Winchester, CT Homes

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  /38

  $1,200,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 1,556 Sq Ft

  722 Lake Dr, Winsted, CT 06098

  Welcome to lake living at its finest! Built in 2014 and first time on the market. Impeccably maintained, this stunning three bedroom, 3 bath home on Highland Lake, Winchester offers the perfect blend of comfort, style, and breathtaking VIEWS! From the moment you enter you will be captivated by the open-concept design, high-end finishes and panoramic lake views from both inside and out. Enjoy

  Joanne Donne The Washington Agency

  722 Lake Dr, Winsted, CT 06098
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  /37

  $2,450 Per Month

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • House for Rent

  91 Williams Ave, Winsted, CT 06098

  Welcome to this beautifully remodeled and spacious 3-bedroom, 2 full bathroom home in the heart of Winchester. Featuring hardwood floors throughout both the first and second levels, this home offers a warm and inviting layout with an eat-in kitchen that has a center island perfect for everyday living. Enjoy the convenience of a separate laundry room-washer and dryer included, high-efficiency gas

  Suzie Larson Turning Point Realty, LLC

  91 Williams Ave, Winsted, CT 06098
• 

  $300,000

  Sold May 11, 2026

  230 E Wakefield Blvd, Winsted, CT 06098

  • 3 Beds
  • 2 Baths
  • 1,536 Sq Ft
  • Built 1978

  Last Sold Summary

  • 6% Below List Price
  • $195/SF
  • 109 Days On Market

  Current Estimated Value $310,391

  Last Listing Agent Peter D'Addeo Commercial Services Realty

  230 E Wakefield Blvd, Winsted, CT 06098
• 

  Est $336,193

  Not Listed For Sale

  268 Smith Hill Rd, Colebrook, CT 06021

  • 2 Beds
  • 2 Baths
  • 1,635 Sq Ft
  • Built 1955

  268 Smith Hill Rd, Colebrook, CT 06021

  Last Sold Summary

  • 3% Above List Price
  • $199/SF
  • 122 Days On Market

  • Last Sold Price $324,900
  • Oct 11, 2024

  Last Listing Agent David Sartirana Northwest CT Realty
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  /37

  $779,900

  $9K PRICE DROP Pending

  • 5 Beds
  • 1.5 Baths
  • 1,258 Sq Ft

  156 Shore Dr, Winsted, CT 06098

  Summer is just around the corner, and this is your opportunity to own a highly sought-after waterfront property on the beautiful Highland Lake! Located on Shore Drive in the 1st Bay, this private 5-bedroom home offers breathtaking western exposure, giving you the perfect view of every sunset. Enjoy direct waterfront access and make the most of the flat, easy-to-maintain lot - ideal for outdoor

  Bryan Palladino Showcase Realty, Inc.

  156 Shore Dr, Winsted, CT 06098
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  /37

  $4,000 Per Month

  • 3 Beds
  • 2 Baths
  • 1,356 Sq Ft
  • House for Rent

  880 W Wakefield Blvd, Winsted, CT 06098

  Discover lakeside living at its finest with this fully renovated, fully furnished 3 bedroom, sleeps 10, 2 full-baths, family estate set on a half acre of professionally landscaped grounds overlooking picturesque Highland Lake. Located just 0.6 miles from Main Street Winsted and Red Barn Brewing, this property combines serene lakefront living with convenient access to local amenities. Enjoy use of

  Matt Crossen Coldwell Banker Realty

  880 W Wakefield Blvd, Winsted, CT 06098
• 

  $27,000

  Sold Apr 10, 2026

  48 Bridge St, Winsted, CT 06098

  • Land
  • 6,534 Sq Ft
  • $180,000 per Acre

  Last Sold Summary

  • 13% Above List Price
  • 359 Days On Market

  Last Listing Agent David Sartirana Northwest CT Realty

  48 Bridge St, Winsted, CT 06098
• 

  Est $113,421

  Not Listed For Sale

  11 Gibbs St Unit 6, Winsted, CT 06098

  • 1 Bed
  • 1 Bath
  • 570 Sq Ft
  • Built 1985

  11 Gibbs St Unit 6, Winsted, CT 06098

  Last Sold Summary

  • 22% Above List Price
  • $163/SF
  • 62 Days On Market

  • Last Sold Price $93,000
  • Apr 11, 2024

  Last Listing Agent Amanda Cole Carol Cole Real Estate, LLC
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  /39

