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$565,000

  • Sold
  • Closed
  • Townhouse
  • 3 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 2,680 Sq. Ft.
  • 2 Car Garage
  • Updated 5 hours ago
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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!

Full Property Details for 27 Winding Trail #27

General

  • Sold For: $565,000
  • HOA FEE: $515/month
  • Taxes: (July 2025-June 2026)
  • Status: Closed
  • Type: Townhouse
  • Source: SMARTMLS
  • MLS ID: 24133988
  • Added to Site: 92 day(s) ago

Interior

  • Number of Rooms: 9
  • Interior Features: Cable - Pre-wired, Security System
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Appliances: Gas Cooktop, Oven/Range, Microwave, Dishwasher, Disposal

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 2
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 3
  • Primary Suite: Vaulted Ceiling, Bedroom Suite, Full Bath, Walk-In Cl, 17 x 17, Upper
  • Bedroom 1: Bedroom - 9 ft+ Ceilings, Hardwood Floor, 13 x 13, Upper
  • Bedroom 2: Bedroom - Vaulted Ceiling, Hardwood Floor, 13 x 13, Upper

Other Rooms

  • Living Room: Living Room - 9 ft+ Ceilings, Combination Liv/Din Rm, Gas Log Fireplace, Hardwood Floor, 17 x 16, Main
  • Eat In Kitchen: Eat-In Kitchen - Skylight, 9 ft+ Ceilings, Granite Counters, Dining Area, Islan, 15 x 12, Main
  • Dining Room: Dining Room - 9 ft+ Ceilings, Hardwood Floor, 14 x 14, Main
  • Office: Office - 9 ft+ Ceilings, Hardwood Floor, 10 x 8, Main
  • Game room: Yes
  • Game Room: Rec/Play Room - Laminate Floor, Lower
  • Rec Room: Laminate Floor, Lower
  • Theater/Media: Media Room - Laminate Floor, Lower
  • Laundry: Upper Level

Additional Information

  • Shared Amenities: Basketball Court, Club House, Exercise Room/Health Club, Playground/Tot Lot, Pool, Tennis Courts
  • Pool: Yes
  • Pool Description: Heated, In Ground Pool

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 2
  • Parking: Attached Garage, Paved, Off Street Parking, Driveway

Location

  • County: New Haven
  • Complex: Ridgewood at Middlebury
  • Driving Directions: GPS

School Information

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

Community

  • Association: Yes
  • Home Owners Assn.: 1
  • Assoc. Fees Include: Club House, Tennis, Grounds Maintenance, Trash Pickup, Snow Removal, Property Management, Pest Control, Pool Service, Insurance
  • Pets Allowed: Yes
  • Pet Restrictions: No restrictions

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Hot Air, Electric, Natural Gas
  • Heating Fuel: Electric, Natural Gas
  • Water Heater: Natural Gas, Domestic

Utilities

  • Sewer: Public Sewer Connected
  • Water: Public Water Connected

Structural Information

  • Architectural Style: Townhouse
  • Model: Portman
  • Construction Status: No/Resale
  • Exterior Const.: Vinyl Siding
  • Basement Desc.: Full, Heated, Fully Finished, Walk-out, Liveable Space, Full With Walk-Out
  • Attic: Yes
  • Square Feet: 2,680
  • Above Ground: 2,130 Sq. Ft.
  • Below Ground: 550 Sq. Ft.
  • Year Built: 2014

Lot Features

  • Zoning: PRD80
  • Lot Description: Lightly Wooded, Level Lot, On Cul-De-Sac

Green Features

  • Energy Features: Programmable Thermostat, Thermopane Windows

Financial Considerations

  • Association Fee: $515
  • Assoc Fee Freq.: Monthly
  • Assessment Amount: $308,600
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 2547199

Listed by Serhant Connecticut, LLC, WKND.R Team At SERHANT, Jay Irvine
Sold by William Raveis Real Estate, Tricia Lougal and William Raveis Real Estate, THE HAINSWORTH TEAM AT WILLIAM RAVEIS REAL ESTATE, Katie Westrin

Listing agent

— 27 Winding Trail #27 —

  • Jay Irvine

    Serhant Connecticut, LLC

Agent Contact: (203) 586-9459 Office Contact: (203) 489-7800

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 27 Winding Trail #27

School District:Regional School District 15
NameGradesDistance
Long Meadow Elementary School
65 North Benson Road, Middlebury, CT 06762
PK-51.3 mi
Memorial Middle School, Middlebury, CT
1 Memorial Drive, Middlebury, CT 06762
6-82.8 mi
Pomperaug Regional High School
234 Judd Road, Southbury, CT 06488
9-121.7 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 27 Winding Trail #27

Date
Details
Price
Change
Source
1/14/2026
Sold
$565,000
—
MLS
10/17/2025
Listed
$565,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Listed by Serhant Connecticut, LLC, WKND.R Team At SERHANT, Jay Irvine
Sold by William Raveis Real Estate, Tricia Lougal and William Raveis Real Estate, THE HAINSWORTH TEAM AT WILLIAM RAVEIS REAL ESTATE, Katie Westrin

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27 Winding Trail #27, Middlebury, CT 06762 (MLS# 24133988) is a Townhouse property that was sold at $565,000 on January 14, 2026. Want to learn more about 27 Winding Trail #27? Do you have questions about finding other Townhouse real estate for sale in Middlebury? You can browse all Middlebury real estate or contact a Coldwell Banker agent to request more information.