102 Machine Shop Hill Rd

Windham, CT 06266

$495,000
Last Sold Price
4
Beds
2,966 Sq. Ft.
$167 / Sq. Ft.
2,966
Sq. Ft.
$167
per Sq. Ft.
Get preapproved with Rocket Mortgage1
Closed 6/18/25
Closed 6/18/25

Description

Stunning 4-Bedroom Converted Farmhouse on 4+ Private Acres with Exceptional Outbuildings - Welcome to this beautiful 3,000 SF home, perfectly nestled on over 4 acres of serene, private land. With 4 spacious bedrooms and 2.5 baths, it offers generous living spaces, thoughtful details, and unmatched versatility both inside and out. The main level features a well-appointed kitchen with soapstone countertops, under-cabinet lighting, 2 pantries, and a convenient pass-through window to the screened porch-ideal...Stunning 4-Bedroom Converted Farmhouse on 4+ Private Acres with Exceptional Outbuildings - Welcome to this beautiful 3,000 SF home, perfectly nestled on over 4 acres of serene, private land. With 4 spacious bedrooms and 2.5 baths, it offers generous living spaces, thoughtful details, and unmatched versatility both inside and out. The main level features a well-appointed kitchen with soapstone countertops, under-cabinet lighting, 2 pantries, and a convenient pass-through window to the screened porch-ideal for effortless indoor-outdoor entertaining. Enjoy meals in the formal dining room, unwind in the elegant living room, or relax in the cozy family room with a charming fireplace. The kitchen also opens to a side deck, offering easy access to outdoor dining and scenic views. Upstairs, the expansive primary suite is a true retreat with French doors leading to a private deck that overlooks the property. The en suite bathroom includes double sinks, a soaking tub with views, and a separate shower. A large walk-in closet completes the suite. The upper level also offers three additional bedrooms, a full hall bath, and convenient laundry room. The exterior of the property is a dream for hobbyists, nature lovers, or those seeking extra space. Three incredible outbuildings include: a 3-car garage with a full upper-level storage, a workshop with second-story storage, and a stunning 3-level barn featuring a cupola that offers 360-degree views. Don't miss this one-of-a-kind opportunity.
  1. Listed by Sherry Borgeson • Berkshire Hathaway NE Prop.
    P: (860)-334-0095 C: (860)-334-0095 sherryborgeson@bhhsne.com

Property Details for 102 Machine Shop Hill Road

Basement Description
Full
Direct Waterfront
No
Garages Number
3
Neighborhood
South Windham
Style
Farm House, Victorian
Garage Parking Info
Detached Garage
Swimming Pool
No
LISTING CLOSED: 06/18/2025 12:00 AM

Property Details for 102 Machine Shop Hill Road

StatusClosed
MLS #24092550
Days on Market4
Taxes$8,245 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential
Year Built1865
Lot Size4.04 AC / 175,982 SF
CountyWindham County
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Location

Listing Courtesy of Berkshire Hathaway NE Prop., Sherry Borgeson

Sold By Berkshire Hathaway NE Prop., Sherry Borgeson

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Building Information for 102 Machine Shop Hill Road

