# 33 Machine Shop Hill Road, Windham, CT 06266 > **TL;DR:** 4bd/4ba single family, $499,900 ($196/sqft), built 1850, 2,548 sqft. > 3-car garage. Est. $2,674/mo. Listed 14 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $499,900 | | Price/sqft | $196 | | Bedrooms | 4 | | Bathrooms | 3 full, 1 half | | Square Feet | 2,548 | | Year Built | 1850 | | Lot Size | 18,295 sqft (0.42 acres) | | Garage | 3-car | | Property Type | Single Family (Other) | | Status | Active | | Days on Market | 14 | ## Why This Home Stands Out - **Large Garage** - 3-car garage ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $2,528 | | Estimated Insurance | $146 | | **Total** | **$2,674** | ## Nearby Schools - **Elementary:** Per Board of Ed - **High:** Per Board of Ed ## Key Amenities - 3-car garage ## Property Highlights - Built in 1850 - 0.42 acre lot ## Description ### Agent Description Looking for a home with a little extra room to spread out? This beautifully renovated single-family home offers the perfect combination of modern updates, comfort, and flexibility! One of its standout features is the additional first-floor living space, offering added privacy and versatility for a variety of lifestyle needs. This separate area features comfortable finished living space, a full bathroom, and its own laundry area, providing convenience and functionality. The bright, open-concept kitchen, dining, and living areas create a welcoming atmosphere perfect for everyday living and entertaining. A dedicated home office provides additional flexibility, while convenient main-level laundry adds even more functionality. Extensively remodeled throughout, this move-in-ready home showcases beautiful modern updates, including a new roof and new furnace, offering added value and peace of mind. Step outside to enjoy the spacious deck, perfect for relaxing or entertaining. 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 floor plan, additional first-floor living space, and impressive garage accommodations, this property offers more than meets the eye! Enjoy the comfort of single-family living with a little extra space to make your own. Schedule your private showing today! ## Location - **Address:** 33 Machine Shop Hill Road, Windham, CT 06266 - **County:** Windham - **Coordinates:** 41.6779, -72.173369 - **Google Maps:** https://www.google.com/maps?q=41.6779,-72.173369 ## Listing Agent - **Name:** Michele Geragotelis - **Brokerage:** RE/MAX BELL PARK REALTY - **Broker Phone:** (860) 774-7600 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/33-Machine-Shop-Hill-Rd_South-Windham_CT_06266_M34893-46189?f=listhub&s=CTMLS&m=24215433&c=propsimple) ## Photos ![33 Machine Shop Hill Road - Photo 1](http://lh.rdcpix.com/629fc256b71ae571edeb5cb3edf10f74l-f3908715443r.jpg) ![33 Machine Shop Hill Road - Photo 2](http://lh.rdcpix.com/629fc256b71ae571edeb5cb3edf10f74l-f938593474r.jpg) ![33 Machine Shop Hill Road - Photo 3](http://lh.rdcpix.com/629fc256b71ae571edeb5cb3edf10f74l-f2379986591r.jpg) ![33 Machine Shop Hill Road - Photo 4](http://lh.rdcpix.com/629fc256b71ae571edeb5cb3edf10f74l-f349575799r.jpg) ![33 Machine Shop Hill Road - Photo 5](http://lh.rdcpix.com/629fc256b71ae571edeb5cb3edf10f74l-f2636658354r.jpg) ![33 Machine Shop Hill Road - Photo 6](http://lh.rdcpix.com/629fc256b71ae571edeb5cb3edf10f74l-f3975514791r.jpg) ![33 Machine Shop Hill Road - Photo 7](http://lh.rdcpix.com/629fc256b71ae571edeb5cb3edf10f74l-f1514591689r.jpg) ![33 Machine Shop Hill Road - Photo 8](http://lh.rdcpix.com/629fc256b71ae571edeb5cb3edf10f74l-f2262045298r.jpg) ![33 Machine Shop Hill Road - Photo 9](http://lh.rdcpix.com/629fc256b71ae571edeb5cb3edf10f74l-f2331497056r.jpg) ![33 Machine Shop Hill Road - Photo 10](http://lh.rdcpix.com/629fc256b71ae571edeb5cb3edf10f74l-f4048818305r.jpg) ![33 Machine Shop Hill Road - Photo 11](http://lh.rdcpix.com/629fc256b71ae571edeb5cb3edf10f74l-f250740315r.jpg) ![33 Machine Shop Hill Road - Photo 12](http://lh.rdcpix.com/629fc256b71ae571edeb5cb3edf10f74l-f2603684819r.jpg) ![33 Machine Shop