33 Machine Shop Hill Road
Windham, Connecticut 06266
- Beds
- 4
- Baths
- 3 | 1
- SqFt
- 2,548
- Acres
- 0.42
- Year Built
- 1850
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
About This Home
Beautifully Remodeled Home with Modern Updates & Separate In-Law Living! Welcome to this beautifully renovated home offering the perfect combination of modern comfort, spacious living, and versatility! Thoughtfully updated throughout, this home features an inviting layout designed for today's lifestyle. The main living area offers 3 spacious bedrooms, 2.5 bathrooms, and a dedicated home office. The bright, open-concept kitchen, dining, and living areas create a seamless flow, perfect for everyday living and entertaining. Convenient main-level laundry adds to the home's functionality. A separate in-law living area provides an excellent opportunity for multigenerational living, extended family, or guests. This private space features 1 bedroom, 1 full bathroom, its own laundry area, and a comfortable living space, all conveniently located on the first floor. Extensive renovations throughout, including a new roof and new furnace, offer added value and peace of mind. Step outside to enjoy the spacious deck, ideal for outdoor entertaining, relaxing, or hosting summer gatherings. The property also features two detached garages, including an oversized heated garage offering exceptional space for vehicles, storage, a workshop, or hobbies. With its beautifully updated interior, flexible living arrangements, and impressive garage space, this property offers something for everyone. Move-in ready and full of possibilities-schedule your private showing today!
Key Facts
- City/Town
- Windham
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 1850
- Days on Market
- 0 days
- Beds
- 4
- Baths
- 3 full · 1 half
- Living Area
- 2,548 sq ft
- Lot Size
- 0.42 acres
- Garage / Parking
- 3 garage
- Property Taxes
- $4,963 / Annually
Market Snapshot
The Windham Market
Single Family · trailing 12 months
Active Listings
17
25 under contract
Median List Price
$217,500
17 active listings
Median Closed Price
$275,000
161 sales
Median Days on Market
39
17 active listings
Median $ / Sq Ft
$151
17 active listings
Sale-to-List Ratio
101.9%
161 sales
How this home compares
List Price
$519,900
vs $217,500 median
2.4× the median
Price / Sq Ft
$204
vs $151 median
35.1% above median
Days on Market
0 days
vs 39 days median
39 days fresher than median
Based on 17 active and 161 closed sales (trailing 12 mo) of single family in Windham. Source: SmartMLS · As of October 19, 2026.
Location
33 Machine Shop Hill Road, Windham, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 15, 2026per month
- Principal & Interest$2,880
- Property Taxes$414
- Insurance$173
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Windham
- Neighborhood
- N/A
- County
- Windham
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 1850
- New Construction
- No/Resale
- Living Area
- 2,548 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot Air
- Heat Fuel
- Oil
- Cooling
- Ceiling Fans
- Laundry
- Main Level
- Laundry Location
- 2 different locations
- Appliances
- Oven/RangeMicrowaveRefrigeratorDishwasher
- Basement
- FullUnfinishedFull With Walk-Out
- In-Law Apartment
- YesFirst Floor
- Interior Features
- Open Floor Plan
Exterior & Lot
- Lot Size
- 0.42 acres
- Zoning
- RVD
- Garage / Parking
- 3 garage spacesDetached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Septic
- Construction
- Vinyl Siding
- Color
- white
- Roof
- Asphalt Shingle
- Foundation
- Stone
- Exterior Features
- PorchDeckGuttersLightingStone Wall
- Lot Description
- Lightly WoodedDryRolling
Listing & Financials
- Property Taxes
- $4,963 / Annually
- Days on Market
- 0
- MLS #
- 24215433
- MLS Status
- Active
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 10/19/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.
Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.
Data last updated on 10/19/2026 at 5:20 PM UTC.