27

South Brookline Homes for Sale

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  • /33

    $4,600,000

    • 4 Beds
    • 5 Baths
    • 8,020 Sq Ft

    69 Princeton Rd, Chestnut Hill, MA 02467

    Immaculate 4 bed Colonial on private 1⁄2 acre in prestigious Chestnut Hill. Gated drive leads to landscaped lot w/ mature trees, new deck, patio & large backyard. Over 8,000 sq/ft of fully renovated living space. Stunning 2-story foyer w/ crema marble, Venetian plaster & Serip chandelier. Formal living & dining rooms w/ custom lighting. Great room w/ 15' ceilings & marble fireplace.

    Dave Costello & Scott Accorsin Advisors Living - Boston

    69 Princeton Rd, Chestnut Hill, MA 02467
  • /38

    $6,100,000

    • 5 Beds
    • 5.5 Baths
    • 6,841 Sq Ft

    382 Lee St, Brookline, MA 02445

    Enter the gates into this stunning Colonial-style home in Brookline. Custom-built in 2017, this home features a grand double-height entry that opens to formal living and dining areas. The kitchen is a showstopper, featuring an oversized island, wet bar, multiple beverage centers, and a full suite of Sub-Zero/Wolf appliances. Completing the main floor is a sunny family room off the kitchen leading

    Siu Fu Lau Team Compass

    382 Lee St, Brookline, MA 02445
  • /36

    $8,000,000

    • 5 Beds
    • 6.5 Baths
    • 5,772 Sq Ft

    21 Sargent Crossway, Brookline, MA 02445

    Set in Brookline’s prestigious Sargent Estates, this renovated stately Georgian Colonial offers timeless architecture, peaceful surroundings, and prime access to Boston. Located near top schools, shopping, dining, cultural institutions, the Financial District, Longwood Medical Area, and Logan Airport, it’s ideal for those seeking both elegance and convenience. The exterior features clapboard

    Jonathan Radford Coldwell Banker Realty - Boston

    21 Sargent Crossway, Brookline, MA 02445
  • /42

    $6,100,000

    • 9 Beds
    • 8 Baths
    • 8,619 Sq Ft

    372 Warren St, Brookline, MA 02445

    Fabulous level lot, almost an acre of beautifully manicured grounds with fountain, Koi Pond, stone patios & porches. Stunning 2024 fireplace kitchen w/radiant heat flooring & new enclosed breezeway. Dining room w/double French doors leading to a Greenhouse/Conservatory w/SW exposure overlooking the gardens. Stunning, sophisticated & chic, a large & welcoming sunken living room with fireplace,

    Jill Streck Coldwell Banker Realty - Brookline

    372 Warren St, Brookline, MA 02445
  • /42

    $5,395,000

    • 7 Beds
    • 8 Baths
    • 6,560 Sq Ft

    40 Heath Hill St, Brookline, MA 02445

    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

    Mizner+ Montero Gibson Sotheby's International Realty

    40 Heath Hill St, Brookline, MA 02445
  • /37

    $7,495,000

    • 6 Beds
    • 7.5 Baths
    • 9,380 Sq Ft

    100 Cottage St, Brookline, MA 02445

    Luxury and style await you at 100 Cottage Street — a modern masterpiece situated on a wooded 1.05-acre lot. Built in 2021, this 6 bedroom, 7 bath stunner offers the ultimate in privacy, with a fenced-in perimeter and wrought iron gate at the end of the driveway. As you enter through the custom glass doors, you’ll be greeted by a stunning two-story foyer and a grand staircase with custom glass

    George Sarkis Douglas Elliman Real Estate - The Sarkis Team

    100 Cottage St, Brookline, MA 02445
  • /36

    $9,995,000

    • 7 Beds
    • 10 Baths
    • 7,240 Sq Ft

    80 Dudley St, Brookline, MA 02445

    Elegance and modernity define this sunlit Chestnut Hill residence on the Reservoir, offering spacious rooms, an open layout and luxurious finishes. Minutes from Boston and recently built by a local top builder for the current owners, every detail reflects meticulous craftsmanship, state-of-the-art systems and thoughtful design. A grand staircase separates entertaining areas from private spaces

    Maggie Gold Seelig MGS Group Real Estate LTD

    80 Dudley St, Brookline, MA 02445
  • /27

    $6,499,000

    • 7 Beds
    • 9 Baths
    • 6,000 Sq Ft

    75 Goddard Ave, Brookline, MA 02445

    Indulge in luxurious living with this exquisite home in Brookline estate section. Boasting 7 beds, 7 baths, and over 6000 sq ft on an acre, this residence is a sanctuary of sophistication. Experience unparalleled comfort with a geothermal system, 6-zone commercial setup fed by 3 x 600ft closed-loop wells. Radiant floor heat, multi-zone gas furnace, and dual mechanical closets ensure efficiency.

