Winchester, CT Homes for Sale

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  /39

  $559,999

  • 3 Beds
  • 2 Baths
  • 1,744 Sq Ft

  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

  (860) 532-1905

  144 Marshall St, Winsted, CT 06098
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  /13

  $649,900

  • 5 Beds
  • 1.5 Baths
  • 2,304 Sq Ft

  115 Old Robertsville Rd, Winsted, CT 06098

  Development Opportunity! 41.23 Acres with Historic Home & Barn - Subdivision Possible Rare chance to own a prime 41.23-acre parcel in New England with an 1800 Antique Colonial Farmhouse and classic English/New England hybrid barn. The land may be subdividable and is located near the highly desirable Riverwalk Condominiums, making it ideal for new condo development (subject to approvals). The

  Jared Tedesco Litchfield County Real Estate

  115 Old Robertsville Rd, Winsted, CT 06098
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  /40

  $589,900

  • 3 Beds
  • 2.5 Baths
  • 2,692 Sq Ft

  102 Hollow Hill Rd, Winsted, CT 06098

  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 door leading to side deck & built-in hutch

  Dawn Rousseau Showcase Realty, Inc.

  102 Hollow Hill Rd, Winsted, CT 06098
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  /40

  $889,000

  • 3 Beds
  • 3 Baths
  • 2,113 Sq Ft

  112 Shore Dr, Winsted, CT 06098

  Live like you're on vacation every day! This beautifully updated lakefront home sits directly on the water in Highland Lake's first Bay, offering a level backyard & a private dock just steps from your door. With 50+ feet of direct waterfront and a fenced, low-maintenance yard, this charming year-round home is the perfect blend of comfort, style, & lakefront living. The interior boasts an open

  Nancy Reardon Berkshire Hathaway NE Prop.

  112 Shore Dr, Winsted, CT 06098
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  /39

  $995,000

  • 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
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  /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
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  /37

  $525,000

  • 5 Beds
  • 4 Baths
  • 5,016 Sq Ft

  55 Walnut St, Winsted, CT 06098

  Timeless Victorian with Endless Possibilities.Step into a piece of history with this stunning Victorian property, a landmark in the community and home to The Maloney Funeral Home since the early 1900's. Nestled in the TCR Zone, this versatile building offers a wealth of potential. The TCR Zone allows for accessory residential uses, community centers, family day care homes, single-family

  David Sartirana Northwest CT Realty

  55 Walnut St, Winsted, CT 06098
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  /26

  $1,200,000

  • 5 Beds
  • 2.5 Baths
  • 3,307 Sq Ft

  77 Deer Hill Rd, Colebrook, CT 06021

  Enchanting Antique Dutch Colonial Estate with Carriage House and Barn. Nestled in a serene and private 51.2-acre haven, this stately home is a harmonious blend of historic charm and modern sophistication. As you traverse the meandering stone walls and explore the mix of sun-kissed meadows and whispering forests, you'll discover a world where time stands still, yet every modern convenience is at

  MICHAEL CONLOGUE William Pitt Sotheby's Int'l

  77 Deer Hill Rd, Colebrook, CT 06021
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  /19

  $285,000

  • 6 Beds
  • 2 Baths
  • 2,225 Sq Ft

  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
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  /5

  $999,000

  • Land
  • 116 Acres
  • $8,575 per Acre

  82 Riverton Rd, Colebrook, CT 06021

  Escape to Your Own 116 acres of Paradise in Colebrook, CT! Discover 116 +/- acres of picturesque land nestled along Riverton Road in the heart of scenic Colebrook, Connecticut. This extraordinary property offers a rare opportunity to own a vast expanse of rural beauty, complete with two serene ponds, winding old logging roads, and a mix of standing hardwoods and softwoods that create a lush,

  Suzie Larson Turning Point Realty, LLC

  82 Riverton Rd, Colebrook, CT 06021
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  /27

  $388,000

  • 5 Beds
  • 2 Baths
  • 2,403 Sq Ft

  409 N Main St, Winsted, CT 06098

  This versatile 2-family home would make a perfect owner occupant first floor unit with 3 bedrooms, with a 2 bedroom second floor apartment. Private entrances with separate utilities. Let your rental income help pay your mortgage. Each unit comes with formal living and dining rooms. Refinished original wide pine flooring. Large main Kitchen with lots of cabinet space which walks out to a

