Perched atop a scenic hill overlooking picturesque Highland Lake, this charming ranch offers 1,051+/- square feet of inviting living space with two bedrooms and two full bathrooms. The galley-style kitchen features Thomasville cabinetry and Corian countertops, opening to an intimate dining room with tranquil lake views. Take your pick of relaxing spaces-whether it's the cozy living room with an exposed beam, the airy sunroom overlooking the water, or the expansive 12x17 Trex deck. You can also unwind in the outdoor hot tub beneath the cabana for year-round enjoyment. Adding to its appeal, this property includes a private boat dock and picnic area, offering direct access to all the recreation Highland Lake provides. Whether you're seeking a vacation getaway or a forever home, this lakeside retreat is truly a must-see.
Bring your vision to this spacious 6-bedroom, 2.5-bath home full of character and potential. Featuring a newer roof and boiler, this property offers peace of mind while leaving room for your personal touch. Enjoy the classic Victorian details and generous layout, perfect for creating your dream home. Situated on a sidewalk-lined street just steps from downtown eateries, a local brewery, and minutes to Highland Lake for outdoor recreation. Off-street parking adds convenience. Don't miss this opportunity to own a piece of history in a vibrant location-schedule your showing today!
Beautifully renovated 1870 Colonial offering 1,172 sq. ft. of updated and functional living space. The home features hardwood floors in the living room and both bedrooms, adding warmth and durability throughout. A convenient first-floor bedroom provides flexibility, while the spacious primary bedroom is located on the second level. The kitchen has been completely refreshed with new flooring, skylights that bring in excellent natural light, an eat-in area, and all-new stainless steel appliances. The first-floor laundry room adds everyday convenience and includes a remodeled half bath. The full bathroom has also been fully updated with modern finishes. Fresh interior paint and all-new lighting help create a clean, move-in-ready environment. Major updates include a new gas furnace, new vinyl siding, new roof on the addition, new wood front porch, and a new deck, offering long-term value and reduced maintenance for the next owner. Conveniently located near shopping, restaurants, major highways and Highland Lake, this home combines charm with modern improvements in a highly accessible location. A great option for buyers seeking a fully renovated home with nothing left to do but move in.
Turnkey 3 Bedroom, 1 bathroom home on almost an acre in Winchester. The home is sited up a long driveway in a quiet, wooded setting across from state land. Completely renovated by current owner, top to bottom. Updated kitchen & bath, new roof, new hot water heater, new Trex deck, new pellet stove, new ductless mini splits in living area and primary bedroom and much more! Attached one car garage and shed. Must see! Minutes from Burr Pond State Park for hiking & swimming and Highland Lake, a popular recreation destination. Sale contingent on seller finding and securing suitable housing.
Discover a low maintenance and hassle-free alternative to condo living with this easy-to-maintain, single-family home , perfect for investors, first-time buyers, or anyone seeking simplified living without the burden of HOA fees. Step inside to an efficient layout featuring brand-new WREN kitchen cabinets, granite countertops, a new gas stove, and a new refrigerator, offering a fresh and modern cooking space. The carpet (installed in 2024) has been well maintained, and the home includes a hot water heater installed in 2022 for added peace of mind. Recent major updates include a new roof installed in 2023 with a 15-year transferable warranty, providing long-term value and security. Outside, the small property size means minimal upkeep-ideal for busy lifestyles or turnkey rental potential. Enjoy the convenience of being within walking distance to Main Street, giving you easy access to shops, dining, and community amenities.
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. The home sits on a flat, level yard, perfect for outdoor gatherings, gardening, or 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!!
