Brookline, MA Homes for Sale

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  /42

  $19,000,000

  • 7 Beds
  • 11 Baths
  • 13,343 Sq Ft

  1014 Boylston St, Chestnut Hill, MA 02467

  Introducing Paine Estate, a grand Georgian Revival architectural treasure located in the highly coveted Chestnut Hill neighborhood. This outstanding property has been extensively renovated, combining traditional style with modern amenities in a thoughtful floor plan ideal for family living and grand entertaining. Exceptional features include a grand entry hall, an elegant formal sunken living

  

  Deborah M Gordon

  Coldwell Banker Realty - Brookline

  (857) 575-4789

  1014 Boylston St, Chestnut Hill, MA 02467
• Explore Brookline

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  /38

  $5,195,000

  • 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
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  /42

  $7,995,000

  • 7 Beds
  • 11 Baths
  • 8,921 Sq Ft

  55 Leicester St, Brookline, MA 02445

  55 Leicester offers a rare opportunity in one of Brookline’s premier, private locations. Behind its grand facade and dramatic floating staircase, this expansive estate awaits its next chapter. While the home showcases soaring ceilings, walls of windows overlooking landscaped grounds, and an open, light-filled floor plan, it is ready for a visionary buyer to reimagine and restore its full

  George Sarkis Douglas Elliman Real Estate - The Sarkis Team

  55 Leicester St, Brookline, MA 02445
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  /38

  $6,050,000 Open Sun 11AM - 12:30PM

  • 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
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  /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
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  /22

  $5,985,000

  • 4 Beds
  • 4.5 Baths
  • 3,560 Sq Ft

  178 Ivy St, Brookline, MA 02446

  Tucked on a private road in Brookline’s coveted Cottage Farm neighborhood, this exceptional Colonial-style former carriage house underwent a 2 year renovation to the highest standards, completed in 2025. Soaring ceilings and oversized windows bathe the home in natural light and frame serene views of the surrounding gardens, yard and conservation land. The 1st floor presents a stunning open plan

  Maggie Gold Seelig MGS Group Real Estate LTD

  178 Ivy St, Brookline, MA 02446
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  /9

  $5,850,000

  • 6 Beds
  • 6.5 Baths
  • 8,326 Sq Ft

  180 Ivy St, Brookline, MA 02446

  An elegant estate offering an opportunity to restore, renovate and reimagine a classic residence in a premier location. Introducing The Loring-Atherton House, an estate showcasing iconic Georgian Revival architecture located in the heart of Brookline’s Cottage Farm Historic District, a neighborhood celebrated for its architectural beauty, timeless character, and historical significance. Held by

  Ricardo Rodriguez Coldwell Banker Realty - Boston

  180 Ivy St, Brookline, MA 02446
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  /38

  $6,595,000 Open Sat 1PM - 2:30PM

  • 5 Beds
  • 4.5 Baths
  • 6,556 Sq Ft

  33 Leicester St, Brookline, MA 02445

  Introducing a rare, exquisite residence in Brookline's coveted Fisher Hill neighborhood. This five-bedroom-plus-study estate masterfully blends a historic street-facing exterior with sleek design and a stunning modern interior. Thoroughly and meticulously renovated in 2016, and with more updates since the last sale in 2021, the property offers elegant, contemporary living spaces and

  Lili Banani Coldwell Banker Realty - Boston

  33 Leicester St, Brookline, MA 02445
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  /42

  $5,950,000

  • 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
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  /5

  $5,950,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 4,825 Sq Ft

  9 Willard Rd, Brookline, MA 02445

  Unique opportunity to have your dream home built in the heart of Fisher Hill! 11,338 sf level lot with foundation and plans for a 4 bedroom, 3.5 bath classic brick colonial home with 4,825 square feet of space (on 3 levels) and a 2 car detached garage with shed. Gourmet kitchen opens to the den, dining and living room. First floor covered porch and terrace, perfect for al fresco dining.

