33 Machine Shop Hill Road
Windham, Connecticut 06266
- Beds
- 5
- Baths
- 3 | 1
- SqFt
- 2,548
- Acres
- 0.42
- Year Built
- 1850
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
Historic 1850 Charm with Modern Updates & In-Law Living! Step inside this beautifully remodeled 1850 home, thoughtfully updated for today's lifestyle while maintaining the character and charm that makes an older home so special. The main living portion of the home offers 3 spacious bedrooms, 2.5 baths, and a dedicated office space. The heart of the home features a bright and inviting open-concept kitchen, dining room, and living room, providing a comfortable layout for everyday living and entertaining. Main-level laundry adds even more convenience. The separate in-law living area offers first-floor living with 1 bedroom, 1 full bath, its own laundry area, and comfortable living space-ideal for extended family, guests, or multigenerational living. Major improvements include a new roof and new furnace, along with extensive interior renovations throughout. Outside, enjoy a large deck perfect for relaxing, entertaining, or summer gatherings. The property also features 2 detached garages, one that is oversized with heat, providing plenty of room for vehicles, storage, a workshop, or hobbies. It's a must see!!!
Key Facts
- City/Town
- Windham
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 1850
- Days on Market
- 0 days
- Beds
- 5
- 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
11
36 under contract
Median List Price
$360,000
11 active listings
Median Closed Price
$277,500
164 sales
Median Days on Market
23
11 active listings
Median $ / Sq Ft
$172
11 active listings
Sale-to-List Ratio
101.3%
164 sales
How this home compares
List Price
$549,900
vs $360,000 median
52.8% above median
Price / Sq Ft
$216
vs $172 median
25.6% above median
Days on Market
0 days
vs 23 days median
23 days fresher than median
Based on 11 active and 164 closed sales (trailing 12 mo) of single family in Windham. Source: SmartMLS · As of August 21, 2026.
Location
33 Machine Shop Hill Road, Windham, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Aug 13, 2026per month
- Principal & Interest$2,830
- Property Taxes$414
- Insurance$183
- 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
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 #
- 24200058
- 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 8/21/2026. 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 8/21/2026 at 2:20 AM UTC.