Longwood

The Longwood neighborhood in Brookline offers a blend of residential serenity and urban convenience. This historic area has a distinctive character defined by its Greek revival architecture, and further accentuated by the stunning Beech Trees on the Longwood Mall, a historic park that is a centerpiece of the neighborhood - but not the only one.

Real estate in Longwood is a mix of handsome brownstones, spacious single-family mansions, and modern condominiums. The value of the homes reflects the desirability of the location, the quality of the local schools, and the proximity to Boston's world-class hospitals. Buying real estate in Longwood is competitive, with homes generally selling quickly and often above asking price.

The proximity of Longwood is one of its most appealing features, particularly attractive to older professionals and those looking for a quiet neighborhood close to Boston. It's a place where the pace of life slows down at night, despite being along the easternmost part of Brookline, putting it closest to Boston.

The three main streets of the Longwood neighborhood are Beacon Street, Longwood Avenue and Aspinwall Avenue with Kent Street running across all three. Longwood borders Coolidge Corner, Cottage Farm, Brookline Village and St. Mary’s.

The public transportation options, including the D Branch of the MBTA green line with a stop right in Longwood, as well as the nearby C Branch's Kent Street and Hawes Street stops, make commuting and traveling to other parts of Brookline, Boston and Newton seamless​​.

While Longwood does not contain a wide array of restaurants and shops within its confines (residents typically venture to the neighboring Coolidge Corner, Saint Mary’s, Brookline Village, or Fenway areas for such amenities) it does not detract from the neighborhood's charm. Instead, it adds to the peaceful, residential quality that defines Longwood.

Longwood homes are in the Lawrence Elementary School district, a Kindergarten through 8th grade public school that borders Longwood Ave, Kent Street, Stearns Road, and Francis Street, and is tucked away from the main streets that surround it. For families with younger children, various daycare options are available in nearby Coolidge Corner and Brookline Village, ensuring that even the youngest residents are well-catered to.

Parks in and around Longwood are well-maintained and provide a lush backdrop for the area’s stately homes, offering residents a place of peace and tranquility. In addition to the aforementioned Longwood Mall, the Riverway is another highlight of the area featuring a long stretch of walking trail that’s perfect for watching ducks swim, walking a dog, jogging, or simply sitting on a bench and enjoying being surrounded by trees in an urban setting. The Riverway is part of the Emerald Necklace system of parks and parkways designed by Frederick Law Olmsted in the 1890s.

The close proximity to some of Boston's best medical facilities makes Longwood an ideal location for healthcare professionals or those who wish to be near these institutions for personal reasons.

Living in Longwood allows you to enjoy the best of both worlds - peaceful residential living at night with the convenience of urban life just a short distance from your front door.

Home Values

The diversity of real estate in Longwood is perhaps most evident when you compare the streets surrounding Longwood Mall with a main street like Longwood Avenue or some of the impressive brownstones that line Marshal Street. For example, the average single family home on Beech Road was assessed at $4,675,483 in fiscal year 2025 while a home on Marshal Street (one of our favorite streets in Brookline because of its ideal location and beautiful brownstones), where condos outnumber single family homes 9 to 1, was worth $1,368,062.

Below is a list of the most valuable streets in the Longwood area:

• Beech Rd.: $5,595,375
• Borland St.: $3,594,167
• Chatham Cir: $3,658,700
• Chatham St.: $4,345,363
• Colchester St.: $4,150,607
• Hawes St.: $4,583,790

*The above noted 2025 Assessed property values include a mixture of residential property types (condos, single family homes and multi-family properties).

Notable 2024 Longwood Homes Sold

• 32 Borland St.: $4,250,000
• 7 Hawes St.: $4,100,000
• 40 Hawes St.: $3,900,000

Public Transportation

The D train of the MBTA green line stops at Longwood, and from there the next stop inbound takes you to Boston, while outbound makes another four stops in Brookline before it stops at various points in Newton.

In addition, the C line train on the green line makes stops along Beacon Street at Kent Street and Hawes Street. The inbound train gets you to downtown Boston in about 10 minutes, while the outbound train continues along Beacon Street en route to Cleveland Circle with stops at Coolidge Corner, Summit Avenue, Washington Square, and a few others along the way.

Schools

• Lawrence School: Highly regarded public elementary school known for its strong academic programs and a warm, community-focused environment that serves students from kindergarten through eighth grade.
• Brookline High School: Located about a mile from Longwood, BHS is known for its exceptional academic programs and diverse student body. The school prides itself on offering a wide range of advanced placement courses, extracurricular activities, and has a strong focus on inclusive education.
• St. Mary's of the Assumption School: Catholic elementary school in neighboring Saint Mary’s neighborhood that prides itself on its rich tradition of Catholic education that supports and guides students with intentional academic and moral development.

Restaurants & Eateries

Foodies can enjoy a variety of cuisines all within a short distance of the Longwood neighborhood. The closest restaurants are in the Saint Mary’s area and across the Riverway on Longwood Avenue by the hospitals in Boston. There are also a number of excellent options in the Fenway area of Boston, which is less than a mile away.

• Bar 'Cino: This hot-spot is filled nightly and serves delicious Italian food from shared-plates, pizza, piadine, pasta, salads and more.
• Taberna de Haro: This long-standing Spanish tapas restaurant offers a large selection of wine in a cozy atmosphere in the Saint Mary’s neighborhood. And it has a large outdoor seating area that’s great for people watching.
• Cafe Landwer: Just over the Brookline border in Boston, on Beacon Street, this low key Mediterranean restaurant creates healthy & hearty breakfasts, lunches, and dinners. Make sure to try the hummus!
• Matsu-Nori: Small and unassuming hand roll bar serving some of the freshest sushi in Boston.
• Time Out Market: Food court in Fenway with a number of tasty options. And with Trillium Brewery right outside, this is a fun place to grab some food and sample a beer from one of New England’s most popular local brewers.
• Clover Food Lab: Organic, just-cut, local food that’s good for you, good for the planet, and tastes great.
• Eastern Standard: Happening scene serving creative cocktails & modern brasserie fare in a great atmosphere.

Coffee Shops

• Tatte: Great place to sit outside on a nice day and enjoy a drink, pastry or hearty food.
• Caffé Nero: Located on Longwood Avenue in the Longwood Medical area, this is a popular place for medical professionals to grab a caffeine jolt.

Daycares

• Longwood Medical Area Child Care Center: Established to meet the child care needs of employees of participating Longwood Medical and Academic Area (LMA) institutions. Also offers care to community members when slots are available.
• Little Children Schoolhouse: Three locations in the Brookline Village area.
• Everbrook Academy: Multiple locations in nearby Coolidge Corner make this a popular choice.

Supermarkets

• H-Mart: This newcomer to the area replaced the former Whole Foods across the street from the Saint Mary’s T-Stop and offers imported packaged foods, ready-to-serve meals, and more.
• Stop & Shop: Conveniently located in nearby Coolidge Corner, this classic supermarket has been a fixture in the neighborhood as long as we can remember.
• Trader Joe's: Right in the middle of Coolidge Corner is this grocery store that is among the most popular in town.
• Star Market: Less than a mile down the riverway towards Boston on Kilmarnock Street, this grocery store has a large parking lot and offers just about everything you could possibly need.
• Target Grocery: Another viable option in Boston, about a mile from Longwood, is Target. This location has a big selection of food.

Shopping and Other Staples

• Down Under Yoga: One of the most popular yoga studios in Brookline offers a variety of yoga types 7 days a week with some of the best teachers in the area.