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82 Properties Available
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$325,000
Multi-Family
267 Rockwell Street, Winchester, CT 06098
Great opportunity to own a spacious, fully rented 3-family property on a level .86 acre lot, just a short walk to Hi...
Listed by Austin Brochu of Sullivan Real Estate Inc
$385,000
Single Family Home
147 Smith Hill Road, Winchester, CT 06098
Tucked away on a wooded lot, this meticulously maintained Cape features 4 spacious bedrooms and a full bathroom on each ...
Listed by Sharon Gilson of Northwest CT Realty
$245,900
Single Family Home
1 Hamill Drive, Winchester, CT 06098
This 1973 raised ranch is a charming home tucked away on a peaceful cul-de-sac in the country. The home features three b...
Listed by Nancy Bard of Bard Real Estate, LLC
$194,900
Single Family Home
415 North Main Street, Winchester, CT 06098
This charming 3-bedroom, 1-bath single-family home offers a great opportunity for homeowners or investors looking to bui...
Listed by Jeffrey Liskin of Northwest CT Realty
$1,350
Multi-Family
23 Allen Street, Winchester, CT 06098
Discover your new home in this delightful 2-bedroom, 1-bathroom apartment offering 1,100 square feet of thoughtfully des...
Listed by Jeffrey Liskin of Northwest CT Realty
$1,650
Multi-Family
23 Wetmore Avenue #2, Winchester, CT 06098
Available 8-1-25. Immaculate second floor unit, recently renovated, super clean and bright. Quiet second floor, spacious...
Listed by Suzie Larson of Turning Point Realty, LLC
$299,000
Single Family Home
15 John Street, Winchester, CT 06098
Feels Like New - Without the New Construction Price! Looking for a move-in ready home that won't break the bank? This fr...
Listed by Amanda Balaski of Northwest CT Realty
$1,200
Single Family Home
161 Lake Street, Winchester, CT 06098
This freshly painted, stand-alone 1-bedroom rental offers privacy, comfort, and convenience just steps from the shores o...
Listed by David Sartirana of Northwest CT Realty
$287,750
Single Family Home
12 Cherry Street, Winchester, CT 06098
This Home is Modern day updates Meets Old World Charm...The Updated Kitchen offers granite counter tops, custom cabinetr...
Listed by Sue McGhee of The Washington Agency
$1,375
Multi-Family
45 center Street, Winchester, CT 06098
Beautifully remodeled, one bedroom, 1st floor apartment. Includes heat and internet. Washer/dryer can be added for an ad...
Listed by Amanda Balaski of Northwest CT Realty
$750,000
Single Family Home
266 Perch Rock Trail, Winchester, CT 06098
Wake up to sparkling water views and savor the serenity of lakefront living in this storybook Cape Cod-style retreat on ...
Listed by Laurie Murray of KW Legacy Partners
$1,295,000
Single Family Home
722 Lake Drive, Winchester, CT 06098
Welcome to lake living at its finest! Built in 2014 and first time on the market. Impeccably maintained, this stunning t...
Listed by Joanne Donne of The Washington Agency
$299,900
Single Family Home
17 Adams Street, Winchester, CT 06098
Nestled in the charming New England town of Winsted, this classic three-bedroom, two-bathroom home at 17 Adams Street of...
Listed by Michelle Grant of Coldwell Banker Premier Real Estate
$234,900
Single Family Home
99 Norfolk Road, Winchester, CT 06098
99 Norfolk Rd, Winsted CT - Opportunity Knocks! This cute 3-bedroom Cape sits proudly on 1.3 acres and is ready for its ...
Listed by Lisa McCarthy of Coldwell Banker Realty
$175,000
Single Family Home
100 Norfolk Road, Winchester, CT 06098
Endless Potential on 3.7 acres! 4 bedroom and 2 bath cape is a single-family home that was formerly used as a small home...
Listed by Katie Breitkreutz of Dave Jones Realty, LLC
$1,145
Multi-Family
174 Main Street #A, Winchester, CT 06098
One bedroom apartment on the first floor. Large kitchen and a recently remodeled bath. Washer/dryer can be added in the ...
Listed by Amanda Balaski of Northwest CT Realty
$380,000
Single Family Home
279 Pratt Street, Winchester, CT 06098
Perched atop Pratt Street in Winsted, this traditional farmhouse offers a peaceful retreat on a generous 1.75-acre lot. ...
Listed by Michelle Grant of Coldwell Banker Premier Real Estate
$1,500
Multi-Family
141 Boyd Street, Winchester, CT 06098
Stop by and check out this charming duplex style rental close to the highland beach public boat launch and Holland beach...
Listed by Mary Leblanc of Mary LeBlanc Realty
$1,400
Single Family Home
936 Main Street #7, Winchester, CT 06098
Recently purchased and re-built manufactured home community in Winsted in final stages of being completed. The entrance ...
Listed by Michael Block of Building Blocks LLC
$779,900
Single Family Home
111 South Road, Winchester, CT 06098
Perched up higher than the rest with sweeping views up a private driveway in beautiful Winchester Center you'll find thi...
Listed by Dawn Rousseau of Showcase Realty, Inc.
$419,900
Single Family Home
17 Woodland Avenue, Winchester, CT 06098
Beautiful 3 bedroom updated colonial walking distance to Highland lake beach.Large eat in kitchen with granite counter t...
Listed by Vincent Devico of Showcase Realty, Inc.
$285,000
Multi-Family
126 Williams Avenue, Winchester, CT 06098
Excellent investment opportunity! This fully occupied two-family home generates a steady $3,300 in monthly rental income...
Listed by Michelle Grant of Coldwell Banker Premier Real Estate
$589,900
Single Family Home
102 Hollow Hill Road, Winchester, CT 06098
Highest & Best Due by 6/17/2025 at 5PM. First time to the market this turnkey 2,692 sq ft Grand Ranch is nestled in on 2...
Listed by Dawn Rousseau of Showcase Realty, Inc.
$375,000
Single Family Home
181 Torringford Street, Winchester, CT 06098
Charming Colonial on Nearly an Acre! Discover the perfect blend of comfort and space in this 3-bedroom, 1.5-bathroom Col...
Listed by Michelle Grant of Coldwell Banker Premier Real Estate