  $499,000

  • 3 Beds
  • 2 Baths
  • 1,654 Sq Ft

  11 Old Creamery Rd, Colebrook, CT 06021

  FULLY RENOVATED! In addition this home is fully insulated, energy-efficient, and enhanced with solar panels for low utility costs. The open floor plan and cozy fireplace create the perfect space for gatherings, while multiple decks, an above-ground pool, and serene natural surroundings provide a tranquil retreat-ideal for year-round living or a weekend getaway. Located perfectly on a beautiful

  Rodrigo Aguiar William Raveis Real Estate

  11 Old Creamery Rd, Colebrook, CT 06021
• 

  

  /11

  $850 Per Month

  • 1 Bed
  • 1 Bath
  • 450 Sq Ft
  • House for Rent

  40 High St, Winsted, CT 06098

  This one bedroom is very tiny, it is approximately 400 square feet. Large kitchen and a living room. Low cost to heat and cool. Brand new kitchen floor. Washer and dryer.

  Alan Hill eXp Realty

  40 High St, Winsted, CT 06098
• 

  $800,000

  Sold Aug 04, 2025

  266 Perch Rock Trail, Winsted, CT 06098

  • 3 Beds
  • 2 Baths
  • 1,488 Sq Ft
  • Built 1928

  Last Sold Summary

  • 7% Above List Price
  • $538/SF
  • 0 Days On Market

  Current Estimated Value $817,982

  Last Listing Agent Laurie Murray KW Legacy Partners

  266 Perch Rock Trail, Winsted, CT 06098
• 

  Est $292,489

  Not Listed For Sale

  28 Maloney Ct, Winsted, CT 06098

  • 3 Beds
  • 2 Baths
  • 1,485 Sq Ft
  • Built 1940

  28 Maloney Ct, Winsted, CT 06098

  Last Sold Summary

  • 8% Above List Price
  • $182/SF
  • 59 Days On Market

  • Last Sold Price $270,000
  • Aug 15, 2024

  Last Listing Agent Beth Cantor Coldwell Banker
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  /28

  $425,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,781 Sq Ft

  123 Old North Rd, Winsted, CT 06098

  This one-of-a-kind custom Ranch is tucked well back from the road for exceptional privacy and was thoughtfully designed for its present owner. The stunning kitchen is truly the heart of the home, featuring a dramatic floor-to-ceiling stone fireplace, an expansive island with breakfast bar, an endless array of cabinets, and a built-in range with gas cooktop. The dining area flows seamlessly from

  Rick Berkenstock CENTURY 21 AllPoints Realty

  123 Old North Rd, Winsted, CT 06098
• 

  

  /21

  $2,200 Per Month

  • 3 Beds
  • 1 Bath
  • 1,042 Sq Ft
  • House for Rent

  34 Rock St, Winsted, CT 06098

  Lovely Colonial home recently remodeled, with large sun filled open concept living room, and separate dining area off of the fully equipped kitchen. Spacious carpeted mud room with ample room for coats, boots, and backpacks. Wood floors throughout home. Three bedrooms on second floor with nice views. Energy efficient gas heat. Great deck in rear overlooking back yard for entertaining and

  Terry Cubeddu Ameristar Royal Realty LLC

  34 Rock St, Winsted, CT 06098
• 

  $227,500

  Sold Nov 20, 2025

  174 Wallens St Unit H1, Winsted, CT 06098

  • 1 Bed
  • 2 Baths
  • 1,334 Sq Ft
  • Built 2007

  Last Sold Summary

  • 3% Below List Price
  • $171/SF
  • 91 Days On Market

  Last Listing Agent Kim D'Andrea William Pitt Sotheby's Int'l

  174 Wallens St Unit H1, Winsted, CT 06098
• 

  Est $321,663

  Not Listed For Sale

  103 Shore Dr, Winsted, CT 06098

  • 3 Beds
  • 1 Bath
  • 920 Sq Ft
  • Built 1942

  103 Shore Dr, Winsted, CT 06098

  Last Sold Summary

  • 3% Below List Price
  • $359/SF
  • 19 Days On Market

  • Last Sold Price $330,000
  • Aug 26, 2024

  Last Listing Agent Kathryn Ekstrom Haynes Real Estate Services
• 

  /2

  $749,999

  Coming Soon

  • 2 Beds
  • 2 Baths
  • 1,320 Sq Ft

  660 E Wakefield Blvd, Winsted, CT 06098

  Nestled along the coveted east side of Highland Lake, 660 East Wakefield Blvd offers a rare opportunity to create the waterfront retreat you've always imagined. Bursting with classic lake charm and timeless character, this home is ready for a new owner to make it their own and bring fresh vision to an unforgettable setting. Enjoy excellent water access for swimming, boating, kayaking, and

