The median home value in Winchester, CT is $312,000.
This is
lower than
the county median home value of $345,200.
The national median home value is $338,100.
The average price of homes sold in Winchester, CT is $312,000.
Approximately 51.37% of Winchester homes are owned,
compared to 34.14% rented, while
14.49% are vacant.
Winchester real estate listings include condos, townhomes, and single family homes for sale.
Commercial properties are also available.
If you see a property you’re interested in, contact a Winchester real estate agent to arrange a tour today!
Open House:
Saturday, 11/9 12:00-2:00PM
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 functionality to the space. Additional highlights include modern stainless steel appliances, with all appliances included, and hardwood flooring throughout the home. The beautifully landscaped yard creates a perfect outdoor space for relaxation and gatherings. Conveniently located near local amenities, this home provides easy access to shopping, dining, and more. Experience this beautiful home firsthand Don't miss the opportunity to make this move-in ready gem your new home.
Lovely Country home located on the outskirts of town features 8 rooms 4 bedrooms and 2 full baths . The living room has a cathedral ceiling with a pellet stove and is open to the fully applianced remodeled Cherry kitchen with granite counters and tiled floor. The breakfast nook features a sliders that walks out to a spacious screened sunroom. The formal dining room has wood floors and a bay window .The 1st floor family room has a cathedral ceiling and beautiful built in cabinets and book shelves . There is access to the master suite from this wing of the house. There are 3 bedrooms ,a laundry room and a full bath on the main level . The master suite has a private staircase to the 2nd floor .The master bedroom is a sunny room with a cathedral ceiling , built in shelving and has a walk in closet and full bath . Great space for inlaw. . There is a pull down attic access for storage and a large 2 car garage with attic storage . As you walk around the yard you notice a garden area and shed , nice fire pit and a deck . There is a full house generator that runs on propane. The roof has architectural shingles . The house has vinly siding . There is a small pond in the woods but is not in view or used .
Winchester! The foothills of the Berkshires! Step inside 14 Curtice and let your imagination run wild. This home consists 3 bedrooms, 1 bathroom, living and dining rooms, with plenty of living space. The work has begun with beautiful new siding, new windows, and a recently updated roof, just bring your kitchen dreams and transform the rest to make it your own. Wonderful opportunity to live in a quiet area, walking distance to the Gilbert school, The YMCA, and downtown shops with great restaurants, theatre, fitness, pottery, something for everyone!
Single family home close to town with spacious bedrooms and living space. Plenty of storage and parking. Close to all forms of transportation, schools and shopping. Come check it out today!!
USE RESTRICTIONS: **GAS AND CONVENIENCE STORE** Take advantage of this unique opportunity to own or lease a versatile 2,400 SF freestanding building, formerly a Cumberland Farms gas station and convenience store. Priced at $699,000 for purchase or available for a ten-year triple net lease with a 3% annual increase, the property offers flexible options including renewal terms, lease-to-own, and consideration for shorter lease durations. Located in a prime area with high visibility and accessibility, the site benefits from proximity to highways, shopping centers, and restaurants, with an impressive daily traffic count of approximately 14,300 cars. While gas station and convenience store operations are restricted, the property is permitted for a wide range of uses, such as a BAKERY, BANK, COMMISSARY, SMALL-FORMAT DRUG STORE, MEDICAL or PROFESSIONAL OFFICE, RESTAURANT, QSR, RETAIL STORE, SMOKE SHOP, or DELI. Special permit uses include AUTOMOTIVE SALE and REPAIR, and BREWPUB.
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 family room with granite fireplace with views in all directions. Sunroom with radiant heated stone flooring, extensive stone patios, pergola, gardens, terraces, sandy beach/swimming area. This is it!
Rarely Available End Unit at Riverwalk Condos! This pristine 2-bedroom, 1.5-bath condo offers a move-in ready experience with stunning river views and modern upgrades. The open-concept living space is filled with natural light and features crown molding and recessed lighting, adding an elegant touch to the living room. The stylish kitchen includes a new microwave, glass-top stove, and fresh paint throughout. Stay comfortable year-round with new A/C units and ceiling fans in the bedrooms. The setup for a pellet stove adds cozy potential to the space. A rare find in the area, this unit comes with a 2-car garage under the unit, along with spacious parking for convenience. Nestled in a well-cared-for complex, enjoy the perfect balance of privacy and community, with easy access to local amenities. Don't miss your chance to own this beautifully maintained home!
