102 Machine Shop Hill Road, Windham, CT 06266 - Photo 1

1/1

$495,000

Sold
Closed
Single Family
4 Beds
2 Full Baths
1 Partial Bath
2,966 Sq. Ft.
3 Car Garage

1/1

Property Description

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. Don't miss this one-of-a-kind opportunity.

Full Property Details

Full Property Details for 102 Machine Shop Hill Rd

General

Sold For: $495,000
Taxes: (July 2024-June 2025)
Status: Closed
Type: Single Family
Source: SMARTMLS
MLS ID: 24092550
Added to Site: 251 day(s) ago

Interior

Number of Rooms: 8
Fireplace: Yes
Number of Fireplaces: 1
Appliances: Oven/Range, Refrigerator, Dishwasher

Rooms

Bathrooms

Total Bathrooms: 3
Full Bathrooms: 2
Half Bathrooms: 1

Bedrooms

Total Bedrooms: 4
Primary Bedroom: Primary Bedroom - Cathedral Ceiling, Bedroom Suite, Ceiling Fan, Full Bath, 14.6 x 19.8, Upper
Bedroom 1: Bedroom - Hardwood Floor, 13.3 x 14.2, Upper
Bedroom 2: Bedroom - Hardwood Floor, 14.3 x 10.6, Upper
Bedroom 3: Bedroom - Hardwood Floor, 16 x 13.6, Upper

Other Rooms

Living Room: Living Room - Hardwood Floor, 13.1 x 14.3, Main
Family Room: Family Room - Fireplace, Hardwood Floor, 31.7 x 16.6, Main
Kitchen: Kitchen - Ceiling Fan, Eating Space, Pantry, Hardwood Floor, 11.3 x 14.2, Main
Dining Room: Dining Room - Hardwood Floor, 14.1 x 12.5, Main
Laundry: Upper Level

Exterior

Exterior Features: Porch-Screened, Porch
Color: Cream

Parking

Garage: Yes
Garage Spaces: 3
Parking: Detached Garage

Location

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

School Information

Elementary School: Per Board of Ed
High School: Windham

Community

Community Name: South Windham

Heating & Cooling

Cooling Type: None
Heating Type: Hot Water, Oil
Heating Fuel: Oil
Water Heater: Electric, Upright Tank

Utilities

Sewer: Septic
Water: Private Well

Structural Information

Architectural Style: Farm House, Victorian
Construction Status: No/Resale
Exterior Const.: Vinyl Siding
Basement Desc.: Full
Roof: Asphalt Shingle, Gable
Attic: Yes
Square Feet: 2,966
Above Ground: 2,966 Sq. Ft.
Year Built: 1865

Lot Features

Lot Size (Acres): 4.04
Zoning: R1
Lot Description: Secluded, Treed, Sloping Lot

Financial Considerations

Assessment Amount: $275,840
Tax Year: July 2024-June 2025

Disclosures and Reports

Property ID: 2291634

Listed and Sold by Berkshire Hathaway NE Prop., Sherry Borgeson

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Listing agent

— 102 Machine Shop Hill Rd —

Sherry Borgeson

Berkshire Hathaway NE Prop.

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Schools

Schools serving 102 Machine Shop Hill Rd

School District:Windham School District

Name	Grades	Distance
Windham Center School 45 North Road, Windham, CT 06280	K-5	1.9 mi
Windham Middle School 123 Quarry St., Windham, CT 06226	6-8	4 mi
Windham High School 355 High St., Windham, CT 06226	9-12	3.7 mi

Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 102 Machine Shop Hill Rd

Date

Details

Price

Change

Source

6/18/2025

Sold

$495,000

-0.98%

MLS

5/15/2025

Listed

$499,900

—

MLS

Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Total Bath
1,495
Sq. Ft.

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Total Bath
1,268
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2
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Total Bath
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Sq. Ft.

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Just Listed

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Price Reduced

-$15,000 (-2.07%)

$710,000

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Single Family
Active
Updated 5 days ago

3
Beds
3
Total Baths
2,156
Sq. Ft.

Listed by RbRE, LLC

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Price Reduced

-$205,000 (-17.08%)

$995,000

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Land Residential
Active
Updated 1 day ago

52.04
Acres

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Price Reduced

-$5,000 (-1.41%)

$349,900

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Active
Updated 4 days ago

5
Beds
4
Total Baths
2,496
Sq. Ft.

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$59,900

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Active
Updated 1 day ago

3
Beds
1
Total Bath
924
Sq. Ft.

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Sold

$485,000

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Multi-Family
Closed

9
Total Beds

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Sold by Mygoodagent

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Sold

$440,000

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Single Family
Closed

4
Beds
3
Total Baths
2,905
Sq. Ft.

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Sold

$450,000

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Single Family
Closed

3
Beds
3
Total Baths
1,691
Sq. Ft.

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Sold

$513,000

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Single Family
Closed

3
Beds
2
Total Baths
1,629
Sq. Ft.

Listed by William Raveis Real Estate
Sold by CR Premier Properties

102 Machine Shop Hill Road, Windham, CT 06266 (MLS# 24092550) is a Single Family property that was sold at $495,000 on June 18, 2025. Want to learn more about 102 Machine Shop Hill Road? Do you have questions about finding other Single Family real estate for sale in Windham? You can browse all Windham real estate or contact a Coldwell Banker agent to request more information.

102 Machine Shop Hill Rd Windham, CT 06266