Brookline Homes for Sale

Welcome to Brookline, Massachusetts—a vibrant town that seamlessly blends urban convenience with suburban charm. Nestled in Norfolk County, Brookline is just a stone's throw from downtown Boston, making it an ideal location for those seeking a lively community with easy access to the city’s rich cultural offerings. With its tree-lined streets, historic architecture, and a plethora of parks, Brookline is not just a place to live, but a place to thrive.

Brookline boasts a diverse array of homes for sale that cater to various lifestyles and preferences. From charming single-family homes with classic New England character to modern condominiums with contemporary finishes, there’s something for everyone. Families will appreciate the highly-rated public schools and the abundance of recreational facilities, while young professionals will enjoy the vibrant dining and shopping options just minutes away.

As you explore the homes for sale in Brookline, you’ll find properties that reflect the town’s unique charm and character. Many homes feature spacious layouts, beautiful gardens, and access to public transportation, making commuting a breeze. The local real estate market is competitive, but with the right guidance, you can find your dream home in this delightful community.

Whether you’re looking to buy your first home, invest in a property, or find a cozy place to retire, Brookline offers a welcoming atmosphere and a strong sense of community. Don’t miss your chance to be part of this exceptional town—explore the homes for sale in Brookline today and discover your perfect match!

Newest Brookline Homes for Sale

$2,850,000

6 Beds ⋅ 4 Baths ⋅ 73558881 MLS

PHOTOS & VIDEO COMING SOON - Discover timeless elegance and exceptional versatility in this beautifully updated 1938 Cape, thoughtfully designed for today's discerning family. Offering 6 bedrooms and 3.5 baths, the home features two primary bedrooms with private ensuite baths, including a sought-after first-floor retreat ideal for multigenerational living, guests, or an au pair. The chef's kitchen is appointed with stainless steel appliances, a gas range, wall oven, stone countertops, and a center island with seating for three. A welcoming den, formal dining room, and sun-filled breakfast area provide inviting settings for both everyday life and elegant entertaining. The finished lower level offers a versatile recreation room with a dedicated laundry area. Completing the home are an attached two-car garage and two additional off-street parking spaces, blending classic New England charm with modern comfort and convenience.

44 Valley Rd, Brookline

Listing courtesy of Listing Agent: The Kelleher Spalding Team from Listing Office: Gibson Sotheby's International Realty.

$3,650,000

7 Beds ⋅ 5 Baths ⋅ 73558672 MLS

Nestled on one of Fisher Hill's most coveted tree-lined streets, this distinguished Colonial seamlessly blends the warmth and craftsmanship of the early 1900s with thoughtfully designed modern updates. Beautifully maintained and set on a professionally landscaped level lot, the home offers 4,726 square feet across four finished levels with 13 rooms, 7 bedrooms, 4.5 baths, a garage, and ample additional parking. Designed for both everyday living and exceptional entertaining, a stunning kitchen and family room addition serves as the heart of the home. The chef's kitchen features custom cabinetry, three sinks, two dishwashers, double ovens, a gas cooktop with grill, 3 skylights and a sun-filled office nook with vaulted ceilings. The adjoining family spaces flow effortlessly outdoors, while the elegant front-to-back living room opens to a spacious south facing side deck with views of the backyard. There are 4 bedrooms, 2 baths and laundry on the 2nd floor, which includes the primary bedroom with a beautiful fireplace and spa-like bath. 3rd floor offers 2 bedrooms and a full bath. The walkout lower level expands the home's versatility featuring a family room, kitchen, bedroom, full bath with W/D and radiant heat, adjoining to the sitting room with a dining area. There is direct access to the backyard offering excellent flexibility for guests, extended family, or potential ADU use (subject to applicable approvals). Seven bedrooms provide exceptional flexibility for today's lifestyle, including home offices, guest accommodations, or multigenerational living. Ideally situated near Runkle School, Brookline High School, the MBTA Green Line (D Branch), and the Longwood Medical Area, this is a rare opportunity to own a home that masterfully combines historic elegance, modern comfort, and an exceptional Fisher Hill location.

111 Clinton Road, Brookline

Listing courtesy of Listing Agent: The Margie and Jon Team from Listing Office: Gibson Sotheby's International Realty.

