About 27 Winding Trail 27
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!
Features of 27 Winding Trail 27
| MLS® # | 24133988 |
|---|---|
| Price | $565,000 |
| Bedrooms | 3 |
| Bathrooms | 3.00 |
| Full Baths | 2 |
| Half Baths | 1 |
| Square Footage | 2,680 |
| Type | Condo/Co-Op For Sale |
| Sub-Type | Condominium |
| Style | Townhouse |
| Status | Active |
Community Information
| Address | 27 Winding Trail 27 |
|---|---|
| Area | N/A |
| City | Middlebury |
| County | New Haven |
| State | Connecticut |
| Zip Code | 06762 |
Amenities
| Amenities | Basketball Court, Club House, Exercise Room/Health Club, Playground/Tot Lot, Pool, Tennis Courts |
|---|---|
| Features | Programmable Thermostat, Thermopane Windows |
| Parking Spaces | 2 |
| Parking | Attached Garage, Driveway, Paved, Off Street Parking |
| # of Garages | 2 |
| Is Waterfront | No |
| Waterfront | Not Applicable |
| Has Pool | Yes |
| Pool | Heated, In Ground Pool |
Interior
| Interior Features | Cable - Pre-wired, Security System |
|---|---|
| Appliances | Gas Cooktop, Oven/Range, Microwave, Dishwasher, Disposal |
| Heating | Hot Air, Natural Gas |
| Cooling | Central Air |
| Fireplace | Yes |
| # of Fireplaces | 1 |
| # of Stories | 2 |
| Has Basement | Yes |
| Basement | Full, Heated, Fully Finished, Walk-out, Liveable Space, Full With Walk-Out |
Exterior
| Exterior | Vinyl Siding |
|---|---|
| Lot Description | Lightly Wooded, Level Lot, On Cul-De-Sac |
School Information
| Elementary | Per Board of Ed |
|---|---|
| High | Pomperaug |
Additional Information
| Date Listed | October 17th, 2025 |
|---|---|
| Zoning | PRD80 |
| RE / Bank Owned | No |
| HOA Fees | 515 |
| HOA Fees Freq. | Monthly |
Listing Details
| Office | Serhant Connecticut, LLC |
|---|