377 Highland Way

$475,000
Price
4
Beds
1,188 Sq. Ft.
$400 / Sq. Ft.
1,188
Sq. Ft.
$400
per Sq. Ft.

Description

Welcome to your dream getaway in Otis Woodlands, one of the Berkshires' premiere private communities. This beautiful home offers the perfect blend of rustic elegance and modern comfort, ideal for year-round living or a serene weekend escape. Nestled among the trees, this spacious 4-bedroom, 3-bathroom home features a dramatic great room with vaulted ceilings and exposed beams, complemented by a 2020 custom kitchen with quartz countertops—perfect for entertaining. Enjoy the outdoors from the expansive...Welcome to your dream getaway in Otis Woodlands, one of the Berkshires' premiere private communities. This beautiful home offers the perfect blend of rustic elegance and modern comfort, ideal for year-round living or a serene weekend escape. Nestled among the trees, this spacious 4-bedroom, 3-bathroom home features a dramatic great room with vaulted ceilings and exposed beams, complemented by a 2020 custom kitchen with quartz countertops—perfect for entertaining. Enjoy the outdoors from the expansive wraparound screened porch, ideal for relaxing or dining al fresco. The upper level boasts a private primary suite with skylights, a full bath, and an open loft area. The main floor includes a bedroom with an en suite bath, while the lower level offers two additional bedrooms

Property Details for 377 Highland Way

Architectural Style
Contemporary
View
Scenic
Parking Spaces Type
Off Street
Waterfront
Yes
Zoning Description
Residential
LISTING UPDATED: 12/16/2025 04:57 PM

Property Details for 377 Highland Way

StatusActive
MLS #246747
Days on Market186
Taxes$3,102 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential
Year Built1985
Lot Size1.00 AC / 43,560 SF
CountyBerkshire County

Location

Listing Courtesy of WILLIAM PITT SOTHEBY'S - LENOX, Thom Garvey
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Building Information for 377 Highland Way

