323 Watertown Road
Middlebury, Connecticut 06762
- Beds
- 4
- Baths
- 2 | 1
- SqFt
- 2,067
- Acres
- 1.14
- Year Built
- 1977
- 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
Looking for a 4 bedroom home in a prime location? Here it is. This classic home sits on just over one acre of property with gorgeous gardens and a lush lawn. On the interior, a spacious updated kitchen with granite counters, an island, plenty of room for dining and wonderful storage. For easy entertaining, the living room and dining room adjoin and allow for a great flow. Enjoy a cozy family room with fireplace, oak flooring and access to a 15 x 12 deck with awning overlooking the private rear yard. In addition, there are 2.5 baths, a partially finished walk out basement and an outbuilding, perfect for storage. (Needs a bit of work.)
Key Facts
- City/Town
- Middlebury
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 1977
- Days on Market
- 0 days
- Beds
- 4
- Baths
- 2 full · 1 half
- Living Area
- 2,067 sq ft
- Lot Size
- 1.14 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $8,068 / 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
44
20 active listings
Median $ / Sq Ft
$277
20 active listings
Sale-to-List Ratio
99.8%
74 sales
How this home compares
List Price
$539,000
vs $672,000 median
19.8% below median
Price / Sq Ft
$261
vs $277 median
5.8% below median
Days on Market
0 days
vs 44 days median
44 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 29, 2026.
Location
323 Watertown Road, Middlebury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$2,748
- Property Taxes$672
- Insurance$180
- 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
- 1977
- New Construction
- No/Resale
- Living Area
- 2,067 sq ft
Schools
- Elementary
- Middlebury
- High
- Pomperaug
Interior
- Heating
- Hot Air
- Heat Fuel
- Oil
- Cooling
- Central Air
- Fireplaces
- 1
- Laundry
- Lower Level
- Appliances
- Cook TopWall OvenMicrowaveDishwasherWasherDryer
- Basement
- FullFull With Walk-Out
- Interior Features
- Auto Garage Door OpenerCable - Available
Exterior & Lot
- Lot Size
- 1.14 acres
- Zoning
- R40
- Garage / Parking
- 2 garage spacesAttached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- Aluminum
- Color
- white
- Roof
- Shingle
- Foundation
- Concrete
- Exterior Features
- ShedDeckGarden Area
- Lot Description
- Level LotProfessionally Landscaped
Listing & Financials
- Property Taxes
- $8,068 / Annually
- Days on Market
- 0
- MLS #
- 24194559
- MLS Status
- Coming Soon
Similar Properties
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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 7/29/2026. 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 7/29/2026 at 1:50 AM UTC.