$995,000

3 Beds ⋅ 2 Baths ⋅ 73556320 MLS

Nestled on a quiet street in South Brookline, this charming, multigenerational, home near the Brookline Country Club and Larz Anderson Park, this home provides an opportunity for any investor or family looking to buy in Brookline. The character and charm present a unique opportunity to create your own dream home. The property features hardwood floors throughout. Upon entering, you are greeted to a spacious living room, a functional kitchen, a half bathroom, a dining room, and a sunroom that overlooks your gorgeous backyard perfect for relaxing or entertaining the kids! The second level has a full bathroom, 2 decent size bedrooms and one large bedroom. Basement has lots of storage an attached garage, and one tandem parking space in front. With some TLC this could be your beautiful home and have the wonderful Brookline School District.

25 Leland Rd, Brookline

Listing courtesy of Listing Agent: Vena Priestly from Listing Office: Rise Signature Homes.

$1,999,000

4 Beds ⋅ 3 Baths ⋅ 73552349 MLS

Chestnut Hill - Baker School neighborhood. This 9-room brick Tudor pairs classic architectural charm with 3,123 square feet of updated living space, offering 4 bedrooms, 2.5 bathrooms on three levels. A beautifully updated eat-in kitchen, gracious living room with ornate fireplace and dining room set the stage for elegant entertaining. A first floor great room with vaulted ceiling opens to a 31'x19' patio and private backyard. Handsome masonry work throughout the beautifully landscaped outdoor spaces. The finished lower level features a family room with fireplace and stone surround. Direct access garage parking. A prime location near Chestnut Hill shopping and dining. Easy access to Cambridge, Boston, area hospitals and universities.

142 Beverly Rd., Brookline

Listing courtesy of Listing Agent: Friedler / Marchant Living Group from Listing Office: Hammond Residential Real Estate.

$2,750,000

5 Beds ⋅ 6 Baths ⋅ 73550700 MLS

This pristine, move-in ready residence offers the best of Brookline with easy access to transit, parks, restaurants, shopping, universities, museums, and the Longwood Medical Area. In the heart of Corey Hill, Coolidge Corner, and Washington Square this property was expertly transformed in 2016 from a multifamily into a stunning multilevel single-family home. The home showcases exceptional craftsmanship and thoughtful design throughout. Oak floors throughout, custom built-ins, two gas fireplaces, and an open-concept kitchen with upgraded appliances, double oven, create inviting spaces for everyday living and entertaining. Every bedroom features an ensuite bath, while two kitchenette areas and a walkout lower-level suite offer exceptional flexibility for multigenerational living, guests, or work-from-home needs. A spacious deck, low-maintenance lot, and two-car garage complete this remarkable home.

16 York Ter, Brookline

Listing courtesy of Listing Agent: Wendy Rocca from Listing Office: Keller Williams Realty Boston Northwest.

$4,495,000

5 Beds ⋅ 5 Baths ⋅ 73550033 MLS

SARGENT ESTATES! Privately set on approximately 1 acre in Brookline's coveted neighborhood, this exceptional contemporary residence offers over 6,800 square feet of light-filled living space surrounded by mature trees & natural beauty. A winding drive leads to this 5+ bedroom, 4.5-bath home featuring soaring ceilings, expansive walls of glass & seamless indoor-outdoor living. The custom kitchen opens to an impressive 720-square-foot living and dining room with fireplace & dramatic ceilings, flowing to an expansive deck overlooking the tranquil grounds & swimming pool. The first floor also includes 2 bedrooms, 2 full baths & a half bath. Upstairs, the private primary suite offers an updated bath, walk-in closet, office, sitting room & oversized deck. The walk-out lower level features a large recreation room, playroom, exercise room, 2 bedrooms an office & a full bath. A two-car garage completes this remarkable property just minutes from schools, shops, hospitals & downtown Boston.

108 Codman Rd, Brookline

Listing courtesy of Listing Agent: Jamie Genser from Listing Office: Coldwell Banker Realty - Brookline.

$1,995,000

4 Beds ⋅ 3 Baths ⋅ 73549795 MLS

Fantastic move-in-ready 4 bedroom, 2.5 bathroom in Chestnut Hill. Set on a 15,000+ level private lot, close to schools, shops, restaurants, public transportation, golf & Skyline Park with its trails, playgrounds, fields and other amenities. Filled with natural light, the main level has beautiful hardwood floors throughout, a fireplaced living room, lovely dining room, stainless and granite eat-in kitchen, family room, home office and guest bathroom. Upstairs are 4 very generous bedrooms. and a full hallway bathroom.The primary bedroom has vaulted ceilings, sky lights and, in addition to the large ensuite bathroom, a second separate dressing room with its own sink and vanity. The home's lower level has high ceilings and unlimited potential to be used as a gym, movie theatre or what ever your needs maybe. There is central a/c.The backyard is level and private, with an expansive deck off the kitchen and family room for entertaining. A 2 car garage and large driveway complete this offering

75 Hammond Pond Parkway, Brookline

Listing courtesy of Listing Agent: Amy Sassoon from Listing Office: Coldwell Banker Realty - Brookline.

