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97 Westwood Drive

Middlebury, Connecticut 06762

ACTIVE - NEW$719,900
Beds
3
Baths
2 | 1
SqFt
2,415
Acres
0.82
Year Built
1974
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
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2-Car Garage1 Fireplace

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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$4,775

per 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

Homes with a close match in area, property type, and price.

Listed By

Rob Marucci

Better Living Realty, LLC

(203) 756-2520

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.