10 Old Waterbury Road
Middlebury, Connecticut 06762
- Beds
- 5
- Baths
- 4
- SqFt
- 2,345
- Acres
- 0.41
- Year Built
- 1930
- Property Type
- 4 Family
Matt Caiola
Luxury Real Estate Advisor
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About This Home
Middlebury Multi-Family-RARE FIND! 4 units! Two buildings on one (.41 acre) parcel. Situated on "park like" grounds at end of cul-de-sac with IN GROUND SWIMMING POOL, and two car detached garage. Commuter friendly with easy access to Rt 8 & I-84, and only moments away to Post University and NVCC. 1st building consists of a side by side TRI-PLEX w/garage under and fireplaced L/R's. 2nd building consists of an adorable, detached single-family RANCH STYLE house-3 rooms/1 bedroom w/oversize fireplace living room & oil heat. Separate heat and utilities. Public water & sewer. Enjoy Middlebury's Greenway trails, hop brook lake for swimming, picniking, hiking, biking and so much more-all within walking distance! Highly sought after, Middlebury is "top rated" for it's schools and low rental vacancy. Perfect opportunity for OWNER OCCUPANT to live in one unit and collect rent from other 3 units towards your mortgage payment. INVESTORS...here is your chance to add this one to your portfolio!. Start to grow "SWEET EQUITY"!
Key Facts
- City/Town
- Middlebury
- Property / Style
- Multi-Family · Units are Side-by-Side
- Year Built
- 1930
- Days on Market
- 0 days
- Beds
- 5
- Baths
- 4 full
- Living Area
- 2,345 sq ft
- Lot Size
- 0.41 acres
- Garage / Parking
- 3 garage
- Property Taxes
- $7,675 / Annually
Market Snapshot
The Middlebury Market
Multi-Family · trailing 12 months
Active Listings
1
Middlebury inventory
Median List Price
$699,900
1 active listing
Median Closed Price
$465,000
1 sale
Median Days on Market
0
1 active listing
Median $ / Sq Ft
$298
1 active listing
Sale-to-List Ratio
88.6%
1 sale
How this home compares
List Price
$699,900
vs $699,900 median
In line with median
Price / Sq Ft
$298
vs $298 median
In line with median
Days on Market
--
vs 0 days median
Limited comparable data
Based on 1 active and 1 closed sales (trailing 12 mo) of multi-family in Middlebury. Source: SmartMLS · As of September 16, 2026.
Location
10 Old Waterbury Road, Middlebury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 10, 2026per month
- Principal & Interest$3,635
- Property Taxes$640
- Insurance$233
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Middlebury
- County
- New Haven
Residence
- Property Type
- Multi-Family
- Subtype
- Quadruplex
- Style
- Units are Side-by-Side
- Year Built
- 1930
- New Construction
- No/Resale
- Living Area
- 2,345 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Baseboard
- Heat Fuel
- ElectricOil
- Cooling
- None
- Fireplaces
- 3
- Basement
- Partial
Exterior & Lot
- Lot Size
- 0.41 acres
- Zoning
- R40
- Garage / Parking
- 3 garage spacesDetached GarageUnder House Garage
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Pool
- In Ground Pool
- Construction
- Vinyl Siding
- Color
- Grey
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- SidewalkPorchDeckGuttersGarden AreaLighting
- Lot Description
- Lightly WoodedSloping Lot
Listing & Financials
- Property Taxes
- $7,675 / Annually
- Days on Market
- 0
- MLS #
- 24207437
- MLS Status
- Active
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 9/16/2026. 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 9/16/2026 at 5:05 AM UTC.