Active
4 beds2,548 sqft$216/sqft
33 Machine Shop Hill Rd, Windham, CT 06266
Est: $3,209/moGet pre-approved
Single FamilyProperty Type
0.42 acresLot Size
1850Year Built
$216/sq ftPrice per sq ft
3 carsParking Spaces

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....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!
9 days on Market
  • Listed by: Michele Geragotelis 860.917.6090 mlg0378@gmail.com • RE/MAX Bell Park Realty
Last updated: 08/26/2026 07:55 PM • Source: SMARTMLS, MLS#: 24200058

Open Houses

Sunday, Aug 30th11:30 AM - 1:00 PM

Location

Listing Courtesy of RE/MAX Bell Park Realty, Michele Geragotelis
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Payment Calculator

$3,209 per month

30 year fixed, 6.55% Interest

Principal and Interest

$2,795

Property Taxes

$414

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 33 Machine Shop Hill Road

Property Details
  • Taxes: $4,963 / year
  • MLS Type: Residential
  • Basement Description: Full, Unfinished, Full With Walk-Out
  • Direct Waterfront: No
  • Garages Number: 3
  • Style: Colonial
  • Garage Parking Info: Detached Garage
  • Swimming Pool: No
Building Information
  • Year Built: 1850
  • Lot Size: 0.42 AC / 18,295 SF
Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Use GPS
  • Elementary School: Per Board of Ed
  • High School: Per Board of Ed
  • Latitude: 41.678146
  • Longitude: -72.173348
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $4,963
Interior and Exterior Features
Exterior Features
  • Exterior Features: Porch, Deck, Gutters, Lighting, Stone Wall
  • Waterfront Description: Not Applicable
Interior Features
  • Appliances Included: Oven/Range, Microwave, Refrigerator, Dishwasher
  • Attic Description: Unfinished, Storage Space, Floored, Walk-up
  • Cooling System: Ceiling Fans
  • Heat Type: Hot Air
  • Attic YN: Yes
  • Fireplaces Total: 0
  • Laundry Room Info: Main Level
  • Laundry Room Location: 2 different locations
  • Rooms Total: 14
Room 1
  • Room Entry Order: 1
  • Room Level: Main
  • Room Type: Living Room
Room 2
  • Room Entry Order: 10
  • Room Features: Ceiling Fan
  • Room Level: Main
  • Room Type: Living Room
Room 3
  • Room Entry Order: 11
  • Room Features: Ceiling Fan,Laundry Hookup,Walk-In Closet,Laminate Floor
  • Room Level: Main
  • Room Type: Bedroom
Room 4
  • Room Entry Order: 12
  • Room Features: Double-Sink,Stall Shower,Tile Floor
  • Room Level: Main
  • Room Type: Full Bath
Room 5
  • Listing Key: 59532AEDEEF3FF90E063E201100AB280
  • Room Entry Order: 13
  • Room Features: Double-Sink,Tub w/Shower,Tile Floor
  • Room Level: Upper
  • Room Type: Full Bath
Room 6
  • Room Entry Order: 14
  • Room Features: Laundry Hookup,Tile Floor
  • Room Level: Main
  • Room Type: Half Bath
Room 7
  • Room Entry Order: 2
  • Room Features: Balcony/Deck,Beams,Tile Floor
  • Room Level: Main
  • Room Type: Dining Room
Room 8
  • Room Entry Order: 3
  • Room Features: Beams,Breakfast Bar,Granite Counters,Island,Tile Floor
  • Room Level: Main
  • Room Type: Kitchen
Room 9
  • Listing Key: 59532AEDEEF3FF90E063E201100AB280
  • Room Entry Order: 4
  • Room Features: Ceiling Fan,Walk-In Closet
  • Room Level: Upper
  • Room Type: Primary Bedroom
Room 10
  • Room Entry Order: 5
  • Room Features: Double-Sink,Stall Shower,Tile Floor
  • Room Level: Upper
  • Room Type: Primary Bath
Room 11
  • Room Entry Order: 6
  • Room Features: Ceiling Fan
  • Room Level: Upper
  • Room Type: Bedroom
Room 12
  • Room Entry Order: 7
  • Room Features: Ceiling Fan
  • Room Level: Upper
  • Room Type: Bedroom
Room 13
  • Room Entry Order: 8
  • Room Level: Main
  • Room Type: Office
Room 14
  • Room Entry Order: 9
  • Room Level: Main
  • Room Type: Kitchen
Property
Property and Assessments
  • Color: white
  • Construction Description: Frame
  • Exterior Siding: Vinyl Siding
  • Foundation Type: Stone
  • Fuel Tank Location: In Basement
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 1850
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • In Law Access: First Floor
  • In Law Apartment: Yes
  • Living Area SQFT Per Public Records: 2548
Lot Information
  • Lot Description: Lightly Wooded, Dry, Rolling
  • Parcel Number: 2290405
  • Sq Ft Est Heated Above Grade: 2548.0
  • Sq Ft Total: 2548.0
  • Zoning: RVD
Utilities
  • Heat Fuel Type: Oil
  • Hot Water Description: Oil, 50 Gallon Tank
  • Sewage System: Septic
  • Water Source: Public Water Connected
Multi Family
Income and Expenses
  • Occupied By: Vacant

Property History for 33 Machine Shop Hill Road

DateEvent & SourcePriceAppreciation
Dec 23, 2025

Closed (Public Record)

Public Record #1925060582

$160,000
DateEvent & SourcePrice
12/23/2025

Closed (Public Record)

Public Record #1925060582

$160,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 33 Machine Shop Hill Road

Taxable ValueLand$30,060Additions$136,220Total$166,280
Tax Record2025$4,963 ($414 / month)
Home Facts
Beds5Baths2Total Finished SqFt2,548 SqFtAbove Grade Finished SqFt2,548 SqFtUnfinished Basement SqFt1,508 SqFtStories2Lot Size18,295 SqFtStyleSingle Family ResidenceYear Built1850Year Renovated1850ZoningRVDCountySOUTHEASTERN CONNECTICUTAPNWNDH M:16-03 B:183 L:2

Schools near 33 Machine Shop Hill Road

This home is within Windham School District.
Rating
School
Type
Grades
Distance
Public - K to 5
Public - 6 to 8
Public - 9 to 12
Public - K to 8
Rating
School
Distance
Windham Center School
PublicK to 5

Windham Middle School
Public6 to 8

Windham High School
Public9 to 12

Charles High Barrows Stem Academy
PublicK to 8

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

Similar Homes

33 Machine Shop Hill Road is a single family home for sale in Windham, CT 06266. This property was listed for sale on August 20, 2026 by RE/MAX Bell Park Realty, it's currently listed at $549,900. It has been on the market for a total of 9 days and was last sold on December 23, 2025. This listing's school district is Windham School District. Nearby schools include Windham Center School, Windham Middle School and Windham High School. 33 Machine Shop Hill Road is a 4-bed, 4-bath, 2,548 sqft single family home built in 1850.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of RE/MAX Bell Park Realty, Michele Geragotelis

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.