  Celine Sellam Coldwell Banker Realty - Brookline

  9 Willard Rd, Brookline, MA 02445
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  $3,399,000 Open Sun 11:30AM - 1PM

  • 7 Beds
  • 5 Baths
  • 4,171 Sq Ft

  255 Tappan St, Brookline, MA 02445

  Available for the first time in 72 years, 255 Tappan Street is a beautifully maintained brick two-family home with additional living space. Perfectly positioned near Washington Square and Brookline’s top restaurants and bars, the home sits just off Beacon Street near Brookline High School and the Green Line, offering unbeatable convenience. Star Market is located right at the end of the street.

  Dan Rosenthal Rise Signature Homes

  255 Tappan St, Brookline, MA 02445
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  /25

  $3,500,000

  • Land
  • 0.92 Acre
  • $3,804,348 per Acre

  79 Goddard Ave, Brookline, MA 02445

  Vacant, build-able, legally conforming lot in the heart of Brookline, directly next to The Park School on Goddard Avenue, perfect for a single family home. Call list agent for directions on how to view the property. Appraisal and site plan in hand.

  Melissa Deland Deland Real Estate, LLC

  79 Goddard Ave, Brookline, MA 02445
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  /20

  $5,000,000

  • 5 Beds
  • 4.5 Baths
  • 6,419 Sq Ft

  540 Chestnut Hill Ave, Brookline, MA 02445

  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

  The Duffy Group Compass

  540 Chestnut Hill Ave, Brookline, MA 02445
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  /33

  $2,999,999

  • 3 Beds
  • 3.5 Baths
  • 2,552 Sq Ft

  71 Greenough St Unit 71-1, Brookline, MA 02445

  This stunning new construction condo has it all - 3 beds, 3.5 baths, elevator, 2-car garage, private fenced yard w/deck and patio! Inspired design and exceptional attention to detail combine to create a sophisticated, comfortable and versatile living environment. Elegant living room features gas fireplace, built-ins, and French doors that open to deck/yard, allowing for easy indoor-outdoor

  Kathy Halley Hammond Residential Real Estate

  71 Greenough St Unit 71-1, Brookline, MA 02445
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  /22

  $3,749,000

  • 5 Beds
  • 4.5 Baths
  • 4,711 Sq Ft

  15 Glenland Rd, Chestnut Hill, MA 02467

  Experience luxury in this newly completed custom home by a renowned local builder. Ideally situated in the highly desirable Brookline/Chestnut Hill neighborhood, this residence offers the perfect blend of upscale living and everyday comfort. The sun splashed main level features an open & airy layout with soaring ceilings & oversized windows that fill the space with natural light. An elegant

  Rjp Sells Coldwell Banker Realty - Brookline

  15 Glenland Rd, Chestnut Hill, MA 02467
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  $4,198,000 Open Sun 12:30PM - 2PM

  • 6 Beds
  • 5.5 Baths
  • 5,789 Sq Ft

  66 Summit Ave, Brookline, MA 02446

  Exquisite Brookline Victorian. Designed for today’s lifestyle, this stunning home blends timeless character w/ modern comfort. Perfectly situated in the heart of Coolidge Corner, offering grand-scale rooms, abundant natural light, and versatile spaces ideal for both everyday living & entertaining. A welcoming front porch and gracious foyer set the tone. The first floor features a spacious living

  Kami Gray Coldwell Banker Realty - Brookline

  66 Summit Ave, Brookline, MA 02446
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  $2,995,000 Open Sat 10AM - 11AM

  • 4 Beds
  • 3.5 Baths
  • 3,963 Sq Ft

  236 Walnut St, Brookline, MA 02445

  Sophisticated Pill Hill residence in a Romanesque puddingstone row house designed by Henry Ives Cobb c. 1887, blends beautiful period detail with discerning finish and design offering recessed windows with built-in shutters, five original tile fireplaces, and impeccable renovations. First floor features an elegant foyer, living room with custom bookshelves and bay window, dining room with French

  Susan and Jen Rothstein Team Hammond Residential Real Estate

  236 Walnut St, Brookline, MA 02445
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  /42

  $5,797,999

  • 10 Beds
  • 10 Baths
  • 7,898 Sq Ft

  84 Winthrop Rd, Brookline, MA 02445

  Welcome to 84 Winthrop Rd—an extraordinary two-family residence in the heart of Brookline, offering nearly 8,000 sq. ft. of luxurious living. With 10 bedrooms and 8 and half bathrooms across two expansive homes, this property is designed for both elegance and functionality. Inside, discover chef-inspired kitchens appointed with premium Miele and Viking appliances, custom cabinetry, and

