Brookline MA Single Family Real Estate, Homes for Sale

4 Beds ⋅ 4 Baths ⋅ NEW Status ⋅ 73595643 MLS ⋅ 4,345 SqFt.

Situated in prestigious Chestnut Hill along the Brookline line, this exceptional location offers convenient access to some of the area’s most sought-after private schools, including Dexter Southfield, The Park School, The British International School of Boston, Beaver Country Day, and Brimmer & May. Enjoy the advantages of this coveted neighborhood, including Boston’s comparatively favorable property taxes, proximity to the renowned Longwood Medical Area, Brigham and Women’s Faulkner Hospital just down the street, and easy access to some of the country’s most prestigious universities. This fully renovated, sprawling ranch-style home lives like new construction, blending modern luxury with a super contemporary flare. Perfect for families looking for proximity to the Dexter School, Park School, The British School, Beaver Country Day and Brimmer & May School. The home features four bedrooms, plus a dedicated gym and sauna. The stylish kitchen showcases stainless steel appliances, sleek finishes, and an open-concept layout flowing seamlessly into the living room, anchored by a striking Frank Lloyd Wright-inspired fireplace.Three generously sized bedrooms feature custom built-ins, complemented by an expansive laundry room and a beautifully appointed bathroom with a double vanity. The private primary suite offers a luxurious retreat with a private bathroom including solid stone surround, glass enclosed shower with jets and soaking tub complimented by contemporary style fixtures with a custom walk-in closet.The finished lower level adds exceptional versatility, with heated floors throughout, a full bathroom & bedroom, additional space for recreation, fitness, spa like treatment in your indoor built-in sauna and a massive addtional living space perfect for an entertainment area. Outside, enjoy a private patio and abundant green space on a desirable corner lot, along with a spacious two-car garage and an irrigation system. A rare opportunity to enjoy the feel of new construction in one of Boston’s most sought after, highly desirable neighborhoods.

101 Hackensack Road, Brookline

$849,900

3 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 73594577 MLS ⋅ 1,401 SqFt.

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

$2,799,999

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 73592951 MLS ⋅ 3,225 SqFt.

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

$5,250,000

6 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 73592699 MLS ⋅ 7,028 SqFt.

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

$8,400,000

7 Beds ⋅ 8 Baths ⋅ ACTIVE Status ⋅ 73592560 MLS ⋅ 8,540 SqFt.

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

$5,398,000

5 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 73592351 MLS ⋅ 7,058 SqFt.

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

$34,000,000

7 Beds ⋅ 16 Baths ⋅ ACTIVE Status ⋅ 73590483 MLS ⋅ 19,138 SqFt.

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

$995,000

3 Beds ⋅ 2 Baths ⋅ CONTINGENT Status ⋅ 73590431 MLS ⋅ 1,350 SqFt.

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

$4,250,000

5 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 73590255 MLS ⋅ 6,313 SqFt.

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

$2,875,000

5 Beds ⋅ 3 Baths ⋅ CONTINGENT Status ⋅ 73590203 MLS ⋅ 2,900 SqFt.

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

$2,350,000

6 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 73587355 MLS ⋅ 5,030 SqFt.

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

$3,999,000

8 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 73586478 MLS ⋅ 4,166 SqFt.

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

$2,395,000

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 73584176 MLS ⋅ 2,800 SqFt.

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

$3,500,000

6 Beds ⋅ 7 Baths ⋅ UNDER AGREEMENT Status ⋅ 73584015 MLS ⋅ 4,891 SqFt.

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

$1,500,000

3 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73584001 MLS ⋅ 1,741 SqFt.

Charming Brookline Colonial tucked along a quiet, tree-lined street in a convenient neighborhood setting. An inviting front porch welcomes you into a home filled with character, recently painted interiors and beautifully refinished hardwood floors. The main level features a living room, dining room, and kitchen with direct access to a generous rear deck overlooking the level backyard, creating an ideal extension of the living space. Upstairs are three well- proportioned bedrooms and a full bathroom. The finished lower level offers flexible space for a family room/playroom, home office, along with a full bath and laundry area. A walk-up attic provides additional storage. A detached garage adds convenience. Close to Eliot Recreation Center, Warren Field, neighborhood schools, shops, and the Green Line, with easy access to Boston.

