Seller's Agent in 2026
Jay Irvine
Serhant Connecticut, LLC
(203) 586-9459
21 in this area
82 Total Sales
27 Winding Trail Unit 27 Middlebury, CT 06762
3
Beds
2.5
Baths
2,680
Sq Ft
$515/ mo
HOA Fee
Highlights
- Heated In Ground Pool
- Clubhouse
- 1 Fireplace
- Pomperaug Regional High School Rated A
- Attic
- Tennis Courts
About This Home
As of January 2026Beautiful 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!
Last Agent to Sell the Property
Serhant Connecticut, LLC Brokerage Phone: (203) 586-9459 License #RES.0808291 Listed on: 10/17/2025
Townhouse Details
Home Type
- Townhome
Est. Annual Taxes
- $10,036
Year Built
- Built in 2014
HOA Fees
- $515 Monthly HOA Fees
Parking
- 2 Car Garage
Home Design
- Frame Construction
- Concrete Siding
- Vinyl Siding
Interior Spaces
- 1 Fireplace
- Thermal Windows
- Attic or Crawl Hatchway Insulated
- Home Security System
- Laundry on upper level
Kitchen
- Oven or Range
- Gas Cooktop
- Microwave
- Dishwasher
- Disposal
Bedrooms and Bathrooms
- 3 Bedrooms
Finished Basement
- Heated Basement
- Walk-Out Basement
- Basement Fills Entire Space Under The House
- Crawl Space
Schools
- Pomperaug High School
Utilities
- Central Air
- Heating System Uses Natural Gas
- Programmable Thermostat
- Cable TV Available
Additional Features
- Heated In Ground Pool
- Property is near golf course
Listing and Financial Details
- Assessor Parcel Number 2547199
Community Details
Overview
- Association fees include club house, tennis, 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
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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 |
|---|---|---|---|---|---|
| 01/17/2026 01/17/26 | Pending | -- | -- | -- | |
| 01/14/2026 01/14/26 | Sold | $565,000 | 0.0% | $211 / Sq Ft | |
| 10/17/2025 10/17/25 | For Sale | $565,000 | +18.9% | $211 / Sq Ft | |
| 06/27/2022 06/27/22 | Sold | $475,000 | +2.2% | $223 / Sq Ft | View Prior Sale |
| 06/11/2022 06/11/22 | Pending | -- | -- | -- | |
| 03/13/2022 03/13/22 | For Sale | $465,000 | +30.6% | $218 / Sq Ft | |
| 03/15/2019 03/15/19 | Sold | $356,000 | -1.1% | $167 / Sq Ft | View Prior Sale |
| 01/21/2019 01/21/19 | Pending | -- | -- | -- | |
| 11/14/2018 11/14/18 | For Sale | $359,975 | -- | $169 / Sq Ft |
Source: SmartMLS
Agents Affiliated with this Home
-
Jay Irvine
-
Tricia Lougal
T
Buyer's Agent in 2026
Tricia Lougal
William Raveis Real Estate
(203) 481-4571
1 in this area
4 Total Sales
-
Katie Westrin
Buyer Co-Listing Agent in 2026
Katie Westrin
William Raveis Real Estate
(203) 509-3619
1 in this area
155 Total Sales
-
Mary Ann Bennett
Seller's Agent in 2022
Mary Ann Bennett
Drakeley Real Estate, Inc.
(203) 206-7048
6 in this area
133 Total Sales
-
B
Buyer's Agent in 2022
Blair Patterson
William Raveis Real Estate
-
Connie Pereira
Seller's Agent in 2019
Connie Pereira
RE/MAX
(203) 558-4440
77 Total Sales
Map
Source: SmartMLS
MLS Number: 24133988
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.
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