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Welcome to 476 Heath Street, a classic 1899 Chestnut Hill residence renovated with care for how people live today. A stone walk and fieldstone wall lead to a covered entry porch. Inside, herringbone oak floors, original moldings and 5 fireplaces carry the home's character through every level. The main floor is made for gathering: a bay-window living room, a dining room and family room with coffered ceilings and fireplaces, French doors from the family room to the yard, a kitchen with a large island and breakfast bar, and a private home office. Upstairs, the primary suite offers a fireplace and a bath with double vanity, joined by 5 more bedrooms on the second floor, including one with its own full bath and 2 with walk-in closets. The third floor adds 3 more bedrooms and a full bath, including a private suite in its own separate wing, a flexible setup for a nanny or au pair, guests or extended family. In all, 9 bedrooms, 4 full and 3 half baths, including a marble bath and 2 beautifully tiled powder rooms. Outside, a covered back porch overlooks a large, private fenced yard. Central air, in-unit laundry, a 1-car garage and parking for 6 cars in total. Available now for a 12-month lease. Water, sewer, snow removal and grounds maintenance included.

9 Beds ⋅ 7 Baths ⋅ 73595995 MLS

Welcome to 476 Heath Street, a classic 1899 Chestnut Hill residence renovated with care for how people live today. A stone walk and fieldstone wall lead to a covered entry porch. Inside, herringbone oak floors, original moldings and 5 fireplaces carry the home's character through every level. The main floor is made for gathering: a bay-window living room, a dining room and family room with coffered ceilings and fireplaces, French doors from the family room to the yard, a kitchen with a large island and breakfast bar, and a private home office. Upstairs, the primary suite offers a fireplace and a bath with double vanity, joined by 5 more bedrooms on the second floor, including one with its own full bath and 2 with walk-in closets. The third floor adds 3 more bedrooms and a full bath, including a private suite in its own separate wing, a flexible setup for a nanny or au pair, guests or extended family. In all, 9 bedrooms, 4 full and 3 half baths, including a marble bath and 2 beautifully tiled powder rooms. Outside, a covered back porch overlooks a large, private fenced yard. Central air, in-unit laundry, a 1-car garage and parking for 6 cars in total. Available now for a 12-month lease. Water, sewer, snow removal and grounds maintenance included.

476 Heath St, Brookline

Listing courtesy of Listing Agent: Thawanna Pessoa from Listing Office: William Raveis R.E. & Home Services.

$4,350,000

BEST COOLIDGE CORNER LOCATION and Rarely available! Fully leased 6-unit brick building on a quiet side street steps from Harvard St in Coolidge Corner. Five 2-bedroom units and one 1-bedroom. Rents are well below market and there is a tremendous amount of value to add. Hardwood floors throughout, great lighting, and solid rental history. 7 Naples Rd is part of a 3 building association. Heat and Heat water are shared. Short walk to the Coolidge Corner Green Line C stop, Trader Joe’s, restaurants, with easy access to Longwood Medical area, Fenway, and Boston University. Rare chance to own a stabilized multifamily in one of Brookline’s most walkable neighborhoods. Showings by appointment with 48 hours notice to tenants.

11 Beds ⋅ 6 Baths ⋅ 73592780 MLS

BEST COOLIDGE CORNER LOCATION and Rarely available! Fully leased 6-unit brick building on a quiet side street steps from Harvard St in Coolidge Corner. Five 2-bedroom units and one 1-bedroom. Rents are well below market and there is a tremendous amount of value to add. Hardwood floors throughout, great lighting, and solid rental history. 7 Naples Rd is part of a 3 building association. Heat and Heat water are shared. Short walk to the Coolidge Corner Green Line C stop, Trader Joe’s, restaurants, with easy access to Longwood Medical area, Fenway, and Boston University. Rare chance to own a stabilized multifamily in one of Brookline’s most walkable neighborhoods. Showings by appointment with 48 hours notice to tenants.

7 Naples, Brookline

Listing courtesy of Listing Agent: Jacob Simmons from Listing Office: City Realty Group.

$5,250,000

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.

6 Beds ⋅ 5 Baths ⋅ 73592699 MLS

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

46 Powell Street, Brookline

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

$8,400,000

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.

