377 Highland Way, Sandisfield, MA 01255 (MLS# 246747)

377 Highland Way, Sandisfield, MA 01255

$467,000

Virtual Tour

https://www.asteroommls.com/pviewer?hideleadgen=1&token=f6fdCCtbrEWDM2F7Z5c2Tg

Property Type: Residential Bedrooms: 4 Baths: 3 Square Footage: 1,188 Lot Size (sq. ft.): 43,560 Status: Closed

Current Price: $467,000 List Date: 11/04/2025 Last Modified: 2/24/2026

Overview

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 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

Supplements: and a cozy family roomplenty of space for family and guests.Additional highlights include: New 4-bedroom septic system Summer 2025 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 ... (Read more)

Listing Details MLS# 246747

Location, Tax & Legal

Registry: South Registry
Street #: 377
Street Name: Highland
Street Ext: Way
State/Province: MA
Postal Code: 01255
Map Ref: 402-0-8
Assess Amt: 310500
Elem School: Farmington River
Middle School: Monument Valley Reg.
High School: Monument Mountain
Assessed Year: 2024
Taxes: 3102
Tax Year: 2024
Page: 108
Concessions: $3,000

Contract Information

Accessory Dwelling Unit: No
Original List Price: 550000
Limited Service: No
Agent Interest: None

General Property Description

Realtor.COM Type: Residential - Single Family
Sq Ft Liv Apx: 1188
Sq Ft Source: Assessor
Total Rooms: 5
Total Bedrooms: 4
Total Full Baths: 3
Total Bathrooms: 3
Parking Spaces Type: Off Street
Surveillance: No
Year Built Apx: 1985
Year Built Source: Assessor
Yr Blt Description: Actual
Lot Size Dimensions: 43560
Acres Apx: Yes
Lot Size SqFt: 43560

Status Change Info

Status Change Date: 2026-02-24
Under Contract Date: 2026-01-19
Contingent: No
Sold Date: 2026-02-24

Title V Date

Title V Date: 7-9-2025

Water Features

Lake/Pond Name: OWL Lake
Close to Water: Yes
Lake: Yes
Lake Access: Yes
Pond: Yes
Pond Access: Yes
Private Beach: Yes

More Information

Building Info

Exterior Color: chocolate

Remarks & Misc

Additional Disclosures: -NEW 4 BDRM SEPTIC SYSTEM INSTALLED JUNE 2025 -$4,000 reserve fund fee due from buyer at closing -NEWER MINI SPLIT HEATING AND COOLING INSTALLED -ARCHITECT DESIGNS AVAILABLE TO REPLACE SPIRAL STAIRCASE -WELL PUMP: 2020 -HOT WATER HEATER: 2020
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!

Restrict Covenants

Homeowner Assoc: Yes

Appliances Incl

Dishwasher: Yes
Dryer: Yes
Range: Yes
Refrigerator: Yes
Washer: Yes

Basement

Crawl: Yes
Interior Access: Yes
Slab: Yes
Unfinished: Yes
Walkout: Yes

Exterior Amenities

Deck: Yes
Pickle Ball Court: Yes
Pool - In Ground: Yes
Privacy: Yes
Tennis Court(s): Yes
Deciduous Shade Trees: Yes

Flood Hazard Area

Unk: Yes

Floor

Carpet: Yes
Ceramic Tile: Yes
Laminate: Yes
Wood: Yes

Fuel

Electric: Yes

Garage

None: Yes

Heat/Cool/Vent

Ductless Wall Unit A/C System: Yes
Electric: Yes
Heat Pump: Yes

Hot Water

Electric: Yes

HOA / Community Fees

HOA Fee (monthly): 217

Interior Amenities

Granite Counter: Yes
High Speed Wiring: Yes
Interior Balcony: Yes
Skylight(s): Yes
Vaulted Ceilings: Yes
Walk-In Closet(s): Yes

Internet Service

Fiber Optic Availabl: Yes

Lead Paint

N/A, built 1978 or later: Yes

Lot Description

Wooded: Yes

Title V

Pass: Yes

Underground Oil Tank

No: Yes

Water

Well: Yes

Right to Farm Comm

Yes: Yes

Well Detail

Drilled: Yes

Sewer

Private: Yes

Easement

Unk: Yes

Survey

Unk: Yes

Right of Way

Unk: Yes

Accessibility

1st Fl Bdrm: Yes
1st Flr Full Bath: Yes

Electric Type

200 Amp: Yes

Energy Features

Insulated Doors: Yes
Insulated Windows: Yes

Views

Scenic: Yes

Construction

Wood Frame: Yes

Roof

Asphalt Shingles: Yes

Style

Contemporary: Yes

Zoning

Residential: Yes

Insulation

Unknown: Yes

Seller Disc

No: Yes

Exterior Siding

Wood: Yes

Mandatory HOA

Yes: Yes

Fee Includes

Blanket Insurance: Yes
Management Fees: Yes
Road Maintenance: Yes
Snow Removal: Yes
Use of Facilities: Yes

Possession

Close Of Escrow: Yes

Financing

Conventional: Yes

Property Features

Restrict Covenants: Homeowner Assoc Title V: Pass Underground Oil Tank: No Water: Well Well Detail: Drilled Sewer: Private Easement: Unk Survey: Unk Right of Way: Unk Right to Farm Comm: Yes Flood Hazard Area: Unk Views: Scenic Water Features: Close to Water; Lake; Lake Access; Pond; Pond Access; Private Beach Lot Description: Wooded Electric Type: 200 Amp Style: Contemporary Interior Amenities: Granite Counter; High Speed Wiring; Interior Balcony; Skylight(s); Vaulted Ceilings; Walk-In Closet(s) Internet Service: Fiber Optic Availabl Accessibility: 1st Fl Bdrm; 1st Flr Full Bath Exterior Amenities: Deck; Pickle Ball Court; Pool - In Ground; Privacy; Tennis Court(s); Deciduous Shade Trees Appliances Incl: Dishwasher; Dryer; Range; Refrigerator; Washer Energy Features: Insulated Doors; Insulated Windows Construction: Wood Frame Exterior Siding: Wood Roof: Asphalt Shingles Basement: Crawl; Interior Access; Slab; Unfinished; Walkout Floor: Carpet; Ceramic Tile; Laminate; Wood Garage: None Fuel: Electric Hot Water: Electric Insulation: Unknown Lead Paint: N/A, built 1978 or later Zoning: Residential Seller Disc: No Mandatory HOA: Yes Fee Includes: Blanket Insurance; Management Fees; Road Maintenance; Snow Removal; Use of Facilities Possession: Close Of Escrow Financing: Conventional

Room Information

Room Name	Level
Kitchen	First
Great Room	First
Bedroom 1	First
Full Bathroom	First
Primary Bedroom	Second
Primary Bathroom	Second
Loft	Second
Bedroom 3	Lower
Bedroom 4	Lower
Den	Lower
Utility Room	Lower
Full Bathroom	Lower

Documents

Parcel Map ›

New Staircase Design Info ›

New Staircase layout ›

Existing Staircase Design Layout ›

Construction of New Staircase Design ›

MA Home Inspection Disclosure ›

Listing Office: WILLIAM PITT SOTHEBY'S - LENOX

Listing Agent: Thom Garvey

Last Updated: February - 24 - 2026

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