Stunning Contemporary Home on a Quiet Corner Lot. This unique home offers a beautifully updated open floor plan that seamlessly blends the kitchen, dining, and living areas-perfect for modern living and entertaining. The kitchen features granite countertops, ample cabinetry, stainless steel appliances, and great flow into the main living space. The first floor includes a refinished half bathroom and a spacious laundry room with a walk-in shower-ideal for dog washing, in-law convenience, or added accessibility. A cozy den/family room with a fireplace provides the perfect spot to relax. Upstairs, you'll find three bedrooms including a generous primary suite with a large walk-in closet and en-suite bathroom. Additional full bathroom on the second level offers comfort and convenience for family or guests. The basement has been professionally waterproofed offering the potential for future finishing. Situated on a corner lot of two dead-end streets, this property offers exceptional privacy in a quiet, desirable neighborhood. Truly a must-see home combining modern updates with unique style and comfort. This one will not last!
Welcome to 187 Torringford Rd! Set on a beautiful 4-acre lot, this spacious 4-bedroom home offers the perfect blend of natural light, character, and country living. Step inside through the mudroom, also serving as a convenient laundry area, and head up to a charming loft that overlooks the bright, window filled kitchen. The kitchen features an abundance of natural light and provides a warm, inviting space for cooking and gathering. Adjacent to the kitchen is a cozy breakfast nook with a bay window, opening seamlessly into the living room for easy everyday living. Across the hall, you'll find a generous family room and a separate dining room, offering plenty of room for entertaining and hosting holidays. A half bath completes the main level. Upstairs are four bedrooms, creating flexible options for family, guests, or office space. Outside, the property truly shines with a two-story garage/barn featuring a loft, perfect for storage, a workshop, or hobby space. Enjoy summer days in the above-ground pool. Appreciate new 5 year old roof. The 4-acre lot provides both open, usable yard space and lightly wooded areas, ideal for gardens, animals, recreation, or simply soaking in the peaceful surroundings. This charming property offers privacy, potential, and the opportunity to make it your own. Schedule your showing today!
Welcome to this Wonderful Historic Colonial Farmhouse.. This home has been lovingly remodeled with many of the original features still intact. This home offers a large kitchen with newer counters open to the dining area and is complete with a fireplace. Living room is generous sized, it's filled with light, exposed beams and hardwood floor. On this level you'll also find 2 bedrooms and a fully remodeled bath. As well as a extra large Mudroom with laundry hookups and wide boards floors...You'll gain access to the upper floor VIA a gorgeous open staircase, and there you'll find the Large primary bedroom with walkin closet and sitting area. On this level you'll find another bedroom and a full bathroom which also has been remodeled with walkin shower and a beautiful claw foot tub. There is second staircase also... Throughout this home you'll find gleaming hardwood floors, original hand hewn beams, newer windows, vinyl siding, generator ready, well pump, and newer hot water heaters (one gas, one electric) There's a 2 car detached garage with electric, outdoor shower, above ground pool (needs liner) and 2 sheds and the sweetest little porch to enjoy your free time.. All set on 1.85acreas. This is truly a country setting with easy access to highways, to get you to any major city you may need including Hartford, Boston, or NYC..Come see it now.. Being Sold As-IS .. Subject to probate approval.
Welcome to your cozy cottage retreat in beautiful Highland Lake Community. Views of the lake from deck, public beach right around the corner. Step inside to a large mudroom, open living room, updated kitchen, 2 bedrooms, 1 full bath & laundry all on one level. New flooring and paint throughout. New roof, HW heater only 4 years old, vinyl siding, large yard with fire pit and shed. Year round lake living.
Discover the charm of this spacious contemporary Cape, set on a peaceful one-acre lot in a desirable rural neighborhood. Offering over 3,000 square feet of living space, this well-maintained home provides a flexible layout ideal for today's lifestyle. The main level features a formal living room, dining room, updated kitchen, den, sunroom with fireplace and hot tub, full bath, and convenient laundry area. From the kitchen and sunroom, step out to a private rear deck perfect for relaxing or entertaining. Upstairs you'll find three comfortable bedrooms and a full bath. The lower level offers an additional 1,000 square feet of finished space - an ideal area for gatherings, hobbies, or a recreation room, along with a separate home office. Car enthusiasts and hobbyists will appreciate the impressive garage space, complete with its own heat and air conditioning. Recent updates within the past five years include the kitchen, garage A/C, and driveway, with additional improvements such as newer windows, baths, and hardwood floors. The roof on both the home and barn was replaced just two years ago. The barn provides great additional storage and versatility. A unique property combining space, function, and rural tranquility for the outdoor enthusiasts - come see all that 197 Spencer Hill Road has to offer!
