58 Shadduck Road
Middlebury, Connecticut 06762
- Beds
- 3
- Baths
- 2 | 1
- SqFt
- 2,360
- Acres
- 0.97
- Year Built
- 1934
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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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
Active Listings
26
25 under contract
Median List Price
$649,900
26 active listings
Median Closed Price
$520,000
71 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Aug 27, 2026per 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
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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 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.