961 Middlebury Road
Middlebury, Connecticut 06762
- Beds
- 3
- Baths
- 2
- SqFt
- 2,006
- Acres
- 1.60
- Year Built
- 1979
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
Welcome to this inviting Middlebury home, beautifully situated on 1.6 private acres directly along the Greenway and across from picturesque Fenn's Pond. Offering a wonderful combination of privacy, natural beauty, and convenient living, this property is ideal for those who enjoy walking, outdoor activities, and entertaining. A long private driveway leads to the home, providing plenty of parking for family and guests. The fenced backyard features a dedicated play area, creating a wonderful outdoor space for children, pets, or simply enjoying the peaceful surroundings. Inside, the home is filled with natural light, and well-proportioned living spaces. The upper level features a spacious primary bedroom with a private full bath, along with two additional generously sized bedrooms, all with hardwood flooring. A second full bath includes both a tub and separate shower stall. The formal dining room is perfect for hosting and features hardwood flooring and a fireplace, while the oversized Great Room makes an impressive everyday gathering space with its cathedral ceiling and abundance of windows overlooking the private, natural setting. The home's open and light-filled perfect for entertaining. The eat-in kitchen features warm wood cabinetry, granite countertops, tile backsplash, and stainless-steel appliances, offering both functionality and a welcoming space for casual meals. The lower level provides additional space, laundry room, garage, and unfinished space for storage.
Key Facts
- City/Town
- Middlebury
- Neighborhood
- N/A
- Property / Style
- Single Family · Split Level
- Year Built
- 1979
- Days on Market
- 0 days
- Beds
- 3
- Baths
- 2 full
- Living Area
- 2,006 sq ft
- Lot Size
- 1.60 acres
- Garage / Parking
- 1 garage
- Property Taxes
- $7,206 / Annually
Market Snapshot
The Middlebury Market
Single Family · trailing 12 months
Active Listings
26
24 under contract
Median List Price
$665,000
26 active listings
Median Closed Price
$574,900
75 sales
Median Days on Market
42
26 active listings
Median $ / Sq Ft
$284
26 active listings
Sale-to-List Ratio
100.0%
75 sales
How this home compares
List Price
$479,900
vs $665,000 median
27.8% below median
Price / Sq Ft
$239
vs $284 median
15.8% below median
Days on Market
0 days
vs 42 days median
42 days fresher than median
Based on 26 active and 75 closed sales (trailing 12 mo) of single family in Middlebury. Source: SmartMLS · As of October 5, 2026.
Location
961 Middlebury Road, Middlebury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 1, 2026per month
- Principal & Interest$2,627
- Property Taxes$601
- Insurance$160
- 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
- Split Level
- Year Built
- 1979
- New Construction
- No/Resale
- Living Area
- 2,006 sq ft
- Below Grade
- 340 sq ft
Schools
- Elementary
- Middlebury
- Middle
- Per Board of Ed
- High
- Pomperaug
Interior
- Heating
- Hot Water
- Heat Fuel
- Oil
- Cooling
- None
- Fireplaces
- 1
- Laundry
- Lower Level
- Laundry Location
- lower level laundry room
- Appliances
- Oven/RangeMicrowaveRefrigeratorDishwasherWasherElectric Dryer
- Basement
- FullGarage Access
- In-Law Apartment
- No
- Interior Features
- Auto Garage Door OpenerCable - AvailableOpen Floor PlanSecurity System
Exterior & Lot
- Lot Size
- 1.60 acres
- Zoning
- R40
- Garage / Parking
- 1 garage spaceUnder House Garage
- Waterfront Details
- ViewSeasonal
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- Vinyl Siding
- Color
- Gray
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- SidewalkDeckGutters
- Lot Description
- Fence - PartialInterior Lot
Listing & Financials
- Property Taxes
- $7,206 / Annually
- Days on Market
- 0
- MLS #
- 24211870
- MLS Status
- Coming Soon
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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 10/5/2026. 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 10/5/2026 at 6:10 AM UTC.