7 Beds ⋅ 8 Baths ⋅ 73592560 MLS

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

54 Sargent Road, Brookline

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

$21,750,000

We are pleased to present the opportunity to acquire Beacon Fairbanks Manor, a 56-unit apartment community in one of Greater Boston’s most highly ranked and supply-constrained submarkets, Brookline, MA. Beacon Fairbanks Manor occupies a prime position on Beacon Street between Coolidge Corner and Washington Square, sitting directly on the MBTA Green Line Fairbanks Street stop. The property consists of 11 Studios, 30-One Bedroom, and 15-Two Bedroom units. The property provides durable in-place income underpinned by an irreplaceable location and strong tenant demographic, paired with a clear value-add business plan with significant upside. The property sits within a short commute of the 213-acre Longwood Medical Area; home to Brigham and Women’s Hospital, Boston Children’s Hospital, Beth Israel Deaconess Medical Center, and Dana Farber Cancer Institute. Additionally, Beacon Fairbanks Manor provides rapid transit to tenants who work in the major employment hubs of Boston, Cambridge, Brookline, and beyond. Nearby amenities are unmatched within Coolidge Corner and Washington Square, known for boutique dining, grocery options, retail, nightlife, and a strong sense of community that supports low turnover rates.

99 Beds ⋅ 115 Baths ⋅ 73592434 MLS

We are pleased to present the opportunity to acquire Beacon Fairbanks Manor, a 56-unit apartment community in one of Greater Boston’s most highly ranked and supply-constrained submarkets, Brookline, MA. Beacon Fairbanks Manor occupies a prime position on Beacon Street between Coolidge Corner and Washington Square, sitting directly on the MBTA Green Line Fairbanks Street stop. The property consists of 11 Studios, 30-One Bedroom, and 15-Two Bedroom units. The property provides durable in-place income underpinned by an irreplaceable location and strong tenant demographic, paired with a clear value-add business plan with significant upside. The property sits within a short commute of the 213-acre Longwood Medical Area; home to Brigham and Women’s Hospital, Boston Children’s Hospital, Beth Israel Deaconess Medical Center, and Dana Farber Cancer Institute. Additionally, Beacon Fairbanks Manor provides rapid transit to tenants who work in the major employment hubs of Boston, Cambridge, Brookline, and beyond. Nearby amenities are unmatched within Coolidge Corner and Washington Square, known for boutique dining, grocery options, retail, nightlife, and a strong sense of community that supports low turnover rates.

1539 Beacon Street, Brookline

Listing courtesy of Listing Agent: Kevin Benzinger from Listing Office: Boston Realty Advisors.

$34,000,000

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.

7 Beds ⋅ 16 Baths ⋅ 73590483 MLS

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

55 Singletree Rd, Brookline

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

$8,500

Victorian-Style Renovated Three-Level SINGLE-FAMILY HOME in BROOKLINE. Nestled in a serene neighborhood near Pierce Elementary School, Brookline High School & Brookline Village. Davis Ave is a scenic, tree-lined street in Brookline. Children’s playground across the field. Steps to the Green Line (T) stop with Direct Access to Longwood Medical & Downtown Boston. 6 Bedrooms + Home Office. 4 Full Bathrooms. Enter into a Grand Foyer with original natural woodwork & Hardwood Floors. Modern kitchen has GAS Cooking, Wolf Appliances & Chef quality Hood Vent. Quartz Countertops & Storage at very corner. Central A/C, Laundry in Unit & 2 Off-Street Parking Spaces. Second and third floors offer large bedrooms w/Custom Closets. Primary Bathroom is European inspired with a Walk-In Shower and Bain Ultra Soaking Tub. Natural light illuminates each room in the house and views of the Treelined Park create a Zen experience. Available for Immediate Occupancy. Water/Sewer included in the Rent. No pets, no smoking.

6 Beds ⋅ 4 Baths ⋅ 73589427 MLS

Victorian-Style Renovated Three-Level SINGLE-FAMILY HOME in BROOKLINE. Nestled in a serene neighborhood near Pierce Elementary School, Brookline High School & Brookline Village. Davis Ave is a scenic, tree-lined street in Brookline. Children’s playground across the field. Steps to the Green Line (T) stop with Direct Access to Longwood Medical & Downtown Boston. 6 Bedrooms + Home Office. 4 Full Bathrooms. Enter into a Grand Foyer with original natural woodwork & Hardwood Floors. Modern kitchen has GAS Cooking, Wolf Appliances & Chef quality Hood Vent. Quartz Countertops & Storage at very corner. Central A/C, Laundry in Unit & 2 Off-Street Parking Spaces. Second and third floors offer large bedrooms w/Custom Closets. Primary Bathroom is European inspired with a Walk-In Shower and Bain Ultra Soaking Tub. Natural light illuminates each room in the house and views of the Treelined Park create a Zen experience. Available for Immediate Occupancy. Water/Sewer included in the Rent. No pets, no smoking.

