Brookline MA 4 Bedroom Real Estate, Homes, Condos for Sale

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

$2,550,000

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 73591365 MLS ⋅ 3,498 SqFt.

Luxury upper-level duplex residence on a quiet one-way street in the heart of Washington Square, offering approximately 3,500 sq. ft. of thoughtfully designed living space. This elegant home features 5 bedrooms, 4 full bathrooms, and an open floor plan ideal for both everyday living and entertaining. The sun-filled living and dining area showcases a marble fireplace and opens to a spacious private deck with sweeping Boston skyline views. The chef's kitchen is equipped with premium appliances, including a Wolf range, a breakfast bar, and abundant workspace. The spacious primary suite features a private balcony, marble bath with an oversized Jacuzzi tub, radiant heated floors, and custom closets. A second ensuite bedroom also offers a private balcony, while additional bedrooms provide flexibility for guests, a home office, or family living. Additional highlights include four private outdoor decks and balconies, hardwood floors, central air, laundry on the 2nd floor, custom built-ins and closets, a built-in surround sound system, Nest thermostats, abundant natural light, and two outdoor parking spaces. An elevator provides convenient access from the parking area to the main entrance. Ideally located just moments from Washington Square's restaurants, cafés, shops, the MBTA Green Line (C Branch), and the Driscoll School, this exceptional residence offers a rare combination of luxury, space, and convenience in one of Brookline's most desirable neighborhoods.

91 University Rd Unit 2, Brookline

$1,600,000

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73591294 MLS ⋅ 2,254 SqFt.

Flooded with natural light, this elegant 4-bedroom, 2-full-bath condominium offers over 2,200 sq ft of expansive living across the second & third floors of a two-family home. Beautiful hardwood floors, recessed lighting, period details, & a flexible layout provide a gracious setting for both relaxed living & stylish entertaining. A fireplace anchors the inviting living family room, while the updated kitchen features sleek quartz countertops. The stunning open-concept top floor showcases soaring cathedral ceilings with 3 new skylights, creating an airy, sun-filled retreat. The oversized primary bedroom is a peaceful sanctuary with a walk-in closet & its own private porch—an inviting spot for morning coffee or unwinding at day’s end. A second private porch extends from a rear bedroom, offering another quiet outdoor escape. Shared gardens add charm & greenery, while basement storage, garage parking, plus 1 additional parking space bring everyday convenience to this distinctive Brookline residence. Conveniently located near the Green Line’s C branch & Washington Square’s shops & restaurants.

146 University Rd Unit 146, Brookline

$1,695,000

4 Beds ⋅ 2 Baths ⋅ CONTINGENT Status ⋅ 73590092 MLS ⋅ 1,923 SqFt.

Classic Back Bay graciousness in a beautiful courtyard setting. This corner residence offers four exposures and an abundance of natural light, blending timeless architectural charm with spacious, comfortable living. The inviting floor-through layout features four generously sized bedrooms with high ceilings, oak hardwood floors, two renovated baths, and the living room area includes a room for den/family. A delightful dining room with classic wainscoting flows into a bright, welcoming kitchen appointed with custom cabinetry, Corian countertops, and stainless-steel appliances. Additional highlights include newer windows, in-unit laundry, two private storage rooms, and access to a stunning roof deck. Ideally located near the Longwood Medical Area, parks, schools, and public transportation, with convenient access to Boston University, Cambridge, and the vibrant shops, cafés, and restaurants of Coolidge Corner and Beacon Street.

4 Alton Court Unit 3, 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

$1,199,000

4 Beds ⋅ 2 Baths ⋅ UNDER AGREEMENT Status ⋅ 73581877 MLS ⋅ 2,108 SqFt.

Discover the potential of this expansive 2,100+ square foot penthouse in the heart of Coolidge Corner. Set within a classic brownstone, this elegant residence offers a flexible layout featuring 4 bedrooms, 2 baths, an office, and sun-drenched interiors that blend historic charm with a blank-canvas opportunity. The grand foyer, complete with original built-ins, leads to a sprawling living area and a formal dining room adorned with a preserved china cabinet and decorative moldings. Freshly painted and boasting gleaming hardwood floors throughout, the home includes an eat-in kitchen, dedicated laundry room, lots of large closets and storage and a private covered balcony. Whether you’re looking to customize a spacious new home or secure a high-performing investment property, this condo delivers character and scale in a coveted location. Nestled between St. Marks and Griggs Parks and one block from the T (GreenLine C), this vibrant Brookline neighborhood offers amazing shopping, arts, restaurants, cafes and a consistently top rated school district with newly constructed state-of-the-art schools. Condo is pet friendly. Bring your vision or your contractor and reimagine the possibilities of this very special unit!

