Skip to search filters Skip to listings

Homes for Sale in Brookline, MA

1 - 30 of 139 available listings

Sort Listings

Though widely considered one of the top Boston suburbs, it does Brookline a disservice to define it solely by its relation to Boston; it is so much more. With excellent schools, a preponderance of independently owned and operated businesses, and a charming blend of homes, shops, and suburban amenities, Brookline is a shining example of the American suburb.

About Brookline, MA

An Overview of Brookline

Though widely considered one of the top Boston suburbs, it does Brookline a disservice to define it solely by its relation to Boston; it is so much more. Ranking and review site Niche awarded Brookline the prestigious rank of “Best Suburb in the nation” in 2015, and it routinely ranks among the top options, As of this writing, Brookline ranks in the top 20 to #17 overall nationwide. It is easy to see why. With excellent schools, a preponderance of independently owned and operated businesses, and a charming blend of homes, shops, and suburban amenities, Brookline is a shining example of the American suburb.

Homes for Sale in Brookline, MA Neighborhoods

According to its neighborhood associations, the city of Brookline is comprised of 19 or so different neighborhoods, though where one begins and the next ends can be a nebulous affair. While there is some geographical and cultural overlap between them, each neighborhood has its own distinct traits that set it apart.

From single-bedroom condominiums to luxurious estates, homes for sale in Brookline, MA do not tend to stay on the market long. The homes mentioned in this article are not hypothetical examples. As of the time of this writing, each is a real property that you can find on Due to the high demand, homes for sale in Brookline, MA may have higher or lower prices than shown in this article. Think of the examples as a guidelines or starting points. Rough estimates of the range available in Brookline’s different neighborhoods will help you better gauge which neighborhoods are right for you.

Aspinwall Hill

Located between Corey and Fisher hill, this neighborhood takes its name from Dr. William Aspinwall, who first purchased the land in 1788. Beaconsfield Terraces give Aspinwall Hill its distinctive appearance. Builders constructed these homes towards the end of the 19th century. Residents call them “castle buildings” due to their rounded turrets, stained glass windows, and overall prominence of their stonework.

Just a short trip from the Beaconsfield and Washington Square Green Line T stops, anyone looking at homes for sale in Brookline, MA’s Aspinwall Hill neighborhood owes it to themselves to go shopping on Beacon Street. After a fun shopping trip, swing by Schick Park at the top of the hill for a taste of what living in Aspinwall Hill would be like.

With listings ranging from high-rise condominiums under $700,000 to gorgeous colonials in the $2M range, has some amazing homes for sale in Brookline, MA’s Aspinwall neighborhood.

Brookline Village

Home of Brookline’s earliest restaurants and shops, as well as America’s first municipal gymnasium, Brookline Village is the heart of Brookline’s history. Today, it packs an eclectic mix of cafes, antique shops, and other storefronts in its tasteful blend of old and new, vintage and modern.

Pill Hill Historic District

Also known as, High Street Hill, the Pill Hill Historic District owes its name to its proximity to the Longwood Medical Center. In addition, a large number of residents involved in the health care professions live there. While residences include some truly expansive stand-alone homes, there are condominiums and apartments for sale in High Street Hill as well. Though vacancies are infrequent, these units offer surprising value. With their excellent amenities and desirable location, they are occasionally among the most affordable homes for sale in Brookline, MA.

Buttonwood Village

Nestled between The Country Club and Larz Anderson Park, Buttonwood is home to the Allendale Farm, the last colonial working farm in Greater Boston and a fantastic source of fresh, local produce. The park is 64 acres of gorgeous land, boasting picnic and barbeque spots, athletic fields, a skating rink, and fantastic views. Its scenic vistas make it a popular choice for weddings and celebrations. Do not wait for a special occasion to enjoy views of the Boston skyline. They are special in and of themselves.

When looking at homes for sale in Brookline, MA, Buttonwood Village holds numerous colonials from the 1950’s and a scattering of Victorian houses sprinkled throughout.

