27 Winding Trail Unit 27 Middlebury, CT 06762
Estimated payment $4,338/month
Highlights
- Heated In Ground Pool
- Clubhouse
- 1 Fireplace
- Pomperaug Regional High School Rated A-
- Attic
- Tennis Courts
About This Home
Beautiful 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!
Listing Agent
Serhant Connecticut, LLC Brokerage Phone: (203) 586-9459 License #RES.0808291 Listed on: 10/17/2025

Property Details
Home Type
- Condominium
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 a 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
Map
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 |
---|---|---|---|---|---|
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
MLS Number: 24133988

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