27 Winding Trail, Unit 27, Middlebury, CT 06762
- $565,000
- 3
- BD
- 3
- BA
- 2,680
- SqFt
- Sold Price
- $565,000
- List Price
- $565,000
- Status
- CLOSED
- Days on Market
- 89
- Closing Date
- Jan 14, 2026
- MLS#
- 24133988
- Subtype
- Condo/Co-Op For Sale
- Style
- Townhouse
- Year Built
- 2014
- Bedrooms
- 3
- Bathrooms
- 3
- Full Baths
- 2
- Half Baths
- 1
- Living Area
- 2,680
- Neighborhood
- N/A
- Building Name
- Ridgewood At Middlebury
Property Description
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!
/u.realgeeks.media/davejonesrealty/logo-full.png){kind=logo}
Additional Information
- Interior Features
- Security System
- Taxes
- $10,036
- HOA Fee
- $515
- Pets Allowed
- Yes
- Building Name
- Ridgewood At Middlebury
- Property Description
- Townhouse
- Zoning
- PRD80
- Appliances
- Gas Cooktop, Range, Microwave, Dishwasher, Disposal
- Heating
- Hot Air
- Air Conditioning
- Central Air
- Pool
- Yes
- Parking Features
- Attached, Paved, Off Street, Driveway
- Garage Spaces
- 2
- Elementary School
- Per Board of Ed
- High School
- Pomperaug
Listing courtesy of Jay Irvine from Serhant Connecticut, LLC. (203) 586-9459 (203) 489-7800
Selling Office: William Raveis Real Estate.Mortgage Calculator
The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.