97 Marion Street Unit 5, Brookline

$1,600,000

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73581197 MLS ⋅ 1,654 SqFt.

Classic early 1900s rowhouse unit at the base of Aspinwall Hill, steps to Washington Square, renovated and converted in 2017. Well-appointed second-floor home with a flexible layout, featuring large, open kitchen, dining, and living spaces, and four bedrooms, or three-plus-office. Spacious walk-in closet, double vanity, and tiled shower at the primary suite. Well-appointed hallway full-bathroom. Private rear deck off the fourth bed/office. Plentiful closet space; custom Elfa built-in shelving. Hardwood floors throughout, with trim and moulding details, and large windows for plentiful natural light. Storage area in the basement. Rental parking regularly available nearby. Well-run, fully owner-occupied Association. Half a block to Washington Square, dense with celebrated eateries, and the Green Line (C Branch); walkable to Schick Park, Brookline Village, and Coolidge Corner; easy to Downtown.

177 Winthrop Road Unit 3, 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

$2,195,000

4 Beds ⋅ 4 Baths ⋅ UNDER AGREEMENT Status ⋅ 73581067 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 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 Single Family under MLS #73581080. Private showings available upon request.

231 Fuller St Unit 231, Brookline

$1,199,000

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73577718 MLS ⋅ 1,825 SqFt.

This Pill Hill beauty is conveniently located near the heart of Brookline Village, the Longwood medical area and public transportation. Combining old world elegance with modern amenities, this floor-through sophisticated brownstone home is sure to delight the lover of Victorian romanticism and grandeur with its intriguing charm and captivating refinement. Gorgeous 11-foot high ceilings, huge closets, custom-built armoires and linen closet, upgraded windows, new appliances, quartz countertops, center kitchen island, in-unit laundry and central air complement the stunning original details that include elaborate crown molding, ornate marble fireplaces, artfully embellished cast iron radiators, transom windows, pocket doors, and huge windows throughout (replaced 2016). The oversized living room is open to the formal dining room with bow windows with a seamless passage through handsome pocket doors, and both rooms feature beautifully carved marble fireplaces. Inviting and spacious primary suite with fireplace, bay windows, double closets and en suite bath. Recent 2026 updates include newly refinished hardwood floors, new quartz countertops, many new appliances, and new light fixtures. Pet friendly. Basement storage included, and rental parking available in the area. Easy access to Brookline Village shopping and MBTA Green D line, Northeastern, the MFA, Leverett Pond, Olmsted Park, Emerald Necklace, Symphony Hall, the Cypress Street Playground and the Brookline Avenue Playground. A commuter’s dream! ***1 TRANSFERABLE RENTAL CARPORT PARKING SPOT RIGHT ACROSS THE STREET; see broker about a SECOND PARKING SPOT.

17 High Street Unit 2, Brookline

$3,295,000

4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 73577586 MLS ⋅ 3,292 SqFt.

Modern penthouse living with private outdoor space and exceptional parking in Brookline’s Coolidge Park enclave. Built from the ground up in 2021, this 3,292 sq ft duplex pairs four en-suite bedrooms with generous gathering spaces and refined finishes. A high-ceiling corner living room and European-style kitchen each open to a covered deck, extending daily living outdoors, while the spacious dining area centers on a gas fireplace. Upstairs, the primary suite offers a luxurious bath and generous closet space, alongside three additional bedrooms, each with a private bath. A private, fenced level yard adds another outdoor retreat. Direct garage access, two heated garage spaces, and room for up to two additional cars on the heated driveway bring uncommon convenience. Set within a distinctive five-street neighborhood with tree-lined streets and a local park, close to Coolidge Corner’s shops and dining, with convenient access to Longwood and Boston.

78-80 Verndale Unit 80, 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

$1,950,000

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73577225 MLS ⋅ 2,616 SqFt.

