3 Brookside Drive #3
Middlebury, Connecticut 06762
Reduced from $659,900
- Beds
- 4
- Baths
- 2 | 2
- SqFt
- 4,200
- Acres
- 1.00
- Year Built
- 2004
- 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
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
- 291 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
Active Listings
25
20 under contract
Median List Price
$670,000
25 active listings
Median Closed Price
$574,900
79 sales
Median Days on Market
45
25 active listings
Median $ / Sq Ft
$280
25 active listings
Sale-to-List Ratio
100.0%
79 sales
How this home compares
List Price
$599,900
vs $670,000 median
10.5% below median
Price / Sq Ft
$143
vs $280 median
48.9% below median
Days on Market
291 days
vs 45 days median
246 days longer than median
Based on 25 active and 79 closed sales (trailing 12 mo) of single family in Middlebury. Source: SmartMLS · As of October 15, 2026.
Location
3 Brookside Drive #3, Middlebury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 15, 2026per month
- Principal & Interest$3,323
- 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
- 291
- MLS #
- 24146182
- MLS Status
- Under Contract - Continue to Show
- Financing
- FHA,VA,CHFA
Similar Properties
Homes with a close match in area, property type, and price.
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 10/15/2026. 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 10/15/2026 at 10:40 PM UTC.