399 Under Mountain Rd, Lenox, MA 01240
Property image
Property image
FOR SALE
11.45 ACRES

$7,975,000

  • 8 Beds
  • 6.5 Baths
  • 9,364 sqft (on 11.45 acres)

399 Under Mountain Rd, Lenox, MA 01240

Est. Mortgage $48,502/mo*
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Home Highlights

Single-Family Home
Built in 1900
11.45 acre lot
$852/sqft
Garage

Local Information

  • Map ViewExplore the area around 399 Under Mountain Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

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!
Last check for updates: about 4 hours ago
Listing courtesy of Molly Thomas, (413) 441-3899
COMPASS MASSACHUSETTS , LLC GB
Source: BCMLS, MLS#247997
Also Listed on BCMLS.

Home Details for 399 Under Mountain Rd

Interior Features

Interior Details
Basement: Unfinished,Interior Entry,Full,ConcreteNumber of Rooms: 12
Beds & Baths
Number of Bedrooms: 8Number of Bathrooms: 7Number of Bathrooms (full): 6Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 9364 Square Feet
Appliances & Utilities
Utilities: Trash PrivateAppliances: Dishwasher, Dryer, Range, Range Hood, Refrigerator, WasherDishwasherDryerRefrigeratorWasher
Heating & Cooling
Heating: Propane,Forced Air,Fireplace(s)No CoolingHas HeatingHeating Fuel: Propane
Fireplace & Spa
Has a Fireplace
Gas & Electric
Electric: 200 Amp, 200+ Amp Service
Windows, Doors, Floors & Walls
Window: Bay/Bow WindowFlooring: Ceramic Tile, Wood
Levels, Entrance, & Accessibility
Floors: Ceramic Tile, Wood
View
Has a ViewView: Water, Seasonal, Scenic, Pond, Pasture, Hill/Mountain, Distant
Security
Security: Alarm System

Exterior Features

Exterior Home Features
Roof: Other Recycled ContentPatio / Porch: PatioExterior: Lighting, Mature Landscaping, LandscapedHas a Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2Other Parking: Garaged & Off-StreetHas a GarageNo Attached GarageParking Spaces: 2Parking: Garaged & Off-Street
Pool
Pool: In GroundPool
Frontage
Not on Waterfront
Water & Sewer
Sewer: Private Sewer

Days on Market

Days on Market: 180+

Property Information

Year Built
Year Built: 1900
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Tudor,Cottage
Property Information
Condition: Updated/Remodeled

Price & Status

Price
List Price: $7,975,000Price Per Sqft: $852
Status Change & Dates
Possession Timing: To Be Determined

Active Status

MLS Status: Active

Location

Direction & Address
City: Lenox
School Information
Elementary School: MorrisJr High / Middle School: Lenox MemorialHigh School: Lenox Memorial

Agent Information

Listing Agent
Listing ID: 247997

Building

Building Area
Building Area: 9364 Square Feet

Lot Information

Lot Area: 11.45 Acres

Miscellaneous

BasementMls Number: 247997Water ViewWater View: Water, Pond

Around this home

The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Lenox

At least 23 Trulia users voted on each feature.
  • 96 % Say car is needed

  • 91 % Say yards are well-kept

  • 83 % Say it's dog friendly

  • 80 % Say parking is easy

  • 78 % Say people would walk alone at night

  • 72 % Say kids play outside

  • 69 % Say there's wildlife

  • 68 % Say it's walkable to grocery stores

  • 68 % Say there's holiday spirit

  • 61 % Say it's walkable to restaurants

  • 60 % Say it's quiet

  • 60 % Say streets are well-lit

  • 56 % Say there are sidewalks

  • 56 % Say there are community events

  • 52 % Say they plan to stay for at least 5 years

  • 51 % Say neighbors are friendly

Sourced by Trulia users. Learn more about our methodology.
  • Maurice Matteodo
    "Safe and walkable. Excellent schools. Beat downtown. Tanglewood down the road. Lots of parks and woods nearby."
  • Johnmac
    "We look out for each other and look out for one another. Lived here my entire life! Lots of art, dance, etc. "
  • Stephen Alsdorf
    "Car-dependent, but easy. There’s almost never any traffic (and even what we think of as “traffic” doesn’t really qualify). I drive through what is literally Norman Rockwell America to get to work, passed a farm, and through the center of Stockbridge, Rockwell’s home. Basically the entire thing is on a two-lane country road."
  • Marlene M.
    "Expensive to live. Some Lenox public service people are out of touch. (Selectman and boards) People who visit in the summer are mean and dislike the locals which is very sad! locals are fun loving! Great Schools and teachers and plenty of artsy things to do! "
  • Ksprague
    "The Berkshires is a great place to live, raise a family or retire. I've lived here most of my life and you can't beat the clean air, friendly people, great schools and the outdoors. I'm a skiier, hiker, and bicycle rider and there is no where else so accommodating to all these pursuits. We brought up our kids here and they are happy, healthy, well-adjusted and turning into great young adults. It's a great place to live."

