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$565,000
New Listing

Ridgewood at Middlebury
29 Winding Trail 29
Middlebury, CT 06762

For Sale|Townhouse|Active
3
Beds
2
Full Baths
1
Partial Bath
2,130
SqFt
$265
/SqFt
2015
Built
County:
New Haven
Listing courtesy of Jay Irvine of Serhant Connecticut, LLC
Call Now: 860.406.4060
Is this the home for you? We can help make it yours.
860.406.4060
29 Winding Trail 2929 Winding Trail 2929 Winding Trail 2929 Winding Trail 29
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Monthly Payment (Est.)

$2,578
Calculator powered by Showcase IDX, a Constellation1 Company. Copyright ©2025 Information is deemed reliable but not guaranteed.

Beautiful Portman Condo in Sought-After Ridgewood Community. Stunning 3-bed, 2.5-bath condo built by Toll Brothers, nestled on a private cul-de-sac in unique location. Over 2,100 sqft designed modern living space, this home includes a 4-foot bump-out for added size. Entering the home, the first floor features an open floor plan w/ hardwood floors, white cabinetry, stainless steel appliances, perfect for modern living, an upgraded skylight in kitchen floods the space with natural light. Off the kitchen is a private deck with wooded views & a large living room w/ a gas fireplace. Upstairs the spacious primary suite offers a walk-in closet and a luxurious bath with a double vanity, shower, and tub. The second bedroom also includes a walk-in closet, while the third bedroom showcases custom millwork/ built-ins for both function and style for additional utility and architectural interest. Enjoy the privacy of a wooded backyard and the convenience of a walk-out basement w/ custom storage shelves and two workbenches, woodworkers dream! Right next to the home is the "Great Meadow Lawn" adding a huge yard to play games, entertain or take a scenic stroll. Very rare location, big upgrade here $$$ . Ridgewood amenities include an outdoor pool, gym, indoor basketball court, tennis courts, a movie theater, and a clubhouse lounging area-all within walking distance. Plenty of upgrades, prime location and privacy. Don't miss this must-see property! Can't build for this price!

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Listing Snapshot
Price 
$565,000
Days On Site 
0 Days
Bedrooms 
3
Inside Area (SqFt) 
2,130 sqft
Total Baths 
3
Full Baths 
2
Partial Baths 
1
Lot Size 
N/A
Year Built 
2015
MLS® Number 
24085206
Status 
Active
Property Tax 
$10,168
HOA/Condo/Coop Fees 
$515 monthly
Sq Ft Source 
N/A
Friends & Family
Recent Activity
22 hours agoListing updated with changes from the MLS®
22 hours agoListing first seen on site
General Features
Attached Garage 
Yes
Garage 
Yes
Garage Spaces 
2
Parking 
PavedAttached
Parking Spaces 
4
Pets 
Yes
Property Sub Type 
Townhouse
Sewer 
Public Sewer
SqFt Total 
2130
Stories 
Three Or More
Style 
Townhouse
Water Source 
Public
Zoning 
PRD80
Interior Features
Appliances 
DishwasherDisposalDryerGas CooktopMicrowaveRefrigeratorOvenWasherGas Water Heater
Basement 
FullWalk-Out AccessUnfinishedConcrete
Cooling 
Central Air
Fireplace 
Yes
Fireplaces 
1
Heating 
Fireplace InsertNatural GasForced Air
Interior 
Open Floorplan
Laundry Features 
Main Level
Living Room 
Dimensions - 17 x 15.7Level - Main
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Exterior Features
Construction Details 
Vinyl SidingConcreteFrame
Lot Features 
Cul-De-Sac
Other Structures 
Pool House
Pool Features 
HeatedOutdoor PoolIn Ground
Community Features
Association Amenities 
ClubhousePoolBasketball CourtPlaygroundTennis Court(s)
Association Dues 
515
Community Features 
Tennis Court(s)Golf
HOA Fee Frequency 
Monthly
Schools
School District
Unknown
Elementary School
Per Board of Ed
Middle School
Unknown
High School
Per Board of Ed
Listing courtesy of Jay Irvine of Serhant Connecticut, LLC



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 2025 SmartMLS, Inc.

Neighborhood & Commute
Source: Walkscore
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