191 Davis Avenue, Brookline

Listing courtesy of Listing Agent: Collin Bray from Listing Office: Century 21 Cityside.

$2,350,000

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.

6 Beds ⋅ 4 Baths ⋅ 73587355 MLS

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

309 Buckminster Rd, Brookline

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

$3,999,000

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.

8 Beds ⋅ 4 Baths ⋅ 73586478 MLS

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

91 Verndale St, Brookline

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

$3,999,000

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.

8 Beds ⋅ 4 Baths ⋅ 73586477 MLS

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

91 Verndale St, Brookline

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

$2,399,900

Rare development opportunity at 101-103 University Road in the heart of Brookline's Washington Square. The town will allow a 3-family plus an ADU, giving builders and investors a flexible path to multiple units on an expansive lot of over 5,300 square feet. The standout advantage is timing; the property is already past the demo delay and utilities have been cut and capped, so your project can move forward immediately without the typical waiting period. Whether you envision a high-end multi-unit development, a custom build for yourself, or a significant residential transformation, this site offers the space and the framework to bring your vision to life. Skip the red tape and start building on one of the area's rarely available lots. Email or text me for details.

6 Beds ⋅ 4 Baths ⋅ 73586222 MLS

Rare development opportunity at 101-103 University Road in the heart of Brookline's Washington Square. The town will allow a 3-family plus an ADU, giving builders and investors a flexible path to multiple units on an expansive lot of over 5,300 square feet. The standout advantage is timing; the property is already past the demo delay and utilities have been cut and capped, so your project can move forward immediately without the typical waiting period. Whether you envision a high-end multi-unit development, a custom build for yourself, or a significant residential transformation, this site offers the space and the framework to bring your vision to life. Skip the red tape and start building on one of the area's rarely available lots. Email or text me for details.

101-103 University Rd, Brookline

Listing courtesy of Listing Agent: Eric Tam from Listing Office: Compass.

$35,000

Welcome to the Winslow House in Brookline. A grand co-living space offering 13 bedrooms, 11 bathrooms in total, comprising 9 luxurious suites with private bathrooms and 4 bedrooms sharing 2 common bathrooms. The main level boasts a spacious furnished living room seamlessly connected to a beautifully crafted kitchen and dining area. Featuring custom cabinetry, sleek quartz countertops, stainless steel appliances, dual refrigerators, two stoves, and ample dining space with a breakfast bar and banquet area. Convenient kitchenettes on each floor. Bedrooms are fully furnished with beds, dressers, desks, seating, and TVs. Enjoy the expansive wrap-around porch for alfresco dining and unwinding. Admire the grand staircase adorned with banquet seating. Laundry facilities in the basement. Off-street parking. All utilities and internet included. Property is fully furnished. Situated near Coolidge Corner Brookline, BU and Green Line (B) (C). Whole property leased or individual rooms; Dec/Jan availability.

13 Beds ⋅ 11 Baths ⋅ 73585655 MLS

Welcome to the Winslow House in Brookline. A grand co-living space offering 13 bedrooms, 11 bathrooms in total, comprising 9 luxurious suites with private bathrooms and 4 bedrooms sharing 2 common bathrooms. The main level boasts a spacious furnished living room seamlessly connected to a beautifully crafted kitchen and dining area. Featuring custom cabinetry, sleek quartz countertops, stainless steel appliances, dual refrigerators, two stoves, and ample dining space with a breakfast bar and banquet area. Convenient kitchenettes on each floor. Bedrooms are fully furnished with beds, dressers, desks, seating, and TVs. Enjoy the expansive wrap-around porch for alfresco dining and unwinding. Admire the grand staircase adorned with banquet seating. Laundry facilities in the basement. Off-street parking. All utilities and internet included. Property is fully furnished. Situated near Coolidge Corner Brookline, BU and Green Line (B) (C). Whole property leased or individual rooms; Dec/Jan availability.

44 Winslow Rd., Brookline

Listing courtesy of Listing Agent: Brandon Muroff from Listing Office: Brandon Muroff.

