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36 Highridge Road #36

Middlebury, Connecticut 06762

PENDING$585,000
Beds
3
Baths
2 | 1
SqFt
1,997
Year Built
2018
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
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2-Car Garage1 Fireplace

About This Home

Welcome to 36 Highridge Road, a beautifully maintained home in one of Middlebury's most desirable neighborhoods. Built in 2018 and lovingly cared for by its original and only owner, this property offers the perfect blend of modern construction, thoughtful upgrades, and low-maintenance living. Step inside to find a thoughtfully designed interior enhanced with upgraded molding, elegant cabinetry, and high-end appliances that elevate both style and functionality. The inviting living space is truly a showstopper, featuring soaring 30-foot ceilings and a stunning fireplace that creates a warm yet dramatic focal point-perfect for both relaxing and entertaining. Nestled on a highly sought-after cul-de-sac, this home offers both privacy and a true sense of community. Beyond the home itself, residents enjoy access to exceptional, fully loaded amenities including a beautiful clubhouse, resort-style pool, playground, tennis courts, and both indoor and outdoor basketball courts-perfect for an active and social lifestyle. This is a rare opportunity to own a newer construction home with premium upgrades in a prime location-don't miss it! Sale is contingent on seller finding suitable housing.

Key Facts

City/Town
Middlebury
Neighborhood
N/A
Property / Style
Condo · Townhouse
Year Built
2018
Days on Market
127 days
Beds
3
Baths
2 full · 1 half
Living Area
1,997 sq ft
Garage / Parking
2 garage · 2 total
Property Taxes
$8,045 / Annually
HOA Fee
$495 / Monthly

Market Snapshot

The Middlebury Market

Condo · trailing 12 months

Median Days on Market

33

2 active listings

Median $ / Sq Ft

$236

2 active listings

Sale-to-List Ratio

100.0%

34 sales

How this home compares

List Price

$585,000

vs $539,900 median

8.4% above median

Price / Sq Ft

$293

vs $236 median

24.2% above median

Days on Market

127 days

vs 33 days median

94 days longer than median

Based on 2 active and 34 closed sales (trailing 12 mo) of condo in Middlebury. Source: SmartMLS · As of August 5, 2026.

Location

36 Highridge Road #36, Middlebury, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$4,367

per month

  • Principal & Interest$3,007
  • Property Taxes$670
  • Insurance$195
  • HOA$495

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
Condo
Subtype
Condominium
Style
Townhouse
Year Built
2018
New Construction
No/Resale
Living Area
1,997 sq ft

Schools

Elementary
Per Board of Ed
Middle
Per Board of Ed
High
Per Board of Ed

Interior

Heating
Hot AirZoned
Heat Fuel
Natural Gas
Cooling
Central Air
Fireplaces
1
Laundry
Main Level
Laundry Location
First Floor
Appliances
Oven/RangeMicrowaveRefrigeratorDishwasherWasherElectric Dryer
Basement
FullUnfinished
In-Law Apartment
PossibleUpper Level
Interior Features
Auto Garage Door OpenerCable - Pre-wiredOpen Floor Plan
Additional Rooms
Laundry Room

Exterior & Lot

Zoning
Per Town
Garage / Parking
2 garage spaces2 total parking spacesAttached GarageDriveway
Waterfront Details
Not Applicable
Water Source
Public Water Connected
Sewer
Public Sewer Connected
Flood Zone
No
Construction
Vinyl SidingStone
Exterior Features
Porch
Lot Description
Lightly WoodedOn Cul-De-Sac

HOA / Association

Fee
$495 / Monthly
Amenities
Basketball CourtClub HouseExercise Room/Health ClubGuest ParkingPlayground/Tot LotPrivate Rec FacilitiesPoolTennis Courts

Listing & Financials

Property Taxes
$8,045 / Annually
Days on Market
127
MLS #
24163482
MLS Status
Under Contract
Financing
FHA,VA

Similar Properties

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

Listed By

John Pistorino

(914) 356-5190

RE/MAX RISE

(203) 714-6479

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 8/5/2026. 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 8/5/2026 at 6:40 PM UTC.