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58 Shadduck Road

Middlebury, Connecticut 06762

COMING SOON - NEW$599,900
Beds
3
Baths
2 | 1
SqFt
2,360
Acres
0.97
Year Built
1934
Matt Caiola

Matt Caiola

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3-Car Garage

About This Home

Welcome to 58 Shadduck Road, a renovated Colonial in one of Middlebury's most desirable locations. This move-in-ready home seamlessly blends timeless charm with modern updates, featuring gleaming hardwood floors and a bright open-concept layout. The main level offers a spacious living room with sliders to a large patio, a dining room, a sun-filled kitchen with center island, and a versatile office or sitting area. The second-floor primary suite serves as a private retreat with a luxurious en-suite bath and walk-in closet. Two additional bedrooms and a full bath complete the upper level. Extensive improvements include a newer roof, windows, siding, driveway, electrical, plumbing, central air, propane heating, generator-ready setup, and updated mechanicals. The full basement provides abundant storage. A rare highlight is the detached 3-car garage, offering endless possibilities for car enthusiasts, hobbyists, or additional living space. With its generous footprint and utilities, it presents an excellent opportunity for a future in-law suite, guest quarters, home office, or workshop. A newer storage shed provides additional space. Situated on a picturesque, level lot bordered by mature trees and a charming brook, the property features a private patio perfect for entertaining. Conveniently located just minutes from Middlebury's town center, shopping, restaurants, major highways, and Routes 8 and I-84, this exceptional home combines privacy, flexibility, and convenience.

Key Facts

City/Town
Middlebury
Neighborhood
N/A
Property / Style
Single Family · Colonial
Year Built
1934
Days on Market
0 days
Beds
3
Baths
2 full · 1 half
Living Area
2,360 sq ft
Lot Size
0.97 acres
Garage / Parking
3 garage
Property Taxes
$5,606 / Annually

Market Snapshot

The Middlebury Market

Single Family · trailing 12 months

Median Days on Market

45

26 active listings

Median $ / Sq Ft

$276

26 active listings

Sale-to-List Ratio

100.0%

71 sales

How this home compares

List Price

$599,900

vs $649,900 median

7.7% below median

Price / Sq Ft

$254

vs $276 median

8.0% below median

Days on Market

0 days

vs 45 days median

45 days fresher than median

Based on 26 active and 71 closed sales (trailing 12 mo) of single family in Middlebury. Source: SmartMLS · As of September 3, 2026.

Location

58 Shadduck Road, Middlebury, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$3,751

per month

  • Principal & Interest$3,084
  • Property Taxes$467
  • Insurance$200
  • 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
Colonial
Year Built
1934
New Construction
No/Resale
Living Area
2,360 sq ft
Below Grade
616 sq ft

Schools

Elementary
Per Board of Ed
High
Per Board of Ed

Interior

Heating
Hydro Air
Heat Fuel
Propane
Cooling
Ceiling FansCentral Air
Laundry
Main Level
Appliances
Electric RangeRefrigeratorWasherElectric Dryer
Basement
FullConcrete FloorFull With Hatchway
In-Law Apartment
YesFirst Floor
Interior Features
Auto Garage Door OpenerCable - Pre-wired

Exterior & Lot

Lot Size
0.97 acres
Zoning
R40
Garage / Parking
3 garage spacesDetached Garage
Waterfront Details
Not Applicable
Water Source
Private Well
Sewer
Public Sewer Connected
Flood Zone
No
Construction
Vinyl Siding
Roof
Asphalt Shingle
Foundation
Stone
Exterior Features
ShedPatio
Lot Description
Lightly WoodedTreedLevel LotWater ViewOpen Lot

Listing & Financials

Property Taxes
$5,606 / Annually
Days on Market
0
MLS #
24203901
MLS Status
Coming Soon

Similar Properties

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Listed By

David Smith

(860) 480-3474

Showcase Realty, Inc.

(860) 274-7000

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 9/3/2026. 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 9/3/2026 at 1:10 AM UTC.