Mike Albert
RE/MAX RISE
(860) 845-0960
242 Total Sales
1 in Middlebury
$479,000 Price
Welcome to 3 Winding Trail, nestled on a quiet cul-de-sac in the highly desirable Ridgewood community of Middlebury. This beautifully maintained 3-bedroom, 2.5-bath condo offers the perfect blend of elegance, comfort, and low-maintenance living across 4 finished levels, including a sun-filled walk-out lower level. From the moment you step inside, you'll appreciate the gleaming hardwood floors, natural light throughout, spacious layout, and updated kitchen featuring granite countertops, stainless steel appliances, and ample space for entertaining. The spacious primary suite offers a peaceful retreat, while the additional finished spaces provide incredible flexibility for a family room, home office, gym, playroom, or guest area. Step outside to your private deck and patio surrounded by peaceful wooded views - perfect for relaxing or entertaining. Enjoy resort-style amenities including a pool, tennis courts, clubhouse, and fitness center, all within minutes of shopping, dining, and major commuter routes. Move-in ready and located in one of Middlebury's most sought-after communities, this is a rare opportunity you won't want to miss.
Last Agent to Sell the Property
Showcase Realty, Inc. Brokerage Phone: (203) 558-5866 License #RES.0809820 Listed on: 05/23/2026
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
Mike Albert
RE/MAX RISE
(860) 845-0960
242 Total Sales
1 in Middlebury
$479,000 Price
John Daikus
eXp Realty
(860) 590-9556
58 Total Sales
2 in Middlebury
$435K - $515K Price Range
Alexa Skalandunas
William Raveis Real Estate
(475) 348-7664
25 Total Sales
1 in Middlebury
$800,000 Price
Fredda Takacs
Higgins Group Real Estate
(475) 269-6854
134 Total Sales
1 in Middlebury
$380,000 Price
Rebecca Zandvliet
Coldwell Banker Realty 2000
(959) 800-0592
155 Total Sales
2 in Middlebury
$63K - $1M Price Range
Dawn Cabral
West View Properties, LLC
(475) 244-7412
94 Total Sales
3 in Middlebury
$445K - $590K Price Range
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Warranty Deed | $335,000 | -- |
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Status | Loan Amount | Loan Type |
|---|---|---|---|
| Open | $268,000 | Purchase Money Mortgage |
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Event | Price | List to Sale | Price per Sq Ft | Prior Sale |
|---|---|---|---|---|---|
| 07/16/2026 07/16/26 | Sold | $559,900 | 0.0% | $176 / Sq Ft | |
| 07/10/2026 07/10/26 | Pending | -- | -- | -- | |
| 05/23/2026 05/23/26 | For Sale | $559,900 | +67.1% | $176 / Sq Ft | |
| 11/05/2019 11/05/19 | Sold | $335,000 | -1.4% | $113 / Sq Ft | View Prior Sale |
| 09/13/2019 09/13/19 | Pending | -- | -- | -- | |
| 09/06/2019 09/06/19 | For Sale | $339,900 | -- | $115 / Sq Ft |
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $8,042 | $247,300 | $0 | $247,300 |
| 2024 | $8,062 | $247,300 | $0 | $247,300 |
| 2023 | $7,978 | $247,300 | $0 | $247,300 |
| 2022 | $7,731 | $247,300 | $0 | $247,300 |
| 2021 | $7,791 | $223,700 | $0 | $223,700 |
| 2020 | $7,852 | $223,700 | $0 | $223,700 |
| 2019 | $7,472 | $223,700 | $0 | $223,700 |
| 2018 | $7,272 | $223,700 | $0 | $223,700 |
| 2017 | $7,044 | $223,700 | $0 | $223,700 |
| 2016 | $6,956 | $224,300 | $0 | $224,300 |
| 2015 | $6,756 | $224,300 | $0 | $224,300 |
| 2014 | $6,581 | $224,300 | $0 | $224,300 |
Seller's Agent in 2026
Mayra Perez
Showcase Realty, Inc.
(203) 558-5866
59 Total Sales
Buyer's Agent in 2026
Ray Getman
William Raveis Real Estate
(203) 947-1400
62 Total Sales
Seller's Agent in 2019
Jay Irvine
Serhant Connecticut, LLC
(203) 586-9459
84 Total Sales
Buyer's Agent in 2019
Pat Blanko
William Raveis Real Estate
(203) 206-9194
126 Total Sales
Source: SmartMLS
MLS Number: 24177196
APN: MIDD-000706-000000-000073-000016
Ask me questions while you tour the home.