Chestnut Hill

If shopping is your thing, eventually you will find yourself in Chestnut Hill. Between The Chestnut Hill Shopping Center and The Mall at Chestnut Hill, Brookline plans to expand this shopping destination even further with the addition of Chestnut Hill Square. In addition, the neighborhood is home to Boston College, whose Collegiate Gothic buildings lend an air of sophistication to the landscape.

Brookline’s western gateway, Chestnut Hill’s residential spaces blend luxurious condominium developments, scenic homes, and impressive estates. The neighborhood also hosts a vast array of shops, offices, grocers, high-end clothiers, designers, and more. With some of the most luxurious homes for sale in Brookline, MA, Chestnut Hill is an excellent choice if you are looking for the very best homes for sale in Brookline, MA.


Suburban and proud, Putterham is not organized around shopping and dining centers as much as with excellent residential living. A small neighborhood tucked between South Brookline and the rest of Chestnut Hill, this neighborhood is famous for the Putterham School, a one-room schoolhouse built in 1768. A historical landmark, 1966 saw the schoolhouse move from its Grove Street origins to Larz Anderson Park, where it persists to this day as a museum.

Modern Putterham has little in the way of commercial buildings. However, The Shops at Putterham , a strip mall surrounded by residential properties, provides groceries, restaurants, and the all-important coffee shop to residents.

South Brookline

Nestled within Chestnut Hill, the gorgeous estates and verdant green hills of South Brookline create a rare, genuinely open space. John Goddard, one of South Brookline’s first citizens, played a pivotal role in the American Revolution by storing military supplies in his barn, and distributing them to revolutionaries. It is also the home of The Country Club, the first country club established in the United States back in 1882.

More than just a historical neighborhood, South Brookline arguably hosts the cream of the crop when it comes to homes for sale in Brookline, MA. Even by the high standards of Chestnut Hill, if you are looking for your dream home in Greater Boston, you owe it to yourself to look through South Brookline.

Coolidge Corner (South Side)

Head to the corner of Beacon and Harvard Streets, and the palatial Tudor-style S. S. Pierce Building will greet you. Housing several stories of offices with a commercial ground level, the building is emblematic of Coolidge Corner’s artful blending of historic class and modern shopping. The 1920s brought a second construction boom to Coolidge Corner, resulting in the gorgeous Art Deco Bank (currently housing a Bank of America branch), and the two-story Arcade Building two blocks to the north. Head across Beacon Street and you will find yourself in North Brookline. With a Green Line C stop, as well as the #66 bus, public transportation to and from Coolidge Corner is easily accessible. Though unlike other shopping destinations, such as Downtown Boston, Coolidge Corner is automobile-friendly with parking to spare.

When looking at homes for sale in Brookline, MA, Coolidge Corner is a remarkably attractive neighborhood for anyone looking to live near a shopping destination. Finding an available listing is significantly easier than in say, Chestnut Hill. From cozy single-bedroom condos in the mid-$400k range, to spacious multi-bedroom homes in the low seven figures, Coolidge Corner’s south side neighborhood offers a range of options at comparatively accessible price points. These are remarkable prices for homes for sale in Brookline, MA.

Cottage Farm

Purchased by David Sears II in 1820, this 119-acre territory became a lovely residential neighborhood with homes designed in Queen Anne and Gothic Revival styles. According to the Brookline Historical Society, Sears looked to provide “gracious, comfortable home(s) in a rural setting,” and his vision is alive and well in modern Cottage Farm. More or less a part of Coolidge Corner, it takes steps toward small-town solitude and peaceful shady streets while still retaining all of the convenience of Coolidge Corner’s excellent location.

JFK Crossing

Blending both suburban and urban qualities, JFK is around Harvard Street between Naples and Verndale. The neighborhood’s namesake, 35th president of the United States, John F. Kennedy, was born at 83 Beals Street, just around the corner in North Brookline. JFK Crossing has four bright murals, brick and stone buildings, and shady side streets providing Brookline’s signature arboreal canopy. With relatively few apartment complexes compared to other neighborhoods, homes for sale in Brookline, MA, JFK Crossing is perfect for anyone who wants to live in a verdant, tree-lined suburb with great independent restaurants, shops, and craft stores literally around the corner.

