Newest Homes for Sale in Winchester, CT

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  /11

  $190,000

  • 2 Beds
  • 1.5 Baths
  • 832 Sq Ft

  8 Oak St, Winsted, CT 06098

  Discover a low maintenance and hassle-free alternative to condo living with this easy-to-maintain, single-family home , perfect for investors, first-time buyers, or anyone seeking simplified living without the burden of HOA fees. Step inside to an efficient layout featuring brand-new WREN kitchen cabinets, granite countertops, a new gas stove, and a new refrigerator, offering a fresh and modern

  Austin Brochu Sullivan Real Estate Inc

  8 Oak St, Winsted, CT 06098
• Explore Winchester

• 

  

  

  /24

  $375,000

  • 3 Beds
  • 2.5 Baths
  • 2,356 Sq Ft

  95 Nalette Dr, Winsted, CT 06098

  Stunning Contemporary Home on a Quiet Corner Lot This unique contemporary-style home offers a beautifully updated open floor plan that seamlessly blends the kitchen, dining, and living areas-perfect for modern living and entertaining. The kitchen features granite countertops, ample cabinetry, and great flow into the main living space. The first floor includes a refinished half bathroom and an

  Jennifer Mitchell Northwest CT Realty

  95 Nalette Dr, Winsted, CT 06098
• 

  

  

  /16

  $290,000

  • 3 Beds
  • 2 Baths
  • 1,652 Sq Ft

  118 Meadow St, Winsted, CT 06098

  This charming historic home, built in 1860, blends timeless character with thoughtful updates. Featuring 3-4 bedrooms, this property offers flexible living space to meet your needs. The beautifully remodeled upstairs bathroom is a standout feature, offering modern comfort within this classic home. Enjoy your LARGE eat-in kitchen with laundry hook ups and plenty of natural lighting. The home sits

  Ashley Henry The Washington Agency

  118 Meadow St, Winsted, CT 06098
• 

  

  

  /38

  $395,000

  • 3 Beds
  • 1.5 Baths
  • 1,909 Sq Ft

  720 Main St, Winsted, CT 06098

  Prime Mixed-Use Opportunity in Downtown Winsted! High-visibility two-story building located on bustling Main Street, most recently home to "JT's Cafe," and previously known as "The Winning Ticket Cafe." The first-floor commercial space includes features such as an existing kitchen area with oven range vents, fridge, bathroom, and open seating area. Great potential for a new restaurant, cafe,

  Ryan Marconi The Washington Agency

  720 Main St, Winsted, CT 06098
• 

  

  

  /40

  $429,000

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

  187 Torringford St, Winsted, CT 06098

  Welcome to 187 Torringford Rd! Set on a beautiful 4-acre lot, this spacious 4-bedroom home offers the perfect blend of natural light, character, and country living. Step inside through the mudroom, also serving as a convenient laundry area, and head up to a charming loft that overlooks the bright, window filled kitchen. The kitchen features an abundance of natural light and provides a warm,

  Jessica Washington William Raveis Real Estate

  187 Torringford St, Winsted, CT 06098
• 

  

  /35

  $339,900

  • 4 Beds
  • 2 Baths
  • 1,999 Sq Ft

  148 Danbury Quarter Rd, Winchester, CT 06098

  Welcome to this Wonderful Historic Colonial Farmhouse.. This home has been lovingly remodeled with many of the original features still intact. This home offers a large kitchen with newer counters open to the dining area and is complete with a fireplace. Living room is generous sized, it's filled with light, exposed beams and hardwood floor. On this level you'll also find 2 bedrooms and a fully

  Susan MCGHEE The Washington Agency

  148 Danbury Quarter Rd, Winchester, CT 06098
• 

  

  /12

  $750,000

  • 4 Beds
  • 2 Baths
  • 5,389 Sq Ft

  436 Main St, Winsted, CT 06098

  One-of-a-Kind opportunity with 4 apartments plus a turnkey, award-winning restaurant in the heart of Litchfield County, perfectly situated in a high-traffic location. The well-established business offers 2,177 sq. ft. of warm, inviting atmosphere with 65 indoor seats and 35 outdoor seats-ideal for both casual dining and special occasions. Has a cafe license (liquor) but no bar. With a 10-year

  Tony Goia The Washington Agency

  436 Main St, Winsted, CT 06098
• 

  

  /21

  $299,900

  • 2 Beds
  • 1 Bath
  • 702 Sq Ft

  156 Lincoln Ave, Winsted, CT 06098

  Welcome to your cozy cottage retreat in beautiful Highland Lake Community. Views of the lake from deck, public beach right around the corner. Step inside to a large mudroom, open living room, updated kitchen, 2 bedrooms, 1 full bath & laundry all on one level. New flooring and paint throughout. New roof, HW heater only 4 years old, vinyl siding, large yard with fire pit and shed. Year round lake

  Mary Mary LeBlanc Realty

  156 Lincoln Ave, Winsted, CT 06098
• 

  

