Skip to main content

33 Machine Shop Hill Road

Windham, Connecticut 06266

ACTIVE - NEW$549,900
Beds
5
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.

Call Matt
3-Car Garage

About This Home

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!!!

Key Facts

City/Town
Windham
Neighborhood
N/A
Property / Style
Single Family · Colonial
Year Built
1850
Days on Market
0 days
Beds
5
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

23

11 active listings

Median $ / Sq Ft

$172

11 active listings

Sale-to-List Ratio

101.3%

164 sales

How this home compares

List Price

$549,900

vs $360,000 median

52.8% above median

Price / Sq Ft

$216

vs $172 median

25.6% above median

Days on Market

0 days

vs 23 days median

23 days fresher than median

Based on 11 active and 164 closed sales (trailing 12 mo) of single family in Windham. Source: SmartMLS · As of August 21, 2026.

Location

33 Machine Shop Hill Road, Windham, Connecticut

Property + 8 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$3,427

per month

  • Principal & Interest$2,830
  • Property Taxes$414
  • Insurance$183
  • 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

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 #
24200058
MLS Status
Active

Similar Properties

Homes with a close match in area, property type, and price.

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 8/21/2026. 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 8/21/2026 at 2:20 AM UTC.