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$7,975,000

  • For Sale
  • Active
  • Single Family
  • 8 Beds
  • 6 Full Baths
  • 1 Partial Bath
  • 9,364 Sq. Ft.
  • 11.45 Acres
  • 2 Car Garage
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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!

Full Property Details for 399 Under Mountain Rd

General

  • Price: $7,975,000
  • Taxes: $46,013 (2025)
  • Status: Active
  • Type: Single Family
  • Source: 1109
  • MLS ID: 247997
  • Updated: 3/6/2026
  • Added to Site: 177 day(s) ago

Interior

  • Number of Rooms: 12
  • Interior Features: Alarm System, Bay/Bow Window, Fireplace (s), Granite Counter, Sun Room, Walk-In Closet(s)
  • Appliances: Dishwasher, Dryer, Range, Range Hood, Refrigerator, Washer
  • Flooring: Ceramic Tile, Wood

Rooms

Bathrooms

  • Total Bathrooms: 7
  • Full Bathrooms: 6
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 8

Additional Information

  • Pool: Yes

Exterior

  • Exterior Features: Lighting, Trash Private, Pool - In Ground, Mature Landscaping, Landscaped, Patio

Parking

  • Garage Spaces: 2
  • Parking Features: Garaged & Off-Street
  • Other Parking Type: Garaged & Off-Street
  • Garage Description: Detached

Location

  • Area: Middle Registry

Heating & Cooling

  • Heating Type: Propane, Forced Air

Utilities

  • Sewer: Private Sewer
  • Water: Public

Structural Information

  • Architectural Style: Tudor, Cottage
  • Roof: Other, Recycled Content
  • Square Feet: 9,364
  • Year Built: 1900
  • Year Built Source: Assessor
  • Property Condition: Updated/Remodeled

Lot Features

  • Lot Size (Acres): 11.45
  • Lot Size (Sq. Ft.): 498,762
  • Lot Dimensions: 498762
  • Zoning: Residential

Financial Considerations

  • Tax Amount: $46,013.61
  • Tax Year: 2025

Listed by Compass Massachusetts , Llc Gb, Molly Thomas

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Listing agent

— 399 Under Mountain Rd —

  • Molly Thomas

    Compass Massachusetts , Llc Gb

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 399 Under Mountain Rd

School District:Lenox School District
NameGradesDistance
Morris Elementary
129 West Street, Lenox, MA 01240
PK-51.3 mi
Lenox Memorial High School
197 East Street, Lenox, MA 01240
6-122.6 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 399 Under Mountain Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
10/14/2025
Listed
$7,975,000
64.94%
MLS
2/08/2022
Sold
$4,835,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 399 Under Mountain Rd

Year
Property Taxes
Change
Tax Assessment
Change
2025
$44,700
6%
$4,939,200
6%
2024
$42,281
94%
$4,661,600
96%
2023
$21,837
5%
$2,384,000
24%
2022
$20,871
57%
$1,925,400
69%
2021
$13,260
17%
$1,138,200
22%
2020
$11,301
-11%
$934,000
-12%
2019
$12,671
-35%
$1,060,300
-34%
2018
$19,544
1%
$1,609,900
1%
2017
$19,413
2%
$1,589,900
2%
2016
$18,981
1%
$1,560,900
3%
2015
$18,711
-1%
$1,517,500
-3%
2014
$18,859
—
$1,562,500
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Listed by Compass Massachusetts , Llc Gb, Molly Thomas

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399 Under Mountain Rd, Lenox, MA 01240 (MLS# 247997) is a Single Family property with 8 bedrooms, 6 full bathrooms and 1 partial bathroom. 399 Under Mountain Rd is currently listed for $7,975,000 and was received on October 14, 2025. Want to learn more about 399 Under Mountain Rd? Do you have questions about finding other Single Family real estate for sale in Lenox? You can browse all Lenox real estate or contact a Coldwell Banker agent to request more information.

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