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33 Machine Shop Hill Road

Windham, Connecticut 06266

ACTIVE - NEW$519,900
Beds
4
Baths
3 | 1
SqFt
2,548
Acres
0.42
Year Built
1850
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
Higgins Group Private Brokerage

Request a private showing and get Matt's read on price, condition, and next steps.

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3-Car Garage

About This Home

Beautifully Remodeled Home with Modern Updates & Separate In-Law Living! Welcome to this beautifully renovated home offering the perfect combination of modern comfort, spacious living, and versatility! Thoughtfully updated throughout, this home features an inviting layout designed for today's lifestyle. The main living area offers 3 spacious bedrooms, 2.5 bathrooms, and a dedicated home office. The bright, open-concept kitchen, dining, and living areas create a seamless flow, perfect for everyday living and entertaining. Convenient main-level laundry adds to the home's functionality. A separate in-law living area provides an excellent opportunity for multigenerational living, extended family, or guests. This private space features 1 bedroom, 1 full bathroom, its own laundry area, and a comfortable living space, all conveniently located on the first floor. Extensive renovations throughout, including a new roof and new furnace, offer added value and peace of mind. Step outside to enjoy the spacious deck, ideal for outdoor entertaining, relaxing, or hosting summer gatherings. 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 living arrangements, and impressive garage space, this property offers something for everyone. Move-in ready and full of possibilities-schedule your private showing today!

Key Facts

City/Town
Windham
Neighborhood
N/A
Property / Style
Single Family · Colonial
Year Built
1850
Days on Market
0 days
Beds
4
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

Median Days on Market

39

17 active listings

Median $ / Sq Ft

$151

17 active listings

Sale-to-List Ratio

101.9%

161 sales

How this home compares

List Price

$519,900

vs $217,500 median

2.4× the median

Price / Sq Ft

$204

vs $151 median

35.1% above median

Days on Market

0 days

vs 39 days median

39 days fresher than median

Based on 17 active and 161 closed sales (trailing 12 mo) of single family in Windham. Source: SmartMLS · As of October 19, 2026.

Location

33 Machine Shop Hill Road, Windham, Connecticut

Property + 6 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$3,467

per month

  • Principal & Interest$2,880
  • Property Taxes$414
  • Insurance$173
  • 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
Interior Features
Open Floor Plan

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 #
24215433
MLS Status
Active

Similar Properties

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Listed By

Michele Geragotelis

(860) 917-6090

RE/MAX Bell Park Realty

(860) 774-7600

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 10/19/2026. 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 10/19/2026 at 5:20 PM UTC.