Brookline, MA Real Estate | Brookline, MA Single Family Homes for Sale

Entering Brookline! Welcome home! Lovely entryway with closet welcomes you into fire placed, sunlit living room with mellow hardwood floors that opens to ample dining room perfect for holiday entertaining. Three season sunroom and fully applianced kitchen round out the first floor. Direct entry garage is a bonus! Second level offers 2 generous bedrooms and a smaller nursery or office and full bath. Basement is partially finished for bonus space! Situated on a lovely fenced lot. Bring your ideas and pack your bags. There is so much potential with this property. Excellent location, Baker school district. Best value in Chestnut Hill! Don't miss! Offers, if any, due Tuesday at noon!

77 Payson Rd, Brookline

Listing courtesy of Listing Agent: Patsy Brennan from Listing Office: Vogt Realty Group, LLC.

$2,799,999

4 Beds ⋅ 4 Baths ⋅ 73592951 MLS

Tucked away on a quiet Chestnut Hill street, this 1927 classic Tudor is filled with warmth, character, and thoughtful modern updates. With 4 bedrooms, 3.5 bathrooms, central air conditioning, a dedicated playroom, and an attached two-car garage, the home offers plenty of space and everyday practicality without sacrificing personality. A welcoming foyer leads to the formal open living and dining room, while the updated chef’s kitchen connects seamlessly to the family room, creating an easy layout for modern living. A sunny breakfast room provides the perfect spot for casual meals, and just beyond the family room, a deck overlooks the beautifully landscaped backyard, extending the living space outdoors. Upstairs, the primary bedroom is joined by two additional bedrooms, two full bathrooms, and generous storage. The lower level includes a fourth bedroom, laundry room, additional storage, another full bathroom, and direct access to the two-car garage. Fabulous Chestnut Hill location close to the shops and restaurants at The Street at Chestnut Hill, convenient access to Route 9 and just half a mile from the Green Line "T".

79 Randolph Road, Brookline

Listing courtesy of Listing Agent: Jeffrey Hamilton from Listing Office: Columbus and Over Group, LLC.

$5,250,000

6 Beds ⋅ 5 Baths ⋅ 73592699 MLS

Rarely does a Gilded Age landmark arrive so thoroughly reborn. Designed in 1905 by architect Alfred L. Darrow, 46 Powell Street commands a coveted corner lot in the Cottage Farm Historic District, guarded by carved stone griffins and a scrolled wrought-iron gate. Stone, stucco, half-timbered gables, carved-bracket eaves and a terra cotta roof frame approx. 7,028 SF of Arts & Crafts and Tudor Revival grandeur, delivered with every modern comfort. A 2022 renovation rewired the entire home (400-amp service, integrated alarm, smoke and CO detection, ADT security with outdoor cameras), added central air, a new gas boiler, radiant-heated floors, and a sensor-driven snow-melt driveway and rear walkway, all without sacrificing a single carved detail. Some original doors were repurposed as pocket doors. Step into a two-story marble and mosaic foyer beneath a barrel-vaulted, rosette-coffered ceiling. A hand-carved bridal staircase rises to a soaring atrium lit by leaded-stained glass restored by Jim Anderson of “This Old House”. Five fireplaces, a library with gilt-carved bookcases and medieval English plaster ceiling, and a Jacobean dining room with butler’s pantry set the formal stage. The chef’s kitchen, featured in New England Home magazine, pairs mahogany, burlwood, brass and marble with Visual Comfort lighting, a Sub-Zero refrigerator, Thermador six-burner range, coffee bar with refrigerated drawers, and an antique bell box. It opens to a breakfast nook, a rear deck and a sunlit solarium with domed plaster ceiling. Upstairs, the primary suite offers a fireplace with Roman-tile surround, two leaded-glass bay windows, dressing area, walk-in closet and dual-sink bath with radiant-heated floors. The second suite adds a marble fireplace, walk-in closet and Paris-Metro tiled bath beneath a Tiffany-style transom. Six bedrooms and 4.5 renovated baths. The third floor delivers a kitchenette, walk-in laundry, cedar closet with sauna potential and a cathedral-loft billiard room with king-post beams and Franklin stove, ideal for media or games. The 2,534 SF lower level offers open space and a wine cellar. Private parking for three in the heated driveway plus a detached 1919 Spanish Colonial two-car garage. Specimen plantings and old-growth trees surround the grounds, and commercial-grade internet serves modern households. Just 100 yards to Beacon Street and the C Line, under one mile to Kenmore Square and 2.5 miles to the Public Garden. A fully renewed architectural icon.

46 Powell Street, Brookline

Listing courtesy of Listing Agent: Ama Agumeh from Listing Office: Barrett Sotheby's International Realty.

$8,400,000

7 Beds ⋅ 8 Baths ⋅ 73592560 MLS

Set on 1.21 private acres in Brookline’s coveted Sargent Estate neighborhood, 54 Sargent Road is a c.1925 Colonial reimagined through a thoughtful, design-driven renovation. Tall ceilings, preserved millwork, detailed moldings, and four fireplaces meet bespoke finishes and a warm palette of materials. Across 8,540 square feet, seven bedrooms, six full and two half baths accommodate everyday living and gracious entertaining. An elegant foyer connects the first-floor living spaces. The living room features a wood-burning fireplace with a custom Chesneys mantel, built-ins, window seats, and French doors offering views through the Conservatory to the gardens. Opposite, the dining room pairs a fireplace and built-in cabinetry with de Gournay wallpaper. A fully appointed bar leads to the expanded kitchen where custom cabinetry, two islands, and a curved breakfast room overlooking the grounds, and opens to a window-lined family room. A private office and second bar sit beyond. The house opens to one of its most striking spaces: the Conservatory. A defining addition in the sellers’ renovation, it forms the architectural link between the main house and the formerly detached carriage house and garage. The carriage house includes a three-car garage and a private guest suite above, with a bedroom, full bath, kitchenette, and living room opening through French doors to a patio with a hot tub. In the main house, a winding staircase framed by a soaring window leads to a book-lined landing and sun deck. The primary suite offers a fireplace, bespoke built-ins, two walk-in closets, and a spa-like bath. Two en-suite bedrooms, two bedrooms sharing a Jack-and-Jill bath, and laundry complete the second floor. The third floor adds a great room, bedroom, full bath, and storage. Below, a gym, recreation room, theater, wine cellar, half bath, and second laundry provide space for fitness and leisure. Outside, a bluestone patio off the kitchen invites al fresco dining. A garden fountain, intricate iron gate, and planted pathways lead to an expansive, private level lawn framed by mature trees. A fire pit offers a gathering place for evenings that linger well past dinner. Known for its quiet streets, pond, and conservation land, Sargent Estates surprising sense of nature so close to the city. Near Lincoln School, Brookline High, and area private schools,the property is blocks from the Green D Line, with convenient access to Longwood Medical Area, downtown Boston, Cambridge, and Logan.

54 Sargent Road, Brookline

Listing courtesy of Listing Agent: Hilary Maddox Team from Listing Office: Compass.

$5,398,000

5 Beds ⋅ 5 Baths ⋅ 73592351 MLS

Gracious and timeless historic single family attached home in Brookline's prestigious Fisher Hill Estates. This 5 bedroom/4.5 bath home offers more than 7,000 sqft of elegant living space with spectacular views of the Brookline Reservoir! This majestic home features period architectural details, a grand staircase, high ceilings, original built-ins and gleaming hardwood floors. Sundrenched by floor to ceiling windows, the main level offers a gracious living room/dining room with fireplace, a stunning mahogany library with fireplace, a beautiful family room, breakfast area and a chef's kitchen with direct access to a lovely garden area. The second floor primary suite features a spa like bath, walk-in closet, fireplace and a picturesque private deck with outstanding views. Completing this level is an additional en suite bedroom. The third floor offers two additional bedrooms and a full bath. The finished lower level features a direct entry guest suite with a living area, full bath and kitchen - perfect for an au pair. Completing this home is a two car detached garage and multiple outdoor private garden areas. Community amenities include pool and tennis court. Close to shopping, restaurants, schools, Downtown Boston and so much more! This home is definitely a must see!!

