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$959,900
2 Beds 2 Baths 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

$749,900
2 Beds 1 Baths 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 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

$353,500
3 Beds 2 Baths 24190790 MLS
Please submit your client's highest and best offer by Sunday 07/19 at 3:00 PM. Beautifully remodeled and move-in ready, 195 Reaching Hill Rd in Winsted, CT features modern updates, comfort, and functionality throughout. This 3-bedroom, 2-bath conventional-style home sits on nearly one acre of land and showcases a bright open-concept layout with beautiful hardwood floors, a spacious living area, and a dedicated dining space with large sliding glass doors overlooking the backyard. The main floor includes a bedroom and full bathroom, providing flexibility for a variety of uses such as a guest room, home office, or convenient one-level living arrangement. The finished lower level with a walk-out entrance and full basement adds valuable additional space with endless possibilities for a recreation room, home gym, playroom, workshop, or additional storage. Enjoy the comfort of central air conditioning, along with a relaxing porch, outdoor shed, and a private backyard with plenty of space to relax, garden, or entertain. Located near Highland Lake, this property provides convenient access to outdoor recreation throughout the seasons. With thoughtful renovations, spacious rooms, and a great indoor-outdoor connection, this home is ready for its next owner. Schedule your private showing today and see everything this beautifully updated Winsted property has to provide.

195 Reaching Hill Rd, Winchester

$369,900
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

$1,600,000
4 Beds 3 Baths 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

$679,900
3 Beds 3 Baths 24186150 MLS
Custom built log Home!This home sits on a 3 acre, private landscaped lot with mountains laurel and a park nearby. This sprawling home with a covered front porch(28x 8)is perfect for relaxing and features over 1100 sq of decking which wraps around the house for entertaining. The Home features a stunning living room with interior balcony, chandeliers, field stone wood fireplace, cathedral ceiling, and sliders to a deck.The kitchen has a breakfast bar, stainless steel appliances and a pizza oven. It's opened to a dining room with a scenic view. The 1st floor primary bedroom suite has a cathedral ceiling, wood floors,2 walk in closets, one is cedar lined, the bath features a whirlpool tub and full shower, marble sink, tile floor and vaulted ceiling.Open the sliders from the bedroom to enjoy views from a 4 season sunroom.There is a 2nd bedroom on the main level and a 2nd full bath. Upstairs there is bedroom ,a 1/2 bath ,plus a Den (used as a bedroom).The lower level features a family room and a fieldstone wood fireplace .The full basement has a laundry room,utility room, storage, and a workshop.The oversized 2 car garage has a wood stove, and a 1000 gallon oil tank. All windows are energy efficient with krypton argon gas. The solar panels are lease at $68 a month.The large shed has electric and concrete floor .It's a short drive to great fishing, hiking ,swimming,skiing, town,shopping, restaurants, theaters, entertainment, festivals and vineyards. Enjoy Litchfield County.

426 Platt Hill Rd, Winchester

$324,900
3 Beds 2 Baths 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

$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

$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

$389,900
3 Beds 2 Baths 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

$349,000
3 Beds 2 Baths 24177410 MLS
Peaceful country living with unlimited potential! Nestled on a quiet Winsted street, this three bedroom, two bathroom ranch sits on nearly 2 acres of private, setback land. It offers excellant structural bones and a functonal layout, making it an ideal candidate for a rewarding renovation project. The large living and dining space features high cathedral ceilings and exposed wood beams with the focal point of the living room being a floor to ceiling fireplace equipped with a wood stove insert. Convenient one-level living at it's best! A two car attached garage leads to a breezeway room, ideal for a home office or studio. The home requires updates throughout and is being sold strictly "as is." The price of this property reflects its current condition, offering a solid foundation to buyers looking to customize a home.

107 Roberts Ave, Winchester

$469,900
3 Beds 2 Baths 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

$124,900
2 Beds 1 Baths 24174996 MLS
Exceptional opportunity to build near one of Northwest Connecticut's most desirable lake communities. Just steps from beautiful Highland Lake, this water-view parcel offers the chance to create your dream home in a setting that combines lake lifestyle, natural beauty, and convenient access to some of Litchfield County's most sought-after destinations. Highland Lake is a true Connecticut gem-a picturesque, natural lake in historic Winchester, spanning approximately 444-445 acres, about three miles long, with three distinct bays and depths reaching approximately 63 feet. Known for boating, fishing, swimming, and year-round enjoyment, Highland Lake has long been treasured for its scenic shoreline, established lake community, and recreational appeal. The lake is also recognized by Connecticut DEEP with a public boat launch and boating regulations, further supporting its active recreational use. The location is equally compelling: enjoy the peaceful feel of a classic Litchfield County lake setting while remaining convenient to Salisbury, Lakeville, Norfolk, Torrington, and downtown Winsted. Hartford is roughly 40 minutes away by car, making this an ideal retreat without sacrificing accessibility.

