For sale

$2,400,000

Est. $14,209/mo —

•

6,092

sq ft

89 Undermountain Rd, Egremont, MA 01258

About this home

Welcome to Treetops. A long private driveway passing a large pond sets the scene for this impressive hilltop retreat with 6,000 square feet across three levels and seasonal views of the Taconic Hills. Built with wood hewn from trees on the property, including the distinctive stairway, the home offers a huge open-plan main level ideal for gatherings, along with an indoor pool, hot tub, sauna and a dramatic two-story primary suite. Five bedrooms and five baths provide ample space for guests, with additional bedrooms on the upper and lower levels plus a family room downstairs. A second home may be built on a conserved, included, second parcel. Expansive decks, a three-car garage, sold fully furnished, and abutting the Appalachian Trail conservation lands complete the offering.

Single-familyProperty Type

1988Year Built

30.44 acresLot Size

$394Price/Sq.Ft.

2 car garageParking

Listed by Timothy Lovett • COMPASS MASSACHUSETTS , LLC GB

Listed by Fintan Hanley • COMPASS MASSACHUSETTS , LLC GB

Listing updated: May 27, 2026 at 08:26pm

Redfin checked: a few seconds ago

•Source:BCMLS #249684

Payment calculator

$14,209 per month

Principal and interest$12,613

Property taxes

$1,276

HOA dues

Home insurance

$320

Utilities

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Open houses

No upcoming open houses.

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Around this home

Schools

K - 12
Preschool & daycare

New Marlborough Central School

Public PreK-3 • Assigned • 3.1mi

7/10

Mount Everett Regional School

Public 6-12 • Assigned • 3.1mi

6/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Offer insights

89 Undermountain Rd · $2,400,000

Strong offer

$2.39M and above

75% chance or better to win

Why $2.39M+ is a strong offer

DAYS ON MARKET

The average home goes pending in 42 days.

SALE-TO-LIST

Most homes are selling 2% below list price.

About offer insights

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Dining

Interior features
Alarm system
Cathedral ceilings
Fireplace(s)
Hot tub
Interior balcony
Sauna
Walk-in closet(s)

Bedrooms
Accessible bedroom
First-floor bedroom with bath

Bathrooms
5 full bathrooms
Accessible full bath
First-floor half bath

Kitchen
Cooktop
Dishwasher
Microwave
Refrigerator

Laundry & utility
Washer
Dryer

Flooring
Carpet
Wood

Heating & cooling
Oil heating

Sale and tax history for 89 Undermountain Rd

Sale History
Tax History

Date

Event

Price

BCMLS #249684

May 27, 2026

Listed

$2,400,000

$394/sq ft

BCMLS #231961

May 11, 2021

Sold

$2,075,000

$341/sq ft

Aug 19, 2020

Listed

$2,250,000

$369/sq ft

+42

Public Remarks

TreeTops: Special 30-acre mountainside retreat. Absolute serenity with views... now with fiber internet! A beautiful long driveway takes you past a private pond & up to a stunning contemporary home. Take a swim in the heated, large indoor pool, hot tub, & relax in the steam of the indoor sauna. Friends and extended family have plenty of room to share this beautiful home! Large windows with lots of light & an open floor plan.... 3 floors of beautiful living spaces including a fabulous billiards and game space! Finish your evenings on the large deck listening to the wind on the pines.

Smart MLS #L149981

Jan 9, 2015

Listing Removed

—

May 9, 2014

Listed

$2,495,000

$410/sq ft

Public Records

Feb 14, 2007

Sold

$2,200,000

$361/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$14,367 (−8.9%)

$586,800 + $1,465,600

$2,052,400

2022

$15,766 (+11.1%)

$579,900 + $1,408,200

$1,988,100

2021

$14,190 (+0.1%)

$483,200 + $1,034,500

$1,517,700

2020

$14,172 (+2.5%)

$483,200 + $1,010,200

$1,493,400

2019

$13,828 (+2.5%)

$457,100 + $987,800

$1,444,900

2018

$13,486 (+6.5%)

$449,400 + $952,500

$1,401,900

2016

$12,663 (+12.9%)

$425,400 + $952,500

$1,377,900

2014

$11,214

$404,400 + $953,200

$1,357,600

Public record

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

20.44 Acres

Year renovated

—

Finished Sq. Ft.

6,092

Unfinished Sq. Ft.

—

Total Sq. Ft.

6,092

Year built

1988

Style

Single Family Residential

County

Berkshire County

APN

3955975

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Mar 10, 2026.

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

3/10 Heat Factor

7 days above 93° 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, 2 days in 30 years

Provided by First Street

Historical weather

Egremont, MA • 01258

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

94/ 100

Exceptional sunlight

Sunscore

This home ranks in the top 16% for direct sun exposure in the zip code. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

11.1 hrs

6 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 89 Undermountain Rd

$2,286,789

$113K under list price of $2.40M

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $794K to $2.7M.

SOLD AUG 4, 2026
$862,000 Last sold price
4 beds2.5 baths2,114 sq ft
11 Prospect St, Great Barrington, MA 01230
$14/sq ft
smaller lot
38 years older
SOLD DEC 19, 2025
$1,275,000 Last sold price
4 beds3.5 baths3,194 sq ft
94 West Ave, Great Barrington, MA 01230
$5/sq ft
smaller lot
113 years older
SOLD JUL 17, 2026
$825,000 Last sold price
4 beds1.5 baths1,952 sq ft
115 Baldwin Hill Rd, Great Barrington, MA 01230
$29/sq ft
smaller lot
75 years older
SOLD JAN 23, 2026
$2,675,000 Last sold price
4 beds3.5 baths3,459 sq ft
232 Giberson Rd, Sheffield, MA 01257
$379/sq ft
larger lot
9 years newer
SOLD JAN 6, 2026
$1,150,000 Last sold price
4 beds4.5 baths2,753 sq ft
213 Egremont Plain Rd, Egremont, MA 01230
$24/sq ft
smaller lot
228 years older
SOLD MAR 16, 2026
$794,000 Last sold price
4 beds2 baths2,105 sq ft
12 Barrington Pl, Great Barrington, MA 01230
$17/sq ft
smaller lot
88 years older

Rental earnings

Est. $4,544 per month, based on comparable rentals

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