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$1,199,000 -$800,000 (-40.02%) Price Reduced

  • For Sale
  • Active
  • Single Family
  • 6 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 4,188 Sq. Ft.
  • 2.35 Acres
  • 1 Car Garage
  • Updated 1 hour ago
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Originally built with classic 19th century detail, this 6 bedroom, 3.5 bath Colonial/Victorian has been thoughtfully expanded and renovated, carefully embellishing its original character with today's sought-after conveniences. Elegantly spacious rooms with high ceilings and tall windows lead to the well-designed kitchen, where you'll find 2 copper sinks, Wolf double ovens, pot filler, warming drawer, built-in Miele coffee maker, and even a dumb waiter! In addition, a large sunroom was added, with radiant floor heat for year-round enjoyment. Other modern upgrades include a sophisticated central A/C system, back-up generator, and water filtration system. Most recently a gorgeous, heated in-ground pool was installed on your private 2.35 acres. Historically named ''Hilltop,'' this gracious home is perched on a knoll overlooking the quaint village of West Stockbridge with its intriguing shops, cafes, restaurants and convenient deli/grocery store. Walk to Card Lake. And there's an extra bonus; town water, and town sewer.

Full Property Details for 21 Stockbridge Rd

General

  • Price: $1,199,000
  • Taxes: $7,685 (2025)
  • Status: Active
  • Type: Single Family
  • Source: 1109
  • MLS ID: 249230
  • Updated: Today (4/20/2026)
  • Added to Site: Today

Interior

  • Number of Rooms: 13
  • Interior Features: Alarm System, Backup Generator, Bay/Bow Window, Cable Available, Fireplace (s), Granite Counter, Radiant Heat, Sun Room
  • Appliances: Built-In Electric Oven, Cooktop, Dishwasher, Dryer, Microwave, Range Hood, Refrigerator, Washer
  • Flooring: Ceramic Tile, Wood

Rooms

Bathrooms

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

Bedrooms

  • Total Bedrooms: 6

Additional Information

  • Pool: Yes

Exterior

  • Exterior Features: Privacy, Pool - In Ground, Porch, Deck, Fenced-Partially

Parking

  • Attached garage: Yes
  • Garage Spaces: 1
  • Parking Features: Off Street
  • Other Parking Type: Off Street
  • Garage Description: Attached, Auto Opener, Heated, Oversized

Location

  • Area: South Registry

Heating & Cooling

  • Heating Type: Oil

Utilities

  • Sewer: Public Sewer
  • Water: Public

Structural Information

  • Architectural Style: Colonial
  • Roof: Asphalt Shingles
  • Square Feet: 4,188
  • Year Built: 1800
  • Year Built Source: Assessor

Lot Features

  • Lot Size (Acres): 2.35
  • Lot Size (Sq. Ft.): 102,366
  • Lot Dimensions: Irregular
  • Zoning: Residential

Financial Considerations

  • Tax Amount: $7,685
  • Tax Year: 2025

Disclosures and Reports

  • Property ID: WSTO M:105 B:00000 L:0003

Listed by Stone House Properties, Llc, Sheila Thunfors and Stone House Properties, Llc, Brian Farrell

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Listing agents

— 21 Stockbridge Rd —

  • Sheila Thunfors

    Stone House Properties, Llc

  • Brian Farrell

    Stone House Properties, Llc

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 21 Stockbridge Rd

School District:Berkshire Hills School District
NameGradesDistance
Muddy Brook Regional Elementary School
318 Monument Valley Road, Great Barrington, MA 01230
PK-46.1 mi
W.E.B. Du Bois Regional Middle School
313 Monument Valley Road, Great Barrington, MA 01230
5-86.2 mi
Monument Mt Regional High School
600 Stockbridge Road, Great Barrington, MA 01230
9-125.9 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 21 Stockbridge Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
4/20/2026
Listed
$1,199,000
84.75%
MLS
3/09/2021
Sold
$649,000
—
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 for 21 Stockbridge Rd

Year
Property Taxes
Change
Tax Assessment
Change
2025
$7,685
6%
$798,900
6%
2024
$7,240
18%
$755,700
27%
2023
$6,138
-22%
$595,300
-5%
2022
$7,890
17%
$628,200
29%
2021
$6,764
6%
$486,300
—
2020
$6,380
8%
$486,300
—
2019
$5,899
—
$486,300
—
2018
$5,899
-3%
$486,300
—
2017
$6,069
19%
$486,300
17%
2016
$5,103
4%
$413,900
—
2015
$4,901
7%
$413,900
1%
2014
$4,566
—
$410,600
—
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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NMLS#: 1598647

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Listed by Stone House Properties, Llc, Sheila Thunfors and Stone House Properties, Llc, Brian Farrell

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21 Stockbridge Rd, West Stockbridge, MA 01266 (MLS# 249230) is a Single Family property with 6 bedrooms, 3 full bathrooms and 1 partial bathroom. 21 Stockbridge Rd is currently listed for $1,199,000 and was received on April 20, 2026. Want to learn more about 21 Stockbridge 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.

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