258 Perch Rock Trail Winchester, CT $ 795,000
258 Perch Rock Trail
$ 795,000
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258 Perch Rock Trail

Winchester, CT, 06098
$ 795,000
Bedrooms4 Baths2.0 Sq 1,373

Monthly Estimate*

$ 4,895

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Single Family Home for sale in Winchester, CT

for $795,000 with 4 bedrooms and 2 full baths. This 1,373 square foot home was built in 1922 on a lot size of 0.15.

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! Nestled in the foothills of the Berkshires in Northwest Connecticut, and set along the shores of Highland Lake, this property offers an exceptional four-season lifestyle in a truly scenic setting. One of Connecticut's premier full-recreation lakes, Highland Lake spans approximately 3 miles and over 440 acres, ideal for boating, kayaking, paddle boarding, swimming, and excellent fishing, including trout. In the winter months, the lake transforms into a classic New England destination for ice fishing, skating, snowmobiling, and cross-country skiing-bringing year-round enjoyment right outside your door. Located in the charming town of Winchester, you'll enjoy nearby dining, shops, and cafes in downtown Winsted, along with easy access to the renowned restaurants, boutique shopping, and timeless New England charm of Litchfield. Outdoor enthusiasts will appreciate close proximity to Ski Sundown and Butternut Ski Area for skiing, as well as local breweries including Little Red Barn Brewers and Norbrook Farm Brewery. Conveniently located with easy access to Routes 8 and 44, commuting is simple-approximately 40 minutes to Hartford and Bradley International Airport, with easy access to New Haven and New York City. Whether you're seeking a year-round residence or a weekend escape, this location offers the perfect balance of relaxation, recreation, and accessibility

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Single Family Contingent

Price

$ 795,000

Bedrooms

4

Full Bath

2

Property Type

Single Family

Taxes

$ 12,680

Style

Lot Size

0.15

Year Built

1922

Town/City

Winchester

MLS | Web ID

24171657

Features
General
Zoning HLD
Neighborhood N/A
County Litchfield
Tax Year July 2025-June 2026
Property Type Single Family For Sale
Status Under Contract
Acres 0.15
Directions GPS Friendly
High School Per Board of Ed
City Winchester
Elementary School Per Board of Ed
Sq Ft Total 1373
DOM 6
Year Built 1922
Style Cape Cod
Year Built Source Public Records
Energy Features Generator
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Interior
Cooling System Central Air
Total Rooms 7
Basement Description Partial Partial With Walk-Out
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Exterior
Water Source Public Water Connected
Lot Description Water View
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* Excluded Features
List By
Nancy Reardon

Listing Agent

Berkshire Hathaway Ne Prop.

Broker

nreardon@bhhsne.com

Email

Affordability Calculator

$5,952
Per Month
82%
18%
0%
Monthly Principal & Interest
$4,895
Monthly Property Taxes
$1,057
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
3092524 Elementary School
1232933 Middle School
Per Board of Ed High School High School
Pricing History
DatePricePrice ChangeDescription
5/7/2026$795,000 Listed Price

Map


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258 Perch Rock Trail, Winchester, CT, 06098 is a Single Family Home for sale at $795,000 with 1,373 sqft and a lot size of 0.15. 258 Perch Rock Trail has 4 bedrooms, 2.0 baths, and was built in 1922. The property's zip code is 06098 which is in Winchester, CT