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.
Accepting backups
$559,900
3 Winding Trail #3, Middlebury, CT 06762
3beds
3,179sqft
Condominium, Townhouse
Built in 2007
-- sqft lot
$549,900 Zestimate®
$176/sqft
$495/mo HOA
What's special
Natural light throughoutSun-filled walk-out lower levelSpacious layoutGleaming hardwood floorsQuiet cul-de-sacAmple space for entertainingStainless steel appliances
- 42 days |
- 475 |
- 11 |
Zillow last checked:
Listing updated:
Listed by:
Mayra J. Perez (203)558-5866,
Showcase Realty, Inc. 860-274-7000
Source: Smart MLS,MLS#: 24177196
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 3
- Full bathrooms: 2
- 1/2 bathrooms: 1
Primary bedroom
- Level: Upper
Bedroom
- Level: Upper
Bedroom
- Level: Upper
Dining room
- Level: Main
Living room
- Level: Main
Heating
- Forced Air, Natural Gas
Cooling
- Central Air
Appliances
- Included: Gas Range, Refrigerator, Dishwasher, Gas Water Heater, Tankless Water Heater
Features
- Basement: Full
- Attic: Finished,Walk-up
- Has fireplace: No
Interior area
- Total structure area: 3,179
- Total interior livable area: 3,179 sqft
- Finished area above ground: 2,403
- Finished area below ground: 776
Property
Parking
- Total spaces: 1
- Parking features: Attached
- Attached garage spaces: 1
Features
- Stories: 4
- Has private pool: Yes
- Pool features: In Ground
Lot
- Features: Cul-De-Sac
Details
- Parcel number: 2547175
- Zoning: Residential
Construction
Type & style
- Home type: Condo
- Architectural style: Townhouse
- Property subtype: Condominium, Townhouse
Materials
- Vinyl Siding
Condition
- New construction: No
- Year built: 2007
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Community & HOA
Community
- Features: Basketball Court, Health Club, Playground, Tennis Court(s)
HOA
- Has HOA: Yes
- Amenities included: Clubhouse, Tennis Court(s)
- Services included: Maintenance Grounds, Trash, Snow Removal, Pest Control, Pool Service, Road Maintenance
- HOA fee: $495 monthly
Location
- Region: Middlebury
Financial & listing details
- Price per square foot: $176/sqft
- Tax assessed value: $247,300
- Annual tax amount: $8,042
- Date on market: 5/23/2026
Estimated market value
$549,900
$522,000 - $577,000
$3,821/mo
Price history
| Date | Event | Price |
|---|---|---|
| 5/23/2026 | Listed for sale | $559,900+67.1%$176/sqft |
Source:  Smart MLS #24177196 Report a problem | ||
| 11/5/2019 | Sold | $335,000$105/sqft |
Source: Smart MLS #170256661 Report a problem | ||
Public tax history
Tax history is unavailable.
Monthly payment
Est. payment$--/mo
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
See how much you could borrow to make a competitive offer.
Climate risks
Neighborhood: 06762
Nearby schools
GreatSchools rating
- 5/10Long Meadow Elementary SchoolGrades: PK-5Distance: 1.3 mi
- 8/10Memorial Middle SchoolGrades: 6-8Distance: 2.9 mi
- 8/10Pomperaug Regional High SchoolGrades: 9-12Distance: 1.7 mi
A local agent can set up tours, give advice and negotiate with sellers.
- Connecticut
- New Haven County
- Middlebury
- 06762
- 3 Winding Trail Unit 3
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Nearby zip codes
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