Litchfield, CT Homes

• 

  $679,000 Sold Apr 30, 2025

  • 3,870 Sq Ft
  • $175/SF
  • 5 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1984

  110 South Rd, Winsted, CT 06098

  Discover your private sanctuary in the heart of historic Winchester Center, where tranquility meets nature! This contemporary Cape-style home boasts spacious, light-filled rooms that have been thoughtfully updated throughout. Elegant details such as crown molding, beams, skylights & oversized windows invite the beauty of the outdoors in-all showcasing your private pond! The main floor is designed

  Matthew Egan Regency Real Estate, LLC

  110 South Rd, Winsted, CT 06098
• 

  Est $226,064 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,236 Sq Ft

  42 Upland Rd, Winsted, CT 06098

  42 Upland Rd, Winsted, CT 06098
• 

  

  

  /24

  $199,900 Pending

  • 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
• 

  $160,000 Sold Apr 29, 2025

  • 992 Sq Ft
  • $161/SF
  • 0 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1986

  14 Riveredge Dr Unit 14, Winsted, CT 06098

  Come see this wonderful sought after condo in a great neighborhood that has been freshly painted and all new appliances in the kitchen as well as a newer water heater that is just a few years old. Close proximity to town and route 8 and just down the street from the Northwestern Connecticut Community College. This unit has a garage that is directly across from the condo and has an additional

  Maria Smith KW Legacy Partners

  14 Riveredge Dr Unit 14, Winsted, CT 06098
• 

  Est $306,000 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,622 Sq Ft

  125 E Mountain Ave, Winsted, CT 06098

  125 E Mountain Ave, Winsted, CT 06098
• 

  

  /18

  $234,000 Pending

  • 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
• 

  $90,000 Sold Apr 25, 2025

  • 936 Sq Ft
  • $96/SF
  • 18 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1935

  109 Marshall St, Winsted, CT 06098

  Charming bungalow with great potential! This 936 sq. ft. home features 6 rooms, including 3 bedrooms and 1 full bath, situated on a spacious 0.80-acre lot. A detached one-car garage provides additional storage or parking. While this home is in poor condition and will require significant renovation, it presents an excellent opportunity for investors or buyers looking to restore and customize. Will

  David Sartirana Northwest CT Realty

  109 Marshall St, Winsted, CT 06098
• 

  Est $200,135 Not Listed For Sale

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

  111 Riverton Rd Unit 35, Winsted, CT 06098

  111 Riverton Rd Unit 35, Winsted, CT 06098
• 

  

  /40

  $750,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,488 Sq Ft

  266 Perch Rock Trail, Winsted, CT 06098

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

  Laurie Murray KW Legacy Partners

  266 Perch Rock Trail, Winsted, CT 06098
• 

  $410,000 Sold Apr 24, 2025

  • 2,313 Sq Ft
  • $177/SF
  • 28 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1971

  52 Lakeview Rd, Winsted, CT 06098

  Welcome to 52 Lakeview Rd, a meticulously maintained Colonial home that has been lovingly cared for by the same family for over 50 years. This 2,300 sq. ft. residence is set on a spacious .47-acre lot in a peaceful, rural neighborhood, offering both privacy and convenience. The main level features a well-designed layout, including a formal living room and dining room, perfect for entertaining.

  David Sartirana Northwest CT Realty

  52 Lakeview Rd, Winsted, CT 06098
• 

  Est $199,953 Not Listed For Sale

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

  111 Riverton Rd Unit 54, Winsted, CT 06098

  111 Riverton Rd Unit 54, Winsted, CT 06098
• 

  

  /26

  $270,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 1,752 Sq Ft

  141 Maloney Ct, Winsted, CT 06098

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

  Marcy D'Angelo Coldwell Banker Realty

  141 Maloney Ct, Winsted, CT 06098
• 

  $220,000 Sold Apr 24, 2025

  • 3,115 Sq Ft
  • $71/SF
  • 14 Days On Market

  • 5 Beds
  • 4 Baths
  • Built 1900

  830 Main St, Winsted, CT 06098

  Large side by side duplex with 1 and half baths on each side and a finished attic on each side. Lots of potential here but freeze damage as well. As is sale or repairs possible.

  Michelle Grant Coldwell Banker Premier Real Estate

  830 Main St, Winsted, CT 06098
• 

  Est $325,454 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,249 Sq Ft

  143 Mountain Rd, Winsted, CT 06098

  143 Mountain Rd, 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
• 

  $275,000 Sold Apr 23, 2025

  • 2,191 Sq Ft
  • $126/SF
  • 41 Days On Market

  • 5 Beds
  • 2 Baths
  • Built 1880

  151 Elm St, Winsted, CT 06098

  Step into the warmth and character of this beautiful 5-bedroom single-family home, ideally located in the heart of Winsted. With a wrap-around front porch and a screened rear porch, this home offers the perfect blend of classic charm and modern convenience. Inside, you'll find hardwood floors throughout most of the house, a full bay window in the living room that fills the space with natural

