Litchfield, CT Homes

• 

  $395,000 Sold Apr 08, 2025

  • 1,818 Sq Ft
  • $217/SF
  • 106 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1875

  47 Orchard St, Winsted, CT 06098

  Renovated to 4 Bedroom and 3 Full-bath home with 2028 SQFT, this stunning Colonial on Private Road a short walk to Highland Lake. This newly remodeled 1875 home seamlessly blends historic charm with modern amenities. Inside discover a spacious floor plan offering an abundance of natural light perfect for both entertaining and everyday living. The custom kitchen is a chef's dream featuring sleek

  Bryan Palladino Showcase Realty, Inc.

  47 Orchard St, Winsted, CT 06098
• 

  Est $205,179 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,759 Sq Ft

  11 Orchard St, Winsted, CT 06098

  11 Orchard St, Winsted, CT 06098
• 

  

  

  /39

  $559,999 Pending

  • 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

  144 Marshall St, Winsted, CT 06098
• 

  $305,000 Sold Apr 07, 2025

  • 1,826 Sq Ft
  • $167/SF
  • 62 Days On Market

  • 5 Beds
  • 2 Baths
  • Built 1900

  178 Boyd St, Winsted, CT 06098

  Rare Side-by-Side Duplex with Highland Lake Views Don't miss this unique side-by-side duplex offering stunning views of Highland Lake! This versatile property features an open-concept layout on the first floor in both units, creating a spacious and inviting atmosphere. One unit boasts a vaulted ceiling in the updated kitchen, while the other offers a finished attic that adds two additional

  David Sartirana Northwest CT Realty

  178 Boyd St, Winsted, CT 06098
• 

  Est $234,474 Not Listed For Sale

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

  118 Meadow St, Winsted, CT 06098

  118 Meadow St, Winsted, CT 06098
• 

  

  /39

  $310,000 Pending

  • 3 Beds
  • 5 Baths
  • 2,623 Sq Ft

  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
• 

  $206,000 Sold Apr 01, 2025

  • 1,204 Sq Ft
  • $171/SF
  • 22 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1987

  111 Riverton Rd Unit 9, Winsted, CT 06098

  This 3-story condominium boasts two large bedrooms, and 1.5 bathrooms, as well as a 2-car garage with a private indoor entrance. The primary bedroom provides lofty ceilings, a walk-in closet, and its own entry way into the full bath. On the main level, the pellet stove is powerful enough to heat the entire living space whilst having its own thermostat to ensure a comfortable temperature

  Kathleen Miller CT Home Pro, LLC

  111 Riverton Rd Unit 9, Winsted, CT 06098
• 

  Est $265,560 Not Listed For Sale

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

  151 Hinsdale Ave, Winsted, CT 06098

  151 Hinsdale Ave, Winsted, CT 06098
• 

  

  /24

  $1,500,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,664 Sq Ft

  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
• 

  $270,000 Sold Mar 31, 2025

  • 1,192 Sq Ft
  • $227/SF
  • 39 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1930

  325 E Wakefield Blvd, Winsted, CT 06098

  Enjoy water views from this charming Colonial located just across the street from Highland Lake. This cozy retreat blends historic charm with modern updates, offering a perfect escape for year-round living or a weekend getaway. Inside, refinished wide-plank hardwood floors add warmth and character, while the freshly painted interior enhances the bright and inviting atmosphere. The living room

  Brigitte Richter William Pitt Sotheby's Int'l

  325 E Wakefield Blvd, Winsted, CT 06098
• 

  Est $493,293 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,364 Sq Ft

  16 Alexandria Dr, Winsted, CT 06063

  16 Alexandria Dr, Winsted, CT 06063
• 

  

  /3

  $320,000 Pending

  • Land
  • 0.61 Acre
  • $524,590 per Acre

  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
• 

  $395,000 Sold Mar 28, 2025

  • 1,792 Sq Ft
  • $220/SF
  • 25 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1990

  102 Sunny Ridge Dr, Winsted, CT 06098

  Charming One-Owner Split Level in a Private Rural Setting. Discover the perfect blend of privacy, space, and convenience in this beautifully maintained 1,800 sq. ft. split-level home, nestled on a serene 1-acre lot at the end of a cul-de-sac abutting the Barkhamsted town line. This home offers seven well-appointed rooms, including a spacious living room with a propane stove set in the fireplace,

  David Sartirana Northwest CT Realty

  102 Sunny Ridge Dr, Winsted, CT 06098
• 

  Est $341,689 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

  $295,000 Pending

  • Land
  • 104 Acres
  • $2,830 per Acre

  00 Pinney St, Colebrook, CT 06098

  Ideal rural parcel for hunting and outdoor recreation. Land rises to the west away from Pinney Street. Wetlands mapping necessary to determine development potential.

  David Taylor Elyse Harney Real Estate

  00 Pinney St, Colebrook, CT 06098
• 

  $85,000 Sold Mar 27, 2025

  • Land
  • 3.06 Acres
  • $27,742 per Acre

  • 5 Days On Market

  0 Platt Hill Rd Unit 24079213, Winsted, CT 06098

  Build on this 3+ acre lot that adjoins Winchester Land Trust. Old soil tests, would need to be re-tested.

