For sale

$7,975,000

Est. $46,810/mo —

•

9,364

sq ft

399 Under Mountain Rd, Lenox, MA 01240

About this home

Highwick Farm Manor House is a beautifully restored Berkshire Cottage originally built as a gentleman's equestrian estate. After years of meticulous renovation and thoughtful restoration this remarkable property stands now complete, showcasing exquisite craftsmanship and timeless grandeur. Highwick features lead-glass windows framing picturesque views, ten fireplaces, walnut paneling and pocket doors that provide charm and flexibility. Every detail has been curated to embody warmth and sophistication, creating an inviting ambiance that is both refined and welcoming. Ideally located just moments from downtown Lenox, Tanglewood, a local municipal airport and a charming farm, HomeFarm, directly across the street. Highwick offers an unparalleled sanctuary in the heart of the Berkshires!

Single-familyProperty Type

1900Year Built

11.45 acresLot Size

$852Price/Sq.Ft.

2 car garageParking

Listed by Molly Thomas • COMPASS MASSACHUSETTS , LLC GB

Listing updated: Mar 6, 2026 at 11:38am

Redfin checked: a few seconds ago

•Source:BCMLS #247997

Payment calculator

$46,810 per month

Principal and interest$41,912

Property taxes

$3,834

HOA dues

Home insurance

$1,063

Utilities

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Around this home

Schools

K - 12
Preschool & daycare

Morris Elementary

Public PreK-5 • Assigned • 1.3mi

8/10

Lenox Memorial High School

Public 6-12 • Assigned • 2.6mi

7/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Offer insights

399 Under Mountain Rd · $7,975,000

Strong offer

$7.94M and above

75% chance or better to win

Why $7.94M+ 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
Bay/bow window
Fireplace(s)
Granite counters
Sunroom
Walk-in closets

Bathrooms
Six full bathrooms
One half bathroom

Kitchen
Dishwasher
Range hood
Refrigerator
Granite counters

Laundry & utility
Washer
Dryer

Flooring
Wood flooring

Heating & cooling
Propane heating
Has heating

Sale and tax history for 399 Under Mountain Rd

Sale History
Tax History

Date

Event

Price

BCMLS #247997

Mar 6, 2026

Relisted

—

Feb 1, 2026

Listing Removed

—

Oct 14, 2025

Listed

$7,975,000

$852/sq ft

Oct 14, 2025

Listing Removed

—

BCMLS #233680

Feb 11, 2022

Sold

$4,835,000

$516/sq ft

Mar 17, 2021

Listed

$4,935,000

$527/sq ft

+56

Public Remarks

HIGHWICK FARM MANOR HOUSE is nearing its 3 year restoration/renovation in time for the Summer of 2021. Meticulously preserving and restoring the magnificent original details of this Berkshire cottage from the infrastructure to the doorknobs, while renovating it with only the finest of materials for the sought after amenities of a modern lifestyle today, makes this distinctive Lenox home shine in its original grandeur, designed to be luxurious yet cozy and unpretentious. Generously proportioned rooms with walls of windows flooding the house with natural light and taking in the view, with open flow from room to room and the spectacular kitchen/family room not often seen in homes of this era. Perched high above the country road taking in the sweeping southern vista of Parsons Marsh and surrounded by 11 + acres of lawn, orchard and mature trees with a 20 X 50 gunite pool and wonderful new stone work, complete this special offering.

BCMLS #213169

Mar 29, 2018

Sold

$625,000

$67/sq ft

Sep 29, 2015

Listed

$1,300,000

$139/sq ft

+29

Public Remarks

This magnificent Tudor mansion, the manor house of High Wick Farm, offers impressive yet comfortable light-filled rooms, exquisite architectural details, 7 bedrooms, 11 fireplaces, plus indoor & outdoor swimming pools, all majestically set on 11 acres with gorgeous open views of fields & mountains to the south. In a superb location minutes from Tanglewood & Lenox, this is the quintessential Berkshire estate. An additional 95 Acres across the road at 390 Under Mountain is available for a total asking price of $3,650,000: see MLS #219053. The total package includes several residential rental units, as well as equestrian facilities comprising two barns with a total of 50 stalls, an indoor riding ring, and tack rooms.

BCMLS #205036

Sep 24, 2015

Listing Removed

—

Jan 15, 2014

Listed

$2,850,000

$304/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$21,837 (+4.6%)

$615,300 + $1,768,700

$2,384,000

2022

$20,871 (+57.4%)

$512,800 + $1,412,600

$1,925,400

2021

$13,260 (+17.3%)

$469,900 + $668,300

$1,138,200

2020

$11,301 (−10.8%)

$457,800 + $476,200

$934,000

2019

$12,671 (−35.2%)

$457,800 + $602,500

$1,060,300

2018

$19,544 (+0.7%)

$435,000 + $1,174,900

$1,609,900

2017

$19,413 (+2.3%)

$426,200 + $1,163,700

$1,589,900

2016

$18,981 (+1.4%)

$419,900 + $1,141,000

$1,560,900

2015

$18,711

$419,900 + $1,097,600

$1,517,500

Public record

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

11.45 Acres

Year renovated

2015

Finished Sq. Ft.

9,364

Unfinished Sq. Ft.

—

Total Sq. Ft.

9,364

Year built

1900

Style

Single Family Residential

County

Berkshire County

APN

4171581

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 19, 2023.

Historical weather

Lenox, MA • 01240

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

84/ 100

Very good sunlight

Sunscore

There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

8.9 hrs

5.5 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 399 Under Mountain Rd

$7,036,634

$938K under list price of $7.98M

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $670K to $1.3M.

SOLD MAY 29, 2026
$1,272,500 Last sold price
4 beds3.5 baths4,043 sq ft
54 Dunmore Ct, Lenox, MA 01240
$537/sq ft
smaller lot
85 years newer
SOLD JUL 7, 2026
$825,000 Last sold price
5 beds3 baths3,405 sq ft
36 Dunmore Ct, Lenox, MA 01240
$610/sq ft
smaller lot
85 years newer
SOLD DEC 30, 2025
$950,000 Last sold price
3 beds2.5 baths2,844 sq ft
257 W Mountain Rd, Lenox, MA 01240
$518/sq ft
smaller lot
102 years newer
SOLD AUG 28, 2026
$1,165,000 Last sold price
4 beds3 baths3,242 sq ft
15 Interlaken Cross Rd, Stockbridge, MA 01262
$493/sq ft
smaller lot
62 years newer
SOLD OCT 24, 2025
$795,000 Last sold price
3 beds2.5 baths3,056 sq ft
2345 Swamp Rd, Richmond, MA 01254
$592/sq ft
smaller lot
89 years newer
SOLD AUG 20, 2026
$670,000 Last sold price
4 beds2 baths3,599 sq ft
2507 State Rd, Richmond, MA 01254
$666/sq ft
larger lot
130 years older

Rental earnings

Est. $4,635 per month, based on comparable rentals

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