MAIN HOUSE (2BR/2BA): Features an open-concept layout w/ gleaming hardwood floors. The updated kitchen is a chef's delight, boasting granite countertops, stainless steel appliances, a gas stove & pantry. The main level includes a bedroom & a NEW spa-like full bath w/ a custom tiled walk-in shower & separate soaking tub. Upstairs is a private primary suite retreat, wrapped in warm pine woodwork, offering abundant closet space & its own full bath. A charming reading nook w/ built-ins completes the second floor. Plus Central A/C & 3-car garage. GUEST HOUSE: This separate, detached dwelling offers a 1BR/1BA layout with a full kitchen, living area & a private 1-car garage/workshop below. The property is a private oasis with a brick patio & classic New England stonewalls, perfect for gardening or relaxing. With 4 total garage bays and unmatched flexibility, this unique property is a must-see. Schedule your tour today!
An extraordinary opportunity awaits at this unique property, featuring TWO distinct homes situated on a private .8-acre lot. This is the perfect solution for multi-generational living, a guest house, a home office, or generating rental income! The MAIN HOUSE is a beautifully appointed 2-bedroom, 2-full-bath residence designed for modern comfort. Step inside to an open-concept living and dining area with gleaming hardwood floors, flowing seamlessly into a stunning U-shaped kitchen. The chef in your family will love the oak cabinets, granite countertops, stainless steel appliances (including a gas stove, large refrigerator, and dishwasher), tile flooring, double sink, and spacious pantry. The main level also features a convenient bedroom and a brand new, spa-like full bathroom complete with a custom tiled walk-in shower and a separate deep soaking tub. Ascend the stairs to your private primary suite retreat. This expansive bedroom is wrapped in beautiful natural pine woodwork, offering abundant closet space and its own full bathroom. A charming built-in seating area with shelving at the top of the stairs provides the perfect reading nook or office space. Additional features include Central Air, oil boiler, pellet stove, and an oversized 3-car garage under the home. The separate, detached GUEST HOUSE offers incredible flexibility. This charming dwelling includes a galley kitchen with a gas stove and built-in microwave, a living area, a private bedroom, and a full bathroom with a tiled shower. Below, a 1-car garage provides ample space for a vehicle, workshop, or extra storage. Outside, your private oasis awaits. The expansive .8-acre lot is adorned with classic New England stonewalls and a lovely brick patio, offering endless possibilities for gardening, entertaining, and relaxation. With a total of 4 garage bays and two completely separate living spaces, this one-of-a-kind property is a rare find and will not last long. Schedule your private showing today to experience all it has to offer!
Single-familyProperty Type
1942Year Built
0.8 acresLot Size
$291Price/Sq.Ft.
3 car garageParking
Listed by Joseph Martino• Joseph Martino Real Estate
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!
Smart MLS #24161553
Jun 17, 2026
Sold
$465,000
$291/sq ft
Apr 17, 2026
Pending
—
Mar 23, 2026
Listed
$525,000
$328/sq ft
Smart MLS #24128030
Jan 29, 2026
Listing Removed
—
Dec 26, 2025
Price Changed
$499,000
$312/sq ft
Sep 19, 2025
Listed
$579,900
$362/sq ft
Public Records
Feb 16, 2007
Sold
$245,000
$153/sq ft
Smart MLS #98302527
Dec 30, 2006
Listing Removed
—
Sep 21, 2006
Listed
$289,900
$181/sq ft
Year
Property tax
Land + Additions
Assessment*
2022
$9,659 (+18.7%)
$65,800 + $243,200
$309,000
2021
$8,136 (−0.8%)
$74,900 + $158,700
$233,600
2020
$8,199 (+5.1%)
$74,900 + $158,700
$233,600
2019
$7,802 (+2.7%)
$74,900 + $158,700
$233,600
2018
$7,594 (+3.2%)
$74,900 + $158,700
$233,600
2017
$7,356 (−1.5%)
$74,900 + $158,700
$233,600
2016
$7,467 (+5.7%)
$88,200 + $152,600
$240,800
2014
$7,065 (+1.7%)
$88,200 + $152,600
$240,800
2011
$6,949
$88,200 + $152,600
$240,800
Public record
Beds
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Baths
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Stories
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Lot width
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Lot depth
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Lot size
0.8 Acres
Year renovated
—
Sq. Ft.
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Year built
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Style
Other
County
New Haven County
APN
1192162
Parking Spaces
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Basement
—
Accessible
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HOA Dues
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Garage
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Features
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Last updated by owner on Jul 13, 2023.
Property details
Parking
Garage Information
Garage & Parking: Under House Garage
Garages Number: 3
Interior
Interior Information
Total Rooms: 4
Laundry Room Location: Basement (washer dryer to stay)
Laundry Room Info: Lower Level
In-Law Apartment: Yes
In-Law Access: Detached, Separate Entry
Cooling System: Ceiling Fans, Central Air
Appliances Included: Gas Range, Refrigerator, Dishwasher, Washer, Dryer