  Patrick Smith Smith & DeGroat Real Estate

  660 E Wakefield Blvd, Winsted, CT 06098
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  /7

  $1,350 Per Month

  • 2 Beds
  • 1 Bath
  • 1,250 Sq Ft
  • House for Rent

  5 Brookside Ave, Winsted, CT 06098

  Large 2br apartment, gas heating, washer and dryer included and in unit. Certain pets allowed with extra pet deposit. Near Gilbert Highschool. 2 months security deposit required and background check. Priced to rent quickly.

  Mark Digalbro Mark DiGalbo Realty LLC

  5 Brookside Ave, Winsted, CT 06098
• 

  $690,000

  Sold Feb 06, 2026

  151 Losaw Rd, Winsted, CT 06098

  • 5 Beds
  • 2.5 Baths
  • 2,950 Sq Ft
  • Built 2007

  Last Sold Summary

  • 14% Below List Price
  • $234/SF
  • 164 Days On Market

  Current Estimated Value $685,852

  Last Listing Agent Breanna Goebel Compass Connecticut, LLC

  151 Losaw Rd, Winsted, CT 06098
• 

  Est $303,085

  Not Listed For Sale

  139 Boyd St, Winsted, CT 06098

  • 4 Beds
  • 2 Baths
  • 2,104 Sq Ft
  • Built 1885

  139 Boyd St, Winsted, CT 06098

  Last Sold Summary

  • 29% Above List Price
  • $112/SF
  • 29 Days On Market

  • Last Sold Price $235,000
  • May 26, 2023

  Last Listing Agent Mary Mary LeBlanc Realty
• 

  

  /40

  $895,000

  • 4 Beds
  • 2 Baths
  • 3,088 Sq Ft

  469 Platt Hill Rd, Winsted, CT 06098

  HOME-LAND -BARN. A TRUE NEW ENGLAND CLASSIC PROPERTY IN A POST CARD SETTING! For the Discerning Customer, whether You're an ANTIQUARIAN, HORSE & ANIMAL LOVER, or just seeking for a PEACEFUL & TRANQUIL LOCATION, this LITCHFIELD COUNTY HOME could possibly fit your Criteria. Stately 1789 , 11 Room 3,088 Sq. Ft. Colonial expresses Love, Warmth & Care. From the Solid Beams, Chestnut Wide-Board Floors,

  Marshall Cohen Cohen Agency

  469 Platt Hill Rd, Winsted, CT 06098
• 

  $277,000

  Sold Oct 09, 2025

  12 Cherry St, Winsted, CT 06098

  • 4 Beds
  • 1 Bath
  • 1,492 Sq Ft
  • Built 1800

  Last Sold Summary

  • 4% Below List Price
  • $186/SF
  • 54 Days On Market

  Current Estimated Value $285,021

  Last Listing Agent Susan MCGHEE The Washington Agency

  12 Cherry St, Winsted, CT 06098
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  Not Listed For Sale

  174 Wallens St Unit D2, Winsted, CT 06098

  • 2 Beds
  • 2 Baths
  • 1,352 Sq Ft
  • Built 2005

  174 Wallens St Unit D2, Winsted, CT 06098

  Last Sold Summary

  • 6% Above List Price
  • $166/SF
  • 39 Days On Market

  • Last Sold Price $225,000
  • Mar 12, 2024

  Last Listing Agent Ashley Church Turning Point Realty, LLC
• 

  

  /35

  $625,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 2,144 Sq Ft

  162 Spencer Hill Rd, Winsted, CT 06098

  Experience the beauty and privacy of this pristine log home set on 16.53 picturesque acres. A long, level gravel driveway welcomes you to the expansive 43' x 8' covered front porch, the perfect place to enjoy breathtaking winter sunrises overlooking your own blueberry bushes. Surrounded by abundant wildlife, this property offers a true country retreat. Inside, you'll find soaring ceilings, a