Fisher Hill

As one of Brookline’s more secluded areas, this upscale residential neighborhood sits next to the Fisher Hill Reservoir. Alternately known as Brookline Hill, Henshaw Hill, and Mount Vernon, Fisher Hill takes its name from the 1852 estate built by Francis Hill. It is on the corner of Boylston Street and Chestunt Hill Avenue.

Named a Historic District in 1984, Fisher Hill hosts a number of homes built in the 1800s. Unlike many of the counterparts from the era, owners have not converted most of these homes into apartments. They continue to serve their original purposes as stand-alone residences. With the Reservoir T stop in its northwestern corner, Fisher Hill also enjoys Green Line access. It has less-crowded roads and ample parking, offering a relaxing respite from the hustle and bustle of Boston. Some of the most luxurious homes for sale in Brookline, MA have a Fisher Hill address. These include gorgeous brick masterpieces tucked away in a lush copses of trees and shrubs to modern marvels from the cutting edge of residential architecture. If you want the best of the best, this is a fantastic location to start.

Griggs Park

Griggs Field, with 4.17 acres of trails, weeping willows, and a quaint pond, sits at the center of the Griggs Park neighborhood. Living in the Griggs Park historic neighborhood gives residents a slice of country life in view of the Boston Skyline. Living in Griggs Park means that the view from your window opens up to a sea of trees and neighborhoods with a small-town vibration. It is easy to forget how close the T line is as you move through the peaceful enclave of houses and apartment buildings.

Countless residents love living in Brookline because of the slower pace of suburban life within easy access to the amenities of Boston. If you really want to experience that kind of experiential distinction, then of all the neighborhoods with homes for sale in Brookline, MA, Griggs Park should be at the top of your list.


At the far east of Brookline, the neighborhood of Longwood borders the city of Boston. It takes its name from Napoleon Bonaparte’s St. Helena estate. David Sears II purchased the property in the early 19th century with plans to develop it. Building plans generally follow the pattern of urban residential housing surrounding public green space, which date back to the Greek Revival “English Cottage” style that Longwood’s first homes espoused. Longwood also hosts a section of Wheelock College.

With its own T stop on the D Branch of the Green Line, as well as quick access to the Hawes Street C Branch station, Longwood embodies the luxury of living in suburban seclusion, with the convenience of easy access to a big city.

St. Mary’s

On the eastern edge of Longwood, with Boston just across St. Mary’s Street, this neighborhood offers life among lush trees and open spaces. It is also just a few blocks away from Fenway Park. Boasting a Green Line T stop and easy access from Beacon Street with plenty of parking, this location makes it easy to get to and from Boston without the hassle. St. Mary’s is also home to the Brookline Arts center that offers visual arts classes for students of all ages.

Beacon Street has small shops and restaurants sprinkled alongside brownstone apartments. Side streets are lined by the verdant shade from rows of trees, house beautiful freestanding homes. Those looking at homes for sale in Brookline, MA will find a lot to love about this neighborhood. From affordable condos to breathtaking 7-bedroom, 5,200 square foot properties, St. Mary’s is a fantastic neighborhood if you want the best of both worlds right at your doorway.

North Brookline

Up until the construction of the Charles River Bridge in 1786, Harvard Avenue in Brookline provided the primary route to Boston from Cambridge. The coming of the trolley in 1880 transformed this mix of wetlands and farms into what is among the most densely populated neighborhoods in Brookline, MA. A mix of historic homes and newer constructions, North Brookline is easily accessible by the B and C Green Lines, the 57 Bus, and the Massachusetts Turnpike.

Described as the “ultimate mix between suburban and urban living” by the Brookline Historical Society, this neighborhood embodies Brookline’s dual-nature. Even with its higher population density, a quick duck down any of its side streets leads to a secluded retreat among tree-lined streets, historic construction, and rows of secluded homes with plenty of space to go around.

