$625,000
SOLD APR 10, 2026

16 Winding Trail Middlebury, CT 06762

3 Beds
2.5 Baths
2,646 Sq Ft
2014 Built

Sale Details

Date Sold: April 10, 2026

$236 Per Sq Ft

29 Days on Market

Highlights

  • Health Club
  • Pool House
  • Clubhouse
  • Pomperaug Regional High School Rated A
  • Open Floorplan
  • Deck

About This Home

As of April 2026

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.

Last Agent to Sell the Property

Georgieanna Fisher

Home Selling Team Brokerage Phone: (860) 428-3078 License #RES.0795195 Listed on: 03/04/2026

Last Buyer's Agent

David Landau

RE/MAX Right Choice License #RES.0797458

RE/MAX Right Choice

Property Details

Home Type

  • Condominium

Est. Annual Taxes

  • $10,484

Year Built

  • Built in 2014

HOA Fees

  • $495 Monthly HOA Fees

Home Design

  • Frame Construction
  • Vinyl Siding

Interior Spaces

  • 2,646 Sq Ft Home
  • Open Floorplan
  • Ceiling Fan
  • 1 Fireplace
  • Thermal Windows
  • French Doors
  • Attic or Crawl Hatchway Insulated
  • Smart Thermostat

Kitchen

  • Built-In Oven
  • Gas Cooktop
  • Microwave
  • Dishwasher
  • Disposal

Bedrooms and Bathrooms

  • 3 Bedrooms

Laundry

  • Laundry on upper level
  • Electric Dryer
  • Washer

Basement

  • Walk-Out Basement
  • Basement Fills Entire Space Under The House

Parking

  • 2 Car Garage
  • Parking Deck
  • Automatic Garage Door Opener
  • Guest Parking
  • Visitor Parking

Pool

  • Pool House
  • Heated In Ground Pool
  • Fence Around Pool

Outdoor Features

  • Deck
  • Patio

Location

  • Property is near public transit

Utilities

  • Central Air
  • Heating System Uses Natural Gas
  • Programmable Thermostat
  • Underground Utilities
  • Power Generator
  • Cable TV Available

Listing and Financial Details

  • Assessor Parcel Number 2547193

Community Details

Overview

  • Association fees include club house, grounds maintenance, trash pickup, snow removal, property management, pest control, road maintenance, insurance
  • 251 Units
  • Property managed by TPG The Property Group

Amenities

  • Clubhouse
  • Elevator

Recreation

  • Health Club
  • Tennis Courts
  • Community Playground
  • Exercise Course
  • Community Pool

Pet Policy

  • Pets Allowed

Property Details

Home Type

Condominium

Est. Annual Taxes

$10,484

Year Built

Built in 2014

HOA Fees

$495 per month

Listing Details

  • Neighborhood: N/A
  • Property Type: Condo/Co-Op For Sale
  • Style: Other
  • Sq Ft Est Heated Above Grade: 2646
  • Total Sq Ft: 2646
  • Year Built: 2014
  • New Construction: No/Resale
  • Nearby Amenities: Basketball Court, Commuter Bus, Health Club, Library, Medical Facilities, Park, Playground/Tot Lot, Tennis Courts
  • In Law Access: LOWER,ENTRY
  • Association Amenities: Club House, Elevator, Exercise Room/Health Club, Guest Parking, Health Club, Playground/Tot Lot, Pool, Tennis Courts
  • Remarks Public Addendum: 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?
  • Property Sub Type: Condominium
  • Direct Waterfront: No
  • Encumbrances Restrictions: Boats, Trailer(S), Truck(S)
  • End Unit: No
  • Home Warranty Offered: No
  • Radon Mitigation Air Ynu: No
  • Radon Mitigation Water Ynu: No
  • Condo Model Name: Denton
  • 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.
  • Financing Used: Cash
  • In Law Apartment: Possible
  • Spec Assoc Asses: No
  • Street Type: Trail
  • Office Attribution Contact: (860) 456-7653
  • Reserve Prospect: No
  • Special Features: None

Interior Features

  • Total Bedrooms: 3
  • Total Bathrooms: 3
  • Full Bathrooms: 2
  • Half Bathrooms: 1
  • Fireplaces: 1
  • Attic Description: Access Via Hatch
  • Basement Description: Full, Full With Walk-Out
  • Interior Amenities: Auto Garage Door Opener, Cable - Pre-wired, Open Floor Plan
  • Appliances: Gas Cooktop, Wall Oven, Microwave, Refrigerator, Dishwasher, Disposal, Washer, Electric Dryer
  • Laundry Room Location: Off bedroom hallway
  • Laundry Room Info: Upper Level
  • Attic: Yes
  • Home Automation: Thermostat(s)