  Kelly Sullivan Sullivan Real Estate Inc

  162 Spencer Hill Rd, Winsted, CT 06098
• 

  $230,000

  Sold Mar 18, 2026

  106 Rockwell St, Winsted, CT 06098

  • 6 Beds
  • 3 Baths
  • 1,874 Sq Ft
  • Built 1850

  Last Sold Summary

  • 23% Below List Price
  • $123/SF
  • 23 Days On Market

  Current Estimated Value $231,033

  Last Listing Agent Dawn Rousseau Showcase Realty, Inc.

  106 Rockwell St, Winsted, CT 06098
• 

  Not Listed For Sale

  174 Wallens St Unit C3, Winsted, CT 06098

  • 2 Beds
  • 2.5 Baths
  • 1,946 Sq Ft
  • Built 2005

  174 Wallens St Unit C3, Winsted, CT 06098

  Last Sold Summary

  • 14% Above List Price
  • $128/SF
  • 9 Days On Market

  • Last Sold Price $250,000
  • Oct 31, 2023

  Last Listing Agent Amanda Balaski Northwest CT Realty
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  /39

  $795,000

  Pending

  • 4 Beds
  • 2 Baths
  • 1,373 Sq Ft

  258 Perch Rock Trail, Winsted, CT 06098

  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

  Nancy Reardon Berkshire Hathaway NE Prop.

  258 Perch Rock Trail, Winsted, CT 06098
• 

  $225,000

  Sold Jul 03, 2025

  39 Baker St, Winsted, CT 06098

  • 5 Beds
  • 2 Baths
  • 1,612 Sq Ft
  • Built 1900

  Last Sold Summary

  • $140/SF
  • 166 Days On Market

  Current Estimated Value $222,764

  Last Listing Agent Christine Hunter Hunter Real Estate, LLC

  39 Baker St, Winsted, CT 06098
• 

  Est $273,812

  Not Listed For Sale

  17 Colony Dr, Winsted, CT 06098

  • 3 Beds
  • 1.5 Baths
  • 1,040 Sq Ft
  • Built 1965

  17 Colony Dr, Winsted, CT 06098

  Last Sold Summary

  • 11% Above List Price
  • $238/SF
  • 72 Days On Market

  • Last Sold Price $247,000
  • Dec 14, 2023

  Last Listing Agent David Sartirana Northwest CT Realty
• 

  

  /9

  $469,900

  Coming Soon

  • 3 Beds
  • 2 Baths
  • 1,768 Sq Ft

  9 Loomis St, Winsted, CT 06098

  Spacious 3 to 4 Bedroom Colonial Style Home on a 0.35 Acre Lot, plus located on a No Through Street. Beautifully Remodeled from "TOP TO BOTTOM" for Energy Efficient Living. Redesigned Country Style Kitchen offers Ample Cabinetry and includes New Oven/Range, Microwave, Refrigerator & Dishwasher.. 27' x 12' Living/Dining Combo with Bay/Bow Window that takes in Natural Light on those Sunny Days!

  Marshall Cohen Cohen Agency

  9 Loomis St, Winsted, CT 06098
• 

  $1,575,000

  Sold Jun 30, 2025

  508 W Wakefield Blvd, Winsted, CT 06098

  • 7 Beds
  • 4 Baths
  • 2,687 Sq Ft
  • Built 1890

  Last Sold Summary

  • 5% Below List Price
  • $586/SF
  • 316 Days On Market

  Current Estimated Value $1,576,076

  Last Listing Agent Pierre Moran William Pitt Sotheby's Int'l

  508 W Wakefield Blvd, Winsted, CT 06098
• 

  Est $255,262

  Not Listed For Sale

  159 Pratt St, Winsted, CT 06098

  • 3 Beds
  • 2 Baths
  • 1,176 Sq Ft
  • Built 1900

  159 Pratt St, Winsted, CT 06098

  Last Sold Summary

  • 8% Above List Price
  • $201/SF
  • 11 Days On Market

  • Last Sold Price $236,500
  • Aug 02, 2023

  Last Listing Agent Cindy Breckheimer Forever Homes Real Estate LLC
• 

  

