Winchester, CT Homes for Sale

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  /16

  $389,900

  $10K PRICE DROP

  • 4 Beds
  • 1.5 Baths
  • 1,944 Sq Ft

  122 Standard Ave, Winsted, CT 06098

  Welcome home to this well-maintained 4-bedroom Colonial tucked away on a quiet dead-end street. The newly renovated eat-in kitchen features updated cabinetry, countertops, and finishes, creating a great space for everyday living and gathering. The spacious living room and dining area offer plenty of room to make the home your own, while four bedrooms provide flexibility for family, guests, or a

  

  Amanda Balaski

  Northwest CT Realty

  122 Standard Ave, Winsted, CT 06098
• Explore Winchester

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  /39

  $1,550,000

  Open Sat 1PM - 3PM $50K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,129 Sq Ft

  752 Lake Dr, Winsted, CT 06098

  Experience the best of lakefront living with breathtaking views, spectacular sunsets, and exceptional outdoor spaces. This amazing waterfront home features a brand-new 100' x 14' Brazilian hardwood deck, a 35' x 6' stationary Trex and steel dock, and a private cabana-perfect for relaxing, boating, swimming, and entertaining. Soak in panoramic water views from multiple vantage points, including

  

  Pam Famiglietti

  William Raveis Real Estate

  752 Lake Dr, Winsted, CT 06098
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  /36

  $189,000

  $10K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,154 Sq Ft

  192 Ledge Dr Unit 192, Torrington, CT 06790

  Bright and spacious 2 bedroom, 2 full bathroom townhouse. This Hideaway model in the highly desirable Lakeridge complex features a main level with a bedroom, a full bathroom with custom tile shower and glass doors, a laundry area, living/dining room and a fully-equipped kitchen. The large living room with vaulted ceiling and floor to ceiling accent wall surrounding the fireplace create a

  

  Alexa Skalandunas

  William Raveis Real Estate

  192 Ledge Dr Unit 192, Torrington, CT 06790
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  /37

  $250,000

  • Land
  • 9 Acres
  • $27,778 per Acre

  321 Colebrook Rd, Winchester, CT 06098

  321 Colebrook Road is a rare opportunity to own beautiful land with natural features and self-sustaining potential. A natural spring gently rolls through the property, surrounded by mature oak, ash, birch, black walnut, pine, and abundant sugar maple trees - perfect for producing your own maple syrup. The land is rich with native granite and sparkling quartz throughout, adding character and

  

  Ariel Edery

  mygoodagent

  321 Colebrook Rd, Winchester, CT 06098
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  /10

  $350,000

  • 4 Beds
  • 2 Baths
  • 2,914 Sq Ft

  100 Norfolk Rd, Winsted, CT 06098

  3.7-acre property offering a 4-bedroom, 2-bath Cape with plenty of room and flexibility. Formerly operated as a small farm, the property provides space for gardening, animals, recreation, or other uses. The first floor features an open floor plan with impressive 10-foot ceilings and a layout that can adapt to a variety of needs. Four bedrooms provide room for family, guests, or a home office. A

  

  Amanda Balaski

  Northwest CT Realty

  100 Norfolk Rd, Winsted, CT 06098
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  /3

  $359,900

  • 4 Beds
  • 2 Baths
  • 2,699 Sq Ft

  77 Hubbard St, Winsted, CT 06098

  Discover this versatile two-family residence offering a blend of modern updates and timeless charm. Each unit boasts three bedrooms and a full bath, providing ample space and comfort for tenants or multi-generational living. Both units have been beautifully renovated, featuring a brand-new kitchen with stylish finishes, updated bath, gleaming hardwood floors, and plush new carpet in the bedrooms.

