5 Deer Hill Rd, West Stockbridge, MA 01266 - Photo 1

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$4,975,000 Just Listed

For Sale
Active
Single Family
3 Beds
3 Full Baths
1 Partial Bath
4,359 Sq. Ft.
10.73 Acres
2 Car Garage
Updated 1 day ago

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Property Description

Perched to capture sweeping vistas, this contemporary architectural masterpiece seamlessly balances the demands of a world-class art collection with an immersive natural experience. The residence is brilliantly composed of three intersecting bars: a single-room-deep main volume that captures the views, a service wing and a perpendicular upper level that hovers to create a sheltered dining terrace below. Guided by museum-quality principles, long stretches of UV-protected wall space give way to precisely framed vistas. Board-formed concrete walls mitigate winter winds, while the exterior is clad in enduring, low-maintenance Vermont slate. Embracing sustainable luxury, the three-bedroom, two-study home features triple-glazed windows, super-insulated envelopes, and geothermal climate control.

Full Property Details

Full Property Details for 5 Deer Hill Rd

General

Price: $4,975,000
Taxes: $14,043 (2025)
Status: Active
Type: Single Family
Source: 1109
MLS ID: 250459
Updated: 8/10/2026
Added to Site: 6 day(s) ago

Interior

Number of Rooms: 7
Interior Features: Alarm System, Backup Generator, Cable Available, Cathedral Ceilings, Fireplace (s), Skylight(s)
Appliances: Built-In Electric Oven, Cooktop, Dishwasher, Dryer, Microwave, Refrigerator, Washer
Flooring: Concrete, Wood

Rooms

Bathrooms

Total Bathrooms: 4
Full Bathrooms: 3
Half Bathrooms: 1

Bedrooms

Total Bedrooms: 3

Exterior

Exterior Features: Outbuilding, Patio

Parking

Attached garage: Yes
Garage Spaces: 2
Parking Features: Garaged & Off-Street
Other Parking Type: Garaged & Off-Street
Garage Description: Attached, Auto Opener, Insulated, Oversized

Location

Area: South Registry

Heating & Cooling

Heating Type: Propane, Electric, Forced Air

Utilities

Sewer: Private Sewer
Water: Well
Well: Yes

Structural Information

Architectural Style: Contemporary
Roof: Membrane
Windows: Insulated Windows
Square Feet: 4,359
Year Built: 2009
Year Built Source: Assessor

Lot Features

Lot Size (Acres): 10.73
Lot Size (Sq. Ft.): 467,399
Lot Dimensions: 467399
Zoning: Residential

Financial Considerations

Tax Amount: $14,043
Tax Year: 2025

Disclosures and Reports

Property ID: WSTO M:401 B:00000 L:0141

Listed by William Pitt Sotheby's - Gt Barrington, Leslie G Chesloff

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Listing agent

— 5 Deer Hill Rd —

Leslie G Chesloff

William Pitt Sotheby's - Gt Barrington

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NMLS#: 1598647

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Schools

Schools serving 5 Deer Hill Rd

School District:Berkshire Hills School District

Name	Grades	Distance
Muddy Brook Regional Elementary School 318 Monument Valley Road, Great Barrington, MA 01230	PK-4	7.2 mi
W.E.B. Du Bois Regional Middle School 313 Monument Valley Road, Great Barrington, MA 01230	5-8	7.3 mi
Monument Mt Regional High School 600 Stockbridge Road, Great Barrington, MA 01230	9-12	7 mi

Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 5 Deer Hill Rd Get Price Alerts and Save Property

Date

Details

Price

Change

Source

8/06/2026

Listed

$4,975,000

437.84%

MLS

12/02/2008

Sold

$925,000

—

Public Record

Get Price Alerts and Save Property

Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History

Tax History for 5 Deer Hill Rd

Year

Property Taxes

Change

Tax Assessment

Change

2025

$14,043

2%

$1,459,800

1%

2024

$13,803

6%

$1,440,800

14%

2023

$12,988

7%

$1,259,700

30%

2022

$12,161

1%

$968,200

11%

2021

$12,096

6%

$869,600

—

2020

$11,409

7%

$869,600

-1%

2019

$10,663

—

$879,100

—

2018

$10,663

-3%

$879,100

—

2017

$10,971

1%

$879,100

—

2016

$10,839

4%

$879,100

—

2015

$10,409

4%

$879,100

-3%

2014

$10,030

—

$902,000

—

View All

Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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5 Deer Hill Rd, West Stockbridge, MA 01266 (MLS# 250459) is a Single Family property with 3 bedrooms, 3 full bathrooms and 1 partial bathroom. 5 Deer Hill Rd is currently listed for $4,975,000 and was received on August 06, 2026. Want to learn more about 5 Deer Hill Rd? Do you have questions about finding other Single Family real estate for sale in West Stockbridge? You can browse all West Stockbridge real estate or contact a Coldwell Banker agent to request more information.

5 Deer Hill Rd West Stockbridge, MA 01266