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$475,000

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 1,188 Sq. Ft.
  • 1 Acres
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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 and a cozy family roomplenty of space for family and guests.Additional highlights include: New 4-bedroom septic system 3 newer mini-split units (2023) for efficient heating and cooling $4,000 reserve fund fee due from buyer at closing As part of Otis Woodlands, you'll have access to a full range of amenities: a private lake with beach and playground, heated outdoor pool, modern clubhouse lodge, fitness room, tennis and pickleball courts, and year-round community events.Conveniently located near Otis Ski Ridge, Otis Reservoir, Big Pond, local restaurants, general stores, Jacobs Pillow Dance Festival, and countless hiking trails. -architect designs available to replace spiral staircase -WELL PUMP: 2022 -HOT WATER HEATER: 2020 -MINI SPLIT AC/HEAT PUMP SYSTEM: 2024 -ROOF: APPROX. 15 YEARS OLD

Full Property Details for 377 Highland Way

General

  • Price: $475,000
  • Taxes: $3,102 (2024)
  • Status: Active
  • Type: Single Family
  • Source: 1109
  • MLS ID: 246747
  • Updated: 9/20/2025
  • Added to Site: 216 day(s) ago

Interior

  • Number of Rooms: 5
  • Interior Features: Granite Counter, High Speed Wiring, Interior Balcony, Skylight(s), Vaulted Ceilings, Walk-In Closet(s)
  • Appliances: Dishwasher, Dryer, Range, Refrigerator, Washer
  • Flooring: Carpet, Ceramic Tile, Laminate, Wood

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 3

Bedrooms

  • Total Bedrooms: 4

Additional Information

  • Shared Amenities: Pickle Ball Court
  • Pool: Yes

Exterior

  • Exterior Features: Tennis Court(s), Privacy, Pool - In Ground, Deciduous Shade Trees, Deck

Parking

  • Parking Features: Off Street
  • Other Parking Type: Off Street

Location

  • Area: South Registry

Heating & Cooling

  • Air Conditioning: Yes
  • Cooling Type: Electric
  • Heating Type: Electric

Utilities

  • Sewer: Private Sewer
  • Water: Well
  • Well: Yes
  • Utility Description: Fiber Optic Availabl

Structural Information

  • Architectural Style: Contemporary
  • Foundation: Slab
  • Roof: Asphalt Shingles
  • Windows: Insulated Windows
  • Square Feet: 1,188
  • Year Built: 1985
  • Year Built Source: Assessor

Lot Features

  • Lot Size (Acres): 1
  • Lot Size (Sq. Ft.): 43,560
  • Lot Dimensions: 43560
  • Lot Features: Wooded
  • Zoning: Residential

Water Features

  • Water Front: Yes
  • Water Front Desc.: Private Beach, Pond Access, Pond, Lake Access, Lake, Close to Water

Financial Considerations

  • Tax Amount: $3,102
  • Tax Year: 2024

Disclosures and Reports

  • Property ID: 402-0-8

Listed by William Pitt Sotheby's - Lenox, Thom Garvey

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Listing agent

— 377 Highland Way —

  • Thom Garvey

    William Pitt Sotheby's - Lenox

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 377 Highland Way

School District:Farmington River Regional School District
NameGradesDistance
Farmington River Elementary School
555 North Main Road, Otis, MA 01253
PK-61.5 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 377 Highland Way Get Price Alerts and Save Property

Date
Details
Price
Change
Source
9/13/2025
Price Reduced
$475,000
-4.81%
MLS
7/03/2025
Price Reduced
$499,000
-9.27%
MLS
6/15/2025
Listed
$550,000
378.26%
MLS
11/22/1999
Sold
$115,000
—
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 377 Highland Way

Year
Property Taxes
Change
Tax Assessment
Change
2025
$3,006
-3%
$333,300
7%
2024
$3,102
4%
$310,500
10%
2023
$2,986
-2%
$282,000
19%
2022
$3,047
1%
$236,200
5%
2021
$3,006
—
$225,200
—
2020
$3,000
6%
$225,600
6%
2018
$2,833
—
$213,200
—
2017
$2,833
2%
$213,200
—
2016
$2,767
4%
$213,200
4%
2015
$2,670
2%
$205,400
—
2014
$2,609
—
$205,400
—
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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NMLS#: 1598647

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Listed by William Pitt Sotheby's - Lenox, Thom Garvey

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377 Highland Way, Sandisfield, MA 01255 (MLS# 246747) is a Single Family property with 4 bedrooms and 3 full bathrooms. 377 Highland Way is currently listed for $475,000 and was received on June 15, 2025. Want to learn more about 377 Highland Way? Do you have questions about finding other Single Family real estate for sale in Sandisfield? You can browse all Sandisfield real estate or contact a Coldwell Banker agent to request more information.

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