Washington Square

Marked by an 18-foot tall Victorian Restoration clock, Washington Square blends small town charm and modern convenience in an accessible commercial neighborhood. Centered on the intersection of Beacon and Washington Streets and stretching into bits of Aspinwall Hill, Corey Hill, and Corey Farm, Washington Square is home to some of the best restaurants in Brookline, MA. The Fireplace, The Abbey, and Washington Square Tavern are a few of the best. The Washington Square Green Line T station makes transportation in and out of the square a snap.

Of all the areas for homes for sale in Brookline, MA, the Washington Square offers a familiar blend of condominiums and apartments mixed with stand-alone houses down side streets. Ranging from $1.2M colonials on tree-lined streets, to sub-$400K Brownstone apartments, the homes for sale in Washington Square span a wide range. However, it is good to be aware that listings tend to sell quickly in this desirable district.

Corey Hill

Settled by Timothy Corey in 1760, “The Great Hill” rises up to 260 feet above sea level at the Corey Hill Outlook Park, located at the zenith of Summit Avenue. Providing scenic sanctuary from the hustle and bustle of the surrounding area, the paths and trails crisscrossing Corey Hill allow a pleasant and practical way to move around the district.

With most of the neighborhood technically falling under the auspices of Washington Square, Corey Hill is essentially a small neighborhood within a larger one. As with all homes for sale in Brookline, MA, listings in Corey Hill tend to move fast. Combine that with the comparatively small number of homes, moving into this neighborhood can require decisive action. That said, from $700K raised row condos that border Washington Square, to lavish, state of the art $3.2M townhomes at 69 Westbourne Terrace, the available properties run the gamut of price points. This is especially true considering the in-demand nature of the neighborhood.

A Word on Homes for sale in Brookline, MA Historic Districts

Living in any of Brookline’s seven historic districts is a great way to experience the rich history of New England. Carefully preserved by the Brookline Preservation Commission, it is obvious that this is not the place to look for new construction. Indeed, any changes made to these historic structures require first acquiring approval from the Commission. Therefore, if you have plans involving renovation, it might behoove you to look at the other homes for sale in Brookline, MA. On the other hand, there is nothing quite like the experience of living in an expertly maintained historical building. However, know what you are getting into.


At the time of the 2010 census, Brookline, MA was home to 58,732 residents. As of this writing, current estimates place the population around 59,246, with a population density somewhere in the neighborhood of 8,750 people per square mile. Compared with Boston’s 13,894 people per square mile, many residents enjoy the relatively relaxed pace and additional space that Brookline provides.

Notable People from Brookline, MA

Brookline has been home to Larry Bird, Tom Brady, and James Taylor.

That is just the tip of the iceberg. Many famous people have found homes for sale in Brookline, MA and fallen in love with the city. The parade of famous Brookline residents could easily fill the pages of a book. This list is by no means exhaustive. Rather, this is but a glimpse of the many notable individuals who have made Brookline their home.

President John F. Kennedy & Siblings

Arguably, Brookline’s most famous address is 83 Beals Street in Coolidge Corner. It houses the John Fitzgerald Kennedy National Historic Site, which honors our 35th president. Born in Brookline, as were his siblings Eunice, Patricia, Jean, and Bobby, JFK lived in the home for the first ten years of his life. Today, it stands as a monument to his memory.

King Bhumibol Adulyadej

JFK is not the only head of state born in Brookline. The premier of Thailand, His Majesty King Bhumibol Adulyadej, also known as King Rama IX, spent the first year of his life in Brookline. Prince Mahidol Adulyade’s youngest son was born in the United States, while the prince studied medicine at Harvard. Following the tragic death of his father, Adulyadej became the longest-reigning Thai monarch in history. He led Thailand from 1946 until his death in October of 2016, which was a total of 70 years and 126 days.