31 Loveland Rd, Brookline

$1,700,000

5 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 73583014 MLS ⋅ 2,460 SqFt.

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

$2,195,000

4 Beds ⋅ 4 Baths ⋅ UNDER AGREEMENT Status ⋅ 73581080 MLS ⋅ 2,915 SqFt.

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

$4,250,000

6 Beds ⋅ 7 Baths ⋅ ACTIVE Status ⋅ 73580905 MLS ⋅ 5,739 SqFt.

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

$1,175,000

2 Beds ⋅ 2 Baths ⋅ UNDER AGREEMENT Status ⋅ 73579776 MLS ⋅ 1,240 SqFt.

Tucked away at the end of a long private drive, this detached residence at Sargent Estates offers the privacy and feel of a single-family home with the ease of condominium living. The thoughtfully designed, single-level floor plan features beautifully refinished hardwood floors and an open kitchen with white cabinetry, quartz countertops, stainless steel appliances and a center island. The kitchen flows seamlessly into the dining and living areas, creating an inviting setting for everyday living and entertaining. French doors from the living area open to an oversized patio bordered by lawn and mature landscaping. Two spacious bedrooms include a primary suite with a full bath. Additional highlights include generous storage, a cedar closet and an attached two-car garage. Association amenities include an in-ground pool, landscaping and snow removal. Convenient to public transportation, the Longwood Medical Area and downtown Boston.

18 Chestnut Pl, Brookline

$1,495,000

3 Beds ⋅ 3 Baths ⋅ CONTINGENT Status ⋅ 73579467 MLS ⋅ 2,100 SqFt.

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

$2,650,000

5 Beds ⋅ 5 Baths ⋅ UNDER AGREEMENT Status ⋅ 73577527 MLS ⋅ 2,986 SqFt.

Architectural character and modern convenience converge in this thoughtfully updated five bedroom, three full and two half bath Colonial with a two-car garage in Brookline’s beloved Fisher Hill neighborhood. Built in 1926, the house showcases beautifully restored woodwork with Arts and Crafts influences, yet it is wonderfully outfitted for twenty-first century living. The inviting main level living space features elegant built-ins and a clever concealed projector screen for effortless entertaining. The handsome formal dining room, which flows easily into both the kitchen and the first-floor family room, is equipped with an elegant modern chandelier and wainscoting. Outfitted with a Wolf range, a built-in office/homework station and a central island for easy gathering, the contemporary kitchen connects to an expansive deck. A charming sun room or family room and a compact half bath round out this level. The second floor offers three lovely bedrooms, an office, and two beautiful full baths both renovated to the studs in 2018. The primary bedroom is ensuite and features double closets. Wonderful details abound throughout this level, including a built-in bench and a vintage decorative fireplace with Delft tile in a second bedroom. On the third floor, there are two more welcoming bedrooms and a third full bath. The walkout level currently includes a finished gym or office with luxury vinyl plank flooring and recessed lighting, plus great storage, an older half bath, and a generous laundry room. The house is equipped with numerous infrastructure upgrades, including 200 amp electrical service and two zones of high-velocity HVAC. 23 new Marvin windows were installed in 2017. Just outside, the property offers a generous fenced yard and access to the two-car garage.This property is ideally situated in one of Brookline’s most convenient locations, with access to premier shopping and dining a stone’s throw away in Washington Square and Cleveland Circle. Both the C and D lines of the Green Line are close at hand. This location also provides excellent access to amenities in Coolidge Corner, Brookline Village, and downtown. Runkle School is a block away, and it is also convenient to various private schools and Brookline High School. Enjoy an easy commute to Longwood Medical area and downtown Boston.

