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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.

$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.

$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.

$16,000,000

This spectacular residence, set on 4.5 acres in the prestigious Brookline Estate area, has been renovated and is surrounded by private, scenic landscapes. The interior, distinguished by its grandeur and elegance, is adorned with intricate period details, beautiful woodwork, and bright spacious rooms. The grand 13 rooms include a double living room with picturesque views of the gorgeous, expansive grounds. There are 6 bedrooms, one of which is the luxurious primary suite. The meticulously designed grounds feature several unique amenities, including a stunning terrace patio expanding the length of the home, an in-ground swimming pool with fountain and whirlpool artfully integrated with a stone cliff, fully equipped cabana, koi pond, private tennis court, putting green, and magnificent hardscaping. The property also has a three-bedroom cottage and a two-bedroom unit above the free-standing garage. Near fine shops, restaurants, and Downtown Boston.

6 Beds ⋅ 8 Baths ⋅ 73480812 MLS

This spectacular residence, set on 4.5 acres in the prestigious Brookline Estate area, has been renovated and is surrounded by private, scenic landscapes. The interior, distinguished by its grandeur and elegance, is adorned with intricate period details, beautiful woodwork, and bright spacious rooms. The grand 13 rooms include a double living room with picturesque views of the gorgeous, expansive grounds. There are 6 bedrooms, one of which is the luxurious primary suite. The meticulously designed grounds feature several unique amenities, including a stunning terrace patio expanding the length of the home, an in-ground swimming pool with fountain and whirlpool artfully integrated with a stone cliff, fully equipped cabana, koi pond, private tennis court, putting green, and magnificent hardscaping. The property also has a three-bedroom cottage and a two-bedroom unit above the free-standing garage. Near fine shops, restaurants, and Downtown Boston.

63 Goddard Avenue, Brookline

Listing courtesy of Listing Agent: Debby Belt from Listing Office: Hammond Residential 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.

$14,850,000

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

6 Beds ⋅ 8 Baths ⋅ 73507123 MLS

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

280 Warren St, Brookline

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

$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.

$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.

$11,000,000

Encompassing just under two acres of wooded, private land, 39 Cottage Street presents an exceptional setting for a custom-built estate in one of Greater Boston's most sought-after communities. Nestled among mature trees and natural landscape, the property offers remarkable privacy and a sense of seclusion while remaining just minutes from Boston and Chestnut Hill's shopping, dining, golf courses, and premier schools. With a scale seldom found in Brookline, the site provides the flexibility to create a truly bespoke residence tailored to your vision. A rare offering where privacy, location, and possibility converge. This lot can also be divided into two buildable lots.

73543050 MLS

Encompassing just under two acres of wooded, private land, 39 Cottage Street presents an exceptional setting for a custom-built estate in one of Greater Boston's most sought-after communities. Nestled among mature trees and natural landscape, the property offers remarkable privacy and a sense of seclusion while remaining just minutes from Boston and Chestnut Hill's shopping, dining, golf courses, and premier schools. With a scale seldom found in Brookline, the site provides the flexibility to create a truly bespoke residence tailored to your vision. A rare offering where privacy, location, and possibility converge. This lot can also be divided into two buildable lots.

39 Cottage St, Brookline

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

$11,000,000

Encompassing just under two acres of wooded, private land, 39 Cottage Street presents an exceptional setting for a custom-built estate in one of Greater Boston's most sought-after communities. Nestled among mature trees and natural landscape, the property offers remarkable privacy and a sense of seclusion while remaining just minutes from Boston and Chestnut Hill's shopping, dining, golf courses, and premier schools. With a scale seldom found in Brookline, the site provides the flexibility to create a truly bespoke residence tailored to your vision. A rare offering where privacy, location, and possibility converge. This lot can also be divided into two buildable lots.

73538903 MLS

Encompassing just under two acres of wooded, private land, 39 Cottage Street presents an exceptional setting for a custom-built estate in one of Greater Boston's most sought-after communities. Nestled among mature trees and natural landscape, the property offers remarkable privacy and a sense of seclusion while remaining just minutes from Boston and Chestnut Hill's shopping, dining, golf courses, and premier schools. With a scale seldom found in Brookline, the site provides the flexibility to create a truly bespoke residence tailored to your vision. A rare offering where privacy, location, and possibility converge. This lot can also be divided into two buildable lots.

39 Cottage St, Brookline

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

$10,000,000

CFO - July 29th, 2026. 20 & 32 Kent Street in Brookline are being offered as a portfolio sale.

73483636 MLS

CFO - July 29th, 2026. 20 & 32 Kent Street in Brookline are being offered as a portfolio sale.

