27 Winding Trail 27 Middlebury, CT $ 565,000
27 Winding Trail 27
$ 565,000
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27 Winding Trail 27

Middlebury, CT, 06762
$ 565,000
Bedrooms3 Baths2.1 Sq 2,680

Monthly Estimate*

$ 3,525

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Condo for sale in Middlebury, CT

for $565,000 with 3 bedrooms and 2 full baths, 1 half bath. This 2,680 square foot condo was built in 2014.

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!

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Condo Contingent

Price

$ 565,000

Bedrooms

3

Full Bath

2

Half Bath

1

Property Type

Condo

Taxes

$ 10,036

Style

Year Built

2014

Town/City

Middlebury

MLS | Web ID

24133988

Features
General
Zoning PRD80
Neighborhood N/A
County New Haven
Unit Number 27
Tax Year July 2025-June 2026
Property Type Condo/Co-Op For Sale
Status Under Contract - Continue to Show
Directions GPS
High School Pomperaug
City Middlebury
Elementary School Per Board of Ed
Sq Ft Total 2680
DOM 17
Year Built 2014
Complex Ridgewood at Middlebury
Style Townhouse
Association Amenities Basketball Court Club House Exercise Room/Health Club Playground/Tot Lot Pool Tennis Courts
Year Built Source Public Records
Pool Description Heated In Ground Pool
Energy Features Programmable Thermostat Thermopane Windows
Association Fee Includes Club House Tennis Grounds Maintenance Trash Pickup Snow Removal Property Management Pest Control Pool Service Insurance
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Interior
Cooling System Central Air
Total Number of Units 270
Total Rooms 9
Basement Description Full Heated Fully Finished Walk-out Liveable Space Full With Walk-Out
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Exterior
Water Source Public Water Connected
Lot Description Lightly Wooded Level Lot On Cul-De-Sac
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* Excluded Features
List By
Jay Irvine

Listing Agent

Serhant Connecticut, Llc

Broker

realtor.j.irvine@gmail.com

Email

Affordability Calculator

$4,361
Per Month
81%
19%
0%
Monthly Principal & Interest
$3,525
Monthly Property Taxes
$836
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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The time to sell is now
THE TIME TO SELL IS NOW! What's my home worth?
Nearby
3042222 Elementary School
3042695 Middle School
Pomperaug High School High School
Pricing History
DatePricePrice ChangeDescription
10/17/2025$565,000 Listed Price

Map


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27 Winding Trail 27, Middlebury, CT, 06762 is a Condo for sale at $565,000 with 2,680 sqft. 27 Winding Trail 27 has 3 bedrooms, 2.1 baths, and was built in 2014. The property's zip code is 06762 which is in Middlebury, CT