15 Catlin Road, Brookline

Listing courtesy of Listing Agent: The Jeff Groper Group from Listing Office: Coldwell Banker Realty - Newton.

$34,000,000

7 Beds ⋅ 16 Baths ⋅ 73590483 MLS

There are exceptional homes, and then there are properties conceived on an entirely different scale. 55 Singletree is the latter. Perched atop a secluded hill on more than two private acres in Brookline, adjacent to the reservoir, this extraordinary estate offers a rare sense of privacy and tranquility just minutes from Boston. Its elevated position and naturally sheltered setting create remarkable seclusion, with no neighboring homes overlooking the pool or private outdoor spaces. Years of vision, craftsmanship, and investment have been brought to life through an extensive two-phase construction project by Thoughtforms, one of New England’s most respected custom home builders. The result is not simply a residence, but a world unto itself—an estate with the scale and experience of a private resort. The property's commanding elevation captures views toward the Boston skyline, culminating at a rooftop terrace overlooking the city. Across the grounds, architecture and landscape have been conceived as one experience. Water features introduce movement and serenity, expansive outdoor spaces invite both gathering and escape, and a private tennis and sports court creates a level of recreation rarely found so close to the city. Inside, monumental scale meets intimate refinement, with exceptional materials, custom craftsmanship, and thoughtfully designed spaces equally suited for grand entertaining and everyday family life. An estate of this scale, caliber, and extraordinary privacy would be exceptionally difficult to replicate today. 55 Singletree represents a singular opportunity: a secluded residential sanctuary offering remarkable sophistication, recreation, and proximity to Boston.

55 Singletree Rd, Brookline

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

$995,000

3 Beds ⋅ 2 Baths ⋅ 73590431 MLS

Charming Colonial in a Coveted Brookline Location! Situated in an excellent neighborhood just a stone’s throw from Allandale Farm, Larz Anderson Park and Brookline's top-rated schools, this 3-bedroom, 1.5-bath Garrison Colonial presents a wonderful opportunity to create your dream home. The property features hardwood floors throughout, garage parking with direct access to the home and a generous lot of over 7,500 square feet. In need of updating, this home offers tremendous potential for renovation, personalization and long-term value in a highly desirable location. A rare opportunity to bring your vision to life in one of Brookline’s sought-after neighborhoods, close to parks, local amenities, hospitals and excellent educational opportunities. Offers, if any, to be reviewed on Monday, 10/19 by 2pm.

30 Hackensack Road, Brookline

Listing courtesy of Listing Agent: DelRose McShane Team from Listing Office: Coldwell Banker Realty - Belmont.

$4,250,000

5 Beds ⋅ 4 Baths ⋅ 73590255 MLS

Set high atop Aspinwall Hill in close proximity to Washington Square and Brookline Village, this incredible Shingle-style carriage house offers a remarkable confluence of breathtaking historical character and effortless contemporary cool. Designed by prominent Boston architects Hartwell and Richardson in 1888 and spanning over 6300 sf of interior living space, this property preserves striking original architectural features, from original double doors used for horse drawn carriages to a turreted top level living area featuring soaring cathedral ceilings, restored beams, skylights, and sweeping vistas of the lushly landscaped 0.58 acre lot. Modern touches also abound, from the stone-capped kitchen island in the upper-level entertaining space to the two-story fireplace in the voluminous open-plan downstairs living area. An entertainer’s paradise, this property offers two equally stunning living, dining and kitchen spaces, plus a wonderful newly refinished auxiliary lounge on the lower level. In addition to five generous bedrooms and three and a half full baths, the house also offers a brilliant built-in office or library, a second office / workspace in a repurposed carriage stall, and a versatile workshop or art studio. The one-of-a-kind “jockey walk” art gallery off the main foyer offers an inspiring spot to showcase an art collection. The house offers exceptional indoor-outdoor connections including a luminous family room or sun room off the garden, two generous decks, multiple balconies, a stone patio, and an expansive backyard with mature plantings. A graceful circular driveway and two garage bays offer plenty of parking for a crowd. Numerous recent updates, including five-zone 2023 HVAC, five new skylights, many new light fixtures; and new recessed lights, sheet rock and new or newly refinished wood floors in all the bedrooms. Exceptionally well located on a private way yet easily accessible to premier shopping, dining, multiple Green Line stops, downtown Boston, the Longwood Medical area, and renowned public and private schools. This thrilling property is like nothing you’ve ever seen---a serene oasis nestled in one of Brookline's most desirable locations with the best of city living at your doorstep. An incredible opportunity.

120 Rawson Rd, Brookline

Listing courtesy of Listing Agent: Elisabeth Preis from Listing Office: Compass.

$2,875,000

5 Beds ⋅ 3 Baths ⋅ 73590203 MLS

This thoughtfully renovated five-bedroom single family Colonial Revival on beautiful, tree-lined Fuller Street in the heart of Coolidge Corner has it all, indoors and out. A welcoming covered porch leads to a gracious foyer and spacious living room and dining room, with bay windows, original built-ins and a fireplace. A cook's kitchen features wide-plank hardwood floors, custom cabinetry, granite countertops and gas cooking. The inviting family room addition, with its cathedral ceiling, oversized windows, built-ins, and sliding glass doors topped by transom windows, overlooks a bluestone patio and generously sized private backyard and gardens, bringing the outdoors into the home. A half bath completes the first floor. The second floor offers three generous bedrooms, including an oversized primary suite with a walk-in closet and full bath, together with a spacious family bathroom. Two additional bedrooms occupy the third floor, one with a cathedral ceiling, along with ample storage and plumbing in place for another full bathroom. The lower level provides bonus space, including a recreation room, laundry, and access to the yard. The home includes two off-street parking spaces. Recent improvements include a new roof in 2020, a new gas heating system in 2021, exterior painting in 2022, and updated plumbing and electrical systems. The home also features central air conditioning. A complete list of updates is available with the listing. With beautiful parks, easy access to the Green Line's C and B branches, cafés, restaurants, markets, and the Coolidge Corner Theatre, 116 Fuller Street offers a distinctive opportunity to enjoy single-family living with the best of Brookline just beyond your doorstep.

116 Fuller St., Brookline

Listing courtesy of Listing Agent: Irene Kerzner from Listing Office: Hammond Residential Real Estate.

$2,350,000

6 Beds ⋅ 4 Baths ⋅ 73587355 MLS

Offered for the first time in 61 years, this is a rare opportunity to restore and reimagine a distinguished Colonial Revival residence in Brookline's coveted Fisher Hill neighborhood. Built in 1897, this remarkable home is rich in character, timeless architectural detail, and period charm, presenting an exceptional opportunity to create your dream home. Gracious, generously proportioned main rooms showcase the home's historic elegance, while three full levels of living space offer unlimited potential for customization and expansion. A striking oversized stained-glass window illuminates the main staircase, serving as a stunning focal point and a reminder of the home's enduring craftsmanship. Featuring 6-7 bedrooms, high ceilings, and flexible living areas, the property offers endless possibilities for today's lifestyle needs. The lower level includes a separate entrance, making it ideal for a home office, professional space, guest suite, or future finished living area. Ideally located just minutes from Runkle School, Brookline High School, parks, the Longwood Medical Area, and two Green Line T stations, this exceptional property combines a premier location with extraordinary potential.

