Real Estate Agent in Connecticut and Western Massachusetts

27 Winding Trail
Middlebury, Connecticut

Condo/Co-Op For Sale

3

Bedrooms

2 (full) / 1 (half)

Bathrooms

2,680

Sq Ft

$ 565,000

Price

27 Winding Trail
Middlebury, Connecticut

Middlebury, Connecticut

Description:

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 Courtesy of Serhant Connecticut, LLC

Meet Our Team

Our team consists of dedicated real estate professionals passionate about helping our clients achieve their goals. Every client receives personalized attention, expert guidance, and unparalleled service. Meet our team:

Alison Malkin
Alison Malkin

Broker/Owner

860-214-8008

Email
Alison Malkin
Nicole Malkin James

Broker/Owner

843-614-7222

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Alison Malkin
Luis Torres

Associate Broker

860-383-5211

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Alison Malkin
Debra Pliego

Realtor®

860-919-7376

Email
Alison Malkin
Madison Wells

Realtor®

860-538-7567

Email
Alison Malkin
Lori Sierpinski

Realtor®

860-222-4692

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Alison Malkin
Jim Murkette

Realtor®

860-539-5009

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Alison Malkin
Leah Pliego

Realtor®

860-681-7373

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Alison Malkin
Shaissa Acosta

Realtor®

860-249-1641

Email

Appliances Included : Gas Cooktop, Oven/Range, Microwave, Dishwasher, Disposal
Association Amenities : Basketball Court, Club House, Exercise Room/Health Club, Playground/Tot Lot, Pool, Tennis Courts
Association Fee Includes : Club House, Tennis, Grounds Maintenance, Trash Pickup, Snow Removal, Property Management, Pest Control, Pool Service, Insurance
Attic : Crawl Space, Access Via Hatch
Basement : Full, Heated, Fully Finished, Walk-out, Liveable Space, Full With Walk-Out
Full Baths : 2
Half Baths : 1
Baths Total : 3
Beds Total : 3
City : Middlebury
Complex : Ridgewood at Middlebury
Cooling : Central Air
County : New Haven
Elementary School : Per Board of Ed
Fireplaces : 1
Garage Parking : Attached Garage, Paved, Off Street Parking, Driveway
Garage Slots : 2
Description : Lightly Wooded, Level Lot, On Cul-De-Sac
Amenities : Golf Course, Health Club, Lake, Medical Facilities, Park, Playground/Tot Lot, Private School(s)
Neighborhood : N/A
Parcel : 2547199
Total Parking Spaces : 2
Pets : No restrictions
Pets Allowed : Yes
Pool Description : Heated, In Ground Pool
Postal Code : 06762
Sewage System : Public Sewer Connected
Total SqFt : 2680
Tax Year : July 2025-June 2026
Total Rooms : 9
Watersource : Public Water Connected
weeb : RPR, IDX Sites, Realtor.com

Phone

860-384-7624

Address

20 Hopmeadow St, Unit 821, Weatogue, CT 06089


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