  

  Amy Rio

  Better Homes and Gardens Real Estate Executive Real Estate

  77 Hubbard St, Winsted, CT 06098
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  /35

  $305,000

  $35K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,442 Sq Ft

  103 Cordano Rd, Winsted, CT 06098

  Back on the market due to buyers inability to secure financing. Well-maintained Cape in a desirable rural setting, yet just minutes from shopping, dining, schools, and other everyday conveniences. This 7-room home offers 3 bedrooms and 1.5 baths with a flexible floor plan designed for comfortable living. The main level features a formal living room, dining room, kitchen, family room, primary

  

  David Sartirana

  Northwest CT Realty

  103 Cordano Rd, Winsted, CT 06098
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  /37

  $410,000

  $140K PRICE DROP

  • 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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  /2

  $45,000

  • Land
  • 17,859 Sq Ft
  • $109,756 per Acre

  32 Hubbard St, Winsted, CT 06098

  Rare opportunity to build in a convenient in-town location! This level 0.41-acre lot is ideally situated close to downtown amenities while offering easy access to Highland Lake's public beach and boat launch. Formerly improved with a three-story Colonial home, the property presents a unique opportunity to redevelop an established homesite. Public water, public sewer, and natural gas are available

  

  David Sartirana

  Northwest CT Realty

  32 Hubbard St, Winsted, CT 06098
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  /28

  $324,900

  $45K PRICE DROP

  • 4 Beds
  • 1.5 Baths
  • 2,722 Sq Ft

  70 Walnut St, Winsted, CT 06098

  Step back in time and experience the timeless elegance of this spacious 2,722 sq. ft. Victorian offering 10 rooms, 5 bedrooms, and 1.5 baths. Rich in original character and architectural detail, this classic home showcases beautiful hardwood floors, impressive natural woodwork, pocket doors, built-ins, decorative moldings, and stunning stained-glass accents that capture the craftsmanship of a

  

  David Sartirana

  Northwest CT Realty

  70 Walnut St, Winsted, CT 06098
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  /40

  $629,900

  • 3 Beds
  • 1.5 Baths
  • 1,168 Sq Ft

  837 E Wakefield Blvd, Winsted, CT 06098

  Enjoy the best of Highland Lake living with this unique property offering a spacious home directly across the street from the lake along with your own separate waterfront parcel! The main house features 7 rooms, 3-4 bedrooms and 2 full baths, providing plenty of space for year-round living or a relaxing lake retreat. A deck overlooking the waterfront offers the perfect spot to enjoy the lake

  

  David Sartirana

  Northwest CT Realty

  837 E Wakefield Blvd, Winsted, CT 06098
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  /40

  $749,900

  Open Sat 11AM - 1PM

  • 3 Beds
  • 2 Baths
  • 1,131 Sq Ft

  180 Shore Dr, Winsted, CT 06098

  Highest and best offer by noon on Monday 21st. Welcome to 180 Shore Dr - your own beautifully renovated waterfront retreat on highly desirable Lake! This exceptional year-round home offers the perfect combination of modern comfort, stunning water views, and the lake lifestyle you've been dreaming about. Featuring 3 bedrooms and 2 full bathrooms, the home has been extensively remodeled with

  

  Jacek Mikolajczyk

  Berkshire Hathaway NE Prop.

  180 Shore Dr, Winsted, CT 06098
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  /7

  $325,000

  • 4 Beds
  • 2.5 Baths
  • 2,257 Sq Ft

  48 Center St, Winsted, CT 06098

  Investment Opportunity! Well-maintained two-family house offering the ideal combination of functionality and income potential. Each unit features 5 rooms, including 2 bedrooms and 1 full bath. Enjoy the benefits of a convenient downtown location, close to schools, shopping, dining, and everyday conveniences. Both units are currently rented, making this property a strong choice for investors

  

  Amanda Balaski

  Northwest CT Realty

  48 Center St, Winsted, CT 06098
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  /7

  $299,900

  • 5 Beds
  • 2 Baths
  • 2,016 Sq Ft

  18 Pratt St, Winsted, CT 06098

  Well-maintained two-family home offering excellent owner-occupant or investment potential. First-floor unit features 3 bedrooms, kitchen, and living room and is currently rented. Second-floor unit is vacant and offers 2 bedrooms, living room, and kitchen. Separate utilities and laundry for each unit. Full basement provides additional storage. Entire home has undergone lead remediation. Great