309 Buckminster Rd, Brookline

Listing courtesy of Listing Agent: Jayne Friedberg from Listing Office: Coldwell Banker Realty - Brookline.

$3,999,000

8 Beds ⋅ 4 Baths ⋅ 73586478 MLS

A rare Brookline offering in the heart of Coolidge Corner, this distinguished renovated two-family residence delivers exceptional scale, elegance, and outdoor space seldom found in the area. Spanning an impressive 4,166 sq. ft. across 14 rooms, the home is set on an extraordinary 0.29-acre lot, presenting remarkable potential for future expansion, development, or bespoke customization. A true highlight of the estate is its expansive, level private backyard, a serene setting ideal for sophisticated outdoor entertaining, curated gardens, or recreational enjoyment. Both oversized units showcase sun-filled, flexible floor plans with 4 bedrooms and 2 full bathrooms each. Interiors are defined by gleaming hardwood floors, refined crown molding, a dedicated office/den, and an open kitchen concept that enhances flow and modern livability. The large, updated eat-in kitchens feature granite countertops, solid wood cabinetry, and stainless steel appliances. Private sunrooms and generous front and rear balcony/porches enhance the home’s indoor-outdoor flow and overlook the sweeping grounds. Additional amenities include in-unit laundry on both floors, a full unfinished walk-out basement offering substantial storage or future expansion potential, and a detached 2-car garage. The driveway accommodates up to 8 additional vehicles, with further capacity possible. Perfectly positioned just steps from the MBTA Green Line, top-rated schools including the Florida Ruffin Ridley School (PreK–8) and Brookline High School, and the vibrant Coolidge Corner district. Residents enjoy effortless access to a variety of shopping, acclaimed dining, parks, and premier medical institutions. For those seeking a refined multi-family or a single family residence, a generational estate, or a premier investment with exceptional outdoor space, this property stands in a class of its own.

91 Verndale St, Brookline

Listing courtesy of Listing Agent: Daniel S. Lee from Listing Office: Boston Plex.

$2,395,000

4 Beds ⋅ 4 Baths ⋅ 73584176 MLS

BROOKLINE’S HIGHLY RANKED A+ PUBLIC SCHOOLS.-- EXCEPTIONAL SINGLE-FAMILY LIVING. Completely rebuilt from the studs up, 641 Chestnut Hill Avenue combines classic character with luxury finishes and modern comfort. Four bedrooms, 3½ baths and approximately 2,800 square feet span four finished levels, including the finished lower level. A beautifully appointed kitchen and inviting living spaces create a welcoming setting for everyday living and entertaining. Thoughtfully designed luxury bathrooms feature upscale finishes, while the primary suite offers a private retreat alongside three additional bedrooms. Flexible finished spaces accommodate work, guests and recreation. Modern heat-pump heating and cooling, insulated windows, off-street parking spaces and private outdoor space enhance everyday convenience. Enjoy proximity to Brookline Reservoir, local amenities and Boston—a distinctive opportunity to own a completely rebuilt home in an established Brookline neighborhood .

641 Chestnut Hill Avenue, Brookline

Listing courtesy of Listing Agent: Paulette Rioux from Listing Office: Rioux Real Estate.

$3,500,000

6 Beds ⋅ 7 Baths ⋅ 73584015 MLS

A rare, generational opportunity to own an exceptional turn-of-the-century shingle-style residence in Brookline’s coveted Fisher Hill neighborhood, offering 6 bedrooms, 4 full bathrooms, and three half-baths. The home blends wonderful period character, architectural details, and thoughtful modern updates, with abundant natural light throughout. An oversized front porch welcomes you into a gracious foyer highlighted by a handsome period staircase. The main level features a fireplaced living room with built-in bookcases and window seats, a fireplaced dining room with built-in china cabinets, a library/home office, and a first-floor den/family room. The large eat-in kitchen offers generous space for everyday living and entertaining. The upper levels offer well-proportioned bedrooms and en-suite bathrooms. Additionally, the third floor provides flexibility for guests, in-law/au pair suite, recreation or working from home. With a separate entrance, the basement level includes spaces for an office or gym and storage/workshop/recreation space. A new slate roof and copper gutters were completed in 2016. A distinctive, meticulously maintained Fisher Hill home offering gracious scale, exceptional period detail, and versatile living space in one of Brookline’s most desirable neighborhoods.

115 Dean Rd, Brookline

Listing courtesy of Listing Agent: Eileen Strong O Boy from Listing Office: Hammond Residential Real Estate.

$1,700,000

5 Beds ⋅ 4 Baths ⋅ 73583014 MLS

Attached Corner Townhouse Sun-Filled Living, offers four bedrooms across four thoughtfully designed levels, complemented by a private patio and two composite decks. Wall-to-wall sliders flood the home with natural light while framing beautiful panoramic treetop and sky views.Behind its classic brick exterior, the home offers a spacious and distinctive interior with an impressive blend of character, comfort, and modern convenience. The kitchen features stainless steel appliances, an induction range, French-door refrigerator, and granite countertops. Custom built-ins and generous closet space provide exceptional storage throughout. Mitsubishi mini-split heat pumps in every room provide efficient year-round heating and cooling. The lower-level bedrooms feature private walk-out access, offering flexibility for guests, a home office, or additional living space.Located on a picturesque, tree-lined street that combines historic charm with modern urban living, the property is just steps from the C and D Line T, grocery stores, restaurants, and neighborhood amenities. A rare opportunity to enjoy privacy, natural light, outdoor space, and exceptional city convenience in one of the area’s most desirable neighborhoods.

184 Rawson Road, Brookline

Listing courtesy of Listing Agent: Azeddine Fadli from Listing Office: Property Navigator.

$2,195,000

4 Beds ⋅ 4 Baths ⋅ 73581080 MLS

RARELY AVAILABLE: A premier single-family alternative, this sun-drenched, spacious 4 BR, 3.5 BA, END-UNIT townhome with exclusive TWO-CAR GARAGE and a PRIVATE BACKYARD with patio sits on desirable tree-lined Fuller Street near Coolidge Corner in the Florida Ruffin Ridley (FRR) school district. Features 2,915 sq. ft. of versatile space, appointed with 2 en-suite bedrooms and 3 zones of climate-controlled heating/cooling. /// MAIN LEVEL: Enter via keypad entry into a graceful foyer with beautifully refinished hardwood floors and a powder room for guests. Cook's kitchen boasts polished granite countertops, dual sinks, gas cooking, pantry, and sunlit eat-in breakfast area, flowing seamlessly into an expansive, open dining and living area with large windows including direct slider access to the exclusive-use fenced backyard—a private oasis perfect for outdoor dining and play! /// SECOND & THIRD LEVELS: The second level features 3 bedrooms and 2 full baths, including a serene, large en-suite with balcony and huge closet. Atop the stairs, a skylight naturally brightens the third floor with an even larger primary bedroom suite complete with full bath and enormous closet, ideal as an owner's suite, guest sanctuary, executive home office, media room, or lavish gym. /// LOWER LEVEL: The finished lower level provides flexible bonus space perfect for play, additional fitness space, or a quiet office, with dedicated laundry and tremendous storage capacity. /// PARKING: Unparalleled Brookline parking includes an adjacent 2-car garage with ample storage for skis, bikes, and gear, a 3rd off-street driveway space, plus 2 association visitor spots! /// UPDATES & LOCATION: Key updates include refinished hardwoods, newer HVAC, newer roof, fresh interior paint, and radon remediation system. (Note: Contractor estimate in-hand for $20k to transition 2nd/3rd floor carpets to matching hardwood). Unbeatable location is only 0.5 miles to FRR K-8, blocks to Clear Flour Bakery, Coolidge Corner, and the B/C Green Lines, offering lifestyle convenience and rapid access by T or car to Longwood Medical, Boston, Cambridge, and nearby suburbs. /// HOA: Low $600/mo HOA fee in a 100% owner-occupied 4-unit association. Cross-listed as Condominium under MLS #73581067. Private showings by appointment.

