$499,000
$51K PRICE DROP

377 Highland Way Sandisfield, MA 01255

Estimated payment $3,015/month

Total Views 5,697
4 Beds
3 Baths
1,188 Sq Ft
$420 Price per Sq Ft

Highlights

  • Tennis Courts
  • Scenic Views
  • Contemporary Architecture
  • In Ground Pool
  • Deck
  • Wooded Lot

About This Home

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

Listing Agent

Thom Garvey

WILLIAM PITT SOTHEBY'S - LENOX License #009530583 Listed on: 06/15/2025

WILLIAM PITT SOTHEBY'S - LENOX

Home Details

Home Type

  • Single Family

Est. Annual Taxes

  • $3,102

Year Built

  • 1985

Lot Details

  • 1 Acre Lot
  • Privacy
  • Wooded Lot
  • Landscaped with Trees

Home Design

  • Contemporary Architecture
  • Slab Foundation
  • Wood Frame Construction
  • Asphalt Shingled Roof
  • Wood Siding

Interior Spaces

  • 1,188 Sq Ft Home
  • Vaulted Ceiling
  • Skylights
  • Insulated Windows
  • Insulated Doors
  • Scenic Vista Views

Kitchen

  • Range
  • Dishwasher
  • Granite Countertops

Flooring

  • Wood
  • Carpet
  • Laminate
  • Ceramic Tile

Bedrooms and Bathrooms

  • 4 Bedrooms
  • Main Floor Bedroom
  • Walk-In Closet
  • 3 Full Bathrooms

Laundry

  • Dryer
  • Washer

Unfinished Basement

  • Walk-Out Basement
  • Interior Basement Entry

Parking

  • Garage
  • No Garage
  • Off-Street Parking

Outdoor Features

  • In Ground Pool
  • Tennis Courts
  • Balcony
  • Deck

Schools

  • Farmington River Elementary School
  • Monument Valley Reg. Middle School
  • Monument Mountain High School

Utilities

  • Ductless Heating Or Cooling System
  • Heat Pump System
  • Well
  • Drilled Well
  • Electric Water Heater
  • Private Sewer
  • Fiber Optics Available

Community Details

  • Mandatory Home Owners Association

Home Details

Home Type

Single Family

Est. Annual Taxes

$3,102

Year Built

1985

Lot Details

0

Listing Details

  • Property Type: Residential - Single Family
  • Property Type: Residential
  • Style: Contemporary
  • Accessibility: 1st Fl Bdrm, 1st Flr Full Bath
  • Construction: Wood Frame
  • 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.
  • Marketing Headline: PERFECT BERKSHIRE COUNTRY RETREAT IN OTIS WOODLANDS! OPEN HOUSE SUN JUNE 22, 11-1
  • Year Built Description: Actual
  • Views: Scenic
  • Estimated Year Built: 1985
  • Right Of Way: Unk
  • Property Water Features: Lake Access, Close to Water, Lake, Pond, Private Beach, Pond Access
  • Special Features: None
  • Property Sub Type: Detached
  • Year Built: 1985

Interior Features

  • Appliances Included: Dishwasher, Washer, Refrigerator, Range, Dryer
  • Total Bedrooms: 4
  • Total Bathrooms: 3.00
  • Total Full Baths: 3
  • Basement: Crawl, Interior Access, Walkout, Unfinished, Slab
  • Insulation: Unknown
  • Interior Amenities: High Speed Wiring, Interior Balcony, Vaulted Ceilings, Granite Counter, Walk-In Closet(s), Skylight(s)
  • Floor: Carpet, Laminate, Wood, Ceramic Tile
  • Sq Ft Liv Apx: 1188.00
  • Total Rooms: 5

Exterior Features

  • Exterior Amenities: Deck, Deciduous Shade Trees, Pickle Ball Court, Pool - In Ground, Tennis Court(s), Privacy
  • Roof: Asphalt Shingles
  • Waterfront Lake Pond Name: OWL Lake
  • Exterior Siding: Wood

Garage/Parking

  • Parking Spaces Type: Garaged & Off-Street
  • Garage: None

Utilities

  • Electric Type: 200 Amp
  • Fuel: Electric
  • Hot Water: Electric
  • Internet Service: Fiber Optic Availabl
  • Sewer: Private
  • Underground Oil Tank: No
  • Water: Well
  • Well Detail: Drilled
  • Flood Hazard Area: Unk
  • Heat Cool Vent: Electric, Ductless Wall Unit A/C System, Heat Pump

Condo/Co-op/Association

  • Mandatory HOA: Yes
  • Fee Includes: Blanket Insurance, Road Maintenance, Snow Removal, Management Fees, Use of Facilities
  • H O A Community Fees H O A Fee: 217.00

Schools

  • Elementary School: Farmington River
  • Middle School: Monument Valley Reg.
  • High School: Monument Mountain

Lot Info

  • Estimated Acres: 1.00
  • Total Assessed Value: 310500.00
  • Assessed Year: 2024.00
  • Lot Description: Wooded
  • Lot Size Sq Ft: 43560.00
  • Map Ref: 402-0-8
  • Right To Farm Comm: Yes
  • Zoning: Residential
  • Lot Dimensions: 43560
  • Easement: Unk
  • Survey: Unk

Green Features

  • Energy Features: Insulated Windows, Insulated Doors

Tax Info

  • Taxes: 3102.00
  • Tax Year: 2024

MLS Schools

  • Elementary School: Farmington River
  • High School: Monument Mountain
  • Middle School: Monument Valley Reg.

Map

Range of Values:

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Home Values in the Area

Source: Public Records

Average Home Value in this Area





Source: Public Records

Tax History

Year Tax Paid Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. Land Improvement
2025 $3,006 $333,300 $48,900 $284,400
2024 $3,102 $310,500 $46,500 $264,000
2023 $2,986 $282,000 $46,500 $235,500
2022 $3,047 $236,200 $49,100 $187,100
2021 $2,096 $225,200 $47,000 $178,200
2020 $0 $225,600 $47,000 $178,600
2019 $2,819 $234,300 $55,700 $178,600
2018 $2,833 $213,200 $49,700 $163,500
2017 $2,833 $213,200 $49,700 $163,500
2016 $2,767 $213,200 $49,700 $163,500
2015 $2,670 $205,400 $49,700 $155,700
2014 $2,609 $205,400 $49,700 $155,700
Source: Public Records

Property History

Date Event Price Change Sq Ft Price
07/03/2025 07/03/25 Price Changed $499,000 -9.3% $420 / Sq Ft
06/15/2025 06/15/25 For Sale $550,000 -- $463 / Sq Ft
Source: Berkshire County Board of REALTORS®

Purchase History

Date Type Sale Price Title Company
Quit Claim Deed -- --
Quit Claim Deed -- --
Quit Claim Deed -- --
Quit Claim Deed -- --
Quit Claim Deed -- --
Quit Claim Deed -- --
Quit Claim Deed -- --
Quit Claim Deed -- --
Deed -- --
Deed -- --
Deed $115,000 --
Deed $115,000 --
Source: Public Records

Mortgage History

Date Status Loan Amount Loan Type
Previous Owner $187,000 No Value Available
Previous Owner $200,000 No Value Available
Previous Owner $60,000 Purchase Money Mortgage
Source: Public Records

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Source: Berkshire County Board of REALTORS®

MLS Number: 246747

Berkshire County Board of REALTORS®

APN: SAND-000402-000000-000008