Refine Search
Map
Sort by
$959,900
2 Beds ⋅ 2 Baths ⋅ COMING SOON Status ⋅ 24194765 MLS
Exceptional Highland Lake waterfront Colonial rebuilt in 1996 to modern standards and codes, offering quality construction and timeless appeal. Perfectly positioned with 58 feet of direct northwest-facing waterfront, this home is designed to capture breathtaking lake views from nearly every angle. The spacious living/great room features a dramatic fieldstone fireplace and walls of glass with multiple sliders leading to a large wraparound waterfront deck, creating a seamless connection between indoor and outdoor living. The beautiful oak kitchen is highlighted by quartz countertops, newer stainless steel appliances, and an open layout that flows effortlessly into the main living areas, making it ideal for entertaining. Upstairs, the primary bedroom boasts soaring 12-foot cathedral ceilings and an abundance of windows overlooking the lake, providing a spectacular place to wake up each morning. Outside, the waterfront has been thoughtfully improved with an updated seawall that includes an aluminum dock, making it easy to enjoy boating, swimming, fishing. Highland Lake is a pristine 444-acre lake renowned for its clean water. Conveniently located just 45 minutes from Hartford and Bradley International Airport, and within easy reach of the Berkshires, Infinity Music Hall, the Warner Theatre, New York City, and Boston, this property offers the perfect blend of year-round living and a weekend retreat. A rare opportunity to create a lifetime of memories.

204 E Wakefield Blvd, Winchester
$299,000
4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24194728 MLS
Excellent opportunity for investors! This well-maintained Victorian-style two-family home offers the perfect blend of character, functionality, and income potential. Each spacious unit features 5 rooms, 2 bedrooms, and 1 full bath, with beautiful hardwood flooring throughout and separate, efficient natural gas heating systems. The upper-level apartment also includes a charming enclosed porch, providing additional seasonal living space and a relaxing retreat. Outside, you'll find a level lot and a unique two-story barn with a full basement, offering exceptional storage, workshop space, or endless possibilities for hobbyists and contractors alike. Conveniently located just minutes from downtown, schools, shopping, dining, and everyday conveniences, this property is ideal whether you're looking to build your investment portfolio or live in one unit while generating rental income from the other. A rare opportunity to own a versatile multi-family property with timeless Victorian charm!

64 Wheeler St, Winchester
$179,990
2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24194479 MLS ⋅ Riverwalk BLDG.
Move right into this well-maintained townhouse offering 2 bedrooms, 1.5 baths, and an attached garage in the desirable Riverwalk community. The spacious living room features a vaulted ceiling, fireplace, and abundant natural light, while the kitchen offers ample cabinet and counter space with sliding door access to a private deck overlooking a wooded backdrop. Upstairs you'll find two generously sized bedrooms, including a primary bedroom with a vaulted ceiling and walk-in closet, along with a full bath. Conveniently located near Routes 8 and 44, Highland Lake, the Farmington River, shopping, restaurants, and outdoor recreation, this home offers comfortable, low-maintenance living in a great location. Schedule your private showing today! Association has scheduled deck replacement for later this year.

111 Riverton Road Unit 57, Winchester
$749,900
2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24192463 MLS
Year-round waterfront retreat with breathtaking sunrise views from one of the widest sections of the lake! This well-maintained 2-bedroom, 1 bath home offers comfortable living with a flexible loft area for additional sleeping space and a convenient half bath on the lake level. The updated kitchen and new windows provide modern comfort while showcasing expansive water views throughout the home. Outdoor amenities include a spacious waterfront patio, outdoor shower, and walk-in staircase for easy water access, making it ideal for swimming, boating, and relaxing lakeside. Adjacent to a state park, the property enjoys a picturesque setting with added privacy and natural surroundings. Move right in and enjoy as-is or update to suit your personal style. An additional parcel across the street is included, providing extra space and excellent long-term potential. Whether you're looking for a year-round residence, vacation getaway, or investment opportunity, this waterfront property offers an exceptional combination of location, views, and lifestyle.

