18 Winding Trail 18, Middlebury, Connecticut

$700,000

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3

Beds

5

Baths

4,051

Square feet

About 18 Winding Trail 18

Welcome to this luxury home w/ custom features never seen before! This 4000+ sqft, 3 BEDROOM SUITES, 3.2 bath has elegance and comfort, built w/ never seen upgrades. On the most sought-after private cul-de-sac St. and the best location in the complex. Enter through a grand two-story foyer with gleaming hardwood floors, cathedral ceilings & soaring windows that fill the home with natural light. Beautiful curves staircase, formal living & dining rooms set the stage for entertaining. The gourmet kitchen boasts granite counters, beautiful cabinets, stainless steel appliances, gas cooktop, tile backsplash, large island for ample prep space, a chefs dream. The family room has vaulted ceilings & gas fireplace creates the ultimate gathering space. Rare floor plan features three bedroom suites: a main-level primary with tray ceiling, dual walk-in closets, spa-like ensuite with soaking tub & shower, plus two additional suites upstairs that each have THEIR OWN BATHROOM. Oversized loft overlooks the main floor. Finished walkout basement adds a rec/play room with a custom wet bar w/ granite counters & white cabinets, media area or office, half bath (potential for lower in law/ 4th bedroom). Highlights: laundry w/ sink, additional gas hookup in basement for fireplace, finished lower patio, upper deck & full wheelchair accessibility. Largest backyard in community, great for entertaining or playing sports. Clubhouse w/ bar, pool, gym, tennis crt, indoor basketball court! This is a MUST see!

Features of 18 Winding Trail 18

MLS® # 24119886
Price $700,000
Bedrooms 3
Bathrooms 5.00
Full Baths 3
Half Baths 2
Square Footage 4,051
Type Condo/Co-Op For Sale
Sub-Type Condominium
Style Townhouse
Status Under Contract

Community Information

Address 18 Winding Trail 18
Area N/A
City Middlebury
County New Haven
State Connecticut
Zip Code 06762

Amenities

Amenities Basketball Court, Club House, Exercise Room/Health Club, Playground/Tot Lot, Pool, Tennis Courts
Features Programmable Thermostat, Storm Doors, Thermopane Windows
Parking Spaces 4
Parking Attached Garage, Covered Garage, Paved, Driveway
# of Garages 2
Is Waterfront No
Waterfront Not Applicable
Has Pool Yes
Pool Heated, Pool House, In Ground Pool

Interior

Interior Features Auto Garage Door Opener, Cable - Pre-wired
Appliances Gas Cooktop, Wall Oven, Refrigerator, Dishwasher, Washer, Dryer
Heating Hot Air, Natural Gas
Cooling Central Air
Fireplace Yes
# of Fireplaces 1
# of Stories 3
Has Basement Yes
Basement Full, Heated, Fully Finished, Cooled, Walk-out, Liveable Space, Full With Walk-Out

Exterior

Exterior Vinyl Siding
Exterior Features Sidewalk, Deck, Gutters, Lighting, Patio
Lot Description Secluded, Lightly Wooded, Level Lot, On Cul-De-Sac

School Information

Elementary Per Board of Ed
High Per Board of Ed

Additional Information

Date Listed August 17th, 2025
Days on Market 35
Zoning RES
RE / Bank Owned No
HOA Fees 515
HOA Fees Freq. Monthly

Listing Details

OfficeSerhant Connecticut, LLC

Listing Map

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Listing information last updated on October 18th, 2025 at 8:04am EDT.