  

  Amanda Balaski

  Northwest CT Realty

  18 Pratt St, Winsted, CT 06098
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  /5

  $37,900

  $32K PRICE DROP

  • Land
  • 5,227 Sq Ft
  • $315,833 per Acre

  319 White Oak Trail, Winchester, CT 06098

  Wooded interior lot located at the end of a dead-end street, offering a private setting. The parcel is slightly sloped and accessed from the end of the road. Clients, do your homework , including but not limited to surveys, zoning, and building approvals. Convenient location with approximately a 15-minute walk to Resha Beach on Highland Lake for recreational enjoyment. Lake rights are granted to

  Matt Tearman Coldwell Banker Realty

  319 White Oak Trail, Winchester, CT 06098
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  /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
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  /28

  $629,000

  • 8 Beds
  • 4.5 Baths
  • 4,800 Sq Ft

  143 Holabird Ave, Winsted, CT 06098

  One of the finest grand classic Colonial homes where timeless charm and beautiful details can still be found throughout. Features include elegant crown molding, rich wood paneling, wide baseboard molding, gleaming hardwood floors, and a sweeping grand staircase-all adding to the warmth and character of this truly special home. This home features formal dining room, sitting room with fireplace,

  Linda Ganem Borla & Associates Real Estate

  143 Holabird Ave, Winsted, CT 06098
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  /8

  $499,900

  • 6 Beds
  • 5 Baths
  • 2,864 Sq Ft

  205 Old New Hartford Rd, Winchester, CT 06098

  Charming Multi-Family Property with steady income potential! Welcome to your next lucrative investment venture! Nestled on an expansive 1-acre lot, this multi-family property features 5 distinct living spaces, making it an ideal addition to your real estate portfolio. This property comprises 4 studio apartments and a spacious 2-bedroom apartment, catering to a variety of tenants and maximizing

  TK Krumm Berkshire Hathaway NE Prop.

  205 Old New Hartford Rd, Winchester, CT 06098
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  /38

  $649,900

  • 2 Beds
  • 1 Bath
  • 1,361 Sq Ft

  600 E Wakefield Blvd, Winsted, CT 06098

  Nestled along the coveted east shore of Highland Lake, 600 East Wakefield Boulevard presents a rare opportunity to own a piece of one of Connecticut's most sought-after waterfront communities. Filled with charm and character, this lakeside property offers the perfect canvas to create a custom retreat that reflects your vision and lifestyle. Spend your days swimming, boating, kayaking, and

  Stacy Anselmo Coldwell Banker Realty

  600 E Wakefield Blvd, Winsted, CT 06098
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  /39

  $309,900

  • 2 Beds
  • 2 Baths
  • 1,346 Sq Ft

  94 Colony Dr, Winsted, CT 06098

  Welcome home to this beautifully maintained 2bedroom Cape offering the perfect blend of comfort, character, and modern updates. Set in a soughtafter neighborhood, this property delivers movein readiness with valuable improvements already completed. (New roof and electric panel). Step inside to find a bright, inviting living space featuring wood floors, updated kitchen, a cozy fireplace, and

  Debra Stewart Integrity Real Estate

  94 Colony Dr, Winsted, CT 06098
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  /30

  $260,000

  Open Sat 10AM - 12PM

  • 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 and ample

  Ashley Henry The Washington Agency

  118 Meadow St, Winsted, CT 06098
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  /29

  $489,000

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft

  50 Palmer Ave, Winsted, CT 06098

  Originally built in 1940, this charming Cape has been completely transformed-taken down to the studs and thoughtfully renovated from top to bottom, blending classic character with the comfort and style of a modern home. The inviting open floor plan features a gorgeous kitchen with a large center island, granite countertops and stainless-steel appliances, flowing seamlessly into the spacious

  Jennifer Roller Berkshire Hathaway NE Prop.

