$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*
Get Pre-QualifiedHome Highlights
Single-Family Home
Built in 1900
11.45 acre lot
$852/sqft
Garage
Local Information
-- mins to
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 7 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 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 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: 180+ |
|
|---|
Year Built Year Built: 1900 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Tudor,Cottage |
Property Information Condition: Updated/Remodeled |
|
|---|
Price List Price: $7,975,000Price Per Sqft: $852 |
Status Change & Dates Possession Timing: To Be Determined |
|
|---|
MLS Status: Active |
|
|---|
Direction & Address City: Lenox |
School Information Elementary School: MorrisJr High / Middle School: Lenox MemorialHigh School: Lenox Memorial |
|
|---|
Listing Agent Listing ID: 247997 |
|
|---|
Building Area Building Area: 9364 Square Feet |
|
|---|
Lot Area: 11.45 Acres |
|
|---|
BasementMls Number: 247997Water ViewWater View: Water, Pond |
Around this home
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.
Market trends in Lenox
Last updated July 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
35
1MoM
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
| Date | Event | Price |
|---|---|---|
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 |
Oct 7, 2017 Source: Agent Provided | Pending | $1,300,000 |
Jul 28, 2017 Source: Agent Provided | PriceChange | $1,300,000 Price decreased by 21% |
Apr 12, 2017 Source: Agent Provided | PriceChange | $1,650,000 Price decreased by 8% |
Mar 7, 2017 Source: Agent Provided | PriceChange | $1,800,000 Price decreased by 17% |
Oct 7, 2016 Source: Agent Provided | PriceChange | $2,175,000 Price decreased by 11% |
Oct 15, 2015 Source: Agent Provided | PriceChange | $2,450,000 Price decreased by 14% |
Jan 18, 2014 Source: Agent Provided | Listed For Sale | $2,850,000 |
Jan 4, 2013 Source: Agent Provided | ListingRemoved | $1,250,000 |
Sep 12, 2012 Source: Agent Provided | Listed For Sale | $1,250,000 |
May 4, 2012 Source: Agent Provided | ListingRemoved | $1,250,000 |
May 3, 2012 Source: Agent Provided | Listed For Sale | $1,250,000 |
| Year | Property tax | Tax assessment |
|---|---|---|
| 2025 | $44,700 | $4,939,200 |
Home facts updated by county records
LGBTQ Local Legal Protections
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.
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.
Similar Homes You May Like
New Listings near 399 Under Mountain Rd
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 $50,346 (about $42,296 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.

