OPEN SAT, 11AM TO 2PM

For sale

$499,000

Est. $2,886/mo —

•

828

sq ft

1 Massasoit Rd, Stockbridge, MA 01262

About this home

Turnkey Berkshire Retreat Near Stockbridge Bowl & Tanglewood - Embrace effortless seasonal living in this beautifully maintained, vintage three-season cottage. Nestled on a quiet, unpaved lane in the desirable Mahkeenac Heights community, this two-bedroom home offers the quintessential Berkshires getaway. Recent thoughtful updates include fresh flooring and an opened-up floor plan that maximizes natural light and flow. Step outside onto expansive decking designed for alfresco dining. Whether you are spending your mornings at the local lake beach or your evenings taking in world-class music at nearby Tanglewood, this private haven offers prime proximity to the best of Lenox and Stockbridge.

Single-familyProperty Type

1961Year Built

0.38 acresLot Size

$603Price/Sq.Ft.

Listed by Karen Climo • WILLIAM PITT SOTHEBY'S - GT BARRINGTON

Listing updated: Aug 28, 2026 at 11:10am

Redfin checked: a few seconds ago

•Source:BCMLS #250678

Payment calculator

$2,886 per month

Principal and interest$2,589

Property taxes

$230

HOA dues

Home insurance

$67

Utilities

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Open houses

Saturday, Aug 29

11:00am - 2:00pm

Nearby open houses (10)

OPEN SAT, 10AM TO 12PM
$1,685,000
4 beds4 baths3,282 sq ft
30 Cliffwood St, Lenox, MA 01240
OPEN SAT, 10AM TO 11:30AM
$349,900
4 beds1 bath1,267 sq ft
198 Allengate Ave, Pittsfield, MA 01201
OPEN SAT, 10AM TO 12PM
$799,000
3 beds2.5 baths2,413 sq ft
131 Fox Run --, Lee, MA 01238
OPEN SAT, 11AM TO 12:30PM
$339,900
3 beds1.5 baths1,218 sq ft
71 Essex St, Pittsfield, MA 01201
OPEN SAT, 11AM TO 12:30PM
$519,999
4 beds2.5 baths2,464 sq ft
19 Terrace Dr, New Lebanon, NY 12125
OPEN SAT, 11AM TO 1PM
$279,900
5 beds2 baths1,933 sq ft
77 Onota St, Pittsfield, MA 01201
OPEN SAT, 11AM TO 12:30PM
$349,900
3 beds2 baths1,720 sq ft
100 Essex St, Pittsfield, MA 01201
OPEN SAT, 1PM TO 2:30PM3D WALKTHROUGH
$365,000
2 beds2 baths1,458 sq ft
136 Cadwell Rd, Pittsfield, MA 01201
OPEN SUN, 10:30AM TO 12PM
$499,000
6 beds2 baths2,640 sq ft
226 Grove St, Great Barrington, MA 01230
OPEN SUN, 11AM TO 1PM
$359,900
4 beds2 baths1,568 sq ft
180 Doreen St, Pittsfield, MA 01201

Around this home

Schools

K - 12
Preschool & daycare

Muddy Brook Regional Elementary School

Public PreK-4 • Assigned • 5.5mi

8/10

W.E.B. Du Bois Regional Middle School

Public 5-8 • Assigned • 5.7mi

6/10

Monument Mt Regional High School

Public 9-12 • Assigned • 5.3mi

5/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Dining

Interior features
Cathedral ceilings
Accessible bedroom
Accessible full bath

Bedrooms
4 total rooms (includes bedrooms and living spaces)

Bathrooms
1 full bathroom

Kitchen
Dishwasher
Refrigerator

Flooring
Wood flooring
Linoleum flooring

Heating & cooling
Electric heating

Sale and tax history for 1 Massasoit Rd

Sale History
Tax History

Date

Event

Price

BCMLS #250678

Aug 28, 2026

Listed

$499,000

$603/sq ft

BCMLS #235252

Oct 8, 2021

Sold

$341,000

$412/sq ft

Jul 30, 2021

Listed

$375,000

$453/sq ft

+23

Public Remarks

LOCATION * STOCKBRIDGE BOWL ACCESS * TURN KEY!!!! This vintage three season, two bedroom cottage is the perfect spot for the person looking for seasonal time spent in the Berkshires. This wonderfully maintained rustic cottage, located on an unpaved country lane in the private community of Mahkeenac Heights, awaits a new steward to enjoy and make memories. The owners have done extensive work on the cottage knocking a wall down, installing flooring and opening the cottage up for an open relaxed floor plan. Wonderful indoor and outdoor spaces with spacious decking to enjoy, in a most private location with seasonal views of the lake and a short distance to the town beach on Stockbridge Bowl or everything Tanglewood has to offer...fantastic access to both Lenox and Stockbridge! A must see!!

