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!
Sold for $565,000
$565,000
27 Winding Trail #27, Middlebury, CT 06762
3beds
2,680sqft
Condominium, Townhouse
Built in 2014
-- sqft lot
$574,900 Zestimate®
$211/sqft
$3,781 Estimated rent
Home value
$574,900
$512,000 - $644,000
$3,781/mo
Zestimate® history
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$4,545/mo
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List your homeWhat's special
Soaking tubWooded backdropPrivate cul-de-sacRich wood mantleMarble countertopsUpgraded skylightSeparate shower
Zillow last checked:
Listing updated:
Listed by:
WKND.R Team At SERHANT,
Jay Irvine (203)586-9459,
Serhant Connecticut, LLC 203-489-7800
Bought with:
Tricia Lougal, RES.0832785
William Raveis Real Estate
Co-Buyer Agent: Katie Westrin
William Raveis Real Estate
Source: Smart MLS,MLS#: 24133988
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 3
- Full bathrooms: 2
- 1/2 bathrooms: 1
Primary bedroom
- Features: Vaulted Ceiling(s), Bedroom Suite, Full Bath, Walk-In Closet(s), Hardwood Floor
- Level: Upper
- Area: 289 Square Feet
- Dimensions: 17 x 17
Bedroom
- Features: High Ceilings, Hardwood Floor
- Level: Upper
- Area: 169 Square Feet
- Dimensions: 13 x 13
Bedroom
- Features: Vaulted Ceiling(s), Hardwood Floor
- Level: Upper
- Area: 169 Square Feet
- Dimensions: 13 x 13
Dining room
- Features: High Ceilings, Hardwood Floor
- Level: Main
- Area: 196 Square Feet
- Dimensions: 14 x 14
Kitchen
- Features: Skylight, High Ceilings, Granite Counters, Dining Area, Kitchen Island, Hardwood Floor
- Level: Main
- Area: 180 Square Feet
- Dimensions: 12 x 15
Living room
- Features: High Ceilings, Combination Liv/Din Rm, Gas Log Fireplace, Hardwood Floor
- Level: Main
- Area: 272 Square Feet
- Dimensions: 16 x 17
Media room
- Features: Laminate Floor
- Level: Lower
Office
- Features: High Ceilings, Hardwood Floor
- Level: Main
- Area: 80 Square Feet
- Dimensions: 8 x 10
Rec play room
- Features: Laminate Floor
- Level: Lower
Heating
- Forced Air, Electric, Natural Gas
Cooling
- Central Air
Appliances
- Included: Gas Cooktop, Oven/Range, Microwave, Dishwasher, Disposal, Gas Water Heater, Water Heater
- Laundry: Upper Level
Features
- Wired for Data
- Windows: Thermopane Windows
- Basement: Full,Heated,Finished,Walk-Out Access,Liveable Space
- Attic: Crawl Space,Access Via Hatch
- Number of fireplaces: 1
Interior area
- Total structure area: 2,680
- Total interior livable area: 2,680 sqft
- Finished area above ground: 2,130
- Finished area below ground: 550
Property
Parking
- Total spaces: 2
- Parking features: Attached, Paved, Off Street, Driveway
- Attached garage spaces: 2
- Has uncovered spaces: Yes
Features
- Stories: 2
- Has private pool: Yes
- Pool features: Heated, In Ground
Lot
- Features: Few Trees, Level, Cul-De-Sac
Details
- Parcel number: 2547199
- Zoning: PRD80
Construction
Type & style
- Home type: Condo
- Architectural style: Townhouse
- Property subtype: Condominium, Townhouse
Materials
- Vinyl Siding
Condition
- New construction: No
- Year built: 2014
Details
- Builder model: Portman
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Green energy
- Energy efficient items: Thermostat, Windows
Community & neighborhood
Security
- Security features: Security System
Community
- Community features: Golf, Health Club, Lake, Medical Facilities, Park, Playground, Private School(s)
Location
- Region: Middlebury
HOA & financial
HOA
- Has HOA: Yes
- HOA fee: $515 monthly
- Amenities included: Basketball Court, Clubhouse, Exercise Room/Health Club, Playground, Pool, Tennis Court(s), Management
- Services included: Maintenance Grounds, Trash, Snow Removal, Pest Control, Pool Service, Insurance
Price history
| Date | Event | Price |
|---|---|---|
| 1/17/2026 | Pending sale | $565,000$211/sqft |
Source:  Smart MLS #24133988 Report a problem | ||
| 1/14/2026 | Sold | $565,000$211/sqft |
Source: Smart MLS #24133988 Report a problem | ||
| 10/17/2025 | Listed for sale | $565,000+18.9%$211/sqft |
Source: Smart MLS #24133988 Report a problem | ||
| 6/27/2022 | Sold | $475,000+2.2%$177/sqft |
Source: Smart MLS #170473725 Report a problem | ||
| 6/11/2022 | Contingent | $465,000$174/sqft |
Source: Smart MLS #170473725 Report a problem | ||
| 3/14/2022 | Listed for sale | $465,000+30.6%$174/sqft |
Source: Smart MLS #170473725 Report a problem | ||
| 3/15/2019 | Sold | $356,000$133/sqft |
Source: Smart MLS #170143943 Report a problem | ||
Public tax history
Tax history is unavailable.
Neighborhood: 06762
Nearby schools
GreatSchools rating
- 5/10Long Meadow Elementary SchoolGrades: PK-5Distance: 1.3 mi
- 8/10Memorial Middle SchoolGrades: 6-8Distance: 2.9 mi
- 8/10Pomperaug Regional High SchoolGrades: 9-12Distance: 1.7 mi
Schools provided by the listing agent
- High: Pomperaug
Source: Smart MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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- Connecticut
- New Haven County
- Middlebury
- 06762
- 27 Winding Trail Unit 27
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