  George Sariego Boston One Realty Group Inc

  84 Winthrop Rd, Brookline, MA 02445
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  /42

  $4,350,000 Open Sun 2PM - 3:30PM

  • 5 Beds
  • 4.5 Baths
  • 4,072 Sq Ft

  36 Allerton St, Brookline, MA 02445

  Exquisite 2005 Arts & Crafts style home in Historic Pill Hill by noted architect Tom Catalano, unique in every regard, offers luxurious custom elements at every turn. Beautiful gardens and hardscaping set the scene from the street. An over-the-top kitchen w/large center island and spacious FP’d family room anchor the home and offer glass slider access a lovely rear bluestone patio, heated lap

  The Gillach Group William Raveis R. E. & Home Services

  36 Allerton St, Brookline, MA 02445
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  /6

  $3,650,000

  • 3 Beds
  • 3.5 Baths
  • 2,750 Sq Ft

  63 Green St Unit 3, Brookline, MA 02446

  Exceptional Opportunity in Coolidge Corner. Experience luxury living in this newly constructed floor-through penthouse, ideally located in the heart of Coolidge Corner. Sunlight streams through expansive windows, illuminating a stunning residence with a thoughtfully designed floor plan, premium finishes, designer details, soaring ceilings, and a state-of-the-art kitchen. This property features

  Mona and Shari Wiener Hammond Residential Real Estate

  63 Green St Unit 3, Brookline, MA 02446
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  /16

  $12,500,000

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

  71 Sears Rd, Brookline, MA 02445

  This is 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 7,000 square feet of

  Michael & Conor Chamberlain Coldwell Banker Realty - Brookline

  71 Sears Rd, Brookline, MA 02445
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  /42

  $4,599,600 Open Sat 11AM - 1PM

  • 6 Beds
  • 4.5 Baths
  • 5,397 Sq Ft

  85 Naples Rd, Brookline, MA 02446

  Experience the pinnacle of luxury living in this fully gut-renovated single-family home on prestigious Naples Road in the heart of Coolidge Corner, Brookline. Blending timeless architectural charm with modern sophistication, this residence showcases exquisite details including copper gutters, elegant turrets, and designer finishes throughout. A private elevator provides effortless access across

  Aurel Garban Gibson Sotheby's International Realty

  85 Naples Rd, Brookline, MA 02446
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  /40

  $4,995,000

  • 7 Beds
  • 5.5 Baths
  • 6,193 Sq Ft

  371 Walnut St, Brookline, MA 02445

  This 7BD, 5.5BA c1880 Greek Revival reflects historic character while embracing a meticulous, modern renovation. Set on a landscaped .96AC lot, this stately 6,100+SF residence has been thoughtfully expanded & updated to enhance today’s modern living. Soaring ceilings, bespoke millwork & 5 FP highlight the architecture, while clean, timeless finishes offer understated elegance. Gracious entry

  Hilary Maddox Team Compass

  371 Walnut St, Brookline, MA 02445
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  /17

  $12,507,200

  • 29 Baths
  • 9,915 Sq Ft

  89 Marion St, Brookline, MA 02446

  We are pleased to present this opportunity for sale which consists of 29 fully furnished short-term rental units located in Coolidge Corner, one of Brookline’s oldest commercial hubs. Located just off of Beacon Street, the building offers convenient access to restaurants, one-of-a-kind boutiques, and the MBTA Green Line. Guests of the property enjoy modern furnishings and technology while staying

  Nicholas Herz Boston Realty Advisors

  89 Marion St, Brookline, MA 02446
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  /19

  $4,495,000 Open Sun 12PM - 1PM

  • 5 Beds
  • 4.5 Baths
  • 4,001 Sq Ft

  34 Hyslop Rd, Brookline, MA 02445

  This very special residence is beautifully sited on one of Fisher Hill’s loveliest streets. Featuring 11 rooms, 5 bedrooms, and 4.5 bathrooms, it was completely renovated by the current owner with impeccable craftsmanship and design. Soaring ceilings, skylights, and abundant windows fill the space with natural light and create a contemporary flair. Glass doors from the living area open to a lush,

