5 Bedroom homes for sale & real estate in Brookline, MA

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ABOUT THIS HOME
5 Bedroom Homes for Sale in Brookline, MA
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 o

$3,150,000

5 beds4.5 baths3,838 sq ft

757 Washington St Unit 2 - PH, Brookline, MA 02446

Gut renovated • Open floor plan • Period details

ABOUT THIS HOME
5 Bedroom Homes for Sale in Brookline, MA
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 l

$2,995,000

5 beds4 baths3,450 sq ft

90 Addington #1, Brookline, MA 02445

Total gut renovated • Generous deck • Primary suite

3D WALKTHROUGH

ABOUT THIS HOME
5 Bedroom Homes for Sale in Brookline, MA
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 flex

$2,000,000

5 beds3.5 baths2,460 sq ft

184 Rawson Rd, Brookline, MA 02445

Induction range • Corner townhouse • Composite decks

ABOUT THIS HOME
5 Bedroom Homes for Sale in Brookline, MA
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 pai

$5,000,000

5 beds4.5 baths6,419 sq ft

540 Chestnut Hill Ave, Brookline, MA 02445

Inviting foyer • Acre of land • Serene terrace views

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ABOUT THIS HOME
5 Bedroom Homes for Sale in Brookline, MA
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 soak

$2,599,900

5 beds3 baths2,891 sq ft

95 Beals St #2, Brookline, MA 02446

Coveted location • Chef's kitchen • $250 HOA

Property at 15 Glenland, Chestnut Hill, MA 02467, 5 beds, 4.5 baths

$3,749,000

5 beds4.5 baths4,711 sq ft

15 Glenland, Chestnut Hill, MA 02467

Property at 16 Garrison Rd #7, Brookline, MA 02445, 5 beds, 2 baths

$880,000

5 beds2 baths1,413 sq ft

16 Garrison Rd #7, Brookline, MA 02445

Property at 382 Lee St, Brookline, MA 02445, 5 beds, 5.5 baths

$5,995,000

5 beds5.5 baths6,841 sq ft

382 Lee St, Brookline, MA 02445

Property at 138 Woodland Rd, Chestnut Hill, MA 02467, 5 beds, 5.5 baths

$9,495,000

5 beds5.5 baths7,096 sq ft

138 Woodland Rd, Chestnut Hill, MA 02467

Property at 34 Lagrange St, Chestnut Hill, MA 02467, 5 beds, 3.5 baths

$2,895,000

5 beds3.5 baths5,076 sq ft

34 Lagrange St, Chestnut Hill, MA 02467

Property at 21 Sargent Crossway, Brookline, MA 02445, 5 beds, 6.5 baths

$8,000,000

5 beds6.5 baths5,772 sq ft

21 Sargent Crossway, Brookline, MA 02445

Property at 84 Winthrop #1, Brookline, MA 02445, 5 beds, 4.5 baths

$2,798,000

5 beds4.5 baths3,898 sq ft

84 Winthrop #1, Brookline, MA 02445

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ABOUT THIS HOME
5 Bedroom Homes for Sale in Brookline, MA
Welcome to 206 Franklin St - a timeless Victorian beauty, where history meets modern luxury on a rare half acre corner parcel in Newton Corner. Built in 1890 and re-imagined for the 21st Century, step inside and find an elegant, sun-drenched 4,500 SF home complete with classic designs and modern finishes including a grand hallway, living room, den, spacious dining room, butler's pantry and 4 fireplaces. The bespoke chef's kitchen is a culinary showstopper, anchored by a gleaming granite island, custom cabinetry and everything you need to cook, gather and celebrate. The 3rd floor master suite is a private retreat beneath cathedral, skylit ceilings, complete with fireplace, sitting area, priv

$2,495,000

5 beds4 baths4,500 sq ft

206 Franklin St, Newton, MA 02458

Custom cabinetry • 4 fireplaces • Granite island

3D WALKTHROUGH

ABOUT THIS HOME
5 Bedroom Homes for Sale in Brookline, MA
Rarely available two-family on a fabulous Allston side street, literally 1 house from the Brookline line, has been cherished by 1 family for almost 50 years. Perfect for a new owner, investor, or condo conversion. The first-floor unit offers hardwood floors, high ceilings and oversized windows with 2 spacious bedrooms, living room and eat-in kitchen. The second unit spans two levels with 3 bedrooms, flexible space, and great natural light. There are hardwood floors hiding under the carpets. Both units need cosmetic updates, but offer strong potential while maintaining the beauty of original character throughout. Enjoy yard space, 1 parking and full basement. Superb walk score and biker's pa

$1,300,000

5 beds2 baths2,644 sq ft

5 Fiske Ter, Allston, MA 02134

Natural light • Eat-in kitchen • High ceilings

ABOUT THIS HOME
5 Bedroom Homes for Sale in Brookline, MA
Rare opportunity to own a large Jamaica Plain single-family home with 5 bedrooms, 2.5 bathrooms, and nearly 2,200 sq. ft. of living space across three floors for under $900K! This timeless home is a freshly painted blank slate, blending historic charm with modern functionality, waiting for the next owner to put their touch on it. A flexible floor plan with soaring ceilings allows for multiple uses for an investor, owner occupant, or commercial/retail space. Previously rented for approximately $5K/month, and has the potentially to be converted to a 2 family home for the next owner to live in and collect rent. The unfinished basement has plenty of ceiling height to convert to finished space.