BCMLS #216347

Oct 17, 2016

Sold

$225,000

$272/sq ft

Jul 19, 2016

Listed

$239,000

$289/sq ft

BCMLS #184495

Mar 9, 2009

Listing Removed

—

Nov 16, 2008

Listed

$219,000

$264/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$2,379 (+7.3%)

$129,300 + $163,000

$292,300

2022

$2,218 (+7.6%)

$109,700 + $126,800

$236,500

2021

$2,062

$109,700 + $101,100

$210,800

2020

$2,063 (+0.5%)

$109,700 + $99,300

$209,000

2019

$2,052 (+4.9%)

$109,700 + $92,900

$202,600

2018

$1,957 (+15.4%)

$109,700 + $90,800

$200,500

2017

$1,696 (+0.6%)

$109,700 + $65,100

$174,800

2016

$1,686 (+8.8%)

$109,700 + $66,100

$175,800

2015

$1,549

$109,700 + $69,000

$178,700

Public record

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

0.38 Acres

Year renovated

1983

Finished Sq. Ft.

828

Unfinished Sq. Ft.

—

Total Sq. Ft.

828

Year built

1961

Style

Other

County

Berkshire County

APN

3732793

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jun 5, 2023.

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

2/10 Heat Factor

7 days above 92° expected this year, 16 days in 30 years

4/10 Wind Factor

10% chance of strong winds in next 30 years

2/10 Air Factor

1 unhealthy days expected this year, 1 days in 30 years

Provided by First Street

Historical weather

Stockbridge, MA • 01262

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

Try the sun simulator tool to see how light moves across the property at different times of day and year.

Provided by Shadowmap

Redfin Estimate for 1 Massasoit Rd

$500,325

$1,325 over list price of $499K

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $350K to $525K.

SOLD JUN 8, 2026
$520,000 Last sold price
2 beds1 bath904 sq ft
22 Mahkeenac Heights Rd, Stockbridge, MA 01262
$28/sq ft
larger lot
11 years older
SOLD MAR 13, 2026
$475,000 Last sold price
2 beds1 bath1,015 sq ft
18 Hill Rd, Stockbridge, MA 01262
$135/sq ft
larger lot
12 years newer
SOLD JUL 24, 2026
$503,500 Last sold price
3 beds1.5 baths1,376 sq ft
11 Lawton St, Lenox, MA 01240
$237/sq ft
smaller lot
61 years older
SOLD MAY 14, 2026
$525,000 Last sold price
4 beds3 baths1,768 sq ft
1310 Lenox Rd, Richmond, MA 01254
$306/sq ft
larger lot
9 years newer
SOLD NOV 20, 2025
$446,000 Last sold price
3 beds2 baths1,409 sq ft
165 George Street St, Lee, MA 01238
$286/sq ft
larger lot
33 years newer
SOLD JUN 30, 2026
$350,000 Last sold price
2 beds2 baths1,298 sq ft
7 Church St, Stockbridge, MA 01262
$333/sq ft
61 years older

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Early Access listings

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OPEN SUN, 11AM TO 12:30PM

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New listings for sale in 01262

NEW 8 HRS AGO

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13 Glendale Middle Rd, Stockbridge, MA 01262

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2 beds2 baths1,125 sq ft

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Details provided by BCMLS and may not match the public record. Learn more.

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About this home

Payment calculator

See this home in person

Nearby open houses (10)

Around this home

Schools

Lifestyle

Property details

Sale and tax history for 1 Massasoit Rd

Public record

Climate risks

Historical weather

Sun exposure

Redfin Estimate for 1 Massasoit Rd

Early Access listings

Nearby similar homes

New listings for sale in 01262

More real estate resources