106 Country Club Road
Middlebury, Connecticut 06762
- Beds
- 4
- Baths
- 2 | 1
- SqFt
- 2,664
- Acres
- 0.29
- Year Built
- 1936
- 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
Welcome to 106 Country Club Road in desirable Middlebury! This beautifully maintained and updated 4-bedroom, 2.5-bath home is exceptionally clean and move-in ready. The main level features a private in-law area complete with a bedroom, kitchenette, full bath, and separate entrance-an ideal setup for extended family, guests, or flexible living arrangements. The home offers a spacious and functional layout with an updated kitchen and plenty of comfortable living space. The finished basement provides even more room, perfect for a family room, playroom, home office, or entertaining area. Step outside and enjoy the fire pit and the newly added Trex floating deck, offering a low maintenance space to relax or entertain. With versatile living spaces, tasteful updates, and pride of ownership evident throughout, this home offers the space and flexibility to accommodate a variety of needs. Conveniently located in sought-after Middlebury, this home is ready to welcome its next owners!
Key Facts
- City/Town
- Middlebury
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 1936
- Days on Market
- 0 days
- Beds
- 4
- Baths
- 2 full · 1 half
- Living Area
- 2,664 sq ft
- Lot Size
- 0.29 acres
- Property Taxes
- $5,024 / Annually
Market Snapshot
The Middlebury Market
Single Family · trailing 12 months
Active Listings
29
24 under contract
Median List Price
$645,000
29 active listings
Median Closed Price
$522,500
74 sales
Median Days on Market
39
29 active listings
Median $ / Sq Ft
$270
29 active listings
Sale-to-List Ratio
100.0%
74 sales
How this home compares
List Price
$450,000
vs $645,000 median
30.2% below median
Price / Sq Ft
$169
vs $270 median
37.4% below median
Days on Market
0 days
vs 39 days median
39 days fresher than median
Based on 29 active and 74 closed sales (trailing 12 mo) of single family in Middlebury. Source: SmartMLS · As of September 21, 2026.
Location
106 Country Club Road, Middlebury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 17, 2026per month
- Principal & Interest$2,383
- Property Taxes$419
- Insurance$150
- 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
- 1936
- New Construction
- No/Resale
- Living Area
- 2,664 sq ft
- Below Grade
- 832 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot Water
- Heat Fuel
- Oil
- Cooling
- Window Unit
- Laundry Location
- lower level
- Appliances
- Oven/RangeMicrowaveRefrigeratorDishwasherWasherDryer
- Basement
- FullFully Finished
Exterior & Lot
- Lot Size
- 0.29 acres
- Zoning
- R40
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- Vinyl Siding
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Lot Description
- TreedLevel Lot
Listing & Financials
- Property Taxes
- $5,024 / Annually
- Days on Market
- 0
- MLS #
- 24208639
- 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 9/21/2026. 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 9/21/2026 at 7:00 PM UTC.