$565,000

27 Winding Trail Unit 27 Middlebury, CT 06762

Estimated payment $4,338/month

Total Views 146
3 Beds
2.5 Baths
2,680 Sq Ft
$211 Price per Sq Ft

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

Jay Irvine

Serhant Connecticut, LLC Brokerage Phone: (203) 586-9459 License #RES.0808291 Listed on: 10/17/2025

Serhant Connecticut, LLC

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

Property Details

Home Type

Condominium

Est. Annual Taxes

$10,036

Year Built

Built in 2014

Lot Details

0

HOA Fees

$515 per month

Listing Details

  • Neighborhood: N/A
  • Property Type: Condo/Co-Op For Sale
  • Style: Townhouse
  • Sq Ft Est Heated Above Grade: 2130
  • Sq Ft Est Heated Below Grade: 550
  • Total Sq Ft: 2680
  • Year Built: 2014
  • New Construction: No/Resale
  • Nearby Amenities: Golf Course, Health Club, Lake, Medical Facilities, Park, Playground/Tot Lot, Private School(s)
  • Association Amenities: Basketball Court, Club House, Exercise Room/Health Club, Playground/Tot Lot, Pool, Tennis Courts
  • Property Sub Type: Condominium
  • Direct Waterfront: No
  • End Unit: No
  • Home Warranty Offered: No
  • Radon Mitigation Air Ynu: No
  • Special Assessment Details: $115/mo capital contribution till 12/25
  • Condo Model Name: Portman
  • Directions: GPS
  • Spec Assoc Asses: Yes
  • Street Type: Trail
  • Special Features: None

Interior Features

  • Total Bedrooms: 3
  • Total Bathrooms: 3
  • Full Bathrooms: 2
  • Half Bathrooms: 1
  • Fireplaces: 1
  • Attic Description: Crawl Space, Access Via Hatch
  • Basement Description: Full, Heated, Fully Finished, Walk-out, Liveable Space, Full With Walk-Out
  • Interior Amenities: Cable - Pre-wired, Security System
  • Appliances: Gas Cooktop, Oven/Range, Microwave, Dishwasher, Disposal
  • Laundry Room Info: Upper Level
  • Attic: Yes

Exterior Features

  • Exterior Siding: Vinyl Siding
  • Waterfront Description: Not Applicable
  • Swimming Pool: Yes
  • Pool: Heated, In Ground Pool
  • Construction Description: Frame, Concrete

Garage/Parking

  • Garages Number: 2
  • Total Parking Spaces: 2
  • Garage And Parking: Attached Garage, Driveway, Paved, Off Street Parking

Utilities

  • Cooling System: Central Air
  • Heat Type: Hot Air
  • Heat Fuel Type: Natural Gas
  • Hot Water Description: Natural Gas, Domestic
  • Water Source: Public Water Connected
  • Sewer: Public Sewer Connected

Condo/Co-op/Association

  • Association Fee Includes: Club House, Tennis, Grounds Maintenance, Trash Pickup, Snow Removal, Property Management, Pest Control, Pool Service, Insurance
  • HOA Fees: 515
  • HOA Fee Frequency: Monthly
  • Property Management Type: Professional-Off Site
  • Property Mgt Company Name: Imagineers
  • Total Number of Units In Complex: Ridgewood at Middlebury

Green Features

  • Energy Features: Programmable Thermostat, Thermopane Windows

Lot Info

  • Lot Description: Lightly Wooded Level Lot On Cul-De-Sac
  • Flood Zone: No
  • Zoning: PRD80
  • Parcel #: 2547199

Rental Info

  • Pets Allowed Info: No restrictions
  • Pets Allowed: Yes

Multi Family

  • Total Number Of Units: 270

Tax Info

  • Tax Year: July 2025-June 2026
  • Property Tax: 10036

MLS Schools

  • Elementary School: Per Board of Ed
  • High School: Pomperaug

Map

Range of Values:

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Home Values in the Area

Source: Public Records

Average Home Value in this Area





Source: Public Records

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

Source: SmartMLS

MLS Number: 24133988

SmartMLS