399 Under Mountain Rd

9,364 Sq. Ft.
$852 / Sq. Ft.
9,364
Sq. Ft.
$852
per Sq. Ft.

Description

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,...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!

Listing Agent

  1. Molly Thomas

    Molly Thomas

    Listing Agent

    Compass

    mthomas@compass.com

    P: (413)-441-3899

Property Details for 399 Under Mountain Road

Architectural Style
Tudor, Cottage
View
Water, Seasonal, Scenic, Pond, Pastoral, Hill/Mountain, Distant
Parking Spaces Type
Garaged & Off-Street
Zoning Description
Residential
LISTING UPDATED: 03/06/2026 11:38 AM

Property Details for 399 Under Mountain Road

StatusActive
MLS #247997
Days on Market1
Taxes$46,014 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential
Year Built1900
Lot Size11.45 AC / 498,762 SF
CountyBerkshire County
Buyer's Agent Compensation2.25%

Location

Add your commute

Building Information for 399 Under Mountain Road

Stories-Year Built1900Building Size-Lot Size11.45 AC / 498,762 SF

Payment Calculator

$42,703 per month

30 year fixed, 6.15% Interest

Principal and Interest

$38,869

Property Taxes

$3,835

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 399 Under Mountain Road

Summary
Location and General Information
  • Directions: Rte 183 turn onto Under Mountain RD, right across from Tanglewood main gate.
  • MLS Area Major: Middle Registry
  • Latitude: 42.37
  • Longitude: -73.30
  • MLS Area Minor: Middle Registry
  • Views Distant: Yes
  • Views HillMountain: Yes
  • Views Pastoral: Yes
  • Views Scenic: Yes
  • Views Seasonal: Yes
  • Views Water: Yes
Taxes and HOA
  • Association Fee: $.00
  • Tax Amount: $46,013.61
  • Tax Year: 2025
School Information
  • Middle Or Junior School: Lenox Memorial
  • High School: Lenox Memorial
  • Elementary School: Morris
  • Elementry School: Morris
  • Middle School: Lenox Memorial
Parking
  • Garage Spaces: 2.00
  • Other Parking: Garaged & Off-Street
  • Attached Garage: No
  • Garage Stalls: 2.00
  • Garage Detached: Yes
Virtual Tour
  • Virtual Tours Count: 0
Property
Lot Information
  • Lot Size Area: 11.45
  • Lot Size Units: Acres
  • Lot Size Acres: 11.45
  • Lot Size Dimensions: 498762
  • Lot Size Square Feet: 498762.0
  • Square Feet Source: Assessor
  • Living Area: 9364.0
  • Building Area Total: 9364.0
  • Property Type: Residential
  • Restrict Covenants Unknown: Yes
Property and Assessments
  • Floor Plans Count: 0
  • Total Bathrooms Source: MLS
  • Photos Count: 50
  • Videos Count: 0
  • Documents Count: 4
  • Property Type: Residential
  • New Construction: False
  • Easement Yes: Yes
  • Survey Unknown: Yes
  • Property Condition: Recently Renovated
  • Condition Recently Renovated: Yes
  • Year Built: 1900
  • Year Built Source: Assessor
  • Flood Hazard Area Unknown: Yes
  • Title V Unknown: Yes
Green Features
  • Green Energy Efficient Lighting: Yes
Utilities
  • Sewer: Private
  • Water Unknow: Yes
  • Water Access Public: Yes
  • Sewer Private: Yes
  • Electric Type 200 Amp: Yes
  • Electric Type 400 Amp: Yes
Interior and Exterior Features
Exterior Features
  • Exterior Features: Lighting, Trash Private, Pool - In Ground, Mature Landscaping, Landscaped, Patio
  • Exterior Amenities Landscaped: Yes
  • Exterior Amenities Patio: Yes
  • Exterior Amenities Pool In Ground: Yes
  • Exterior Amenities Trash Private: Yes
  • Exterior Amenities Mature Landscaping: Yes
  • Waterfront Pond: Yes
  • Roof Other: Yes
  • Roof Recycled Content: Yes
  • Exterior Siding Masonry: Yes
  • Exterior Siding Stucco: Yes
  • Right of Way Unknown: Yes
  • Post Beam Masonry: Yes
  • Post Beam Wood Frame: Yes
  • Style Cottage: Yes
  • Style Tudor: Yes
Interior Features
  • Baths Half: 1
  • Baths Total: 7.00
  • Baths Full: 6
  • Total Bathrooms: 7
  • Bathrooms Total Decimal: 6.50
  • Bathrooms Total Notational: 6.10
  • Total Rooms: 12.00
  • Heating: Propane, Forced Air
  • Kitchen Appliances: Dishwasher, Dryer, Range, Range Hood, Refrigerator, Washer
  • Heating: Yes
  • Underground Oil Tank Unk: Yes
  • Building Information Exterior Color: Taupe
  • Building Information Gas Fireplace: 1
  • Building Information Wood Fireplace: 9
  • Interior Features: Alarm System, Bay/Bow Window, Fireplace (s), Granite Counter, Sun Room, Walk-In Closet(s)
  • Interior Amenities Alarm System: Yes
  • Interior Amenities BayBow Window: Yes
  • Interior Amenities Fireplaces: Yes
  • Interior Amenities Granite Counter: Yes
  • Interior Amenities Sun Room: Yes
  • Interior Amenities Central AC: Yes
  • Interior Amenities WalkIn Closet: Yes
  • Basement Concrete Floor: Yes
  • Basement Full: Yes
  • Basement Interior Access: Yes
  • Basement Unfinished: Yes
  • Heating/Cooling HVAC Zones: Yes
  • Fuel Propane: Yes
  • Hot Water Propane: Yes
  • Appliances Included Dishwasher: Yes
  • Appliances Included Dryer: Yes
  • Appliances Included Range Hood: Yes
  • Appliances Included Refrigerator: Yes
  • Appliances Included Washer: Yes
  • Floor Wood: Yes
  • Heat/Cool/Vent Forced Air: Yes
  • Heat/Cool/Vent Multizone: Yes
  • Lead Paint Unk: Yes
Room Information
Room Details
  • Rooms Total: 12
Rental
Rental Information
  • Certified Occupancy No: Yes

