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$559,900

  • Sold
  • Closed
  • Townhouse
  • 3 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 3,179 Sq. Ft.
  • 1 Car Garage
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Welcome to 3 Winding Trail, nestled on a quiet cul-de-sac in the highly desirable Ridgewood community of Middlebury. This beautifully maintained 3-bedroom, 2.5-bath condo offers the perfect blend of elegance, comfort, and low-maintenance living across 4 finished levels, including a sun-filled walk-out lower level. From the moment you step inside, you'll appreciate the gleaming hardwood floors, natural light throughout, spacious layout, and updated kitchen featuring granite countertops, stainless steel appliances, and ample space for entertaining. The spacious primary suite offers a peaceful retreat, while the additional finished spaces provide incredible flexibility for a family room, home office, gym, playroom, or guest area. Step outside to your private deck and patio surrounded by peaceful wooded views - perfect for relaxing or entertaining. Enjoy resort-style amenities including a pool, tennis courts, clubhouse, and fitness center, all within minutes of shopping, dining, and major commuter routes. Move-in ready and located in one of Middlebury's most sought-after communities, this is a rare opportunity you won't want to miss.

Full Property Details for 3 Winding Trail #3

General

  • Sold For: $559,900
  • HOA FEE: $495/month
  • Taxes: (July 2025-June 2026)
  • Status: Closed
  • Type: Townhouse
  • Source: SMARTMLS
  • MLS ID: 24177196
  • Added to Site: 97 day(s) ago

Interior

  • Number of Rooms: 7
  • Appliances: Gas Range, Refrigerator, Dishwasher

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 2
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 3
  • Primary Bedroom: Primary Bedroom, Upper
  • Bedroom 1: Bedroom, Upper
  • Bedroom 2: Bedroom, Upper

Other Rooms

  • Living Room: Living Room, Main
  • Dining Room: Dining Room, Main

Additional Information

  • Pool: Yes
  • Pool Description: In Ground Pool

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 1
  • Parking: Attached Garage

Location

  • County: New Haven
  • Complex: Ridgewood at Middlebury
  • Driving Directions: GPS-friendly

School Information

  • Elementary School: Per Board of Ed
  • High School: Per Board of Ed

Community

  • Association: Yes
  • Home Owners Assn.: 1
  • Assoc. Fees Include: Club House, Tennis, Grounds Maintenance, Trash Pickup, Snow Removal, Pest Control, Pool Service, Road Maintenance
  • Pets Allowed: Yes
  • Pet Restrictions: Yes with Restrictions

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Hot Air, Natural Gas
  • Heating Fuel: Natural Gas
  • Water Heater: Natural Gas, Tankless Hotwater

Utilities

  • Sewer: Public Sewer Connected
  • Water: Public Water Connected

Structural Information

  • Architectural Style: Townhouse
  • Construction Status: No/Resale
  • Exterior Const.: Vinyl Siding
  • Basement Desc.: Full, Full With Walk-Out
  • Attic: Yes
  • Square Feet: 3,179
  • Above Ground: 2,403 Sq. Ft.
  • Below Ground: 776 Sq. Ft.
  • Year Built: 2007

Lot Features

  • Zoning: Residential
  • Lot Description: On Cul-De-Sac

Financial Considerations

  • Association Fee: $495
  • Assoc Fee Freq.: Monthly
  • Assessment Amount: $320,180
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 2547175

Listed by Showcase Realty, Inc., Mayra Perez
Sold by William Raveis Real Estate, Ray Getman

Listing agent

— 3 Winding Trail #3 —

  • Mayra Perez

    Showcase Realty, Inc.

Agent Contact: (203) 558-5866 Office Contact: (860) 274-7000

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 3 Winding Trail #3

School District:Regional School District 15
NameGradesDistance
Long Meadow Elementary School
65 North Benson Road, Middlebury, CT 06762
PK-51.3 mi
Memorial Middle School, Middlebury, CT
1 Memorial Drive, Middlebury, CT 06762
6-82.8 mi
Pomperaug Regional High School
234 Judd Road, Southbury, CT 06488
9-121.7 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 3 Winding Trail #3

Date
Details
Price
Change
Source
7/16/2026
Sold
$559,900
—
MLS
5/23/2026
Listed
$559,900
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Listed by Showcase Realty, Inc., Mayra Perez
Sold by William Raveis Real Estate, Ray Getman

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3 Winding Trail #3, Middlebury, CT 06762 (MLS# 24177196) is a Townhouse property that was sold at $559,900 on July 16, 2026. Want to learn more about 3 Winding Trail #3? Do you have questions about finding other Townhouse real estate for sale in Middlebury? You can browse all Middlebury real estate or contact a Coldwell Banker agent to request more information.