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541 Benson Road

Middlebury, CT 06762
  • $525,000
  • STATUS: Active Under Contract
  • ON SITE: 56 Days
  • MLS #: 24161555
Under Contract
UPDATED: 35 min ago
$525,000
  • 3
    BEDS
  • 0.8
    ACRES
  • 3
    BATHS
  • 0
    1/2 BATHS
  • 1,600
    SQFT
  • $328
    $/SQFT
Type:
Multi-Family
Built:
1942
County:
Area:

School Information

Elementary School:
High School:

Description

Rare Two-Home Compound in Middlebury - Ideal for Investment or Owner-Occupant! An extraordinary opportunity for investors or owner-occupants looking to offset their mortgage! This unique property at 541 Benson Road features TWO distinct, detached dwellings on a private .8-acre lot, offering a total of 3 bedrooms, 3 full baths, and 4 garage bays. Unit 1: The Main Residence (2BR/2BA) This beautifully appointed home features an open-concept layout with gleaming hardwood floors and high-end finishes. Chef's Kitchen: U-shaped layout with oak cabinets, granite countertops, stainless steel appliances (gas stove), and a large pantry. Main Level: Includes a spacious bedroom and a brand-new spa-like bathroom with a custom tiled walk-in shower and separate soaking tub. Upper Level: A private primary suite retreat finished in warm natural pine, featuring abundant closet space, a full ensuite bath, and a charming built-in reading nook/office area. Central Air, pellet stove for efficient heating, and a massive 3-car attached garage for ample storage or workshop space. Unit 2: Detached Carriage House (1BR/1BA) A completely separate, legal-style dwelling perfect for rental income, multi-generational living, or a professional home office. Living Space: Features a functional galley kitchen with gas cooking, a bright living area, and a private bedroom. Amenities: Full bathroom with a tiled shower and its own dedicated 1-car garage/workshop located directly be Exterior & Location The property sits on a lush .8-acre "private oasis" framed by classic New England stonewalls and a brick patio. Whether you are looking for a high-end rental property or a way to live in one home while the other pays your taxes, this versatile compound is a rare find in Middlebury. Total Garage Bays: 4 | Total Acreage: 0.80 | Separate Utilities Schedule your private tour today to explore the unmatched flexibility of this two-family setup!

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The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc. Data last updated: 2026-05-19T09:10:03.443.
www.timdentteam.com/homes/174351745
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541 Benson Road Middlebury, CT 06762

  • Price: $525,000
  • Status: Active Under Contract
  • On Site: 56 Days
  • Updated: 35 min ago
  • MLS #: 24161555
3
Beds
3
Baths
0
½ Baths
0.8
Acres
1,600
SQFT
$328
$/SQFT
1942
Built
County:
New Haven
Area:
Middlebury
Elementary School:
per board of ed
High School:
per board of ed
Property Description
Rare Two-Home Compound in Middlebury - Ideal for Investment or Owner-Occupant! An extraordinary opportunity for investors or owner-occupants looking to offset their mortgage! This unique property at 541 Benson Road features TWO distinct, detached dwellings on a private .8-acre lot, offering a total of 3 bedrooms, 3 full baths, and 4 garage bays. Unit 1: The Main Residence (2BR/2BA) This beautifully appointed home features an open-concept layout with gleaming hardwood floors and high-end finishes. Chef's Kitchen: U-shaped layout with oak cabinets, granite countertops, stainless steel appliances (gas stove), and a large pantry. Main Level: Includes a spacious bedroom and a brand-new spa-like bathroom with a custom tiled walk-in shower and separate soaking tub. Upper Level: A private primary suite retreat finished in warm natural pine, featuring abundant closet space, a full ensuite bath, and a charming built-in reading nook/office area. Central Air, pellet stove for efficient heating, and a massive 3-car attached garage for ample storage or workshop space. Unit 2: Detached Carriage House (1BR/1BA) A completely separate, legal-style dwelling perfect for rental income, multi-generational living, or a professional home office. Living Space: Features a functional galley kitchen with gas cooking, a bright living area, and a private bedroom. Amenities: Full bathroom with a tiled shower and its own dedicated 1-car garage/workshop located directly be Exterior & Location The property sits on a lush .8-acre "private oasis" framed by classic New England stonewalls and a brick patio. Whether you are looking for a high-end rental property or a way to live in one home while the other pays your taxes, this versatile compound is a rare find in Middlebury. Total Garage Bays: 4 | Total Acreage: 0.80 | Separate Utilities Schedule your private tour today to explore the unmatched flexibility of this two-family setup!
Exterior Features

Direct Waterfront YN No Exterior Siding Vinyl SidingCedar Garage And Parking Under House Garage Lot Description Sloping Lot Roof Information Asphalt Shingle Style Other Swimming Pool YN No Waterfront Description Not Applicable

Interior Features

Attic Description FinishedWalk-up Attic YN Yes Basement Description Full Cooling System Central Air Fireplaces Total 0 Heat Type Baseboard Laundry Room Location basement Living Area SQFTPer Public Record 0 Sq Ft Est Heated Above Grade 1600 Total Rooms 5 Total Rooms Multi Family 5

Property Features

Agent Owner YN No Bank Owned Property No Foundation Type ConcreteMasonry Fuel Tank Location Above Ground Heat Fuel Type Bottle GasOil Home Owners Assocation No Hot Water Description OilPropaneTank Size Unknown New Construction Type No/Resale Potential Short Sale No Property Sub Type 2 Family Sewage System Septic Tax Year July 2025-June 2026 Total Number Of Units 2 Under Agreement Yn No Water Source Private Well Zoning L200

Listing information © 2026 Smart MLS
Listing provided courtesy of Joseph Martino of Joseph Martino Real Estate: .


The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc. Data last updated: 2026-05-19T09:10:03.443.
 
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