  /21

  $360,000

  Pending

  • 3 Beds
  • 1.5 Baths
  • 1,312 Sq Ft

  262 Holabird Ave, Winsted, CT 06098

  Discover the perfect blend of small time charm with many conveniences close at hand! This well maintained, warm and inviting, 1 owner home offers it all! Having beautiful Highland Lake in this community is certainly one of many pluses! The renovated eat in kitchen offers granite counter tops, stainless steel appliances and access to a beautiful new Trex deck! Along with new decking, new windows

  Mary Anne Casey D. Beckley Realty

  262 Holabird Ave, Winsted, CT 06098
• 

  $360,000

  Sold Feb 25, 2026

  187 Torringford St, Winsted, CT 06098

  • 4 Beds
  • 1.5 Baths
  • 2,365 Sq Ft
  • Built 1800

  Last Sold Summary

  • 16% Below List Price
  • $152/SF
  • 109 Days On Market

  Current Estimated Value $370,066

  Last Listing Agent Jessica Washington William Raveis Real Estate

  187 Torringford St, Winsted, CT 06098
• 

  Est $236,801

  Not Listed For Sale

  17 Front St, Winsted, CT 06098

  • 4 Beds
  • 1.5 Baths
  • 1,600 Sq Ft
  • Built 1915

  17 Front St, Winsted, CT 06098

  Last Sold Summary

  • 155% Above List Price
  • $58/SF
  • 20 Days On Market

  • Last Sold Price $93,000
  • Jul 06, 2023

  Last Listing Agent David Sartirana Northwest CT Realty
• 

  

  /5

  $200,000

  • Land
  • 15.9 Acres
  • $12,579 per Acre

  00 Chapel Rd, Winchester, CT 06098

  Look no further for A Very Private location to build your Dream Home. A Wooded Hill top building site overlooking beautiful Winchester Center which can provide peace and solitude for your home or vacation retreat . Historical Winchester Center is deep with rich heritage and History of Winchester. Convenient access agreement to the Rear lot is though 151 Chapel Rd. property.

  Linda Ganem Borla & Associates Real Estate

  00 Chapel Rd, Winchester, CT 06098
• 

  $315,000

  Sold Apr 09, 2026

  25 Center St, Winsted, CT 06098

  • 3 Beds
  • 2.5 Baths
  • 2,754 Sq Ft
  • Built 1860

  Last Sold Summary

  • 2% Below List Price
  • $114/SF
  • 175 Days On Market

  Last Listing Agent Tony Goia The Washington Agency

  25 Center St, Winsted, CT 06098
• 

  Not Listed For Sale

  319 Taylor Brook Rd, Winsted, CT 06098

  • 4 Beds
  • 2.5 Baths
  • 2,969 Sq Ft
  • Built 1990

  319 Taylor Brook Rd, Winsted, CT 06098

  Last Sold Summary

  • 6% Below List Price
  • $158/SF
  • 4 Days On Market

  • Last Sold Price $470,000
  • Aug 01, 2023

  Last Listing Agent Heidi Picard-Ramsay Berkshire Hathaway Home Services
• 

  

  /4

  $289,000

  Coming Soon

  • 3 Beds
  • 1 Bath
  • 1,008 Sq Ft

  104 Maloney Ct, Winsted, CT 06098

  Perched on desirable Wallens Hill with beautiful western sunset views, this lovingly maintained 3 bed 1957 ranch is full of warmth, charm, and pride of ownership. Bright and sunny throughout, the home offers 1,008 square feet of comfortable living space with hardwood floors, central air conditioning, and an easy-flow layout designed for everyday living. The spacious eat-in kitchen features oak

  Lisa Garten Johnson Turning Point Realty, LLC

  104 Maloney Ct, Winsted, CT 06098
• 

  $151,000

  Sold Feb 20, 2026

  155 Rockwell St, Winsted, CT 06098

  • 3 Beds
  • 1 Bath
  • 1,317 Sq Ft
  • Built 1953

  Last Sold Summary

  • 5% Below List Price
  • $115/SF
  • 11 Days On Market

  Current Estimated Value $188,255

  Last Listing Agent Joseph Caslin Sailpoint Property Group

  155 Rockwell St, Winsted, CT 06098

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