Lana Ogrodnik
Showcase Realty, Inc.
(475) 263-4970
59 Total Sales
1 in Winchester
$325,000 Price
Estimated Value: $453,627 - $484,000
Start your lakeside legacy at this rare waterfront cottage on Highland Lake. With stunning westerly views and a private dock, this is the perfect New England retreat for daily sunsets over the water. This intimate 512-square-foot home offers two bedrooms, a sunroom, Modern Eat-in Kitchen and a versatile loft space. with a newer roof, plumbing, electrical, and blown-in insulation, providing a low-maintenance opportunity to be ready QUICKLY for the next boating season! Highland Lake is a 445-acre reservoir in the Mountains, known for its recreational appeal. The lake is stocked annually, and it is designated a Trophy Trout and Bass Management Lake, making it an outstanding destination for anglers. Boating, swimming, and water skiing are among the many activities available, all within a community that values both recreation and tranquility. Don't miss the chance to own a piece of this serene, active, and beautiful lakeside community. Schedule a private tour today.
Last Agent to Sell the Property
Better Homes and Gardens Real Estate Executive Real Estate Brokerage Phone: (860) 916-6048 License #REB.0788717 Listed on: 08/29/2025
Co-Listed By
Better Homes and Gardens Real Estate Executive Real Estate Brokerage Phone: (860) 916-6048 License #RES.0807742
Lana Ogrodnik
Showcase Realty, Inc.
(475) 263-4970
59 Total Sales
1 in Winchester
$325,000 Price
Jim Treanor Jr
ERA Treanor Real Estate
(475) 244-9541
216 Total Sales
1 in Winchester
$420,000 Price
Chris Callahan
Berkshire Hathaway NE Prop.
(860) 406-5726
114 Total Sales
1 in Winchester
$288,557 Price
Susan Hotchkiss
Realty ONE Group Connect
(475) 241-7831
66 Total Sales
1 in Winchester
$185,000 Price
Amanda Nemense
Showcase Realty, Inc.
(475) 285-3197
114 Total Sales
2 in Winchester
$266K - $380K Price Range
Karen Mendes
Berkshire Hathaway NE Prop.
(959) 245-9021
219 Total Sales
1 in Winchester
$470,000 Price
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 |
|---|---|---|---|---|---|
| 10/28/2025 10/28/25 | Sold | $425,000 | +7.6% | $830 / Sq Ft | |
| 10/28/2025 10/28/25 | Pending | -- | -- | -- | |
| 08/29/2025 08/29/25 | For Sale | $394,900 | +43.6% | $771 / Sq Ft | |
| 06/19/2020 06/19/20 | Sold | $275,000 | -1.8% | $537 / Sq Ft | View Prior Sale |
| 06/19/2020 06/19/20 | Pending | -- | -- | -- | |
| 05/03/2020 05/03/20 | Price Changed | $279,900 | +1.8% | $547 / Sq Ft | |
| 04/13/2020 04/13/20 | Price Changed | $274,900 | -1.8% | $537 / Sq Ft | |
| 03/07/2020 03/07/20 | For Sale | $279,900 | +55.5% | $547 / Sq Ft | |
| 04/29/2019 04/29/19 | Sold | $180,000 | -27.7% | $352 / Sq Ft | View Prior Sale |
| 03/29/2019 03/29/19 | Pending | -- | -- | -- | |
| 09/04/2018 09/04/18 | For Sale | $249,000 | -- | $486 / 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 | $9,042 | $309,960 | $254,660 | $55,300 |
| 2024 | $8,443 | $309,960 | $254,660 | $55,300 |
| 2023 | $8,180 | $309,960 | $254,660 | $55,300 |
| 2022 | $6,203 | $184,940 | $149,380 | $35,560 |
| 2021 | $6,203 | $184,940 | $149,380 | $35,560 |
| 2020 | $6,031 | $179,830 | $149,380 | $30,450 |
| 2019 | $6,031 | $179,830 | $149,380 | $30,450 |
| 2018 | $6,031 | $179,830 | $149,380 | $30,450 |
| 2017 | $5,718 | $170,490 | $137,450 | $33,040 |
| 2016 | $5,718 | $170,490 | $137,450 | $33,040 |
| 2015 | $5,575 | $170,490 | $137,450 | $33,040 |
| 2014 | $5,440 | $170,490 | $137,450 | $33,040 |
Seller's Agent in 2025
Amy Rio
Executive Real Estate
(860) 916-6048
1,049 Total Sales
Seller Co-Listing Agent in 2025
Peter Caruso
Executive Real Estate
(772) 584-1097
5 Total Sales
Buyer's Agent in 2025
Deborah Cohen
Coldwell Banker Realty
(860) 461-5930
125 Total Sales
Seller's Agent in 2020
Edward Robertson
Coldwell Banker Premiere Realtor
(860) 299-6670
40 Total Sales
Buyer's Agent in 2020
John Cooney
Town & Country Real Estate
(860) 626-9534
1 Total Sale
Seller's Agent in 2019
David Sartirana
Northwest CT Realty
(860) 806-0225
342 Total Sales
Source: SmartMLS
MLS Number: 24121868
APN: WINC-000038-000105K-000181AZ
Ask me questions while you tour the home.