Prime Commercial Property at 1 Lake Street. This 4,852-square-foot commercial building is located in the heart of the highly desirable Litchfield County, positioned on a prominent corner lot with exceptional visibility and easy access. Surrounded by thriving businesses and a strong consumer base, this property is perfectly suited for a variety of commercial uses. The building's open layout allows for versatile customization, making it ideal for a range of industries, including retail, office space, showrooms, or even a combination of these uses. Currently, the space is divided into four large sections, each approximately 700 square feet, along with 300 square feet of dedicated office space. Additionally, the building features separate men's and women's bathrooms (each with three fixtures), a handicap/family restroom, and a modest-sized kitchen. With clear-span construction, the interior walls are easily movable, offering maximum flexibility for redesign or reconfiguration to suit your business needs. The property is zoned as Town Center, allowing for numerous potential uses, such as: Accessory Residential Uses,Artisan Production, Bakery, Banks & Financial Institutions (without Drive-Thru), Commissary, Cultural Institutions Small Format Drug Store, Family Day Care Home, Home Occupation, Small Format Medical Offices, Business & Professional Offices, Restaurants, Small Format Grocery Retail, Personal Service Retail, Small Shops
This single family home has 3 generous bedrooms and 1.5 bathrooms. It features a spacious kitchen with hardwood cabinets and black appliances. There are hardwood floors throughout the entire house, a dedicated laundry room, and a heated finished basement. This home is situated on a cul-de-sac and is close to highways and shopping. It also features a serene backyard that is ready for enjoyment.
Make this newly renovated house in the sought after Highland Lake community your full time residence or your home away from home! This home has gone through an extensive remodel including brand new roof, insulated siding, energy efficient windows, and LVP flooring. The home features a new large eat-in kitchen with brand new smart stainless steel appliances, living room, and remodeled full bathroom, with a bluetooth enabled exhaust fan, downstairs. Upstairs features 3 bedrooms plus an additional room that can be used as an office or playroom with newly added baseboard heat and partial views of Highland Lake. Make memories with friends and family in the nicely sized, flat yard. Imagine yourself enjoying life in this stunning home close to beach access and boat launch- make it yours today, this won't last long!
. 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 peaceful retreat. For gardening enthusiasts, an attached 9 x 26 Greenhouse is available. In addition to the main house, the property includes a 2-stall Barn, a Bunkhouse, and a detached 2-car garage with workshop, offering ample space for storage or hobbies. This property provides privacy, space, and endless opportunities for customization, making it an ideal choice for those looking for both comfort and potential. In need of Work , but well worth the effort. Being Sold "AS IS "
This unique offering includes two commercial parcels sold together, situated along bustling Route 44. The first parcel spans 1.08 acres and features a 648 sq. ft. masonry building, ideal for retail or a takeout food establishment, which has a history of both. The second parcel consists of 0.35 acres with an 800 sq. ft. structure that has operated for years as a bar and cafe. A large portion of the property extends across the scenic Indian Meadow Brook, presenting an exciting opportunity for expansion with the addition of a footbridge. This could open up new possibilities for outdoor seating, additional retail space, or any other creative ventures. Positioned at the west end of town, this location serves as a gateway for traffic coming into Winsted, boasting high visibility and a substantial daily traffic count. Whether you're envisioning food service, retail, or something entirely new, this site is brimming with potential for your next business venture.
WOW - Welcome to 220 Gilbert Ave! Stop by for a visit and view the amazing transformation of this FABULOUS 2 family dwelling. Home has been completely remodeled inside and out. Relax and enjoy the level, private back yard or the sprawling, open front porch. The open floor plan boasts, spacious rooms, space for everyone and storage galore! The list of amenities is endless in this beautiful home! Nothing left to do but unpack and enjoy!
