Seller's Agent in 2025
Jay Irvine
Serhant Connecticut, LLC
(203) 586-9459
20 in this area
80 Total Sales
18 Winding Trail Middlebury, CT 06762
3
Beds
5
Baths
4,051
Sq Ft
$515/mo
HOA Fee
Highlights
- Pool House
- Gated Community
- Deck
- Pomperaug Regional High School Rated A-
- Clubhouse
- Attic
About This Home
As of November 2025Welcome 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!
Last Agent to Sell the Property
Serhant Connecticut, LLC Brokerage Phone: (203) 586-9459 License #RES.0808291 Listed on: 08/17/2025
Townhouse Details
Home Type
- Townhome
Est. Annual Taxes
- $13,216
Year Built
- Built in 2014
HOA Fees
- $515 Monthly HOA Fees
Home Design
- Frame Construction
- Vinyl Siding
Interior Spaces
- 1 Fireplace
- Thermal Windows
- Mud Room
- Entrance Foyer
- Bonus Room
- Attic or Crawl Hatchway Insulated
Kitchen
- Built-In Oven
- Gas Cooktop
- Dishwasher
Bedrooms and Bathrooms
- 3 Bedrooms
Laundry
- Laundry Room
- Laundry on main level
- Dryer
- Washer
Finished Basement
- Heated Basement
- Walk-Out Basement
- Basement Fills Entire Space Under The House
Home Security
Parking
- 2 Car Garage
- Parking Deck
- Automatic Garage Door Opener
Pool
- Pool House
- Heated In Ground Pool
Outdoor Features
- Deck
- Patio
- Exterior Lighting
- Rain Gutters
Utilities
- Central Air
- Heating System Uses Natural Gas
- Programmable Thermostat
- Cable TV Available
Additional Features
- Accessible Ramps
- End Unit
- Property is near a golf course
Listing and Financial Details
- Assessor Parcel Number 2547194
Community Details
Overview
- Association fees include club house, grounds maintenance, trash pickup, snow removal, property management, pest control, pool service, insurance
- 270 Units
- Property managed by Imagineers
Amenities
- Clubhouse
Recreation
- Tennis Courts
- Community Basketball Court
- Community Playground
- Exercise Course
- Community Pool
Pet Policy
- Pets Allowed
Security
- Gated Community
- Storm Doors
Create a Home Valuation Report for This Property
The Home Valuation Report is an in-depth analysis detailing your home's value as well as a comparison with similar homes in the area
Home Values in the Area
Average Home Value in this Area
Property History
| Date | Event | Price | List to Sale | Price per Sq Ft | Prior Sale |
|---|---|---|---|---|---|
| 11/21/2025 11/21/25 | Sold | $695,000 | -0.7% | $172 / Sq Ft | |
| 09/22/2025 09/22/25 | Pending | -- | -- | -- | |
| 09/19/2025 09/19/25 | Price Changed | $700,000 | -3.4% | $173 / Sq Ft | |
| 08/17/2025 08/17/25 | For Sale | $725,000 | +40.0% | $179 / Sq Ft | |
| 02/11/2015 02/11/15 | Sold | $517,931 | +19.1% | $196 / Sq Ft | View Prior Sale |
| 02/15/2014 02/15/14 | For Sale | $434,995 | -- | $165 / Sq Ft | |
| 01/29/2014 01/29/14 | Pending | -- | -- | -- |
Source: SmartMLS
Tax History Compared to Growth
Agents Affiliated with this Home
-
Jay Irvine
-
Matt Rose
Buyer's Agent in 2025
Matt Rose
Keller Williams Realty
(203) 470-9115
4 in this area
375 Total Sales
-
Meredith Colasanto
Seller's Agent in 2015
Meredith Colasanto
Lamacchia Realty
(203) 577-6640
23 in this area
30 Total Sales
-
J
Buyer's Agent in 2015
Jan Hlywa
Coldwell Banker Realty
Map
Source: SmartMLS
MLS Number: 24119886
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.
Nearby Homes
- 27 Winding Trail Unit 27
- 24 Ridgewood Dr
- 2 Dogwood Ct
- 111 Dwyer Rd
- 1 Hampshire Ct
- 22 Somerset Dr
- 294 Christian Rd
- 11 Upper Whittemore Rd
- 23 Caveson Ct Unit 23
- 13 Caveson Ct
- 0 N Benson Rd Unit 47 24099635
- 0 N Benson Rd Unit 53 24086541
- 0 N Benson Rd Unit 52 24100213
- 0 N Benson Rd Unit 50 24118969
- 0 N Benson Rd Unit 44 24109951
- 0 N Benson Rd Unit 51 24117506
- 0 N Benson Rd Unit 46 24097231
- 0 N Benson Rd Unit 64 24077175
- 0 N Benson Rd Unit 48 24129196
- 0 N Benson Rd Unit 66 24093726