# 33 Machine Shop Hill Road, Windham, CT 06266 > **TL;DR:** 4bd/4ba single family, $549,900 ($216/sqft), built 1850, 2,548 sqft. Est. $2,941/mo. Listed 25 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $549,900 | | Price/sqft | $216 | | Bedrooms | 4 | | Bathrooms | 3 full, 1 half | | Square Feet | 2,548 | | Year Built | 1850 | | Lot Size | 18,295 sqft (0.42 acres) | | Property Type | Single Family (Other) | | Status | Active | | Days on Market | 25 | ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $2,781 | | Estimated Insurance | $160 | | **Total** | **$2,941** | ## Nearby Schools - **Elementary:** Per Board of Ed - **High:** Per Board of Ed ## Property Highlights - Built in 1850 - 0.42 acre lot ## Description ### Agent Description 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!!! ## 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 - **Phone:** 8609176090 - **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=24200058&c=propsimple) ## Photos ![33 Machine Shop Hill Road - Photo 1](http://lh.rdcpix.com/121b73b6b6ff33caa6ba22d1644e1f4el-f1835195701r.jpg) ![33 Machine Shop Hill Road - Photo 2](http://lh.rdcpix.com/121b73b6b6ff33caa6ba22d1644e1f4el-f2869897059r.jpg) ![33 Machine Shop Hill Road - Photo 3](http://lh.rdcpix.com/121b73b6b6ff33caa6ba22d1644e1f4el-f885494675r.jpg) ![33 Machine Shop Hill Road - Photo 4](http://lh.rdcpix.com/121b73b6b6ff33caa6ba22d1644e1f4el-f2756650205r.jpg) ![33 Machine Shop Hill Road - Photo 5](http://lh.rdcpix.com/121b73b6b6ff33caa6ba22d1644e1f4el-f852238825r.jpg) ![33 Machine Shop Hill Road - Photo 6](http://lh.rdcpix.com/121b73b6b6ff33caa6ba22d1644e1f4el-f211530472r.jpg) ![33 Machine Shop Hill Road - Photo 7](http://lh.rdcpix.com/121b73b6b6ff33caa6ba22d1644e1f4el-f1822410393r.jpg) ![33 Machine Shop Hill Road - Photo 8](http://lh.rdcpix.com/121b73b6b6ff33caa6ba22d1644e1f4el-f3804520932r.jpg) ![33 Machine Shop Hill Road - Photo 9](http://lh.rdcpix.com/121b73b6b6ff33caa6ba22d1644e1f4el-f3275824832r.jpg) ![33 Machine Shop Hill Road - Photo 10](http://lh.rdcpix.com/121b73b6b6ff33caa6ba22d1644e1f4el-f64125081r.jpg) ![33 Machine Shop Hill Road - Photo 11](http://lh.rdcpix.com/121b73b6b6ff33caa6ba22d1644e1f4el-f3203270855r.jpg) ![33 Machine Shop Hill Road - Photo 12](http://lh.rdcpix.com/121b73b6b6ff33caa6ba22d1644e1f4el-f832550527r.jpg) ![33 Machine Shop Hill Road - Photo 13](http://lh.rdcpix.com/121b73b6b6ff33caa6ba22d1644e1f4el-f3329469796r.jpg) ![33 Machine Shop Hill Road - Photo 14](http://lh.rdcpix.com/121b73b6b6ff33caa6ba22d1644e1f4el-f2283276306r.jpg) ![33 Machine Shop Hill Road - Photo 15](http://lh.rdcpix.com/121b73b6b6ff33caa6ba22d1644e1f4el-f157276181r.jpg) ![33 Machine Shop Hill Road - Photo 16](http://lh.rdcpix.com/121b73b6b6ff33caa6ba22d1644e1f4el-f421755072r.jpg) ![33 Machine Shop Hill Road - Photo 17](http://lh.rdcpix.com/121b73b6b6ff33caa6ba22d1644e1f4el-f2372827389r.jpg) ![33 Machine Shop Hill Road - Photo 18](http://lh.rdcpix.com/121b73b6b6ff33caa6ba22d1644e1f4el-f993509346r.jpg) ![33 Machine Shop Hill Road - Photo 19](http://lh.rdcpix.com/121b73b6b6ff33caa6ba22d1644e1f4el-f3308069551r.jpg) ![33 Machine Shop Hill Road - Photo 20](http://lh.rdcpix.com/121b73b6b6ff33caa6ba22d1644e1f4el-f4257529841r.jpg) ![33 Machine Shop Hill Road - Photo 21](http://lh.rdcpix.com/121b73b6b6ff33caa6ba22d1644e1f4el-f1176698896r.jpg) ![33 Machine Shop Hill Road - Photo 22](http://lh.rdcpix.com/121b73b6b6ff33caa6ba22d1644e1f4el-f2809245101r.jpg) ![33 Machine Shop Hill Road - Photo 23](http://lh.rdcpix.com/121b73b6b6ff33caa6ba22d1644e1f4el-f1065120098r.jpg) ![33 Machine Shop Hill Road - Photo 24](http://lh.rdcpix.com/121b73b6b6ff33caa6ba22d1644e1f4el-f3817211433r.jpg) ![33 Machine Shop Hill Road - Photo 25](http://lh.rdcpix.com/121b73b6b6ff33caa6ba22d1644e1f4el-f854530003r.jpg) ![33 Machine Shop Hill Road - Photo 26](http://lh.rdcpix.com/121b73b6b6ff33caa6ba22d1644e1f4el-f981848527r.jpg) ![33 Machine Shop Hill Road - Photo 27](http://lh.rdcpix.com/121b73b6b6ff33caa6ba22d1644e1f4el-f1046409626r.jpg) ![33 Machine Shop Hill Road - Photo 28](http://lh.rdcpix.com/121b73b6b6ff33caa6ba22d1644e1f4el-f3681720028r.jpg) ![33 Machine Shop Hill Road - Photo 29](http://lh.rdcpix.com/121b73b6b6ff33caa6ba22d1644e1f4el-f1236264363r.jpg) ![33 Machine Shop Hill Road - Photo 30](http://lh.rdcpix.com/121b73b6b6ff33caa6ba22d1644e1f4el-f3575009295r.jpg) --- **MLS#:** 24200058 | **Updated:** 2026-08-21 **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-06266-24200058) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://www.propertysimple.ai/listing/33-machine-shop-hill-road-windham-ct-06266-24200058#listing", "url": "https://www.propertysimple.ai/listing/33-machine-shop-hill-road-windham-ct-06266-24200058", "name": "33 Machine Shop Hill Road, Windham, CT 06266", "description": "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. 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