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$325,000
4 Beds ⋅ 3 Baths ⋅ 24199882 MLS
Investment Opportunity! Well-maintained two-family house offering the ideal combination of functionality and income potential. Each unit features 5 rooms, including 2 bedrooms and 1 full bath. Enjoy the benefits of a convenient downtown location, close to schools, shopping, dining, and everyday conveniences. Both units are currently rented, making this property a strong choice for investors seeking steady cash flow.

48 Center St, Winchester
$324,900
4 Beds ⋅ 2 Baths ⋅ 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
$319,900
2 Beds ⋅ 1 Baths ⋅ 24200816 MLS
New Construction - Easy to Maintain - Open Floor Plan - Central Air - Vinyl Plank flooring throughout. White Shaker Kitchen with Island and granite countertops. All stainless steel kitchen appliances. Separate laundry room on main level. Glass paneled door to covered deck off the living room area. Two spacious bedrooms with large closets. Entry foyer with large walkin closet Large heated garage with area for a work space. Garage door opener, Paved driveway. Room dimensions are approximate.

14 Bank St, Winchester
$309,900
2 Beds ⋅ 2 Baths ⋅ 24201146 MLS
Welcome home to this beautifully maintained 2bedroom Cape offering the perfect blend of comfort, character, and modern updates. Set in a soughtafter neighborhood, this property delivers movein readiness with valuable improvements already completed. (New roof and electric panel). Step inside to find a bright, inviting living space featuring wood floors, updated kitchen, a cozy fireplace, and skylights that fill the home with natural light. The layout includes one full bath on both levels providing convenience for everyday living. There is a possibility to make a 1st floor bedroom if needed. Outside, enjoy a fully fenced backyard complete with a shed and a cabana-ideal for storage, hobbies, or relaxing outdoor gatherings. The property also features a 1car attached garage plus a carport.

94 Colony Dr, Winchester
$305,000
3 Beds ⋅ 2 Baths ⋅ 24186089 MLS
Back on the market due to buyers inability to secure financing. Well-maintained Cape in a desirable rural setting, yet just minutes from shopping, dining, schools, and other everyday conveniences. This 7-room home offers 3 bedrooms and 1.5 baths with a flexible floor plan designed for comfortable living. The main level features a formal living room, dining room, kitchen, family room, primary 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. Back on the market due to buyers inability to secure financing

103 Cordano Rd, Winchester
$304,900
2 Beds ⋅ 2 Baths ⋅ 24201785 MLS
Enjoy beautiful water views and access to Highland Lake from this inviting home offering comfortable living spaces and desirable features throughout. The main level features a galley kitchen with plentiful white cabinetry, laminate flooring, refrigerator, dishwasher, and electric range. A convenient powder room and stackable washer add functionality. The spacious living room/dining area features wide-plank wood flooring, a small dining area, and a walk-out porch leading to a Trex deck-perfect for enjoying the outdoors and water views. A small first-floor bedroom offers flexibility for guests, an office, or additional living space. Upstairs, the primary bedroom is generously sized to easily accommodate a king-size bed and features wood flooring and propane-fired baseboard heat. The second bedroom also offers wood flooring, a large closet, ceiling fan, two large windows, and propane-fired baseboard heat. The full bathroom includes a newer vanity, stall shower, and laminate tile flooring. Additional features include forced-air propane heating on the main level, window air-conditioning units, a carpeted stairway, and two off-street parking spaces. A boat launch on Highland Lake provides an exceptional opportunity to enjoy boating and waterfront recreation.Book a showing today. This property will not last!

325 E Wakefield Blvd, Winchester
$295,000
170078080 MLS
WINCHESTER CREST 51 acres of forested gently rolling land sited upland in Winchester Center. There is a former homesite and multiple choices for additional homesites affording complete privacy. There is abundant wildlife, trails, intermittent streams, dense and sparse forest. Perfect for year round home site, weekend retreat or recreational land.

393 Winchester Rd, Winchester
$289,000
2 Beds ⋅ 1 Baths ⋅ 24202928 MLS
Welcome to this relaxing seasonal cottage, situated high above road level and offering breathtaking panoramic views of the 444-acre Highland Lake. Enter through the oversized screened porch, where you can unwind with family or friends while taking in the beautiful perennial plantings and natural surroundings. This charming cottage features two bedrooms, a loft, one full bath, an open-concept kitchen, dining area, and living room. For your comfort, oil heat and a mini-split unit provide heat and air conditioning. Additionally, there's a rear deck area perfect for outdoor dining & grilling. An extra outdoor shower is available to refresh after spending time on the lake.

347 W Wakefield Blvd, Winchester
$260,000
3 Beds ⋅ 2 Baths ⋅ 24204964 MLS
This charming historic home, built in 1860, blends timeless character with thoughtful updates. Featuring 3-4 bedrooms, this property offers flexible living space to meet your needs. The beautifully remodeled upstairs bathroom is a standout feature, offering modern comfort within this classic home. Enjoy your LARGE eat-in kitchen with laundry hook ups and plenty of natural lighting and ample amounts of storage. The home sits on a flat, level yard with a huge storage shed, perfect for outdoor gatherings, storage, gardening, and play. Multiple decks off the home create inviting spaces to relax and take in the surroundings. Located just moments from a local boat launch, this property is ideal for those who love recreational water access. You're also close to the town green, shops, and everyday conveniences, making this home the perfect blend of historic charm and modern lifestyle. Schedule to view today!!

118 Meadow St, Winchester
$250,000
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
$250,000
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
$239,986
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
$239,000
7 Beds ⋅ 3 Baths ⋅ 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
$200,000
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
$199,000
3 Beds ⋅ 1 Baths ⋅ 24206541 MLS
Welcome to 416 Horne Ave, a charming 3-bedroom, 1-bath home offering approximately 1,056 square feet of comfortable living space in Winsted. Built in 1979 and situated on approximately 0.29 acres, this property offers a practical layout with room to make it your own. The home provides a welcoming setting for everyday living, with three bedrooms offering flexibility for family, guests, a home office, or hobbies. Enjoy the convenience of a residential location close to local amenities, schools, shopping, dining, and outdoor recreation. An excellent opportunity for homeowners or investors seeking value in the Winsted community.

416 Horne Ave, Winchester
$150,000
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
$69,000
24143845 MLS
Well-maintained second-floor office condo in excellent condition, offering a versatile and efficient layout for a variety of professional uses. The space features three private offices, a generous bullpen area that can accommodate 4-6 desks, and ample storage throughout. The property offers ample parking, making it convenient for both staff and clients. Located just minutes from downtown, the building is home to a strong mix of professional neighbors, including an eye doctor, dentist, civil engineering firm, and attorney-an ideal setting for any business seeking a convenient and professional environment.

140 Willow St Unit STE 6, Winchester
$45,000
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
$37,900
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

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