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566 Benson Road

Middlebury, Connecticut 06762

PENDING$480,000
Beds
4
Baths
2 | 1
SqFt
2,020
Acres
2.48
Year Built
1978
Matt Caiola

Matt Caiola

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2-Car Garage1 Fireplace

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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$3,340

per 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

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Ruth Zeiss

(347) 556-0014

William Raveis Real Estate

(203) 264-8180

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.