    Samantha Stumpo New Brook Realty Group, LLC

    75 Goddard Ave, Brookline, MA 02445
  • /39

    $1,500,000

    • 4 Beds
    • 3 Baths
    • 4,084 Sq Ft

    65 Lagrange St, Chestnut Hill, MA 02467

    Chestnut Hill- Opportunity knocks! Contractors and Builders take note. Renovate or start fresh and build your dream home. Sprawling single family brick ranch, custom built by a notable builder in 1953 for his family. Set on a beautiful flat 15,995 level lot with gracious entertainment size rooms and high ceilings. Large family room on main level with walls of glass overlooking beautiful private

    Michele Friedler Team Hammond Residential Real Estate

    65 Lagrange St, Chestnut Hill, MA 02467
  • /33

    $2,499,000

    • 4 Beds
    • 4.5 Baths
    • 2,715 Sq Ft

    72 Wallis Rd, Chestnut Hill, MA 02467

    Welcome to a meticulously rebuilt modern gem in Brookline! Completely reimagined from the studs, this open-concept home features 4 bedrooms, 4 full baths, and a convenient first-floor powder room. The main level flows effortlessly, with a spacious family/living room, dining area, and a chef's kitchen equipped with Thermador appliances, sleek handle-less cabinetry, quartz countertops, and an

    Svetlana Gorokhovsky Panorama Realty, Inc.

    72 Wallis Rd, Chestnut Hill, MA 02467
  • /42

    $3,049,500

    • 5 Beds
    • 3.5 Baths
    • 5,076 Sq Ft

    34 Lagrange St, Chestnut Hill, MA 02467

    This striking brick contemporary offers the perfect blend of space, light, and elegance. Spread across three levels, the home welcomes you with a dramatic atrium-style foyer. The open-concept living and family rooms flow beautifully for modern living and entertaining. The spacious layout includes 5+ bedrooms and 3 and half bathrooms, offering comfort and flexibility for family and guests. French

    Charles Roderick eXp Realty

    34 Lagrange St, Chestnut Hill, MA 02467
  • /18

    $12,995,000

    • 6 Beds
    • 6 Baths
    • 7,502 Sq Ft

    71 Sears Rd, Brookline, MA 02445

    We are delighted to present one of Brookline's most exceptional properties to hit the market in over a decade. Located in the prestigious estate area, this stunning 1929 Colonial Revival home offers 14 rooms and is set on two lush acres. The property features an inviting in-ground pool, sweeping lawns, specimen trees, perennial gardens, and a serene, man-made freshwater creek. With approximately

    Michael & Conor Chamberlain Coldwell Banker Realty - Brookline

    71 Sears Rd, Brookline, MA 02445
  • /2

    $8,000,000

    • Land
    • 1.87 Acres
    • $4,278,075 per Acre

    39 Clyde St, Chestnut Hill, MA 02467

    Set atop a gently elevated 1.86-acre lot, this exceptional property offers the perfect canvas to build a custom estate. The current European-style home is ready for demolition, making way for new construction in a private, hilltop setting. Surrounded by mature trees and located near top schools, shops, and cultural attractions, this rare offering combines location, scale, and potential in one of

    Melissa Dailey Coldwell Banker Realty - Wellesley

    39 Clyde St, Chestnut Hill, MA 02467
  • /42

    $2,595,000

    • 4 Beds
    • 2.5 Baths
    • 2,841 Sq Ft

    173 South St, Chestnut Hill, MA 02467

    Fantastic opportunity to purchase new construction in a superb location. This contemporary farmhouse boasts an open floor plan, featuring a formal living room with a fireplace, a dining area with a wine refrigerator, and a family room, all designed for entertaining. The gorgeous kitchen features custom white cabinetry, quartz countertops, an island, and Thermador stainless steel appliances. Off

