Lisa Bowman
Coldwell Banker Realty
(475) 325-5582
70 Total Sales
1 in Middlebury
$360,000 Price
3 Winding Trail Middlebury, CT 06762
Middlebury Area
3
Beds
2.5
Baths
3,179
Sq Ft
2007
Built
Highlights
- In Ground Pool
- Attic
- Tankless Water Heater
- Finished Attic
- Cul-De-Sac
- Central Air
About This Home
As of July 2026Welcome 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
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Townhouse Details
Home Type
- Townhome
Est. Annual Taxes
- $8,471
Year Built
- Built in 2007
HOA Fees
- $495 Monthly HOA Fees
Parking
- 1 Car Garage
Home Design
- Frame Construction
- Vinyl Siding
Kitchen
- Gas Range
- Dishwasher
Bedrooms and Bathrooms
- 3 Bedrooms
Attic
- Walkup Attic
- Finished Attic
Basement
- Walk-Out Basement
- Basement Fills Entire Space Under The House
Utilities
- Central Air
- Heating System Uses Natural Gas
- Tankless Water Heater
Additional Features
- In Ground Pool
- Cul-De-Sac
Listing and Financial Details
- Assessor Parcel Number 2547175
Community Details
Overview
- Association fees include club house, tennis, grounds maintenance, trash pickup, snow removal, pest control, pool service, road maintenance
- 141 Units
Pet Policy
- Pets Allowed
Ownership History
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
Name
Owned For
Owner Type
Purchase Details
Listed on
Sep 6, 2019
Closed on
Oct 30, 2019
Sold by
Bought by
Seller's Agent
Jay Irvine
Serhant Connecticut, LLC
Buyer's Agent
Pat Blanko
William Raveis Real Estate
List Price
$339,900
Sold Price
$335,000
Premium/Discount to List
-$4,900
-1.44%
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Avg. Annual Appreciation
7.93%
Original Mortgage
$268,000
Outstanding Balance
$231,639
Interest Rate
3.6%
Mortgage Type
Purchase Money Mortgage
Estimated Equity
$329,505
Home Values in the Area
Average Home Value in this Area
Agents Specializing in Middlebury, CT
-
Lisa Bowman
-
Susan Hanson
Susan Hanson
William Raveis Real Estate
(475) 258-7012
100 Total Sales
1 in Middlebury
$515,000 Price
-
Pam Famiglietti
Pam Famiglietti
William Raveis Real Estate
(475) 219-6733
162 Total Sales
10 in Middlebury
$85K - $900K Price Range
-
Susan Cassidy
Susan Cassidy
Coldwell Banker Realty
(475) 476-2101
77 Total Sales
1 in Middlebury
$545,000 Price
-
Chris LaCava
Chris LaCava
Coldwell Banker Realty
(475) 323-6757
148 Total Sales
2 in Middlebury
$550K - $1.4M Price Range
-
Jane Spino
Jane Spino
Showcase Realty, Inc.
(860) 590-9746
69 Total Sales
2 in Middlebury
$295K - $487K Price Range
Purchase History
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 | -- |
Source: Public Records
Mortgage History
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 |
Source: Public Records
Property History
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 |
Source: SmartMLS
Tax History
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 |
Source: Public Records
Agents Affiliated with this Home
-
Mayra Perez
Seller's Agent in 2026
Mayra Perez
Showcase Realty, Inc.
(203) 558-5866
55 Total Sales
-
Ray Getman
Buyer's Agent in 2026
Ray Getman
William Raveis Real Estate
(203) 947-1400
63 Total Sales
-
Jay Irvine
Seller's Agent in 2019
Jay Irvine
Serhant Connecticut, LLC
(203) 586-9459
80 Total Sales
-
Pat Blanko
Buyer's Agent in 2019
Pat Blanko
William Raveis Real Estate
(203) 206-9194
136 Total Sales
Map
Source: SmartMLS
MLS Number: 24177196
APN: MIDD-000706-000000-000073-000016
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.
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