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2 Northwood Drive

Middlebury, Connecticut 06762

ACTIVE$575,000
Beds
3
Baths
3
SqFt
1,252
Acres
0.42
Year Built
1962
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
Higgins Group Private Brokerage

Request a private showing and get Matt's read on price, condition, and next steps.

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2-Car Garage2 Fireplaces

About This Home

Tucked into Middlebury's desirable Three Mile Hill neighborhood, this beautifully maintained split-level blends everyday comfort with tasteful, modern updates throughout. A welcoming foyer opens to an expansive, light-filled living room anchored by one of the home's two floor-to-ceiling fireplaces - a warm focal point for gatherings large and small. Just off the living space, the generous eat-in kitchen showcases updated stainless steel appliances and flows through sliding glass doors to a spacious back deck, an effortless setting for morning coffee, summer grilling, or weekend entertaining. Upstairs, two well-proportioned bedrooms provide a quiet retreat, served by two full baths newly remodeled with a clean, contemporary finish. The primary is located on its own level and provides all the area you ever wished for. Additional highlights include the convenience of city water and city sewer, recessed lighting throughout, and thoughtful updates that make this home genuinely move-in ready. All of this in one of Middlebury's most established neighborhoods, with quick access to Route 64 and I-84 for an easy commute toward Waterbury, Southbury, and beyond, plus shopping, dining, and everyday amenities close at hand. A rare opportunity to own a turnkey home in a location that truly delivers. Schedule your private showing today. Porch is now painted black.

Key Facts

City/Town
Middlebury
Neighborhood
N/A
Property / Style
Single Family · Split Level
Year Built
1962
Days on Market
14 days
Beds
3
Baths
3 full
Living Area
1,252 sq ft
Lot Size
0.42 acres
Garage / Parking
2 garage · 6 total
Property Taxes
$6,937 / Annually

Market Snapshot

The Middlebury Market

Single Family · trailing 12 months

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

$575,000

vs $672,000 median

14.4% below median

Price / Sq Ft

$459

vs $277 median

65.7% above median

Days on Market

14 days

vs 43 days median

29 days fresher 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

2 Northwood Drive, Middlebury, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$3,702

per month

  • Principal & Interest$2,932
  • Property Taxes$578
  • Insurance$192
  • 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
1962
New Construction
No/Resale
Living Area
1,252 sq ft

Schools

Elementary
Middlebury
Middle
Per Board of Ed
High
Pomperaug

Interior

Heating
Hot Water
Heat Fuel
Oil
Cooling
Central Air
Fireplaces
2
Laundry
Lower Level
Laundry Location
Lower finished level
Appliances
Oven/RangeMicrowaveRefrigeratorDishwasher
Basement
PartialHeatedFully Finished
In-Law Apartment
PossibleLower Level
Additional Rooms
Bonus Room

Exterior & Lot

Lot Size
0.42 acres
Zoning
R40
Garage / Parking
2 garage spaces6 total parking spacesAttached GaragePavedOff Street ParkingDrivewayPrivatePaved
Waterfront Details
Not Applicable
Water Source
Public Water Connected
Sewer
Public Sewer Connected
Construction
Vinyl Siding
Color
White
Roof
Asphalt Shingle
Foundation
Concrete
Exterior Features
DeckGuttersLighting
Lot Description
In SubdivisionLevel LotCleared

Listing & Financials

Property Taxes
$6,937 / Annually
Days on Market
14
MLS #
24190906
MLS Status
Active

Similar Properties

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

Listed By

Wayne Watt Jr.

(203) 206-2236

THE CONNECTICUT AGENCY LLC

(860) 830-8996

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 6:10 AM UTC.