86 Winesap Rd

2,299 Sq. Ft.
$182 / Sq. Ft.
2,299
Sq. Ft.
$182
per Sq. Ft.

Description

Nestled in the sought-after Orchards neighborhood, this beautifully upgraded 3-bedroom, 3-bath raised ranch offers refined living with a bright, open layout and timeless Craftsman details throughout. The fireplaced living room showcases hardwood floors and custom built-ins, seamlessly connecting to the dining area, ideal for both everyday living and entertaining. The refreshed kitchen features quality finishes, generous cabinetry, and thoughtful design. The primary suite is a true retreat, complete...Nestled in the sought-after Orchards neighborhood, this beautifully upgraded 3-bedroom, 3-bath raised ranch offers refined living with a bright, open layout and timeless Craftsman details throughout. The fireplaced living room showcases hardwood floors and custom built-ins, seamlessly connecting to the dining area, ideal for both everyday living and entertaining. The refreshed kitchen features quality finishes, generous cabinetry, and thoughtful design. The primary suite is a true retreat, complete with a private bath and an expansive walk-in closet. Two additional bedrooms and a well-appointed laundry room are located on the lower level. Step outside to a new deck overlooking a spacious, flat, fully fenced yard that backs to tranquil woods, providing exceptional privacy.
  1. Listed by Elisha Poirier • STONE HOUSE PROPERTIES, LLC

Property Details for 86 Winesap Road

Architectural Style
Raised Ranch
Parking Spaces Type
Garaged & Off-Street
Zoning Description
Residential
LISTING UPDATED: 01/13/2026 07:39 AM

Property Details for 86 Winesap Road

StatusActive
MLS #248522
Days on Market25
Taxes$6,098 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential
Year Built1985
Lot Size0.34 AC / 14,810 SF
CountyBerkshire County

Location

Listing Courtesy of STONE HOUSE PROPERTIES, LLC, Elisha Poirier
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Building Information for 86 Winesap Road

Stories-Year Built1985Building Size-Lot Size0.34 AC / 14,810 SF

Payment Calculator

$2,550 per month

30 year fixed, 6.15% Interest

Principal and Interest

$2,042

Property Taxes

$508

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 86 Winesap Road

Summary
Location and General Information
  • Directions: East St. to Winesap rd.
  • MLS Area Major: Middle Registry
  • Latitude: 42.45
  • Longitude: -73.20
  • MLS Area Minor: Middle Registry
Taxes and HOA
  • Tax Book Number: 5377
  • Parcel Number: PITT M:M10 B:0009 L:014
  • Association Fee: $.00
  • Tax Amount: $6,098.00
  • Tax Assessed Value: 339900
  • Assess Amount: $339,900.00
  • Assessed Year: 2025.0
  • Tax Year: 2025
  • Book: 5377
  • Page: 331
School Information
  • Middle Or Junior School: Theodore Herberg
  • High School: Pittsfield
  • Elementary School: Williams
  • Elementry School: Williams
  • Middle School: Theodore Herberg
Parking
  • Garage Spaces: 2.00
  • Other Parking: Garaged & Off-Street
  • Attached Garage: Yes
  • Garage Stalls: 2.00
  • Garage Attached: Yes
  • Garage Oversized: Yes
Virtual Tour
  • Virtual Tours Count: 0
Property
Lot Information
  • Lot Size Area: 0.34
  • Lot Size Units: Acres
  • Lot Size Acres: 0.34
  • Lot Size Dimensions: 14,767
  • Lot Size Square Feet: 14810.0
  • Square Feet Source: Assessor
  • Living Area: 2299.0
  • Building Area Total: 2299.0
  • Property Type: Residential
  • Restrict Covenants Unknown: Yes
Property and Assessments
  • Floor Plans Count: 0
  • Total Bathrooms Source: MLS
  • Photos Count: 17
  • Videos Count: 0
  • Documents Count: 1
  • Property Type: Residential
  • Easement Unknown: Yes
  • Survey Unknown: Yes
  • Year Built: 1985
  • Year Built Source: Assessor
  • Flood Hazard Area Unknown: Yes
  • Title V Not Applicable: Yes
Utilities
  • Sewer: Public
  • Water Yes: Yes
  • Water Access Public: Yes
  • Sewer Public: Yes
  • Electric Type 200 Amp: Yes
Interior and Exterior Features
Exterior Features
  • Exterior Siding Vinyl: Yes
  • Right of Way Unknown: Yes
  • Post Beam Wood Frame: Yes
  • Style Raised Ranch: Yes
Interior Features
  • Baths Half: 1
  • Baths Total: 3.00
  • Baths Full: 2
  • Total Bathrooms: 3
  • Bathrooms Total Decimal: 2.50
  • Bathrooms Total Notational: 2.10
  • Total Rooms: 7.00
  • Heating: Nat Gas, Hot Water
  • Kitchen Appliances: Dishwasher, Dryer, Range, Refrigerator, Washer
  • Heating: Yes
  • Underground Oil Tank Unk: Yes
  • Building Information Exterior Color: White
  • Basement Full: Yes
  • Fuel Nat Gas: Yes
  • Hot Water Nat Gas: 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 Hot Water: Yes
  • Lead Paint NA built after 1978: Yes
Room Information
Room Details
  • Rooms Total: 7
Rental
Rental Information
  • Certified Occupancy No: Yes