Conan O’Brian

Born and raised in Brookline, O’Brian took to comedy like a fish to water. As president of The Harvard Lampoon during his days at the prestigious university, he laid the groundwork for an impressive career in the art of making people smile. After writing for Saturday Night Live, and writing and producing for The Simpsons, NBC chose him to be David Letterman’s replacement on Late Night in 1993. After leaving “The Tonight Show”, he embarked on a comedy tour called “Legally Prohibited from Being Funny on Television”. Aside from a brief hiatus, he has been a staple of late-night television ever since.

Harvey Cushing

Known as the “father of modern neurosurgery”, Boston’s Peter Bent Brigham Hospital appointed him surgeon-in-chief in 1911. He became a professor of surgery at the Harvard Medical School in 1912. A true pioneer of brain surgery and the world’s first neurosurgeon, he received the Distinguished Service Medal serving as a colonel in World War I. Being a man of many talents, he wrote the Pulitzer prize-winning Life of Sir William Osler. His revolutionary techniques would go on to shape neurosurgery, as we know it today.

History of Brookline, MA

Some of the earliest accounts of Brookline remark on the natural beauty of the place. Andrew Jackson Downing, writing in the 1841 publication of Theory and Practice of Landscape Gardening, professed that there was nothing so inexpressibly charming anywhere else in America. He waxed eloquently about its verdant lanes and winding streets.

More than Just A Pretty Place

Like most of Greater Boston, Brookline was originally Algonquin territory. Europeans settled it in the early 1600s. Named for the series of ponds and brooks running through the southern boundary of the territory, the Muddy River hamlet eventually incorporated as Brookline in 1705. Brookline has never been part of Boston, and many residents are very happy to remind their neighbors of that point. It was not for a lack of effort on Boston’s part. First, as a community of farms, Brookline’s charms soon made it a destination for Bostonians seeking land to call their own. Farmland became estates for lawyers and other professionals with offices in Boston. That started the morning commutes that many still undertake some two hundred years later.

The Annexation Debate of 1873

As the 1800s rolled on, Boston began annexing its neighbors in earnest. The expanding metropolis swallowed one town after the other. Boston increased its borders by annexing Roxbury in 1868, Dorchester in 1870 and Brighton, Charlestown, and West Roxbury in 1873. Naturally, eyes soon turned to Brookline with the expectation that the growing suburb would follow suit.

However, Brookline had other ideas. Specifically, it was loathe to adopt Boston’s centralized leadership. Brookline preferred to stick with its town meeting governmental model, where citizens voted on all civic affairs with a board of five elected to form the city’s executive branch. Still, with pressure from the larger city, citizens weighed the various pros and cons with great interest and passionately deliberated. The Boston-Brookline annexation debate raged across 1873, with 81% of Boston voting in favor of the measure. Only Brookline’s citizens, however, would decide Brookline’s fate. With a sweeping 70% of the vote, those citizens elected to remain independent.

Scholars such as Kenneth T. Jackson (in his book Crabgrass Frontier, suggests that Brookline’s refusal to be annexed marked the consolidation movement’s first significant defeat. This sparked a chain reaction that would influence suburbs such as Evanston and Oak Park to rebuff Chicago, Brighton and Irondequoit to reject annexation by Rochester, NY, and Piedmont dismissing Oakland, CA’s overtures. This was a seismic shift in the status quo for American metropolitan areas, causing residents, businesses, and politicians to take notice.

The American suburb was not going away any time soon. Thinking of it in the same fashion as a nearby city would do you no favors.

Activism, Railroads, and Streetcars

Brookline continued in its independent, democracy-loving ways, and does so to this day. In 1882, nearly 40 years before the ratification of the 19th amendment, the idea of women’s suffrage was still contentious in much of the United States. In Brookline, however, Benjamin F. Butler of Brookline powerfully advocated for the idea in his campaign to become governor of Massachusetts. While his bid ultimately failed, it brought the ideals that Brookline stood for to a larger stage.

