Refine Search
Map
Sort by
55 Singletree Rd, Brookline
$34,000,000
7 Beds ⋅ 16 Baths ⋅ 73590483 MLS
There are exceptional homes, and then there are properties conceived on an entirely different scale. 55 Singletree is the latter. Perched atop a secluded hill on more than two private acres in Brookline, adjacent to the reservoir, this extraordinary estate offers a rare sense of privacy and tranquility just minutes from Boston. Its elevated position and naturally sheltered setting create remarkable seclusion, with no neighboring homes overlooking the pool or private outdoor spaces. Years of vision, craftsmanship, and investment have been brought to life through an extensive two-phase construction project by Thoughtforms, one of New England’s most respected custom home builders. The result is not simply a residence, but a world unto itself—an estate with the scale and experience of a private resort. The property's commanding elevation captures views toward the Boston skyline, culminating at a rooftop terrace overlooking the city. Across the grounds, architecture and landscape have been conceived as one experience. Water features introduce movement and serenity, expansive outdoor spaces invite both gathering and escape, and a private tennis and sports court creates a level of recreation rarely found so close to the city. Inside, monumental scale meets intimate refinement, with exceptional materials, custom craftsmanship, and thoughtfully designed spaces equally suited for grand entertaining and everyday family life. An estate of this scale, caliber, and extraordinary privacy would be exceptionally difficult to replicate today. 55 Singletree represents a singular opportunity: a secluded residential sanctuary offering remarkable sophistication, recreation, and proximity to Boston.

55 Singletree Rd, Brookline

Listing courtesy of Listing Agent: The Sarkis Team from Listing Office: Douglas Elliman Real Estate - The Sarkis Team.
185 Warren Street, Brookline
$3,095,000
5 Beds ⋅ 3 Baths ⋅ 73570606 MLS
Set on .92AC in Brookline’s Estate area, this 5BD, 3BA home was ahead of its time. Built in 1850 as the carriage barn of the Old Greenhill Estate, it was converted to a single-family and extensively reimagined with open living spaces, expansive glass, and a strong connection to the landscape. 2,834SF home enjoys southwest light throughout, with long sight lines to the outdoors & rooms that feel distinct yet flow naturally together. Oversized windows & glass doors open to backyard. Kitchen connects to the dining area w/ fireplace, while a family room with built-ins & a vaulted living room with 2nd fireplace offer flexible gathering spaces. 2 main-level bedrooms and a full bath add versatility. 2nd floor offers primary suite w/ treetop views and en-suite bath. 2 add’l bedrooms, full bath, and laundry complete 2nd floor. LL w/ mudroom, storage, & access to 2-car garage. Outside, mature trees, open lawns, seasonal gardens, and privacy create a rare setting just minutes from Boston.

185 Warren Street, Brookline

Listing courtesy of Listing Agent: Hilary Maddox Team from Listing Office: Compass.
365 Newton St, Brookline
$2,399,000
4 Beds ⋅ 3 Baths ⋅ 73547641 MLS
Prepare to be impressed by this beautifully renovated 4 Bed 3 Bath mid-century modern ranch in Chestnut Hill Brookline on the edge of the golf course! Set on over a half acre of beautiful landscaping surrounding the flat back yard lead to the golf course. Breathtaking renovations highlight modern living with soaring exposed beam ceilings, a dramatic living room with a wood-burning fireplace, and a wall of windows overlooking the screened porch, deck, and tranquil Japanese rock garden. The renovated kitchen features sleek cabinetry, updated countertops, appliances, a peninsula, pantry, and eat-in area. The main level offers three spacious bedrooms, including a large primary suite, while the finished walkout lower level includes a great room with kitchenette, fourth bedroom, full bath, studio, bonus room, patio access, and abundant storage. Perfect location with quick access to 9 & I-93 and a quick hop to local restaurants, shopping, Wegman's, and much more!

365 Newton St, Brookline

Listing courtesy of Listing Agent: Rose Hall from Listing Office: Blue Ocean Realty, LLC.
9 Singletree Rd, Brookline
$4,795,000
4 Beds ⋅ 5 Baths ⋅ 73520842 MLS
Nestled on a private 0.92-acre lot in the prestigious Chestnut Hill neighborhood, this exceptional custom-designed Mid-Century Modern ranch, inspired by the timeless architecture of Frank Lloyd Wright, offers a rare blend of sophistication, privacy, and seamless indoor-outdoor living. Thoughtfully designed with gracious proportions and walls of glass, the home is filled with natural light and overlooks beautifully landscaped grounds. A spectacular four-season breakfast room with four skylights complements the chef’s kitchen featuring top-of-the-line appliances, three ovens, two dishwashers, and custom cabinetry. The luxurious primary suite serves as a private sanctuary with dual showers and vanities, smart toilets, separate dressing areas, a soaking tub, and an attached office/library. The versatile lower level with separate entrance offers excellent potential for an in-law suite. Sliding glass doors line the rear of the home, opening to a serene outdoor retreat with an elegant patio and heated pool. Superb Chestnut Hill location with easy access to Boston, shopping, dining and Medical Centers.

9 Singletree Rd, Brookline

Listing courtesy of Listing Agent: Deborah M. Gordon from Listing Office: Coldwell Banker Realty - Brookline.
90 Columbia, Brookline
$3,495,000
5 Beds ⋅ 5 Baths ⋅ 73516646 MLS
Spectacular single-family alternative. This side-by-side Contemporary Luxury townhouse, newly constructed in 2017, features all the luxury you would expect. Sprawling living room and dining. The eat-in kitchen has custom cabinetry, Thermador appliances, and marble countertops. The kitchen has direct access to the large private/exclusive backyard, which spans two levels. There is a large patio and garden. There are 5 bedrooms and 4.5 baths. Large Primary has cathedral ceilings and an ensuite, featuring a double shower, double vanity, soaking tub, and radiant floor heating. Adjoining the primary is a large family/sitting room with sliders to the patio overlooking the back garden. There is a finished lower level with a large family room and a large bedroom, both with glass sliders for direct outdoor access. There is a convenient kitchenette as well. Playground directly across. Minutes to school, shopping, restaurants, and T. Convenient to Longwood Medical and Boston. 92 Walk Score.

90 Columbia, Brookline

Listing courtesy of Listing Agent: Sheila White from Listing Office: Compass.
331 Heath Street, Brookline
$3,750,000
3 Beds ⋅ 4 Baths ⋅ 73481377 MLS
Location, Location, Location! 41,000+ square feet of land! Great opportunity to live in this unique contemporary home, add on or build your dream home on this site! The current home features 4 levels of living space with windows galore, many opening to patios, decks or balconies. 3 ensuite-bedrooms, 3 full and 1 half bath. The home offers 3 fireplaces adding warmth and a comforting glow. The kitchen is the heart of the home with generous center island, walls of glass and windowed alcove for dining as well as a spacious desk area. There is a large home office, that makes working from home a pleasure. The office could double as a 4th bedroom. Cool upper level loft serves as a meditation space with fireplace and balcony! Great walls for art and the hallways are truly galleries. Such fabulous spaces inside and out for entertaining. Updated systems. Lovely grounds. Spacious 2-car garage with ample storage.

331 Heath Street, Brookline

Listing courtesy of Listing Agent: Bobby Morgenstern from Listing Office: Gibson Sotheby's International Realty.

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

How much is your home worth?

Get instant property value now!