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!
Sold for $695,000
$695,000
18 Winding Trail #18, Middlebury, CT 06762
3beds
4,051sqft
Condominium, Townhouse
Built in 2014
-- sqft lot
$721,700 Zestimate®
$172/sqft
$5,254 Estimated rent
Home value
$721,700
$642,000 - $808,000
$5,254/mo
Zestimate® history
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List your homeWhat's special
Gas fireplaceSpa-like ensuiteSoaking tubUpper deckAdditional suites upstairsVaulted ceilingsPrivate cul-de-sac
Zillow last checked:
Listing updated:
Listed by:
WKND.R Team At SERHANT,
Jay Irvine (203)586-9459,
Serhant Connecticut, LLC 203-489-7800
Bought with:
Matt Rose, REB.0584501
Keller Williams Realty
Source: Smart MLS,MLS#: 24119886
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 5
- Full bathrooms: 3
- 1/2 bathrooms: 2
Rooms
- Room types: Bonus Room, Laundry
Primary bedroom
- Features: High Ceilings, Bedroom Suite, Full Bath, Walk-In Closet(s), Wall/Wall Carpet
- Level: Main
- Area: 240 Square Feet
- Dimensions: 12 x 20
Primary bedroom
- Features: Bedroom Suite, Ceiling Fan(s), Full Bath, Walk-In Closet(s), Wall/Wall Carpet
- Level: Upper
- Area: 208 Square Feet
- Dimensions: 13 x 16
Primary bedroom
- Features: Bedroom Suite, Ceiling Fan(s), Full Bath, Walk-In Closet(s), Wall/Wall Carpet
- Level: Upper
- Area: 208 Square Feet
- Dimensions: 13 x 16
Dining room
- Features: 2 Story Window(s), High Ceilings, Cathedral Ceiling(s), Hardwood Floor
- Level: Main
- Area: 178.2 Square Feet
- Dimensions: 11 x 16.2
Family room
- Features: High Ceilings, Balcony/Deck, Ceiling Fan(s), Gas Log Fireplace, Sliders, Hardwood Floor
- Level: Main
- Area: 320 Square Feet
- Dimensions: 16 x 20
Kitchen
- Features: High Ceilings, Breakfast Bar, Granite Counters, Dining Area, Kitchen Island, Hardwood Floor
- Level: Main
- Area: 221 Square Feet
- Dimensions: 13 x 17
Living room
- Features: 2 Story Window(s), High Ceilings, Cathedral Ceiling(s), Hardwood Floor
- Level: Main
- Area: 143 Square Feet
- Dimensions: 11 x 13
Loft
- Features: Full Bath, Wall/Wall Carpet
- Level: Upper
Media room
- Features: Remodeled, Wet Bar, Half Bath, Sliders, Wall/Wall Carpet
- Level: Lower
Rec play room
- Features: Wall/Wall Carpet
- Level: Lower
Heating
- Forced Air, Natural Gas
Cooling
- Central Air
Appliances
- Included: Gas Cooktop, Oven, Refrigerator, Dishwasher, Washer, Dryer, Gas Water Heater, Water Heater
- Laundry: Main Level, Mud Room
Features
- Wired for Data, Entrance Foyer
- Doors: Storm Door(s)
- Windows: Thermopane Windows
- Basement: Full,Heated,Finished,Cooled,Walk-Out Access,Liveable Space
- Attic: Access Via Hatch
- Number of fireplaces: 1
- Common walls with other units/homes: End Unit
Interior area
- Total structure area: 4,051
- Total interior livable area: 4,051 sqft
- Finished area above ground: 2,688
- Finished area below ground: 1,363
Property
Parking
- Total spaces: 4
- Parking features: Attached, Covered, Paved, Driveway, Garage Door Opener
- Attached garage spaces: 2
- Has uncovered spaces: Yes
Accessibility
- Accessibility features: Accessible Approach with Ramp
Features
- Stories: 3
- Patio & porch: Deck, Patio
- Exterior features: Sidewalk, Rain Gutters, Lighting
- Has private pool: Yes
- Pool features: Heated, In Ground
Lot
- Features: Secluded, Few Trees, Level, Cul-De-Sac
Details
- Additional structures: Pool House
- Parcel number: 2547194
- Zoning: RES
Construction
Type & style
- Home type: Condo
- Architectural style: Townhouse
- Property subtype: Condominium, Townhouse
- Attached to another structure: Yes
Materials
- Vinyl Siding
Condition
- New construction: No
- Year built: 2014
Details
- Builder model: Bucknell Premium
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Green energy
- Energy efficient items: Thermostat, Doors, Windows
Community & HOA
Community
- Features: Gated, Basketball Court, Golf, Health Club, Lake, Park, Playground
HOA
- Has HOA: Yes
- Amenities included: Basketball Court, Clubhouse, Exercise Room/Health Club, Playground, Pool, Tennis Court(s), Management
- Services included: Maintenance Grounds, Trash, Snow Removal, Pest Control, Pool Service, Insurance
- HOA fee: $515 monthly
Location
- Region: Middlebury
Financial & listing details
- Price per square foot: $172/sqft
- Tax assessed value: $406,400
- Annual tax amount: $13,216
- Date on market: 8/17/2025
Price history
| Date | Event | Price |
|---|---|---|
| 11/21/2025 | Sold | $695,000-0.7%$172/sqft |
Source:  Smart MLS #24119886 Report a problem | ||
| 9/22/2025 | Pending sale | $700,000$173/sqft |
Source: Smart MLS #24119886 Report a problem | ||
| 9/19/2025 | Price change | $700,000-3.4%$173/sqft |
Source: Smart MLS #24119886 Report a problem | ||
| 8/17/2025 | Listed for sale | $725,000$179/sqft |
Source: Smart MLS #24119886 Report a problem | ||
Public tax history
Tax history is unavailable.
Neighborhood: 06762
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Nearby schools
GreatSchools rating
- 5/10Long Meadow Elementary SchoolGrades: PK-5Distance: 1.3 mi
- 8/10Memorial Middle SchoolGrades: 6-8Distance: 2.8 mi
- 8/10Pomperaug Regional High SchoolGrades: 9-12Distance: 1.8 mi
Sell for more on Zillow
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$721,700
2% more
+$14,434
With Zillow Showcase(estimated)
$736,134
Sell for more on Zillow
Get a Zillow Showcase℠ listing at no additional cost and you could sell for .
$721,700
2% more
+$14,434
With Zillow Showcase(estimated)
$736,134
- Connecticut
- New Haven County
- Middlebury
- 06762
- 18 Winding Trail Unit 18
