Winchester Homes for Sale

Welcome to Winchester, Connecticut—a hidden gem nestled in Litchfield County, where charming landscapes meet a tight-knit community. This picturesque town is known for its lush greenery, serene lakes, and a rich tapestry of history, making it an idyllic setting for families, retirees, and anyone seeking a tranquil lifestyle.

Winchester boasts a unique blend of rural charm and modern conveniences. With a population that values community spirit, residents enjoy a variety of local events, farmers' markets, and recreational activities. The town is home to the stunning Highland Lake, perfect for boating, fishing, and picnicking, while the surrounding parks and nature trails invite you to explore the great outdoors year-round.

For those considering a move to this enchanting area, you'll find a diverse selection of homes for sale that cater to various tastes and budgets. From cozy single-family homes with expansive yards to charming historic properties that exude character, Winchester offers something for everyone. Many homes are situated in peaceful neighborhoods, providing a safe environment for children and pets alike.

The real estate market in Winchester reflects the town's appeal, with properties that often feature modern amenities while retaining their original charm. Whether you're looking for a starter home or a serene retreat, you'll discover that Winchester's real estate options are as inviting as the town itself.

Join a community that celebrates both its heritage and its future. Explore the homes for sale in Winchester, CT, and take the first step toward making this beautiful town your new home!

Newest Winchester Homes for Sale

$749,900

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24206406 MLS

Welcome to 180 Shore Dr - your own beautifully renovated waterfront retreat on highly desirable Lake! This exceptional year-round home offers the perfect combination of modern comfort, stunning water views, and the lake lifestyle you've been dreaming about. Featuring 3 bedrooms and 2 full bathrooms, the home has been extensively remodeled with quality finishes and thoughtful attention to detail throughout. Step inside to a bright, inviting interior filled with natural light from newer Andersen windows and doors. The beautifully renovated kitchen features modern appliances, sleek countertops, abundant cabinetry, and an open, welcoming feel that's perfect for entertaining after a day on the lake. Both full bathrooms have been tastefully remodeled, while LifeProof luxury plank flooring provides durability and easy maintenance. Enjoy year-round comfort with updated heating and central air conditioning. Outside is where this property truly shines! A newer deck and patio overlook Highland Lake, creating the perfect setting for morning coffee, summer dinners, sunsets, and unforgettable gatherings with family and friends. Step outside and enjoy direct access to one of Connecticut's most beautiful recreational lakes. Whether you're searching for a primary residence, weekend escape, or spectacular AirBnB, 180 Shore Dr delivers the lifestyle, location, and views that make waterfront ownership so special. Don't just buy a home - start living the Highland Lake lifestyle!

180 Shore Dr, Winchester

$450,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24204002 MLS

Bring your horses home! There's something special about country living-stepping outside with your coffee, seeing your horses grazing, hearing the chickens scratching around, and having a little more room to simply enjoy life. 130 Riverton Road offers the space and setting to create the country lifestyle you've been hoping of. A two-stall run-in shed is already in place for your horses, with plenty of room to add fencing, gardens, chickens, and your own finishing touches. The home is ready for your vision-come bring your animals, your ideas, and make this little piece of country your own.

130 Riverton Rd, Winchester

$289,000

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 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

$439,900

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 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

$319,900

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 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

$629,900

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24199152 MLS

Enjoy the best of Highland Lake living with this unique property offering a spacious home directly across the street from the lake along with your own separate waterfront parcel! The main house features 7 rooms, 3-4 bedrooms and 2 full baths, providing plenty of space for year-round living or a relaxing lake retreat. A deck overlooking the waterfront offers the perfect spot to enjoy the lake views, while a wonderful outdoor gathering area featuring a stone fireplace provides an ideal setting for entertaining family and friends. Just across the street, your private waterfront parcel takes lake living to another level with a 15' x 29' deck overlooking Highland Lake and a dock for your boat. Also located on the waterfront is a 240 sq. ft. structure with a half bath, offering excellent flexibility for storage, a lakeside retreat or additional sleeping accommodations. Spend your days boating, swimming, fishing or simply relaxing by the water, then retreat to the comfort of your home just steps away. A rare opportunity to enjoy your own private waterfront access and all that beautiful Highland Lake has to offer!

837 E Wakefield Blvd, Winchester

$309,900

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 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

$319,900

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 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

$600,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 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

$649,900

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24198153 MLS

Nestled along the coveted east shore of Highland Lake, 600 East Wakefield Boulevard presents a rare opportunity to own a piece of one of Connecticut's most sought-after waterfront communities. Filled with charm and character, this lakeside property offers the perfect canvas to create a custom retreat that reflects your vision and lifestyle. Spend your days swimming, boating, kayaking, and enjoying all that Highland Lake has to offer, with easy lake access and a nearby semi-private boat launch. As evening arrives, breathtaking panoramic sunsets paint the water, creating an unforgettable backdrop for lakeside living. What truly sets this property apart is that, unlike many waterfront homes and open parcels around the lake, it benefits from both a DEEP PRIVATE WELL and PUBLIC SEWER service, offering convenience, reliability, and added value that are increasingly difficult to find. Whether you're seeking a seasonal getaway, YEAR-ROUND waterfront residence, or renovation opportunity, this exceptional property is ready for its next chapter. With waterfront opportunities on Highland Lake becoming increasingly scarce, this is your chance to secure a truly unique lakefront setting. Subject to Probate Court approval. Property sold as-is.

600 E Wakefield Blvd, Winchester

$399,900

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24196702 MLS

Well-maintained 4-bedroom Colonial tucked away on a quiet dead-end street. This inviting home features a newly renovated eat-in kitchen with updated cabinetry, countertops, and finishes, perfect for everyday living and gathering. The comfortable layout includes a spacious living room and dining area, while four bedrooms offer flexibility for family, guests, or a home office. Enjoy the large yard, a back deck with a Sunsetter awning for shaded outdoor living, and a charming enclosed front porch. A generator adds peace of mind. Conveniently located close to town, shopping, and everyday amenities, this move-in-ready home offers both comfort and convenience.

122 Standard Ave, Winchester

$849,900

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 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

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