial price improvement. Single-family alternative. Private entrance. Lives like a single. Rarely available. Two-level townhouse on a tree-lined one-way street with a 2-car side-by-side garage parking included. A gracious and spacious home that has soaring high ceilings, with an abundance of large, insulated windows. This sun-filled home has light streaming in throughout. There is a large open living dining with tree-top views. The sunny, large eat-in kitchen has lots of additional wall cabinets for great storage, granite counters, and stainless steel appliances. The 2nd level has a large primary suite with an ensuite bath, 2 additional bedrooms, and a large main bath. Great closet space throughout. Minutes to T, school, park, public library, shopping, restaurants, and Longwood Medical. Easy access to downtown Boston.

$1,995,000 Active

125 Crowninshield Road 125 Brookline, Massachusetts

3 Beds 3 Baths 2,163 SqFt

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

$5,000,000 Active

540 Chestnut Hill Ave Brookline, Massachusetts

5 Beds 5 Baths 6,419 SqFt 1.03 Acres

This stunning new construction condo has it all - 3 beds, 3.5 baths, elevator, 2-car garage, private fenced yard w/deck and patio! Inspired design and exceptional attention to detail combine to create a sophisticated, comfortable and versatile living environment. Elegant living room features gas fireplace, built-ins, and French doors that open to deck/yard, allowing for easy indoor-outdoor lifestyle. Well-appointed kitchen offers Thermador appliances, custom cabinetry, large island w/breakfast bar, dining area, wet bar, pantry. Family room offers flexible use as media room, playroom, home office. First-floor bedroom suite features spa-like bathroom. Upstairs primary bedroom suite is a sanctuary, complete w/luxurious bathroom, walk-in closet, balcony. Second floor has add’l bedroom with en suite bath, plus laundry area. Private elevator access from garage to all floors. Front entrance w/mudroom area. Convenient to shops, restaurants, schools, public transp’n, Longwood Medical, downtown.

$2,999,999 Active

71 Greenough St 71-1 Brookline, Massachusetts

3 Beds 4 Baths 2,552 SqFt

Experience luxury in this newly completed custom home by a renowned local builder. Ideally situated in the highly desirable Brookline/Chestnut Hill neighborhood, this residence offers the perfect blend of upscale living and everyday comfort. The sun splashed main level features an open & airy layout with soaring ceilings & oversized windows that fill the space with natural light. An elegant fireplaced great room flows into a chef’s kitchen featuring a large island & fully equipped butler’s pantry, ideal for entertaining. A versatile flex space serves as a private office or en-suite guest bedroom. The 2nd floor showcases a lavish primary suite with dual walk-in closets & a spa-inspired bath, plus 3 additional spacious bedrooms & 2 full baths. The expansive finished lower level includes 2 additional bedrooms, full bath & a media room, ideal for movie nights or multigenerational living. Moments from shopping & dining at The Shops at Chestnut Hill & The Street, with easy access to Rte 9.

$3,749,000 Active

15 Glenland Brookline, Massachusetts

5 Beds 5 Baths 4,711 SqFt 0.15 Acres

Welcome to The Brook House! This bright and spacious one-bedroom, one-bath residence offers incredible potential for customization. Perched on the 11th floor, the unit features a balcony with sweeping city and treetop views! The open living and dining area is filled with natural light through large sliding glass doors, while the bedroom provides generous closet space. Though the unit would benefit from updates, it presents an excellent opportunity..**This unit also includes an assigned garage parking space**The Brook House amenities include 24-hour security, an outdoor heated pool, fitness center, tennis courts, and on-site management. Bring your vision and make this home your own!**Some photos in this listing have been digitally altered for illustrative purposes.****Buyer is responsible for verifying all information attached herein.**

$572,000 Active

77 Pond Ave 1103 Brookline, Massachusetts

1 Beds 1 Baths 860 SqFt

$2,759,000 Active

80 Vernon Street Unit 1-A Brookline, Massachusetts

3 Beds 3 Baths 1,662 SqFt

Renovate or build new, on one of Brookline’s most desirable and picturesque streets and sought after neighborhoods. Existing GLA of nearly 5k sqft (988 finished basement), or build 4396 sqft by right on upper floors. Survey and existing conditions plans are available. Demo hold expires October 2025

$2,295,000 Active

3 Glenoe Rd Brookline, Massachusetts

4 Beds 5 Baths 4,855 SqFt 0.4 Acres

$1,999,000 Active

58 Kent U404 Brookline, Massachusetts

2 Beds 2 Baths 1,189 SqFt

An exquisite stucco residence nestled in the coveted Chestnut Hill neighborhood of Brookline. Its hilltop location with stunning terraced grounds provides seasonal views of the reservoir and iconic Boston skyline. This property boasts a clay tennis court and completely renovated interior with a geothermal HVAC system and heated 3-car garage. The cook's kitchen with breakfast area and French doors lead to an elegant stone patio and backyard oasis. The spacious formal living and dining rooms, wood paneled library and family room complete the elegant main level. The seven bedrooms include a primary suite with dual bathrooms and dressing rooms. The third floor has a generous two-bedroom guest suite. The unique walkout lower level is extraordinary and features the original carriage house restored with an illuminated brick barreled ceiling, an unparalleled stone entertainment room and additional bedroom suite. Experience luxury living with the convenience of Boston's vibrant lifestyle.

$5,195,000 Active

40 Heath Hill St Brookline, Massachusetts

7 Beds 8 Baths 6,560 SqFt 0.72 Acres

1BR with balcony at Brook House, a prime location right across from Brookline Village T Station, offers easy access to Longwood Medical Area, downtown Boston, and nearby universities. This well-maintained building features amenities, including 24-hour security, onsite management, package service with notifications, an outdoor swimming pool, a fitness center, a clubroom, tennis and basketball courts, and a courtyard with grills and seating areas. Excellent opportunity for both homeowners and investors!

