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3 Brookside Drive #3

Middlebury, Connecticut 06762

PENDING$599,900

Reduced from $659,900

Beds
4
Baths
2 | 2
SqFt
4,200
Acres
1.00
Year Built
2004
Matt Caiola

Matt Caiola

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MCMATT CAIOLALUXURY PROPERTIES
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2-Car Garage1 FireplacePrice Reduced

About This Home

Discover refined comfort and timeless elegance in this beautifully appointed Cheshire model, nestled within the highly sought-after Brookside of Middlebury community. This exceptional 4-bedroom, 2 full and 2 half bath home is truly move-in ready. Open-concept floor plan that instantly impresses. The stylish kitchen features granite countertops, new modern LG appliances, and seamless flow into the main living areas-perfect for hosting family and friends. First-floor primary suite, complete with a luxurious jacuzzi tub and two spacious walk-in closets. Through elegant glass French doors, you'll find a dream dressing room or home office, outfitted with a PAX wardrobe system, dressing table, and desk. The dramatic two-story foyer leads to the upper level, offering three additional bedrooms and a full bath, all overlooking the stunning two-story living room with a cozy fireplace. The finished walk-out basement expands your living space with endless possibilities-ideal for a home office, gym, media room, or game area. An additional 600+ sq ft of storage with a tool bench provides ample space for hobbies and organization. Enjoy peaceful mornings or relaxing evenings on the expansive deck, taking in tranquil views of the lush, protected preserve. This is more than just a house-it's a place to be a truly HOME !!! AS IS SALE (INSPECTIONS ARE INFOMATIONAL PURPOSES ONLY )

Key Facts

City/Town
Middlebury
Neighborhood
N/A
Property / Style
Single Family · Cape Cod
Year Built
2004
Days on Market
212 days
Beds
4
Baths
2 full · 2 half
Living Area
4,200 sq ft
Lot Size
1.00 acres
Garage / Parking
2 garage
Property Taxes
$11,141 / Annually
HOA Fee
$195 / Monthly

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

$599,900

vs $672,000 median

10.7% below median

Price / Sq Ft

$143

vs $277 median

48.4% below median

Days on Market

212 days

vs 43 days median

169 days longer 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

3 Brookside Drive #3, Middlebury, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$4,382

per month

  • Principal & Interest$3,059
  • Property Taxes$928
  • Insurance$200
  • HOA$195

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
Cape Cod
Year Built
2004
New Construction
No/Resale
Living Area
4,200 sq ft
Below Grade
1,250 sq ft

Schools

Elementary
Per Board of Ed
High
Per Board of Ed

Interior

Heating
Hot Air
Heat Fuel
Natural Gas
Cooling
Central Air
Fireplaces
1
Laundry
Main Level
Appliances
Oven/RangeMicrowaveRefrigeratorDishwasher
Basement
FullFully FinishedFull With Walk-Out
In-Law Apartment
PossibleLower Level

Exterior & Lot

Lot Size
1.00 acres
Zoning
PRD
Garage / Parking
2 garage spacesAttached Garage
Waterfront Details
Not Applicable
Water Source
Public Water Connected
Sewer
Public Sewer Connected
Construction
Vinyl Siding
Roof
Asphalt Shingle
Foundation
Concrete
Lot Description
Lightly WoodedLevel Lot

HOA / Association

Fee
$195 / Monthly

Listing & Financials

Property Taxes
$11,141 / Annually
Days on Market
212
MLS #
24146182
MLS Status
Under Contract - Continue to Show
Financing
FHA,VA,CHFA

Similar Properties

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Listed By

Shagufta Zahid

(203) 558-9101

S Factor Realty Group LLC

(203) 302-0672

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 7:01 AM UTC.