  Christine Hunter Hunter Real Estate, LLC

  409 N Main St, Winsted, CT 06098
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  /24

  $229,900

  • 5 Beds
  • 1.5 Baths
  • 2,310 Sq Ft

  30 Mountain Ave, Winsted, CT 06098

  Not afraid of some peeling paint or rotting wood? This is the house for you! 30 Mountain Ave with 5 beds, 1.5 baths is your opportunity to bring a vision to life. Located in a welcoming neighborhood, it offers a generous layout ready for customization and renovation. Whether you're a seasoned investor or a first-time buyer with a knack for design, this home has the bones to become something

  Derek Greene Derek Greene

  30 Mountain Ave, Winsted, CT 06098
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  /32

  $425,000 Open Sun 1PM - 3PM

  • 4 Beds
  • 2.5 Baths
  • 2,086 Sq Ft

  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
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  /30

  $335,000

  • 3 Beds
  • 1 Bath
  • 1,287 Sq Ft

  50 Manchester Heights, Winsted, CT 06098

  Charming Country Cape with Cottagecore appeal on just over an acre of land and situated on a culd-de-sac. Located off the beaten path in the quiet hills of Winchester, this storybook Cape-style home offers the perfect blend of rustic charm and modern comfort. Convenient to Route 8 and just minutes to town amenities. Enjoy the natural beauty surrounding the property while relaxing on the deck and

  Lisa Bredice William Raveis Real Estate

  50 Manchester Heights, Winsted, CT 06098
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  /34

  $319,900

  • 4 Beds
  • 1 Bath
  • 1,849 Sq Ft

  284 Gilbert Ave, Winsted, CT 06098

  Welcome to 284 Gilbert Avenue-a charming 4-bedroom Cape that combines efficient updates with inviting living spaces. Approximately 1,849 sq ft of sun-splashed interiors begin with a spacious eat-in kitchen featuring generous cabinetry, a dining area, and sliders that open to an elevated deck-perfect for grilling while enjoying the privacy of the beautifully manicured backyard. The main level also

  David Sartirana Northwest CT Realty

  284 Gilbert Ave, Winsted, CT 06098
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  /18

  $249,000

  • 2 Beds
  • 1 Bath
  • 674 Sq Ft

  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
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  /40

  $1,595,000

  • 5 Beds
  • 2 Baths
  • 3,693 Sq Ft

  424 E Wakefield Blvd, Winsted, CT 06098

  Stunning Lakehouse! Victorian charm! One of the earliest Highland Lake homes with extensive custom upgrades and quality renovation. A true lakefront sanctuary offering spacious living areas, extensive outdoor living areas and wide open lake views offering South and West exposure for incredible sunsets. Lakefront dock system with hydraulic boat lift, Recently renovated kitchen /dining with newer

  KAREN NEWTON William Pitt Sotheby's Int'l

  424 E Wakefield Blvd, Winsted, CT 06098
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  /4

  $250,000

  • Land
  • 16 Acres
  • $15,723 per Acre

  00 Chapel Rd, Winchester, CT 06098

  Look no further for A Very Private location to build your Dream Home?? On this Lot there is the Hilltop which can provide peace and solitude for your home or vacation retreat . Historical Winchester Center is deep with rich heritage and History of Winchester may be the place for you. The access to the Rear lot is though 151 Chapel Rd. property.

  Linda Ganem Borla & Associates Real Estate

  00 Chapel Rd, Winchester, CT 06098
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  /26

  $1,200,000

  • Land
  • 65 Acres
  • $18,380 per Acre

  257 Torringford St, Winchester, CT 06098

  65+ Acre Property with infrastructure and natural features. Spanning over 65 acres, this private property is accessed via a 5,000 foot driveway and features a mix of open space and wooded terrain. The land is bordered by historic stone walls on both sides, adding character and clear boundary lines. Bonus: 14x40 horse barn, ready for livestock or storage. 24x32 building on a concrete slab,

  Sabrina Janco Century 21 Bay-Mar Realty

  257 Torringford St, Winchester, CT 06098
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  /4

  $50,000

  • Land
  • 0.41 Acre
  • $121,951 per Acre

  130 Alpha Ave, Winsted, CT 06098

  Discover the Perfect Canvas for Your Dream Home in Winchester, Connecticut! This exceptional .41-acre parcel (owner reports closer to .5 ac) combines eight contiguous lots to create a prime opportunity for building your ideal residence. Nestled in the serene surroundings of the Highland Lake neighborhood, the property is lightly wooded with mature, straight-standing hardwoods and features a

  Suzie Larson Turning Point Realty, LLC

  130 Alpha Ave, Winsted, CT 06098
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  /2

  $39,900

  • Land
  • 0.92 Acre
  • $43,370 per Acre

  256 Colebrook Rd, Winchester Center, CT 06098

  Just under an acre of land and over 100 feet of road frontage available on Colebrook Road!

