3/3 Winding Trail

Off Market

3/3 Winding Trail

New Haven County CT 06762

3179 sq. ft.

Condo

Last sold for $559,900

Mayra Perez, last sold this property on 16 July 2026 after 53 days on market.

Overview

Welcome to 3 Winding Trail, nestled on a quiet cul-de-sac in the highly desirable Ridgewood community of Middlebury. This beautifully maintained 3-bedroom, 2.5-bath condo offers the perfect blend of elegance, comfort, and low-maintenance living across 4 finished levels, including a sun-filled walk-out lower level. From the moment you step inside, you'll appreciate the gleaming hardwood floors, natural light throughout, spacious layout, and updated kitchen featuring granite countertops, stainless steel appliances, and ample space for entertaining. The spacious primary suite offers a peaceful retreat, while the additional finished spaces provide incredible flexibility for a family room, home office, gym, playroom, or guest area. Step outside to your private deck and patio surrounded by peaceful wooded views - perfect for relaxing or entertaining. Enjoy resort-style amenities including a pool, tennis courts, clubhouse, and fitness center, all within minutes of shopping, dining, and major commuter routes. Move-in ready and located in one of Middlebury's most sought-after communities, this is a rare opportunity you won't want to miss.

Features

3 bedrooms

3 bathrooms

1 carspace

1 garage space

3179 sq. ft. floor area

Condo

Estimated Value

Based on this property and similar 3 bedroom condos sold in New Haven County over the last 12 months, the estimated median property value of 3/3 Winding Trail is $565k.

Median value

$565k

Estimated value range

$499.9k - $695k

Median days on market

Estimated value trend

-3%

decrease over the last 12 months

Average days on market is based on recent, comparable sales in New Haven County. 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 3/3 Winding Trail

2026

Sold

$559,900

16 Jul 2026 by Mayra Perez, of Showcase Realty, Inc.

2019

Sold

$335,000

05 Nov 2019 by Jay Irvine, of Showcase Realty, Inc.

Happy sellers in New Haven County

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

Local market activity for 3 bedroom condos in New Haven County

In the last 12 months, 24 three-bedroom condos similar to 3/3 Winding Trail, have been sold.

This represents a 127% decrease 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 New Haven County for a market analysis.

Ken Demirs

at Regency Real Estate, LLC

(73 reviews)

Get a market analysis

Lauren Auresto

at BHGRE Gaetano Marra Homes

(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 New Haven County

Ken Demirs

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