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$565,000

Ridgewood at Middlebury
27 Winding Trail 27
Middlebury, CT 06762

Condominium|Sold 01/14/2026
3
Beds
3
Total Baths
2
Full Baths
1
Partial Bath
2,130
SqFt
$265
/SqFt
2014
Built
County:
New Haven
Listing courtesy of Jay Irvine of Serhant Connecticut, LLC Office Phone: (203) 489-7800 Broker Contact: (203) 586-9459
Listing courtesy of Jay Irvine of Serhant Connecticut, LLC Office Phone: (203) 489-7800 Broker Contact: (203) 586-9459
Call Now: 1-860-573-4349
Is this the listing for you? We can help make it yours.
1-860-573-4349
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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!

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Listing Snapshot
Bedrooms 
3
Total Baths 
3
Full Baths 
2
Partial Baths 
1
Inside Area (SqFt) 
2,130 sqft
Lot Size 
N/A
Year Built 
2014
MLS® Number 
24133988
Status 
Sold
Property Tax 
$10,036
HOA/Condo/Coop Fees 
$515 monthly
Sq Ft Source 
N/A
Friends & Family
Recent Activity
2 months agoListing updated with changes from the MLS®
General Features
Attached Garage 
Yes
Garage 
Yes
Garage Spaces 
2
Levels 
Two
Parking 
Off StreetPavedDrivewayAttached
Parking Spaces 
2
Pets 
Yes
Property Sub Type 
Condominium
Security 
Security System
Sewer 
Public Sewer
SqFt Total 
2680
Style 
Townhouse
Water Source 
Public
Zoning 
PRD80
Interior Features
Appliances 
DishwasherDisposalGas CooktopMicrowaveRangeOvenGas Water Heater
Basement 
FullFinishedWalk-Out Access
Cooling 
Central Air
Fireplace 
Yes
Fireplaces 
1
Heating 
ElectricNatural GasForced Air
Media Room 
Level - Lower
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Exterior Features
Construction Details 
Vinyl SidingConcreteFrame
Lot Features 
LevelCul-De-Sac
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
Pomperaug
Listing courtesy of Jay Irvine of Serhant Connecticut, LLC Office Phone: (203) 489-7800 Broker Contact: (203) 586-9459



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Last checked: 2026-03-13 09:39 AM UTC.

Neighborhood & Commute
Source: Walkscore
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