812 W Wakefield Blvd, Winchester
$849,900
4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24191163 MLS
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 investment. Featuring modern upgrades throughout, the home boasts C/A, high-efficiency propane furnaces, newer appliances, windows, and siding-all designed for comfort and style. Inside, you'll find gorgeous details at every turn. The first-floor unit showcases a custom rustic kitchen with granite countertops, a Sub-Zero refrigerator, beverage fridge, gas range, and dishwasher. A luxurious marble-accented bathroom with a walk-in shower, two spacious bedrooms, and a large family room with French doors leading to a wraparound covered porch complete this level-perfect for soaking in those incredible views! The second-floor unit offers flexibility, featuring a kitchenette, dining room/office space, two additional bedrooms, and a family room with sliding doors opening to another covered porch-all with the same stunning lake vistas! Addt'l highlights include an oversized two-car detached garage with a carport, a hot tub (sold as-is), a level yard area, and a side deck. Situated just steps from the water, this home provides easy access to all lake activities. Rustic charm meets upscale living!

119 W Wakefield Blvd, Winchester
$849,900
4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24191186 MLS
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 investment. Featuring modern upgrades throughout, the home boasts C/A, high-efficiency propane furnaces, newer appliances, windows, and siding-all designed for comfort and style. Inside, you'll find gorgeous details at every turn. The first-floor unit showcases a custom rustic kitchen with granite countertops, a Sub-Zero refrigerator, beverage fridge, gas range, and dishwasher. A luxurious marble-accented bathroom with a walk-in shower, two spacious bedrooms, and a large family room with French doors leading to a wraparound covered porch complete this level-perfect for soaking in those incredible views! The second-floor unit offers flexibility, featuring a kitchenette, dining room/office space, two additional bedrooms, and a family room with sliding doors opening to another covered porch-all with the same stunning lake vistas! Addt'l highlights include an oversized two-car detached garage with a carport, a hot tub (sold as-is), a level yard area, and a side deck. Situated just steps from the water, this home provides easy access to all lake activities. Rustic charm meets upscale living!

119 W Wakefield Blvd, Winchester
$349,900
3 Baths ⋅ ACTIVE Status ⋅ 24191570 MLS
Flexible Commercial Building Medical * Office * Wellness * Redevelopment Opportunity 1 Lake Street presents a rare opportunity to acquire a highly adaptable commercial property in the heart of Winsted, Connecticut. Offering a flexible layout and strong potential for a variety of commercial uses, this property is well suited for owner-users, investors, medical professionals, and developers seeking a strategic location with long-term upside. The building can accommodate a wide range of permitted and potential uses, including: Medical and dental offices Outpatient healthcare services Professional office suites Physical therapy or rehabilitation facilities Fitness center or health club Wellness and specialty healthcare practices Educational or training facilities Community or nonprofit organizations The property's adaptable floor plan provides the flexibility to configure the space for a single occupant or multiple tenants, creating opportunities for both owner occupancy and income-producing investment. Situated near downtown Winsted, the property offers convenient access to local businesses, municipal services, and surrounding residential neighborhoods. Its accessible location and commercial setting make it an attractive destination for employees, patients, and customers.

1 Lake St, Winchester
$395,000
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24190347 MLS
Where Opportunity Meets Lifestyle! Unlock the potential of this exceptional mixed-use property located in the heart of downtown Winsted. Positioned on a bustling Main Street with excellent exposure and constant pedestrian traffic, this property is an outstanding opportunity for entrepreneurs, investors, or anyone looking to combine business ownership with residential living. The street-level commercial space is ready for its next chapter. Previously operating as a successful cafe, it includes a commercial kitchen setup with hood ventilation, refrigerator, restroom, and a spacious open layout that can easily accommodate a restaurant, coffee shop, boutique, salon, professional office, or countless other business concepts. Upstairs, you'll find a beautifully renovated three-bedroom apartment designed for modern comfort. Completely rebuilt down to the studs, the residence showcases a stylish new kitchen, updated windows, a newer roof, a private deck perfect for relaxing, and an energy-efficient on-demand hot water system. Separate gas and electric meters provide flexibility and convenience for owner-occupants or tenants alike. Just moments from Highland Lake, Route 44, shopping, dining, and all of Winsted's downtown attractions, this property offers incredible versatility. Live where you work, lease one or both units, or expand your investment portfolio with a property that offers excellent income-producing potential in a highly desirable location.

