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$799,900
2 Beds 1 Baths 24195283 MLS
Experience an everyday vacation at 804 W. Wakefield Blvd on beautiful Highland Lake! This exceptional turnkey, year-round waterfront retreat is ideal as a primary residence, weekend escape, vacation home, or income-producing rental. Perfectly positioned on the widest part of Highland Lake's coveted Third Bay, enjoy breathtaking sunrises, panoramic water views, and bald eagles soaring overhead from your expansive lakeside deck. With over $100,000 in owner upgrades, this move-in ready home offers effortless lakefront living with a newer roof, owned solar panels, updated systems, a permanent grandfathered dock, seawall, outdoor shower, firepit, and direct access to motorboating, kayaking, paddleboarding, swimming, and outstanding fishing. A rare additional 0.24-acre lot across the street provides a total of 5 parking spaces perfect for family and guests. Enjoy easy access to Route 8, a short drive to Bradley International Airport, and year-round recreation with nearby Ski Sundown, Butternut Ski Area, scenic hiking trails, wineries, breweries, restaurants, and charming New England towns. This is your opportunity to own one of Highland Lake's most desirable waterfront homes-simply unpack, relax, and make every day feel like a vacation.

804 W Wakefield Blvd, Winchester

$649,900
24104099 MLS
Development Opportunity! 41.23 Acres with Historic Home & Barn - Subdivision Possible Rare chance to own a prime 41.23-acre parcel in New England with an 1800 Antique Colonial Farmhouse and classic English/New England hybrid barn. The land may be subdividable and is located near the highly desirable Riverwalk Condominiums, making it ideal for new condo development (subject to approvals). The home and barns are in need of complete renovations to be brought back to its original beauty. Endless possibilities: equestrian facility, hunting lodge, glamping, corporate retreat, B&B, resort, spa, farming, or wedding venue. Home requires full renovation. Property offers a mix of open fields, wooded areas, and historic charm in a peaceful, private setting. Bring your ideas and breathe new life into this timeless estate!

115 Old Robertsville Rd, Winchester

$600,000
4 Beds 3 Baths 24200204 MLS
Welcome to this beautifully crafted 3,486 sq. ft. Colonial, offering exceptional quality, thoughtful design, and plenty of space both inside and out. Set privately on 2.03 acres at the end of a long driveway, this 10-room home was built in 2007 and has been meticulously maintained. The main level features gleaming hardwood floors, a spacious family room with fireplace, and an incredible gourmet kitchen designed for both everyday living and entertaining. The first-floor primary suite provides convenience and privacy, while the additional bedrooms offer plenty of room for family and guests. Upstairs, a massive play/recreation room provides endless possibilities for entertaining, hobbies, or additional living space. A huge walk-up attic offers abundant storage and future potential. The oversized two-car garage provides plenty of room for vehicles, equipment, and storage. Central air conditioning adds year-round comfort. Enjoy the perfect balance of privacy and convenience, with hiking, fishing, and area ski destinations nearby, while still being just a short distance from shopping, dining, and commuting routes. Extremely well built with quality throughout, this exceptional home is a pleasure to show and ready to welcome its next owner.

205 Wallens St, Winchester

$579,900
4 Beds 3 Baths 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

$495,000
4 Beds 3 Baths 24185819 MLS
Unique opportunity to own this spacious 4-bedroom Colonial set on 27 acres in Winchester, CT. Previously home to animals, this property offers endless possibilities for hobby farming, equestrian pursuits, recreation, or simply enjoying the privacy and beauty of the countryside. Ideally located directly across the street from Green Woods Country Club, you'll enjoy convenient access to golf, and beautiful scenic views right at your doorstep. Inside, you'll find an expansive kitchen featuring abundant cabinetry, gas cooktop, double ovens, generous counter space, and plenty of room for family and friends to gather. The main level offers a formal dining room, a large family room, and a welcoming living room with a fireplace and direct access to the back deck, perfect for outdoor dining and entertaining on warm summer evenings. The walk-out lower level provides excellent potential for additional finished living space and already includes a bar area, making it ideal for a future recreation room, home gym, or media space. With its combination of acreage, functionality, and room to grow, this property presents a rare opportunity to create the lifestyle you've been dreaming of. Conveniently located with easy access to dining, shopping, recreational amenities, and major commuter routes, this property offers the perfect balance of peaceful country living and everyday convenience.