$1,950,000

You don't want to miss out on this investment opportunity Gem! Come check out this charming, lovely huge 3-family house in the heart of Chestnut Hill Brookline. The property features 3 units with over 4500 SF, with an unfished basement with new coin laundry. New Electrical with separate meters was updated. Unit 1 is a 3-bedroom 1 bathroom with, a washer and dryer in the unit. Unit 2 is a 4/5 bedroom 1 bathroom with a recently renovated kitchen and bathroom. Unit 3 is a 4-bedroom 1 bathroom that has hardwood flooring throughout. All units are leased till the end of August 2027. This property is a 5-minute walk to the Hayes school and Brookline Reservoir. This property has easy highway access and public transportation (60 bus C and D train). The property is a 10-minute drive to the Longwood medical area. This attractive multifamily opportunity allows investors to own a stable cash flow! This investment won't last!

11 Beds ⋅ 3 Baths ⋅ 73584003 MLS

You don't want to miss out on this investment opportunity Gem! Come check out this charming, lovely huge 3-family house in the heart of Chestnut Hill Brookline. The property features 3 units with over 4500 SF, with an unfished basement with new coin laundry. New Electrical with separate meters was updated. Unit 1 is a 3-bedroom 1 bathroom with, a washer and dryer in the unit. Unit 2 is a 4/5 bedroom 1 bathroom with a recently renovated kitchen and bathroom. Unit 3 is a 4-bedroom 1 bathroom that has hardwood flooring throughout. All units are leased till the end of August 2027. This property is a 5-minute walk to the Hayes school and Brookline Reservoir. This property has easy highway access and public transportation (60 bus C and D train). The property is a 10-minute drive to the Longwood medical area. This attractive multifamily opportunity allows investors to own a stable cash flow! This investment won't last!

753 Boylston St, Brookline

Listing courtesy of Listing Agent: Vena Priestly from Listing Office: Rise Signature Homes.

$3,490,000

On the market for the first time in more than 60 years, this three-family home in Coolidge Corner has only had two owners. Originally a single-family home, it now has three units with 8 bedrooms and 4.5 baths in total. It features high ceilings, hardwood floors throughout, a beautiful stone foundation, slate roof, and large windows with great natural light. Livable as is, and ready for its next chapter. Perfect for a developer, a condo conversion, or an end user who can bring their own vision. It includes a detached one-car garage, a large unfinished basement, and a private rear yard. The neighborhood is secluded, having only two entrances, yet it is ideally located between the B and C Green Line branches and just a few homes away from Coolidge Park. Sold as-is.

8 Beds ⋅ 5 Baths ⋅ 73582390 MLS

On the market for the first time in more than 60 years, this three-family home in Coolidge Corner has only had two owners. Originally a single-family home, it now has three units with 8 bedrooms and 4.5 baths in total. It features high ceilings, hardwood floors throughout, a beautiful stone foundation, slate roof, and large windows with great natural light. Livable as is, and ready for its next chapter. Perfect for a developer, a condo conversion, or an end user who can bring their own vision. It includes a detached one-car garage, a large unfinished basement, and a private rear yard. The neighborhood is secluded, having only two entrances, yet it is ideally located between the B and C Green Line branches and just a few homes away from Coolidge Park. Sold as-is.

36 Columbia St, Brookline

Listing courtesy of Listing Agent: Benjamin Ginsburg from Listing Office: Redfin Corp..

$4,250,000

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.

6 Beds ⋅ 7 Baths ⋅ 73580905 MLS

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

362 Tappan St, Brookline

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

$2,599,000

Exceptional 3 Family Opportunity in Chestnut Hill, Brookline !! Rare Available, Well Maintained residence offering 3 separate units : each unit features nice HW floors, 3 generous size bedrooms, 1.5 baths, good size living room and well appointed kitchen with dining areas, SS appliances, granite countertops. Hardwood floors all over the units. Generous basement storage provides additional convenience close space for each unit. A major highlight is the 5 off street PARKING SPACES a valuable amenity in Brookline. Property also benefits from LETTERS OF COMPLIANCE FOR ALL 3 UNITS !!! Ideally situated near Brookline Reservoir, Chestnut Hill shopping and dining, public transportation, Rt 9 and convenient access to Boston And surrounding communities. Compelling opportunity to own a versatile 3 Family property in on of Brookline's most sought after neighborhoods. Unit 2 now available for a new owner !!