720 Main St, Winchester
$150,000
ACTIVE Status ⋅ 24188290 MLS
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 from beautiful Park Pond, you'll enjoy easy access to kayaking, canoeing, fishing, and peaceful days by the water. Surrounded by mature hardwoods, this serene setting offers exceptional privacy while being just minutes from the charming New England towns of Goshen and Norfolk, where you'll find farm-to-table dining, local shops, hiking trails, cultural attractions, and year-round outdoor recreation. Enjoy nearby skiing, state forests, lakes, and endless opportunities to explore the natural beauty that makes Litchfield County so desirable. The lot has been perk-tested, with well and septic to be installed. Whether you're dreaming of a modern country home, a luxurious weekend escape, or a peaceful year-round residence, this exceptional property offers the perfect blend of privacy, tranquility, and convenience. Best of all, the property is not located in a flood zone, so flood insurance is not required.

Ashley Rd Unit Lot 6, Winchester
$1,600,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24190733 MLS
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 the expansive patio, upper wraparound deck, front sunroom, and many windows throughout the home. The interior also offers numerous updates, including renovated kitchens and bathrooms, beautiful hardwood flooring, and an open-concept main living area with a cozy fireplace. The inviting layout provides the perfect setting for everyday living and entertaining. A finished lower-level studio apartment adds valuable versatility, offering ideal guest accommodations, a private retreat, home office space, or potential rental income opportunity. Don't miss this exceptional waterfront property offering the perfect blend of comfort, updates, and year-round lake enjoyment!

752 Lake Dr, Winchester
$369,900
4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24189288 MLS
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 bygone era. A welcoming foyer leads to the formal living room, formal dining room with pantry, spacious eat-in kitchen, comfortable family room, half bath, and convenient first-floor laundry. The living room features a fireplace that has been sealed but offers the potential to be restored, while the kitchen includes a flue for a wood stove for those who appreciate the warmth and ambiance of wood heat. The second floor offers five bedrooms and a full bath, with several layout possibilities to create a spacious primary suite. Above, the walk-up attic-offering several finished rooms along with additional expansion space (not included in the home's square footage)-provides endless possibilities for a home office, studio, recreation room, or additional living space. Additional amenities include natural gas heat, thermopane windows, and a roof that is approximately 15 years old. Victorian homes of this size and character are becoming increasingly difficult to find. A rare opportunity to own a true piece of architectural history.

70 Walnut St, Winchester
$1,600,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24187886 MLS
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 the expansive patio, upper wraparound deck, front sunroom, and many windows throughout the home. The interior also offers numerous updates, including renovated kitchens and bathrooms, beautiful hardwood flooring, and an open-concept main living area with a cozy fireplace. The inviting layout provides the perfect setting for everyday living and entertaining. A finished lower-level studio apartment adds valuable versatility, offering ideal guest accommodations, a private retreat, home office space, or potential rental income opportunity. Don't miss this exceptional waterfront property offering the perfect blend of comfort, updates, and year-round lake enjoyment!