  Austin Brochu Sullivan Real Estate Inc

  256 Colebrook Rd, Winchester Center, CT 06098
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  /35

  $499,000

  • 3 Beds
  • 3 Baths
  • 2,747 Sq Ft

  117 South Rd, Winsted, CT 06098

  Nestled in a peaceful rural setting of Winchester Center, this charming home offers a perfect blend of rustic character and modern convenience. The property is located on over 3.3 acres of land and is adjacent to a scenic pond. Inside you will find a three bedroom two bath home with an additional in law apartment with one full bath and one bedroom and its own private entrance. The home also

  Christina Niziolek William Raveis Real Estate

  117 South Rd, Winsted, CT 06098
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  /21

  $329,000

  • 3 Beds
  • 2 Baths
  • 1,480 Sq Ft

  150 Mathew Rd, Winsted, CT 06098

  Highland Lake, 3 Bedroom, 2 Bath, well maintained home. Lake views, newer appliances, hardwood floors, move-in ready, lake rights. 6,500 watt whole house generator. 8x12 shed with power, 35 Amp out side outlet for camper, working chimney for wood stove on lower level, ASSUMABLE MORTGAGE!

  Josh Dionne Commercial Services Realty

  150 Mathew Rd, Winsted, CT 06098
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  /3

  $225,000

  • Land
  • 0.23 Acre
  • $978,261 per Acre

  129 Shore Dr, Winsted, CT 06098

  A RARE OPPORTUNITY on HIGHLAND LAKE! This approved buildable lot is ready and waiting for you to build your dream! Lake life is a great life, make it yours!

  Annie Simard LPT Realty

  129 Shore Dr, Winsted, CT 06098
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  /9

  $739,900

  • Land
  • 93 Acres
  • $7,924 per Acre

  0 Old Robertsville Rd, Winchester, CT 06098

  Nestled along a peaceful country road near the Colebrook and Barkhamsted town lines, this breathtaking 93.38-acre parcel embodies the timeless charm of rural New England. Once part of a cherished family farm, the land offers a harmonious blend of rolling meadows, majestic forests, and the gentle, winding presence of the Still River, which meanders through a substantial portion of the property.

  David Sartirana Northwest CT Realty

  0 Old Robertsville Rd, Winchester, CT 06098
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  /19

  $230,000

  • 3 Beds
  • 1.5 Baths
  • 1,200 Sq Ft

  39 Orchard St, Winsted, CT 06098

  Back on the market, buyer's financing fell through. Welcome to this beautifully updated 3-bedroom, 1.5-bath colonial in the heart of Winsted! This home seamlessly blends classic charm with modern conveniences, featuring a spacious layout, abundant natural light, and stylish updates throughout. The inviting living room offers a cozy atmosphere perfect for gatherings. The updated kitchen boasts

  Michael J Flaherty Jr Sullivan Real Estate Inc

  39 Orchard St, Winsted, CT 06098
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  /4

  $14,999

  • Land
  • 0.12 Acre
  • $124,992 per Acre

  320 White Oak Trail, Winchester, CT 06098

  Plot Of Land Valued at $32,060 Property ID #: 033 105C 044+45 Zoning: HL

  Dillon Cass eRealty Advisors, Inc.

  320 White Oak Trail, Winchester, CT 06098
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  /36

  $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
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  /2

  $49,000

  • Land
  • 0.37 Acre
  • $132,432 per Acre

  99 Hubbard St, Winsted, CT 06098

  99 Hubbard St. - Private Lot Near Downtown & Highland Lake. Tucked away at the end of a quiet dead-end street, this .37-acre lot offers both privacy and convenience. While enjoying a peaceful setting, you're still just minutes from downtown with easy access to shopping, dining, and entertainment. Plus, Highland Lake is just a short distance away, providing endless opportunities for boating,

  David Sartirana Northwest CT Realty

  99 Hubbard St, Winsted, CT 06098
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  /2

  $29,000

  • Land
  • 0.44 Acre
  • $65,909 per Acre

  124 Rockwell St, Winsted, CT 06098

  124 Rockwell St. - Versatile .44-Acre Lot Near Downtown This .44-acre lot offers a prime location close to downtown with city water and sewer available in the street. The previous home sat at street level, while the majority of the lot slopes below, creating a unique landscape with plenty of potential. With a little imagination and the right site contractor, this property presents endless

