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202 Days on market

1 Chestnut Place Brookline — Photo 1 of 26

$7,500,000

Investment Analysis — 1 Chestnut Place

Brookline, MA 02445

Based on HUD Small Area Fair Market Rent for Boston-Cambridge-Quincy, MA-NH HUD Metro FMR Area, a 6-bedroom in 02445 carries an estimated $5,240/mo in gross rent — about a -0.26% cap rate and $-19,722/yr in estimated NOI at the $7,500,000 list price. Adjust every assumption in the calculator below.

View Standard Listing

Beds

Baths

SqFt

7,780

Style

Single Family

Built

2006

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!

ADU Potential

Massachusetts allows one accessory dwelling unit by right in single-family zoning districts statewide (M.G.L. c. 40A §3; 760 CMR 71.00, effective Feb 2025). Estimated maximum ADU size for this property: 900 sq ft (the lesser of 900 sq ft or half the 7,780 sq ft principal dwelling). Lot size: 24,829 sq ft.

Based on listing data, which indicates the property type — not the zoning district. Local dimensional, septic (Title 5), and historic-district requirements still apply. Not legal advice — verify with the municipality.

Estimates — not financial advice

These figures are illustrative estimates for informational purposes only — not an appraisal, valuation, or guarantee of rent, income, or returns, and not financial, tax, or investment advice. Rent is either the figure reported on the MLS listing — in-place rent that may differ from market and is not verified against the actual leases — or, where the listing reports none, an estimate from HUD Small Area Fair Market Rents, a government benchmark that may differ from actual market rent. Each figure is labelled with its source. Cap rate, NOI, and returns depend on the assumptions shown, which you can change. MLS and other third-party data may be inaccurate or out of date. Verify all figures independently and consult your own financial, tax, and legal advisors before making any investment decision.

Financials

Original Price$7,500,000

Annual Taxes$67,511

Parking

Garage3

Off-Street13

Interior Specifications

Total Rooms25

Fireplaces4

FlooringWood

BasementFull, Finished, Walk-Out Access

Climate & Utilities

HeatingForced Air, Radiant, Humidity Control, Natural Gas, Hydro Air

CoolingCentral Air

WaterPublic

SewerPublic Sewer

Building & Exterior

ConstructionFrame

RoofShingle

FoundationConcrete Perimeter

ZoningS25

Property & Lot

Acres0.57

SqFt Lot24,829

Lot FeaturesWooded, Level

Amenities & Appliances

Gas Water Heater • Water Heater • Range • Oven • Dishwasher • Disposal • Microwave • Refrigerator • Freezer • Washer • Dryer • Wine Refrigerator • Vacuum System • Range Hood • Water Softener • Plumbed For Ice Maker