20 & 32 Kent Street, Brookline

Listing courtesy of Listing Agent: Jeremy Freid from Listing Office: 128 CRE.

$9,985,000

Set on .74 acres in one of Brookline’s most coveted neighborhoods, this newly constructed estate blends timeless architecture with exceptional modern design. With impeccably finished living spaces and full AV wiring, it offers 5 bedrooms, 6 full and 2 half baths, and a layout ideal for today’s lifestyle. The heart of the home is a showstopping chef’s kitchen with top-tier appliances, custom cabinetry, and a large island opening to sun-filled living and dining areas. A seamless indoor-outdoor flow connects to the private, flat tree-lined lot—perfect for entertaining or relaxation. Highlights include a luxurious primary suite with spa bath, generous secondary bedrooms, family room and a versatile finished lower level, attached 3-car garage with heated driveway, permitting for a pool. Built by a renowned local builder, this move-in-ready residence offers unmatched style, craftsmanship, and comfort in one of Brookline’s most desirable settings. Just bring your toothbrush!

5 Beds ⋅ 8 Baths ⋅ 73478330 MLS

Set on .74 acres in one of Brookline’s most coveted neighborhoods, this newly constructed estate blends timeless architecture with exceptional modern design. With impeccably finished living spaces and full AV wiring, it offers 5 bedrooms, 6 full and 2 half baths, and a layout ideal for today’s lifestyle. The heart of the home is a showstopping chef’s kitchen with top-tier appliances, custom cabinetry, and a large island opening to sun-filled living and dining areas. A seamless indoor-outdoor flow connects to the private, flat tree-lined lot—perfect for entertaining or relaxation. Highlights include a luxurious primary suite with spa bath, generous secondary bedrooms, family room and a versatile finished lower level, attached 3-car garage with heated driveway, permitting for a pool. Built by a renowned local builder, this move-in-ready residence offers unmatched style, craftsmanship, and comfort in one of Brookline’s most desirable settings. Just bring your toothbrush!

68 Clyde Street, Brookline

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

$8,995,000

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

7 Beds ⋅ 6 Baths ⋅ 73496969 MLS

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

39 Worthington Rd, Brookline

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

$8,995,000

Exquisite in every detail, this magnificent brick Georgian boasts modern style design, suitable for grand scale entertaining & comfortable family living. A large, elegant foyer w/sweeping staircase & venetian plaster walls, opens to an elegant living room w/fireplace. A sunroom, just off the foyer, offers spectacular views of the level, acre+ lot w/ frontage on Cramond Street. There is a majestic dining room w/acoustic padded walls & a handsome family room w/custom cabinetry. The fully renovated chef’s kitchen features a center island, butler’s pantry & dining nook—truly exceptional w/top-grade appliances. The 2nd level has a luxurious primary suite w/fireplace & spa-like bath. There are 3 additional bedrooms, 3 full baths, an office & a laundry room on this level. The 3rd floor offers 2 additional bedrooms & a full bath. The lower level has a large media room, gym room, full bath, 2nd laundry room, mudroom & access to the 2-car garage. Easy access to highways, schools & airport.

6 Beds ⋅ 7 Baths ⋅ 73479457 MLS

Exquisite in every detail, this magnificent brick Georgian boasts modern style design, suitable for grand scale entertaining & comfortable family living. A large, elegant foyer w/sweeping staircase & venetian plaster walls, opens to an elegant living room w/fireplace. A sunroom, just off the foyer, offers spectacular views of the level, acre+ lot w/ frontage on Cramond Street. There is a majestic dining room w/acoustic padded walls & a handsome family room w/custom cabinetry. The fully renovated chef’s kitchen features a center island, butler’s pantry & dining nook—truly exceptional w/top-grade appliances. The 2nd level has a luxurious primary suite w/fireplace & spa-like bath. There are 3 additional bedrooms, 3 full baths, an office & a laundry room on this level. The 3rd floor offers 2 additional bedrooms & a full bath. The lower level has a large media room, gym room, full bath, 2nd laundry room, mudroom & access to the 2-car garage. Easy access to highways, schools & airport.

188 Heath St, Brookline

Listing courtesy of Listing Agent: The Kennedy Lynch Team from Listing Office: Hammond Residential Real Estate.

$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.

$8,200,000

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

6 Beds ⋅ 9 Baths ⋅ 73526856 MLS

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

40 Singletree Rd, Brookline

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

$7,500,000

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

6 Beds ⋅ 8 Baths ⋅ 73487838 MLS

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

1 Chestnut Place, Brookline

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

$6,695,000

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

7 Beds ⋅ 9 Baths ⋅ 73486175 MLS

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

75 Goddard Avenue, Brookline

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

$6,450,000

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.

