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$695,000
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Property Description
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!
Full Property Details
Full Property Details for 18 Winding Trail #18
General
- Sold For: $695,000
- HOA FEE: $515/month
- Taxes: (July 2025-June 2026)
- Status: Closed
- Type: Townhouse
- Source: SMARTMLS
- MLS ID: 24119886
- Added to Site: 153 day(s) ago
Interior
- Number of Rooms: 10
- Rooms/Areas: Bonus Room, Foyer, Laundry Room, Mud Room
- Interior Features: Auto Garage Door Opener, Cable - Pre-wired
- Fireplace: Yes
- Number of Fireplaces: 1
- Appliances: Gas Cooktop, Wall Oven, Refrigerator, Dishwasher, Washer, Dryer
Rooms
Bathrooms
- Total Bathrooms: 5
- Full Bathrooms: 3
- Half Bathrooms: 2
Bedrooms
- Total Bedrooms: 3
- Primary Bedroom: Primary Bedroom - Bedroom Suite, Ceiling Fan, Full Bath, Walk-In Closet, Wall/Wall Carpet, 16 x 13, Upper
- Primary Suite: 9 ft+ Ceilings, Bedroom Suite, Full Bath, Walk-In Clo, 20 x 12, Main
- Primary Bedroom 2: Primary Bedroom - Bedroom Suite, Ceiling Fan, Full Bath, Walk-In Closet, Wall/Wall Carpet, 16 x 13, Upper
Other Rooms
- Living Room: Living Room - 2 Story Window(s), 9 ft+ Ceilings, Cathedral Ceiling, Hardwood Floor, 13 x 11, Main
- Family Room: Family Room - 9 ft+ Ceilings, Balcony/Deck, Ceiling Fan, Gas Log Fireplace, Sliders, Hardwood Floor, 20 x 16, Main
- Eat In Kitchen: Eat-In Kitchen - 9 ft+ Ceilings, Breakfast Bar, Granite Counters, Dining Area, , 17 x 13, Main
- Dining Room: Dining Room - 2 Story Window(s), 9 ft+ Ceilings, Cathedral Ceiling, Hardwood Floor, 16.2 x 11, Main
- Loft: Loft - Full Bath, Wall/Wall Carpet, Upper
- Game room: Yes
- Game Room: Rec/Play Room - Wall/Wall Carpet, Lower
- Rec Room: Wall/Wall Carpet, Lower
- Theater/Media: Media Room - Remodeled, Wet Bar, Half Bath, Sliders, Wall/Wall Carpet, Lower
- Laundry: Main Level
Additional Information
- Shared Amenities: Basketball Court, Club House, Exercise Room/Health Club, Playground/Tot Lot, Pool, Tennis Courts
- Pool: Yes
- Pool Description: Heated, Pool House, In Ground Pool
Exterior
- Exterior Features: Sidewalk, Deck, Gutters, Lighting, Patio
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 2
- Total Spaces: 4
- Parking: Attached Garage, Covered Garage, Paved, Driveway
Location
- County: New Haven
- Complex: Ridgewood at Middlebury
- Driving Directions: Ridgewood Drive to winding Trail
School Information
- Elementary School: Per Board of Ed
- High School: Per Board of Ed
Community
- Gated community: Yes
- Association: Yes
- Home Owners Assn.: 1
- Assoc. Fees Include: Club House, Grounds Maintenance, Trash Pickup, Snow Removal, Property Management, Pest Control, Pool Service, Insurance
- Pets Allowed: Yes
- Pet Restrictions: No restrictions
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Hot Air, Natural Gas
- Heating Fuel: Natural Gas
- Water Heater: Natural Gas, Domestic
Utilities
- Sewer: Public Sewer Connected
- Water: Public Water Connected
Structural Information
- Architectural Style: Townhouse
- Description/Design: Gated Community
- Model: Bucknell Premium
- Construction Status: No/Resale
- Exterior Const.: Vinyl Siding
- Basement Desc.: Full, Heated, Fully Finished, Cooled, Walk-out, Liveable Space, Full With Walk-Out
- Attic: Yes
- Disability Access: Ramps
- Unit on End: Yes
- Square Feet: 4,051
- Above Ground: 2,688 Sq. Ft.
- Below Ground: 1,363 Sq. Ft.
- Year Built: 2014
Lot Features
- Zoning: RES
- Lot Description: Secluded, Lightly Wooded, Level Lot, On Cul-De-Sac
Green Features
- Energy Features: Programmable Thermostat, Storm Doors, Thermopane Windows
Financial Considerations
- Association Fee: $515
- Assoc Fee Freq.: Monthly
- Assessment Amount: $406,400
- Tax Year: July 2025-June 2026
Disclosures and Reports
- Property ID: 2547194
Listed by Serhant Connecticut, LLC, WKND.R Team At SERHANT, Jay Irvine
Sold by Keller Williams Realty, Matt Rose Team, Matt Rose
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Schools
Schools serving 18 Winding Trail #18
School District:Regional School District 15
| Name | Grades | Distance |
|---|---|---|
Long Meadow Elementary School 65 North Benson Road, Middlebury, CT 06762 | PK-5 | 1.3 mi |
Memorial Middle School, Middlebury, CT 1 Memorial Drive, Middlebury, CT 06762 | 6-8 | 2.8 mi |
Pomperaug Regional High School 234 Judd Road, Southbury, CT 06488 | 9-12 | 1.8 mi |
Disclaimer:
School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 18 Winding Trail #18
Date
Details
Price
Change
Source
11/21/2025
Sold
$695,000
-0.71%
MLS
9/19/2025
Price Reduced
$700,000
-3.45%
MLS
8/17/2025
Listed
$725,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
18 Winding Trail #18, Middlebury, CT 06762 (MLS# 24119886) is a Townhouse property that was sold at $695,000 on November 21, 2025. Want to learn more about 18 Winding Trail #18? Do you have questions about finding other Townhouse real estate for sale in Middlebury? You can browse all Middlebury real estate or contact a Coldwell Banker agent to request more information.

