Recently Listed Open House 3/6 3:30pm - 5:30pm
16 Winding Trail 16
Middlebury, CT, 06762 $ 625,000
Bedrooms3 Baths2.1 Sq 2,646 Monthly Estimate*
$ 3,848
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
FeaturesGeneralZoning 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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InteriorCooling System Ceiling Fans Central Air
Total Number of Units 251
Total Rooms 6
Basement Description Full Full With Walk-Out
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ExteriorWater Source Public Water Connected
Lot Description Lightly Wooded Level Lot Rolling
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* Excluded FeaturesList ByGeorgieanna FisherListing Agent
georgieanna@homesellingteam.comEmail
Affordability Calculator
- 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.
Learn more about how to save NearbyCondo listings in Middlebury, CT
Average List Price $548,200
Percent of Sale Price 12%
About Middlebury, CT 7,671 Population
18% Since 2002
$ 105,125 Median Income
46.66 Median Age
27% Households with Children
Trends Information provided by ATTOM Data Solutions.
3092524 Elementary School
1232933 Middle School
Per Board of Ed High School High School
Pricing History| Date | Price | Price Change | Description |
|---|
| 3/4/2026 | $625,000 | | Listed Price |