9 Beds ⋅ 6 Baths ⋅ 73577697 MLS

Exceptional 3 Family Opportunity in Chestnut Hill, Brookline !! Rare Available, Well Maintained residence offering 3 separate units : each unit features nice HW floors, 3 generous size bedrooms, 1.5 baths, good size living room and well appointed kitchen with dining areas, SS appliances, granite countertops. Hardwood floors all over the units. Generous basement storage provides additional convenience close space for each unit. A major highlight is the 5 off street PARKING SPACES a valuable amenity in Brookline. Property also benefits from LETTERS OF COMPLIANCE FOR ALL 3 UNITS !!! Ideally situated near Brookline Reservoir, Chestnut Hill shopping and dining, public transportation, Rt 9 and convenient access to Boston And surrounding communities. Compelling opportunity to own a versatile 3 Family property in on of Brookline's most sought after neighborhoods. Unit 2 now available for a new owner !!

8 White Ave, Brookline

Listing courtesy of Listing Agent: The Caceda Team from Listing Office: Coldwell Banker Realty - Lynnfield.

$2,195,000

We are pleased to present 3 High Street Place, a three-unit multifamily property in Brookline Village, one block from Route 9 and a short walk from the Brookline Village Green Line station. Offered at $2,195,000, or $731,667per unit and $770.18 per square foot, the property brings a roster of all two-bedroom apartments to one of Greater Boston's most established rental submarkets.Built in 1910, the building holds three identical two-bedroom apartments set on a0.075-acre lot zoned M10. The building was gut-renovated in 2022 — all systems, windows, and the roof replaced — leaving a simple product to lease and manage. Heat is gas-fired hot water; tenants pay their own electricity on separate meters, while ownership carries water and sewer, and trash. The property draws on Brookline'sschools, transit, and proximity to the Longwood Medical Area.

6 Beds ⋅ 3 Baths ⋅ 73577192 MLS

We are pleased to present 3 High Street Place, a three-unit multifamily property in Brookline Village, one block from Route 9 and a short walk from the Brookline Village Green Line station. Offered at $2,195,000, or $731,667per unit and $770.18 per square foot, the property brings a roster of all two-bedroom apartments to one of Greater Boston's most established rental submarkets.Built in 1910, the building holds three identical two-bedroom apartments set on a0.075-acre lot zoned M10. The building was gut-renovated in 2022 — all systems, windows, and the roof replaced — leaving a simple product to lease and manage. Heat is gas-fired hot water; tenants pay their own electricity on separate meters, while ownership carries water and sewer, and trash. The property draws on Brookline'sschools, transit, and proximity to the Longwood Medical Area.

3 High Street Pl, Brookline

Listing courtesy of Listing Agent: Francis Saenz from Listing Office: Northeast Private Client Group.

$23,000,000

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.

6 Beds ⋅ 12 Baths ⋅ 73576839 MLS

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

381 Warren Street, Brookline

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

$3,100,000

Excellent opportunity to acquire a substantial three-family investment property in a desirable Brookline location with immediate access to Cleveland Circle and Coolidge Corner. Totaling 5,118 square feet, the building offers three exceptionally spacious apartments consisting of one two-bedroom and two three-bedroom units. Each residence features a generous and functional layout with large bedrooms, eat-in kitchens, hardwood floors, ample storage, and charming original details throughout. The property has been well maintained, including a new rubber roof installed in 2021, and offers off-street parking for multiple vehicles behind the building. Its location provides convenient access to public transportation, the Longwood Medical Area, Boston College, and the many shops, restaurants, and neighborhood amenities found throughout Brookline. All three apartments are occupied by long-term tenants on fixed leases extending through 2027, providing immediate and stable rental income for the next owner. A well-positioned Brookline multifamily asset offering substantial square footage, strong existing tenancy, and excellent long-term investment potential.

8 Beds ⋅ 3 Baths ⋅ 73575010 MLS

Excellent opportunity to acquire a substantial three-family investment property in a desirable Brookline location with immediate access to Cleveland Circle and Coolidge Corner. Totaling 5,118 square feet, the building offers three exceptionally spacious apartments consisting of one two-bedroom and two three-bedroom units. Each residence features a generous and functional layout with large bedrooms, eat-in kitchens, hardwood floors, ample storage, and charming original details throughout. The property has been well maintained, including a new rubber roof installed in 2021, and offers off-street parking for multiple vehicles behind the building. Its location provides convenient access to public transportation, the Longwood Medical Area, Boston College, and the many shops, restaurants, and neighborhood amenities found throughout Brookline. All three apartments are occupied by long-term tenants on fixed leases extending through 2027, providing immediate and stable rental income for the next owner. A well-positioned Brookline multifamily asset offering substantial square footage, strong existing tenancy, and excellent long-term investment potential.

3 Strathmore Rd, Brookline

Listing courtesy of Listing Agent: Matthew Foley from Listing Office: Fenway Property Advisors.

