27 Hemlock Hill Rd, Great Barrington, MA 01230 - Photo 1

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$3,995,000 Just Listed

For Sale
Active
Single Family
4 Beds
4 Full Baths
1 Partial Bath
5,683 Sq. Ft.
5.07 Acres
2 Car Garage
Updated 2 days ago

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Property Description

Beautifully sited to capture light and long-range views, this architect-designed residence offers timeless elegance within a serene natural setting. Bright, sophisticated interiors open seamlessly to a screened porch and stone terraces overlooking the pool and manicured grounds. Generous proportions and refined architectural details define the living spaces, complemented by a beautifully reimagined library/office, dining, living media/den and kitchen. First-floor primary suite serves as a private retreat, while additional en-suite bedrooms provide comfort and discretion for guests. An upper-level loft (w/ elevator)offers space for gym, studio, or media. A rare offering of privacy, design, and distinction in the Berkshires.

Full Property Details

Full Property Details for 27 Hemlock Hill Rd

General

Price: $3,995,000
Taxes: $38,984 (2025)
Status: Active
Type: Single Family
Source: 1109
MLS ID: 249407
Updated: 5/5/2026
Added to Site: 3 day(s) ago

Interior

Number of Rooms: 10
Interior Features: Backup Generator, Cable Available, Cathedral Ceilings, Central Vacuum, Granite Counter, Interior Balcony, Jet Tub, Marble Counter, Radon Mitigation System, Vaulted Ceilings, Walk-In Closet(s)
Appliances: Cooktop, Dishwasher, Dryer, Freezer, Microwave, Range, Range Hood, Refrigerator, Washer
Flooring: Ceramic Tile, Marble, Wood

Rooms

Bathrooms

Total Bathrooms: 5
Full Bathrooms: 4
Half Bathrooms: 1

Bedrooms

Total Bedrooms: 4

Additional Information

Pool: Yes

Exterior

Exterior Features: Lighting, Trash Private, Privacy, Pool - In Ground, Deciduous Shade Trees, Mature Landscaping, Fenced Yard, Landscaped, 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

Location

Area: South Registry

Heating & Cooling

Heating Type: Oil, Boiler, Forced Air

Utilities

Sewer: Private Sewer
Water: Well
Well: Yes

Structural Information

Architectural Style: Contemporary
Roof: Asphalt Shingles
Square Feet: 5,683
Year Built: 2006
Year Built Source: Assessor

Lot Features

Lot Size (Acres): 5.07
Lot Size (Sq. Ft.): 220,849
Lot Dimensions: 220849
Zoning: Residential

Green Features

Energy Efficient: Doors, Windows

Financial Considerations

Tax Amount: $38,984
Tax Year: 2025

Disclosures and Reports

Property ID: GREA M:032.A B:0061 L:0051.0

Listed by William Raveis - Berkshire, Claire Naylor Pollart

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Listing agent

— 27 Hemlock Hill Rd —

Claire Naylor Pollart

William Raveis - Berkshire

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Schools

Schools serving 27 Hemlock Hill Rd

School District:Berkshire Hills School District

Name	Grades	Distance
W.E.B. Du Bois Regional Middle School 313 Monument Valley Road, Great Barrington, MA 01230	5-8	2.7 mi
Muddy Brook Regional Elementary School 318 Monument Valley Road, Great Barrington, MA 01230	PK-4	2.8 mi
Monument Mt Regional High School 600 Stockbridge Road, Great Barrington, MA 01230	9-12	3 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 27 Hemlock Hill Rd Get Price Alerts and Save Property

Date

Details

Price

Change

Source

5/05/2026

Listed

$3,995,000

47.63%

MLS

4/26/2022

Sold

$2,706,000

—

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 27 Hemlock Hill Rd

Year

Property Taxes

Change

Tax Assessment

Change

2025

$38,984

9%

$2,827,000

10%

2024

$35,722

9%

$2,571,800

11%

2023

$32,676

7%

$2,322,400

13%

2022

$30,445

4%

$2,048,800

10%

2019

$29,315

7%

$1,864,800

2%

2018

$27,413

17%

$1,830,000

14%

2017

$23,397

3%

$1,602,500

1%

2016

$22,664

4%

$1,586,000

—

2015

$21,760

5%

$1,586,000

4%

2014

$20,646

—

$1,522,600

—

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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Estimate the Cost for 27 Hemlock Hill Rd

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27 Hemlock Hill Rd, Great Barrington, MA 01230 (MLS# 249407) is a Single Family property with 4 bedrooms, 4 full bathrooms and 1 partial bathroom. 27 Hemlock Hill Rd is currently listed for $3,995,000 and was received on May 05, 2026. Want to learn more about 27 Hemlock Hill Rd? Do you have questions about finding other Single Family real estate for sale in Great Barrington? You can browse all Great Barrington real estate or contact a Coldwell Banker agent to request more information.

27 Hemlock Hill Rd Great Barrington, MA 01230