  /36

  $499,000

  • 3 Beds
  • 2 Baths
  • 2,167 Sq Ft

  197 Spencer Hill Rd, Winsted, CT 06098

  Discover the charm of this spacious contemporary Cape, set on a peaceful one-acre lot in a desirable rural neighborhood. Offering over 3,000 square feet of living space, this well-maintained home provides a flexible layout ideal for today's lifestyle. The main level features a formal living room, dining room, updated kitchen, den, sunroom with fireplace and hot tub, full bath, and convenient

  

  David Sartirana

  Northwest CT Realty

  (860) 419-0914

  197 Spencer Hill Rd, Winsted, CT 06098
• 

  

  /37

  $500,000

  • 4 Beds
  • 2.5 Baths
  • 3,416 Sq Ft

  440 Platt Hill Rd, Winsted, CT 06098

  Distinctive Country Estate with Two Homes on 9.6 Rolling Acres Set amid 9.6 picturesque country acres, this unique property offers two homes and endless potential. The stone and stucco main residence features eight spacious rooms, including four bedrooms and four fireplaces, blending classic character with old-world charm. Rolling open land and mature trees surround the home, providing an ideal

  David D'Amore Northwest CT Realty

  440 Platt Hill Rd, Winsted, CT 06098
• 

  /2

  $29,000

  • Land
  • 1.88 Acres
  • $15,426 per Acre

  52 White St, Winsted, CT 06098

  Discover the possibilities with this 1.8-acre parcel located on a peaceful in-town street. The property offers a convenient location close to town amenities while maintaining a quiet, private setting. Public water and sewer are available in the street, though not currently connected to the property. While the land is developable, the seller will retain easements for drainage and access to

  

  David Sartirana

  Northwest CT Realty

  (860) 856-5386

  52 White St, Winsted, CT 06098
• 

  

  /21

  $879,990

  • Land
  • 131.5 Acres
  • $6,692 per Acre

  000000 Norfolk Rd, Winchester, CT 06098

  Rare Multi-Parcel Land Opportunity - 5 Parcels, Endless Possibilities Discover this exceptional assemblage of five contiguous parcels spanning the scenic towns of Winchester and Colebrook in Connecticut's pristine Litchfield County. This remarkable offering combines the best of both worlds with a captivating mixture of open fields and mature forest, creating a diverse landscape that's as

  John Harney William Pitt Sotheby's Int'l

  000000 Norfolk Rd, Winchester, 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
• 

  

  /22

  $179,900

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

  111 Riverton Rd Unit 90, Winsted, CT 06098

  Discover the ease of condo living with the charm of a riverside retreat at Riverwalk Condos. This beautifully cared-for 2-bedroom, 1.5-bath home offers an inviting layout designed for comfort and relaxation. The spacious living room with its warm fireplace opens to a private deck overlooking the Still River-an ideal spot to unwind at the end of the day or entertain with a view. The kitchen also

  

  David Sartirana

  Northwest CT Realty

  (860) 615-2545

  111 Riverton Rd Unit 90, Winsted, CT 06098
• 

  

  /22

  $499,000

  • 3 Beds
  • 2 Baths
  • 2,186 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

  Dani Dorman Real Broker CT, LLC

  11 Old Creamery Rd, Colebrook, CT 06021
• 

  

  /8

  $389,000

  • Land
  • 20.87 Acres
  • $18,639 per Acre

  7 Stadler Heights, Winsted, CT 06098

  Welcome, You be the first, to come and conquer this land here in Winchester, Connecticut. There are 20.87 acres of virgin land. Come and build, do what you do best, you can have Peace and Privacy!!! There are no sidewalks, no streets that drive through. You are 40 minutes from multiple private schools. 16 minutes from Charlotte Hungerford Hospital. 1 hour from Tweed Airport New Haven. 39

  Hector Ortiz KW Legacy Partners

  7 Stadler Heights, Winsted, CT 06098
• 

  

  /27

  $394,900

  • 2 Beds
  • 1.5 Baths
  • 1,440 Sq Ft

  212 Spencer Hill Rd, Winsted, CT 06098

  Welcome to your peaceful retreat in the heart of Winchester - a quiet, scenic town surrounded by natural beauty. Tucked away on a private lot, this thoughtfully maintained home offers a perfect blend of rustic charm and modern comfort, with every detail designed to enhance your connection to the outdoors. Step inside to discover gleaming original hardwood floors that stretch across the sun-filled

  

  Tammy Powling

  Coldwell Banker Realty

  (860) 743-1453

  212 Spencer Hill Rd, Winsted, CT 06098
• 

  

  /40

  $749,999

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

  151 Losaw Rd, Winsted, CT 06098

  This property is your personal sanctuary, complete with private trails for hiking your own land. Feel worlds away while being less than 2 miles to town amenities in this like-new retreat nestled on an expansive 11.59-acre lot. The eat-in-kitchen is well-equipped with ample cooking space, seamlessly connected to the formal dining room and open to living space, and leads out to the large deck with

  Breanna Goebel Compass Connecticut, LLC

  151 Losaw Rd, Winsted, CT 06098
• 

  