$6,995

Welcome to 48 Auburn Street, a spacious and charming 6-bedroom, 2.5-bath single-family home ideally located in the heart of Brookline. Available September 1st, this distinctive residence combines generous living space with beautiful original character and an exceptionally convenient location between Coolidge Corner and Brookline Village. Inside, you’ll find gorgeous original woodwork, hardwood floors, and two decorative fireplaces that add warmth and classic Brookline charm throughout the home. The kitchen is equipped with a dishwasher, and laundry is conveniently available in the home. Enjoy additional outdoor living space on the private deck, perfect for relaxing, dining, or entertaining. A private driveway with parking for two cars is also included—a major convenience in Brookline. With six bedrooms, 2.5 bathrooms, abundant character, and easy access to restaurants, shops, parks, public transportation, Coolidge Corner, and Brookline Village, 48 Auburn Street offers a rare opportunity to rent a full single-family home in one of Brookline’s most desirable locations.

6 Beds ⋅ 3 Baths ⋅ 73573387 MLS

Welcome to 48 Auburn Street, a spacious and charming 6-bedroom, 2.5-bath single-family home ideally located in the heart of Brookline. Available September 1st, this distinctive residence combines generous living space with beautiful original character and an exceptionally convenient location between Coolidge Corner and Brookline Village. Inside, you’ll find gorgeous original woodwork, hardwood floors, and two decorative fireplaces that add warmth and classic Brookline charm throughout the home. The kitchen is equipped with a dishwasher, and laundry is conveniently available in the home. Enjoy additional outdoor living space on the private deck, perfect for relaxing, dining, or entertaining. A private driveway with parking for two cars is also included—a major convenience in Brookline. With six bedrooms, 2.5 bathrooms, abundant character, and easy access to restaurants, shops, parks, public transportation, Coolidge Corner, and Brookline Village, 48 Auburn Street offers a rare opportunity to rent a full single-family home in one of Brookline’s most desirable locations.

48 Auburn Street Unit 48, Brookline

Listing courtesy of Listing Agent: Marika & Associates Group from Listing Office: Hammond Residential Real Estate.

$11,750,000

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.

6 Beds ⋅ 6 Baths ⋅ 73570794 MLS

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

71 Sears Road, Brookline

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

$10,000

This thoughtfully renovated carriage house is perfect for those who need to be near Longwood or close to the city. This luxurious single-family home can be delivered furnished or unfurnished. Located in the Longwood area, with many options for guests to visit or an in-law suite with exterior access, this home offers endless possibilities. Stroll to the T or enjoy access to local parks and conservation areas. Nearby hospitals or local universities make this an easy choice for professionals. Easy access to downtown and local amenities makes this the right choice for a discerning occupant. Comes with two off-street parking spaces and in-home laundry. Easy to show and will be delivered 9/1.

7 Beds ⋅ 4 Baths ⋅ 73563392 MLS

This thoughtfully renovated carriage house is perfect for those who need to be near Longwood or close to the city. This luxurious single-family home can be delivered furnished or unfurnished. Located in the Longwood area, with many options for guests to visit or an in-law suite with exterior access, this home offers endless possibilities. Stroll to the T or enjoy access to local parks and conservation areas. Nearby hospitals or local universities make this an easy choice for professionals. Easy access to downtown and local amenities makes this the right choice for a discerning occupant. Comes with two off-street parking spaces and in-home laundry. Easy to show and will be delivered 9/1.

259 Kent Unit R, Brookline

Listing courtesy of Listing Agent: Sarah Rodewald from Listing Office: SR Realty.

$2,500,000

Owner is Broker.

7 Beds ⋅ 4 Baths ⋅ 73562477 MLS

Owner is Broker.

103-105 Colbourne Crescent, Brookline

Listing courtesy of Listing Agent: Aaron Adler from Listing Office: Appraisals Unlimited, Inc.

$3,700,000

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.

