x
Showing 1 of 0
X
Save

27 Winding Trail 27
Middlebury CT 06762 US

$565,000

Active Under Contract Listing ID 24133988
bed icon
3 bed
bath icon
3.00 Bath (2 Full , 1 Half)
home icon
Condominium

$565,000

Active Under Contract Listing ID 24133988
Save

27 Winding Trail 27 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!

Collapse all

Property Features

  • Facts
  • Property Type: Residential
  • Property Sub-type: Condominium
  • Features
  • Full Bathrooms: 2
  • 1/2 Bathrooms: 1
  • Cooling System: Central Air
  • Heating Fuels: Electric (Heating), Fireplace(s), Natural Gas
  • Additional Features
  • Fireplace

School Information

  • School
  • Per Board of Ed(Elementary)
  • Pomperaug(HighSchool)

Property

  • propertytype: Residential
  • propertysubtype: Condominium
  • listprice: 565000
  • unparsedaddress: 27 Winding Trail
  • unitnumber: 27
  • postalcity: Middlebury
  • stateorprovince: CT
  • country: US
  • postalcode: 06762
  • bathroomsfull: 2
  • bathroomshalf: 1
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeunits: Acres
  • livingarea: 2680
  • livingareaunits: Square Feet
  • listagentfullname: Jay Irvine
  • listagentemail: realtor.j.irvine@gmail.com
  • listagentkey: 3yd-CTMLS-IRVINEJ
  • listagentmlsid: IRVINEJ
  • listagentpreferredphone: 2035869459
  • listagentofficephone: 2034897800
  • listofficekey: 3yd-CTMLS-13541
  • listofficemlsid: 13541
  • disclaimer: Copyright © 2025 SmartMLS, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
  • sourcesystemid: CTMLS
  • yearbuilt: 2014
  • listingcontractdate: 2025-10-17
  • listagenturl: https://serhant.com/
  • countyorparish: New Haven
  • parcelnumber: 2547199
  • elementaryschool: Per Board of Ed
  • highschool: Pomperaug
  • appliances: Cooktop, Cooktop - Gas, Dishwasher, Garbage Disposer, Microwave, Range, Washer
  • cooling: Central Air
  • constructionmaterials: Vinyl Siding
  • heating: Electric (Heating), Fireplace(s), Natural Gas
  • fireplaceyn: True
  • transactiontype: ForSale
  • storiestotal: 0
  • parkingtotal: 2
  • parkingfeatures: Driveway, Garage, Garage - Attached, Paved or Surfaced
  • waterfrontyn: False
  • interiorfeatures: Programmable Thermostat, Thermopane Windows, Cable - Pre-wired, Security System
  • architecturalstyle: Other
  • rooms: Basement, Bathroom 1, Bathroom 2, Bathroom 3, Bedroom 1, Bedroom 2, Bedroom 3
  • securityfeatures: Security System
  • dock: False
  • poolprivateyn: False
  • spayn: False
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: True
  • internetconsumercommentyn: True
  • customfields: {"AdditionalInformation":{}, "AlternatePrices":[], "BrokerName":"SERHANT CONNECTICUT LLC", "BuilderEmail":null, "BuilderFax":null, "BuilderPhone":null, "City":null, "Country":null, "Expenses":[{"ExpenseCategory":"Home Owner Assessments Fee", "ExpenseFrequency":"Monthly", "ExpenseValue":515}], "GeocodeOptions":null, "LeadRoutingEmail":"realtor.j.irvine@gmail.com", "ListBrokerageCity":"New York", "ListBrokerageCountry":"US", "ListBrokerageEmail":"hello@serhant.com", "ListBrokerageLogoUrl":null, "ListBrokerageName":"SERHANT CONNECTICUT LLC", "ListBrokeragePhone":"(646) 480-7665", "ListBrokeragePostalCode":"10012", "ListBrokerageStateOrProvince":"NY", "ListBrokerageUnitNumber":null, "ListBrokerageUnparsedAddress":"372 W Broadway", "ListBrokerageWebsiteUrl":"https://serhant.com/", "ListOfficeAddress1":"372 W Broadway", "ListOfficeAddress2":null, "ListOfficeBrokerMlsId":null, "ListOfficeCity":"Greenwich", "ListOfficeCountry":"US", "ListOfficeEmail":"hello@serhant.com", "ListOfficePostalCode":"06830", "ListOfficeStateOrProvince":"CT", "ListPriceCurrencyType":"USD", "ListingTitle":"Townhouse, Condominium - Middlebury, CT", "ListingURL":"https://www.realtor.com/realestateandhomes-detail/27-Winding-Trl_Middlebury_CT_06762_M32788-95262?f=listhub&s=CTMLS&m=24133988&c=rexren", "MLSModificationTimestamp":"2025-11-03T20:31:33Z", "Neighborhoods":[{"Description":null, "Name":"N/A"}], "PostalCode":null, "RawPropertySubType":"Condominium", "RawPropertyType":"Condo/Co-Op For Sale", "RoomCount":null, "StateOrProvince":null, "Taxes":[], "UnitNumber":null, "UnparsedAddress":null}
Listing Changed: 11/19/2025 3:09:31 AM GMT
Source Updated Date: 12/17/2025 1:04:02 PM GMT

Courtesy of: Jay Irvine, Serhant Connecticut, LLC, realtor.j.irvine@gmail.com

Copyright © 2025 SmartMLS, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.