Welcome to 19 Cottage Street, a stunning turnkey Colonial in the heart of Winsted that beautifully blends modern functionality with classic charm. As you enter, a spacious foyer with new tile flooring leads into a bright living room featuring gleaming hardwood floors, create a warm, inviting atmosphere. A dedicated office space presents an ideal setting for productivity, while the heart of the home-the expansive kitchen-boasts custom cabinetry, quartz countertops, and sleek appliances. The large island, which seats four, is perfect for casual dining or gatherings. Just off the kitchen, a sun-drenched sunroom is ideal for enjoying morning coffee with natural light pouring in. The first floor also features a chic half bath and washer/dryer hookups for added convenience. Upstairs, the master bedroom impresses with a spacious walk-in closet, while two additional bedrooms and two full baths make it perfect for family living or hosting guests. The third level also includes three versatile rooms and an additional half bath-perfect for a home office, playroom, or guest suite. Outside, a new driveway and garage doors add curb appeal, while freshly laid masonry lines the front and back yards, offering stylish outdoor spaces. With its blend of modern updates and timeless design, this home is truly move-in ready. Schedule a viewing today and make 19 Cottage Street your new home!
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 updated appliances, a spacious eat-in area, & an oversized island perfect for meal prep & entertaining. The rest of the main floor is ideal for hosting guests, w/ expansive windows providing stunning views of Highland Lake from every angle. Step outside to a covered front porch, where you can take in breathtaking sunrise views over the water. The second floor is home to the huge Primary bedroom, complete w/ a recently remodeled full bath & two walk-in closets. Four additional spacious bedrooms share Jack & Jill bathrooms, & a second-floor summer porch offers a serene spot to enjoy the natural beauty of the lake. The third floor adds even more space, w/ three additional bedrooms & a full bath that could be updated to reflect your needs. Directly on the lake is a 1/4 acre lot w/ 150+/- ft of water frontage, you'll find a charming lakeside cottage that features a cozy fireplace, kitchenette, full bath, & wrap-around deck. Whether you're relaxing on the dock or enjoying the cottage's amenities, this entire property is perfect for experiencing the best of lakefront living.
If you are looking for a mini estate look no further. This completely remodeled home has everything you need. New eat in kitchen with a bay window overlooking the rear yard. Quartz c/tops and new appliances. Formal dining room, den with fireplace and wood stove insert. Sliders to rear deck and pool. Large living room with hardwood floors. Primary bedroom with full bath and two walk in closets. Two additional bedrooms and another full bath on the second floor. Step outside onto the well landscaped picturesque grounds. You are on a private almost 5 acre parcel that provides privacy but yet close to everything. Take a look!
Welcome to 315 East Wakefield Blvd, a charming 3-bedroom, 1-bath ranch offering stunning views and easy access to Highland Lake. This home is in impeccable condition, featuring an updated kitchen and bath, along with newer hard surface flooring. The inviting living room boasts a propane fireplace, wood stove, and a picture window perfectly framing the serene lake views. The updated eat-in kitchen opens to a covered deck and a fenced-in rear yard, providing additional outdoor space with more picturesque views of the lake. This well-cared-for home is not only a cozy retreat but also a gateway to the year-round recreational activities that Highland Lake offers. Spanning 444 acres, the lake is renowned for its watersports, trophy trout and bass fishing, and a marina where you can rent a slip or even a boat. Whether you're seeking a peaceful lakeside residence or an active lifestyle, 315 East Wakefield Blvd is the perfect place to call home.
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 settles in, the lake becomes a playground for ice fishing, skating, and cozy fireside gatherings, making this a year-round sanctuary. With luxury finishes, a gourmet kitchen, and custom craftsmanship in the main home, plus a charming guest bungalow, this property is ideal for hosting family, friends, or even guests. Zoned for a bed and breakfast and featuring an extra subdividable lot, the estate also holds exciting potential for income generation or expansion. Whether you're envisioning a private retreat, an upscale B&B, or future development with a subdividable lot, this versatile property is the perfect setting for those seeking a dynamic, all-season lake life.
Welcome home! This inviting residence features an open, airy feel with abundant natural light from big windows and multiple skylights. The main level boasts solid hardwood floors and tiles, while the spacious eat-in kitchen, though older, is well-maintained and perfect for family meals. Enjoy three full bathrooms, a central vacuum system, and tons of storage space throughout. The primary bedroom is a cozy retreat with its own fireplace, and the large living room also includes a fireplace for added charm. Outside, you'll find a deck, mature plantings, flower beds, and a handy shed. With a big 2-car garage and a fantastic laundry room, this home has everything you need! This property is being sold As-Is. All inspections for informational purposes only.