4 Beds ⋅ 4 Baths ⋅ 73508634 MLS

Unique opportunity to have your dream home built in the heart of Fisher Hill! 11,338 sf level lot with foundation and plans for a 4 bedroom, 3.5 bath classic brick colonial home with 4,825 square feet of space (on 3 levels) and a 2 car detached garage with shed. Gourmet kitchen opens to the den, dining and living room. First floor covered porch and terrace, perfect for al fresco dining. Exceptional location, close to Fisher Hill Park, Runkle School, public transportation, shopping, dining, an easy commute to Boston, Longwood medical area and Cambridge. Modifications to the plans subject to review and approval. Buyer to verify all information. Photos are renderings.Also available as a lot with foundation for $2,950,000.

9 Willard Road, Brookline

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

$6,400,000

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.

4 Beds ⋅ 5 Baths ⋅ 73500458 MLS

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

198 Clyde Street, Brookline

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

$5,990,000

Location, Location, Location! Exceptional two-unit mixed-use building in the heart of Brookline, featuring a NNN-leased commercial space occupied by a premier national restaurant operator with $2M+ buildout. The property includes a rare Brookline 1:00 AM full liquor license, elevator access for commercial deliveries, and expansive outdoor patio seating. The second floor offers a refined 3-bedroom, 1.5-bath residence with open living, dining area, in-unit laundry, and an extraordinary private roof terrace exceeding 1,000 SF. Unmatched setting just steps to the Green Line, Coolidge Corner, BU, Longwood Medical, H-Mart next door, and Boston’s most vibrant destinations.

3 Beds ⋅ 5 Baths ⋅ 73475133 MLS

Location, Location, Location! Exceptional two-unit mixed-use building in the heart of Brookline, featuring a NNN-leased commercial space occupied by a premier national restaurant operator with $2M+ buildout. The property includes a rare Brookline 1:00 AM full liquor license, elevator access for commercial deliveries, and expansive outdoor patio seating. The second floor offers a refined 3-bedroom, 1.5-bath residence with open living, dining area, in-unit laundry, and an extraordinary private roof terrace exceeding 1,000 SF. Unmatched setting just steps to the Green Line, Coolidge Corner, BU, Longwood Medical, H-Mart next door, and Boston’s most vibrant destinations.

1002 Beacon St, Brookline

Listing courtesy of Listing Agent: Michelle Chen from Listing Office: Coldwell Banker Realty - Cambridge.

$5,990,000

Location, Location, Location! Exceptional two-unit mixed-use building in the heart of Brookline, featuring a NNN-leased commercial space occupied by a premier national restaurant operator with $2M+ buildout. The property includes a rare Brookline 1:00 AM full liquor license, elevator access for commercial deliveries, and expansive outdoor patio seating. The second floor offers a refined 3-bedroom, 1.5-bath residence with open living, dining area, in-unit laundry, and an extraordinary private roof terrace exceeding 1,000 SF. Unmatched setting just steps to the Green Line, Coolidge Corner, BU, Longwood Medical, H-Mart next door, and Boston’s most vibrant destinations.

73474144 MLS

Location, Location, Location! Exceptional two-unit mixed-use building in the heart of Brookline, featuring a NNN-leased commercial space occupied by a premier national restaurant operator with $2M+ buildout. The property includes a rare Brookline 1:00 AM full liquor license, elevator access for commercial deliveries, and expansive outdoor patio seating. The second floor offers a refined 3-bedroom, 1.5-bath residence with open living, dining area, in-unit laundry, and an extraordinary private roof terrace exceeding 1,000 SF. Unmatched setting just steps to the Green Line, Coolidge Corner, BU, Longwood Medical, H-Mart next door, and Boston’s most vibrant destinations.

1002 Beacon St, Brookline

Listing courtesy of Listing Agent: Michelle Chen from Listing Office: Coldwell Banker Realty - Cambridge.

$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.

$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.

73534623 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.

$5,398,000

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

5 Beds ⋅ 5 Baths ⋅ 73592351 MLS

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

15 Catlin Road, Brookline

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

$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.

$4,795,000

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.

4 Beds ⋅ 5 Baths ⋅ 73520842 MLS

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

9 Singletree Rd, Brookline

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

$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.

$4,500,000

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

5 Beds ⋅ 6 Baths ⋅ 73572602 MLS

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

50 Sumner Road, Brookline

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

$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.

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