231 Fuller St, Brookline

Listing courtesy of Listing Agent: Josh Ehrenfried from Listing Office: Clear Path.

$4,250,000

6 Beds ⋅ 7 Baths ⋅ 73580905 MLS

Exquisitely renovated and restored in 2016, this architecturally significant fieldstone-faced attached single family marks the perfect confluence of historic charm, modern luxury, and a wildly desirable location in the heart of Brookline’s Washington Square area. Spanning more than 5700 sq ft of spectacular living space, this property serves as a master class in timeless craftsmanship and a showcase for beautifully curated fixtures and finishes. The main level, graced with 11’ ceilings, features an elegant entry foyer with a fireplace and built-in benches flanked by a spacious bay-front living room with diamond-paned glass detailing & an addl. fireplace. The dining room is an entertainer's paradise with bespoke built-in bar & coffee stations, a gas fireplace, and French doors to a professionally landscaped deck/oasis with irrigation. The open-plan kitchen is a true showstopper, outfitted with floor to ceiling cabinetry, marble countertops, premium appliances, a stone-capped island, and a luminous breakfast area. A sculptural central staircase with a multi-level modern glass chandelier leads to the second level, equipped with a luxe primary suite w/ a gas fireplace, marble bath w/ bidet, and multiple walk-in closets. This level also includes a spacious alternative primary suite equipped with a Murano glass chandelier, fireplace, built-in office, marble bath and laundry. Three more beautiful bedrooms or offices and a sleek modern bath comprise the third level. The sun-drenched top level aerie or art studio, currently used as a media / family room, features its own dedicated bath and triple walk-in closets. Downstairs, the well-appointed fully walkout garden level offers an expansive ensuite guest / in-law space; a play room or lounge; 1.5 renovated baths; an auxiliary laundry room or kitchenette w/ gym space; and ample storage. An enviable mud room boasts French doors and access to a professionally landscaped covered patio / dining area plus parking for 2-3 vehicles. Extensive infrastructure upgrades since 2016 include electric rewiring with 400amp service; five-zone HVAC with hydro air; gut renovations of the kitchen and five+ marble baths; repointing; basement remodeling; slate work; professional landscaping and irrigation; wiring for hi-speed Internet; mesh WiFi; Sonos sound system; & a new sewer line. Coveted location near top-tier shopping, dining, the C & D Green Lines; Longwood Medical; public & private schools. An exceptional opportunity.

362 Tappan St, Brookline

Listing courtesy of Listing Agent: Elisabeth Preis from Listing Office: Compass.

$1,495,000

3 Beds ⋅ 3 Baths ⋅ 73579467 MLS

Beautifully sited on a picturesque tree-lined street, this sun-filled multi-level Mid-Century Ranch offers the perfect blend of timeless style and modern updates. The open concept living and dining areas feature hardwood floors and a striking stone fireplace, creating an inviting space for everyday living and entertaining. A bright four-season sunroom overlooks the private backyard, extending the living space year-round. This well-maintained home offers 3 bedrooms, renovated baths, central air conditioning, a home office that can easily serve as a guest bedroom, and a large finished lower level. Additional highlights include direct entry from the one-car garage, hardwood flooring, and abundant natural light. Enjoy outdoor living on the backyard patio surrounded by a private yard with a built-in outdoor fireplace, perfect for relaxing or entertaining. Ideally located near Baker School, with easy access to Putterham Circle, the Longwood Medical Area, and The Street, this desirable location offers convenience, amenities, and a wonderful neighborhood setting.

109 Wallis Road, Brookline

Listing courtesy of Listing Agent: Jayne Friedberg from Listing Office: Coldwell Banker Realty - Brookline.

$23,000,000

6 Beds ⋅ 12 Baths ⋅ 73576839 MLS

An extraordinary opportunity to own one of Brookline's most prestigious estates, set on nearly 1.75 acres in the most coveted location. This majestic brick Georgian Colonial has been masterfully renovated with museum-quality craftsmanship and timeless architectural detail. Offering over 16,000 sq. ft. of elegant living space, the home features a grand two-story foyer, 6 bedrooms, 9 full and 3 half baths, a gourmet kitchen, oversized fireplaced living room, formal dining room, Parisian-inspired bar, tea room, mahogany library, and a dramatic two-story family room with a spiral staircase leading to a private office. The exceptional primary suite offers dual spa-like baths, two walk-in closets, and a private office.The lower level features a media room,50's billard and bar area, wine cellar ,en suite bedroom with sitting area ,fitness room and indoor pool. Resort-style grounds include professionally landscaped park-like gardens, a 4-car garage, 2 swimming pools, a full pool cabana with kitchen, living room and full bathroom and a lighted tennis court. A truly iconic estate offering unparalleled luxury and timeless elegance.

381 Warren Street, Brookline

Listing courtesy of Listing Agent: The Jeff Groper Group from Listing Office: Coldwell Banker Realty - Newton.

$4,100,000

5 Beds ⋅ 5 Baths ⋅ 73575238 MLS

These newly built luxury townhomes WITH ELEVATORS are a down-sizers dream but are spacious enough for a family. The rear residence offers the privacy and feel of a single-family home with its own private elevator, garage parking, and private yard. Magnificent open-concept living and entertaining areas, a chef's kitchen with sleek cabinetry and professional-grade appliances, and high-end finishes throughout. This 5 bedroom, 4.5 bathroom residence is right in the heart of COOLIDGE CORNER with all the bells and whistles. Walk to your favorite restaurants, shops, and parks. Schedule a private showing today!

125 Fuller Unit 125, Brookline

Listing courtesy of Listing Agent: The Matskevich Group from Listing Office: William Raveis R.E. & Home Services.

$1,395,000

3 Beds ⋅ 2 Baths ⋅ 73575003 MLS

This newly renovated 3 bedroom 2 Bath Chestnut Hill ranch offers all the amenities. This 2,370 square foot home is move in ready and has a great layout for easy living. A brand new kitchen with modern appliances, outside sunroom, and great outdoor patio makes this a wonderful home for entertaining. Additional flex space on the ground floor leaves room for a playroom, home office, or extra room to relax and unwind. Walkable to Putterham circle, close to schools, library and other community spaces. Come see this new home and all that it has to offer.

91 Grove, Brookline

Listing courtesy of Listing Agent: Eric Seitz from Listing Office: The Statesmen Group, LLC.

$1,295,000

3 Beds ⋅ 2 Baths ⋅ 73574339 MLS

A rare opportunity to own a beautifully updated home in one of Brookline’s most sought-after locations! This charming 3-bedroom, 2-bath residence offers a wonderful blend of classic character, modern updates, and versatile living space. The thoughtfully renovated kitchen features contemporary finishes and functionality, while both bathrooms have been beautifully updated for today’s lifestyle. Gleaming hardwood floors throughout add warmth and timeless appeal. A flexible bonus room provides endless possibilities as a fourth bedroom, home office, guest space, or creative studio—perfect for adapting to your needs. The inviting layout offers comfortable everyday living while providing plenty of space for entertaining. Location is truly exceptional. Situated just a few blocks from the Brookline Hills Green Line T station for quick access to downtown Boston and surrounding neighborhoods are easily accessible without sacrificing the charm and convenience of Brookline living. Enjoy close proximity to local to all the major hospital at Longwood Medical, shops, restaurants, parks, hospitals, and everyday amenities. Adding to the home's unique appeal, the property directly abuts Lincoln School, offering an uncommon level of convenience and connection to the surrounding neighborhood. With its prime location, renovated kitchen and baths, beautiful hardwood floors, flexible bonus space, and easy access to Boston, this is an opportunity you won't want to miss. Come see why 428 Boylston Street could be the perfect place to make home!

