Winchester CT Real Estate & Homes for Sale

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!!

Perfect property for a tiny home enthusiasts looking for easy maintenance-free living. Small lot, so no mowing. Economical gas heat. Although the property is one bedroom, the bedroom is upstairs and the downstairs is very large and open. There is a bathroom on the main level and a bathroom upstairs. Wood floors. Still some work to be done so come and make it yours.

ZONING IS TG Regulations are tailored to promote desired development patterns that promote an appropriate transition from rural to town uses. Certain uses are permitted, while others require a Special Permit. Nestled just minutes from Highland Lake and downtown Winchester, 9 Loomis Street presents an excellent opportunity for those seeking a fixer-upper with great potential. This colonial-style home offers 1,768 square feet of living space, featuring three bedrooms and two full bathrooms. The property is equipped with gas heating, providing efficient warmth throughout. Inside, you'll find hardwood floors throughout, adding character. The large kitchen is perfect for culinary enthusiasts, and the formal dining room, located off the kitchen, offers an ideal space for family meals or entertaining guests. Additionally, the walk-up attic and full basement provide ample storage or the potential for future expansion. The property sits on a spacious lot, complete with two sheds for additional storage. Its location near a gas station and auto repair shop adds convenience, while proximity to highway access ensures easy commuting. With its large yard and potential for customization, this home is ready to be transformed.

Charming 3-Bedroom Cape in Sought-After Lake Community. Welcome to this beautifully updated 3-bedroom, 2.5-bath Cape nestled in a vibrant lake community offering year-round fun! Enjoy boating, waterskiing, tubing, and all the perks of lake life just steps from your door, with serene water views to enjoy every day. The main level features a bright, inviting living room with hardwood floors and a custom wood-paneled accent wall that frames the propane wood stove, creating a warm and cozy focal point. The kitchen is updated with quartz countertops, stainless steel appliances, and a center island that opens into a casual dining area-perfect for entertaining or everyday meals. The flexible layout includes a main-level bedroom, while the second floor offers two additional bedrooms and an updated full bath. Downstairs, the finished basement provides extra living space ideal for a den, workout area, or home office. Step outside to your private backyard oasis-an expansive deck with a pergola and cabana, complete with a bar and outdoor TV setup, making it the ultimate spot for relaxing or entertaining after a day on the water. Whether you're looking for a full-time residence or a weekend retreat, this home offers the perfect blend of comfort, style, and lakefront living.

Welcome to your own private paradise! Nestled on an incredible 55 acres, this one-of-a-kind property offers peace, privacy, and the perfect blend of comfort and outdoor adventure. Featuring a ranch-style layout with 3 bedrooms and 2 full baths, this home is ideal for easy one-level living. Step inside to find hardwood floors throughout and three cozy fireplaces that bring warmth and character to every room. Recent upgrades include brand-new distribution boxes in the septic system, offering added peace of mind for years to come.The expansive grounds feature a detached 2-car garage and a massive 3-car detached garage with a loft, perfect for a workshop, studio, or storing equipment and outdoor toys. Enjoy the natural beauty of fruit trees, grape vines, and a peaceful gazebo, along with private trails for ATV riding and exploration. Surrounded by nature, this property offers the ultimate in seclusion, yet you're just minutes from downtown amenities, dining, and shopping. Whether you're dreaming of a serene homestead, a recreational retreat, or simply room to roam, this extraordinary estate is a rare and remarkable opportunity you won't want to miss.

