Coldwell Banker Home Page
Local Realty Service Provided By: Coldwell Banker Country to Coast Realty
Property view
Listing view 2
Listing view 3

27 Winding Trail #27, 
Middlebury, CT 06762

$565,000


3

Beds


3

Baths


2,680

Sq Ft


Condo

Active

Listed by

Jay Irvine

Serhant Connecticut, LLC.

Last updated:

October 17, 2025, 01:47 PM

MLS#

24133988

Source:

CT

About This Home

27 Winding Trail #27

Beautiful Luxury Portman Condo in the Sought-After Ridgewood Community! This stunning 3-bed, 2.5-bath home by Toll Brothers is perfectly situated on a private cul-de-sac in one of Ridgewood's most desirable and unique locations. Offering over 2,680 SqFt of beautifully designed living space, this residence includes a rare 4-ft bump-out for added size plus a finished walk-out basement. The main level features an open floor plan with gleaming hardwood floors, custom cabinetry, stainless steel appliances, and marble countertops-perfect for modern entertaining. An upgraded skylight fills the kitchen with natural light, while sliding doors lead to a private deck with tranquil wooded views. The spacious living room highlights a gas fireplace with a stone veneer surround and rich wood mantle. Upstairs, entire 2nd level has upgraded designer hardwood flrs. Primary suite impresses with a walk-in closet and a spa-like bath w/ a double vanity, soaking tub, and separate shower. Two additional bedrooms include generous closets & soaring ceilings. The remodeled finished walk out basement is great for a media/ entertainment room. Enjoy the rare privacy of a wooded backdrop and direct access to the expansive "Great Meadow Lawn" next door-ideal for gatherings, games, or a peaceful stroll. Resort-style amenities include an outdoor pool, gym, tennis and basketball courts, movie theater, and clubhouse-all within walking distance. You can't build this home for the price, an absolute must-see!

Home Facts

Condo

3 Baths

3 Bedrooms

Built in 2014

Price Summary

565,000

$210 per Sq. Ft.

MLS #:

24133988

Last Updated:

October 17, 2025, 01:47 PM

Added:

6 day(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

3

Bathrooms

Total Bathrooms:

3

Full Bathrooms:

2

Interior

Living Area:

2,680 Sq. Ft.


Structure

Structure

Architectural Style:

Townhouse

Building Area:

2,680 Sq. Ft.

Year Built:

2014


Finances & Disclosures

Finances

Price:

$565,000

Price per Sq. Ft:

$210 per Sq. Ft.

Source:CT
The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2025 SmartMLS, Inc.

Contact an Agent

Yes, I would like more information from Coldwell Banker. Please use and/or share my information with a Coldwell Banker agent to contact me about my real estate needs.

By clicking Contact I agree a Coldwell Banker Agent may contact me by phone or text message including by automated means and prerecorded messages about real estate services, and that I can access real estate services without providing my phone number. I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

 

Contact an Agent

Yes, I would like more information from Coldwell Banker. Please use and/or share my information with a Coldwell Banker agent to contact me about my real estate needs.

By clicking Contact I agree a Coldwell Banker Agent may contact me by phone or text message including by automated means and prerecorded messages about real estate services, and that I can access real estate services without providing my phone number. I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.