Exterior Features

  • Exterior Features: Underground Utilities, Sidewalk, Tennis Court, Deck, French Doors, Patio
  • Exterior Siding: Vinyl Siding
  • Waterfront Description: Not Applicable
  • Swimming Pool: Yes
  • Pool: Heated, Pool House, Safety Fence, In Ground Pool
  • Construction Description: Frame

Garage/Parking

  • Garages Number: 2
  • Total Parking Spaces: 4
  • Garage And Parking: Attached Garage, Paved, Driveway

Utilities

  • Cooling System: Ceiling Fans, Central Air
  • Heat Type: Hot Air
  • Heat Fuel Type: Natural Gas
  • Hot Water Description: 50 Gallon Tank, Upright Tank
  • Water Source: Public Water Connected
  • Sewer: Public Sewer Connected

Condo/Co-op/Association

  • Association Fee Includes: Club House, Grounds Maintenance, Trash Pickup, Snow Removal, Property Management, Pest Control, Road Maintenance, Insurance
  • HOA Fees: 495
  • HOA Fee Frequency: Monthly
  • Property Management Type: Professional-Off Site
  • Property Manager Name: Alyssa Doutney
  • Property Manager Phone: (203) 890-0147
  • Property Mgt Company Name: TPG The Property Group
  • Property Mgt Phone: (203) 967-8337
  • Total Number of Units In Complex: Ridgewood at Middlebury

Schools

  • Intermediate School: Per Board of Ed

Green Features

  • Energy Features: Generator Ready, Programmable Thermostat, Thermopane Windows

Lot Info

  • Lot Description: Lightly Wooded Level Lot Rolling
  • Flood Zone: No
  • Zoning: Res Condo
  • Parcel #: 2547193

Rental Info

  • Pets Allowed Info: Detailed in Condo docs
  • Pets Allowed: Yes

Multi Family

  • Total Number Of Units: 251

Tax Info

  • Tax Year: July 2025-June 2026
  • Property Tax: 10484

MLS Schools

  • Elementary School: Per Board of Ed
  • Middle Jr High School: Per Board of Ed
  • High School: Per Board of Ed
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Home Values in the Area

Source: Public Records

Average Home Value in this Area

Source: Public Records

Property History

Date Event Price List to Sale Price per Sq Ft Prior Sale
04/10/2026 04/10/26 Sold $625,000 0.0% $236 / Sq Ft
04/02/2026 04/02/26 Pending -- -- --
03/01/2026 03/01/26 For Sale $625,000 +17.9% $236 / Sq Ft
05/13/2022 05/13/22 Sold $529,900 0.0% $200 / Sq Ft View Prior Sale
04/01/2022 04/01/22 Pending -- -- --
03/25/2022 03/25/22 For Sale $529,900 +20.4% $200 / Sq Ft
09/04/2020 09/04/20 Sold $440,000 -2.2% $166 / Sq Ft View Prior Sale
08/26/2020 08/26/20 Pending -- -- --
07/21/2020 07/21/20 For Sale $449,900 +4.2% $170 / Sq Ft
02/27/2015 02/27/15 Sold $431,686 +12.1% $174 / Sq Ft View Prior Sale
03/31/2014 03/31/14 For Sale $384,995 -- $155 / Sq Ft
03/15/2014 03/15/14 Pending -- -- --
Source: SmartMLS

Agents Affiliated with this Home

  • Georgieanna Fisher

    Seller's Agent in 2026

    Georgieanna Fisher

    Home Selling Team

    (860) 428-3078

    2 in this area

    55 Total Sales

    Georgieanna Fisher
    Section Image
  • David Landau

    Buyer's Agent in 2026

    David Landau

    RE/MAX

    (203) 948-2703

    2 in this area

    143 Total Sales

    David Landau
    Section Image
  • Jay Irvine

    Seller's Agent in 2022

    Jay Irvine

    Serhant Connecticut, LLC

    (203) 586-9459

    20 in this area

    78 Total Sales

    Jay Irvine
    Section Image
  • Lynn LaForme

    Seller's Agent in 2020

    Lynn LaForme

    Regency Real Estate, LLC

    (203) 910-8618

    2 in this area

    180 Total Sales

    Lynn LaForme
    Section Image
  • Meredith Colasanto

    Seller's Agent in 2015

    Meredith Colasanto

    Lamacchia Realty

    (203) 577-6640

    8 in this area

    15 Total Sales

    Meredith Colasanto
    Section Image
  • Donna Bannon

    Buyer's Agent in 2015

    Donna Bannon

    BHGRE Gaetano Marra Homes

    (203) 233-7499

    39 in this area

    82 Total Sales

    Donna Bannon
    Section Image
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Map

Source: SmartMLS

MLS Number: 24157092

SmartMLS
Connecticut New Haven County Middlebury 06762

16 Winding Trail, Middlebury, CT

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

SmartMLS IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

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