  Nadia Corvo Northwest CT Realty

  0 Platt Hill Rd Unit 24079213, Winsted, CT 06098
• 

  Est $217,761 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
• 

  

  /37

  $495,000 Coming Soon

  • 4 Beds
  • 1.5 Baths
  • 1,940 Sq Ft

  159 Sandy Brook Rd, Colebrook, CT 06021

  Introducing Sandy Brook Cottage. Perched gently near the banks of the meandering Sandy Brook, this c.1800 home exudes quiet charm and understated elegance. Set on over 3 picturesque acres in the hidden gem of Colebrook. It is a true country escape. One that offers privacy, character, and an effortless connection to nature. Winding stone walls trace the contours of the rolling landscape, creating

  Lenore Mallett William Pitt Sotheby's Int'l

  159 Sandy Brook Rd, Colebrook, CT 06021
• 

  $135,000 Sold Mar 27, 2025

  • 643 Sq Ft
  • $210/SF
  • 72 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1986

  13 Riveredge Dr Unit 13, Winsted, CT 06098

  This is your chance to experience turnkey condo-style living with modern upgrades and unbeatable comfort. The remodeled kitchen boasts newer appliances, sleek granite countertops, and stylish flooring, perfect for everyday living and entertaining. Enjoy peace of mind with a five-year-old water heater with a 10-year warranty. Imagine waking up to the serene, calming sounds of the river through

  James Bradshaw Berkshire Hathaway NE Prop.

  13 Riveredge Dr Unit 13, Winsted, CT 06098
• 

  Est $204,676 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
• 

  

  /28

  $264,900 Under Contract

  • 3 Beds
  • 1 Bath
  • 1,058 Sq Ft

  22 Stanton Ave, Winsted, CT 06098

  Welcome to this well-maintained 3-bedroom, 1-bathroom home located on a quiet street in the heart of Winsted. Offering 1,058 square feet of comfortable living space, this home features beautiful hardwood floors throughout and a practical layout ideal for everyday living. The kitchen includes a gas range, and the home is equipped with efficient natural gas heating and hot water, helping to keep

  Jeffrey Liskin Northwest CT Realty

  22 Stanton Ave, Winsted, CT 06098
• 

  $268,000 Sold Mar 18, 2025

  • 1,428 Sq Ft
  • $188/SF
  • 128 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1880

  86 Maple St, Winsted, CT 06098

  Completely renovated. Brand new appliances. Roof and furnace approx. 10 years old. Nice open yard. New gravel driveway. Walk up attic with plenty of storage. New floors and windows. Large eat-in kitchen with marble counters and stainless steel appliances. Main floor laundry. Two full baths; one upstairs and one on main level. One main level bedroom. 86 Maple St is waiting for you to make it your

  Chris LaCava Coldwell Banker Realty

  86 Maple St, Winsted, CT 06098
• 

  Est $210,534 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 528 Sq Ft

  12 Charles St, Winsted, CT 06098

  12 Charles St, Winsted, CT 06098
• 

  

  /17

  $279,900 Under Contract

  • 3 Beds
  • 1 Bath
  • 1,183 Sq Ft

  39 Colony Dr, Winsted, CT 06098

  Well-maintained 3-bedroom, 1-bath Cape located in a quiet neighborhood in Winchester. Features include dining area with hardwood floors, natural gas heat, and a top notch alarm system. Roof is less than 10 years old. Functional layout with flexible living space and a manageable yard for outdoor enjoyment. Sale is contingent upon successful purchase of seller's new property.

  Alison Behlman Tier 1 Real Estate

  39 Colony Dr, Winsted, CT 06098
• 

  $105,000 Sold Mar 14, 2025

  • 720 Sq Ft
  • $146/SF
  • 33 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1950

  350 Walnut St, Winsted, CT 06098

  Attention investors! This 2-bedroom, 1-bathroom single ranch style home is a prime opportunity for a complete rehab. The property was involved in a fire and requires a full rehab with a 1-car garage and is being sold as-is. Subject to probate approval.

  Vincent Miller Hudson Home Services LLC

  350 Walnut St, Winsted, CT 06098
• 

  Est $212,372 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,310 Sq Ft

  20 Gay St, Winsted, CT 06098

  20 Gay St, Winsted, CT 06098
• 

  

  /19

  $194,900 Under Contract

  • 3 Beds
  • 1 Bath
  • 1,446 Sq Ft

  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
• 

  $199,900 Sold Mar 12, 2025

  • 1,204 Sq Ft
  • $166/SF
  • 87 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1987

  111 Riverton Rd Unit 17, Winsted, CT 06098

  Two bedroom, 1 & 1/2 bath end unit Townhouse with wood floors throughout, living room with fireplace and sliders to deck, primary bedroom with walk in closet, deck has just been painted, Spacious 2 car garage. Unit has lower-level laundry room with entry into garage. Great space and ready for New Owner.

