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73 Chestnut Street Weston — Photo 1 of 42

73 Chestnut Street Weston — Photo 1 of 42

$9,450,000

Investment Analysis — 73 Chestnut Street

Weston, MA 02493

Based on HUD Small Area Fair Market Rent for Boston-Cambridge-Quincy, MA-NH HUD Metro FMR Area, a 7-bedroom in 02493 carries an estimated $4,010/mo in gross rent — about a -0.32% cap rate and $-30,378/yr in estimated NOI at the $9,450,000 list price. Adjust every assumption in the calculator below.

View Standard Listing

Beds

7

Baths

10

SqFt

12,461

Style

Single Family

Built

1952

Magnificent residence sited on 2.78 private and pristine acres in one of Weston’s most coveted locations. Completely renovated with the highest level of finishes offering every modern amenity. This exceptional home offers estate-like living designed equally for comfortable family life and sophisticated entertaining. The modern designer kitchen anchors the center of the home and flows seamlessly into the sumptuous fireplaced family room with access to private deck overlooking the pool and grounds and spacious screened porch, creating an inviting open floor plan. The formal dining room enhanced by a butler’s pantry is complemented by a well-proportioned formal living. Multiple home offices, a generous mudroom, dog-washing room and a large gym are just a few of the exceptional features this home offers. This home offers two luxurious primary suite options, one on each of first and seconds levels providing exceptional flexibility. All bedrooms are generously sized and feature ensuite baths. The lower level provides dedicated play, craft and billiard spaces along with ample storage. A sleek and private two-bedroom accessory dwelling with separate entrance and two-car garage offers additional accommodations. Resort-like grounds are enhanced with a beautiful pool, well equipped cabana, expansive patios, and private tennis court, creating an extraordinary setting for year-round living and entertaining. The incomparable residence provides the ultimate in private living while offering easy access to Boston and Weston’s renowned schools.

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 12,461 sq ft principal dwelling). Lot size: 120,984 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.

Property Details

Financials

Original Price$9,450,000
Annual Taxes$66,949

Parking

Garage5
Off-Street20

Interior Specifications

Total Rooms21
Fireplaces5
FlooringTile, Hardwood, Flooring - Hardwood
BasementFinished, Interior Entry

Climate & Utilities

HeatingForced Air, Fireplace
CoolingCentral Air
WaterPublic
SewerPrivate Sewer

Building & Exterior

ConstructionFrame
RoofShingle
FoundationConcrete Perimeter
ZoningSFR

Property & Lot

Acres2.78
SqFt Lot120,984
Lot FeaturesGentle Sloping

Amenities & Appliances

Gas Water Heater • Oven • Dishwasher • Microwave • Range • Refrigerator • Washer • Dryer • Wine Refrigerator • Range Hood

Neighborhood

Shopping • Pool • Tennis Court(s) • Park • Walk/Jog Trails • Bike Path

Geography

Floorplan Breakdown

Structural Layout

Second
Primary BedroomBedroom 2Bedroom 3Bedroom 4Bathroom 3
First
Living RoomDining RoomOfficeFamily RoomBedroom 5Bathroom 1Bathroom 2
Main,First
Kitchen
Living Room
Lvl First

Coffered Ceiling(s), Flooring - Hardwood, Recessed Lighting, Lighting - Sconce, Lighting - Pendant, Decorative Molding

Dining Room
Lvl First

Flooring - Hardwood, Recessed Lighting, Lighting - Pendant, Decorative Molding

Kitchen
Lvl Main,First

Flooring - Hardwood, Dining Area, Pantry, Countertops - Upgraded, Kitchen Island, Wet Bar, Breakfast Bar / Nook, Cabinets - Upgraded, Exterior Access, Open Floorplan, Recessed Lighting, Remodeled, Second Dishwasher, Stainless Steel Appliances, Lighting - Pendant

Office
Lvl First

Fireplace, Flooring - Hardwood, Recessed Lighting, Decorative Molding

Family Room
Lvl First

Coffered Ceiling(s), Closet/Cabinets - Custom Built, Flooring - Hardwood, Balcony - Exterior, Wet Bar, Exterior Access, Open Floorplan, Recessed Lighting, Slider, Lighting - Pendant, Decorative Molding

Primary Bedroom
Lvl Second

Bathroom - Full, Bathroom - Double Vanity/Sink, Closet/Cabinets - Custom Built, Flooring - Hardwood, Dressing Room, Recessed Lighting, Lighting - Sconce, Lighting - Pendant, Decorative Molding, Window Seat

Bedroom 2
Lvl Second
Bedroom 3
Lvl Second

Bathroom - Full, Closet/Cabinets - Custom Built, Flooring - Hardwood, Recessed Lighting, Lighting - Sconce, Lighting - Pendant, Decorative Molding

Bedroom 4
Lvl Second

Bathroom - Full, Closet/Cabinets - Custom Built, Flooring - Hardwood, Recessed Lighting, Lighting - Sconce, Lighting - Pendant, Decorative Molding

Bedroom 5
Lvl First

Bathroom - Full, Bathroom - Double Vanity/Sink, Fireplace, Closet/Cabinets - Custom Built, Flooring - Hardwood, Flooring - Stone/Ceramic Tile

Bathroom 1
Lvl First

Bathroom - Half, Flooring - Hardwood, Lighting - Sconce, Decorative Molding

Bathroom 2
Lvl First

Bathroom - Half

Bathroom 3
Lvl Second

Bathroom - Full, Flooring - Stone/Ceramic Tile

Property History

Listed
$9,450,000

Sep 15, 2026

MLS® 73577074

Sold
$4,300

Jul 20, 2025

MLS® 73403189

Listed
$4,500

Jul 11, 2025

MLS® 73403189

Listing Provided By

Listing Agent: Deena Powell

Listing Office: Advisors Living - Weston

MLS® Number: 73577074