Hill Road - Photo 13](http://lh.rdcpix.com/629fc256b71ae571edeb5cb3edf10f74l-f922033930r.jpg) ![33 Machine Shop Hill Road - Photo 14](http://lh.rdcpix.com/629fc256b71ae571edeb5cb3edf10f74l-f4260633821r.jpg) ![33 Machine Shop Hill Road - Photo 15](http://lh.rdcpix.com/629fc256b71ae571edeb5cb3edf10f74l-f2542479117r.jpg) ![33 Machine Shop Hill Road - Photo 16](http://lh.rdcpix.com/629fc256b71ae571edeb5cb3edf10f74l-f1001999300r.jpg) ![33 Machine Shop Hill Road - Photo 17](http://lh.rdcpix.com/629fc256b71ae571edeb5cb3edf10f74l-f2379310602r.jpg) ![33 Machine Shop Hill Road - Photo 18](http://lh.rdcpix.com/629fc256b71ae571edeb5cb3edf10f74l-f2856374718r.jpg) ![33 Machine Shop Hill Road - Photo 19](http://lh.rdcpix.com/629fc256b71ae571edeb5cb3edf10f74l-f881375421r.jpg) ![33 Machine Shop Hill Road - Photo 20](http://lh.rdcpix.com/629fc256b71ae571edeb5cb3edf10f74l-f2517158744r.jpg) ![33 Machine Shop Hill Road - Photo 21](http://lh.rdcpix.com/629fc256b71ae571edeb5cb3edf10f74l-f217939331r.jpg) ![33 Machine Shop Hill Road - Photo 22](http://lh.rdcpix.com/629fc256b71ae571edeb5cb3edf10f74l-f1505746747r.jpg) ![33 Machine Shop Hill Road - Photo 23](http://lh.rdcpix.com/629fc256b71ae571edeb5cb3edf10f74l-f3724586048r.jpg) ![33 Machine Shop Hill Road - Photo 24](http://lh.rdcpix.com/629fc256b71ae571edeb5cb3edf10f74l-f3524212058r.jpg) ![33 Machine Shop Hill Road - Photo 25](http://lh.rdcpix.com/629fc256b71ae571edeb5cb3edf10f74l-f3702461820r.jpg) ![33 Machine Shop Hill Road - Photo 26](http://lh.rdcpix.com/629fc256b71ae571edeb5cb3edf10f74l-f1241360754r.jpg) ![33 Machine Shop Hill Road - Photo 27](http://lh.rdcpix.com/629fc256b71ae571edeb5cb3edf10f74l-f3917212204r.jpg) ![33 Machine Shop Hill Road - Photo 28](http://lh.rdcpix.com/629fc256b71ae571edeb5cb3edf10f74l-f188872859r.jpg) ![33 Machine Shop Hill Road - Photo 29](http://lh.rdcpix.com/629fc256b71ae571edeb5cb3edf10f74l-f3920043132r.jpg) ![33 Machine Shop Hill Road - Photo 30](http://lh.rdcpix.com/629fc256b71ae571edeb5cb3edf10f74l-f1211031222r.jpg) ![33 Machine Shop Hill Road - Photo 31](http://lh.rdcpix.com/629fc256b71ae571edeb5cb3edf10f74l-f1089614451r.jpg) ![33 Machine Shop Hill Road - Photo 32](http://lh.rdcpix.com/629fc256b71ae571edeb5cb3edf10f74l-f2875061467r.jpg) ![33 Machine Shop Hill Road - Photo 33](http://lh.rdcpix.com/629fc256b71ae571edeb5cb3edf10f74l-f3792466022r.jpg) ![33 Machine Shop Hill Road - Photo 34](http://lh.rdcpix.com/629fc256b71ae571edeb5cb3edf10f74l-f1405301219r.jpg) ![33 Machine Shop Hill Road - Photo 35](http://lh.rdcpix.com/629fc256b71ae571edeb5cb3edf10f74l-f2911694454r.jpg) ![33 Machine Shop Hill Road - Photo 36](http://lh.rdcpix.com/629fc256b71ae571edeb5cb3edf10f74l-f2109916270r.jpg) ![33 Machine Shop Hill Road - Photo 37](http://lh.rdcpix.com/629fc256b71ae571edeb5cb3edf10f74l-f2537801924r.jpg) ![33 Machine Shop Hill Road - Photo 38](http://lh.rdcpix.com/629fc256b71ae571edeb5cb3edf10f74l-f3923628279r.jpg) ![33 Machine Shop Hill Road - Photo 39](http://lh.rdcpix.com/629fc256b71ae571edeb5cb3edf10f74l-f1665490166r.jpg) ![33 Machine Shop Hill Road - Photo 40](http://lh.rdcpix.com/629fc256b71ae571edeb5cb3edf10f74l-f1342846r.jpg) --- **MLS#:** 24215433 | **Updated:** 2026-10-31 **Source:** listhub *Copyright © 2026 SmartMLS, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.* [View on PropertySimple](https://www.propertysimple.ai/listing/33-machine-shop-hill-road-windham-ct-06266-99919f2b5d854dc1a8ad9738f0a743fd) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://www.propertysimple.ai/listing/33-machine-shop-hill-road-windham-ct-06266-99919f2b5d854dc1a8ad9738f0a743fd#listing", "url": "https://www.propertysimple.ai/listing/33-machine-shop-hill-road-windham-ct-06266-99919f2b5d854dc1a8ad9738f0a743fd", "name": "33 Machine Shop Hill Road, Windham, CT 06266", "description": "Looking for a home with a little extra room to spread out? This beautifully renovated single-family home offers the perfect combination of modern updates, comfort, and flexibility! 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