  50 Palmer Ave, Winsted, CT 06098
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  /15

  $799,000

  $60K PRICE DROP

  • Land
  • 65.29 Acres
  • $12,238 per Acre

  257-259 Torringford St, Winchester, CT 06098

  Uncover this hidden gem - 65.29 pristine acres of raw land, with natural beauty and endless potential. This picturesque parcel features serene ponds and mature trees. Distant views and incredible sunsets can be enjoyed from the property. Much site work has been done to date. A driveway with a binder course is already in place offering easy access into and throughout the property. Many acres have

  Lisa Toczko Home Valley Realty, LLC

  257-259 Torringford St, Winchester, CT 06098
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  /29

  $199,000

  • 3 Beds
  • 1 Bath
  • 1,056 Sq Ft

  416 Horne Ave, Winsted, CT 06098

  Welcome to 416 Horne Ave, a charming 3-bedroom, 1-bath home offering approximately 1,056 square feet of comfortable living space in Winsted. Built in 1979 and situated on approximately 0.29 acres, this property offers a practical layout with room to make it your own. The home provides a welcoming setting for everyday living, with three bedrooms offering flexibility for family, guests, a home

  Thomas Mele Social & Co Realty

  416 Horne Ave, Winsted, CT 06098
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  /8

  $449,000

  Open House 9/27 Coming Soon

  • 3 Beds
  • 2.5 Baths
  • 1,659 Sq Ft

  150 E Lake St, Winsted, CT 06098

  Enjoy lake living with this inviting 3 bedroom, two and a half bath home located directly across the street from Highland Lake. Offering water views and a convenient location, this property is a wonderful opportunity for a year round residence or weekend getaway. The home features a two car garage and plenty of parking and storage. Enjoy the convenience of having two beaches and a boat launch

  Austin Brochu Sullivan Real Estate Inc

  150 E Lake St, Winsted, CT 06098
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  /6

  $386,000

  • Land
  • 1.91 Acres
  • $202,094 per Acre

  00 Main St, Winsted, CT 06098

  Exceptional 2+ Acre Development Opportunity - Route 44, Winsted, CT** Rare opportunity to acquire approximately 2+- acres with nearly 700 feet of frontage on Main Street (Route 44), one of Winsted's primary commercial corridors. Located within the Town Gateway Zone, this highly visible parcel offers outstanding flexibility for a variety of development opportunities, including commercial,

  Dan Merrigan Merrigan & Lefebvre Realty

  00 Main St, Winsted, CT 06098
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  /6

  $525,000

  $270K PRICE DROP

  • Land
  • 10,018 Sq Ft
  • $2,282,609 per Acre

  535,538 W Wakefield Blvd, Winchester, CT 06098

  This waterfront property is ideal for contractors or individuals who want to build a year-round home on Highland Lake's West side. The property is being sold as a package (3 lots have been approved for construction, parking, and a well ). The lots consist of .10 acres across the street from the water and .023 acres on the water.

  chris marino Cohen Agency

  535,538 W Wakefield Blvd, Winchester, CT 06098
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  /30

  $450,000

  • 3 Beds
  • 2 Baths
  • 1,430 Sq Ft

  130 Riverton Rd, Winsted, CT 06098

  Bring your horses home! There's something special about country living-stepping outside with your coffee, seeing your horses grazing, hearing the chickens scratching around, and having a little more room to simply enjoy life. 130 Riverton Road offers the space and setting to create the country lifestyle you've been hoping of. A two-stall run-in shed is already in place for your horses, with

  Kelly Ryan William Raveis Real Estate

  130 Riverton Rd, Winsted, CT 06098
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  /39

  $289,000

  • 2 Beds
  • 1 Bath
  • 596 Sq Ft

  347 W Wakefield Blvd, Winsted, CT 06098

  Welcome to this relaxing seasonal cottage, situated high above road level and offering breathtaking panoramic views of the 444-acre Highland Lake. Enter through the oversized screened porch, where you can unwind with family or friends while taking in the beautiful perennial plantings and natural surroundings. This charming cottage features two bedrooms, a loft, one full bath, an open-concept

  Debra Jablonski Berkshire Hathaway NE Prop.