249 Clinton Rd, Brookline

$2,100,000

4 Beds ⋅ 4 Baths ⋅ UNDER AGREEMENT Status ⋅ 73577381 MLS ⋅ 4,102 SqFt.

Location, location, location! Enjoy the convenience of Aspinwall Hill from a beautiful tree-lined street, with Brookline High School, Green Line stations, Washington Square, Star Market, parks, shops, and dining all nearby. Coolidge Corner is also close by, with convenient access to the Longwood Medical Area, Boston, and surrounding communities.Set on a beautifully landscaped 11,217 sq. ft. (.26-acre) lot, this property offers a rare opportunity to purchase a home with generous outdoor space in a highly desirable Brookline location at an attractive price point. The home is ready for thoughtful updates and offers the flexibility to renovate over time, reconfigure existing spaces, or expand in the future if desired, subject to applicable zoning, permitting and Town approvals.The existing split-level residence offers approximately 4,102 sq. ft. across two levels, including an oversized 751 sq. ft. two-car garage. The 2,099 sq. ft. main level includes a kitchen, open family and dining room with fireplace and sliding doors to the terrace and backyard, four bedrooms and two full and one half bath, including a primary bedroom with ensuite bath. The layout offers strong potential for a larger open-concept kitchen, dining and family area with direct connection to the terrace and gardens.The approximately 2,003 sq. ft. lower level, including the garage, provides substantial additional flexibility with two rooms suitable for offices or other uses, a playroom/home theater, half bath, laundry, utility room and direct garage access.An opportunity to personalize an existing home, expand for additional living space, or create something entirely new in one of Brookline’s most desirable residential settings.

205 Gardner Rd, Brookline

$23,000,000

6 Beds ⋅ 12 Baths ⋅ ACTIVE Status ⋅ 73576839 MLS ⋅ 16,856 SqFt.

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

$4,100,000

5 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 73575238 MLS ⋅ 3,502 SqFt.

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

$1,395,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73575003 MLS ⋅ 2,370 SqFt.

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

$1,295,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73574339 MLS ⋅ 1,748 SqFt.

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

$3,695,000

4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 73573585 MLS ⋅ 4,884 SqFt.

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

$2,595,000

5 Beds ⋅ 5 Baths ⋅ CONTINGENT Status ⋅ 73573502 MLS ⋅ 3,913 SqFt.

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

$1,599,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73573430 MLS ⋅ 2,607 SqFt.

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

$5,150,000

4 Beds ⋅ 5 Baths ⋅ UNDER AGREEMENT Status ⋅ 73573266 MLS ⋅ 5,744 SqFt.

An elegant English-inspired Gothic Revival residence in Brookline’s coveted Fisher Hill neighborhood, distinguished by steep slate roofs, dramatic gables and arched architectural and copper details. Designed for Mrs. Harold Hammond by noted architects Kilham, Hopkins & Greeley, whose work also includes the Devotion School (Florida Ruffin Ridley School) and Brookline High School (source: Brookline Preservation Commission), this stately home offers 5,744 sq. ft. of living space across four finished levels, with 4 bedrooms, 3 full and 2 half baths, 5 fireplaces and an attached 2-car garage.The main level features a welcoming kitchen with convenient side entry, dining room with fireplace, gracious living room with fireplace, a light-filled sunroom overlooking the serene garden, two offices and powder room. The exceptional walk-out garden level is designed for both everyday living and entertaining, anchored by a dramatic two-story family room with fireplace, custom built-in bookcases, wet bar, floor-to-ceiling windows and French doors opening to a stone patio and private backyard. A wine cellar and lounge, exercise room, powder room and direct garage access complete this level.Upstairs, the generously scaled primary suite features a fireplace, walk-in closet and private outdoor balcony. Two additional bedrooms, a full bath and laundry complete the second floor. The finished top floor offers two spacious and versatile rooms—ideal for bedrooms, offices, hobbies or recreation—along with a full bath and abundant storage.Set on .35 acres, the beautifully landscaped private grounds offer mature specimen trees, stone walls, lawns and peaceful spaces for outdoor dining, entertaining and play. Meticulously maintained and thoughtfully updated over the years, the home combines period character with comfortable, move-in-ready living and exceptional storage throughout.A quiet and secluded setting on a tree-lined street, yet remarkably convenient to Washington Square, Cleveland Circle, schools, parks, public transportation (C & D lines), shopping and Boston.

