29 Winding Trail Unit 29 Middlebury, CT 06762
3
Beds
2.5
Baths
2,130
Sq Ft
$515/mo
HOA Fee
Highlights
- Health Club
- Pool House
- Clubhouse
- Pomperaug Regional High School Rated A-
- Open Floorplan
- Attic
About This Home
As of August 2025Beautiful luxury Portman Condo in Sought-After Ridgewood Community. Stunning 3-bed, 2.5-bath built by Toll Brothers, nestled on a private cul-de-sac in unique location. Over 2,100 sqft designed modern living space, this home includes a 4-foot bump-out for added size. Entering the home, the first floor features an open floor plan w/ hardwood floors, white cabinetry, stainless steel appliances, perfect for modern living, an upgraded skylight in kitchen floods the space with natural light. Off the kitchen is a private deck with wooded views & a large living room w/ a gas fireplace. Upstairs the spacious primary suite offers a walk-in closet and a luxurious bath with a double vanity, shower, and tub. The second bedroom also includes a walk-in closet, while the third bedroom showcases custom millwork/ built-ins for both function and style for additional utility and architectural interest. Enjoy the privacy of a wooded backyard and the convenience of a walk-out basement w/ custom storage shelves and two workbenches, woodworkers dream! Right next to the home is the "Great Meadow Lawn" adding a huge yard to play games, entertain or take a scenic stroll. Very rare location, big upgrade here $$$ . Ridgewood amenities include an outdoor pool, gym, indoor basketball court, tennis courts, a movie theater, and a clubhouse lounging area-all within walking distance. Plenty of upgrades, prime location and privacy. Don't miss this resort style must-see property! Can't build for this price!
Last Agent to Sell the Property
Serhant Connecticut, LLC License #RES.0808291 Listed on: 04/02/2025
Property Details
Home Type
- Condominium
Est. Annual Taxes
- $10,143
Year Built
- Built in 2015
HOA Fees
- $515 Monthly HOA Fees
Home Design
- Frame Construction
- Concrete Siding
- Vinyl Siding
Interior Spaces
- 2,130 Sq Ft Home
- Open Floorplan
- Self Contained Fireplace Unit Or Insert
- Thermal Windows
- Concrete Flooring
- Attic or Crawl Hatchway Insulated
- Smart Thermostat
Kitchen
- Built-In Oven
- Gas Cooktop
- Microwave
- Dishwasher
- Disposal
Bedrooms and Bathrooms
- 3 Bedrooms
Laundry
- Laundry on main level
- Electric Dryer
- Washer
Unfinished Basement
- Walk-Out Basement
- Basement Fills Entire Space Under The House
Parking
- 2 Car Garage
- Guest Parking
- Visitor Parking
Pool
- Pool House
- Heated In Ground Pool
Location
- Property is near a golf course
Utilities
- Central Air
- Heating System Uses Natural Gas
- Programmable Thermostat
- Cable TV Available
Listing and Financial Details
- Assessor Parcel Number 2547200
Community Details
Overview
- Association fees include club house, tennis, grounds maintenance, trash pickup, snow removal, property management, pest control, pool service, insurance
- 4 Units
- Property managed by Imagineers
Amenities
- Clubhouse
Recreation
- Health Club
- Tennis Courts
- Community Basketball Court
- Community Playground
- Exercise Course
- Community Pool
Pet Policy
- Pets Allowed
Similar Homes in Middlebury, CT
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Home Values in the Area
Average Home Value in this Area
Property History
| Date | Event | Price | Change | Sq Ft Price |
|---|---|---|---|---|
| 08/08/2025 08/08/25 | Sold | $520,000 | -1.9% | $244 / Sq Ft |
| 07/28/2025 07/28/25 | Pending | -- | -- | -- |
| 07/16/2025 07/16/25 | Price Changed | $530,000 | -3.6% | $249 / Sq Ft |
| 05/16/2025 05/16/25 | Price Changed | $549,900 | -2.7% | $258 / Sq Ft |
| 04/02/2025 04/02/25 | For Sale | $565,000 | +32.9% | $265 / Sq Ft |
| 11/13/2020 11/13/20 | Sold | $425,000 | -2.3% | $200 / Sq Ft |
| 09/26/2020 09/26/20 | Pending | -- | -- | -- |
| 09/21/2020 09/21/20 | Price Changed | $434,900 | -1.1% | $204 / Sq Ft |
| 08/01/2020 08/01/20 | For Sale | $439,900 | -- | $207 / Sq Ft |
Source: SmartMLS
Tax History Compared to Growth
Agents Affiliated with this Home
-
Jay Irvine
Seller's Agent in 2025
Jay Irvine
Serhant Connecticut, LLC
(203) 586-9459
22 in this area
88 Total Sales
-
Tori Withee
Buyer's Agent in 2025
Tori Withee
KW Legacy Partners
(860) 205-3182
1 in this area
6 Total Sales
-
Kate Willoughby
Seller's Agent in 2020
Kate Willoughby
Gina Jacobs Real Estate
(203) 709-1464
2 in this area
26 Total Sales
-
Tammy Papa
Buyer's Agent in 2020
Tammy Papa
Davis Owen Real Estate
(203) 526-4269
1 in this area
19 Total Sales
Map
Source: SmartMLS
MLS Number: 24085206
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