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63 Properties Available
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$349,000
Single Family Home
150 Mathew Road, Winchester, CT 06098
Highland Lake, 3 Bedroom, 2 Bath, well maintained home. Lake views, newer appliances, hardwood floors, move-in ready, la...
Listed by Josh Dionne of Commercial Services Realty
$299,900
Single Family Home
155 Mathew Road, Winchester, CT 06098
Situated on a private road with views of Highland Lake, this beautifully updated home offers a perfect blend of modern c...
Listed by Austin Brochu of Sullivan Real Estate Inc
$260,000
Single Family Home
120 Torrington Road, Winchester, CT 06098
This spacious 5-bedroom, 2-bath Colonial offers incredible flexibility and room to grow. The first floor features a larg...
Listed by David Bolduc of Bolduc Realty Group
$1,195
Multi-Family
174 Main Street #C, Winchester, CT 06098
One bedroom apartment on the first floor. Large kitchen with pantry and a recently remodeled bath. Pets considered. Firs...
Listed by Amanda Balaski of Northwest CT Realty
$979,000
Single Family Home
355 West Lake Street, Winchester, CT 06098
Sweeping Views, Exceptional Craftsmanship, and Lake Life at Its Finest.Set on a rare half-acre double lot across from Hi...
Listed by David Sartirana of Northwest CT Realty
$1,295
Multi-Family
88 Spencer Street #2, Winchester, CT 06098
Two bedroom, 1st flr apartment close to town. Private fronch porch. A washer-dryer can be provided for an extra $50 per ...
Listed by Amanda Balaski of Northwest CT Realty
$995,000
Single Family Home
469 Platt Hill Road, Winchester, CT 06098
HOME-LAND -BARN. A TRUE NEW ENGLAND CLASSIC PROPERTY IN A POST CARD SETTING! For the Discerning Customer, whether You're...
Listed by Marshall Cohen of Cohen Agency
$158,000
Single Family Home
9 John Street, Winchester, CT 06098
Perfect property for a tiny home enthusiasts looking for easy maintenance-free living. Small lot, so no mowing. Economic...
Listed by Michelle Grant of Coldwell Banker Premier Real Estate
$8,750,000
Single Family Home
841 Winchester Road, Norfolk, CT 06098
Gracefully nestled at water's edge among lofty pines on over 115 utterly private and unspoiled woodland acres, this brea...
Listed by Jennifer Leahy of Compass Connecticut, LLC
$199,900
Single Family Home
9 Loomis Street, Winchester, CT 06098
ZONING IS TG Regulations are tailored to promote desired development patterns that promote an appropriate transition fro...
Listed by Kristen Duchene of Litchfield County Real Estate
$375,000
Single Family Home
323 East Wakefield Boulevard, Winchester, CT 06098
Charming 3-Bedroom Cape in Sought-After Lake Community. Welcome to this beautifully updated 3-bedroom, 2.5-bath Cape nes...
Listed by Heather Crabtree of Coldwell Banker Realty
$799,000
Single Family Home
139 Bunnell Street, Colebrook, CT 06098
Wonderful Old Colonial Farmhouse on 30+ Scenic Acres! Charming and full of character, this beautiful old farmhouse offer...
Listed by Mitzi Muller of William Raveis Real Estate
$579,999
Single Family Home
144 Marshall Street, Winchester, CT 06098
Welcome to your own private paradise! Nestled on an incredible 55 acres, this one-of-a-kind property offers peace, priva...
Listed by Monica Palmerie of RE/MAX RISE
$286,000
Single Family Home
421 Unity Place, Winchester, CT 06098
UPDATED | SERENE | CHARMING | 2 LOTS | This Highland Lake retreat is ideal for the 1st time homeowner, getaway retreat o...
Listed by Michelle Lorenzetti of Premier Re Group LLC
$269,900
Single Family Home
39 Finn Street, Winchester, CT 06098
Fabulous Opportunity to own in the Highland lake community. Walking distance to both beaches and boat launch. This adora...
Listed by Christine Hunter of Hunter Real Estate, LLC
$749,900
Multi-Family
39 South Main Street, Winchester, CT 06098
THREE PROPERTIES ONE PRICE!!! Includes single family, multi family & additional lot totaling 4.36 acres. 1. 3500 sq ft 2...
Listed by Ryan Horvay of Smith & DeGroat Real Estate
$239,900
Single Family Home
56 Lakeview Road, Winchester, CT 06098
Don't miss this 3 bedroom Ranch with a 2 car attached garage and an amazing view of Highland Lake - very close proximity...
Listed by Anthony Gioia of The Washington Agency
$400,000
Single Family Home
110 Rugg Brook Road, Winchester, CT 06098
Wow! Check out this beautiful, modern, colonial built in 1998 with over 2,000 square feet on 3+ level acres with an ingr...
Listed by Michelle Grant of Coldwell Banker Premier Real Estate
$204,000
Multi-Family
154 Wallens Street, Winchester, CT 06098
Investors & Owner Occupants, schedule your appointment NOW!!! Come view this 2-family home, price to sell!!! Located nea...
Listed by Adam Devine of Dorrance Realty
$1,495
Multi-Family
10 Maple Street #2, Winchester, CT 06098
Three bedroom, 2nd flr apartment close to town. Apartment features a washer dryer hook up, or can be provided for an ext...
Listed by Amanda Balaski of Northwest CT Realty
$269,900
Multi-Family
25 Center Street, Winchester, CT 06098
Introducing 25 Center St. - A Prime Mixed-Use Investment Property in Winsted! Looking for a great opportunity to expan...
Listed by Jessica Lopez of Our Home Realty Advisors
$295,000
Single Family Home
47 Moore Avenue, Winchester, CT 06098
Nestled in the charming town of Winchester, Connecticut, this beautifully remodeled ranch home offers the perfect blend ...
Listed by Suzie Larson of Turning Point Realty, LLC
$249,900
Single Family Home
150 Meadow Street, Winchester, CT 06098
Steeped in history and charm, this 1860-built home offers a blend of classic character and modern updates. With 8 rooms,...
Listed by David Sartirana of Northwest CT Realty
$230,000
Single Family Home
39 Orchard Street, Winchester, CT 06098
Welcome to this beautifully updated 3-bedroom, 1.5-bath colonial in the heart of Winsted! This home seamlessly blends cl...
Listed by Michael Flaherty Jr of Sullivan Real Estate Inc