Homes in ZIP Code 06098

• 

  

  

  /35

  $849,900

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

  119 W Wakefield Blvd, Winsted, CT 06098

  Have you been dreaming of breathtaking lake views and a property that is truly special, unique, and turn-key? This exceptional home includes 50 feet of waterfront access with a boat dock and lift, making it a dream for lake enthusiasts! Nestled across from the tranquil First Bay, this beautifully renovated two-family home can be enjoyed as a single-family retreat or an income-generating

  Mela Veltri Case KW Legacy Partners

  119 W Wakefield Blvd, Winsted, CT 06098
• 

  $236,434 Sold Aug 25, 2025

  • 674 Sq Ft
  • $351/SF
  • 40 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1923

  343 W Wakefield Blvd, Winsted, CT 06098

  Your oasis awaits!!! Schedule your appointment today and come view this adorable Bungalow. There is so much potential to be made here. Bring your ideas and creativity as the seller is motivated, bring all offers!!!

  Patrick Precourt Dorrance Realty

  343 W Wakefield Blvd, Winsted, CT 06098
• 

  Est $354,111 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,249 Sq Ft

  143 Mountain Rd, Winsted, CT 06098

  143 Mountain Rd, Winsted, CT 06098
• 

  

  

  /40

  $2,199,000

  • 9 Beds
  • 5.5 Baths
  • 7,000 Sq Ft

  431 W Wakefield Blvd, Winsted, CT 06098

  LOCAL NEWS JUST ANNOUNCED THAT WINSTED WAS 1 OF THE MOST DESIRABLE TOWNS TO LIVE WITH EMPHASIS ON BEAUTIFUL HIGHLAND LAKE. This waterfront estate at 431 W. Wakefield Blvd in Winchester, CT, is not just a home but the ultimate Highland Lake lifestyle. Imagine waking up each day to stunning lake views, with endless seasonal activities awaiting just beyond your doorstep. In the summer, dive into

  Lisa Ogren Berkshire Hathaway NE Prop.

  431 W Wakefield Blvd, Winsted, CT 06098
• 

  $321,000 Sold Aug 25, 2025

  • 2,623 Sq Ft
  • $122/SF
  • 7 Days On Market

  • 3 Beds
  • 5 Baths
  • Built 1900

  29 Walnut St, Winsted, CT 06098

  Introducing 29 Walnut: a grand Victorian home with a front porch view complimented by perennial rose gardens, a terrace fit for garden parties, and a large back yard. Upon entry, look upward to high ceilings, a spacious entryway and a grand, swirling staircase. Note precise finish work and period correct trim as you move into the open living, kitchen, and dining area with a chic half bath. Make

  Rosemary Scanlon Coldwell Banker Realty

  29 Walnut St, Winsted, CT 06098
• 

  Est $217,137 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,759 Sq Ft

  11 Orchard St, Winsted, CT 06098

  11 Orchard St, Winsted, CT 06098
• 

  

  /5

  $158,000

  • Land
  • 1.18 Acres
  • $133,898 per Acre

  843-845 (lots - 10A, E Wakefield Blvd, Winchester, CT 06098

  1.18 Acre ,Approximately 201 Ft Road fro . ntage )Lightly wooded E. Wakefield Blvd. lot located at the end of 3rd Bay . Panoramic view overlooking the length or lake. Survey , Zoning HL regulations and Deed are available , and Access is also available off E. Mtn Road . Survey shows Town of Winchester parcel with warterfront access Rare opportunity to build your dream home . , SELLER WILL

  David D'Amore Northwest CT Realty

  843-845 (lots - 10A, E Wakefield Blvd, Winchester, CT 06098
• 

  $172,500 Sold Aug 25, 2025

  • 1,446 Sq Ft
  • $119/SF
  • 43 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1900

  415 N Main St, Winsted, CT 06098

  This charming 3-bedroom, 1-bath single-family home offers a great opportunity for homeowners or investors looking to build equity. Located close to downtown Winsted, this home features newer kitchen appliances, including a natural gas range, and a convenient main-level laundry area tucked inside a cozy pantry. A pellet stove in the dining room-currently not hooked up-adds potential for

  Jeffrey Liskin Northwest CT Realty

  415 N Main St, Winsted, CT 06098
• 

  Est $306,028 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 960 Sq Ft

  303 E Wakefield Blvd, Winsted, CT 06098

  303 E Wakefield Blvd, Winsted, CT 06098
• 

  

  /5

  $295,000

  • Land
  • 51 Acres
  • $5,784 per Acre

  393 Winchester Rd, Winsted, CT 06098

  WINCHESTER CREST 51 acres of forested gently rolling land sited upland in Winchester Center. There is a former homesite and multiple choices for additional homesites affording complete privacy. There is abundant wildlife, trails, intermittent streams, dense and sparse forest. Perfect for year round home site, weekend retreat or recreational land.