428 Boylston St, Brookline

Listing courtesy of Listing Agent: Victor Divine from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.

$3,695,000

4 Beds ⋅ 5 Baths ⋅ 73573585 MLS

Welcome to this stunning center-entrance Colonial in Brookline's Chestnut Hill estate area, set on a level half-acre lot. This expansive home features 4+ bedrooms, 4 full and 1 half baths & offers over 4,895 square feet across three finished levels. The foyer opens to a fireplaced living room and a formal dining room that seats 12. The Chef’s kitchen features a Wolf range, Sub-Zero refrigerator, double wall ovens including steam, Cove dishwashers, two sinks, custom cabinetry & granite counters. A library with built-ins cabinetry sits off the dining room & kithcen. The family room, with gas fireplace opens through French doors to a bluestone patio and a broad, fenced, level yard. Upstairs, the primary suite includes a private balcony, Carrara marble bath, dressing area, and two walk-in closets. Three additional bedrooms and two full baths & laundry complete the floor. The lower level consists of a media/playroom, gym, wet bar, beautiful full bath with glass enclosed shower + another set of laundry. Central air & Sonos throughout, EV charging & 2-car garage. Close proximity to the D Line at Chestnut Hill, shops and restaurants at The Street at Chestnut Hill, Soule Playground, and Dane Park.

17 Glenoe Rd, Brookline

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

$2,595,000

5 Beds ⋅ 5 Baths ⋅ 73573502 MLS

ABSOLUTELY INCREDIBLE OPPORTUNITY AT THIS PRICE!!!!!! A rare combination of character, space, and setting in Chestnut Hill, this beautifully maintained Cape sits on a scenic half-acre with approximately 3,900 SF, 5 bedrooms, and 4.5 baths. Enter into a home filled with classic period details, wide-plank floors, and abundant south-facing light. The gracious living room welcomes with a fireplace and French doors opening to the patio, while the spacious family room features custom built-ins. At the heart of the home, an updated eat-in kitchen flows into a comfortable sitting area and opens directly to the backyard. A convenient mudroom leads to the driveway and two-car garage.Upstairs, the sun-filled primary suite offers an en-suite bath and private balcony, joined by four additional bedrooms, including a second primary, a study, and three full baths. Private guest quarters with separate stair access add flexibility. The lower level offers laundry, recreation space, and storage. Step outside to discover a pool surrounded by mature landscaping, a spacious patio, and peaceful grounds that create a private oasis.Set along beautiful Woodland Road, a leafy, tree-lined neighborhood with a welcoming community atmosphere, the setting is ideal for walking and running beneath towering oaks and mature trees. Dane Park, a wooded town park with trails, is within walking distance, while Wegmans, The Shoppes at Chestnut Hill, SuperLux, and an array of shops and restaurants are just minutes away. Convenient access to major routes also makes commuting easy, including a direct surface-road connection to Cambridge. With its distinctive character, generous scale, flexible layout, and exceptional outdoor setting, this is a property that truly needs to be experienced in person.

284 Woodland Road, Brookline

Listing courtesy of Listing Agent: The Denman Group from Listing Office: eXp Realty LLC.

$1,599,000

3 Beds ⋅ 2 Baths ⋅ 73573430 MLS

Nestled on a tree-lined Brookline block, this beautifully updated, move-in ready residence seamlessly blends timeless mid-century elegance with crisp, contemporary charm. Impeccable design and beautifully curated fixtures and finishes distinguish every inch of this elegant home. The expansive formal living room, graced with a fireplace and picture window, flows easily into the open-plan dining area and kitchen. It also connects to an inviting first floor family room. Remodeled in 2025, the airy open kitchen is outfitted with quartz countertops, a large central island, a Wolf range, and modern appliances. A gorgeous new window and an ingenious Dutch door offer great sight lines to the stone patio and generous backyard / garden from the kitchen and dining area. The main level also offers three spacious bedrooms including a luxurious primary suite with a walk-in closet and a fully renovated ensuite bathroom that balances vintage charm with modern touches. The two other main level bedrooms share a second full bathroom. The versatile walkout lower level, recently re-finished, includes a convenient office, gym or flex guest space, a spacious rec room or play room, a picture-perfect laundry room with a built-in sink and storage, and direct access to the attached garage. Numerous infrastructure upgrades over the last few years include a new heat pump / AC system on the main level, new blown-in insulation, recessed lighting, refinished hardwood floors, updated fixtures, interior paint and wallpaper, and Pex plumbing in the kitchen and primary bath. Exterior updates include a newly mechanized garage door, extensive landscaping, and new window-boxes and house numbers. This property is located in Brookline's desirable Baker School area convenient to Putterham Circle, Chestnut Hill shopping, public and private schools, the golf course, and the Putterham Library. Enjoy a quick commute to downtown and Longwood. A wonderful opportunity to land in a thoughtfully renovated, turn-key home at an affordable price in a beloved Brookline neighborhood!

154 Bellingham Rd, Brookline

Listing courtesy of Listing Agent: Elisabeth Preis from Listing Office: Compass.

$4,500,000

5 Beds ⋅ 6 Baths ⋅ 73572602 MLS

An artful balance of historic character & modern design, this 5,423SF 5BD, 5.5BA 1891 Colonial Revival was meticulously renovated in 2017 and is set on .41AC of landscaped grounds. Oversized windows, tall ceilings, bespoke millwork, detailed crown moldings, & 4 fireplaces highlight the home’s craftsmanship. Welcoming entry w/ FP connects main floor. Bright living room w/ FP and dining room w/ French doors that lead to wraparound deck. Renovated open kitchen w/ island, pantry, and eat-in. Adjoining family room w/ gas FP & built-ins. 1/2BA & mudroom complete level. Upstairs is the primary suite w/ FP, spa-like bath, & walk-in closet, en-suite bedroom, add’l bedroom, full bath, & laundry. Flexible 3rd floor flex w/ 3 add’l rooms & bathroom - ideal as bedrooms, offices, or play space. Walkout lower level w/ private entrance, en-suite bedroom, 2nd kitchen, family room, & storage. Private setting w/ tiered grounds, bluestone patio, & extensive lawn framed by mature trees & seasonal plantings

50 Sumner Road, Brookline

Listing courtesy of Listing Agent: Hilary Maddox Team from Listing Office: Compass.

$2,765,000

5 Beds ⋅ 4 Baths ⋅ 73572599 MLS

Come fall in love with this storybook 5-bed, 3.5-bath Colonial Revival set on 0.3AC in Brookline’s Chestnut Hill. Built in 1926, this charming 4,028SF residence offers a layout tailored for modern living. Streaming southern sunshine, timeless architecture, 3 fireplaces, and oversized windows define the home. Welcoming entry connects the main living spaces. Gracious living room w/ fireplace and built-ins flows into bright conversatory. Opposite is a family room with fireplace, which opens to a bright dining room. Classic butler’s pantry connects to the kitchen. With ample counter space and a cozy eat-in area, the kitchen serves as the heart of the home with direct access to deck and yard. Mudroom and half bath complete floor. Upstairs has bright en-suite primary, 4 additional bedrooms, office, and 2 full baths. Walkout lower level with playroom and laundry. Attached garage. Landscaped grounds create a true sense of privacy. Close to “The Street”, top schools, and Green D line train.

401 Heath Street, Brookline

Listing courtesy of Listing Agent: Hilary Maddox Team from Listing Office: Compass.

