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$795,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 2 Full Baths
  • 1,373 Sq. Ft.
  • Updated 1 day ago
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Turn-key direct waterfront gem on Highland Lake! Perfectly positioned on the desirable east side of the lake, this beautifully maintained Cape offers abundant sunshine, gorgeous sunsets, & stunning water views. The updated kitchen features a breakfast bar, generous cabinet space, & opens to the dining room & inviting great room with hardwood floors & a gas fireplace. Enjoy lake views from the enclosed sunroom with sliders to the spacious deck, overlooking the level yard & private dock. The first floor offers a possible bedroom or office, full bath, and laundry. Upstairs are four additional bedrooms, including a beautiful lake facing primary bedroom with a large bay window, & breathtaking views. A full bath is conveniently located in the hall serving the upper level. Additional highlights include central air, whole-house generator, town water and sewer, newer roof, a full basement for storage & a putting green! Live like you are on vacation every day-swimming, boating, relaxing, and making memories with family and friends. This fabulous location offers quick access to Routes 8 & 44, with nearby attractions including Ski Sundown, Warner Theatre, wineries, breweries, hiking, and biking trails. Approx. 40 minutes to Hartford and Bradley International Airport, with convenient access toward New Haven and New York. Don't miss this rare opportunity to own your own slice of paradise on Highland Lake!

Full Property Details for 258 Perch Rock Trail

General

  • Price: $795,000
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24171657
  • Updated: 5/6/2026
  • Added to Site: 1 day(s) ago

Interior

  • Number of Rooms: 7
  • Interior Features: Cable - Available, Open Floor Plan
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Appliances: Oven/Range, Range Hood, Refrigerator, Dishwasher, Disposal, Washer, Dryer

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2
  • Full Bath: Tub w/Shower, Main

Bedrooms

  • Total Bedrooms: 4
  • Primary Bedroom: Primary Bedroom - Bay/Bow Window, Vaulted Ceiling, Wall/Wall Carpet, 16 x 9, Upper
  • Bedroom 1: Bedroom - Vaulted Ceiling, Wall/Wall Carpet, Upper
  • Bedroom 2: Bedroom - Vaulted Ceiling, Wall/Wall Carpet, Upper
  • Bedroom 3: Bedroom - Vaulted Ceiling, Wall/Wall Carpet, Upper

Other Rooms

  • Living Room: Living Room - Ceiling Fan, Combination Liv/Din Rm, Gas Log Fireplace, Sliders, Hardwood Floor, 13 x 12, Main
  • Eat In Kitchen: Eat-In Kitchen - Vaulted Ceiling, Breakfast Bar, Hardwood Floor, 17 x 13, Main
  • Dining Room: Dining Room - Combination Liv/Din Rm, Hardwood Floor, 12 x 10, Main
  • Office: Office, 12 x 10, Main
  • Laundry: Main Level

Exterior

  • Exterior Features: Porch-Enclosed, Porch, Deck, Gutters, Stone Wall

Location

  • County: Litchfield
  • Driving Directions: GPS Friendly

School Information

  • Elementary School: Per Board of Ed
  • High School: Per Board of Ed

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Hot Air, Oil
  • Heating Fuel: Oil
  • Water Heater: Electric, Tank Size Unknown

Utilities

  • Sewer: Public Sewer Connected
  • Water: Public Water Connected

Structural Information

  • Architectural Style: Cape Cod
  • Construction Status: No/Resale
  • Exterior Const.: Vinyl Siding
  • Basement Desc.: Partial, Partial With Walk-Out
  • Roof: Asphalt Shingle
  • Square Feet: 1,373
  • Above Ground: 1,373 Sq. Ft.
  • Year Built: 1922

Lot Features

  • Lot Size (Acres): 0.15
  • Zoning: HLD
  • Lot Description: Water View

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Water Front Desc.: Lake

Green Features

  • Energy Features: Generator

Financial Considerations

  • Assessment Amount: $434,210
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 928340

Listed by Berkshire Hathaway NE Prop., Nancy Reardon

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Listing agent

— 258 Perch Rock Trail —

  • Nancy Reardon

    Berkshire Hathaway NE Prop.

Agent Contact: (860) 836-7506 Office Contact: (860) 653-4507

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Price & Sales History for 258 Perch Rock Trail Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/06/2026
Listed
$795,000
20.45%
MLS
7/29/2021
Sold
$660,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 258 Perch Rock Trail

Year
Property Taxes
Change
Tax Assessment
Change
2025
$12,680
8%
$434,700
1%
2023
$11,689
3%
$429,100
—
2023
$11,324
26%
$429,100
60%
2022
$8,990
—
$268,030
—
2021
$8,955
—
$266,980
—
2020
$8,955
—
$266,980
—
2019
$8,955
—
$266,980
—
2018
$8,955
9%
$266,980
9%
2017
$8,182
—
$243,950
—
2016
$8,145
3%
$242,830
—
2015
$7,941
2%
$242,830
—
2014
$7,749
2%
$242,830
—
2011
$7,576
—
$242,830
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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*These costs are estimates, and the interest rates assume exceptional credit standing.

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NMLS#: 1598647

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Listed by Berkshire Hathaway NE Prop., Nancy Reardon

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258 Perch Rock Trail, Winchester, CT 06098 (MLS# 24171657) is a Single Family property with 4 bedrooms and 2 full bathrooms. 258 Perch Rock Trail is currently listed for $795,000 and was received on May 06, 2026. Want to learn more about 258 Perch Rock Trail? Do you have questions about finding other Single Family real estate for sale in Winsted? You can browse all Winsted real estate or contact a Coldwell Banker agent to request more information.

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