$530,000 Active

33 Pond Ave 422 Brookline, Massachusetts

1 Beds 1 Baths 850 SqFt

COOLIDGE CORNER ~NEW PRICE!! Urban convenience and functionality merge in this turn-key 2-bed/2-bath condo in famed Coolidge Corner! Open concept Living/Dining Room with Hardwood Floors lead to a private balcony. Exquisitely handcrafted built-in Bookcases and Curio Cabinets span two walls, offering prime display space for your books and collectables. Modern galley kitchen with integrated appliances, designer tile backsplash and quartz counters (2015), updated bathrooms with floating vanities (2015), and thermal replacement windows throughout (2018), including a sliding glass door to private deck. Full-size stackable washer/dryer (2025), Generous closet space, Central Air & Heat. One outdoor exclusive-use parking space included. Small Pets are considered. *EZ commute via Beacon St "T" to Longwood Medical Area & downtown Boston. *Buyers are encouraged to do their own due diligence prior to making an offer. *Sold As Is.

$995,000 Active

51 John St 201 Brookline, Massachusetts

2 Beds 2 Baths 1,050 SqFt 0.23 Acres

SPECTACULAR NEW CONSTRUCTION FLOOR-THROUGH WITH GREAT OUTDOOR SPACE. Flooded with natural light from all sides, this stunning new 4-bedroom, 3-bath home blends luxury, modern elegance, & functional space. It features high ceilings, white oak floors, a fireplace, heated bathroom floors, and a gorgeous chef’s kitchen with Thermador appliances and generous counters. And right off the kitchen is a 475sqft deck—perfect for dining, entertaining, or relaxing outdoors—that also leads to a small yard in back. The primary suite offers corner windows and walk-in closets, and the fourth bedroom has an adjacent full bath, both behind a pocket door, making it ideal as an office, den, or private guest suite. The condo is super energy efficient, and has two-car EV-ready garage parking, extra storage, and a state-of-the-art access system that grants entry by code, phone, fob, or facial recognition. Steps to everything Coolidge Corner & Brookline Village have to offer, this one has it all!

$2,695,000 Active

24 Auburn 1 Brookline, Massachusetts

4 Beds 3 Baths 2,207 SqFt

Experience the best of classic charm and modern convenience in this beautifully appointed 2-bedroom condo. As you enter, a spacious foyer with a coat closet provides a stylish and functional welcome. High ceilings and recessed lighting enhance the bright, open floor plan, which includes a sun-drenched living room and a dedicated dining area. The generous kitchen is a home chef's dream, boasting ample cabinet space, a full set of appliances, and a walk-in pantry. Enjoy your mornings or unwind in the evenings on the private wraparound porch, a perfect spot for entertaining or creating a small garden sanctuary. In-building private laundry and additional storage space add to the convenience. Nestled in a prime quiet location, this home is just across the street from the Roland Hayes School and a short distance (0.6 miles) to Cleveland Circle and the Reservoir MBTA Station, giving you easy access to the Green Line and local bus routes. Short drive to the Longwood Medical area.

$825,000 Active

59 Ackers Ave 1 Brookline, Massachusetts

2 Beds 1 Baths 1,128 SqFt

Bright one-bedroom, one-bath condo with tree-top views, updated kitchen and bath, and new flooring throughout. Enjoy the convenience of a dedicated parking space plus resort-style amenities including pool, tennis courts, concierge, and on-site supers. Move-in ready in a professionally managed building close to shops, dining, and transportation. Welcome Home.

$519,000 Active

99 Pond Avenue D -608 Brookline, Massachusetts

1 Beds 1 Baths 765 SqFt

This gorgeous corner unit home is generously laid out over 2,463 sq ft of living all on one level. Conveniently located in the prestigious Longwood Towers, a full service building with 24 hour concierge, close to Longwood Medical Area, public transportation, restaurants and shops. This well laid out condo is flooded with sunlight and views from all windows. The kitchen features chefs kitchen with Sub Zero fridge, Viking stove, a separate pantry with Miele washer/dryer and a sizeable breakfast bar which opens up to an oversized family room & cozy eating nook. The elegant family room & formal dining area are warm and welcoming, perfect for entertaining. There are 4 bedrooms, 4 bathrooms which include the spacious primary bedroom suite with a generous walk in closet and luxurious oversized spa soaking tub with separate room for shower & toilet. 2 valet garage parking spaces included.

$2,650,000 Active

20 Chapel Street B811 Brookline, Massachusetts

4 Beds 4 Baths 2,463 SqFt

This beautiful top level condominium on historic Beals Street in Coolidge Corner is located in one of Brookline’s most coveted and convenient locations. The home is moments to shops, restaurants, the MFA, Fenway Park, Cambridge, Back Bay and the Charles River. This exquisitely renovated 5 bed/3 bath condo is drenched in natural light with soaring cathedral ceilings and fine craftsmanship throughout. The chef’s kitchen boasts Viking and LG appliances, an Italian granite island, and wine fridge, flowing seamlessly into expansive living and dining areas perfect for entertaining or relaxing with family and friends. The top-floor primary suite offers treetop views, spa bath with soaking tub, marble shower, heated floors, and custom walk-in closet. Three mahogany decks, 2 parking spaces, 2-zone central A/C, mudroom, and a finished lower level bonus room complete this rare offering with the space, style, comfort, convenience, and location buyers dream of.

$2,599,900 Active

95 Beals Street 2 Brookline, Massachusetts

5 Beds 3 Baths 2,891 SqFt

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