102 Machine Shop Hill
Windham, CT 06266
- 4 beds
- 3 baths
- 2,966 sqft
- ~4 acre lot
- $168 per sqft
- 1865 build
- – on site
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.
Last checked:
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Last updated May 15, 2025
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MLS# 24092550 —
The Building
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Year Built:1865
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Year Built Source:Public Records
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New Construction Type:No/Resale
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Style:Farm House, Victorian
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Roof Information:Asphalt Shingle, Gable
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Attic:Yes
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Attic Description:Pull-Down Stairs
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Exterior Siding:Vinyl Siding
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Foundation Type:Concrete, Stone
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Basement Description:Full
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Exterior Features:Porch-Screened, Porch
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SqFt Total:2966
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SqFt Est Heated Above Grade:2966
Interior
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Fireplaces Total:1
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Laundry Room:Upper Level
Room Dimensions
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Living Area SqFt Per Public Record:2966
Location
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Directions:5th house on the right after fire station going up hill from South Windham center/Rt. 32. Black mailbox on a wooden support.
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Neighborhood:South Windham
The Property
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Parcel Number:2291634
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Property Type:Single Family For Sale
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Zoning:R1
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Acres:4.04
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Acres Source:Public Records
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Lot Description:Secluded, Treed, Sloping Lot
Listing Agent
- Contact info:
- Agent phone:
- (860) 537-6699
Taxes
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Tax Year:July 2024-June 2025
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Property Taxes:8245
Beds
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Beds Total:4
Baths
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Total Baths:3
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Full Baths:2
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Half Baths:1
The Listing
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Home Warranty Offered:No
Heating & Cooling
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Heat Type:Hot Water
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Heat Fuel Type:Oil
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Cooling System:None
Utilities
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Water Source:Private Well
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Sewage System:Septic
Appliances
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Appliances Included:Oven/Range, Refrigerator, Dishwasher
Schools
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Elementary School:Per Board of Ed
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High School:Windham
The Community
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Swimming Pool:No
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Direct Waterfront:No
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Waterfront Description:Not Applicable
Parking
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Garage & Parking:Detached Garage
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Garages Number:3
Monthly cost estimate

Asking price
$499,900
Expense | Monthly cost |
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Mortgage
This calculator is intended for planning and education purposes only. It relies on assumptions and information provided by you regarding your goals, expectations and financial situation, and should not be used as your sole source of information. The output of the tool is not a loan offer or solicitation, nor is it financial or legal advice. |
$2,676
|
Taxes | N/A |
Insurance | $137 |
Utilities | $515 See report |
Total | $3,328/mo.* |
*This is an estimate |
Walk Score®
Provided by WalkScore® Inc.
Walk Score is the most well-known measure of walkability for any address. It is based on the distance to a variety of nearby services and pedestrian friendliness. Walk Scores range from 0 (Car-Dependent) to 100 (Walker’s Paradise).
Bike Score®
Provided by WalkScore® Inc.
Bike Score evaluates a location's bikeability. It is calculated by measuring bike infrastructure, hills, destinations and road connectivity, and the number of bike commuters. Bike Scores range from 0 (Somewhat Bikeable) to 100 (Biker’s Paradise).
Soundscore™
Provided by HowLoud
Soundscore is an overall score that accounts for traffic, airport activity, and local sources. A Soundscore rating is a number between 50 (very loud) and 100 (very quiet).
Air Pollution Index
Provided by ClearlyEnergy
The air pollution index is calculated by county or urban area using the past three years data. The index ranks the county or urban area on a scale of 0 (best) - 100 (worst) across the United Sates.
Sale history
Date | Event | Source | Price | % Change |
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5/15/25
May 15, 2025
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Listed / Active | SMART_MLS | $499,900 |