Property History for 86 Winesap Road

DateEvent & SourcePriceAppreciation
Jan 9, 2026

Listed (Active)

Berkshire County Board of REALTORS #248522

$419,000—
May 16, 2014

Sold

Berkshire County Board of REALTORS #204965

$197,500—
Apr 16, 2014

Under Agreement

Berkshire County Board of REALTORS #204965

—
Mar 1, 2014

Price Change

Berkshire County Board of REALTORS #204965

$209,900—
Jan 9, 2014

Listed (Active)

Berkshire County Board of REALTORS #204965

$219,900—
Oct 29, 2010

Sold (Public Record)

Public Record #298733042

$180,000

+2.4% / yr

Oct 29, 2010

Sold

Berkshire County Board of REALTORS #191777

$180,000—
Sep 28, 2010

Contingent

Berkshire County Board of REALTORS #191777

—
Sep 27, 2010

Under Agreement

Berkshire County Board of REALTORS #191777

—
Sep 3, 2010

Listed (Active)

Berkshire County Board of REALTORS #191777

$194,900—
Jun 7, 2010

Canceled

Berkshire County Board of REALTORS #190385

—
May 20, 2010

Listed (Active)

Berkshire County Board of REALTORS #190385

$189,900—
Feb 16, 2001

Sold (Public Record)

Public Record #86778612

$143,000

+1.5% / yr

Feb 16, 2001

Sold

Berkshire County Board of REALTORS #151989

$143,000—
Nov 16, 2000

Listed (Active)

Berkshire County Board of REALTORS #151989

$163,900—
Jul 31, 1991

Sold (Public Record)

Public Record #86757004

$124,450—
DateEvent & SourcePrice
01/09/2026

Listed (Active)

Berkshire County Board of REALTORS #248522

$419,000
05/16/2014

Sold

Berkshire County Board of REALTORS #204965

$197,500
04/16/2014

Under Agreement

Berkshire County Board of REALTORS #204965

—
03/01/2014

Price Change

Berkshire County Board of REALTORS #204965

$209,900
01/09/2014

Listed (Active)

Berkshire County Board of REALTORS #204965

$219,900
10/29/2010

Sold (Public Record)

Public Record #298733042

$180,000

+2.4% / yr

10/29/2010

Sold

Berkshire County Board of REALTORS #191777

$180,000
09/28/2010

Contingent

Berkshire County Board of REALTORS #191777

—
09/27/2010

Under Agreement

Berkshire County Board of REALTORS #191777

—
09/03/2010

Listed (Active)

Berkshire County Board of REALTORS #191777

$194,900
06/07/2010

Canceled

Berkshire County Board of REALTORS #190385

—
05/20/2010

Listed (Active)

Berkshire County Board of REALTORS #190385

$189,900
02/16/2001

Sold (Public Record)

Public Record #86778612

$143,000

+1.5% / yr

02/16/2001

Sold

Berkshire County Board of REALTORS #151989

$143,000
11/16/2000

Listed (Active)

Berkshire County Board of REALTORS #151989

$163,900
07/31/1991

Sold (Public Record)

Public Record #86757004

$124,450

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

Public Records for 86 Winesap Road

Taxable ValueLand$91,700Additions$248,200Total$339,900
Tax Record2025$6,098 ($508 / month)
Home Facts
Beds1Baths2.5Total Finished SqFt2,299 SqFtAbove Grade Finished SqFt2,299 SqFtStories1Lot Size14,776 SqFtStyleSingle Family ResidenceYear Built1985ZoningR12CountyBERKSHIREAPNPITT M:M10 B:0009 L:014Fireplace TypeHas Fireplace

Schools near 86 Winesap Road

This home is within Pittsfield School District.
Rating
School
Type
Grades
Distance
Public - PK to 5
Public - 6 to 8
Public - 9 to 12
Public - 1 to 12
Rating
School
Distance
Williams Elementary School
PublicPK to 5

Theodore Herberg Middle School
Public6 to 8

Pittsfield High School
Public9 to 12

Pittsfield Public Virtual Academy
Public1 to 12

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

86 Winesap Road is a single family home for sale in Pittsfield, MA 01201. This property was listed for sale on January 9, 2026 by STONE HOUSE PROPERTIES, LLC, it's currently listed at $419,000. It has been on the market for a total of 25 days and was last sold on May 16, 2014. This listing's school district is Pittsfield School District. Nearby schools include Williams Elementary School, Theodore Herberg Middle School and Pittsfield High School. 86 Winesap Road is a 3-bed, 3-bath, 2,299 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.

Listing Courtesy of STONE HOUSE PROPERTIES, LLC, Elisha Poirier

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.