Stories-Year Built1985Building Size-Lot Size1.00 AC / 43,560 SF

Payment Calculator

$2,606 per month

30 year fixed, 6.28% Interest

Principal and Interest

$2,347

Property Taxes

$259

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 377 Highland Way

Summary
Location and General Information
  • Directions: Rt 8 to North Beech Plain Rd (see OWL sign. Right on Woodlands Way. Right on Clubhouse Rd. Left on Lake Shore Dr. to Highland Way.
  • MLS Area Major: South Registry
  • Latitude: 42.18
  • Longitude: -73.10
  • MLS Area Minor: South Registry
  • Views Scenic: Yes
Taxes and HOA
  • Tax Book Number: 2402
  • Parcel Number: 402-0-8
  • Association Fee: $.00
  • Tax Amount: $3,102.00
  • Tax Assessed Value: 310500
  • Assess Amount: $310,500.00
  • Assessed Year: 2024.0
  • Tax Year: 2024
  • Book: 2402
  • Page: 108
  • Fee Includes Blanket Insurance: Yes
  • Fee Includes Management Fees: Yes
  • Fee Includes Road Maintenance: Yes
  • Fee Includes Use of Facilities: Yes
School Information
  • Middle Or Junior School: Monument Valley Reg.
  • High School: Monument Mountain
  • Elementary School: Farmington River
  • Elementry School: Farmington River
  • Middle School: Monument Valley Reg.
Parking
  • Other Parking: Off Street
  • Attached Garage: No
  • Garage None: Yes
Virtual Tour
Property
Lot Information
  • Lot Size Area: 1.0
  • Lot Size Units: Acres
  • Lot Features: Wooded
  • Lot Size Acres: 1.0
  • Lot Size Dimensions: 43560
  • Lot Size Square Feet: 43560.0
  • Square Feet Source: Assessor
  • Living Area: 1188.0
  • Building Area Total: 1188.0
  • Property Type: Residential
  • Lot Description Wooded: Yes
  • Perc Yes: Yes
  • Restrict Covenants Homeowner Association: Yes
Property and Assessments
  • Floor Plans Count: 1
  • Total Bathrooms Source: MLS
  • Photos Count: 61
  • Videos Count: 0
  • Documents Count: 6
  • Property Type: Residential
  • Year Built Description: Actual
  • Easement Unknown: Yes
  • Survey Unknown: Yes
  • Year Built: 1985
  • Year Built Source: Assessor
  • Year Built Details: Actual
  • Flood Hazard Area Unknown: Yes
  • Title V Pass: Yes
  • Title V Date: 7-9-2025
Green Features
  • Energy Features Insulated Doors: Yes
  • Energy Features Insulated Windows: Yes
Utilities
  • Sewer: Private
  • Water Yes: Yes
  • Water Access Well: Yes
  • Drilled Well Detail: Yes
  • Sewer Private: Yes
  • Electric Type 200 Amp: Yes
  • Internet Service Fiber Optic Availabl: Yes
Interior and Exterior Features
Exterior Features
  • Exterior Features: Tennis Court(s), Privacy, Pool - In Ground, Deciduous Shade Trees, Deck
  • Exterior Amenities Deck: Yes
  • Exterior Amenities Pond: Yes
  • Exterior Amenities Pool In Ground: Yes
  • Exterior Amenities Privacy: Yes
  • Exterior Amenities Deciduous Shade Trees: Yes
  • Waterfront Close to Water: Yes
  • Waterfront Lake Access: Yes
  • Waterfront LakePond Name: OWL Lake
  • Waterfront Pond Access: Yes
  • Waterfront Private Beach: Yes
  • Exterior Siding Wood: Yes
  • Foundation Details: Slab
  • Right of Way Unknown: Yes
  • Post Beam Wood Frame: Yes
  • Style Contemporary: Yes
Interior Features
  • Baths Total: 3.00
  • Baths Full: 3
  • Total Bathrooms: 3
  • Bathrooms Total Decimal: 3.00
  • Bathrooms Total Notational: 3.00
  • Total Rooms: 5.00
  • Accessibility 1st Floor Full Bath: Yes
  • Heating: Electric
  • Kitchen Appliances: Dishwasher, Dryer, Range, Refrigerator, Washer
  • Cooling: True
  • Heating: Yes
  • Underground Oil Tank No: Yes
  • Building Information Exterior Color: chocolate
  • Interior Features: Granite Counter, High Speed Wiring, Interior Balcony, Skylight(s), Vaulted Ceilings, Walk-In Closet(s)
  • Interior Amenities Granite Counter: Yes
  • Interior Amenities High Speed Wiring: Yes
  • Interior Amenities Interior Balcony: Yes
  • Interior Amenities Skylight: Yes
  • Interior Amenities Vaulted Ceilings: Yes
  • Interior Amenities WalkIn Closet: Yes
  • Basement Crawl: Yes
  • Basement Interior Access: Yes
  • Basement Slab: Yes
  • Basement Unfinished: Yes
  • Basement Walkout: Yes
  • Heating/Cooling Ductless Wall Unit AC System: Yes
  • Fuel Electric: Yes
  • Hot Water Electric: Yes
  • Insulation Unknown: Yes
  • Appliances Included Dishwasher: Yes
  • Appliances Included Dryer: Yes
  • Appliances Included Refrigerator: Yes
  • Appliances Included Washer: Yes
  • Floor Carpet: Yes
  • Floor Laminate: Yes
  • Floor Wood: Yes
  • Heat/Cool/Vent Electric: Yes
  • Heat/Cool/Vent Heat Pump: Yes
  • Lead Paint NA built after 1978: Yes
Room Information
Room Details
  • Rooms Total: 5
  • Room Type: Kitchen, Great Room, Bedroom 1, Full Bathroom, Primary Bedroom, Primary Bathroom, Loft, Bedroom 3, Bedroom 4, Den, Utility Room
Room 1
  • Room Type: Kitchen
  • Room Level: First
Room 2
  • Room Type: Great Room
  • Room Level: First
Room 3
  • Room Type: Bedroom 1
  • Room Level: First
Room 4
  • Room Type: Full Bathroom
  • Room Level: First
Room 5
  • Room Type: Primary Bedroom
  • Room Level: Second
Room 6
  • Room Type: Primary Bathroom
  • Room Level: Second
Room 7
  • Room Type: Loft
  • Room Level: Second
Room 8
  • Room Type: Bedroom 3
  • Room Level: Lower
Room 9
  • Room Type: Bedroom 4
  • Room Level: Lower
Room 10
  • Room Type: Den
  • Room Level: Lower
Room 11
  • Room Type: Utility Room
  • Room Level: Lower
Room 12
  • Room Type: Full Bathroom
  • Room Level: Lower
Rental
Rental Information
  • Certified Occupancy No: Yes

