33 Machine Shop Hill Road
Windham, CT 06266
$524,900
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!!!
| Listing Id: | 24200058 |
|---|---|
| List Price: | $524,900 |
| Property Type: | Single Family |
| Status: | Active |
| Bank Owned Property: | No |
| Beds Total: | 4 |
| Baths Full: | 3 |
| Baths Half: | 1 |
| Living Area Sqft Per Public Record: | 2,548 |
| Property Tax: | $4,963 |
| Acres: | 0.42 |
| Style: | Colonial |
| Direct Waterfront Yn: | No |
| City: | Windham |
| County: | Windham |
| Postal Code: | 06266 |
| Year Built: | 1850 |
| Acres Source: | Public Records |
| Agent Owner Yn: | No |
| Appliances Included: | Oven/Range, Microwave, Refrigerator, Dishwasher |
| Assessed Value: | $166,280 |
| Attic Description: | Unfinished, Storage Space, Floored, Walk-up |
| Attic Yn: | Yes |
| Basement Description: | Yes |
| Basement Description: | Full,Unfinished,Full With Walk-Out |
| Baths Total: | 4 |
| Color: | white |
| Comp Only Manual Yn: | No |
| Cooling System: | Ceiling Fans |
| Current Price: | $524,900.00 |
| Directions: | Use GPS |
| Display Fair Market Value Yn: | Yes |
| Elementary School: | Per Board of Ed |
| Exterior Features: | Porch, Deck, Gutters, Lighting, Stone Wall |
| Exterior Siding: | Vinyl Siding |
| Foundation Type: | Stone |
| Fuel Tank Location: | In Basement |
| Garage & Parking: | Detached Garage |
| Garages Number: | 3 |
| Heat Fuel Type: | Oil |
| Heat Type: | Hot Air |
| High School: | Per Board of Ed |
| Home Owner's Assocation: | No |
| Home Warranty Offered Yn: | No |
| Hot Water Description: | Oil, 50 Gallon Tank |
| In Law Access: | First Floor |
| In Law Apartment: | Yes |
| Laundry Room Info: | Main Level |
| Laundry Room Location: | 2 different locations |
| Listing Contract Date: | 2026-08-20 |
| Lot Description: | Lightly Wooded, Dry, Rolling |
| Mil Rate Total: | $29.85 |
| Status: | Active |
| New Construction Type: | No/Resale |
| Occupied By: | Vacant |
| Original List Price: | $549,900 |
| Parcel Number: | 2290405 |
| Parking Total Spaces: | 3 |
| Possession Availability: | Negotiable |
| Potential Short Sale: | No |
| Preferred Phone: | (860) 917-6090 |
| Price: | $524,900 |
| Roof Information: | Asphalt Shingle |
| Sewage System: | Septic |
| Sign Yn: | Yes |
| Sq Ft Est Heated Above Grade: | 2,548 |
| Sq Ft Total: | 2,548 |
| Swimming Pool Yn: | No |
| Tax Year: | July 2025-June 2026 |
| Total Rooms: | 14 |
| Under Agreement Yn: | No |
| Waterfront Description: | Not Applicable |
| Water Source: | Public Water Connected |
| Year Built Source: | Public Records |
| Zoning: | RVD |
Listing Courtesy of: RE/MAX Bell Park Realty
Listing Agent: Michele Geragotelis
(860) 917-6090
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Smart MLS Inc. data last updated on October 08, 2026 06:45 PM - ET
Property Last Updated: October 08, 2026 06:45 PM - ET