Stunning Lake Vistas! Have you been dreaming of a lake view and a property that is Special, Unique and TURN KEY? Fifty feet of waterfront property is included with boat dock and lift for lake enthusiasts! Nestled across from the serene First Bay, this beautifully renovated two-family home can be used as a single family and offers breathtaking water views and modern comforts. Perfect as a family retreat or an income-generating property, the home is fully renovated with upscale finishes throughout and boasts central air, newer appliances, windows, siding, and high-efficiency propane-fueled furnaces. Gorgeous details throughout make this a truly exceptional property. On the first floor, you'll find a rustic custom kitchen w granite, upgraded appliances (sub zero refrigerator and bevg fridge, gas range, dishwasher), a full bathroom w marble and walk-in shower, two spacious bedrooms, and a large family room w French doors leading to a covered wrap around porch to enjoy that view! The second floor unit features a kitchenette with fridge, dishwasher, and range, dining room/office, two bedrooms, and a family room with sliders to a covered porch offering the same amazing landscape! Additional highlights include an oversized two-car detached garage and carport, hot tub(sold as is), level yard area, and side deck. This home is situated just across the street from the water, providing easy access to all lake activities. Rustic yet Upscale! A RARE FIND!
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.
RARE opportunity to purchase a BUILDABLE CORNER LOT on highly sought after HIGHLAND LAKE. Ideally situated on the highly coveted East Side of the lake, the lot offers privacy and stunning water views. With public water and sewer infrastructure in place, this prime corner lot is level and cleared- just waiting for you to make your dreams a reality. Highland Lake, nestled in the foothills of the gorgeous Mountains, is admired throughout New England for its clean water and superb Trout fishing. Enjoy easy lake access for your favorite water sports including swimming, boating and fishing. Whether you're looking to build your permanent residence or a weekend getaway, THE DREAM STARTS HERE!
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 upgrades, fire rated tenant main doors & new fire alarms/strobes in both buildings. The unit mix is: 1, 4 bedroom ($1,100); 4, 2 bedrooms ($1,000; $1,050; $900; the other can be rented for up to $1500 per month) and 2, 1 bedroom units ($950 each). The 175 Main St had a roof replacement in 2021, a privacy fence enclosure installed & all 4 residential units have gone through renovations. 183 Main St has had a roof replacement in 2023, aft wall structural repair, new studs, insulation, beams & siding. 183 2A has been refurbished. One retail space is leased to Noli's Restaurant which has a patio. Noli's pays their heat and electric. The current owner leased the second retail space to Northwest Soup & Deli ($1500 then $1650 on 1/1/2025) and this establishment has all new equipment. They pay their own electric and a fixed gas, water/sewer reimbursement to the Owner. The residential tenants pay their electric. Owners are very meticulous and detail oriented. This is a seamless opportunity to own a well-run asset. Properties being sold together.
Welcome to Strong Island, a waterfront retreat on Highland Lake. The clean waters of Highland Lake in the town of Winchester in Litchfield County surround this 1.6 acres island. History abounds for this property as the original house dates back to 1890. There were significant alterations made in 1920 that added several rooms, a boat house, a barn and porch. Babe Ruth made several trips to Strong Island for his weekends and vacations away from NYC. Strong Island is one of the largest islands on Highland Lake and has the best views. The position of this island give it the longest view of the lake on a North view and also on an Easterly view. The position of the main house on the island, the various docks, piers and out buildings make this property unable to be duplicated today. Strong Island is a trophy property that needs some polishing, but incredible in so many ways.
Your private oasis nestled in historic Winchester Center, offering serenity, lakes, trails and more. Contemporary Cape w/an abundance of spacious, light-filled and updated rooms. Several options to include; one-floor living, multi-generational home, w 4+ bedrooms and 4 garage bays. Rooms are adorned w/crown molding, beams, skylights and oversized windows, bringing the beauty of the outside in. Gazing out the windows, you'll see mature plantings, flowers, wildlife and private pond. The main level of this home features a spacious kitchen w/ walk-in pantry, mudroom, dining rm, formal living rm, library, den, office, sunroom and spacious great room being used as a primary bedroom. Enjoy the Gunite pool and terrace directly outside the sunroom, with several seating areas overlooking beautiful views - a perfect place for entertainment or to retreat for relaxation, reading and conversation. Upper level boasts a primary suite with spa-like full bath w/soaking tub, additional 2 bedrooms w/en suite full bath, laundry room and a central loft overlooking the formal fireplaced living rm. The 4 garage bays are heated - ideal for car enthusiasts and those desiring an oversized workshop.