Property History for 399 Under Mountain Road

DateEvent & SourcePriceAppreciation
Oct 14, 2025

Listed (Active)

Berkshire County Board of REALTORS #247997

$7,975,000—
Feb 11, 2022

Sold

Berkshire County Board of REALTORS #233680

$4,835,000—
Nov 8, 2021

Contingent

Berkshire County Board of REALTORS #233680

—
Nov 5, 2021

Under Agreement

Berkshire County Board of REALTORS #233680

—
Oct 5, 2021

Contingent

Berkshire County Board of REALTORS #233680

—
Mar 17, 2021

Listed (Active)

Berkshire County Board of REALTORS #233680

$4,935,000—
Mar 29, 2018

Sold

Berkshire County Board of REALTORS #213169

$625,000—
Mar 8, 2018

Contingent

Berkshire County Board of REALTORS #213169

—
Oct 6, 2017

Under Agreement

Berkshire County Board of REALTORS #213169

—
Jul 28, 2017

Price Change

Berkshire County Board of REALTORS #213169

$1,300,000—
Sep 29, 2015

Listed (Active)

Berkshire County Board of REALTORS #213169

$2,450,000—
Sep 24, 2015

Canceled

Berkshire County Board of REALTORS #205036

—
Jan 15, 2014

Listed (Active)

Berkshire County Board of REALTORS #205036

$2,850,000—
DateEvent & SourcePrice
10/14/2025

Listed (Active)

Berkshire County Board of REALTORS #247997

$7,975,000
02/11/2022

Sold

Berkshire County Board of REALTORS #233680

$4,835,000
11/08/2021

Contingent

Berkshire County Board of REALTORS #233680

—
11/05/2021

Under Agreement

Berkshire County Board of REALTORS #233680

—
10/05/2021

Contingent

Berkshire County Board of REALTORS #233680

—
03/17/2021

Listed (Active)

Berkshire County Board of REALTORS #233680

$4,935,000
03/29/2018

Sold

Berkshire County Board of REALTORS #213169

$625,000
03/08/2018

Contingent

Berkshire County Board of REALTORS #213169

—
10/06/2017

Under Agreement

Berkshire County Board of REALTORS #213169

—
07/28/2017

Price Change

Berkshire County Board of REALTORS #213169

$1,300,000
09/29/2015

Listed (Active)

Berkshire County Board of REALTORS #213169

$2,450,000
09/24/2015

Canceled

Berkshire County Board of REALTORS #205036

—
01/15/2014

Listed (Active)

Berkshire County Board of REALTORS #205036

$2,850,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 399 Under Mountain Road

Taxable ValueLand$1,851,100Additions$3,088,100Total$4,939,200
Tax Record2025$44,700 ($3,725 / month)
Home Facts
Beds8Baths6.5Total Finished SqFt9,364 SqFtAbove Grade Finished SqFt9,364 SqFtStories2Lot Size498,762 SqFtStyleSingle Family ResidenceYear Built1900Year Renovated2009ZoningR-1ACountyBERKSHIREAPNLENO M:16 B:016 P:0000 U:00

Schools near 399 Under Mountain Road

This home is within Lenox School District.
Rating
School
Type
Grades
Distance
Public - PK to 5
Public - 6 to 12
Private - PK to 8
Private - PK to 8
Rating
School
Distance
Morris Elementary
PublicPK to 5

Lenox Memorial High School
Public6 to 12

The Montessori School of the Berkshires
PrivatePK to 8

Berkshire Country Day School
PrivatePK to 8

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

Similar Homes

Similar Sold Homes

399 Under Mountain Road is a single family home for sale in Lenox, MA 01240. This listing's school district is Lenox School District. Nearby schools include Morris Elementary, Lenox Memorial High School and The Montessori School of the Berkshires. 399 Under Mountain Road is a 8-bed, 7-bath, 9,364 sqft single family home built in 1900.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

The property listing data and information, or the images, set forth herein were provided to MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS. The property listing data and information, and the images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the images, set forth herein.