  Joanne Donne The Washington Agency

  111 Riverton Rd Unit 17, Winsted, CT 06098
• 

  Est $236,803 Not Listed For Sale

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

  9 Fruit St, Winsted, CT 06098

  9 Fruit St, Winsted, CT 06098
• 

  

  /16

  $315,000 Under Contract

  • 4 Beds
  • 3 Baths
  • 2,861 Sq Ft

  267 Rockwell St, Winsted, CT 06098

  Great opportunity to own a spacious, fully rented 3-family property on a level .86 acre lot, just a short walk to Highland Lake. This home includes a 2-3 bedroom multi level apartment as well as two 1 bedroom apartments, ideal for tenants or extended family. The property features a large parking area and 3 garage spaces, perfect for storage or added rental value. Enjoy the open yard, and a

  Austin Brochu Sullivan Real Estate Inc

  267 Rockwell St, Winsted, CT 06098
• 

  $260,000 Sold Mar 10, 2025

  • 1,888 Sq Ft
  • $138/SF
  • 27 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1973

  14 Hamill Dr, Winsted, CT 06098

  Welcome to this single family home nestled at the end of a peaceful cul-de-sac. Featuring 3 spacious bedrooms and a full bathroom on the main lever, and a cozy lower-level family room complete with a half bath and ample storage. This home has both comfort and functionality.

  Eva Casoria eXp Realty

  14 Hamill Dr, Winsted, CT 06098
• 

  Est $338,028 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
• 

  

  /22

  $299,900 Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,747 Sq Ft

  17 Adams St, Winsted, CT 06098

  Nestled in the charming New England town of Winsted, this classic three-bedroom, two-bathroom home at 17 Adams Street offers a blend of traditional charm and comfortable living. The property boasts a welcoming exterior with a distinguished facade, a covered front porch, and a well-maintained lawn, all framed by mature trees that provide a sense of privacy and tranquility. A convenient driveway

  Michelle Grant Coldwell Banker Premier Real Estate

  17 Adams St, Winsted, CT 06098
• 

  $325,000 Sold Mar 07, 2025

  • 1,324 Sq Ft
  • $245/SF
  • 1 Day On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1962

  11 Cherry St, Winsted, CT 06098

  Welcome to 11 Cherry Street! This move-in ready ranch-style home features 3 bedrooms, 1.5 bathrooms, and is just around the corner from Highland Lake. Step into the kitchen directly from the heated 2-car garage. The kitchen features plenty of white cabinets, shiplap, and a brick backsplash, creating a stylish industrial modern vibe. It also overlooks the spacious dining room perfect for

  Haylee Munchgesang Coldwell Banker Realty

  11 Cherry St, Winsted, CT 06098
• 

  Est $450,224 Not Listed For Sale

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

  123 Skinner Rd, Winsted, CT 06098

  123 Skinner Rd, Winsted, CT 06098
• 

  

  /36

  $299,000 Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,736 Sq Ft

  38 Upland Rd, Winsted, CT 06098

  Estate Owned 3 to 4 Bedroom Colonial in Immaculate Move In Condition! Tucked away on a quiet street but within walking distance of Schools, Medical Facilities and Shopping. Special features include a huge cedar closet, Hardwood floors throughout the entire house, bay windows, 24' x 14' Family Room with Propane Gas Stove and an Oversized Full Bath The Master Bedroom features its own office.

  Holly Blinkoff Cohen Agency

  38 Upland Rd, Winsted, CT 06098
• 

  $400,000 Sold Mar 03, 2025

  • 4,253 Sq Ft
  • $94/SF
  • 132 Days On Market

  • 7 Beds
  • 3.5 Baths
  • Built 1958

  296 Colebrook Rd, Winsted, CT 06098

  . The Main house features a Huge Stone fire-placed family room , plus a fire-placed Living room,for cozier gatherings. The home also includes a walk-out basement,. There is finished space ideal for an in-law suite on the second floor, located above the oversized attached 2-car garage. Outdoor living is enhanced by a rear deck that overlooks a tranquil pond, dam, and wooded area, making it a

  David D'Amore Northwest CT Realty

  296 Colebrook Rd, Winsted, CT 06098
• 

  Est $201,223 Not Listed For Sale

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

  111 Riverton Rd Unit 60, Winsted, CT 06098

  111 Riverton Rd Unit 60, Winsted, CT 06098
• 

  

  /27

  $388,000 Under Contract

  • 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. Pellet stove in the main dining room. Refinished wide pine flooring. Large main Kitchen with lots of cabinet space

  Christine Hunter Hunter Real Estate, LLC

  409 N Main St, Winsted, CT 06098
• 

  $135,000 Sold Feb 28, 2025

  • 816 Sq Ft
  • $165/SF
  • 3 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1939

  234 E Wakefield Blvd, Winsted, CT 06098

  Abundant opportunity awaits for you to live in the highly-desired Highland Lake area. With some vision and determination, you can transform this property into your home. The property features newer roofing, new siding, and new replacement windows. There is a level lot for your enjoyment and a two-car garage with loft storage above. This property could also be a great investment opportunity. Cash

  Jeffrey Liskin Northwest CT Realty

  234 E Wakefield Blvd, Winsted, CT 06098

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