  Mona and Shari Wiener Hammond Residential Real Estate

  34 Hyslop Rd, Brookline, MA 02445
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  /38

  $9,495,000

  • 5 Beds
  • 5.5 Baths
  • 7,096 Sq Ft

  138 Woodland Rd, Chestnut Hill, MA 02467

  Built in 2022 by one of Boston’s premier luxury builders, this masterfully crafted residence redefines modern elegance and sophistication. From the moment you enter the dramatic two-story foyer, the home sets the stage for grand entertaining and refined living. The expansive first floor showcases palatial rooms, a formal sitting room, a library, and an expansive guest suite. At the heart of the

  George Sarkis Douglas Elliman Real Estate - The Sarkis Team

  138 Woodland Rd, Chestnut Hill, MA 02467
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  /42

  $4,599,600 Open Sat 11AM - 1PM

  • 6 Beds
  • 4.5 Baths
  • 5,397 Sq Ft

  85 Naples Rd Unit 1, Brookline, MA 02446

  Experience the pinnacle of luxury living in this fully gut-renovated single-family home on prestigious Naples Road in the heart of Coolidge Corner, Brookline. Blending timeless architectural charm with modern sophistication, this residence showcases exquisite details including copper gutters, elegant turrets, and designer finishes throughout. A private elevator provides effortless access across

  Aurel Garban Gibson Sotheby's International Realty

  85 Naples Rd Unit 1, Brookline, MA 02446
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  /20

  $3,495,000

  • 4 Beds
  • 3.5 Baths
  • 2,605 Sq Ft

  57 University Rd Unit 3, Brookline, MA 02445

  Direct elevator access into this modern penthouse duplexed home with private roof terrace! Ultra-modern luxury and chic custom design, this 4 bedroom/3.5 bath tree-top penthouse has a stunning open concept floor plan with soaring ceilings, gleaming wide-plank oak hardwood floors, and oversized windows creating walls of glass with an abundance of natural light. Take the elevator from the garage

  Joseph DeAngelo Coldwell Banker Realty - Boston

  57 University Rd Unit 3, Brookline, MA 02445
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  /34

  $2,945,000

  • 8 Beds
  • 6 Baths
  • 5,803 Sq Ft

  9 Downing Rd, Brookline, MA 02445

  Spectacular 5800 SqFt Colonial Revival c. 1907 with unbelievable original detail throughout, built for Leonard Rhodes, a Brookline greengrocer. Grand Foyer with Princess staircase, powder room; front to back formal living room with beamed ceiling, bow windows, fireplace w/carved maple mantel and Grueby Arts & Crafts hand-painted tile frieze. Wood panelled sunroom w stone fpl & stained glass;

  Mary M. Wallace Gibson Sotheby's International Realty

  9 Downing Rd, Brookline, MA 02445
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  /42

  $3,198,000

  • 5 Beds
  • 3.5 Baths
  • 3,648 Sq Ft

  140 Dudley St, Brookline, MA 02445

  Beautifully sited across from the Brookline Reservoir, this timeless 5-bedroom brick Colonial offers classic architecture, serene water views, and multiple outdoor spaces designed for effortless living and entertaining. The main level features a front-to-back living room with fireplace, a formal dining room, and a bright white eat-in kitchen that opens to a private covered deck. A spacious den

  Allison Blank Compass

  140 Dudley St, Brookline, MA 02445
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  /21

  $2,995,000

  • 2 Beds
  • 2.5 Baths
  • 2,292 Sq Ft

  120 Seaver St Unit E201, Brookline, MA 02445

  Rarely available! Two bedroom plus study, two full and one half bathroom condo located on the second floor of the Historic Longyear Mansion at Longyear at Fisher Hill, Brookline’s premiere private eight acre gated community. Unit features an open kitchen with professional appliances, a wet bar and breakfast nook. The nearly 2,300 sq ft sun drenched open floor plan has north, south and western