UPDATED | SERENE | CHARMING | 2 LOTS | This Highland Lake retreat is ideal for the 1st time homeowner, getaway retreat or investment opportunity. Nestled in New England's natural beauty, you are sure to enjoy your lush surroundings & stunning views, truly a nature lovers delight. 3+ generous bedrooms, 2 full bathrooms, dining room, fireplaced living room, updated kitchen with stainless appliances, 1st flr laundry, plenty of parking & lake views. 2ND LOT: 461 E. Wakefield Blvd, Winsted (Additional Lot) to convey with purchase of 421 Unity Place. Property Card reads 2bed/1bath but is a 3bed/2bath. UPDATES INCLUDE: Newer Roof ('24), flooring, paint, energy efficient windows, kitchen, bathrooms and MORE! LOCATION: public lake access w/Resha Beach, 4min. away & Holland Beach (boat launch, 7min. away. Platt Hill State Park (78 acres of outdoor activities), 10 min. away. Steven's Reserve of the Winchester Land Trust.**Buyers must do their research if choosing this property as an investment opportunity

Situated on a private road with views of Highland Lake, this beautifully updated home offers a perfect blend of modern comfort and quiet surroundings. Boasting a brand-new roof, siding, windows, as well as new front and back porches this home is ready to go for anyone looking for a great home. Step inside to discover an inviting, light-filled interior with contemporary finishes throughout. The spacious kitchen is perfect for cooking and entertaining, and finished basement for additional space This home includes private water access for residents on Mathew Rd as well as a public beach only a short walk from the front door. Basement living area will be added to overall living space once permit is closed.

This spacious 5-bedroom, 2-bath Colonial offers incredible flexibility and room to grow. The first floor features a large eat-in kitchen, a sun-filled dining room with a charming brick hearth fireplace, a massive family room, two bedrooms, and a full bath with laundry. Upstairs you'll find three generously sized bedrooms and a freshly painted second full bath. Set on a nice lot with a newer septic system (installed approx. 2022), this home has great bones and the space you've been looking for. Some updates and personal touches will make it shine. Not eligible for FHA financing due to some exterior condition items. Audio/video recording devices are in use on the property. Professional pictures to be uploaded. Being sold As-Is.

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!

Welcome to this charming four-bedroom antique home that is beautifully renovated to blend timeless character with modern comforts. As you step inside you'll be greeted by the warmth of refinished hardwood floors and an inviting living room featuring a cozy fireplace and built-in bookcases perfect for relaxing or entertaining. The heart of the home is the brand-new kitchen boasting sleek granite countertops, stainless steel appliances and plenty of cabinet space for all your culinary needs. The adjacent dining room is ideal for gatherings or hosting guests. This home offers three fully remodeled bathrooms each showcasing contemporary finishes and thoughtful design. A new second-floor laundry room adds convenience to daily living keeping chores organized and easily accessible. For added versatility, the property includes an in-law apartment providing privacy and comfort for extended guests. Additional upgrades include a new boiler, energy-efficient windows, a new roof and a modern engineered septic system ensuring the home is both efficient and well-maintained. Outside, enjoy the tranquility of a spacious four-acre lot complete with a patio for outdoor dining and relaxation. The large barn with three bays offers ample space for car storage, hobbies, or potential workshop use. With its perfect blend of antique charm and modern updates this home is truly a rare find. Don't miss your chance to experience the best of both worlds.

Welcome to this beautifully renovated home, nicely tucked away in historic Winsted. This lovely property features over 2,200 square feet of gross interior living space. The large kitchen, dining, and living room areas provide a seamless flow, perfect for entertaining. The home boasts four spacious bedrooms and one and a half baths. The beautifully renovated attic adds even more charm and functionality to the space. Additional highlights include modern stainless steel appliances, with all appliances included, and hardwood flooring throughout the home. The beautifully landscaped yard creates a perfect outdoor space for relaxation and gatherings. Conveniently located near local amenities, this home provides easy access to shopping, dining, and more. Experience this beautiful home firsthand Don't miss the opportunity to make this move-in ready gem your new home.

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.

A charming house located 2 blocks from highland lake. This 3 bedroom, 1 large full bath is move-in ready. The dining room has a beautiful built in, the 3 large windows allowing for natural light to brighten the room. Off of the dining room is a nice family room. The kitchen is large and spacious and off the kitchen in the back is a lovely sunroom with a fireplace (natural gas) that has sliders that lead to the deck and the back yard. The laundry room is located on the first floor, the 3 bedrooms upstairs have hard wood floors as well the downstairs with the exception of the kitchen.