Property History for 377 Highland Way

DateEvent & SourcePriceAppreciation
Sep 13, 2025

Price Change

Berkshire County Board of REALTORS #246747

$475,000—
Jul 3, 2025

Price Change

Berkshire County Board of REALTORS #246747

$499,000—
Jun 15, 2025

Listed (Active)

Berkshire County Board of REALTORS #246747

$550,000—
Apr 16, 2025

Canceled

Berkshire County Board of REALTORS #243039

—
Jul 10, 2024

Price Change

Berkshire County Board of REALTORS #243039

$550,000—
Apr 26, 2024

Listed (Active)

Berkshire County Board of REALTORS #243039

$579,000—
Nov 22, 1999

Sold (Public Record)

Public Record #88948022

$115,000—
Nov 22, 1999

Sold

Berkshire County Board of REALTORS #146833

$115,000—
Jun 7, 1999

Listed (Active)

Berkshire County Board of REALTORS #146833

$139,000—
DateEvent & SourcePrice
09/13/2025

Price Change

Berkshire County Board of REALTORS #246747

$475,000
07/03/2025

Price Change

Berkshire County Board of REALTORS #246747

$499,000
06/15/2025

Listed (Active)

Berkshire County Board of REALTORS #246747

$550,000
04/16/2025

Canceled

Berkshire County Board of REALTORS #243039

—
07/10/2024

Price Change

Berkshire County Board of REALTORS #243039

$550,000
04/26/2024

Listed (Active)

Berkshire County Board of REALTORS #243039

$579,000
11/22/1999

Sold (Public Record)

Public Record #88948022

$115,000
11/22/1999

Sold

Berkshire County Board of REALTORS #146833

$115,000
06/07/1999

Listed (Active)

Berkshire County Board of REALTORS #146833

$139,000

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

Public Records for 377 Highland Way

Taxable ValueLand$48,900Additions$284,400Total$333,300
Tax Record2025$3,006 ($250 / month)
Home Facts
Beds3Baths2.5Total Finished SqFt1,188 SqFtAbove Grade Finished SqFt1,188 SqFtUnfinished Basement SqFt804 SqFtStories2Lot Size43,560 SqFtStyleSingle Family ResidenceYear Built1985ZoningOWCountyBERKSHIREAPNSNDF M:0402 B:0000 L:8Fireplace TypeHas Fireplace

Schools near 377 Highland Way

This home is within Farmington River Reg School District.
Rating
School
Type
Grades
Distance
Public - PK to 6
Rating
School
Distance
Farmington River Elementary School
PublicPK to 6

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

377 Highland Way is a single family home for sale in Sandisfield, MA 01255. This property was listed for sale on June 15, 2025 by WILLIAM PITT SOTHEBY'S - LENOX, it's currently listed at $475,000. It has been on the market for a total of 186 days and was last sold on November 22, 1999. This listing's school district is Farmington River Reg School District. Nearby schools include Farmington River Elementary School. 377 Highland Way is a 4-bed, 3-bath, 1,188 sqft single family home built in 1985.

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. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of WILLIAM PITT SOTHEBY'S - LENOX, Thom Garvey

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.