6 Beds ⋅ 5 Baths ⋅ 73561991 MLS

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

292 Clinton Rd, Brookline

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

$2,999,000

RENOVATED Side-by-Side 2-FAMILY in BROOKLINE near Washington Square. Townhome Style Layouts, Each Unit has a Private Entry & Each home enjoys Private Outdoor Space, Deck + Terrace + Patio. Central A/C with separate HVAC. The Large DRIVEWAY, holds 3 Car Parking in Tandem. Strong Rental History! One Unit (#37) is 1600SF, 4BR/2BA, located on the right side and can be "Owner Occupied" while you collect rent ($7,225/month) next door at #39 w/Lease thru 8/31/27. That Penthouse Duplex is Spacious & Renovated with 5 Bedrooms/3 Bathrooms. The Living/Dining showcase a Wall of Windows, overlooking a Tree-lined Beaconsfield Road. Each room is Bright & Sundrenched across 3000 Square Feet. The finishes throughout are Condo-Quality! Beautiful Hardwood Floors, Central A/C, In-Unit Washer/Dryer. Entering the Kitchen, The Delighted Chef in YOU feels at home with a Gas Cooking & High-End Appliances like VIKING + SUB-ZERO. On the left side, #39 has generously-sized Bedrooms with a WOW Primary Suite --Walk in Closet--Primary Bathroom. Cherry Wood Cabinets surround a Double Vanity. The Cherry on Top? The Vanity has Custom Storage on ALL sides...Left | Right | Center...PRIME LOCATION with Access to Washington Square's Restaurants, Botique Shops and Star Market. Just minutes to the Beaconsfield Green Line (T) station, D Line + C Line. Only 10 min walk to Brookline High School or The Brookline Reservoir. Beaconsfield is a side street, making this an exceptional Investment Opportunity.

9 Beds ⋅ 5 Baths ⋅ 73561142 MLS

RENOVATED Side-by-Side 2-FAMILY in BROOKLINE near Washington Square. Townhome Style Layouts, Each Unit has a Private Entry & Each home enjoys Private Outdoor Space, Deck + Terrace + Patio. Central A/C with separate HVAC. The Large DRIVEWAY, holds 3 Car Parking in Tandem. Strong Rental History! One Unit (#37) is 1600SF, 4BR/2BA, located on the right side and can be "Owner Occupied" while you collect rent ($7,225/month) next door at #39 w/Lease thru 8/31/27. That Penthouse Duplex is Spacious & Renovated with 5 Bedrooms/3 Bathrooms. The Living/Dining showcase a Wall of Windows, overlooking a Tree-lined Beaconsfield Road. Each room is Bright & Sundrenched across 3000 Square Feet. The finishes throughout are Condo-Quality! Beautiful Hardwood Floors, Central A/C, In-Unit Washer/Dryer. Entering the Kitchen, The Delighted Chef in YOU feels at home with a Gas Cooking & High-End Appliances like VIKING + SUB-ZERO. On the left side, #39 has generously-sized Bedrooms with a WOW Primary Suite --Walk in Closet--Primary Bathroom. Cherry Wood Cabinets surround a Double Vanity. The Cherry on Top? The Vanity has Custom Storage on ALL sides...Left | Right | Center...PRIME LOCATION with Access to Washington Square's Restaurants, Botique Shops and Star Market. Just minutes to the Beaconsfield Green Line (T) station, D Line + C Line. Only 10 min walk to Brookline High School or The Brookline Reservoir. Beaconsfield is a side street, making this an exceptional Investment Opportunity.

37-39 Beaconsfield Road, Brookline

Listing courtesy of Listing Agent: Collin Bray from Listing Office: Century 21 Cityside.

$1,699,000

Investors, take note! Don't miss this exceptional opportunity to own a three-family property in one of Brookline's most sought-after locations. Situated near Brookline Village, this property is just a 12-minute walk to the Green Line, providing convenient access to Fenway, Downtown Boston, and beyond. The MBTA Route 60 bus to the Longwood Medical Area is just steps from the front door. Enjoy a highly walkable neighborhood with easy access to grocery stores, restaurants, parks, walking trails, and all the amenities that make Brookline such a desirable place to live.Add your own modern day updates, and with repairs, this classic property has the potential to truly shine! Large driveway accommodates multiple cars for easy off street parking.! Located in a community renowned for its exceptional schools, vibrant neighborhoods!

9 Beds ⋅ 4 Baths ⋅ 73559809 MLS

Investors, take note! Don't miss this exceptional opportunity to own a three-family property in one of Brookline's most sought-after locations. Situated near Brookline Village, this property is just a 12-minute walk to the Green Line, providing convenient access to Fenway, Downtown Boston, and beyond. The MBTA Route 60 bus to the Longwood Medical Area is just steps from the front door. Enjoy a highly walkable neighborhood with easy access to grocery stores, restaurants, parks, walking trails, and all the amenities that make Brookline such a desirable place to live.Add your own modern day updates, and with repairs, this classic property has the potential to truly shine! Large driveway accommodates multiple cars for easy off street parking.! Located in a community renowned for its exceptional schools, vibrant neighborhoods!

