29 Winding Trail #29, Middlebury, CT 06762 - Photo 1

1/1

$520,000

Sold
Closed
Townhouse
3 Beds
2 Full Baths
1 Partial Bath
2,130 Sq. Ft.
2 Car Garage

1/1

Property Description

Beautiful 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!

Full Property Details

Full Property Details for 29 Winding Trail #29

General

Sold For: $520,000
HOA FEE: $515/month
Taxes: (July 2025-June 2026)
Status: Closed
Type: Townhouse
Source: SMARTMLS
MLS ID: 24085206
Added to Site: 290 day(s) ago

Interior

Number of Rooms: 6
Interior Features: Cable - Pre-wired, Open Floor Plan
Fireplace: Yes
Number of Fireplaces: 1
Appliances: Gas Cooktop, Wall Oven, Microwave, Refrigerator, Dishwasher, Disposal, Washer, Electric Dryer

Rooms

Bathrooms

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

Bedrooms

Total Bedrooms: 3
Primary Suite: 9 ft+ Ceilings, Vaulted Ceiling, Bedroom Suite, Full, 17 x 16.8, Upper
Bedroom 1: Bedroom - 9 ft+ Ceilings, Vaulted Ceiling, Walk-In Closet, Wall/Wall Carpet, 12.1 x 11.7, Upper
Bedroom 2: Bedroom - 9 ft+ Ceilings, Built-Ins, Wall/Wall Carpet, 13.2 x 11, Upper

Other Rooms

Living Room: Living Room - 9 ft+ Ceilings, Gas Log Fireplace, L-Shaped, Hardwood Floor, 17 x 15.7, Main
Eat In Kitchen: Eat-In Kitchen - Skylight, 9 ft+ Ceilings, Breakfast Bar, Granite Counters, Gas, Main
Dining Room: Dining Room - 9 ft+ Ceilings, Beams, Combination Liv/Din Rm, Gas Log Fireplace, 13 x 11, Main
Laundry: Main Level

Additional Information

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

Parking

Garage: Yes
Attached garage: Yes
Garage Spaces: 2
Total Spaces: 4
Parking: Attached Garage, Under House Garage, Paved

Location

County: New Haven
Complex: Ridgewood at Middlebury
Driving Directions: GPS- Ridgewood drive to Winding trail

School Information

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

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: Pets allowed.

Heating & Cooling

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

Utilities

Sewer: Public Sewer Connected
Water: Public Water Connected

Structural Information

Architectural Style: Townhouse
Model: Portman W/ Bump out
Construction Status: No/Resale
Exterior Const.: Vinyl Siding
Basement Desc.: Full, Unfinished, Walk-out, Liveable Space, Concrete Floor, Full With Walk-Out
Attic: Yes
Square Feet: 2,130
Above Ground: 2,130 Sq. Ft.
Year Built: 2015

Lot Features

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

Green Features

Energy Features: Fireplace Insert, Programmable Thermostat, Thermopane Windows

Financial Considerations

Association Fee: $515
Assoc Fee Freq.: Monthly
Assessment Amount: $311,900
Tax Year: July 2025-June 2026

Disclosures and Reports

Property ID: 2547200

Listed by Serhant Connecticut, LLC, WKND.R Team At SERHANT, Jay Irvine
Sold by KW Legacy Partners, Miale Team at Keller Williams Legacy Partners, Tori Withee

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Listing agent

— 29 Winding Trail #29 —

Jay Irvine

Serhant Connecticut, LLC

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Schools

Schools serving 29 Winding Trail #29

School District:Regional School District 15

Name	Grades	Distance
Long Meadow Elementary School 65 North Benson Road, Middlebury, CT 06762	PK-5	1.3 mi
Memorial Middle School, Middlebury, CT 1 Memorial Drive, Middlebury, CT 06762	6-8	2.8 mi
Pomperaug Regional High School 234 Judd Road, Southbury, CT 06488	9-12	1.7 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 29 Winding Trail #29

Date

Details

Price

Change

Source

8/08/2025

Sold

$520,000

-1.89%

MLS

7/16/2025

Price Reduced

$530,000

-3.62%

MLS

5/15/2025

Price Reduced

$549,900

-2.67%

MLS

4/02/2025

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.

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Updated 2 days ago

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Beds
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Total Baths
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Beds
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Total Baths
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Beds
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Beds
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Total Baths
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29 Winding Trail #29, Middlebury, CT 06762 (MLS# 24085206) is a Townhouse property that was sold at $520,000 on August 08, 2025. Want to learn more about 29 Winding Trail #29? 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.

29 Winding Trail #29 Middlebury, CT 06762