  347 W Wakefield Blvd, Winsted, CT 06098
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  /23

  $319,900

  New Construction $20K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,034 Sq Ft

  14 Bank St, Winsted, CT 06098

  New Construction - Easy to Maintain - Open Floor Plan - Central Air - Vinyl Plank flooring throughout. White Shaker Kitchen with Island and granite countertops. All stainless steel kitchen appliances. Separate laundry room on main level. Glass paneled door to covered deck off the living room area. Two spacious bedrooms with large closets. Entry foyer with large walkin closet Large heated garage

  David White OwnerEntry.com

  14 Bank St, Winsted, CT 06098
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  /26

  $1,080,000

  $120K PRICE DROP

  • 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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  /21

  $879,990

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

  000000 Norfolk Rd, Winchester, CT 06098

  Rare Multi-Parcel Land Opportunity 5 Contiguous Parcels | Colebrook & Winchester, CT Discover an exceptional land offering spanning five contiguous parcels across two of Litchfield County's most desirable rural towns. This unique property features a strong presence in highly sought-after Colebrook, known for its scenic beauty, low-density living, and unspoiled New England charm-paired with the

  John Harney William Pitt Sotheby's Int'l

  000000 Norfolk Rd, Winchester, CT 06098
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  /40

  $304,900

  $15K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,192 Sq Ft

  325 E Wakefield Blvd, Winsted, CT 06098

  Enjoy beautiful water views and access to Highland Lake from this inviting home offering comfortable living spaces and desirable features throughout. The main level features a galley kitchen with plentiful white cabinetry, laminate flooring, refrigerator, dishwasher, and electric range. A convenient powder room and stackable washer add functionality. The spacious living room/dining area features

  Anthony Gonsalves RE/MAX RISE

  325 E Wakefield Blvd, Winsted, CT 06098
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  /19

  $425,000

  • 3 Beds
  • 1.5 Baths
  • 1,952 Sq Ft

  120 Moore Ave, Winsted, CT 06098

  Situated on a side street just outside the town, this contemporary 3-bedroom residence exudes an open and spacious ambiance, enhanced by vaulted ceilings that impart a sense of grandeur to the living room. The home features numerous updates, including a stunning kitchen, two living areas, a separate dining space, and two decks accessible from both the dining and living rooms. The first-floor

  Liza Reiss Elyse Harney Real Estate

  120 Moore Ave, Winsted, CT 06098
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  /13

  $850,000

  • Land
  • 39,204 Sq Ft
  • $944,444 per Acre

  414 E Wakefield Blvd, Winsted, CT 06098

  An exceptional opportunity to create your dream home on the shores of highly sought-after Highland Lake. This waterfront property at 414 E Wakefield Boulevard offers the perfect setting to bring your vision of lakefront living to life. Existing plans for an impressive approximately 4,000-square-foot waterfront home are available, giving you the option to move forward with an already thoughtfully

  Annie Q Simard LPT Realty

  414 E Wakefield Blvd, Winsted, 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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  /3

  $79,900

  • Land
  • 1.32 Acres
  • $60,530 per Acre

  -00 Colebrook Rd, Colebrook, CT 06021

  Set in the quiet beauty of Colebrook, this 1.32-acre approved building lot offers an excellent opportunity to bring your new home plans to life. Much of the early groundwork has already been completed, including a perc test, survey, driveway plan, septic design, and approvals for up to a 4-bedroom home, helping streamline the path from concept to construction. The lot has been cleared, offering a

  Steve Howey Coldwell Banker Realty

  -00 Colebrook Rd, Colebrook, CT 06021
• 

  

  /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
• 

  