Stories-Year Built1865Building Size-Lot Size4.04 AC / 175,982 SF

Payment Calculator

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$3,154 per month

30 year fixed, 6.36% Interest

Principal and Interest

$2,467

Property Taxes

$687

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 102 Machine Shop Hill Road

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: 5th house on the right after fire station going up hill from South Windham center/Rt. 32. Black mailbox on a wooden support.
  • Elementary School: Per Board of Ed
  • High School: Windham
  • Latitude: 41.67688
  • Longitude: -72.179306
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2024-June 2025
  • Property Tax: $8,245
Interior and Exterior Features
Exterior Features
  • Exterior Features: Porch-Screened, Porch
  • Waterfront Description: Not Applicable
Interior Features
  • Appliances Included: Oven/Range, Refrigerator, Dishwasher
  • Attic Description: Pull-Down Stairs
  • Cooling System: None
  • Heat Type: Hot Water
  • Attic YN: Yes
  • Fireplaces Total: 1
  • Laundry Room Info: Upper Level
  • Rooms Total: 8
Room 1
  • Room Entry Order: 1
  • Room Features: Ceiling Fan,Eating Space,Pantry,Hardwood Floor
  • Room Length: 11.3
  • Room Level: Main
  • Room Type: Kitchen
  • Room Width: 14.2
Room 2
  • Room Entry Order: 2
  • Room Features: Hardwood Floor
  • Room Length: 13.1
  • Room Level: Main
  • Room Type: Living Room
  • Room Width: 14.3
Room 3
  • Room Entry Order: 3
  • Room Features: Hardwood Floor
  • Room Length: 14.1
  • Room Level: Main
  • Room Type: Dining Room
  • Room Width: 12.5
Room 4
  • Room Entry Order: 4
  • Room Features: Fireplace,Hardwood Floor
  • Room Length: 31.7
  • Room Level: Main
  • Room Type: Family Room
  • Room Width: 16.6
Room 5
  • Listing Key: 3415E84FAAA4674DE063D501100A508C
  • Room Entry Order: 5
  • Room Features: Cathedral Ceiling,Bedroom Suite,Ceiling Fan,Full Bath
  • Room Length: 14.6
  • Room Level: Upper
  • Room Type: Primary Bedroom
  • Room Width: 19.8
Room 6
  • Room Entry Order: 6
  • Room Features: Hardwood Floor
  • Room Length: 14.3
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 10.6
Room 7
  • Room Entry Order: 7
  • Room Features: Hardwood Floor
  • Room Length: 16.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 13.6
Room 8
  • Room Entry Order: 8
  • Room Features: Hardwood Floor
  • Room Length: 13.3
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 14.2
Property
Property and Assessments
  • Color: Cream
  • Construction Description: Frame
  • Exterior Siding: Vinyl Siding
  • Foundation Type: Concrete, Stone
  • Fuel Tank Location: In Basement
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle, Gable
  • Year Built: 1865
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • Living Area SQFT Per Public Records: 2966
Lot Information
  • Lot Description: Secluded, Treed, Sloping Lot
  • Parcel Number: 2291634
  • Sq Ft Est Heated Above Grade: 2966.0
  • Sq Ft Total: 2966.0
  • Zoning: R1
Utilities
  • Heat Fuel Type: Oil
  • Hot Water Description: Electric, Upright Tank
  • Radon Mitigation Air: No
  • Radon Mitigation Water: No
  • Sewage System: Septic
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 102 Machine Shop Hill Road

DateEvent & SourcePriceAppreciation
Jun 18, 2025

Closed (Public Record)

Public Record #1905304123

$495,000—
DateEvent & SourcePrice
06/18/2025

Closed (Public Record)

Public Record #1905304123

$495,000

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

Public Records for 102 Machine Shop Hill Road

Taxable ValueLand$38,540Additions$237,300Total$275,840
Tax Record2024$8,234 ($686 / month)
Home Facts
Beds4Baths2.5Total Finished SqFt2,966 SqFtAbove Grade Finished SqFt2,966 SqFtUnfinished Basement SqFt1,081 SqFtStories2Lot Size175,982 SqFtStyleSingle Family ResidenceYear Built1865ZoningR1CountySOUTHEASTERN CONNECTICUTAPNWNDH M:05-11 B:180 L:26Fireplace TypeHas Fireplace

Schools near 102 Machine Shop Hill Road

This home is within Windham School District.
Rating
School
Type
Grades
Distance
Windham Center School
Public - K to 5
Windham Middle School
Public - 6 to 8
Windham High School
Public - 9 to 12
Charles High Barrows Stem Academy
Public - K to 8
Rating
School
Distance
Windham Center School
PublicK to 5

Windham Middle School
Public6 to 8

Windham High School
Public9 to 12

Charles High Barrows Stem Academy
PublicK to 8

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.

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Listing Courtesy of Berkshire Hathaway NE Prop., Sherry Borgeson

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.