Market trends in Lenox

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
Sale-to-List Price
Price per sq ft
Available listings
35
1
MoM

Home Value

Learn more about this home's value by checking out the value of nearby homes and how much similar homes have sold for.

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.48
Single-Family Home
$4,000,000
06/10/26
7
7
13,261
1.30
Single-Family Home
$2,200,000
03/06/26
6
6.5
7,143
1.40
Single-Family Home
$2,500,000
05/20/26
6
6.5
6,225
1.26
Single-Family Home
$1,800,000
01/06/26
12
10.5
7,979
1.66
Single-Family Home
$1,250,000
09/19/25
4
4.5
3,190
1.57
Single-Family Home
$950,000
12/30/25
3
2.5
2,844
2.59
Single-Family Home
$2,499,000
12/18/25
7
6
6,578
1.21
Single-Family Home
$856,000
10/01/25
3
2
1,630
1.44
Single-Family Home
$638,000
04/15/26
4
2.5
1,856
1.23
Single-Family Home
$425,000
09/22/25
3
2
1,375

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
0.17
-
-
-
-
Off Market
0.39
$678,100
3
2
2,140
Off Market
0.48
$4,000,000
7
7
13,261
Recently Sold
1.13
$689,700
3
3.5
2,568
Off Market
1.13
$597,100
3
2.5
1,634
Off Market
1.13
$639,300
2
2.5
1,931
Off Market
1.13
$633,100
4
2.5
1,720
Off Market
1.13
$627,500
3
2.5
1,720
Off Market
1.13
$659,800
4
3.5
2,100
For Sale
1.16
$1,256,400
3
3
2,401
Off Market
1.17
$476,500
3
1
1,092
Off Market

Price and Tax history

DateEventPrice
Mar 6, 2026
Source: BCMLS #247997
Listed For Sale
$7,975,000
Feb 11, 2022
Source: BCMLS #233680
Sold
$4,835,000
Nov 9, 2021
Source: BCMLS #233680
Pending
$4,935,000
Mar 17, 2021
Source: BCMLS #233680
Listed For Sale
$4,935,000
Mar 29, 2018
Source: BCMLS #213169
Sold
$625,000

LGBTQ Local Legal Protections

Molly Thomas, COMPASS MASSACHUSETTS , LLC GB
Agent Phone: (413) 441-3899
IDX information is provided exclusively for consumers' personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed to be reliable but not guaranteed.
The data relating to real estate for sale on this website comes from Berkshire County Board of Realtors and the Broker Reciprocity Program. Copyright 2026 Berkshire County Board of Realtors. All rights reserved.

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Frequently asked questions about 399 Under Mountain Rd

  • What is the estimated monthly payment for 399 Under Mountain Rd?
    Based on a $7,975,000 list price with 20% down at today's rates, the estimated monthly payment for 399 Under Mountain Rd in Lenox, MA is approximately $50,509 (about $42,459 principal & interest, $7,975 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • What do residents say about Lenox?
    Residents describe Lenox, MA as well-kept, dog-friendly, and easy to park in. Most residents say you need a car. See homes for sale in Lenox, MA.
  • What are the closest schools to 399 Under Mountain Rd?
    The closest schools to 399 Under Mountain Rd in Lenox, MA are Lenox Memorial High School (Middle, rated 7/10), Morris Elementary (Pre-K, rated 8/10).
  • Does 399 Under Mountain Rd have a pool?
    Yes, 399 Under Mountain Rd in Lenox, MA has a pool.
  • Does 399 Under Mountain Rd have laundry facilities?
    Yes, 399 Under Mountain Rd in Lenox, MA has in-unit laundry.
  • How big is the lot at 399 Under Mountain Rd?
    The lot at 399 Under Mountain Rd in Lenox, MA is about 11.5 acres.
399 Under Mountain Rd, Lenox, MA 01240 is a 8 bedroom, 7 bathroom, 9,364 sqft single-family home built in 1900. This property is currently available for sale and was listed by BCMLS on Mar 6, 2026. The MLS # for this home is MLS# 247997.