  /19

  $150,000

  • Land
  • 6.18 Acres
  • $24,272 per Acre

  0 Ashley Rd Unit Lot 6, Winchester, CT

  Build Your Dream Retreat in Litchfield County! Escape the noise and pace of the city and discover 6.18 private wooded acres nestled in the scenic hills of Winchester, Connecticut. This approved 4-bedroom building lot offers the perfect opportunity to create a custom home or weekend retreat surrounded by nature, all within an easy drive of New York City and The Berkshires. Located just 200 yards

  Pascale Nejaime William Pitt Sotheby's Int'l

  0 Ashley Rd Unit Lot 6, Winchester, CT
• 

  

  /40

  $715,000

  $20K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 3,158 Sq Ft

  44 Pine Rd, Colebrook, CT 06021

  Enjoy exceptional privacy and peaceful country living in this spacious 4 bedroom, 2.5 bath contemporary Cape set atop a long winding driveway surrounded by natural beauty. The open floor plan on the main level offers comfortable living and entertaining spaces, including an updated eat in kitchen with stainless steel appliances, a dining room with a cozy wood burning fireplace, a generous living

  Mike Gregor Cohen Agency SiM, LLC

  44 Pine Rd, Colebrook, CT 06021

Showing Results 1 - 40, Page 1 of 2

Why Live in Winchester

Winchester, located in the Litchfield Hills of Connecticut, is known for its rural charm and scenic mountain views. This town, often referred to as the Gateway to the Berkshire Mountains, offers a variety of outdoor recreational activities. Highland Lake, a popular attraction, features two public beaches, a boat launch, and a marina with boat rentals and seasonal slips. Winchester Lake and Park Pond provide quieter spots for boating and freshwater fishing. Platt Hill State Park offers unmarked nature trails for hikers and birdwatchers, while nearby Burr Pond, Sunnybrook, and Stillwater Pond State Parks are within 5 miles. The Sue Grossmann Still River Greenway provides a paved path for walking, running, and biking. Green Woods Country Club boasts one of the only three 10-hole golf courses in the United States. Winsted, the downtown area of Winchester, has a walkable Main Street with shops, eateries, and creative spaces like Whiting Mills and the American Mural Project. The Gilbert School, a private secondary school functioning as the public middle and high school, is highly rated and offers various sports programs. Housing options in Winchester range from historic New England-style farmhouses and saltbox homes to Cape Cod and raised ranch-style homes in Winsted, with lakefront properties being more expensive. Winchester is car-dependent, with limited public transportation, but U.S. Route 44 and state Route 8 provide access to Torrington, Hartford, and Bradley International Airport, which is 29 miles away.

Learn more about living in Winchester

Winchester, CT Home Prices

	Winchester, CT
Median Home Price	$359,900
Median Sale Price	$370,000 +5% YoY
Avg. Price per Square Foot	$232
Median Single Family Price	$370,000
Total Active Listings	50 listings
Market Conditions	0 Months of Supply Seller's Market

Frequently Asked Questions

What is the average home price in Winchester, CT?

Homes for sale in Winchester, CT have an average home price of $358,266.

How many homes have sold over the last 12 months in Winchester, CT?

3 homes have sold in Winchester, CT over the last 12 months.

What is the average household income in Winchester, CT?

The average household income in Winchester, CT is $87K.

What are the most popular zip codes in Winchester, CT?

The most popular zip codes in Winchester, CT include 06098, 06790, 06021, 06058 and 06063.

How much do you need to make to afford a house in Winchester?

The median home price in Winchester is $359,900. If you put a 20% down payment of $72,000 and had a 30-year fixed mortgage with an interest rate of 6.95%, your estimated principal and interest payment would be $1,910 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $82K a year to afford the median home price in Winchester. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Winchester is $87K.

How are the schools in Winchester, CT?

Winchester, CT has highly rated public and private schools. Some of the best schools in Winchester based on Niche Grades are Colebrook Consolidated School, Lakeview High School and Northwestern Regional High School. Browse all the schools in Winchester, CT to learn more.