    Kevin Keating Keating Brokerage

    173 South St, Chestnut Hill, MA 02467
  • /25

    $1,299,900 Open Sat 2PM - 3:30PM

    • 3 Beds
    • 2.5 Baths
    • 2,405 Sq Ft

    4 Benjamin Place, Chestnut Hill, MA 02467

    Open house Sat 2-3:30pm. Tucked away on a quiet Chestnut Hill cul-de-sac, this stunningly recently renovated townhouse blends luxury, light, and space in all the right ways. Step into soaring high ceilings, sun-drenched open living areas, and a chef’s dream kitchen with custom cabinets and premium stainless appliances. Relax by the fireplace or entertain on your private patio. With direct garage

    The Young Group Leopold & McMasters Realty

    4 Benjamin Place, Chestnut Hill, MA 02467
  • /42

    $18,000,000

    • 6 Beds
    • 8 Baths
    • 9,411 Sq Ft

    63 Goddard Ave, Brookline, MA 02445

    This spectacular residence, set on 4.5 acres in the prestigious Brookline Estate area, has been gut-renovated and is surrounded by private, scenic landscapes. The interior, distinguished by its grandeur and elegance, is adorned with intricate period details, beautiful woodwork, and bright spacious rooms. The grand 13 rooms include a double living room with picturesque views of the gorgeous,

    Debby Belt Hammond Residential Real Estate

    63 Goddard Ave, Brookline, MA 02445
  • /12

    $1,995,000

    • 4 Beds
    • 3.5 Baths
    • 3,437 Sq Ft

    303 Goddard Ave, Brookline, MA 02445

    Elegant large townhouse offers inviting floor plan with high ceilings, walls of windows and glass doors to deck overlooking private garden. Perfect for entertaining, the first floor has a gracious Living room, pretty dining room, large family room with vaulted ceiling, fireplace, and spacious open kitchen. The main level also include primary bedroom with walk-in closet and four piece bath with

    Susan and Jen Rothstein Team Hammond Residential Real Estate

    303 Goddard Ave, Brookline, MA 02445
  • /30

    $1,045,000

    • 3 Beds
    • 1 Bath
    • 1,337 Sq Ft

    159 Payson Rd, Chestnut Hill, MA 02467

    A rare opportunity to enjoy single-family living in a highly desirable Brookline neighborhood in the Baker district. This welcoming and classic 3 bed, 1 bath Garrison Colonial offers a bright and inviting layout. The 1st floor features hardwood floors, fireplaced living room, dining room adjoining the kitchen, and warm cozy den area that leads to a private screened-in porch perfect for al fresco

    Rita Lu Keller Williams Realty Boston-Metro | Back Bay

    159 Payson Rd, Chestnut Hill, MA 02467
  • /42

    $3,599,000

    • 5 Beds
    • 4.5 Baths
    • 5,068 Sq Ft

    71 Grove St, Chestnut Hill, MA 02467

    This contemporary masterpiece in Brookline boasts solid, soundproof construction in a tranquil setting among the trees. With an open floor plan that allows for maximum customization of the space — 71 Grove features enormous picture windows that offer abundant natural light, massive living and dining areas, and a state-of-the-art custom kitchen that is sure to impress. Take advantage of 5 total

    George Sarkis Douglas Elliman Real Estate - The Sarkis Team

    71 Grove St, Chestnut Hill, MA 02467
  • /31

    $2,495,000 Open Thu 5PM - 6PM

    • 4 Beds
    • 3.5 Baths
    • 3,444 Sq Ft

    50 Bellingham Rd, Chestnut Hill, MA 02467

    Impressive, custom built contemporary home on an expansive half acre+ wooded lot on tree lined street in Chestnut Hill. Designed by Harvard architect Mollie Moran includes sweeping 10 ft. cathedral ceilings & window walls overlooking lush park like multi level landscape. Elegant living room with marble wood burning fireplace accented with a wall of built-ins & a stunning entertainment sized

    Hickman - Coen Home Team William Raveis R. E. & Home Services

    50 Bellingham Rd, Chestnut Hill, MA 02467
  • /42

    $1,499,000

    • 4 Beds
    • 3.5 Baths
    • 2,660 Sq Ft

    646 Newton St Unit 2, Chestnut Hill, MA 02467

    Welcome to 646 Newton Street, a stunning residence that perfectly blends charm, elegance, and modern convenience. This beautifully designed and renovated head to toe 4-bedroom, 3.5-bathroom home offers a spacious layout with thoughtful details that make every space feel inviting.Step into a bright and airy living room, where high ceilings and large windows create an open and welcoming atmosphere.