$1,649,000

4 Beds ⋅ 3 Baths ⋅ 73572511 MLS

Captivating colonial tastefully designed for elegant entertaining and comfort in mind. Privacy + nature abound in this 4 bedrooms, 3 bathrooms + 2450 square feet of refined living space in a premier Chestnut Hill location. Near Baker Elementary school (grades K-8) + close proximity to Putterham Shops, tennis, golf, wildlife sanctuary, Longwood Medical Area, Arnold Arboretum + Jamaica Pond. First floor has living room with wood burning fireplace, family room, bedroom with full bath + access to expansive outdoor deck. In the heart of the residence is a beautifully renovated kitchen with custom white shaker cabinets, sleek black granite countertops, stainless steel appliances + generous center island. Upper level has a sprawling primary bedroom suite complimented by majestic sunset views + an abundance of attributes such as walk-in closet, separate sitting area + spa-like bath with dual sink vanity, glass enclosed shower + soaking tub/jacuzzi. Additional finished lower level provides versatile space for a fitness gym, home theatre or home office to meet today's evolving lifestyle needs. One car garage, one carport + plenty of additional driveway parking make this an ideal residence to call home.

133 Wolcott Road, Brookline

Listing courtesy of Listing Agent: Mary Lochner from Listing Office: Coldwell Banker Realty - Brookline.

$11,750,000

6 Beds ⋅ 6 Baths ⋅ 73570794 MLS

One of Brookline’s most exceptional offerings in over a decade, this remarkable 1929 Colonial Revival estate is set on two beautifully landscaped acres in the town’s prestigious estate area. The 14-room residence offers 7,500 square feet of living space and showcases timeless architecture and exceptional craftsmanship. Set atop a private drive marked by stately stone pillars, the home is surrounded by sweeping lawns, specimen trees, perennial gardens, and a tranquil man-made freshwater creek. An inviting in-ground pool enhances the serene outdoor setting. Inside are six spacious bedrooms, four full baths, and two half baths, including a luxurious primary suite with a spa-like bath. Elegant formal rooms flow seamlessly into comfortable living areas, ideal for both grand entertaining and everyday living.Offering rare privacy with exceptional convenience, this distinguished property is located less than five miles from Back Bay.

71 Sears Road, Brookline

Listing courtesy of Listing Agent: Chamberlain Group from Listing Office: Coldwell Banker Realty - Brookline.

$3,095,000

5 Beds ⋅ 3 Baths ⋅ 73570606 MLS

Set on .92AC in Brookline’s Estate area, this 5BD, 3BA home was ahead of its time. Built in 1850 as the carriage barn of the Old Greenhill Estate, it was converted to a single-family and extensively reimagined with open living spaces, expansive glass, and a strong connection to the landscape. 2,834SF home enjoys southwest light throughout, with long sight lines to the outdoors & rooms that feel distinct yet flow naturally together. Oversized windows & glass doors open to backyard. Kitchen connects to the dining area w/ fireplace, while a family room with built-ins & a vaulted living room with 2nd fireplace offer flexible gathering spaces. 2 main-level bedrooms and a full bath add versatility. 2nd floor offers primary suite w/ treetop views and en-suite bath. 2 add’l bedrooms, full bath, and laundry complete 2nd floor. LL w/ mudroom, storage, & access to 2-car garage. Outside, mature trees, open lawns, seasonal gardens, and privacy create a rare setting just minutes from Boston.

185 Warren Street, Brookline

Listing courtesy of Listing Agent: Hilary Maddox Team from Listing Office: Compass.

$2,395,000

4 Beds ⋅ 5 Baths ⋅ 73569446 MLS

Set along one of Chestnut Hill’s picturesque tree-lined streets, this handsome brick Tudor offers a thoughtful blend of classic architecture, generous proportions & comfortable everyday living. A welcoming foyer introduces elegant living & dining rooms with hardwood floors & distinctive period details, while the spacious eat-in kitchen, with abundant cabinetry, updated appliances & wet bar, opens naturally to a relaxed family room with direct access to the backyard. Upstairs, four well-proportioned bedrooms include a generous primary suite overlooking the backyard, complete with a sizable walk-in closet & ensuite bath. A second ensuite bedroom, along with two additional bedrooms, provides flexibility for family, guests or a home office. The lower level offers versatile space for recreation, hobbies, storage or future expansion, with convenient access to the garage. Outdoors, a tiered backyard creates a private setting with a pool, deck & lawn, offering multiple spaces for entertaining, relaxing & enjoying the warmer months. Fresh paint, new and refreshed flooring & an updated back deck enhance the home’s appeal while preserving its distinctive character. Ideally situated in the Baker School District, with easy access to Route 9, shopping, dining & the amenities of Chestnut Hill, this is a home with both an inviting sense of place & room to make it your own.

72 Beverly Rd, Brookline

Listing courtesy of Listing Agent: Ovesen Group from Listing Office: Coldwell Banker Realty - Brookline.

$3,700,000

6 Beds ⋅ 5 Baths ⋅ 73561991 MLS

292 Clinton Road is a timeless Victorian residence, built in 1892 and prominently situated in Brookline’s Fisher Hill neighborhood. Rich in architectural detail, this meticulous home has been thoughtfully updated while preserving elegance and craftsmanship. A welcoming front porch leads to a gracious foyer with soaring ceilings, abundant natural light and original woodwork. Designed for grand entertaining and comfortable everyday living, the first floor features a fireplaced living room, dining room, family room with a bay window, a renovated Chef’s kitchen, pantry, mudroom and half bath. A stunning staircase leads to the second level, with a charming sun-drenched landing and a wall of glass. The primary suite offers a custom walk-in closet, and renovated en-suite bath, accompanied by two additional good-sized bedrooms with en-suite baths and a second-floor laundry room. The third floor offers flexibility with three additional bedrooms, a full bath, and a spacious room ideal for a home office.

292 Clinton Rd, Brookline

Listing courtesy of Listing Agent: Luan White from Listing Office: Coldwell Banker Realty - Brookline.

$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.

$2,299,000

4 Beds ⋅ 4 Baths ⋅ 73537709 MLS

Newly staged!!! 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.

$11,750,000

6 Beds ⋅ 9 Baths ⋅ 73536353 MLS

A rare opportunity to reimagine and create a $20+M compound in Brookline, set on two private acres in the coveted estate area. Conceived by an award-winning architect, the proposed design masterfully blends timeless elegance and exceptional craftsmanship with the features most desired for modern living soaring ceilings, abundant natural light, clean architectural lines, and a thoughtfully designed floor plan ideal for both grand entertaining and everyday comfort. The proposed plans showcase an expansive open-concept kitchen and family room with a dramatic cathedral ceiling, elegant formal living and dining rooms, spacious library, a screened porch, a gracious 1st floor bedroom, and an exceptional 2nd floor primary suite. Additional customization options include an elevator servicing all levels, a golf simulator, and a swimming pool. Offering rare privacy with exceptional convenience, this distinguished property is located less than five miles from Back Bay

Sears Road, Brookline

Listing courtesy of Listing Agent: Chamberlain Group from Listing Office: Coldwell Banker Realty - Brookline.