A rare opportunity to own a beautifully maintained traditional two-family home on a desirable, tree-lined residential street. Offering exceptional flexibility for multigenerational living, an owner-occupant seeking rental income, or an investment property, this inviting home combines classic character with thoughtful updates. Both spacious apartments feature welcoming entry halls, living rooms with fireplace, sunrooms, elegant dining rooms with double china cabinets, renovated kitchens with granite countertops, tile floors and stainless-steel appliances, two bedrooms, and a full hall bathroom. The second-floor residence offers exciting expansion potential in the walk-up attic. Glowing natural woodwork, hardwood floors and custom cabinetry add warmth and timeless appeal throughout. Outdoor living includes a welcoming front porch, second-floor deck, and patio in a backyard. A spacious basement with extensive storage and laundry, along with a two-car garage and wide driveway, offers exceptional convenience for parking and storage. Ideally located near the Brookline Hills T, Brookline High School, Lincoln School, Brookline Reservoir, parks, cafés, markets, and shops, with easy access to the Longwood Medical Area and Downtown Boston. An active neighborhood association further enhances this vibrant and welcoming community.

36 Milton Road, Brookline

$2,295,000

4 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73576053 MLS ⋅ 2,571 SqFt.

Welcome to this beautiful and sun-filled four-bedroom home in an exceptional Coolidge Corner location. New in 2016 this thoughtfully designed residence offers generous living space, wonderful natural light, and an inviting flow that makes everyday living and entertaining effortless. The main level features an open kitchen, spacious dining and living area, a charming reading nook, and a half bath. A private den/office provides the perfect space for working from home, reading, or quiet time. The spacious ensuite primary bedroom is also conveniently located on this level. Upstairs, 3 generously sized bedrooms and a full bath offer plenty of room for family and guests. A laundry room completes this level. Large windows throughout the home bring in beautiful natural light, creating a bright and welcoming atmosphere. Garage parking and a spacious private patio provide indoor/ outdoor living in the heart of Brookline. Just moments from the restaurants, shops, cafes, parks, and vibrant energy of Coolidge Corner, this home is in an ideal location in one of Brookline's most desirable neighborhoods.

131 Winchester St Unit 131, 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

$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

$2,499,000

4 Beds ⋅ 4 Baths ⋅ CONTINGENT Status ⋅ 73572859 MLS ⋅ 2,894 SqFt.

SIGNIFICANT PRICE ADJUSTMENT! This exceptional 4-bedroom, 3.5-bath duplex is nestled on a historic, tree-lined street just steps from vibrant Coolidge Corner and close proximity to the Longwood Medical area. Thoughtfully designed for comfortable family living, this residence includes the two upper floors and boasts nearly 2,900 sq ft of sunlit space with windows on every side. The private entrance welcomes you along a charming cobblestone path bordered by lush perennial gardens. Inside, an open floor plan connects a chef’s kitchen—complete with high-end cabinetry, stainless steel appliances including a 6 burner gas range—to the inviting family room with a cozy fireplace. The living room’s fireplace and direct access to a private deck make entertaining effortless. The main level also features a home office, spacious guest suite with fireplace, and stylish powder room. Upstairs, unwind in a tranquil primary suite, two additional bedrooms, a flexible bonus room and laundry closet. Enjoy central A/C, hardwood floors, ample storage, two parking spaces under a pergola, and more. Discover the perfect blend of style, livability and location! Please reach out to realtor for a list of property improvements.

51 Sewall Ave Unit 2, 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

$2,299,000

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 73570781 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 2-1, 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

$2,999,000

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

$2,150,000

4 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73561839 MLS ⋅ 2,489 SqFt.

Welcome to your dream home in the heart of Coolidge Corner. This spacious 4-bedroom, 3-bath residence blends timeless character with everyday comfort. An inviting, sun-filled foyer with southern exposure welcomes you inside. Entertain with ease in the expansive living and dining rooms, highlighted by a decorative fireplace and original moldings. The large eat-in kitchen offers abundant storage and plenty of space for preparing and sharing meals. A versatile sunroom is perfect as a home office, nursery, or relaxing retreat. Generous closet space throughout provides exceptional storage. Take in breathtaking city views from the shared roof deck, the perfect setting to watch Boston's iconic fireworks or unwind with a glass of wine. Ideally located on the Green Line and just minutes from downtown Boston, Longwood Medical Area, and all that Brookline has to offer, this exceptional condo delivers convenience at every turn.

1272 Beacon Street Unit 2, Brookline

$2,100,000

4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 73560438 MLS ⋅ 3,193 SqFt.