  Hope Krakoff Coldwell Banker Realty - Boston

  120 Seaver St Unit E201, Brookline, MA 02445
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  /28

  $3,995,000

  • 9 Beds
  • 7 Baths
  • 6,292 Sq Ft

  476 Heath St, Chestnut Hill, MA 02467

  A rare opportunity to own a distinguished Brookline estate that seamlessly blends historic grandeur with modern luxury. Originally built in 1899 and thoughtfully renovated, this stunning residence offers 6,292 sq ft of exquisitely finished living space on an expansive 18,438 Sq Ft lot. Spread across 3 finished floors, the home features 8 bedrooms, 4 full and 3 half bathrooms, and 2 beautifully

  Samantha Stumpo New Brook Realty Group, LLC

  476 Heath St, Chestnut Hill, MA 02467
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  /17

  $16,000,000

  • 54 Beds
  • 21 Baths
  • 34,849 Sq Ft

  108-116 Winthrop Rd, Brookline, MA 02445

  We are pleased to present the opportunity to acquire 108-116 Winthrop Road, a boutique 18-unit, 100% market rate apartment building located in the heart of Brookline, Massachusetts. The property is situated in one of the most sought after streets in the coveted Washington Square neighborhood. The building features charming common area spaces, attractively landscaped grounds, 14 on-site parking

  Marika and Adam Real Estate Group Hammond Residential Real Estate

  108-116 Winthrop Rd, Brookline, MA 02445
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  /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
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  /42

  $5,800,000

  • 8 Beds
  • 8 Baths
  • 6,000 Sq Ft

  116 Thorndike St, Brookline, MA 02446

  Welcome to this rare opportunity to own a meticulously maintained luxury multi-family estate in one of Brookline’s most prestigious neighborhoods. Nestled on a tree-lined street just minutes from Coolidge Corner, Longwood Medical Area, and Downtown Boston, this stately property offers timeless elegance, modern upgrades, and unmatched versatility for owner-occupants or savvy investors. Featuring 2

  Tatiana Bonderman KenDrix Realty, LLC

  116 Thorndike St, Brookline, MA 02446
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  /28

  $4,499,000

  • 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 Gibson Sotheby's International Realty

  69 Princeton Rd, Chestnut Hill, MA 02467
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  /38

  $3,699,000

  • 4 Beds
  • 4.5 Baths
  • 3,700 Sq Ft

  216 Aspinwall Ave, Brookline, MA 02446

  Complete renovation of a distinctive Carriage House in a prime Brookline location that offers the perfect blend of urban and suburban living. This 4-bedroom, 4.5-bath home spans three floors and features a first-floor guest suite, an open layout ideal for entertaining, designer kitchen with a stunning quartz island & Thermador appliances. The elegant, fireplaced family room opens to a beautifully

  Leslie Zelada Grover Group Realty LLC

  216 Aspinwall Ave, Brookline, MA 02446
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  /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
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  /35

  $3,679,000

  • 6 Beds
  • 5.5 Baths
  • 5,000 Sq Ft

  33 Winthrop Rd Unit 1, Brookline, MA 02445

  Modern luxury in the heart of Brookline! Built in 2018 and meticulously maintained, this stunning large townhouse offers the perfect blend of style, comfort, and location—just a short walk to Washington Sq, Coolidge Corner & The Village. Flooded with natural light, the flexible open floor plan features a chef’s kitchen with an 8-burner Viking stove and island seating, ideal for entertaining. The

  The Ridick Revis Group Compass

  33 Winthrop Rd Unit 1, Brookline, MA 02445
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  /22

  $3,699,000

  • 5 Beds
  • 3.5 Baths
  • 6,196 Sq Ft

  460 Heath St, Chestnut Hill, MA 02467

  Ideally situated on a private cul-de-sac in Chestnut Hill, this stunning architectural gem offers timeless elegance & modern luxury. Just minutes to the T, restaurants, coffee shops, & shopping, it boasts unobstructed park views from a Bluestone patio with a luxury outdoor kitchen and 8' gas fireplace perfect for entertaining. Inside, enjoy a sauna, home gym, wine cellar, billiards room, & a

  Samantha Stumpo New Brook Realty Group, LLC

  460 Heath St, Chestnut Hill, MA 02467

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