752 Lake Dr, Winchester
$999,000
5 Baths ⋅ ACTIVE Status ⋅ 24134408 MLS
Rare opportunity to own a well-established, 38-year restaurant with a loyal, built-in clientele and strong community presence. This fully turnkey operation offers exceptional versatility and income potential, featuring a spacious dining area with seating for up to 156 guests, plus an upstairs 20-seat bar-ideal for expanding service or hosting private events. The property includes five apartments, with three currently functioning units and two additional units ready for completion-perfect for added value and increased revenue. A dedicated 12-15 car parking lot, along with ample street parking, ensures convenience for patrons and tenants alike. Guests can also enjoy outdoor dining with seating for approximately 24, enhancing the overall dining experience. The basement area is fully equipped for dough preparation and offers abundant storage, supporting full-scale catering capabilities and high-volume operations. Endless possibilities await with this unique investment-ideal for restaurateurs or investors seeking a thriving business with multiple income streams.

380 Main St, Winchester
$324,900
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24186089 MLS
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 bedroom, and a full bath w/laundry, providing the convenience of one-level living. Upstairs you'll find two additional bedrooms and a half bath. Lovingly cared for over the years, the home features central air conditioning, a standby generator, and a security system with fire and smoke monitoring for added comfort and peace of mind. Enjoy your morning coffee or evening relaxation on the covered deck overlooking the yard. Additional amenities include a one-car garage under the home and a location that offers the perfect balance of privacy and accessibility. A wonderful opportunity to own a move-in ready home in a convenient country setting.

103 Cordano Rd, Winchester
$579,900
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24185645 MLS
Welcome to 237 Wallens Hill Road, where comfort, quality, and exceptional entertaining spaces come together in a beautiful rural setting. This 9-room Colonial with a farmhouse front porch is set on .80 acres and offers 4 bedrooms and 2.5 baths. The main level features a formal dining room, large family room, mudroom, and an impressive eat-in kitchen with quartz countertops, stainless steel appliances, built-in microwave, stainless hood system, and a large center island with seating for four. A standout feature is the dedicated entertaining room complete with a custom walnut bar, kegerator, and a 5-foot stainless steel hood system over a built-in grill and flat-top griddle. Upstairs, the primary suite offers his-and-her closets and a beautiful full bath, while two additional bedrooms share a full bath. The fourth bedroom could also be used as an office, is located in the lower level. Additional features include hardwood floors throughout most rooms, multi-zone heat, central air conditioning with separate zones for the main and upper levels, a hybrid hot water heater, and a generator transfer switch. Step outside to enjoy a 14-foot pavilion on a stamped concrete and paver patio with a built-in fire pit, and spacious open backyard. Conveniently located near the Farmington River and Peoples State Forest, with easy access to hiking, fishing, kayaking, and other outdoor recreation while remaining close to shopping, dining, and everyday conveniences.

237 Wallens Hill Rd, Winchester
$389,900
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24184417 MLS
Welcome to East Lake Street at Highland Lake, where privacy, comfort, and lake living come together. Set back from the road on a private lot in the desirable First Bay area, this well-maintained lake-style home offers a quiet setting with seasonal lake views and refreshing breezes throughout. Offering 1,820 square feet, the home is listed as a 3-bedroom with a first-floor finished 4th room for added flexibility. The updated kitchen features quartz counter tops, stainless steel appliances, and ample cabinetry, with warm pine ceilings adding character throughout. Additional features include two full baths, first-floor laundry, newer windows, public water and sewer, natural gas, on-demand hot water, and a wood stove. Outside, enjoy a peaceful backyard garden and convenient rear access from Ontario Street. Located within one mile of local schools and a half mile of town, the home offers easy access to everyday amenities while maintaining a peaceful lake setting.

132 E Lake St, Winchester
$386,000
ACTIVE Status ⋅ 24182990 MLS
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, industrial, mixed-use, and residential uses, subject to local approvals. Rich in local history, the property was once part of the site of the famed American Knife Company, a cornerstone of Winsted's manufacturing heritage. Today, it presents a unique opportunity to transform a historic location into a new destination for manufacturing, business, housing, or investment. All public utilities, including water, sewer, natural gas, and electric, are available, providing a significant advantage for future development. The extensive road frontage offers excellent visibility, accessibility, and site design potential. Winsted is open for business and eager to work with developers, investors, and entrepreneurs to bring new projects to life. Whether your vision is commercial, residential, industrial, or a combination thereof, this property provides the location, infrastructure, and zoning flexibility to make it a reality. A rare offering with exceptional frontage, utility access, development potential, and historical significance.

