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!
Under contract
$525,000
541 Benson Road, Middlebury, CT 06762
3beds
1,600sqft
Est.:
Multi Family
Built in 1942
-- sqft lot
$-- Zestimate®
$328/sqft
$-- HOA
What's special
Separate soaking tubBrand-new spa-like bathroomCentral airHigh-end finishesPrivate primary suite retreatClassic new england stonewallsOak cabinets
- 40 days |
- 852 |
- 43 |
Likely to sell faster than
Zillow last checked:
Listing updated:
Listed by:
Joseph Martino joe@joemartinore.com,
Joseph Martino Real Estate 203-671-2384
Source: Smart MLS,MLS#: 24161555
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 3
- Full bathrooms: 3
Heating
- Baseboard, Bottle Gas, Oil
Cooling
- Central Air
Appliances
- Included: Water Heater
Features
- Basement: Full
- Attic: Finished,Walk-up
- Has fireplace: No
Interior area
- Total structure area: 1,600
- Total interior livable area: 1,600 sqft
- Finished area above ground: 1,600
Property
Parking
- Total spaces: 3
- Parking features: Attached
- Attached garage spaces: 3
Lot
- Size: 0.8 Acres
- Features: Sloped
Details
- Parcel number: 1192162
- Zoning: L200
Construction
Type & style
- Home type: MultiFamily
- Architectural style: Other
- Property subtype: Multi Family
Materials
- Vinyl Siding, Cedar
- Foundation: Concrete Perimeter, Masonry
- Roof: Asphalt
Condition
- New construction: No
- Year built: 1942
Utilities & green energy
- Sewer: Septic Tank
- Water: Well
Community & HOA
HOA
- Has HOA: No
Location
- Region: Middlebury
Financial & listing details
- Price per square foot: $328/sqft
- Tax assessed value: $309,000
- Annual tax amount: $10,049
- Date on market: 3/23/2026
Estimated market value
Not available
Estimated sales range
Not available
$3,509/mo
Price history
| Date | Event | Price |
|---|---|---|
| 4/17/2026 | Pending sale | $525,000$328/sqft |
Source: | ||
| 3/23/2026 | Listed for sale | $525,000+5.2%$328/sqft |
Source: | ||
| 1/29/2026 | Listing removed | $499,000$312/sqft |
Source: | ||
| 12/26/2025 | Price change | $499,000-14%$312/sqft |
Source: | ||
| 9/19/2025 | Listed for sale | $579,900+96.6%$362/sqft |
Source: | ||
| 3/24/2021 | Listing removed | -- |
Source: Owner Report a problem | ||
| 11/24/2016 | Listing removed | $295,000$184/sqft |
Source: Owner Report a problem | ||
| 8/26/2016 | Listed for sale | $295,000+20.4%$184/sqft |
Source: Owner Report a problem | ||
| 2/16/2007 | Sold | $245,000$153/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $10,049 -0.2% | $309,000 |
| 2024 | $10,073 +1.1% | $309,000 |
| 2023 | $9,968 +3.2% | $309,000 |
| 2022 | $9,659 +18.7% | $309,000 +32.3% |
| 2021 | $8,136 -0.8% | $233,600 |
| 2020 | $8,199 +5.1% | $233,600 |
| 2019 | $7,802 +2.7% | $233,600 |
| 2018 | $7,594 +3.2% | $233,600 |
| 2017 | $7,356 +1.4% | $233,600 -3% |
| 2015 | $7,253 +2.7% | $240,800 |
| 2014 | $7,065 +1.7% | $240,800 |
| 2013 | $6,949 +2.8% | $240,800 |
| 2012 | $6,759 +3.3% | $240,800 -12.4% |
| 2011 | $6,540 +43.8% | $274,900 +42.8% |
| 2009 | $4,549 +1.8% | $192,500 |
| 2008 | $4,468 +6% | $192,500 |
| 2007 | $4,216 +18% | $192,500 +64.6% |
| 2005 | $3,573 -0.9% | $116,950 |
| 2004 | $3,604 +8.2% | $116,950 0% |
| 2003 | $3,332 +17.8% | $117,000 +32.6% |
| 2000 | $2,828 | $88,250 |
Find assessor info on the county website
Monthly payment
Est. payment
$3,524/mo
Principal & interest
$2592
Property taxes
$932
More affordability tools
Climate risks
Neighborhood: 06762
Nearby schools
GreatSchools rating
- 5/10Long Meadow Elementary SchoolGrades: PK-5Distance: 1.1 mi
- 7/10Memorial Middle SchoolGrades: 6-8Distance: 4.6 mi
- 8/10Pomperaug Regional High SchoolGrades: 9-12Distance: 1.1 mi
A local agent can set up tours, give advice and negotiate with sellers.
A local lender can help you make sure your offer is ready when you are.
- Connecticut
- New Haven County
- Middlebury
- 06762
- 541 Benson Road