67 Hyslop Rd, Brookline

$1,199,000

2 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73572983 MLS ⋅ 1,572 SqFt.

Tucked away in a peaceful setting, yet just moments from Brookline Village, this charming and beautifully maintained condominium lives like a single-family home. The welcoming first level offers an open yet cozy layout with living and dining areas, a well-appointed kitchen, and a powder room. High ceilings, beautiful wood floors, and large windows fill the space with natural light and enhance its inviting character. The second floor is comprised of a generously sized bedroom and an updated marble-accented bathroom with a double vanity. On the third floor, you’ll find a second bedroom along with a bonus area ideal for an office, exercise space, reading nook, or creative retreat. The finished lower level provides excellent guest accommodations complete with a lovely full bathroom. A standout feature of this special home is the private 400+ sf patio—an exceptional outdoor space for relaxing, entertaining, or enjoying a morning coffee. Secure rental parking is just outside the front door.

50 Cameron Street, Brookline

$4,500,000

5 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 73572602 MLS ⋅ 5,423 SqFt.

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

$2,765,000

5 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 73572599 MLS ⋅ 4,028 SqFt.

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

$1,649,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73572511 MLS ⋅ 2,500 SqFt.

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

$2,175,000

5 Beds ⋅ 4 Baths ⋅ UNDER AGREEMENT Status ⋅ 73571974 MLS ⋅ 3,213 SqFt.

Gracious brick home in Brookline’s coveted Corey Hill neighborhood, freshly painted throughout with newly refinished hardwood floors. Abundant natural light and timeless architectural details create a warm and inviting backdrop for everyday living and entertaining. Generous living and dining rooms, a handsome fireplace, spacious bedrooms, a flexible floor plan, and an oversized attached garage offer exceptional comfort and versatility. Enjoy sweeping views of the Boston skyline and an exceptional location near Summit Park, with convenient access to the T, Coolidge Corner, and Brookline Village. Ideally located near the Longwood Medical Area and Boston’s renowned universities and hospitals. A rare opportunity to own a distinctive home in one of Brookline’s most sought-after neighborhoods.

77 Jordan Rd, Brookline

$11,750,000

6 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 73570794 MLS ⋅ 7,502 SqFt.

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

$3,095,000

5 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73570606 MLS ⋅ 2,834 SqFt.

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

$3,195,000

6 Beds ⋅ 6 Baths ⋅ UNDER AGREEMENT Status ⋅ 73570431 MLS ⋅ 5,487 SqFt.

This stunning Fisher Hill home is surrounded by spectacular gardens and offers over 5,400 square feet of living space. Featuring 6 bedrooms, 5 full baths, and 1 half bath, the home welcomes you with a expansive foyer and curved staircase. The warm and inviting living room boasts floor-to-ceiling windows, a fireplace, and French doors opening to the loggia. The dining room features a fireplace and bowed window overlooking the gardens. An expansive eat-in kitchen includes a center island and upholstered seating area. A bookshelf lined family room and half bath complete the first floor.Upstairs, the grand primary suite offers a walk-in closet, en-suite bath, and shared balcony with the second bedroom. There is a second bedroom on this floor that also includes an en-suite bath and the additional additional bedrooms share a faull bath. The third floor provides extra bedrooms and ideal home office space plus there is a full bath on this floor. The third floor also offers a large walk-in closet that is perfect for additional storage..Additional highlights include a finished basement with exercise room, office, and full bath, plus a two-car garage and beautifully landscaped yard and stone patio. Ideally located for easy access to Washington Square and the C and D line of the T. Convenient to the Runkle Elementary School, Whole Foods, Trader Joes and the shops and restaurants of Coolidge Corner.