  Tom McGowan Elyse Harney Real Estate

  393 Winchester Rd, Winsted, CT 06098
• 

  $250,000 Sold Aug 22, 2025

  • 1,168 Sq Ft
  • $214/SF
  • 2 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1920

  233 Grantville Rd, Winsted, CT 06098

  Welcome to 233 Grantville Rd-a delightful 1,168 sq ft cottage-style home nestled on a quiet, level country lot in Winchester. Inside, you'll find a cozy kitchen, a comfortable living room, a modest bedroom, a small office, and a spacious bonus room that can serve as a second bedroom, family room, or flexible living space to suit your needs.The property also features an attached two-story

  David Sartirana Northwest CT Realty

  233 Grantville Rd, Winsted, CT 06098
• 

  Est $255,057 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,634 Sq Ft

  151 Hinsdale Ave, Winsted, CT 06098

  151 Hinsdale Ave, Winsted, CT 06098
• 

  /2

  $299,900

  • Land
  • 63 Acres
  • $4,760 per Acre

  32 Norfolk Rd, Winchester, CT 06098

  63-Acre Rural Retreat Abutting Algonquin State Forest - A Nature Lover's Dream! Discover the perfect blend of seclusion and accessibility with this 63-acre wooded paradise, directly abutting Algonquin State Forest. Located on a state highway and directly across from a scenic dry dam, this unique parcel provides endless possibilities-whether you're looking to build your dream home, start a

  David D'Amore Northwest CT Realty

  32 Norfolk Rd, Winchester, CT 06098
• 

  $281,000 Sold Aug 13, 2025

  • Land
  • 0.61 Acre
  • $460,656 per Acre

  • 371 Days On Market

  711 W Wakefield Blvd, Winchester Center, CT 06098

  Build your DREAM home! Largest lot available on the lake with great views and parking! Will build to suite. Don't miss this wonderful opportunity! WELL IS LOT CORNER at Forest Ave FRONTAGES ARE MARKED IN RED. +-a2 map and topo in documents.

  Peter Kores The Washington Agency

  711 W Wakefield Blvd, Winchester Center, CT 06098
• 

  Est $351,498 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,664 Sq Ft

  5 Hillside Ave, Winsted, CT 06098

  5 Hillside Ave, Winsted, CT 06098
• 

  /2

  $69,000

  • Land
  • 2 Acres
  • $34,500 per Acre

  503 N Main St, Winsted, CT 06098

  Prime Building Lot Near Downtown & Highland Lake-Discover the perfect setting for your dream home on this 2 acre lot at 503 N Main Street. The Property has over 500' of road frontage, permitted uses include; accessory residential uses, family day care home, farm, seasonal cottages, single family dwelling. The property offers a peaceful atmosphere while maintaining easy access to downtown

  Charles Albertario William Raveis Real Estate

  503 N Main St, Winsted, CT 06098
• 

  $425,000 Sold Aug 13, 2025

  • 2,086 Sq Ft
  • $204/SF
  • 3 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1970

  50 Lakeview Rd, Winsted, CT 06098

  Located just a short stroll from Holland Beach and only a 3-minute drive to the public boat launch, this charming Colonial offers the perfect blend of comfort, convenience, and year-round recreation. Nestled on a level corner lot in a well-established neighborhood, this home invites you to enjoy all the amenities of Connecticut's second-largest lake - from kayaking and boating to lakeside walks

  Paula Nelson William Raveis Real Estate

  50 Lakeview Rd, Winsted, CT 06098
• 

  Est $233,954 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,380 Sq Ft

  36 S Main St, Winsted, CT 06098

  36 S Main St, Winsted, CT 06098
• 

  /2

  $59,900

  • Land
  • 0.41 Acre
  • $146,098 per Acre

  105,107 E Mountain Rd, Winchester, CT 06098

  105 & 107 Mountain Road parcels are contiguous and located on a dirt road . . Deed indicates right of way to Highland lake water frontage within walking distance. See documents attached for Deed , Site plan, Peculation tests , Survey and Septic testing available . Possible city sewer access at buyers expense . Seller will consider financing with a minimum of 15% DOWN PAYMENT FOR A 2 YEAR BALLOON

  David D'Amore Northwest CT Realty

  105,107 E Mountain Rd, Winchester, CT 06098
• 

  $540,000 Sold Aug 06, 2025

  • 1,744 Sq Ft
  • $310/SF
  • 51 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1980

  144 Marshall St, Winsted, CT 06098

  Welcome to your own private paradise! Nestled on an incredible 55 acres, this one-of-a-kind property offers peace, privacy, and the perfect blend of comfort and outdoor adventure. Featuring a ranch-style layout with 3 bedrooms and 2 full baths, this home is ideal for easy one-level living. Step inside to find hardwood floors throughout and three cozy fireplaces that bring warmth and character to