TWO CAR GARAGE: This exceptional contemporary townhome offers 3,193 square feet of sophisticated living space in the heart of Chestnut Hill. Located in the highly desirable Brookline school district, this four-bedroom, four-and-a-half-bath residence combines refined contemporary design, premium finishes, and the comfort of single-family living with the convenience of condominium ownership.Bathed in natural light from oversized black-framed windows, the open-concept main level features 8-inch white oak hardwood flooring, soaring ceilings, and a beautifully appointed chef's kitchen with custom cabinetry, quartz countertops, premium stainless steel appliances, a six-burner Bosch gas range, and an oversized center island overlooking the dining and living areas. Sliding glass doors open to a private patio and fenced yard, creating seamless indoor-outdoor living, while a stylish tiled powder room completes the main level.The second level features two spacious en-suite bedrooms, including a luxurious primary suite with a custom walk-in closet and spa-inspired bath featuring elegant tilework and a frameless glass shower. The top level offers two additional en-suite bedrooms, a striking glass-enclosed office, and a dedicated laundry room.Additional highlights include designer lighting, a tiled mudroom with custom built-ins, abundant storage, and two assigned heated garage parking spaces.Moments from The Street Chestnut Hill, Chestnut Hill Square, Hammond Pond Reservation, Skyline Park, Route 9, Longwood Medical Area, and downtown Boston. Never occupied, this extraordinary residence offers a rare opportunity to own a turnkey luxury home in one of Brookline's most sought-after neighborhoods.

811 Heath St Unit Rear, Brookline

$3,750,000

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 73556250 MLS ⋅ 2,924 SqFt.

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

$1,949,000

4 Beds ⋅ 3 Baths ⋅ EXTENDED Status ⋅ 73552409 MLS ⋅ 1,949 SqFt.

Sun-drenched 2025 new construction home offering an exceptional blend of modern design and functionality. This spacious residence features a thoughtfully designed open floor plan with 4 bedrooms, 3 bathrooms, and a versatile den, huge roof-deck, all complemented by stunning ceiling height and abundant natural light. The high-end kitchen with gas stove is beautifully finished stainless steal appliances, designer cabinetry, and elegant tile work that carries throughout the home. Unwind in your private exclusive Roof-deck, or entertain at your kitchen island that fits 6 chairs. The property also offers the convenience of 4 total parking (2 of which garage). Ideally located across from a park and just moments from Jamaica Pond, restaurants, bus lines, and local amenities, this residence delivers the best of modern living in a vibrant neighborhood.

57-59 Highland Rd Unit 59, Brookline

$2,420,800

4 Beds ⋅ 4 Baths ⋅ UNDER AGREEMENT Status ⋅ 73550522 MLS ⋅ 2,746 SqFt.

Motivated Seller! Last unit left!Welcome to the epitome of elegance.Historic Chateauesque 1890's "Brookline Castle" has been gut renovated to its full grandeur!The one-of-a-kind exterior stonework is a rarity in Brookline.Open up to a gorgeous foyer from the private elevator that also runs thru the entire building & brings you to every level of your new home.The kitchen & dining area features oversized windows that flood the space with natural sunlight.The chefs kitchen boasts custom cabinetry, sparkling white Bianco Carrara marble countertops, intentionally designed for functionality & style.Adjacent to the kitchen and dining area is the living room, with a beautiful gas fireplace & marble mantle.The rich woodworking & walnut hardwood floors span over 3 floors, 4 spacious bedrooms & 3 baths all fitted with marble tile & marble mosaics.The roof has calming views of nature & foliage.The location is highly sought after, just steps to restaurants, cafes, public transit,hospitals & major highways!

324 Tappan Unit PH, 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

$2,799,000

4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 73542360 MLS ⋅ 3,768 SqFt.

From the white picket fence and private yard to the oversized covered front porch, this exceptionally renovated townhome welcomes with charm before you even step inside. Enter into the open kitchen featuring custom cabinetry and quartz countertops, anchored by a soaring 4-story floating staircase with custom lighting that sets the tone for everything that follows. Each room has its own distinct features, including a spacious bow-front living room with gas fireplace, generous bedrooms, and a luxurious primary suite with vaulted ceilings and soaking tub. The 2nd floor offers 2 en suite bedrooms, 1 has an oversized private deck. The lower level includes a 2nd living room, 4th bedroom and bonus room ideal for an office/gym. Each bedroom includes a walk-in closet (some with 2), Hunter Douglas blinds and engineered wide-plank hardwood floors. Located by Clear Flour Bakery, the Green Line, and all that Coolidge Corner has to offer, this move-in ready home is as convenient as it is impressive.