17 Chesham Road, Brookline

$2,395,000

4 Beds ⋅ 5 Baths ⋅ CONTINGENT Status ⋅ 73569446 MLS ⋅ 4,067 SqFt.

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

$2,695,000

7 Beds ⋅ 4 Baths ⋅ UNDER AGREEMENT Status ⋅ 73568459 MLS ⋅ 4,805 SqFt.

Beautifully situated at the summit of Aspinwall Hill, this gracious, expansive Victorian home offers unique opportunities for the discerning buyer. Originally a single family, it was reconfigured to two units, with private entrances on opposite sides. The spacious yard is a gardener's delight. The front unit features high ceilings, hardwood floors, moldings, original woodwork, and lovely fireplaces. A foyer opens to the living room with a curved bay window, which leads to the formal dining room, also highlighted by bay windows, and finally to an updated kitchen with a large peninsula, ample wood cabinetry, great pantry space and a laundry area. Two bedrooms plus an updated full bathroom complete this level. Upstairs is a large primary bedroom, graced by a curved bay window, with a bright adjoining sitting room offering excellent closet space. Also on this level are another bedroom and an updated full bathroom, with a pristine soaking tub. The second unit offers an eat-in kitchen with 2 adjoining pantries, living room, and unique reading nook, plus 1/2 bath on one level, and 3 bedrooms plus a full bathroom on the upper level. Generous storage space throughout both units. Recently renovated Schick Park is very close by, as well as walking paths. Close proximity to Runkle School and Brookline High. Also nearby are shops, restaurants, public transportation, Star Market and Whole Foods.

71 Addington Rd, Brookline

$4,800,000

5 Beds ⋅ 6 Baths ⋅ UNDER AGREEMENT Status ⋅ 73567713 MLS ⋅ 4,324 SqFt.

221 Gardner Road is a beautifully designed young home offering modern living, exceptional quality, and a wonderful location in the heart of Brookline. Built in 2024 and further enhanced by the current owners, the property features extensive landscaping and thoughtfully designed outdoor spaces for everyday living and entertaining. Expansive windows bring in abundant natural light throughout the open floor plan. The spacious kitchen with a large center island flows seamlessly into the dining area and family room, with direct access to a stone patio and generous backyard. A first-floor bedroom with an en-suite bath offers flexibility for guests, family, or a home office. Upstairs, the spacious primary suite includes a spa-like bath and walk-in closet. Three additional en-suite bedrooms, a comfortable lounge area, and a laundry room complete this level. The lower level features a mudroom with direct access to the heated three-car garage with car charger. There is also the option to install an elevator servicing all floors. Ideally located close to Brookline schools, restaurants, shops, parks, and the MBTA Green Line.

221 Gardner Rd, Brookline

$2,999,000

4 Beds ⋅ 4 Baths ⋅ UNDER AGREEMENT Status ⋅ 73565107 MLS ⋅ 3,265 SqFt.

Located on coveted Fisher Hill, this charming residence set on 14,550 square feet of beautifully landscaped grounds, offers thoughtfully designed modern updates, newer systems, and the convenience of an attached garage. The gracious main level features a welcoming living room with fireplace, formal dining room, powder room, and a chef’s eat-in kitchen featuring custom cabinetry outfitted with a Thermador gas cooktop and warming drawer, GE Monogram double ovens, two Bosch dishwashers, two sinks, and a Sub-Zero refrigerator. The kitchen opens to a spacious, sun-filled family room with skylights and direct access to the lush, private backyard. A flag stone patio and gas hookup for grilling create an ideal setting for relaxed indoor-outdoor living. The second level features a generous primary suite with a newly renovated en-suite bath, complete with luxurious heated radiant floors and a skylight, along with three generous closets. Three additional well-proportioned bedrooms with substantial closet space and a full bath complete this level. The finished lower level provides versatile flex space for a gym, office/guest accommodations, playroom/den, along with a full bath, laundry area with refrigerator/freezer, and extra storage, all with 1- car garage access and additional 2 outdoor spaces. Ideally situated near Runkle School, Brookline High School, the Longwood Medical Area, Chestnut Hill Reservoir, and the MBTA Green Line C and D branches, with easy access to nearby shops, restaurants, and Route 9.

