27 Winding Trail 27
Courtesy of Serhant Connecticut, LLC
Sold

27 Winding Trail 27

27 Winding Trail Unit: 27, Middlebury, CT 06762

$565,000
Beautiful Luxury Portman Condo in the Sought-After Ridgewood Community! This stunning 3-bed, 2.5-bath home by Toll Brothers is perfectly situated on a private cul-de-sac in one of Ridgewood's most desirable and unique locations. Offering over 2,680 SqFt of beautifully designed living space, this residence includes a rare 4-ft bump-out for added size plus a finished walk-out basement. The main level features an open floor plan with gleaming hardwood floors, custom cabinetry, stainless steel appliances, and marble countertops-perfect for modern entertaining. An upgraded skylight fills the kitchen with natural light, while sliding doors lead to a private deck with tranquil wooded views. The spacious living room highlights a gas fireplace with a stone veneer surround and rich wood mantle. Upstairs, entire 2nd level has upgraded designer hardwood flrs. Primary suite impresses with a walk-in closet and a spa-like bath w/ a double vanity, soaking tub, and separate shower. Two additional bedrooms include generous closets & soaring ceilings. The remodeled finished walk out basement is great for a media/ entertainment room. Enjoy the rare privacy of a wooded backdrop and direct access to the expansive "Great Meadow Lawn" next door-ideal for gatherings, games, or a peaceful stroll. Resort-style amenities include an outdoor pool, gym, tennis and basketball courts, movie theater, and clubhouse-all within walking distance. You can't build this home for the price, an absolute must-see!

3
beds

3
baths

2,680 Sq.Ft. LIVING AREA

Features & Amenities

Interior

  • total bedrooms3
  • Total bathrooms3
  • full bathrooms2
  • half bathroom1
  • Laundry room Upper Level
  • APPLIANCES Gas Cooktop, Oven/Range, Microwave, Dishwasher, Disposal
  • other interior Features Cable - Pre-wired, Security System

Area & Lot

  • Status Sold
  • Date Sold January 14, 2026
  • Living Area2,680 Sq.Ft.
  • Total Area2,680 Sq.Ft.
  • MLS® ID24133988
  • TypeCondo
  • YEAR BUILT2014
  • Architecture StylesTownhouse
  • Water FrontageNot Applicable
  • Elementary SchoolPer Board of Ed
  • High SchoolPomperaug

Exterior

  • STORIES2
  • Garage Space2.0
  • water SourcePublic Water Connected
  • PoolHeated, In Ground Pool
  • lot featuresLightly Wooded, Level Lot, On Cul-De-Sac
  • parkingAttached Garage, Paved, Off Street Parking, Driveway
  • HEAT TYPEHot Air
  • AIR CONDITIONINGCentral Air
  • sewerPublic Sewer Connected
  • HOA AmenitiesBasketball Court, Club House, Exercise Room/Health Club, Playground/Tot Lot, Pool, Tennis Courts

Financial

  • Sales Price$565,000
  • Real Estate Tax $10,036/yr
  • HOA $515/mo
  • Zoning PRD80

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