    Eugene Doktorov Knight Realty

    646 Newton St Unit 2, Chestnut Hill, MA 02467
  • /20

    $2,770,000

    • 3 Beds
    • 3.5 Baths
    • 3,209 Sq Ft

    291 Goddard Ave, Brookline, MA 02445

    Beautifully renovated 3BD plus office, 3.5BA townhouse offers over 3,600 sqft of thoughtfully designed space. Expansive windows on 3 sides fill the home with natural light, enhancing its soaring ceilings, bespoke cabinetry, and elegant finishes. Bright entry leads to a spacious LR with 9.5-ft ceilings and sliding doors to deck and garden. Elegant DR features custom built-ins and sliding doors.

    Hilary Maddox Team Compass

    291 Goddard Ave, Brookline, MA 02445
  • /29

    $2,299,000

    • 4 Beds
    • 4.5 Baths
    • 3,193 Sq Ft

    809-811 Heath St Unit 811, Brookline, MA 02467

    Gorgeous new construction completed in October 2024, located in the heart of Chestnut Hill, less than a mile from Chestnut Hill Mall, Chestnut Hill Square, and The Street. Close to Skyline Park and Hammond Pond for trails and outdoor space. This 4 bed, 4.5 bath home offers over 3,000 sq ft of living space, tucked off the main road with easy access to Route 9. Features include a garage with two

    Yasmeen Moukaddem McCorry Real Estate, LLC

    809-811 Heath St Unit 811, Brookline, MA 02467
  • /37

    $24,500,000

    • 11 Beds
    • 11 Baths
    • 20,074 Sq Ft

    333 Lee St, Brookline, MA 02445

    This stately Georgian Revival residence, designed by the esteemed American architect and artist William Truman Aldrich, presents a once-in-a-lifetime opportunity to own one of the most prestigious and treasured estates in all of greater Boston. 333 Lee Street is perfectly situated on three acres of meticulously landscaped grounds. The interior boasts eleven bedrooms, eleven bathrooms, and ten

    George Sarkis Douglas Elliman Real Estate - The Sarkis Team

    333 Lee St, Brookline, MA 02445
  • /19

    $3,995,000

    • 7 Beds
    • 5 Baths
    • 6,307 Sq Ft

    469 Walnut St, Brookline, MA 02445

    Nestled beside the tranquil Brookline Reservoir, this charming home combines turn-of-the-century craftsmanship with modern comfort. Sunlight pours into spacious rooms, highlighting eight elegant fireplaces and timeless details throughout. Gracious family spaces invite effortless entertaining, from the formal dining room to the expansive living room with cozy warmth and a beautiful library with

    Michael & Conor Chamberlain Coldwell Banker Realty - Brookline

    469 Walnut St, Brookline, MA 02445
  • /28

    $16,000,000

    • 6 Beds
    • 8 Baths
    • 9,480 Sq Ft

    280 Warren St, Brookline, MA 02445

    Presenting a unique opportunity to own one of Brookline’s premier estate properties. Set on over 3 1/2 acres, this meticulously renovated residence has 19 rooms, including 6 beds, 6 full and 2 half baths, It has 6 fireplaces, and a fabulous kitchen with top appliances and a large eat-in area with French doors leading to the back patio. There are grand proportioned rooms with high ceilings and

    The Whitney Group Hammond Residential Real Estate

    280 Warren St, Brookline, MA 02445
  • /29

    $2,299,000

    • 4 Beds
    • 4.5 Baths
    • 3,193 Sq Ft

    811 Heath St, Chestnut Hill, MA 02467

    New construction townhouse-style condo completed in October 2024, offering 4 beds, 4.5 baths, and over 3,000 sq ft in the heart of Chestnut Hill. Open-concept main level with kitchen, living area, half bath, and walkout to a private deck and fenced garden. Four bedrooms each feature walk-in closets and en-suite baths. Includes a dedicated laundry room, bonus office, and tiled mudroom entry from

    Yasmeen Moukaddem McCorry Real Estate, LLC

    811 Heath St, Chestnut Hill, MA 02467
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