Distinctive Country Estate with Two Homes on 9.6 Rolling Acres Set amid 9.6 picturesque country acres, this unique property offers two homes and endless potential. The stone and stucco main residence features eight spacious rooms, including four bedrooms and four fireplaces, blending classic character with old-world charm. Rolling open land and mature trees surround the home, providing an ideal setting for a private country retreat, family compound, or restoration project. The detached 843 sq. ft., two-story guest house adds exceptional versatility-perfect for extended family, rental income, or a studio/workshop.P Restoration to the main house would include a new heating system, bathroom updates, fresh painting, and roof repair, offering an excellent opportunity to create a stunning showcase estate tailored to your taste. A rare find with remarkable potential-bring your vision and transform this classic country property into a timeless treasure.
TO SETTLE ESTATE: Available for Immediate Occupancy is this Immaculate 3 to 4 Bedroom Colonial tucked away on a quiet street. Features Hardwood Floors throughout the house, 24' x 14' Family Room with Propane Gas Stove, Country Kitchen. Primary Bedroom with it's own office area. Oversized Full Bath. 3-Season 21' x 8' Enclosed Porch. 26' x 10' Concrete Patio. Detached One Car Garage. Attractive Park-Like Landscaped Grounds. Off Street Parking for 6 Vehicles. City Water and Sewer. All Kitchen Appliance as well as Washer & Dryer remain with the property. Close Proximity to Town Center for General Shopping, Medical, Variety of Food Venues. "MOVE-IN CONDITION".
Discover the ease of condo living with the charm of a riverside retreat at Riverwalk Condos. This beautifully cared-for 2-bedroom, 1.5-bath home offers an inviting layout designed for comfort and relaxation. The spacious living room with its warm fireplace opens to a private deck overlooking the Still River-an ideal spot to unwind at the end of the day or entertain with a view. The kitchen also connects to the deck, making indoor-outdoor living a breeze. Upstairs, two comfortable bedrooms provide plenty of space for rest and retreat.The two-car garage under the unit offers convenience and extra storage. With mailboxes just across the street and every detail in excellent condition, this condo blends everyday practicality with a serene natural backdrop.
Welcome to lake living at its finest! Built in 2014 and first time on the market. Impeccably maintained, this stunning three bedroom, 3 bath home on Highland Lake, Winchester offers the perfect blend of comfort, style, and breathtaking VIEWS! From the moment you enter you will be captivated by the open-concept design, high-end finishes and panoramic lake views from both inside and out. Enjoy effortless indoor-outdoor living with a walkout lower level leading to a covered patio, hot tub and your own private dock-already in place and ready for summer fun. The two-car attached garage, basement storage and workshop, location off main road and numerous upgrades add convenience and value. Whether you're watching the sunrise or sunset, relaxing by the water, or entertaining friends and family, this home offers year-round vacation vibes and in immaculate condition. A rare opportunity on one of Connecticut's most desirable lakes-don't miss it!
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!
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, 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!!
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!
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.
LOCAL NEWS JUST ANNOUNCED THAT WINSTED WAS 1 OF THE MOST DESIRABLE TOWNS TO LIVE WITH EMPHASIS ON BEAUTIFUL HIGHLAND LAKE. 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.

Winchester is located in Connecticut. Winchester, Connecticut has a population of 10,335. Winchester is less family-centric than the surrounding county with 20.73% of the households containing married families with children. The county average for households married with children is 26.17%.
The median household income in Winchester, Connecticut is $65,537. The median household income for the surrounding county is $84,797 compared to the national median of $69,021. The median age of people living in Winchester is 50.7 years.
The average high temperature in July is 80.7 degrees, with an average low temperature in January of 13.6 degrees. The average rainfall is approximately 52.3 inches per year, with 52.6 inches of snow per year.