Lakefront Historic Architecture meets Modern Styling on private waterfront penninsula with 360' direct lake frontage! Split timber tudor architecture offers unique features - leaded glass, stone flooring, window seats, paneling and mouldings, brick and stone appointments. A stunning kitchen for folks who cook, charming diningroom with bar and window seat overlooking the waterfront, and spacious family room with granite fireplace with views in all directions. Sunroom with radiant heated stone flooring, extensive stone patios, pergola, gardens, terraces, sandy beach/swimming area. This is it!

Welcome to this spectacular Highland Lake estate, offering a unique blend of luxury & tranquility. Situated on 1.3 acres of level land, the property includes a large barn/garage capable of housing multiple cars, boats, & equipment. The main home boasts generously sized rooms w/ high ceilings, offering an open, airy feel throughout. The kitchen has been updated w/ hardwood cabinets, featuring updated appliances, a spacious eat-in area, & an oversized island perfect for meal prep & entertaining. The rest of the main floor is ideal for hosting guests, w/ expansive windows providing stunning views of Highland Lake from every angle. Step outside to a covered front porch, where you can take in breathtaking sunrise views over the water. The second floor is home to the huge Primary bedroom, complete w/ a recently remodeled full bath & two walk-in closets. Four additional spacious bedrooms share Jack & Jill bathrooms, & a second-floor summer porch offers a serene spot to enjoy the natural beauty of the lake. The third floor adds even more space, w/ three additional bedrooms & a full bath that could be updated to reflect your needs. Directly on the lake is a 1/4 acre lot w/ 150+/- ft of water frontage, you'll find a charming lakeside cottage that features a cozy fireplace, kitchenette, full bath, & wrap-around deck. Whether you're relaxing on the dock or enjoying the cottage's amenities, this entire property is perfect for experiencing the best of lakefront living.

Welcome to a piece of history with this enchanting Cape farmhouse, a true gem nestled in the picturesque town of Winchester. Built in 1830, this home radiates classic charm with its original details and timeless character. The property features two inviting fireplaces, perfect for cozy evenings, and an oversized country kitchen that offers ample space for culinary creativity and family gatherings. The living room exudes warmth and charm, making it an ideal space for relaxation, while the cozy dining room provides a welcoming setting for meals with loved ones. With three bedrooms, this home offers comfortable living spaces that maintain its historical allure. The magnificent and private 13-acre lot presents a rare opportunity for renovation, expansion, or even subdivision. Whether you envision restoring the farmhouse to its former glory, expanding to create your dream estate, or exploring the potential for development, the possibilities are endless. Don't miss out on this unique chance to own a piece of Winchester's history and make it your own. This charming farmhouse is not just a home; it's a canvas for your dreams. Act quickly-opportunities like this are truly one of a kind.

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.

Build your DREAM home! Largest lot available on the lake with great views and parking! Will build to suite. Don't miss this wonderful opportunity! WELL IS LOT CORNER at Forest Ave FRONTAGES ARE MARKED IN RED. +-a2 map and topo in documents.

Welcome to Strong Island, a waterfront retreat on Highland Lake. The clean waters of Highland Lake in the town of Winchester in Litchfield County surround this 1.6 acres island. History abounds for this property as the original house dates back to 1890. There were significant alterations made in 1920 that added several rooms, a boat house, a barn and porch. Babe Ruth made several trips to Strong Island for his weekends and vacations away from NYC. Strong Island is one of the largest islands on Highland Lake and has the best views. The position of this island give it the longest view of the lake on a North view and also on an Easterly view. The position of the main house on the island, the various docks, piers and out buildings make this property unable to be duplicated today. Strong Island is a trophy property that needs some polishing, but incredible in so many ways.

Beautiful custom built gem situated on a private site with a stream! Bright, sunny open floor plan with 3 bedrooms, 2.5 baths, great bonus room. Gleaming hardwood floors thru-out, granite tops, stone/marble baths, walk up attic. Large deck off kitchen. Don't miss this incredible opportunity!