$4,650,000

6 Beds ⋅ 7 Baths ⋅ 73532609 MLS

Exceptional 2016 brick Colonial offering 6,359 sq. ft. of beautifully finished living space with 6 bedrooms, 6.5 baths, including a main-level bedroom suite, and a heated 3-car garage. Set on a private, professionally landscaped .38-acre level lot on a quiet, tree-lined street in desirable Chestnut Hill, this meticulously maintained home offers generous scale, modern amenities and move-in-ready condition.A grand two-story foyer introduces the light-filled main level, where 10' ceilings, hardwood floors and detailed millwork complement well-proportioned rooms. An elegant living room with fireplace connects to the formal dining room and a butler’s pantry with sink, dishwasher and extensive cabinetry.The open kitchen features a center island, premium appliances, custom cabinetry and dining area, and flows directly into the spacious family room with fireplace and floor-to-ceiling windows overlooking the grounds. French doors open to stone patios and the expansive lawn perfect for outdoor entertaining. A powder room and mudroom with built-in cubbies and access to the garage complete this floor.Upstairs, hardwood floors continue throughout. The spacious primary suite features a fireplace, large walk-in closet, generous bath and oversized windows overlooking the grounds. Four additional bedrooms, including two with ensuite baths and one currently used as an office, plus a full bath, laundry room and open landing with Juliet balcony complete the second floor.The expansive finished lower level provides additional space for recreation, work and entertaining, including a home theater/game room with bar, exercise room, private office, full bath, wine room ready for customization and ample storage, with bulkhead access to the backyard.Solar panels installed in 2026 provide energy savings and net-metering benefits. Convenient to public and private schools, shopping, dining, golf, and Boston, this substantial Chestnut Hill residence offers an exceptional combination of space, privacy, condition and modern functionality.

129 Rangeley Rd, Brookline

Listing courtesy of Listing Agent: Ingvild Brown from Listing Office: Keller Williams Realty.

$8,200,000

6 Beds ⋅ 9 Baths ⋅ 73526856 MLS

Set on over 1.2 acres with a 1.62-acre experience via a neighboring easement, this exceptional Chestnut Hill estate offers a tranquil oasis on one of the area’s most coveted and secluded streets. Originally built in 1900 and thoughtfully renovated over time, the residence spans more than 9,300 square feet with six bedrooms, six full bathrooms, and three half bathrooms. Its richly detailed living spaces were designed for both elegant entertaining and everyday comfort. Gracious formal rooms, soaring ceilings, and exquisite millwork overlook beautifully landscaped grounds featuring a heated, in-ground pool, a basketball court, and ample parking. Once home to Alvan T. Fuller, the 50th Governor of Massachusetts, the property carries remarkable historic provenance. The grounds were originally designed by Frederick Law Olmsted, further contributing to the property’s timeless character. This is a rare opportunity to own a historic estate of this scale in an unbeatable location.

40 Singletree Rd, Brookline

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

$4,795,000

4 Beds ⋅ 5 Baths ⋅ 73520842 MLS

Nestled on a private 0.92-acre lot in the prestigious Chestnut Hill neighborhood, this exceptional custom-designed Mid-Century Modern ranch, inspired by the timeless architecture of Frank Lloyd Wright, offers a rare blend of sophistication, privacy, and seamless indoor-outdoor living. Thoughtfully designed with gracious proportions and walls of glass, the home is filled with natural light and overlooks beautifully landscaped grounds. A spectacular four-season breakfast room with four skylights complements the chef’s kitchen featuring top-of-the-line appliances, three ovens, two dishwashers, and custom cabinetry. The luxurious primary suite serves as a private sanctuary with dual showers and vanities, smart toilets, separate dressing areas, a soaking tub, and an attached office/library. The versatile lower level with separate entrance offers excellent potential for an in-law suite. Sliding glass doors line the rear of the home, opening to a serene outdoor retreat with an elegant patio and heated pool. Superb Chestnut Hill location with easy access to Boston, shopping, dining and Medical Centers.

9 Singletree Rd, Brookline

Listing courtesy of Listing Agent: Deborah M. Gordon from Listing Office: Coldwell Banker Realty - Brookline.

$3,750,000

4 Beds ⋅ 4 Baths ⋅ 73518363 MLS

Stunning, four-bedroom, 3.5-bath townhouse delivering three levels of luxury living, plus an additional unfinished lower level, and the ease of a private elevator serving all four floors. The open-concept main level features a showpiece chef’s kitchen with Taj Mahal Quartzite countertops, custom cabinetry, and state-of-the-art appliances, flowing seamlessly into the living and dining spaces, perfect for entertaining. Upstairs, the primary suite is a true retreat with a spa-like bath, custom walk-in closet, and private balcony. Generous additional bedrooms offer flexible space for family and guests, while the third floor is ideal for an au pair suite, multiple home offices, or a cozy lounge. Enjoy private outdoor patio space and private balcony. A rare ground-up new construction in Brookline, finished with high-end millwork and truly custom design, built to be enjoyed for decades.

40 Stedman Street, Brookline

Listing courtesy of Listing Agent: Nathan Klairmont from Listing Office: Concept Properties.

$3,495,000

5 Beds ⋅ 5 Baths ⋅ 73516646 MLS

Spectacular single-family alternative. This side-by-side Contemporary Luxury townhouse, newly constructed in 2017, features all the luxury you would expect. Sprawling living room and dining. The eat-in kitchen has custom cabinetry, Thermador appliances, and marble countertops. The kitchen has direct access to the large private/exclusive backyard, which spans two levels. There is a large patio and garden. There are 5 bedrooms and 4.5 baths. Large Primary has cathedral ceilings and an ensuite, featuring a double shower, double vanity, soaking tub, and radiant floor heating. Adjoining the primary is a large family/sitting room with sliders to the patio overlooking the back garden. There is a finished lower level with a large family room and a large bedroom, both with glass sliders for direct outdoor access. There is a convenient kitchenette as well. Playground directly across. Minutes to school, shopping, restaurants, and T. Convenient to Longwood Medical and Boston. 92 Walk Score.

90 Columbia, Brookline

Listing courtesy of Listing Agent: Sheila White from Listing Office: Compass.

$2,950,000

4 Beds ⋅ 3 Baths ⋅ 73514639 MLS

One of Brookline's most distinctive residences, this rare 1880 Carriage House near Coolidge Corner seamlessly blends historic architecture with thoughtfully integrated modern updates. A 2022 landscape by Curbs Studio, inspired by Japanese zen gardens, features terraced granite, custom stonework, Ipê decking, integrated lighting, mature plantings, an outdoor kitchen, and fire-pit lounge. Inside, 10.5' ceilings, exposed beams, a wood-burning stove, and tall French doors create dramatic, light-filled living spaces. Four vaulted-ceiling bedrooms and 2.5 baths include two beautifully renovated bathrooms by Feinmann Inc. (2021). Recent improvements include HVAC (2024), windows, retaining wall, paint, and EV charging. A remarkable alternative to new construction, and condos, offering timeless craftsmanship and modern comfort moments from Longwood Medical Area, Fenway Park, restaurants, parks, the MBTA, the Museum of Fine Arts, Boston, the Isabella Stewart Gardner Museum, and all of Boston!

7 Stetson Street, Brookline

Listing courtesy of Listing Agent: Sarah Reddick Shimoff from Listing Office: Compass.

$6,450,000

4 Beds ⋅ 4 Baths ⋅ 73508634 MLS

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. Exceptional location, close to Fisher Hill Park, Runkle School, public transportation, shopping, dining, an easy commute to Boston, Longwood medical area and Cambridge. Modifications to the plans subject to review and approval. Buyer to verify all information. Photos are renderings.Also available as a lot with foundation for $2,950,000.

9 Willard Road, Brookline

Listing courtesy of Listing Agent: Celine Sellam from Listing Office: Coldwell Banker Realty - Brookline.

$14,850,000

6 Beds ⋅ 8 Baths ⋅ 73507123 MLS

Privately set off Warren St, this exceptional Brookline estate spans over 3.6 acres of beautifully landscaped grounds and over 9,000 SF across four levels, with 6 bedrooms, 6 full and 2 half baths. A striking entry with a sweeping staircase leads to expansive, light-filled living and entertaining spaces rich with charm and detailed moldings. The main level features a mix of formal and informal spaces, multiple offices, and a beautifully designed kitchen with high-end appliances, custom cabinetry, and an eat-in dining area overlooking the grounds. Upstairs, the primary suite includes a luxurious bath and generous dressing rooms, along with five additional bedrooms, family room, and laundry. The serene third floor offers flexible space for a gym, studio, or additional living. Outside, the grounds are unmatched - a pond, patios, firepit, and hot tub perfect for entertaining and everyday living. A one-of-a-kind offering in one of Brookline's most sought-after neighborhoods.