$1,888,000

3 Beds ⋅ 3 Baths ⋅ 73548945 MLS

**PRICE IMPROVEMENT**Nestled on a quiet private street in sought after Brookline Village, this updated 3-bedroom, 3 full bath mid-century single family home blends classic character with modern comfort. Just steps from the T, shops, restaurants, and parks, it offers an unbeatable location with everyday convenience. The bright inviting layout features a large living room with a newer roof. Standout 2004 addition, the bright three season sunroom, serves as a wonderful retreat for relaxing or entertaining while enjoying views of the expansive private yard. The home boasts three generously sized bedrooms and three full baths, including a large primary suite with a newer roof. The significant 2005 addition created a partially finished basement that provides excellent flexible space — perfect for a family room, home office, gym, or guest area — while retaining ample storage. Recent upgrades enhance everyday living: a 2023 new mini split system for heat and AC plus a 2025 solar panel installation.

50 Franklin St, Brookline

Listing courtesy of Listing Agent: Richard Knox from Listing Office: RF Boston Realty Group.

$2,399,000

4 Beds ⋅ 3 Baths ⋅ 73547641 MLS

Prepare to be impressed by this beautifully renovated 4 Bed 3 Bath mid-century modern ranch in Chestnut Hill Brookline on the edge of the golf course! Set on over a half acre of beautiful landscaping surrounding the flat back yard lead to the golf course. Breathtaking renovations highlight modern living with soaring exposed beam ceilings, a dramatic living room with a wood-burning fireplace, and a wall of windows overlooking the screened porch, deck, and tranquil Japanese rock garden. The renovated kitchen features sleek cabinetry, updated countertops, appliances, a peninsula, pantry, and eat-in area. The main level offers three spacious bedrooms, including a large primary suite, while the finished walkout lower level includes a great room with kitchenette, fourth bedroom, full bath, studio, bonus room, patio access, and abundant storage. Perfect location with quick access to 9 & I-93 and a quick hop to local restaurants, shopping, Wegman's, and much more!

365 Newton St, Brookline

Listing courtesy of Listing Agent: Rose Hall from Listing Office: Blue Ocean Realty, LLC.

$11,000,000

73543050 MLS

Encompassing just under two acres of wooded, private land, 39 Cottage Street presents an exceptional setting for a custom-built estate in one of Greater Boston's most sought-after communities. Nestled among mature trees and natural landscape, the property offers remarkable privacy and a sense of seclusion while remaining just minutes from Boston and Chestnut Hill's shopping, dining, golf courses, and premier schools. With a scale seldom found in Brookline, the site provides the flexibility to create a truly bespoke residence tailored to your vision. A rare offering where privacy, location, and possibility converge. This lot can also be divided into two buildable lots.

39 Cottage St, Brookline

Listing courtesy of Listing Agent: Maggie Gold Seelig from Listing Office: MGS Group Real Estate LTD.

$2,349,000

4 Beds ⋅ 4 Baths ⋅ 73537709 MLS

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 21, Brookline

Listing courtesy of Listing Agent: Bill Gehan from Listing Office: Campion & Company Fine Homes Real Estate.

$14,995,000

6 Beds ⋅ 8 Baths ⋅ 73537408 MLS

Designed to be admired and built to be enjoyed, 33 Sears Rd is a custom residence set on 1.6 acres of manicured, private grounds. The home makes an immediate statement with a grand two-story foyer that introduces soaring ceilings, refined detailing, and beautifully scaled living spaces throughout. Built by one of Boston's premier female builders, the craftsmanship is evident in every threshold, finish, and room proportion. The open-concept main level was thoughtfully designed to offer grand room sizes without sacrificing warmth. A custom chef's kitchen appointed with top-tier appliances anchors the heart of the home, complemented by a separate, fully equipped prep kitchen. The primary suite features a dramatic two-story walk-in closet, a rare offering that quietly separates this residence from others on the market. Elevator infrastructure is already in place. Outdoor living is equally compelling, w/ ample acreage to accommodate a future pool, sport court, or other lifestyle amenities.

33 Sears Rd, Brookline

Listing courtesy of Listing Agent: The Sarkis Team from Listing Office: Douglas Elliman Real Estate - The Sarkis Team.

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