  Jeffrey Liskin Northwest CT Realty

  151 Elm St, Winsted, CT 06098
• 

  Est $226,423 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,488 Sq Ft

  97 Prospect St, Winsted, CT 06098

  97 Prospect St, Winsted, CT 06098
• 

  

  /3

  $349,900 Coming Soon

  • 5 Beds
  • 2 Baths
  • 2,531 Sq Ft

  41 Lovely St, Winsted, CT 06098

  Lovely 2 family home on a side street ,not far from Highland lake, parks, town hall, restaurants and shopping . The home is in move in condition and features updated ,fully applianced kitchens & updated baths, wood floors and Vinyl windows.The 1st floor features 6 rooms , 3 bedrooms and 1 bath with access to the basement. The second floor features 5 rooms , 2 bedrooms and 1 bath with access to a

  Mary Mary LeBlanc Realty

  41 Lovely St, Winsted, CT 06098
• 

  $289,900 Sold Apr 21, 2025

  • 988 Sq Ft
  • $293/SF
  • 61 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1980

  315 E Wakefield Blvd, Winsted, CT 06098

  Charming ranch style home with year round water views! This beautifully updated 3-bedroom, 1-bath ranch home in the sought-after Highland Lake community in Winsted is a true gem. The home has been meticulously cared for, blending modern updates with classic charm. Inside, you'll find a cozy, well-maintained living space that feels inviting and comfortable. The property boasts a spacious, full

  Heather Crabtree Coldwell Banker Realty

  315 E Wakefield Blvd, Winsted, CT 06098
• 

  Est $211,933 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,759 Sq Ft

  11 Orchard St, Winsted, CT 06098

  11 Orchard 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
• 

  $290,000 Sold Apr 21, 2025

  • 2,338 Sq Ft
  • $124/SF
  • 6 Days On Market

  • 5 Beds
  • 2 Baths
  • Built 1886

  18 Upland Rd, Winsted, CT 06098

  A Great Investment opportunity in this classic charming multi two unit home. The location is convenient to many amenities including Dining, Community College, Highland Lake recreation and much more. Each unit has Washer & Dryer hookups. Up grades include New High Gas Efficiency Furnaces and Hot Water Heaters in 2020. New Thermal Windows & Blown In Insulation 2021 & 2022. Two Car Garage, Large

  Linda Ganem Borla & Associates Real Estate

  18 Upland Rd, Winsted, CT 06098
• 

  Est $228,531 Not Listed For Sale

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

  118 Meadow St, Winsted, CT 06098

  118 Meadow 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
• 

  $275,000 Sold Apr 17, 2025

  • 1,287 Sq Ft
  • $214/SF
  • 22 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1948

  58 Cherry St, Winsted, CT 06098

  Charming Cape Cod retreat just a short stroll from the beautiful beaches of Highland Lake! This well-maintained 3-bedroom, 2-bath home has been a cherished getaway for years, offering the perfect blend of comfort and convenience. The main level features a sun-filled living room, a dining room ideal for gatherings, and a kitchen with a center island for easy meal prep. A cozy bedroom and a full

  David Sartirana Northwest CT Realty

  58 Cherry St, Winsted, CT 06098
• 

  Est $259,208 Not Listed For Sale

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

  151 Hinsdale Ave, Winsted, CT 06098

  151 Hinsdale Ave, Winsted, CT 06098
• 

  

  /37

  $319,900 Under Contract

  • 2 Beds
  • 1.5 Baths
  • 1,034 Sq Ft

  389 Colebrook River Rd, Winsted, CT 06098

  Charming Bungalow with a cozy cottage feel, beautifully updated and ready to enjoy! The main level features a warm and inviting country kitchen with breakfast bar, an open dining area with sliders leading to the rear deck, a spacious living room with access to a classic farmhouse-style front porch, and a convenient half bath. Upstairs offers two modest bedrooms, a full bath, and a small office or

  David Sartirana Northwest CT Realty

  389 Colebrook River Rd, Winsted, CT 06098
• 

  $275,000 Sold Apr 16, 2025

  • 1,277 Sq Ft
  • $215/SF
  • 114 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1940

  493 N Main St, Winsted, CT 06098

  Highest and best by 3/10 at 6 PM. Back on the market! Enjoy living in your own home nestled in the scenic Litchfield Hills in this newly renovated three-bedroom house with many updates: Refrigerator, range, microwave, dishwasher, and first floor washer/dryer less than a year old. Hot water heater 2023. Updated electrical 2024. Furnace serviced and updated with new burner 2024. 3 new exterior

  Jessica Sperry Maverick Realty

  493 N Main St, Winsted, CT 06098
• 

  Est $465,984 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
• 

  

  /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
• 

  $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 $327,598 Not Listed For Sale

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

  5 Hillside Ave, Winsted, CT 06098

  5 Hillside Ave, 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
• 

  $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 $213,980 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
• 

  

  /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
• 

  $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 $202,590 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
• 

  

  /30

  $335,000 Under Contract

  • 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
• 

  $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

Showing Results 121 - 160, Page 4 of 18