566 Benson Road
Middlebury, Connecticut 06762
- Beds
- 4
- Baths
- 2 | 1
- SqFt
- 2,020
- Acres
- 2.48
- Year Built
- 1978
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
About This Home
Before you enter this charming oversized cape, take a look beyond the covered deck at 2.5 parklike acres that just happen to sit adjacent to 19 acres of Middlebury Land Trust. Imagine yourself relaxing there ... and then enter the house. The kitchen was remodeled with white cabinets, matching appliances, and Corian countertops that have a drainboard scored into the top by the sink, and a metal trivet next to the stove that allows you to put hot pots & pans on the counter without damaging it. Between the dining and living rooms is a fireplace with a propane insert to supplement the hot water baseboard heat. Mini splits provide a/c as well as an additional heat source for the first floor. The town card says 4 bedrooms, but a small room on the main level, currently used as a laundry room offers many options to fit your needs. The first floor includes a primary with a walk-in closet, and full bath with a jetted tub/shower, plus a 2nd bedroom currently used as a music room. Upstairs, 2 huge bedrooms with built-ins, large closets, & storage in the eaves are separated by a generously sized landing for max privacy, and share the 2nd full bath with its updated Fiberglass surround tub/shower and a skylight that provides natural light no matter the time of day. A full basement provides access to the 2 car garage, and lots of storage. Schedule your showing and come fall in love with this well loved and well maintained home in Middlebury.
Key Facts
- City/Town
- Middlebury
- Neighborhood
- N/A
- Property / Style
- Single Family · Cape Cod
- Year Built
- 1978
- Days on Market
- 37 days
- Beds
- 4
- Baths
- 2 full · 1 half
- Living Area
- 2,020 sq ft
- Lot Size
- 2.48 acres
- Garage / Parking
- 2 garage · 6 total
- Property Taxes
- $8,793 / Annually
Market Snapshot
The Middlebury Market
Single Family · trailing 12 months
Active Listings
20
19 under contract
Median List Price
$672,000
20 active listings
Median Closed Price
$522,500
74 sales
Median Days on Market
43
20 active listings
Median $ / Sq Ft
$277
20 active listings
Sale-to-List Ratio
99.8%
74 sales
How this home compares
List Price
$480,000
vs $672,000 median
28.6% below median
Price / Sq Ft
$238
vs $277 median
14.1% below median
Days on Market
37 days
vs 43 days median
6 days fresher than median
Based on 20 active and 74 closed sales (trailing 12 mo) of single family in Middlebury. Source: SmartMLS · As of July 28, 2026.
Location
566 Benson Road, Middlebury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$2,447
- Property Taxes$733
- Insurance$160
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Middlebury
- Neighborhood
- N/A
- County
- New Haven
Residence
- Property Type
- Single Family
- Style
- Cape Cod
- Year Built
- 1978
- New Construction
- No/Resale
- Living Area
- 2,020 sq ft
Schools
- Elementary
- Long Meadow
- High
- Pomperaug
Interior
- Heating
- Hot Water
- Heat Fuel
- Oil
- Cooling
- Heat PumpSplit SystemWindow Unit
- Fireplaces
- 1
- Laundry
- Main Level
- Laundry Location
- Main level by bedrooms
- Appliances
- Gas RangeMicrowaveRange HoodRefrigeratorDishwasherWasherElectric Dryer
- Basement
- FullUnfinishedStorageGarage AccessInterior AccessConcrete Floor
- Interior Features
- Auto Garage Door OpenerCable - Pre-wired
- Additional Rooms
- Laundry Room
Exterior & Lot
- Lot Size
- 2.48 acres
- Zoning
- R40
- Garage / Parking
- 2 garage spaces6 total parking spacesUnder House GaragePavedOff Street ParkingDrivewayPrivateAsphalt
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Septic
- Construction
- Vinyl Siding
- Color
- Yellow
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- ShedFruit TreesGuttersGarden AreaCovered DeckStone Wall
- Lot Description
- Borders Open SpaceDryLevel LotCleared
Listing & Financials
- Property Taxes
- $8,793 / Annually
- Days on Market
- 37
- MLS #
- 24185547
- MLS Status
- Under Contract
- Financing
- FHA,VA,CHFA
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 7/28/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.
Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.
Data last updated on 7/28/2026 at 7:01 AM UTC.