66 Artillery Road
Middlebury, Connecticut 06762
- Beds
- 4
- Baths
- 3 | 1
- SqFt
- 2,691
- Acres
- 1.02
- Year Built
- 1804
- 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
Circa 1803 "Todt Farm," is a historically significant center hall Colonial set on 1.06 picturesque acres overlooking and adjacent to Fenn Pond. This 11-room home offers 2,691 sq ft with 4 bedrooms and 3.1 baths. Rich with authentic vintage details including wide board floors, 7 fireplaces, horizontal board paneling, built-ins, and classic 12-over-12 windows and front and rear stairwells. The charming sunroom opens to a stone patio, ideal for enjoying the serene setting of mature trees, gardens, stone walls and rolling and level lawns. The property is surrounded by Middlebury Land Trust land, including the preserved Brookdale farm across the street. Additional features include an attached 2-bay garage and a 20kW Generac generator.Pool is being sold "as-is." Middlebury offers an extensive variety of outdoor enjoyment such as the Middlebury Rec Area, Quassy Amusement Park, Lake Quassapaug, the 4.5 paved Greenway walking trail, Meadowview Park and the John Largay Preserve. Come take a look!
Key Facts
- City/Town
- Middlebury
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial,Antique
- Year Built
- 1804
- Days on Market
- 106 days
- Beds
- 4
- Baths
- 3 full · 1 half
- Living Area
- 2,691 sq ft
- Lot Size
- 1.02 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $7,850 / 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
$585,000
vs $672,000 median
12.9% below median
Price / Sq Ft
$217
vs $277 median
21.7% below median
Days on Market
106 days
vs 43 days median
63 days longer 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
66 Artillery Road, Middlebury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$2,983
- Property Taxes$654
- Insurance$195
- 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,Antique
- Year Built
- 1804
- New Construction
- No/Resale
- Living Area
- 2,691 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Pomperaug
Interior
- Heating
- Hot Water
- Heat Fuel
- Oil
- Cooling
- None
- Fireplaces
- 7
- Laundry
- Main Level
- Laundry Location
- Between Kitchen and Garage
- Appliances
- Oven/RangeMicrowaveRefrigeratorDishwasherWasherDryer
- Basement
- FullFull With Hatchway
- Interior Features
- Auto Garage Door Opener
- Additional Rooms
- FoyerLaundry Room
Exterior & Lot
- Lot Size
- 1.02 acres
- Zoning
- R40
- Garage / Parking
- 2 garage spacesAttached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Public Sewer Connected
- Flood Zone
- No
- Pool
- In Ground Pool
- Construction
- Clapboard
- Roof
- Asphalt Shingle
- Foundation
- Stone
- Exterior Features
- Stone WallPatio
- Lot Description
- Open Lot
Listing & Financials
- Property Taxes
- $7,850 / Annually
- Days on Market
- 106
- MLS #
- 24164662
- MLS Status
- Under Contract
Similar Properties
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Co-Listed By
Claudine McHugh
Klemm Real Estate Inc
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 7:55 AM UTC.