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Street View
$34,000,000
Monthly Est:$169,230
7 Beds
- 16 Baths
10 full baths + 6 half baths
19,138sqft
55 Singletree Rd, Chestnut Hill, MA 02467
$34,000,000
$169,230/moEst:
Get Pre-Approved
Single Family Residence
Built in 2015
$-- HOA
2.06 acres lot
$1,777/sq.ft
Description
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.
- Houzeo last checked: 3 minutes ago
- Listing updated: October 14, 2026 at 8:34 pm
- Listing Provided by: The Sarkis Team (617) 875-4950 | Douglas Elliman Real Estate - The Sarkis Team (781) 603-8702
- Source: MLS Property Information Network-MA | MLS#: 73590483

Property Details
Status
Active
Type
Single Family Residence
No. of Stories
-
County
City
Neighborhood
--
Year Built
2015
HOA Fees
-
Finished Area
19,138 sqft
Lot Size
2.06 acres lot
Basement Area
- sqft
MLS Name
MLS Property Information Network
MLS Number
73590483
MLS Status
New
Days on Market
2

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Location
Facts & Features
Rooms
Bedrooms & bathrooms
Bedrooms: 7
Bathrooms: 16
Interior
Cooling
Central Air
Appliances
Range, Oven, Dishwasher, Microwave, Refrigerator, Freezer, Washer, Dryer, Wine Refrigerator, Range Hood, Instant Hot Water
Sewer
Public Sewer
Exterior Features
Deck, Deck Roof, Patio, Covered Patio/deck, Balcony, Pool Inground Heated, Cabana, Tennis Court(s), Rain Gutters, Hot Tub/spa, Storage, Professional Landscaping, Sprinkler System, Decorative Lighting, Fenced Yard, City View(s), Garden, Guest House, Stone Wall
Interior Features
Sauna/steam/hot Tub, Wet Bar, Wired For Sound, Elevator
Heating
Central
Window Features
Insulated Windows
Construction
Year Built
Year Built: 2015
Home type
Single Family Residence
Architectural Style
Contemporary
Foundation Details
Concrete Perimeter
Roof
Rubber
Utilities & Energy
Parking Features
Attached, Heated Garage, Workshop In Garage, Garage Faces Side, Oversized, Off Street, Driveway
Water Source
Public, Private
Pool Features
Pool Inground Heated
Utilities
For Gas Range
Security Features
Security System
Electric
Generator
Basement
Full, Finished
Other Features
Community Features
Public Transportation, Shopping, Pool, Tennis Court(s), Park, Walk/jog Trails, Golf, Medical Facility, Laundromat, Bike Path, Conservation Area, Highway Access, House Of Worship, Private School, Public School, T Station, University
Disclosures
Property Was Built In 2 Phases Over Multiple Years. Year Built Is Approximate. Some Photos Virtually Enhanced For Marketing Purposes Only. Buyers To Preform All Due Diligence.
Patio And Porch Features
Deck, Deck Roof, Patio, Covered
Price History
| Date | Event | Price |
|---|---|---|
10/14/2026 Source: | Listed for Sale | $34,000,000 $1,777/sqft |
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Based on information provided to and compiled by MLS Property Information Network, Inc. covering through Oct 17, 2026, 12:15AM. 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 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 or leasing 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 or leasing. 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. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified. © 2026 MLS Property Information Network, Inc. All Rights Reserved.
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