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$625,000
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Property Description
Set at the end of a quiet cul-de-sac in ONE OF RIDGEWOODS 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 AND 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.
Full Property Details
Full Property Details for 16 Winding Trail #16
General
- Sold For: $625,000
- HOA FEE: $495/month
- Taxes: (July 2025-June 2026)
- Status: Closed
- Type: Condo
- Source: SMARTMLS
- MLS ID: 24157092
- Added to Site: 45 day(s) ago
Interior
- Number of Rooms: 6
- Interior Features: Auto Garage Door Opener, Cable - Pre-wired, Open Floor Plan
- Fireplace: Yes
- Number of Fireplaces: 1
- Appliances: Gas Cooktop, Wall Oven, Microwave, Refrigerator, Dishwasher, Disposal, Washer, Electric Dryer
Rooms
Bathrooms
- Total Bathrooms: 3
- Full Bathrooms: 2
- Half Bathrooms: 1
Bedrooms
- Total Bedrooms: 3
- Primary Suite: Ceiling Fan, Jack & Jill Bath, Hydro-Tub, Stall S, 17 x 15, Upper
- Bedroom 1: Bedroom - Ceiling Fan, Hardwood Floor, 14.3 x 11.8, Upper
- Bedroom 2: Bedroom - 9 ft+ Ceilings, Ceiling Fan, Hardwood Floor, 15.9 x 13.5, Upper
Other Rooms
- Living Room: Living Room - 9 ft+ Ceilings, Gas Log Fireplace, Fireplace, 18.7 x 14.7, Main
- Eat In Kitchen: Eat-In Kitchen - 9 ft+ Ceilings, Balcony/Deck, Breakfast Bar, Hardwood Floor, 22.6 x 11.9, Main
- Dining Room: Dining Room - 9 ft+ Ceilings, Hardwood Floor, 14.7 x 13.7, Main
- Office: Office - 9 ft+ Ceilings, Hardwood Floor, 11.9 x 11.8, Main
- Loft: Loft - 9 ft+ Ceilings, Hardwood Floor, 13.7 x 11, Upper
- Laundry: Upper Level
Additional Information
- Shared Amenities: Club House, Elevator, Exercise Room/Health Club, Guest Parking, Health Club, Playground/Tot Lot, Pool, Tennis Courts
- Pool: Yes
- Pool Description: Heated, Pool House, Safety Fence, In Ground Pool
Exterior
- Exterior Features: Underground Utilities, Sidewalk, Tennis Court, Deck, French Doors, Patio
- Color: Beige
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 2
- Total Spaces: 4
- Parking: Attached Garage, Paved, Driveway
Location
- County: New Haven
- Complex: Ridgewood at Middlebury
- Driving 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.
School Information
- Elementary School: Per Board of Ed
- Middle School: Per Board of Ed
- Intermediate School: Per Board of Ed
- High School: Per Board of Ed
Community
- Association: Yes
- Home Owners Assn.: 1
- Assoc. Fees Include: Club House, Grounds Maintenance, Trash Pickup, Snow Removal, Property Management, Pest Control, Road Maintenance, Insurance
- Pets Allowed: Yes
- Pet Restrictions: Detailed in Condo docs
Heating & Cooling
- Cooling Type: Ceiling Fans, Central Air
- Heating Type: Hot Air, Natural Gas
- Heating Fuel: Natural Gas
- Water Heater: 50 Gallon Tank, Upright Tank
Utilities
- Sewer: Public Sewer Connected
- Water: Public Water Connected
Structural Information
- Architectural Style: Other
- Model: Denton
- Construction Status: No/Resale
- Exterior Const.: Vinyl Siding
- Basement Desc.: Full, Full With Walk-Out
- Attic: Yes
- Square Feet: 2,646
- Above Ground: 2,646 Sq. Ft.
- Year Built: 2014
Lot Features
- Zoning: Res Condo
- Lot Description: Lightly Wooded, Level Lot, Rolling
Green Features
- Energy Features: Generator Ready, Programmable Thermostat, Thermopane Windows
Financial Considerations
- Association Fee: $495
- Assoc Fee Freq.: Monthly
- Annual Sewer Fee: $280
- Assessment Amount: $322,400
- Tax Year: July 2025-June 2026
Disclosures and Reports
- Property ID: 2547193
Listed by Home Selling Team, Georgieanna Fisher
Sold by RE/MAX Right Choice, David Landau
Get Pre-Approved Today
Schools
Schools serving 16 Winding Trail #16
School District:Regional School District 15
| Name | Grades | Distance |
|---|---|---|
Long Meadow Elementary School 65 North Benson Road, Middlebury, CT 06762 | PK-5 | 1.3 mi |
Memorial Middle School, Middlebury, CT 1 Memorial Drive, Middlebury, CT 06762 | 6-8 | 2.8 mi |
Pomperaug Regional High School 234 Judd Road, Southbury, CT 06488 | 9-12 | 1.8 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 16 Winding Trail #16
Date
Details
Price
Change
Source
4/10/2026
Sold
$625,000
—
MLS
3/01/2026
Listed
$625,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
16 Winding Trail #16, Middlebury, CT 06762 (MLS# 24157092) is a Condo property that was sold at $625,000 on April 10, 2026. Want to learn more about 16 Winding Trail #16? Do you have questions about finding other Condo real estate for sale in Middlebury? You can browse all Middlebury real estate or contact a Coldwell Banker agent to request more information.