00 Main St, Winchester
$250,000
ACTIVE Status ⋅ 24178092 MLS
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 natural beauty to the landscape. Established apple and peach trees, along with blackberry, raspberry, blueberry, and strawberry plants, make this property ideal for gardening, homesteading, or simply enjoying nature. Previously used as an apiary, the property is especially well-suited for beekeeping and pollinator-friendly use. Whether you are looking for recreational land, a future homestead site, or a peaceful natural retreat, this unique property offers endless possibilities.

321 Colebrook Rd, Winchester
$45,000
ACTIVE Status ⋅ 24179637 MLS
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 in the area (buyer to verify availability and connection requirements). Enjoy the convenience of nearby shopping, dining, recreation, and one of Northwestern Connecticut's most desirable lakes. Whether you're looking to build your dream home, a seasonal retreat, or an investment property, this lot offers outstanding potential. Be sure to discuss your plans with the towns Land Use and Development office.

32 Hubbard St, Winchester
$49,999
ACTIVE Status ⋅ 24177619 MLS
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 this lot

319 White Oak Trl, Winchester
$499,900
6 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24178149 MLS
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 rental income. With a current monthly gross income of $4,200, you can enjoy steady cash flow while benefiting from an increasingly competitive rental market. Located in a desirable neighborhood with public water and access to public sewer, this property is perfectly positioned to attract long-term tenants. Its proximity to local amenities, schools, and public transportation enhances its appeal, ensuring high occupancy demand. Each unit boasts separate electrical meters, providing tenants with individual control over their utilities. The common laundry facilities in the basement offer added convenience for residents, further enhancing the livability of the space. Recently paved parking enhances accessibility for both residents and guests, while dual heating units ensures comfort during colder months. This property is not only inviting but also functional, providing a hassle-free living experience for tenants. It also comes with established tenants, solid rental history, and a reliable mechanicals, allowing you to step into a well-oiled investment without the headaches of initial setup.

205 Old New Hartford Rd, Winchester
$795,000
ACTIVE Status ⋅ 24037015 MLS
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.

535, 538 W Wakefield Blvd, Winchester
$469,900
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24175936 MLS
Spacious 3 to 4 Bedroom Colonial Style Home on a 0.35 Acre Lot, plus located on a No Through Street. OPEN FLOOR PLAN. Beautifully Remodeled from "TOP TO BOTTOM" for Energy Efficient Living. Redesigned Country Style Kitchen offers Ample Cabinetry and includes New Oven/Range, Microwave, Refrigerator & Dishwasher.. 27' x 12' Living/Dining Combo with Bay/Bow Window that takes in Natural Light on those Sunny Days! Main Level Bath has Walk-In Shower. 3-Bedrooms on Second Floor includes New Full Bath. Staircase leads to Finished Attic offers potential as Loft, Bedroom, Office/Den. Recent Mechanical Upgrades includes Natural Gas Heating System, 200 Amp Electrical Service, Roof, Rebuilt Covered Porches, New Deck off of Kitchen. Finishing touches are being completed on the Rustic Style Detached Garage and 390 +/- Sq. Ft. Barn/Shed, along with Grounds Care. City Water & City Sewer.

9 Loomis St, Winchester
$269,900
2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24175908 MLS
Come enjoy Highland Lake living just in time for Summer. Relax in this one level living, cozy cottage home with views of the lake from your deck and just a short distance to Resha beach. Enter through a large mudroom to your open living room with large window to let in natural light, updated kitchen, 2 bedrooms, 1 full bath, main level laundry, front and rear deck, large yard & shed. New flooring throughout, new roof, HW heater is only 4 years old, vinyl siding & fire pit. Year round lake living.

