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$325,000
Multi-Family
62 Fruit Street, Winchester, CT 06098
62-64 Fruit Street in Winchester offers a rare opportunity to acquire a turnkey property located in one of the town's mo...
Listed by Antonio De La Cruz of Eagle Eye Realty PLLC

$235,000
Condo
174 Wallens Street #APT H1, Winchester, CT 06098
Discover effortless living in this inviting home at the sought-after Clockmaker's Hill community. The thoughtfully desig...
Listed by Kim D'andrea of William Pitt Sotheby's Int'l

$449,900
Single Family Home
51 Pratt Street, Winchester, CT 06098
This stunning Renovated home is perfectly situated in the beautiful town of Winsted could be yours! Just a leisurely wal...
Listed by Arlene Gonzalez of The Gonzalez Property Group

$255,000
Single Family Home
22 Curtice Street, Winchester, CT 06098
Step into timeless elegance with this beautifully updated colonial-style home, where classic charm meets modern convenie...
Listed by Terence Dominick of Complete Real Estate

$150,000
Condo
38 Riveredge Drive #38, Winchester, CT 06098
End Unit Ranch-Style Condo - Winchester. Discover privacy and convenience in this well-maintained one-level end unit nes...
Listed by Suzie Larson of Turning Point Realty, LLC

$289,000
Single Family Home
160 Walnut Street, Winchester, CT 06098
Have you been looking to find a classic colonial home set in Litchfield county? This quintessential home is it! The firs...
Listed by Jeremy Beamer of William Raveis Real Estate

$399,900
Multi-Family
27 Thibault Avenue, Winchester, CT 06098
Here is your perfect chance to build your investment portfolio! 2 houses and a vacant lot create the perfect investment...
Listed by Cathy Macias of Northwest CT Realty

$394,900
Single Family Home
548 East Wakefield Boulevard, Winchester, CT 06098
Start your lakeside legacy at this rare waterfront cottage on Highland Lake. With stunning westerly views and a private ...
Listed by Amy Rio of Executive Real Estate Inc.

$355,750
Single Family Home
126 Forest Avenue, Winchester, CT 06098
Charming Cape 2 minutes to Highland Lake. Welcome to this one owner, 3 bedroom, two bath Cape Cod home offering over 1,8...
Listed by Joanne Donne of The Washington Agency

$350,000
Single Family Home
157 Elm Street, Winchester, CT 06098
Victorian Charm Meets Modern Potential - 5-Bedroom Home Across from Pearson School Step into timeless elegance with thi...
Listed by Doreen Gagnon of Coldwell Banker Realty

$299,999
Single Family Home
36 Whiting Street, Winchester, CT 06098
Newly updated 3 bedroom 2.5 bath colonial with large front porch overlooking the Mad River. Close to downtown and town c...
Listed by Brandon Riley of eXp Realty

$295,000
Single Family Home
128 Danbury Quarter Road, Winchester, CT 06098
First-time homebuyers and downsizers take notice!. Some improvements have been done in this cozy Ranch boasting a metal ...
Listed by Kim Trumbull of William Raveis Real Estate

$399,900
Single Family Home
212 Spencer Hill Road, Winchester, CT 06098
Welcome to your peaceful retreat in the heart of Winchester - a quiet, scenic town surrounded by natural beauty. Tucked ...
Listed by Tammy Powling of Coldwell Banker Realty

$375,000
Single Family Home
111 Old North Road, Winchester, CT 06098
Two parcels for the price of one! Discover this beautifully maintained split-level ranch at 111 Old North Road in Winche...
Listed by Chris Clarke of Coldwell Banker Realty

$197,500
Condo
111 Riverton Road #APT 37, Winchester, CT 06098
Picture yourselves in this bright, roomy end unit condominium with room to spare! Totally renovated bathtub and fixtures...
Listed by Sandy Marchetti of The Washington Agency

$799,000
Single Family Home
151 Losaw Road, Winchester, CT 06098
Feel worlds away while being less than 2 miles to town amenities in this like-new retreat nestled on an expansive 11.59-...
Listed by Breanna Goebel of Compass Connecticut, LLC

$199,900
Single Family Home
14 Curtice Street, Winchester, CT 06098
Attention investors and buyers looking to build equity! Welcome to 14 Curtice Street, a home has incredible value and po...
Listed by Michael Johnson of Lock and Key Realty, Inc

$249,900
Single Family Home
42 Maloney Court, Winchester, CT 06098
Cute affordable turn key Ranch. Situated on a corner lot in a quiet convenient neighborhood. 3 bedroom's 1 bath. Basemen...
Listed by James Walsh of James Walsh

$380,000
Single Family Home
166 Torringford Street, Winchester, CT 06098
Nothing to do but move right in to this meticulous colonial farmhouse nestled in the Litchfield Hills. This unique home ...
Listed by Lana Van Valkenburgh of Vision Real Estate

$250,000
Single Family Home
115 Laurel Way, Winchester, CT 06098
Welcome to 115 Laurel Way! Tucked away in a peaceful neighborhood surrounded by nature, this charming well maintained 1-...
Listed by Jill Menard of Realty One Group Cutting Edge

$189,900
Single Family Home
14 Pratt Street, Winchester, CT 06098
Don't let the outside fool you! Perfect alternative to condominium living! No HOA and plenty of off street parking at th...
Listed by Amy Sartirana of Northwest CT Realty

$1,900
Single Family Home
12 Charles Street, Winchester, CT 06098
Adorable two-bedroom cottage near Highland Lake available first week of October. Tile in kitchen, new lighting and gleam...
Listed by Jessica Chavez of Turning Point Realty, LLC

$1,375
Multi-Family
111 Rockwell Street #2nd Floor, Winchester, CT 06098
Bright and peaceful 2-bedroom, 1-bath second-floor apartment featuring a charming kitchen and a private deck. Convenient...
Listed by Colin Murray of Dorrance Realty

$1,149,000
Single Family Home
674 East Wakefield Boulevard, Winchester, CT 06098
Experience premier waterfront living on Highland Lake in this beautifully maintained 3-bedroom, 3-bath home offering stu...
Listed by Matthew Smith of Smith & DeGroat Real Estate