  Monica Palmerie RE/MAX RISE

  144 Marshall St, Winsted, CT 06098
• 

  Est $210,623 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,204 Sq Ft

  111 Riverton Rd Unit 55, Winsted, CT 06098

  111 Riverton Rd Unit 55, Winsted, CT 06098
• 

  

  /25

  $184,900 Pending

  • 3 Beds
  • 1 Bath
  • 980 Sq Ft

  99 Norfolk Rd, Winsted, CT 06098

  Opportunity awaits at this charming 3-bedroom Cape set on 1.3 acres in a peaceful country setting. Nicely perched high and set back from the road, this home offers privacy, curb appeal, and plenty of potential. With vinyl siding, replacement windows, a newer septic, and a classic layout, the bones are here - now bring your ideas and make it shine! Perfect for contractors, investors, or handy

  Lisa McCarthy Coldwell Banker Realty

  99 Norfolk Rd, Winsted, CT 06098
• 

  $320,000 Sold Aug 06, 2025

  • 1,752 Sq Ft
  • $183/SF
  • 24 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1963

  141 Maloney Ct, Winsted, CT 06098

  A charming ranch-style home, located in a desirable area, offers the convenience of single-level living. It features 4 bedrooms and 3 bathrooms, making it perfect for families or anyone in need of extra space. Upon entering the main floor, you'll find a spacious living room filled with natural light, which creates a warm and inviting atmosphere. The kitchen provides ample counter space and opens

  Marcy D'Angelo Coldwell Banker Realty

  141 Maloney Ct, Winsted, CT 06098
• 

  Est $216,055 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,204 Sq Ft

  111 Riverton Rd Unit 45, Winsted, CT 06098

  111 Riverton Rd Unit 45, Winsted, CT 06098
• 

  

  /32

  $259,000 Pending

  • 4 Beds
  • 2 Baths
  • 2,444 Sq Ft

  10 Crescent St, Winsted, CT 06098

  A multi-family home close to town with spacious bedrooms and living space. Plenty of storage and parking. Close to all forms of transportation, schools and shopping. Come check it out today!!

  Thomas Mele Dorrance Realty

  10 Crescent St, Winsted, CT 06098
• 

  $800,000 Sold Aug 04, 2025

  • 1,488 Sq Ft
  • $538/SF
  • 0 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1928

  266 Perch Rock Trail, Winsted, CT 06098

  Wake up to sparkling water views and savor the serenity of lakefront living in this storybook Cape Cod-style retreat on Highland Lake's desirable east side. Tucked away on a peaceful private lane, this year-round haven offers 3 bedrooms & 2 full baths, perfectly blending classic charm with modern comfort. Step into the spacious kitchen, where sun-drenched mornings begin at the breakfast nook and

  Laurie Murray KW Legacy Partners

  266 Perch Rock Trail, Winsted, CT 06098
• 

  Est $238,246 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,310 Sq Ft

  20 Gay St, Winsted, CT 06098

  20 Gay St, Winsted, CT 06098
• 

  

  /26

  $279,999 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,542 Sq Ft

  73 Norfolk Rd, Winsted, CT 06098

  New to the market! Check out this upgraded colonial home with 3 bedrooms and 2.5 baths located on a 2.6-acre wooded lot with a patio, shed and paths for walking and quadding. Enjoy entertaining in the open layout with an eat in kitchen and new cabinets. Relax in the cozy living room with hard wood floors, a fireplace and a sliding glass door to the back deck. Keep in mind the formal dining room

  Lisa Hilliard Litchfield Hills Real Estate

  73 Norfolk Rd, Winsted, CT 06098
• 

  $639,000 Sold Jul 31, 2025

  • 2,692 Sq Ft
  • $237/SF
  • 49 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2004

  102 Hollow Hill Rd, Winsted, 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 2.78 bucolic acres surrounded by nature & mature trees. Lovingly maintained, this home provides the perfect set up for stress free living & entertaining boasting a large eat in kitchen with center island, dining area, SS appliances, dual wall ovens and propane cooktop, French

  Dawn Rousseau Showcase Realty, Inc.

  102 Hollow Hill Rd, Winsted, CT 06098
• 

  Est $259,120 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,472 Sq Ft

  9 Fruit St, Winsted, CT 06098

  9 Fruit St, Winsted, CT 06098
• 

  

  /34

  $285,000 Pending

  • 2 Beds
  • 1 Bath
  • 1,880 Sq Ft

  101 Norfolk Rd, Winsted, CT 06098

  Beautifully updated Raised- Ranch retreat on 1.33 wooded acres! Nestled in a serene, natural setting yet conveniently close to local amenities. When you enter the home you will find two generous sized rooms with new vinyl plank flooring, fresh paint & a mini split as well as a spacious storage/utility room with laundry. The main floor includes the living room with a stone accent wall & great

  Jackie Desmarais Showcase Realty, Inc.