293 Torringford St, Winchester

$474,900
5 Beds 3 Baths 24178677 MLS
Tucked away on 2.09 private acres in the desirable Platt Hill area of Winchester, this custom-built contemporary offers the perfect blend of architectural character, space, and recent updates. With over 3,400 square feet, 5 bedrooms, 3 full baths, and a 2-car garage, this home provides flexibility for everyday living, entertaining, or multi-generational needs. Inside, you'll find a thoughtfully designed layout with an open, airy feel, highlighted by hardwood floors in the living room, two fireplaces, and abundant natural light throughout. The spacious main living areas offer the ideal balance of openness and comfort, creating inviting spaces to gather while still maintaining warmth and definition. Major improvements including a newer roof and windows provide peace of mind, while the expansive yard offers endless possibilities for outdoor enjoyment, recreation, gardening, or simply enjoying the privacy and natural surroundings. A rare opportunity to own a distinctive contemporary home with room to grow in one of Winchester's most scenic settings.

441 Platt Hill Rd, Winchester

$439,900
4 Beds 2 Baths 24202969 MLS
Welcome to 136 Losaw Rd! Built in 1984, this nicely maintained and updated home offers 1,977 sq. ft. of living space with 4 bedrooms, 2 full baths, and a comfortable open floor plan, all set on 1.76 acres. The main living level features an open dining area and kitchen with breakfast bar overlooking the sunken living room, highlighted by a beautiful arched fieldstone fireplace with propane log set. Two modest-sized bedrooms and a full bath complete this level. Upstairs, you'll find two generously sized bedrooms, a second full bath, and a large storage closet. The lower level features a fieldstone hearth and approximately 400 sq. ft. of additional space ready to be finished to suit your needs. Outside, the property offers a two-stall horse barn with additional room for hay and storage, adding great versatility for equestrian use, hobbies, or additional storage. Nicely maintained and thoughtfully updated over the years, this property offers plenty of space both inside and out. Don't let this one slip away!

136 Losaw Rd, Winchester

$349,900
3 Baths 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

$324,900
4 Beds 2 Baths 24199721 MLS
Well-maintained two-family home offering spacious apartments, separate utilities, and a convenient location within walking distance to downtown amenities. The first-floor apartment features approximately 1,620 sq. ft. with a kitchen, living room, dining room, full bath, and 2-3 bedrooms. The second-floor apartment offers approximately 1,424 sq. ft. with a similar layout including a kitchen, living room, dining room, full bath, and 2-3 bedrooms. Each unit is serviced by its own efficient natural gas boiler and hot water and features a covered porch for additional outdoor living space. Situated on a generous .56-acre lot, the property also includes a two-story barn offering excellent storage and additional possibilities. A nicely maintained property with spacious units and a desirable location close to shopping, restaurants, and other downtown conveniences. An excellent opportunity for an owner-occupant or investor.

50 High St, Winchester

$172,500
2 Beds 2 Baths 24201953 MLS Stillriver Commons BLDG.
Move right into this beautifully updated 2-bedroom, 1.5-bath townhouse tucked away in a small, quiet community with a peaceful setting overlooking the Still River. The thoughtfully updated interior features a renovated kitchen with newer appliances, smart thermostats, fresh paint, and newer flooring throughout. The full bath has also been refreshed with a newly updated shower and new plumbing. The spacious living room offers oversized sliders that open to a paved, private patio-an ideal spot to relax and enjoy the tranquil river views. Additional features include a private garage with a storage room and an assigned parking space. Conveniently located with easy access to Route 8, grocery stores, and downtown Winsted, while also putting you close to Highland Lake, West Hill Lake, the Farmington River, and numerous hiking trails. A wonderful opportunity to enjoy low-maintenance living in a peaceful setting while staying close to everything you need!

21 Riveredge Dr Unit 21, Winchester

$45,000
24179755 MLS
Rare opportunity to build your dream home on this 1.07-acre vacant lot conveniently located close to downtown shopping, dining, and everyday amenities. Situated in an established neighborhood, this property offers season-long westerly views and spectacular sunset vistas, creating the perfect backdrop for your future home. Public water and public sewer are available in the street (buyer to verify availability and connection requirements). Buyers are encouraged to discuss their building plans with the Town's Land Use and Development Department to determine potential uses and requirements. Whether you're planning a year-round residence or a custom-designed retreat, this property offers an excellent combination of location, views, and potential.

132 Florence St, Winchester

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