Like the rest of the region, the advent of steam railroads revolutionized Brookline. In the 1830s, the Boston and Worcester Railroad laid tracks through the city of Brookline near the Charles River. The Boston and Albany Railroad came through Brookline village in 1847, extending through Newton in 1852. Over a hundred years later, these same routes would become the “D” Branch of the Green Line.

The late 1800s would also see the introduction of streetcar lines, an innovation that not only lives on in the Green Line’s “C” Branch, but also in the layout of homes and businesses across Brookline. By establishing an identity as a streetcar suburb, Brookline transitioned from horse-drawn carriages to electric trolleys. That paved the way for the automobile-friendly suburb’s modern incarnation.

Real Estate Data on Homes for Sale in Brookline, MA

As of this writing, you can find homes for sale in Brookline MA ranging from a 1-bedroom condominium for $469,000 to five acres hosting a one of a kind 5-bedroom masterpiece built by architect Richard Landry for $39,500,000. That is a large range, to be sure, but the median sale price of roughly $770,000 provides a better indication of the market. Compared to Boston’s median list price figure of $676,000, it is clear that residents are unlikely to choose Brookline over Boston in order to save money.

That said, with a median list price of $650 per square foot, compared to Boston’s median list price of $742, dollars simply go further in homes for sale in Brookline, MA. Residents are taking advantage of that opportunity.

Transportation near Homes for Sale in Brookline, MA

When it comes to getting around, the main difference between Brookline and Boston is the ratio of street traffic and public transportation to driving. One benefit that prospective residents find attractive is the ease of navigation. With plenty of parking and less congestion, this not only makes driving more viable, it is also more pleasant. Fewer overall motorists, combined with space that is more available and parking, allows drivers to take a more relaxed approach behind the wheel.

Public Transportation near Homes for Sale in Brookline, MA

Brookline enjoys access to the C and D branches of the MBTA Green Line, with the B branch running alongside its northern border. With Boston Logan International Airport just seven miles away from the city center,( roughly 40 minutes down Commonwealth Avenue, or about an hour via route D and the Green Line), Brookline residents can travel virtually anywhere in the world from their front door.

While public transit options to and from Boston prove useful, when getting around within Brookline, most residents opt to drive rather than rely on busing or T stations.

Education near Homes for sale in Brookline, MA

Whether you plan to enroll any students or not, an excellent school district says a multitude of good things about a neighborhood. The Public Schools of Brookline serve all homes for sale in Brookline, MA. These schools provide some of the best K-8 education in New England. Baker School and Pierce both receive 9/10 ratings from, Heath, John D Runkle, and Michael Driscoll each ranking an 8/10, and nothing in the district is in below 7/10 at any age range.

Private Schools near Homes for Sale in Brookline, MA does not provide rankings for public schools, though does. By their rankings, Brookline contains three of the top 40 private high schools in all of Massachusetts. These include 6-12 Beaver Country Day School (#26), PK-12 Dexter Southfield School (#37), and K-12 Maimonides School (#39). Each of these schools received a coveted “A+” grade.

Higher Education near Homes for Sale in Brookline, MA

While most would not call it a College town per se, several acclaimed institutes of higher education have a presence in Brookline. Pine Manor College, Hellenic College Holy Cross Greek Orthodox School of Theology, as well as parts of Boston College, Wheelock College, and Parsons Field from Northeastern University, represent post-secondary education within the city limits.

Daily Life in Brookline, MA

Ask past or present Brookline residents about living in the city and they are likely to shower the place with praise. From the excellent school system, to Coolidge Corner’s small businesses and cultural scene, to dining out in Brookline Village or Washington Square, everyone has their favorite part. What virtually everyone agrees on, is that while Brookline might be surrounded by Boston, it feels like its worlds away. Quick access to downtown from a shady, verdant oasis feels like paradise to Brookline citizens. So if that sounds like paradise to you as well, then you owe it to yourself to check out the many and varied homes for sale in Brookline, MA.

Homes for Sale in Nearby Neighborhoods and Towns