4 days on market
Under Contract
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102 Machine Shop Hill Road, Windham CT 06266

Current Price: $499,900

4 beds 3 baths 2966 sq. ft

Last Update: 6/17/2025

Property Type: Single Family For Sale

Public Remarks

Stunning 4-Bedroom Converted Farmhouse on 4+ Private Acres with Exceptional Outbuildings - Welcome to this beautiful 3,000 SF home, perfectly nestled on over 4 acres of serene, private land. With 4 spacious bedrooms and 2.5 baths, it offers generous living spaces, thoughtful details, and unmatched versatility both inside and out. The main level features a well-appointed kitchen with soapstone countertops, under-cabinet lighting, 2 pantries, and a convenient pass-through window to the screened porch-ideal for effortless indoor-outdoor entertaining. Enjoy meals in the formal dining room, unwind in the elegant living room, or relax in the cozy family room with a charming fireplace. The kitchen also opens to a side deck, offering easy access to outdoor dining and scenic views. Upstairs, the expansive primary suite is a true retreat with French doors leading to a private deck that overlooks the property. The en suite bathroom includes double sinks, a soaking tub with views, and a separate shower. A large walk-in closet completes the suite. The upper level also offers three additional bedrooms, a full hall bath, and convenient laundry room. The exterior of the property is a dream for hobbyists, nature lovers, or those seeking extra space. Three incredible outbuildings include: a 3-car garage with a full upper-level storage, a workshop with second-story storage, and a stunning 3-level barn featuring a cupola that offers 360-degree views. Dont miss this one-of-a-kind opportunity.

Map to Property at 102 Machine Shop Hill Road, Windham CT 06266


5th house on the right after fire station going up hill from South Windham center/Rt. 32. Black mailbox on a wooden support.

Residential Property Information for 102 Machine Shop Hill Road, Windham CT 06266

MLS #: 24092550

Style: Farm House,Victorian

Color: Cream

Total Rooms:

Bedrooms: 4

Bathrooms: 3

Acres: 4.04

Year Built: 1865 (Public Records)

New Construction: No/Resale

Home Warranty Offered:

Property Tax: $8,245

Zoning: R1

Mil Rate:

Assessed Value: $275,840 

Potential Short Sale:

Square Footage: Estimated HEATED Sq.Ft. above grade is 2966; below grade sq feet total is ; total sq ft is 2966

Features
Appliances Incl.: Oven/Range,Refrigerator,Dishwasher
Laundry Location & Info: Upper Level 
Fireplaces: 1
Basement Desc.: Full
Exterior Siding: Vinyl Siding
Exterior Features: Porch-Screened,Porch
Foundation: Concrete,Stone
Roof: Asphalt Shingle,Gable
Parking Spaces: 3
Garage/Parking Type: Detached Garage
Swimming Pool: 0
Waterfront Feat.: Not Applicable
Lot Description: Secluded,Treed,Sloping Lot
Occupied: Owner
Utility Information

Hot Water System

Heat Type:

Fueled By: Hot Water.

Cooling: None

Fuel Tank Location: In Basement

Water Service: Private Well

Sewage System: Septic

School Information

Elementary: Per Board of Ed

Intermediate:

Middle:

High School: Windham

Marketing History

Current List Price: $499,900

Original List Price: $499,900

DOM: 4

Listing Date: 5/15/2025

Last Updated: 5/20/2025 1:59:37 PM

Listing Agent and Broker

List Agent Name: Sherry Borgeson

List Office Name: Berkshire Hathaway NE Prop.