$819,000

5 beds2.5 baths2,119 sq ft

3 Atherton St, Roxbury, MA 02119

Boiler replaced • Flexible floor plan • Unfinished basement

ABOUT THIS HOME
5 Bedroom Homes for Sale in Brookline, MA
This contemporary masterpiece embodies modern luxury—deceivingly understated from the front yet unfolding into a stunning four-level estate of architectural brilliance. Custom built with every imaginable feature, the home showcases 18+ rooms of exquisite craftsmanship and design. Step through grand double doors into a world of custom millwork, built-ins, and refined finishes. The main level is anchored by a 1,500+ sq. ft. primary suite with a paneled office, spa bath with steam shower and soaking tub, private water closet, and an extraordinary dressing room. Floor-to-ceiling windows open to a curved balcony overlooking a private resort-style oasis with a pool, hot tub, and pool house.

$7,200,000

5 beds7.5 baths9,136 sq ft

99 Baldpate Hill Rd, Newton Center, MA 02459

Soaking tub • Refined finishes • Custom millwork

ABOUT THIS HOME
5 Bedroom Homes for Sale in Brookline, MA
Rare and spacious 5-bedroom, 2-bath investment property with one deeded parking space conveniently located next to the back door entrance. Prime location just a short walk to the T station!The good-sized kitchen features granite countertops and stainless steel appliances. Renovated in 2019, this property is currently leased at $4,761/month through May 13, 2026, offering strong and stable rental income. Photos were taken prior to tenant occupancy.

$799,000

5 beds2 baths1,409 sq ft

129 Chiswick Rd #6, Brighton, MA 02135

Renovated in 2019 • Deeded parking space • Granite countertops

OPEN SUN, 10:30AM TO 12PM

ABOUT THIS HOME
5 Bedroom Homes for Sale in Brookline, MA
Gut-renovated and transformed into a condominium, this unique residence offers two distinct living spaces under one roof. Enter left to the first-floor unit featuring an open living/dining/kitchen area with in-unit laundry, a bedroom and full bath, plus access to the lower level with additional living space, bedroom, bath, storage, and systems. Enter right to find a second unit: the main level with open living/dining/kitchen, 2 bedrooms, 1 bath, and laundry, plus a third-floor retreat with bedroom, full bath, and two walk-in closets. A separate room off the entry is ideal for a home office or mudroom. Outdoor living is enhanced with a private deck and yard surrounded by trees for privacy. T

$1,895,000

5 beds4 baths3,500 sq ft

21 Francis St #21, Newton Centre, MA 02459

Private deck • In unit laundry • Rental income

Property at 5 Kappius Path, Newton Center, MA 02459, 5 beds, 6 baths

$3,099,000

5 beds6 baths4,825 sq ft

5 Kappius Path, Newton Center, MA 02459

Property at 88 Essex Rd, Chestnut Hill, MA 02467, 5 beds, 6.5 baths

$9,700,000

5 beds6.5 baths8,750 sq ft

88 Essex Rd, Chestnut Hill, MA 02467

Property at 133 Oak Hill St, Newton Center, MA 02459, 5 beds, 4.5 baths

$3,499,000

5 beds4.5 baths5,237 sq ft

133 Oak Hill St, Newton Center, MA 02459

Property at 214 Allandale Rd Unit B, Chestnut Hill, MA 02467, 5 beds, 6 baths

$2,499,000

5 beds6 baths4,617 sq ft

214 Allandale Rd Unit B, Chestnut Hill, MA 02467

Property at 59 Hyde Ave, Newton, MA 02458, 5 beds, 4 baths

$4,995,000

5 beds4 baths5,010 sq ft

59 Hyde Ave, Newton, MA 02458

Property at 41 Juniper Ln, Newton Center, MA 02459, 5 beds, 3.5 baths

$1,998,000

5 beds3.5 baths4,515 sq ft

41 Juniper Ln, Newton Center, MA 02459

Property at 154 Langley Rd #1, Newton Centre, MA 02459, 5 beds, 5.5 baths

$2,289,000

5 beds5.5 baths3,785 sq ft

154 Langley Rd #1, Newton Centre, MA 02459

Property at 85 Gate House Rd, Chestnut Hill, MA 02467, 5 beds, 5.5 baths

$4,375,000

5 beds5.5 baths8,000 sq ft

85 Gate House Rd, Chestnut Hill, MA 02467

5 Bedroom Homes for Sale in Brookline

There are currently 12 5 bedroom homes in Brookline. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Brookline stay on the market for 49 days and receive 1 offers. Popular neighborhoods include Jamaica Plain, Roslindale, Fenway-Kenmore, Brighton, Mission Hill, Allston, South Brookline, Chestnut Hill, West Roxbury, and Coolidge Corner. This map is refreshed with the newest listings in Brookline every 15 minutes.

In the past month, 44 homes have been sold in Brookline. In addition to houses in Brookline, there were also 153 condos, 18 townhouses, and 10 multi-family units for sale in Brookline last month. Brookline is a fairly walkable city in Norfolk County with a Walk Score of 81. Brookline is home to approximately 59,627 people. Find your dream home in Brookline using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Brookline are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Brookline. Our Brookline real estate stats and trends will give you more information about home buying and selling trends in Brookline. If you're looking to sell your home in the Brookline area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Brookline with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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