280 Warren St, Brookline

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

$3,790,000

4 Beds ⋅ 5 Baths ⋅ 73505387 MLS

RARE WATERFRONT OPPORTUNITY -- Direct and unbeatable water views of the 32-acre Brookline Reservoir Park. This one-of-a-kind sun-drenched contemporary home features spectacular scenic water and park views, decent upscale neighborhood and yet super convenience to city life. It is with a slate roof has a regal and elegant presence with a mahogany double-door main entrance. The light-color maple flooring throughout gives this home a soothing and pleasant ambiance. There are 3 master suites all with custom walk-in California closets, academic study areas and beautifully renovated and appointed bathrooms. The custom Poggenpohl kitchen is sleek and features all the bells & whistles to meet today's high end chef's standards. The floor plan is flexible allowing for easy living and entertaining. Special features also include a security system & a hydro-air Buderus boiler. Upon entering this house, you feel transported to a Zen peaceful sanctuary. Fabulous location, easy access to all that Brookline and Boston has to offer.

75 Lee Street, Brookline

Listing courtesy of Listing Agent: Weidong Li from Listing Office: WINN Real Estate & Consulting.

$6,400,000

4 Beds ⋅ 5 Baths ⋅ 73500458 MLS

A magnificent home located in the highly coveted estate section of Brookline directly across from the famed Country Club. 198 Clyde Street is a wonderful cape style estate perfectly adapted to modern living. The property offers 6,521 square feet of living space located on just under 1 acre of impeccably landscaped grounds. Beautifully appointed interiors include grand formal living and dining rooms overlooking the outdoor space, a gourmet kitchen, and a spectacular family room with double-height ceilings. The luxurious primary suite is complete with separate dressing rooms and bathrooms and direct access to an outdoor sitting area. The exterior is as wonderful as the interior with multiple outdoor patios, a sprawling lawn and a pergola. Additional features include a 2-car garage, laundry room, home office, wine cellar, wood paneled den and a custom hockey training area. This outstanding home is minutes from Larz Anderson, Dexter/Southfield, Park School, and The Street at Chestnut Hill.

198 Clyde Street, Brookline

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

$8,995,000

7 Beds ⋅ 6 Baths ⋅ 73496969 MLS

Discover 39 Worthington Road in Brookline's coveted Cottage Farm neighborhood. This fully renovated masterpiece boasts 7 bedrooms and 5.5 bathrooms with impeccable craftsmanship and attention to detail. The interior, designed by a renowned interior designer has been featured in various publications. Wonderful spaces for entertaining and comfortable living include a large custom-designed chef's kitchen open to a gracious family room with custom millwork built-ins along with a large library with over 12' ceilings. There is a luxurious primary suite with a spa-like bath, walk-in closets, a sun-filled study, & access to a terrace. The lower level includes a gym, playroom, and more. Nestled on a double, extra-large expansive landscaped lot complete with a hockey rink (and equipment) and full outdoor kitchen, privacy and serenity, and indoor/outdoor living abound. The ideal setting and location that defines urban-suburban living close to all Boston/Cambridge/Brookline has to offer.

39 Worthington Rd, Brookline

Listing courtesy of Listing Agent: Rachel Goldman from Listing Office: MGS Group Real Estate LTD.

$2,480,000

5 Beds ⋅ 4 Baths ⋅ 73492578 MLS

This classic brick Colonial, set on one of Brookline’s most coveted streets near the Brookline Reservoir, offers stunning views and exceptional spaces for both family living and entertaining. This 5-bedroom, 3.5-bath home features a front-to-back living room with a gas fireplace, a gracious dining room with its own fireplace, and an eat-in kitchen that opens to a covered deck and patio—perfect for entertaining. The main level also includes a private home office, a powder room, and a sun-filled, oversized family room with direct access to a second patio. Upstairs on the 2nd and 3rd levels are five bedrooms and an additional home office, including a spacious primary suite with an ensuite bath, walk-in closet, and private deck. The lower level offers a dedicated exercise area, laundry room, abundant storage, and an attached two-car garage. Ideally located near The Street, Wegmans, Longwood Medical Area, public transportation, and Boston.

140 Dudley St, Brookline

Listing courtesy of Listing Agent: Deborah M. Gordon from Listing Office: Coldwell Banker Realty - Brookline.

$7,500,000

6 Beds ⋅ 8 Baths ⋅ 73487838 MLS

A rare find in Brookline, this property offers privacy and tranquility on a secluded lot adjacent to Sargent Estates. Spanning three finished levels plus a lower level, the home features 6 bedrooms and 6 full and 2 half baths, with meticulous craftsmanship and striking architectural details throughout. A grand rotunda entry leads to a chef’s kitchen, expansive living and dining rooms, family room, and mudroom. The second floor includes three bedroom suites, each with its own bath, plus two office spaces. The third floor offers two additional bedroom suites, while the lower level includes a sixth suite, gym, large family room, and laundry. Surrounded by mature landscaping and set well back from the street, the property boasts a pool, hot tub, sauna, outdoor fireplace, pizza oven, and full outdoor kitchen—an exceptional setting for both relaxation and entertaining. Not to be missed!

1 Chestnut Place, Brookline

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

$6,695,000

7 Beds ⋅ 9 Baths ⋅ 73486175 MLS

Set on nearly an acre within Brookline’s coveted Estate Section, this extraordinary 2015-built residence offers a rare blend of privacy, scale, & exceptional construction rarely found in today’s market. Spanning nearly 8,000 sq ft including a finished lower level, the home features solid mahogany floors,marble baths, custom granite stonework, 7 bedrooms, 9 bathrooms, a steam room, and multiple fireplaces including a striking outdoor granite fireplace on the covered rear deck for year-round entertaining. A fully restored original Carriage House provides two additional floors ideal for a gym, studio, or guest quarters, while a separate private office or nanny suite offers its own entrance. Built to an impressive standard with geothermal heating and cooling across six zones, radiant floor heating, Andersen Architectural Series windows, 600-amp electrical service, EV charging, and extensive CAT5 wiring. Minutes to The Country Club, Dexter Southfield, Larz Anderson Park, and downtown Boston

75 Goddard Avenue, Brookline

Listing courtesy of Listing Agent: Samantha Stumpo from Listing Office: Serhant.

$1,750,000

4 Beds ⋅ 4 Baths ⋅ 73482825 MLS

Charming 1927 Tudor located in the highly desirable Chestnut Hill area of Brookline! This beautifull home offers timeless character with modern amenities. The first floor features a spacious living room with fireplace, formal dining room, eat-in kitchen, and a convenient half bath—perfect for everyday living and entertaining. The second floor includes four generously sized bedrooms, two full baths, an additional half bath, and a steam shower, creating a comfortable and functional layout. Additional highlights include central air conditioning, a private deck, two-car built-in garage, and a walk-up attic offering excellent potential for future expansion. Ideally situated near Chestnut Hill Mall, the Longwood Medical Area, and the MBTA Chestnut Hill stop, this home provides exceptional access to shopping, dining, major employers, and public transportation. A rare opportunity in one of Brookline’s most sought-after neighborhoods!

764 Hammond St, Brookline

Listing courtesy of Listing Agent: Kevin Gingras from Listing Office: Conway - West Roxbury.

Brookline, MA Single Family Properties for Sale

Newest Brookline, MA Single Family Homes for Sale

How much is your home worth?

How much is your home worth?