624 Wynne Rd, Winchester

$765,000
3 Beds 3 Baths 24173895 MLS
Beautiful Private Brick/Clapboard Tudor set back on 8.46 private acres (which includes an extra 2+ acre abutting lot). New Hand Split Cedar Shingled Roof and new rebuilt brick chimney set off this custom elegant home. All warm cherry wood floors and special custom moldings throughout the home add charm. Classy center island Kit with new subzero, granite counters & bow window-Fireplaced Dining room opens to large back deck overlooking fenced in private backyard-Massive sunken fireplaced living room -1st floor office-Private fireplaced Family room-huge master suite with fireplaced sitting room,walk-in closet & thermo-spa master bath. Large upper level bonus room with cozy private office-CAIR& whole house generator system are pluses-Beautiful professionally landscaped private level yard add lasting ambiance to this special home

184 Smith Hill Rd, Winchester

$895,000
4 Beds 2 Baths 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

$679,000
4 Beds 4 Baths 24159801 MLS
PRICE REDUCTION !! Discover unparalleled Highland Lake living with this exceptional 1.00-acre retreat, boasting 50 feet of direct lake frontage and a newly renovated dock/deck. Enjoy breathtaking water views from your sunroom, dining room, and multiple bedrooms within this versatile 4/5 bedroom home. A unique first-floor suite with a separate exterior entrance offers ideal flexibility as a main-floor master or in-law accommodation. The upper-level primary suite boasts a private balcony perfect for savoring morning coffee while overlooking the shimmering lake. Entertain effortlessly in the large private backyard space, complete with an expansive 2 tier deck and built-in fire pit. Recent major upgrades ensure worry free enjoyment, including a high-efficiency HVAC (2024), new roof (2022), new siding, exterior doors, added insulation, two remodeled baths, full interior paint, and newer carpet throughout. Extensive landscaping has been completed, including new front railings, leveling and removal of several large trees. Previously a successful Airbnb, this property offers abundant parking, a two-car garage, and dual laundry facilities. Embrace all seasons on Highland Lake - from summer boating and fishing, lake is stocked with trout and bass for fishing enthusiasts, to winter ice skating/fishing. Your lakeside dream awaits!

121 W Wakefield Blvd, Winchester

$1,850,000
9 Beds 6 Baths 24159989 MLS
Live the Highland Lake Dream - 431 W. Wakefield Blvd, Winchester, CT Summer is just around the corner - and in Winsted, resort living never ends. Recently named one of the most desirable towns to live in, with the breathtaking Highland Lake at its heart, Winchester offers the perfect blend of beauty and lifestyle. This waterfront estate at 431 W. Wakefield Blvd isn't just a home - it's your gateway to the ultimate lake life. Wake each morning to panoramic water views, and step outside to a world of four-season recreation. In summer, enjoy boating, jet skiing, swimming, and fishing right from your private dock, or simply relax by the shoreline. When winter arrives, the lake transforms into your own frozen wonderland for ice fishing, skating, and fireside gatherings. Inside, luxury awaits. The main home features gourmet finishes, a chef's kitchen, and custom craftsmanship throughout. A charming guest bungalow offers privacy for family, friends, or guests. Zoned for a bed and breakfast, and featuring an extra subdividable lot, the property offers immense potential - whether as a private retreat, an upscale B&B, or an investment in future development. Set on 425 feet of pristine water frontage, this estate captures the essence of Highland Lake living - natural beauty, year-round recreation, and endless opportunity.

431 W Wakefield Blvd, Winchester

$449,000
5 Beds 4 Baths 24071827 MLS
Timeless Victorian with Endless Possibilities.Step into a piece of history with this stunning Victorian property, a landmark in the community and home to The Maloney Funeral Home since the early 1900's. Nestled in the TCR Zone, this versatile building offers a wealth of potential. The TCR Zone allows for accessory residential uses, community centers, family day care homes, single-family dwellings, and home farming. Additionally, with a special permit, the property may accommodate a variety of uses, including affordable housing, bed and breakfasts, boarding houses, congregate residences, convalescent/nursing homes, country inns, home occupations, mixed-use buildings, multi-family dwellings, outdoor private recreation and entertainment facilities, restaurants, schools, two-family dwellings, and places of worship. The first floor features spacious rooms that could accommodate a kitchen, pantry, dining room, formal living room, family room, and office. The second floor provides ample space for four to five bedrooms, while the third floor boasts a generously sized apartment, adding flexibility to the layout. A standout feature is the impressive 2,300 sq. ft. three-story barn/garage, offering abundant storage, workshop space, and potential for various uses. Whether you're seeking a unique investment opportunity or a property brimming with character, this exceptional offering is ready for its next chapter.

55 Walnut St, Winchester

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