147 E Wakefield Blvd, Winchester
$895,000
4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24172121 MLS
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, to the 12 over 12 Windows and Fireplaces, Displays the Charm & Character in this Residence! For a more Modern Twist, there is a Fully Remodeled Eat-in Kitchen with Quartz Counters, as well as Remodeled Bathrooms. 4 TO 5 Bedrooms, 3 Full Baths, Formal Dining Room & Comfortable Living Room. Spacious Sunken 20' x 21' Family Room with Cathedral Ceiling. Unique Loft offers a Birdseye View to the Family Room. Level 7 Acre Lot Enhanced by Stone Walls and Nice Plantings. Outbuildings include a 30' x 35' 4 Stall Horse Barn with Tack Room & Hayloft. 2 paddocks and a 25' X 30' Storage Building. Mechanicals include Oil Hot-Air Furnace, New propane heat in the sunken living room,200 AMP Electrical Service, Well Water & Septic System. A Quaint and Rural Atmosphere, but within Close Proximity to Major Shopping, access to State Parks, Lakes, Golf Courses, Ski Areas, and Local Arts and Cultural Venues. The Photo Library Partially tells the Story, but prospective Buyers need to Visit / Tour this Lovely Property in order to Appreciate its Attributes!!

469 Platt Hill Rd, Winchester
$200,000
ACTIVE Status ⋅ 24171867 MLS
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.

00 Chapel Rd, Winchester
$250,000
ACTIVE Status ⋅ 24170540 MLS
One-of-a-Kind Opportunity! Don't miss your chance to own this turnkey, award-winning restaurant in the heart of Litchfield County, perfectly situated in a high-traffic location.-Owner Financing Available! This 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 track record of success and a loyal customer base, this restaurant has earned recognition in top publications including the New York Times, Wall Street Journal, Hartford Courant, CT Magazine, and numerous local publications - Sale includes the business only (real estate excluded) and comes fully equipped with all infrastructure items. This is a rare opportunity to step into a thriving, reputable restaurant with an exceptional reputation-ready to operate from day one - Numerous infrastructure items are included in the sale totaling well over 100k (See list in attached docs)

436 Main St, Winchester
$239,000
7 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24169258 MLS
Brand new to the market. Must see large 2 story Colonial featuring 13 rooms, 7 Bedrooms, 3 Bathrooms, Walk up attic and full basement. Includes a 2 story barn. Convenient location in the heart of town lends itself to easy access to many nearby amenities. As an investment this residence also has great potential to convert to a multi family home or could be renovated for commercial office space. The possibilities are endless. The barn has the capability for multiple uses as well such as a workshop, studio, office, storage or to just park vehicles.

Winchester
$549,000
11 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 24166332 MLS
*PRICE REDUCTION* 150 Oak St. is a fully rented, rare, charming 1920's 5-family apartment home located in a beautiful residential neighborhood in Winsted/Winchester, CT. Old World charm with original woodwork, high ceilings, mostly hardwood floors, and hallways connecting the spacious rooms in 4 of the units -which feature 2 bedrooms and a dining room. The 5th floor is a 3-4 bedroom, 1 1/2 bath unit with electric H&HW. There is a 4-bay detached garage -some rented separately. 1 garage bay is rented to a non-tenant at $65/mo. A great investment opportunity! New since between 2021-2023: roof, 4 hot water heaters and 3 furnaces! Walking distance to Northwestern CT Community College and Downtown Winsted. Nearby shopping, indoor and outdoor activities. Easy commute to Rte 8 South and Rte 8 North to Western MA Pioneer Valley towns and the Berkshires. @ 25 miles to Rte 20 and Becket, MA. Several more miles on Rte 20 to the Lee Outlet and the MassPike!

150 Oak St, Winchester
$595,000
ACTIVE Status ⋅ 24165997 MLS
Property is visible from Route 44 (AKA Main St)and fronts on Willow St. and Case Ave. The facility has been an auto dealer, a boat dealer, and a storage facility. The building has a total of 12 overhead doors.

45 Willow St, Winchester

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.