413 Watertown Road
Middlebury, Connecticut 06762
- Beds
- 4
- Baths
- 2 | 1
- SqFt
- 2,251
- Acres
- 0.69
- Year Built
- 1932
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
Character, charm, and exceptional flexibility come together in this one-of-a-kind Middlebury home. Offering far more space than meets the eye, this property blends timeless craftsmanship with a versatile layout designed to fit today's evolving lifestyle. The main home features expansive living and dining spaces, a full bath, a main-level bedroom, and an additional flexible-use room ideal for a home office, den, guest space, or hobby room. Upstairs, you'll find two generously sized bedrooms with abundant closet space and a convenient half bath. A standout feature is the potential in-law setup, complete with its own living area, bedroom, and full bath, providing endless possibilities for multi-generational living, extended guests, or added privacy. Throughout the home, you'll appreciate the details that make this property truly special-from beautiful built-ins and custom trim work to the character and craftsmanship rarely found today. Outside, enjoy a spacious backyard designed for both relaxation and entertaining, featuring a large above-ground pool with surrounding deck space, perfect for summer gatherings and enjoying the outdoors. The lower level offers additional storage, garage space, and a workshop area complete with a workbench, ideal for hobbyists, craftsmen, or anyone in need of extra room. This is not your average Cape-style home. With its generous living space, unique layout, and endless possibilities, this home it ready for its next chapter!
Key Facts
- City/Town
- Middlebury
- Neighborhood
- N/A
- Property / Style
- Single Family · Cape Cod
- Year Built
- 1932
- Days on Market
- 34 days
- Beds
- 4
- Baths
- 2 full · 1 half
- Living Area
- 2,251 sq ft
- Lot Size
- 0.69 acres
- Garage / Parking
- 1 garage
- Property Taxes
- $7,613 / 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
$485,000
vs $672,000 median
27.8% below median
Price / Sq Ft
$215
vs $277 median
22.4% below median
Days on Market
34 days
vs 43 days median
9 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
413 Watertown Road, Middlebury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$2,473
- Property Taxes$634
- Insurance$162
- 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
- 1932
- New Construction
- No/Resale
- Living Area
- 2,251 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Radiator
- Heat Fuel
- Oil
- Cooling
- Ceiling FansWindow Unit
- Fireplaces
- 1
- Laundry
- Lower Level
- Appliances
- Electric RangeRefrigeratorWasherDryer
- Basement
- FullStorageGarage Access
- In-Law Apartment
- PossibleFirst FloorSeparate Entry
- Additional Rooms
- Breezeway
Exterior & Lot
- Lot Size
- 0.69 acres
- Zoning
- R40
- Garage / Parking
- 1 garage spaceTandemUnder House Garage
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Pool
- Above Ground Pool
- Construction
- Vinyl Siding
- Roof
- Asphalt Shingle
- Foundation
- ConcreteStone
- Exterior Features
- BreezewayShedDeck
- Lot Description
- Interior Lot
Listing & Financials
- Property Taxes
- $7,613 / Annually
- Days on Market
- 34
- MLS #
- 24185992
- MLS Status
- Under Contract
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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 5:25 AM UTC.