Amy Rio
Better Homes and Gardens Real Estate Executive Real Estate
(860) 321-8567
1,030 Total Sales
5 in Winchester
$60K - $425K Price Range
Welcome to "WatersEdge" a Seasonal Cottage perched on a landscaped hillside overlooking Third Bay of beautiful Highland Lake. Views Views Views! Highland is a fully recreational lake. On the main floor of the cottage you will find one bedroom, a bath with shower, a spacious family room with a stone fireplace, and an efficient kitchen with storage. The lower walk-out level can be accessed by the spiral staircase, and includes a 1/2 bath with potential for additional sleeping and a closet. Off the lower level is a patio overlooking the private beach and dock. There is also an outdoor shower! The expansive deck off the main level, truly gives one a treehouse vibe, with the stunning vista of Third Bay. It is a wonderful, outdoor space for relaxing or entertaining. From the deck one can wind their way down the stone stairway lined with rhododendrons, and when in blossom a tranquil, private oasis is yours to enjoy. Unlike many lakeside homes this three season cottage has privacy areas both shaded and sunny. The cottage is connected to a town sewer system and has a shared private well. Highland Lake has two public beaches, a privately owned marina and a public boat launch. Over the years downtown known as Winsted, has been experiencing a renaissance, with new restaurants, a brewery, grocery stores, and unique shops along Main Street. Don't miss this quintessential Lakefront retreat! A parcel of .72 acres across the road, known as #735 is included with the sale.
Last Agent to Sell the Property
Lakefront Living Realty, LLC Brokerage Phone: (860) 209-7620 License #RES.0798233 Listed on: 05/16/2026
Last Buyer's Agent
Lakefront Living Realty, LLC Brokerage Phone: (860) 209-7620 License #RES.0798233 Listed on: 05/16/2026
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
Amy Rio
Better Homes and Gardens Real Estate Executive Real Estate
(860) 321-8567
1,030 Total Sales
5 in Winchester
$60K - $425K Price Range
Mike Albert
RE/MAX RISE
(860) 845-0960
242 Total Sales
1 in Winchester
$179,900 Price
John Daikus
eXp Realty
(860) 590-9556
57 Total Sales
1 in Winchester
$240,000 Price
Justin Guerrera
Regency Real Estate, LLC
(475) 285-4179
41 Total Sales
1 in Winchester
$180,000 Price
Rob Rosa
Berkshire Hathaway NE Prop.
(860) 560-1786
286 Total Sales
1 in Winchester
$255,000 Price
David Sartirana
Northwest CT Realty
(959) 251-2063
341 Total Sales
158 in Winchester
$118 - $960K 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 |
|---|---|---|---|
| Deed | $110,000 | -- |
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 | Event | Price | List to Sale | Price per Sq Ft | Prior Sale |
|---|---|---|---|---|---|
| 07/21/2026 07/21/26 | Sold | $525,000 | -3.5% | $401 / Sq Ft | |
| 07/06/2026 07/06/26 | Pending | -- | -- | -- | |
| 05/16/2026 05/16/26 | For Sale | $544,000 | +76.6% | $416 / Sq Ft | |
| 06/29/2017 06/29/17 | Sold | $308,000 | -3.7% | $383 / Sq Ft | View Prior Sale |
| 06/02/2017 06/02/17 | Pending | -- | -- | -- | |
| 05/04/2017 05/04/17 | For Sale | $319,900 | -- | $398 / 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 | $10,704 | $366,940 | $267,750 | $99,190 |
| 2024 | $9,995 | $366,940 | $267,750 | $99,190 |
| 2023 | $9,684 | $366,940 | $267,750 | $99,190 |
| 2022 | $7,229 | $215,530 | $157,080 | $58,450 |
| 2021 | $7,229 | $215,530 | $157,080 | $58,450 |
| 2020 | $7,229 | $215,530 | $157,080 | $58,450 |
| 2019 | $7,229 | $215,530 | $157,080 | $58,450 |
| 2018 | $7,229 | $215,530 | $157,080 | $58,450 |
| 2017 | $6,370 | $189,910 | $139,370 | $50,540 |
| 2016 | $6,163 | $183,750 | $139,370 | $44,380 |
| 2015 | $6,009 | $183,750 | $139,370 | $44,380 |
| 2014 | $5,863 | $183,750 | $139,370 | $44,380 |
Seller's Agent in 2026
Ed Richman
Lakefront Living Realty, LLC
(860) 209-7620
18 Total Sales
Seller's Agent in 2017
Kim Trumbull
William Raveis Real Estate
(860) 309-6542
38 Total Sales
Source: SmartMLS
MLS Number: 24098872
APN: WINC-000038-000112-000018
Ask me questions while you tour the home.