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$559,900 Just Listed

  • For Sale
  • Active
  • Townhouse
  • 3 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 3,179 Sq. Ft.
  • 2 Car Garage
  • Updated 1 day ago
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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

  • Price: $559,900
  • HOA FEE: $495/month
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Townhouse
  • Source: SMARTMLS
  • MLS ID: 24177196
  • Updated: 5/23/2026
  • Added to Site: 2 day(s) ago

Interior

  • Number of Rooms: 7
  • Appliances: Gas Range, Refrigerator, Subzero, 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: 2
  • 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: $247,300
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 2547175

Listed by Showcase Realty, Inc., Mayra Perez

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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

Price & Sales History for 3 Winding Trail #3 Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/23/2026
Listed
$559,900
67.13%
MLS
10/30/2019
Sold
$335,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 3 Winding Trail #3

Year
Property Taxes
Change
Tax Assessment
Change
2025
$8,042
—
$247,300
—
2023
$8,062
1%
$247,300
—
2023
$7,978
3%
$247,300
—
2022
$7,731
—
$247,300
11%
2021
$7,731
-2%
$223,700
—
2020
$7,852
5%
$223,700
—
2019
$7,472
3%
$223,700
—
2018
$7,272
3%
$223,700
—
2017
$7,044
1%
$223,700
—
2016
$6,956
3%
$224,300
—
2015
$6,756
3%
$224,300
—
2014
$6,581
2%
$224,300
—
2011
$6,473
—
$224,300
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Showcase Realty, Inc., Mayra Perez

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3 Winding Trail #3, Middlebury, CT 06762 (MLS# 24177196) is a Townhouse property with 3 bedrooms, 2 full bathrooms and 1 partial bathroom. 3 Winding Trail #3 is currently listed for $559,900 and was received on May 23, 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.

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