16 Winding Trail 16 Middlebury, CT $ 625,000
16 Winding Trail 16
$ 625,000
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Open House 3/6 3:30pm - 5:30pm
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16 Winding Trail 16

Middlebury, CT, 06762
$ 625,000
Bedrooms3 Baths2.1 Sq 2,646

Monthly Estimate*

$ 3,848

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Condo for sale in Middlebury, CT

for $625,000 with 3 bedrooms and 2 full baths, 1 half bath. This 2,646 square foot condo was built in 2014.

Set at the end of a quiet cul-de-sac in one of Ridgewood's most coveted locations, this home overlooks an expansive manicured lawn bordered by evergreens and woodland for exceptional privacy and year round natural beauty. Sunlight fills every room, enhancing the warm, cohesive feel of HARDWOOD FLOORS THROUGHOUT BOTH LEVELS - a rare feature in this community. The bright, sparkling kitchen features white cabinetry, undermount lighting, stainless appliances, & spacious center island/breakfast bar perfect for "cooking with company". Genuine MARBLE in the kitchen & baths adds the patina of refined, timeless elegance. A charming breakfast nook overlooks the sundeck, inviting you to dine al fresco basking in sunshine & nature. An open dining area flows easily into the large living room with gas fireplace which provides warmth & ambiance as do the $5,600 Modern Smart Shades. A flexible office/playroom/den completes the main floor. Upstairs, a loft offers flex space leading to the primary suite with walk-in closet, double vanity, tile shower & jacuzzi tub. Two additional bedrooms, a full bath, and laundry complete this level. The walkout lower level has great sunlight with glass doors opening to the patio and is plumbed for potential in-law, workshop or family room. Ridgewood amenities include an 8,300 sq ft clubhouse, fitness center, yoga space, movie theatre, indoor basketball, tennis, & heated pool - A resort oasis! Don't miss this rare opportunity to own this truly special home. The Ridgewood community is truly multigenerational and welcoming. The old fashioned friendly neighborhood feel at its finest. There are sidewalks throughout. Head out morning and evening and find folks walking. For the younger set, there's a kiddie pool and playground, furthering opportunity to get to know your neighbors. The Club house has lounge area with a piano, couches and TV, bar, pool/ poker tables. A kitchen can be rented out for larger gatherings. Tennis court can also be a full basketball court! Pickup game anyone? For exercise enthusiasts of all levels, the nearby Middlebury Greenway is a ~4.5 to 6-mile paved rail-trail, ideal for walking, biking, and wheelchairs. It follows a former 1908 electric trolley line connecting Quassy Amusement Park to the Straits Turnpike (Route 63), passing through scenic areas and near parks like Meadowview, right across the street from Ridgewood. Come see how this luxurious yet friendly home can change your life. Are you ready for your nest Chapter?

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Open House

3/6/2026 3:30 PM - 5:30 PM
3/8/2026 11:00 AM - 1:00 PM
16 Winding Trail 16 Middlebury, CT
* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm

Condo Active

Price

$ 625,000

Bedrooms

3

Full Bath

2

Half Bath

1

Property Type

Condo

Taxes

$ 10,484

Style

Year Built

2014

Town/City

Middlebury

MLS | Web ID

24157092

Features
General
Zoning Res Condo
Neighborhood N/A
County New Haven
Unit Number 16
Tax Year July 2025-June 2026
Property Type Condo/Co-Op For Sale
Status Active
Directions From 184 heading West take exit 17 and continue straight onto Rte 64 Chase Pkway. Travel 3.6 miles to Ridgewood Drive on your Left. In 900' turn Left onto Winding Trail. #16 is 800' down the hill on your left.
High School Per Board of Ed
City Middlebury
Elementary School Per Board of Ed
Sq Ft Total 2646
DOM 0
Year Built 2014
Complex Ridgewood at Middlebury
Style Other
Association Amenities Club House Elevator Exercise Room/Health Club Guest Parking Health Club Playground/Tot Lot Pool Tennis Courts
Year Built Source Public Records
Pool Description Heated Pool House Safety Fence In Ground Pool
Energy Features Generator Ready Programmable Thermostat Thermopane Windows
Association Fee Includes Club House Grounds Maintenance Trash Pickup Snow Removal Property Management Pest Control Road Maintenance Insurance
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Interior
Cooling System Ceiling Fans Central Air
Total Number of Units 251
Total Rooms 6
Basement Description Full Full With Walk-Out
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Exterior
Water Source Public Water Connected
Lot Description Lightly Wooded Level Lot Rolling
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* Excluded Features
List By
Georgieanna Fisher

Listing Agent

Home Selling Team

Broker

georgieanna@homesellingteam.com

Email

Affordability Calculator

$4,722
Per Month
81%
19%
0%
Monthly Principal & Interest
$3,848
Monthly Property Taxes
$874
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% 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! What's my home worth?
Nearby
3092524 Elementary School
1232933 Middle School
Per Board of Ed High School High School
Pricing History
DatePricePrice ChangeDescription
3/4/2026$625,000 Listed Price

Map


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16 Winding Trail 16, Middlebury, CT, 06762 is a Condo for sale at $625,000 with 2,646 sqft. 16 Winding Trail 16 has 3 bedrooms, 2.1 baths, and was built in 2014. The property's zip code is 06762 which is in Middlebury, CT