86 Chestnut St, Brookline

Listing courtesy of Listing Agent: Sarah McIntyre from Listing Office: Red Tree Real Estate.

$15,750,000

Rare opportunity to acquire a generational asset in the heart of Washington Sq., Brookline. Just a stone’s throw away from Beacon St. – 10-24 University Rd. is positioned alongside one of the most transit-oriented throughfares in/around Greater Boston, providing immediate MBTA access to major universities, like BU, Northeastern and Wentworth, the Longwood Medical Area and the many tech and engineering hubs in Kenmore Sq./Downtown Boston. Addressed as 10-12, 16-18 and 22-24 University Rd., the offering consists of three (3) 7-unit buildings and eleven (11) surface level parking spaces on contiguous parcels spanning 23,479 sq./ft. in cumulative lot size. Gross building area within the shells of all three buildings amounts to 57,928 sq./ft. but twenty-one (21) residential units comprise 35,512 sq./ft. of living space, with eighteen (18) 4-5 bedroom dwellings across the first, second and third levels and three (3) 1-2 bedroom dwellings on the garden levels. While substantial value-add potential can be achieved by preserving the current building designs, additional opportunities may also exist by tapping into unutilized space on the fourth floors/garden levels, rearranging floorplans and/or increasing the total unit count.

79 Beds ⋅ 31 Baths ⋅ 73554361 MLS

Rare opportunity to acquire a generational asset in the heart of Washington Sq., Brookline. Just a stone’s throw away from Beacon St. – 10-24 University Rd. is positioned alongside one of the most transit-oriented throughfares in/around Greater Boston, providing immediate MBTA access to major universities, like BU, Northeastern and Wentworth, the Longwood Medical Area and the many tech and engineering hubs in Kenmore Sq./Downtown Boston. Addressed as 10-12, 16-18 and 22-24 University Rd., the offering consists of three (3) 7-unit buildings and eleven (11) surface level parking spaces on contiguous parcels spanning 23,479 sq./ft. in cumulative lot size. Gross building area within the shells of all three buildings amounts to 57,928 sq./ft. but twenty-one (21) residential units comprise 35,512 sq./ft. of living space, with eighteen (18) 4-5 bedroom dwellings across the first, second and third levels and three (3) 1-2 bedroom dwellings on the garden levels. While substantial value-add potential can be achieved by preserving the current building designs, additional opportunities may also exist by tapping into unutilized space on the fourth floors/garden levels, rearranging floorplans and/or increasing the total unit count.

10-24 University Rd., Brookline

Listing courtesy of Listing Agent: Joe Danisch from Listing Office: Coelho Realty Group LLC.

$11,750,000

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

6 Beds ⋅ 9 Baths ⋅ 73536353 MLS

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

Sears Road, Brookline

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

$5,500,000

Rare development opportunity in the heart of Brookline's coveted Washington Square neighborhood. Situated on University Road, 97 and 101-103 University are comprised of two abutting multifamily lots totaling 12,219 SF (approximately 6,000 SF each), with the ability to build three residential units on each lot by right. 6 Units total. OR ZBA-approved plans for a 9 Unit Development... past demo stay. Developers, investors, and end-users alike will appreciate the flexibility to develop the parcels separately or explore combining the lots for a larger-scale project. This property is offering a rare chance to capitalize on one of Greater Boston's most desirable and supply-constrained residential markets. No representations made by seller; buyer to perform their own due diligence. Email or Text me for more details.

12 Beds ⋅ 8 Baths ⋅ 73534622 MLS

Rare development opportunity in the heart of Brookline's coveted Washington Square neighborhood. Situated on University Road, 97 and 101-103 University are comprised of two abutting multifamily lots totaling 12,219 SF (approximately 6,000 SF each), with the ability to build three residential units on each lot by right. 6 Units total. OR ZBA-approved plans for a 9 Unit Development... past demo stay. Developers, investors, and end-users alike will appreciate the flexibility to develop the parcels separately or explore combining the lots for a larger-scale project. This property is offering a rare chance to capitalize on one of Greater Boston's most desirable and supply-constrained residential markets. No representations made by seller; buyer to perform their own due diligence. Email or Text me for more details.

97-103 University Rd, Brookline

Listing courtesy of Listing Agent: Eric Tam from Listing Office: Compass.

$4,650,000

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

6 Beds ⋅ 7 Baths ⋅ 73532609 MLS

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

129 Rangeley Rd, Brookline

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

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