  /7

  $259,000

  • 3 Beds
  • 1 Bath
  • 1,488 Sq Ft

  312 Colebrook River Rd, Colebrook, CT 06021

  Charming Colonial on a 2-acre lot. Inside, you'll find an updated kitchen featuring granite countertops and newer appliances. The large, sunny family room on the first floor is filled with natural light, creating a warm and inviting atmosphere. A combined living and dining room with a cozy wood stove adds charm and functionality to the main level. Recent upgrades to the home include a new roof in

  

  Amanda Balaski

  Northwest CT Realty

  (860) 891-2072

  312 Colebrook River Rd, Colebrook, CT 06021
• 

  

  /40

  $1,149,000

  • 3 Beds
  • 3 Baths
  • 2,097 Sq Ft

  674 E Wakefield Blvd, Winsted, CT 06098

  Experience premier waterfront living on Highland Lake in this beautifully maintained 3-bedroom, 3-bath home offering stunning panoramic lake views and direct water access. Situated in the desirable 3rd Bay, this property boasts a private dock-perfect for boating, swimming, and enjoying all the lake lifestyle has to offer. Inside, you'll find an open and inviting layout with a spacious living

  Patrick Smith Smith & DeGroat Real Estate

  674 E Wakefield Blvd, Winsted, CT 06098
• 

  

  /34

  $599,900

  • 5 Beds
  • 3 Baths
  • 3,404 Sq Ft

  441 Platt Hill Rd, Winsted, CT 06098

  Welcome to 441 Platt Hill Road - a home that offers warmth, charm, and plenty of space to make memories. This inviting residence features an open and airy layout filled with natural light thanks to large windows and multiple skylights. Solid hardwood floors and tile run throughout the main level, creating a timeless foundation for your personal touch. The spacious eat-in kitchen, while vintage in

  

  David Sartirana

  Northwest CT Realty

  (860) 773-4065

  441 Platt Hill Rd, Winsted, CT 06098
• 

  

  /27

  $399,000

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

  51 Pratt St, Winsted, CT 06098

  This stunning Renovated home is perfectly situated in the beautiful town of Winsted could be yours! Just a leisurely walk from the beautiful Highland Lake. Offering more than 2,200 square feet of thoughtfully designed living space, this home blends timeless charm with modern updates. The bright and spacious kitchen opens effortlessly into a welcoming dining area and a cozy yet expansive living

  Arlene Gonzalez The Gonzalez Property Group

  51 Pratt St, Winsted, CT 06098
• 

  

  /27

  $375,000

  • 3 Beds
  • 3,660 Sq Ft

  57 Main St, Winsted, CT 06098

  Wonderful multiuse property on Main St. in Winsted. Currently used as a cleaners on the first floor and residential unit on the second floor. Multiple possibilities for this building which is in a prime location. Potential to take over the current business and rent or live in second floor, covert to multifamily or start a new business venture. This property is also listed as commercial with MLS

  Stacy LaQuerre Regall Realty, LLC

  57 Main St, Winsted, CT 06098
• 

  

  /25

  $184,900

  • 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
• 

  

  /38

  $1,270,000

  • 3 Beds
  • 3 Baths
  • 2,420 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
• 

  

  /13

  $649,900

  • Land
  • 41.23 Acres
  • $15,763 per Acre

  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 home

  Jared Tedesco Litchfield County Real Estate

  115 Old Robertsville Rd, Winsted, CT 06098
• 

  

  /9

  $850,000

  • Land
  • 116.5 Acres
  • $7,296 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
• 

  /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
• 

  

  /5

  $300,000

  • Land
  • 15.9 Acres
  • $18,868 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
• 

  

  /26

  $1,200,000

  • Land
  • 65.29 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
• 

  /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
• 

  

  /39

  $920,000

  • 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
• 

  

  /5

  $1,350,000

  • Land
  • 124.92 Acres
  • $10,807 per Acre

  0 Winsted Norfolk Rd Unit 24089254, Colebrook, CT 06021

  Intriguing Litchfield County / Colebrook CT Location: Great Opportunity to Own this Surveyed 124.92 Acre Site. Excellent Visible Corner Location. Lightly Wooded with Good Road Frontage. Potential as a Commercial / Residential Development, Private Estate Style Compound, Agricultural Use. Put your imagination to work here. Includes an existing Golf Driving Range at the Corner of Route 44

  Marshall Cohen Cohen Agency

  0 Winsted Norfolk Rd Unit 24089254, Colebrook, CT 06021
• 

  

  /34

  $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
• 

  

  /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
• 

  

  /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
• 

  /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

  (860) 891-6121

  124 Rockwell St, Winsted, CT 06098
• 

  /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

  (860) 946-4468

  99 Hubbard St, Winsted, CT 06098
• 

  /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

  (860) 453-5624

  48 Bridge St, Winsted, CT 06098
• 

  

  /37

  $499,999

  • 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

  (860) 390-5071

  55 Walnut St, Winsted, CT 06098

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