  101 Norfolk Rd, Winsted, CT 06098
• 

  $410,000 Sold Jul 31, 2025

  • 2,105 Sq Ft
  • $195/SF
  • 39 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1938

  17 Woodland Ave, Winsted, CT 06098

  Beautiful 3 bedroom updated colonial walking distance to Highland lake beach.Large eat in kitchen with granite counter tops,center island,bar area ,spacious sitting area with antique cooking stove that burns wood creates good heat.Living room with hardwood floors,fireplace and built ins.Nice patio off kitchen,yard is landscaped with fountains.2 car garage.This home is in great condition and wont

  Vincent DeVico Showcase Realty, Inc.

  17 Woodland Ave, Winsted, CT 06098
• 

  Est $342,967 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,560 Sq Ft

  202 Old New Hartford Rd, Winsted, CT 06098

  202 Old New Hartford Rd, Winsted, CT 06098
• 

  

  /28

  $225,000 Pending

  • 4 Beds
  • 2 Baths
  • 2,299 Sq Ft

  30 Rock St, Winsted, CT 06098

  Charming 2-family home offering 2,299 sq ft of living space in Litchfield County. Featuring a total of 4 bedrooms and 2 full bathrooms, this property sits on a manageable 0.18-acre lot within the Winchester School District. Great opportunity for owner-occupants or investors alike with spacious layouts and income potential.

  Patrick Precourt Dorrance Realty

  30 Rock St, Winsted, CT 06098
• 

  $799,900 Sold Jul 28, 2025

  • 3,427 Sq Ft
  • $233/SF
  • 66 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1792

  139 Bunnell St, Colebrook, CT 06021

  Wonderful Old Colonial Farmhouse on 30+ Scenic Acres! Charming and full of character, this beautiful old farmhouse offers a rare blend of original features and modern updates. The heart of the home is an updated kitchen that blends seamlessly with the historic charm. Enjoy cozy evenings by the brick fireplaces in both the family room, bedroom and the living room, each adding warmth and timeless

  Mitzi Muller William Raveis Real Estate

  139 Bunnell St, Colebrook, CT 06021
• 

  Est $458,112 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,184 Sq Ft

  123 Skinner Rd, Winsted, CT 06098

  123 Skinner Rd, Winsted, CT 06098
• 

  

  /21

  $150,000 Pending

  • 1 Bed
  • 1 Bath
  • 635 Sq Ft

  38 Riveredge Dr Unit 38, Winsted, CT 06098

  End Unit Ranch-Style Condo - Winchester. Discover privacy and convenience in this well-maintained one-level end unit nestled in the foothills of the Berkshire Mountains. Offering an open-concept layout, this ranch-style condo features a spacious living room, dining area, kitchen, large bedroom, full bathroom with in-unit laundry, & excellent closet space. While the condo would benefit from

  Suzie Larson Turning Point Realty, LLC

  38 Riveredge Dr Unit 38, Winsted, CT 06098
• 

  $292,000 Sold Jul 25, 2025

  • 2,225 Sq Ft
  • $131/SF
  • 42 Days On Market

  • 6 Beds
  • 2 Baths
  • Built 1890

  126 Williams Ave, Winsted, CT 06098

  Excellent investment opportunity! This fully occupied two-family home generates a steady $3,300 in monthly rental income. The property has been completely overhauled in the past few years with almost everything updated. It is located in a great neighborhood in walking distance to all the schools in town. Close to playgrounds and the library. The recently painted exterior of this classic home

  Michelle Grant Coldwell Banker Premier Real Estate

  126 Williams Ave, Winsted, CT 06098
• 

  Est $382,562 Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 2,615 Sq Ft

  161 Spencer St, Winsted, CT 06098

  161 Spencer St, Winsted, CT 06098
• 

  

  /15

  $175,000 Under Contract

  • 2 Beds
  • 1.5 Baths
  • 992 Sq Ft

  45 Riveredge Dr Unit 45, Winsted, CT 06098

  If you know the complex, you know it is a nicely secluded, pleasant place to live. The unit offers a nice private rear patio area. It is a lovely location by the Still River, yet close to town and offers easy access the region via highway and train from NYC to Waterbury. l Two-hour drive to NYC or Boston if traffic is kind. 45 minutes to Tanglewood, 40 to Hartford. The interior does not need a

  John Herman The Buyer's Representative LLC

  45 Riveredge Dr Unit 45, Winsted, CT 06098

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