18/18 Winding Trail

Off Market

18/18 Winding Trail

Middlebury CT 06762

4051 sq. ft.

Condo

Last sold for $695,000

Jay Irvine, last sold this property on 21 November 2025 after 95 days on market.

Overview

Welcome to this luxury home w/ custom features never seen before! This 4000+ sqft, 3 BEDROOM SUITES, 3.2 bath has elegance and comfort, built w/ never seen upgrades. On the most sought-after private cul-de-sac St. and the best location in the complex. Enter through a grand two-story foyer with gleaming hardwood floors, cathedral ceilings & soaring windows that fill the home with natural light. Beautiful curves staircase, formal living & dining rooms set the stage for entertaining. The gourmet kitchen boasts granite counters, beautiful cabinets, stainless steel appliances, gas cooktop, tile backsplash, large island for ample prep space, a chefs dream. The family room has vaulted ceilings & gas fireplace creates the ultimate gathering space. Rare floor plan features three bedroom suites: a main-level primary with tray ceiling, dual walk-in closets, spa-like ensuite with soaking tub & shower, plus two additional suites upstairs that each have THEIR OWN BATHROOM. Oversized loft overlooks the main floor. Finished walkout basement adds a rec/play room with a custom wet bar w/ granite counters & white cabinets, media area or office, half bath (potential for lower in law/ 4th bedroom). Highlights: laundry w/ sink, additional gas hookup in basement for fireplace, finished lower patio, upper deck & full wheelchair accessibility. Largest backyard in community, great for entertaining or playing sports. Clubhouse w/ bar, pool, gym, tennis crt, indoor basketball court! This is a MUST see!

Features

3 bedrooms

5 bathrooms

4 carspaces

2 garage spaces

4051 sq. ft. floor area

Condo

Estimated Value

Based on this property and similar 3 bedroom condos sold in Middlebury over the last 12 months, the estimated median property value of 18/18 Winding Trail is $571.74k.

Median value

$571.74k

Estimated value range

$509.9k - $695k

Median days on market

Estimated value trend

increase over the last 12 months

Average days on market is based on recent, comparable sales in Middlebury. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 18/18 Winding Trail

2025

Sold

$695,000

21 Nov 2025 by Jay Irvine, of Serhant Connecticut, LLC

Happy sellers in Middlebury

We have insufficient information to provide an overview of customer satisfaction for Middlebury. Viewing the agent profiles, reviews and sales for Middlebury can provide insights for this location.

Local market activity for 3 bedroom condos in Middlebury

In the last 12 months, 23 three-bedroom condos similar to 18/18 Winding Trail, have been sold.

This represents a 9% increase in three-bedroom condos sales when compared to the previous 12 months.

Sold

For Sale

Interested in selling?

People are reaching out to these agents in Middlebury for a market analysis.

Ken Demirs

at Regency Real Estate, LLC

(76 reviews)

Get a market analysis

Lauren Auresto

at Keller Williams Realty

(7 reviews)

Get a market analysis

Jay Irvine

at Showcase Realty, Inc.

(1 review)

Get a market analysis

Christina Zainc

at BHGRE Bannon & Hebert

(15 reviews)

Get a market analysis

Nearby agents

Compare and contact these top performing agents who’ve delivered exception customer service for their clients in Middlebury

Ken Demirs

Sellers who recommend Ken Demirs have praised them for being local expert, clear communication, responsive, reliable, dedicated, patient, and supportive