New Listing - 04/02/2025

$565,000 ($265.26 per sqft)

Est. Mortgage $2,746/mo *

Quick Pre-Approval

Brochure

Call Text Schedule Tour Request More Information

29 Winding Trail, #29, Middlebury, CT, 06762

29 Winding Trail, #29, Middlebury, CT, 06762
View larger map Directions

6 rooms

3 beds

2 Full / 1 Half baths

2015

Townhouse

2,130 sqft

Beautiful Portman Condo in Sought-After Ridgewood Community. Stunning 3-bed, 2.5-bath condo 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 must-see property! Can't build for this price!

Status:

Active

Type:

Condo

Laundry Remarks:

Main Level

Units:

4

Zoning:

PRD80

Complex:

Ridgewood at Middlebury

Garage:

2-car Attached Garage, Under House Garage, Paved

Heating:

Hot Air

Cooling:

Central Air

Energy Features:

Fireplace Insert, Programmable Thermostat, Thermopane Windows

Basement:

Full, Unfinished, Walk-out, Liveable Space, Concrete Floor, Full With Walk-Out

Levels:

3

Parking:

4-car

Common Charge:

$515 Monthly

Est. Taxes:

$10,168

Assessment

$311,900

HOA Fee

$515

Lot Description:

Secluded,Lightly Wooded,On Cul-De-Sac

Amenities:

Basketball Court, Club House, Exercise Room/Health Club, Guest Parking, Health Club, Playground/Tot Lot, Pool, Tennis Courts

Elementary School:

Per Board of Ed

High School:

Per Board of Ed

Days on Market:

2

Pet Allowed:

Yes

Pet Policy:

Pets allowed.

Appliances:

Gas Cooktop, Wall Oven, Microwave, Refrigerator, Dishwasher, Disposal, Washer, Electric Dryer

Pool:

Heated, Pool House, In Ground Pool

MLS #:

24085206

Community Info

School Info

Walk Score

Mass Transit

Yelp

Similar Properties

$591,251

3 beds

2.5 baths

2,923 sqft

North Benson Road, #35, Middlebury, CT, 06762

$589,500

3 beds

2.5 baths

2,600 sqft

7 Highridge Road, #7, Middlebury, CT, 06762

$545,400

3 beds

2.5 baths

2,206 sqft

North Benson Road, #64, Middlebury, CT, 06762

Price Reduced!

$574,888

2 beds

2.5 baths

2,145 sqft

80 Seaview Terrace, #29, Guilford, CT, 06437

$541,566

3 beds

2.5 baths

2,206 sqft

North Benson Road, #41, Middlebury, CT, 06762

$509,300

3 beds

2.5 baths

1,950 sqft

North Benson Road, #40, Middlebury, CT, 06762

$549,000

2 beds

2.5 baths

1,879 sqft

49 Wilshire Road, #49, Madison, (Hammonasset), CT, 06443

$573,570

2 beds

2.5 baths

1,850 sqft

116 Shea Circle, #116, Cheshire, CT, 06410

$546,936

3 beds

2.5 baths

2,252 sqft

North Benson Road, #43, Middlebury, CT, 06762

Price Reduced!

$529,000

2 beds

2.5 baths

2,030 sqft

1003 Saint Andrews Drive, #1003, Oxford, CT, 06478

$619,000

2 beds

2 baths

1,600 sqft

1 Pine Ridge, #24, Middlebury, CT, 06762

Price Reduced!

$585,000

4 beds

2.5 baths

2,426 sqft

22 Newbury Court, #22, North Haven, (Montowese), CT, 06473

$511,000

3 beds

2.5 baths

1,950 sqft

North Benson Road, #38, Middlebury, CT, 06762

Price Reduced!

$539,900

2 beds

2.5 baths

1,877 sqft

704 Holly Court, #704, Oxford, (Meadowbrook), CT, 06478

$559,900

2 beds

2 baths

1,560 sqft

110 Sandpiper Circle, Milford, (Merwin's Beach), CT, 06460

$509,900

3 beds

2.5 baths

1,950 sqft

North Benson Road, #37, Middlebury, CT, 06762

New or Coming Soon Properties

New Listing!

$615,000

2 beds

2 baths

1,200 sqft

195 Southport Woods Drive, #195, Fairfield, (Southport), CT, 06890

New Listing!

$595,000

2 beds

2 baths

2,257 sqft

663 Championship Drive, #663, Oxford, CT, 06478

New Listing!

$550,000

3 beds

2.5 baths

2,680 sqft

36 Lavoie Drive, City Not Found, CT, 05452

New Listing!

$575,000

3 beds

2.5 baths

1,882 sqft

180 Ridgewood Drive, #219, Middlebury, CT, 06762

New Listing!

$569,900

2 beds

2.5 baths

1,481 sqft

142 East Avenue, #A303, Norwalk, (East Norwalk), CT, 06851

New Listing!

$539,900

2 beds

2.5 baths

2,092 sqft

130 Meadow Brook Road, #130, Oxford, (Meadowbrook), CT, 06478

New Listing!

$569,900

2 beds

2.5 baths

2,593 sqft

112 Periwinkle Drive, #112, Middlebury, CT, 06762

Price Reduced!

$579,000

3 beds

3.5 baths

2,893 sqft

36 Lamoille Street, City Not Found, CT, 05452

New Listing!

$535,000

3 beds

2.5 baths

2,221 sqft

52 Woodcrest Lane, #52, Danbury , (Shelter Rock), CT, 06810

Price Reduced!

$534,000

2 beds

2 baths

1,510 sqft

696 Championship Drive, #696, Oxford, CT, 06478

New Listing!

$570,000

3 beds

3 baths

1,600 sqft

2 Mansfield Grove Road, #APT 161, East Haven, CT, 06512

New Listing!

$524,900

3 beds

2.5 baths

2,265 sqft

27 Olde Village Circle, #27, Wallingford, CT, 06492

New Listing!

$559,900

2 beds

2.5 baths

1,231 sqft

76 Fawn Ridge Lane, #76, Norwalk, (Cranbury), CT, 06851

New Listing!

$577,900

3 beds

2 baths

1,477 sqft

1 Lantern Court, #1, Clinton, CT, 06413

New Listing!

$525,000

5 beds

2 baths

2,405 sqft

138 Boston Post Road, #1, East Lyme, (Flanders Village), CT, 06333

New Listing!

$559,900

2 beds

2.5 baths

1,316 sqft

5 Harbour Village, #B, Branford, (Branford Point), CT, 06405

Copyright ©2025 SmartMLS, Inc.
Listing courtesy of Jay Irvine, Serhant Connecticut, LLC Email: realtor.j.irvine@gmail.com