  David Sartirana Northwest CT Realty

  124 Rockwell St, Winsted, CT 06098
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  /33

  $450,000

  • 4 Beds
  • 1.5 Baths
  • 2,239 Sq Ft

  51 Pratt St, Winsted, CT 06098

  Welcome to this beautifully renovated home, nicely tucked away in historic Winsted. This lovely property features over 2,200 square feet of gross interior living space. The large kitchen, dining, and living room areas provide a seamless flow, perfect for entertaining. The home boasts four spacious bedrooms and one and a half baths. The beautifully renovated attic adds even more charm and

  Lourdes Galvan-Dominguez Coldwell Banker Realty

  51 Pratt St, Winsted, CT 06098
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  /39

  $950,000

  • 14 Beds
  • 7 Baths
  • 4,860 Sq Ft

  175 N Main St, Winsted, CT 06098

  Addresses include 175 Main Street and 183 Main Street in Winsted, CT. Amazing opportunity to acquire a 9 Unit Asset (7 Apartments + 2 Retail) in Winsted with anchor tenant Noli's Restaurant (Rent $2,266 w 3% increase/year) w over 20 years in business! Pride of Ownership is evident with Capital Improvements made by the current owners, including: new water heaters, heating zones, electrical

  Ryan Rea Berkshire Hathaway NE Prop.

  175 N Main St, Winsted, CT 06098
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  /40

  $1,699,500

  • 4 Beds
  • 3 Baths
  • 2,496 Sq Ft

  538 Wheelers Point, Winsted, CT 06098

  Lakefront Historic Architecture meets Modern Styling on private waterfront penninsula with 360' direct lake frontage! Split timber tudor architecture offers unique features - leaded glass, stone flooring, window seats, paneling and mouldings, brick and stone appointments. A stunning kitchen for folks who cook, charming diningroom with bar and window seat overlooking the waterfront, and spacious

  KAREN NEWTON William Pitt Sotheby's Int'l

  538 Wheelers Point, Winsted, CT 06098
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  /40

  $1,400,000

  • 8 Beds
  • 4.5 Baths
  • 5,231 Sq Ft

  435 W Wakefield Blvd, Winsted, CT 06098

  Welcome to this spectacular Highland Lake estate, offering a unique blend of luxury & tranquility. Situated on 1.3 acres of level land, the property includes a large barn/garage capable of housing multiple cars, boats, & equipment. The main home boasts generously sized rooms w/ high ceilings, offering an open, airy feel throughout. The kitchen has been updated w/ hardwood cabinets, featuring

  Heidi Picard-Ramsay Berkshire Hathaway NE Prop.

  435 W Wakefield Blvd, Winsted, CT 06098
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  /40

  $2,600,000

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

  431 W Wakefield Blvd, Winsted, CT 06098

  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 boating, jet skiing, swimming, and fishing right from your private dock, or simply unwind along the shoreline. As winter

  Lisa Ogren Berkshire Hathaway NE Prop.

  431 W Wakefield Blvd, Winsted, CT 06098
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  /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
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  /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
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  /2

  $69,000

  • Land
  • 2.00 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
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  /2

  $749,900

  • 7 Beds
  • 3 Baths
  • 3,486 Sq Ft

  39 S Main St, Winsted, CT 06098

  THREE PROPERTIES ONE PRICE!!! Includes single family, multi family & additional lot totaling 4.36 acres. 1. 3500 sq ft 2 family home featuring 1800's architecture including massive period correct windows, wrap around porch, beautiful stone foundation, and detached 2 car garage. 5 bed, 2 1/2 bath main house with 2 bed, 1 bath attic apartment, freshly updated. Brand new whole house natural gas

  RYAN HORVAY Smith & DeGroat Real Estate

  39 S Main St, Winsted, CT 06098
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  /2

  $23,900

  • Land
  • 0.15 Acre
  • $159,333 per Acre

  48 Bridge St, Winsted, CT 06098

  Nestled just steps from downtown, this .15-acre lot offers a fantastic opportunity in a highly convenient location. The property is fairly level and provides easy access to shopping, restaurants, The Gilson Theater, and Little Red Barn Brewery. With city water and sewer available, this lot is ready for your vision. Whether you're looking to build or invest, this prime spot puts you right in the

  David Sartirana Northwest CT Realty

  48 Bridge St, Winsted, CT 06098

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