177 Thorndike St Unit 1, 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

$2,295,000

4 Beds ⋅ 4 Baths ⋅ UNDER AGREEMENT Status ⋅ 73524730 MLS ⋅ 2,663 SqFt.

A breathtaking, gut-renovated luxury condominium in the coveted heart of Coolidge Corner. This stunning, sun-drenched residence showcases an expansive open-concept layout, soaring ceilings, and exceptional architectural detail throughout. The sleek, state-of-the-art chef’s kitchen features top-of-the-line appliances, custom cabinetry, and premium finishes—perfect for both everyday living and elegant entertaining. Four generously sized bedrooms and three and a half beautifully designed baths complete this sophisticated urban retreat, offering the ultimate blend of modern luxury, style, and comfort. There is a large patio off the kitchen for private entertaining. Also included are laundry hook ups in the unit and two outside spaces. Very close to public transportation and shopping.

116 Thorndike St Unit 1A, Brookline

$4,795,000

4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 73520842 MLS ⋅ 6,790 SqFt.

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

$3,750,000

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 73518363 MLS ⋅ 2,924 SqFt.

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

$2,950,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73514639 MLS ⋅ 2,000 SqFt.

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

$2,699,999

4 Beds ⋅ 4 Baths ⋅ UNDER AGREEMENT Status ⋅ 73510090 MLS ⋅ 2,763 SqFt.

Superbly positioned between Brookline Village and Coolidge Corner, this elegant 4 bedroom residence occupies one of two units within a multi-family property, offering refined living in a top notch Brookline setting. Originally built in 1885, meticulously renovated in 2026 by a Premier Brookline Developer, the home balances historic architectural character with modern sophistication. Throughout the residence, high end finishes, beautiful hardwood floors, and abundant natural light create a warm yet polished atmosphere. 10" Foot ceilings. Spanning the second and third floors, the two level layout features gracious living and dining rooms, along with a well-appointed kitchen featuring a breakfast area and direct access to a private deck. A guest bedroom completes the main level. The upper floor is dedicated to private living, offering a primary bedroom with walk-in closet and bathroom, two additional bedrooms each with their own bathrooms, and laundry. An exceptional property and location

21 Kent Square Unit 2, Brookline

$6,450,000

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 73508634 MLS ⋅ 4,825 SqFt.

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

$3,790,000

4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 73505387 MLS ⋅ 6,498 SqFt.

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

$6,400,000

4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 73500458 MLS ⋅ 6,521 SqFt.

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

$3,100,000

4 Beds ⋅ 4 Baths ⋅ UNDER AGREEMENT Status ⋅ 73493723 MLS ⋅ 3,261 SqFt.

Price to SELL: Newly renovated 3,250+ SF residence delivers sweeping skyline views from Cambridge to Back Bay, four private outdoor spaces, and the scale of a single-family home. The expansive second floor main living level includes 3 bedrooms, 2.5 baths, a central kitchen perfect for entertaining, formal dining room, large living room, office, laundry, and two balconies. The private upper-level primary suite features a sitting room with wet bar and a spectacular roof deck with gas BBQ connections. Direct entry from two attached garage parking spaces (wired for EV) and accessed from a private mudroom. Outdoor space includes exclusive-use 470+/- SF yard. . Exceptional design, premium finishes, and modern convenience in one of Brookline’s most sought-after location. Plans and engineering to add elevator shaft and elevator addition available.

197 Winchester Street Unit 1, Brookline

$1,999,000

4 Beds ⋅ 2 Baths ⋅ UNDER AGREEMENT Status ⋅ 73491100 MLS ⋅ 2,116 SqFt.

Located on a beautiful tree-lined street in Coolidge Corner, this elegant 4-bed, 2-bath, 2,116 sq ft condo in a stately limestone brownstone combines modern refinement with period grandeur. Elevated above the street for privacy, the gracious foyer with fireplace opens to a sun-drenched living room with leaded glass transoms, crown molding, and spectacular inlaid hardwood floors. The wainscoted dining room with custom built-ins seats a crowd. The renovated kitchen offers quartzite counters, custom cabinetry, marble tile, and a sun-filled eat-in area. Both marble bathrooms feature radiant heat floors and towel warmers; one adds a soaking tub. The primary suite enjoys two exposures and a spa-like en-suite bath. Three additional bedrooms, private home office with French door, in-unit laundry, and a vast private basement storage room complete the picture. Convenient to acclaimed dining, boutique shopping, top schools, the Green Line, and Longwood Medical.

7 Parkman St Unit 1, Brookline

$1,750,000

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 73482825 MLS ⋅ 3,000 SqFt.

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

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