97 Westwood Drive
Middlebury, Connecticut 06762
- Beds
- 3
- Baths
- 2 | 1
- SqFt
- 2,415
- Acres
- 0.82
- Year Built
- 1974
- 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 this stunning, completely updated home located in one of Middlebury's highly desirable neighborhoods! Offering 3 bedrooms and 2.5 bathrooms, this exceptional property showcases high-end finishes, quality craftsmanship, and thoughtful upgrades throughout. No detail has been overlooked in creating a home that perfectly blends luxury, comfort, and modern convenience. Step inside to discover beautiful hardwood floors, custom built-in closets, and an inviting propane fireplace that adds warmth and elegance. The impressive list of improvements includes a new roof (2021), updated plumbing and HVAC systems (2021), central air conditioning (2021), and enhanced spray foam insulation for improved energy efficiency. A whole-house generator provides additional peace of mind, while smart thermostats and a security system offer modern convenience. The beautifully finished lower level takes this home to another level, featuring luxurious heated floors and a temperature-controlled wine cellar, perfect for wine enthusiasts and entertaining. Outside, enjoy professionally landscaped grounds, an elegant paver walkway, and a beautiful paver patio ideal for outdoor gatherings or quiet relaxation. Additional highlights include city water, city sewer, and a prime location offering convenient access to major highways, restaurants, local vineyards, and Middlebury's highly regarded schools. Truly move-in ready!!
Key Facts
- City/Town
- Middlebury
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 1974
- Days on Market
- 0 days
- Beds
- 3
- Baths
- 2 full · 1 half
- Living Area
- 2,415 sq ft
- Lot Size
- 0.82 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $7,613 / Annually
Market Snapshot
The Middlebury Market
Single Family · trailing 12 months
Active Listings
25
16 under contract
Median List Price
$725,000
25 active listings
Median Closed Price
$557,450
86 sales
Median Days on Market
64
25 active listings
Median $ / Sq Ft
$273
25 active listings
Sale-to-List Ratio
100.0%
86 sales
How this home compares
List Price
$719,900
vs $725,000 median
In line with median
Price / Sq Ft
$298
vs $273 median
9.2% above median
Days on Market
0 days
vs 64 days median
64 days fresher than median
Based on 25 active and 86 closed sales (trailing 12 mo) of single family in Middlebury. Source: SmartMLS · As of November 11, 2026.
Location
97 Westwood Drive, Middlebury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Nov 5, 2026per month
- Principal & Interest$3,901
- Property Taxes$634
- Insurance$240
- 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
- 1974
- New Construction
- No/Resale
- Living Area
- 2,415 sq ft
- Below Grade
- 367 sq ft
Schools
- Elementary
- Middlebury
- High
- Pomperaug
Interior
- Heating
- Hot Air
- Heat Fuel
- Propane
- Cooling
- Central Air
- Fireplaces
- 1
- Appliances
- Gas RangeMicrowaveRefrigeratorDishwasher
- Basement
- FullPartially Finished
- Interior Features
- Auto Garage Door Opener
Exterior & Lot
- Lot Size
- 0.82 acres
- Zoning
- R40
- Garage / Parking
- 2 garage spacesAttached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- Aluminum
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Lot Description
- Cleared
Listing & Financials
- Property Taxes
- $7,613 / Annually
- Days on Market
- 0
- MLS #
- 24220528
- MLS Status
- Active
- Financing
- FHA,VA,CHFA
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 11/11/2026. 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 11/11/2026 at 6:16 PM UTC.