52 Clinton Road, Brookline

$5,900,000

9 Beds ⋅ 9 Baths ⋅ UNDER AGREEMENT Status ⋅ 73564889 MLS ⋅ 8,619 SqFt.

BROKER TOUR CANCELLED - ACCEPTED OFFER This 9-bedroom, 6 full/3 half bath residence spans 8,619 sq ft, blending timeless architectural character with thoughtful modern updates throughout. A stunning 2024-renovated kitchen with fireplace and radiant heated flooring anchors the home, complemented by a newly enclosed breezeway, cozy breakfast nook and gracious dining room with double French doors. Updated Pella windows enhance the home, while refinished hardwood floors and fresh paint create a beautifully refreshed interior. Designed with both everyday living and entertaining in mind, the home features a sunken living room with direct exterior access to the solarium and screened porch, creating a seamless connection between the interior and surrounding grounds. The greenhouse conservatory has been completely reimagined with honed absolute black stone, new tile flooring, and a custom fountain, offering a truly distinctive space within the home. Generous bedroom suites and thoughtfully updated baths provide privacy and comfort throughout. A private-entrance, attached in-law/au pair suite offers exceptional flexibility for guests or staff, while an epoxy-finished garage round out the home's modern improvements. Outdoors, a stone patio extends the home's entertaining space onto the expansive, level grounds, with the rare opportunity to add a pool and create a truly exceptional indoor-outdoor setting. Minutes to the Longwood Medical Area (8–10 min), Fenway (10–15 min), Back Bay (15–20 min), and Logan Airport (20 min), with Brookline Reservoir, Fisher Hill Reservoir Park, Larz Anderson Park, and the Emerald Necklace all nearby. A short drive delivers Chestnut Hill's premier shopping, dining, Equinox, and Wegmans. A once-in-a-generation offering.

372 Warren St, Brookline

$3,700,000

6 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 73561991 MLS ⋅ 4,350 SqFt.

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

$3,650,000

7 Beds ⋅ 5 Baths ⋅ UNDER AGREEMENT Status ⋅ 73558672 MLS ⋅ 4,726 SqFt.

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

111 Clinton Road, Brookline

$1,790,000

4 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73549795 MLS ⋅ 2,274 SqFt.

$200,000 PRICE REDUCTION!! Fantastic move-in-ready 4 bedroom, 2.5 bathroom in BROOKLINE. Set on a 15,000+ level private lot, LEAD FREE, perfect for INVESTOR or END USER, close to schools, shops, restaurants, public transportation, golf & Skyline Park with its trails, playgrounds, fields and other amenities. Filled with natural light, the main level has beautiful hardwoods, a fireplaced living room, lovely dining room, eat-in kitchen, family room, home office and guest bathroom. Upstairs are 4 very generous bedrooms. and a full hallway bathroom.The primary bedroom has vaulted ceilings, sky lights and, in addition to the large ensuite bathroom, a second separate dressing room with its own sink and vanity. The home's lower level has high ceilings and unlimited potential to be used as a gym, movie theatre or what ever your needs maybe. There is central a/c.The backyard is level and private, with an expansive deck off the kitchen and family room for entertaining. An attached 2 car garage and large driveway complete this offering.

75 Hammond Pond Parkway, Brookline

$2,399,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73547641 MLS ⋅ 3,243 SqFt.

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

$11,000,000

ACTIVE Status ⋅ 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

$2,299,000

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 73537709 MLS ⋅ 1,897 SqFt.

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

$11,750,000

6 Beds ⋅ 9 Baths ⋅ ACTIVE Status ⋅ 73536353 MLS ⋅ 10,000 SqFt.

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

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