For Sale
Price CutPrice Drop: $20K (10/30)
Single family home for sale at 33 Machine Shop Hl Rd, South Windham, CT 06266 | MLS# 24215433 | Listing updated on 2026-10-31
Photo 1 of Single family home for sale at 33 Machine Shop Hl Rd, South Windham, CT 06266 | MLS# 24215433 | Listing updated on 2026-10-31
Photo 2 of Single family home for sale at 33 Machine Shop Hl Rd, South Windham, CT 06266 | MLS# 24215433 | Listing updated on 2026-10-31
Photo 3 of Single family home for sale at 33 Machine Shop Hl Rd, South Windham, CT 06266 | MLS# 24215433 | Listing updated on 2026-10-31
Photo 4 of Single family home for sale at 33 Machine Shop Hl Rd, South Windham, CT 06266 | MLS# 24215433 | Listing updated on 2026-10-31
36+
Beds Icon

Street View

$499,900

Monthly Est:$2,488

  • Beds Icon4 Beds
  • Beds Icon
    4 Baths
  • Beds Icon2,548sqft

33 Machine Shop Hl Rd, South Windham, CT 06266

$2,488/moEst:

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  • Single Family Residence

  • Built in 1850

  • $-- HOA

  • 18,295.2 sqft lot

  • $196/sq.ft

Description

Looking for a home with a little extra room to spread out? This beautifully renovated single-family home offers the perfect combination of modern updates, comfort, and flexibility! One of its standout features is the additional first-floor living space, offering added privacy and versatility for a variety of lifestyle needs. This separate area features comfortable finished living space, a full bathroom, and its own laundry area, providing convenience and functionality. The bright, open-concept kitchen, dining, and living areas create a welcoming atmosphere perfect for everyday living and entertaining. A dedicated home office provides additional flexibility, while convenient main-level laundry adds even more functionality. Extensively remodeled throughout, this move-in-ready home showcases beautiful modern updates, including a new roof and new furnace, offering added value and peace of mind. Step outside to enjoy the spacious deck, perfect for relaxing or entertaining. 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 floor plan, additional first-floor living space, and impressive garage accommodations, this property offers more than meets the eye! Enjoy the comfort of single-family living with a little extra space to make your own. Schedule your private showing today!

  • Houzeo last checked: 0 minutes ago
  • Listing updated: October 31, 2026 at 8:40 pm
  • Listing Provided by: Michele Geragotelis | RE/MAX Bell Park Realty
  • Source: SMART MLS-CT | MLS#: 24215433 SMART MLS-CT

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Windham County

  • City

    South Windham

  • Neighborhood

    --

  • Year Built

    1850

  • HOA Fees

    -

  • Finished Area

    2,548 sqft

  • Lot Size

    18,295.2 sqft lot

  • Basement Area

    - sqft

  • MLS Name

    SMART MLS

  • MLS Number

    24215433

  • MLS Status

    Active

  • Days on Market

    12

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Location

HOA Management

0

HOA Fees

$-/

Disclaimer: Amenities are based on third-party information and may vary; buyers must independently verify all amenities, as information is deemed reliable but not guaranteed.

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 4

    Bathrooms: 4

Interior

  • Exterior Features

    Porch, Deck, Gutters, Lighting, Stone Wall

  • Heating

    Oil

  • Interior Features

    Open Floor Plan

  • Cooling

    Ceiling Fans

  • Appliances

    Oven/range, Microwave, Refrigerator, Dishwasher

  • Sewer

    Septic

Construction

  • Year Built

    Year Built: 1850

  • Home type

    Single Family Residence

  • Foundation Details

    Stone

  • Architectural Style

    Colonial

  • Roof

    Asphalt Shingle

Utilities & Energy

  • Laundry Features

    Main Level

  • Water Source

    Public Water Connected

  • Basement

    Full, Unfinished, Full With Walk Out

  • Parking Features

    Detached Garage

Other Features

  • Lot Features

    Lightly Wooded, Dry, Rolling

  • Subdivision Name

    N/a

Price History

DateEventPrice

10/30/2026

Source: mls_logoSMART MLS-CT #24215433

Price Decreased

$499,900 -3.85%

$196/sqft

10/19/2026

Source: mls_logoSMART MLS-CT #24215433

Listed for Sale

$519,900 -0.95%

$204/sqft

09/28/2026

Source: mls_logoSMART MLS-CT #24200058

Listing Removed

$524,900 -1.87%

$206/sqft

09/22/2026

Source: mls_logoSMART MLS-CT #24200058

Price Decreased

$534,900 -2.73%

$210/sqft

08/21/2026

Source: mls_logoSMART MLS-CT #24200058

Listed for Sale

$549,900 +243.69%

$216/sqft

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Getting Around 33 Machine Shop Hl Rd

Bike Score®

Bike Score

Somewhat Bikeable

11/100

Walk Score®

Walk Score

Car-Dependent

11/100

Data provided by Redfin

Based on information provided to and compiled by the SMART MLS, Inc. through Nov 01, 2026, 02:30AM. IDX information is provided exclusively for consumers’ personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS. ©2026 SMART MLS, Inc. All Rights Reserved.

Advertising Broker: Derek Greene | The Greene Realty Group

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