Winchester Real Estate

Welcome to Winchester, a charming town nestled in Litchfield County, Connecticut. Winchester offers a perfect blend of small-town charm and natural beauty, making it an ideal place to call home.

Located in the scenic northwest corner of Connecticut, Winchester boasts picturesque views of rolling hills, lush forests, and sparkling lakes. Outdoor enthusiasts will appreciate the abundance of recreational opportunities, from hiking and biking along scenic trails to fishing and boating on the pristine waters of Highland Lake.

Winchester is also rich in history and culture, with historic buildings, museums, and art galleries dotting the town. Explore the Winchester Historical Society Museum to learn about the town's fascinating past, or browse local art galleries to discover the work of talented local artists.

In Winchester, you'll find a tight-knit community that values a high quality of life. The town is known for its excellent schools, safe neighborhoods, and vibrant local economy. Whether you're looking to raise a family or enjoy a peaceful retirement, Winchester offers a welcoming and friendly atmosphere for residents of all ages.

With its stunning natural scenery, rich history, and strong sense of community, Winchester is a place where you can truly feel at home. Come discover all that this charming town has to offer and find your perfect piece of paradise in Litchfield County, Connecticut.

Newest Listings in Winchester

$449,000

3 Beds ⋅ 3 Baths ⋅ 24208283 MLS

Enjoy lake living with this inviting 3 bedroom, two and a half bath home located directly across the street from Highland Lake. Offering water views and a convenient location, this property is a wonderful opportunity for a year round residence or weekend getaway. The home features a two car garage and plenty of parking and storage. Enjoy the convenience of having two beaches and a boat launch within walking distance, making it easy to spend your days swimming, boating, fishing, or simply relaxing by the water. Come take a look!

150 E Lake St, Winchester

$489,000

3 Beds ⋅ 2 Baths ⋅ 24206936 MLS

Originally built in 1940, this charming Cape has been completely transformed-taken down to the studs and thoughtfully renovated from top to bottom, blending classic character with the comfort and style of a modern home. The inviting open floor plan features a gorgeous kitchen with a large center island, granite countertops and stainless-steel appliances, flowing seamlessly into the spacious living area. The main-level primary suite is a true retreat with its own fireplace and private full bath. A convenient laundry room completes the first floor. Upstairs, you'll find two generously sized bedrooms and a beautifully updated full bath. The renovated lower level provides additional usable space and includes a garage bay under the house. Adding even more versatility is a detached two-car garage equipped with heating and air conditioning-ideal for a workshop, hobby space, car enthusiast or additional storage set in a peaceful location with a park directly across the street, this beautifully reimagined home offers the charm of a 1940 Cape with the extensive updates and functionality today's buyers are looking for. Truly move-in ready and a must-see!

50 Palmer Ave, Winchester

$425,000

3 Beds ⋅ 2 Baths ⋅ 24198146 MLS

Situated on a side street just outside the town, this contemporary 3-bedroom residence exudes an open and spacious ambiance, enhanced by vaulted ceilings that impart a sense of grandeur to the living room. The home features numerous updates, including a stunning kitchen, two living areas, a separate dining space, and two decks accessible from both the dining and living rooms. The first-floor laundry room is convenient and adjacent to the half bath. The upper level comprises three bedrooms and a full bath. Additionally, a finished lower level and an attached garage complete this home's layout. This Winchester property offers a private yard and a convenient location, placing you in the heart of Litchfield County.

120 Moore Ave, Winchester

$350,000

4 Beds ⋅ 2 Baths ⋅ 24207462 MLS

3.7-acre property offering a 4-bedroom, 2-bath Cape with plenty of room and flexibility. Formerly operated as a small farm, the property provides space for gardening, animals, recreation, or other uses. The first floor features an open floor plan with impressive 10-foot ceilings and a layout that can adapt to a variety of needs. Four bedrooms provide room for family, guests, or a home office. A unique opportunity for buyers looking for acreage, space, and the ability to make a property their own.

100 Norfolk Rd, Winchester

$260,000

3 Beds ⋅ 2 Baths ⋅ 24204964 MLS

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 and ample amounts of storage. The home sits on a flat, level yard with a huge storage shed, perfect for outdoor gatherings, storage, gardening, and 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!!

118 Meadow St, Winchester

$595,900

8 Beds ⋅ 5 Baths ⋅ 24200869 MLS

One of the finest grand classic Colonial homes where timeless charm and beautiful details can still be found throughout. Features include elegant crown molding, rich wood paneling, wide baseboard molding, gleaming hardwood floors, and a sweeping grand staircase-all adding to the warmth and character of this truly special home. This home features formal dining room, sitting room with fireplace, remolded kitchen offering two sinks, granite counter large palladium windows allowing in natural light a main floor study with fireplace /built in bookshelves. On second floor are 6 bedrooms and 3 full baths, primary bedroom has unique alcove with sink /dressing area. Vintage Blue stone patio is for quiet times to enjoy watching the wildlife, or you can play a game of billiards on the standard size table in the game room. Only three families have lived in this elegant 101 year young home. A home filled with elegance, history and warmth All this elegance can be yours. Wonderful home for extended family or possible Bed & Breakfast. There is many possibilities with this property. Minutes from Rt 8, easy drive to Bradley Airport, enjoy recreation at Highland lake.

143 Holabird Ave, Winchester

$199,000

3 Beds ⋅ 1 Baths ⋅ 24206541 MLS

Welcome to 416 Horne Ave, a charming 3-bedroom, 1-bath home offering approximately 1,056 square feet of comfortable living space in Winsted. Built in 1979 and situated on approximately 0.29 acres, this property offers a practical layout with room to make it your own. The home provides a welcoming setting for everyday living, with three bedrooms offering flexibility for family, guests, a home office, or hobbies. Enjoy the convenience of a residential location close to local amenities, schools, shopping, dining, and outdoor recreation. An excellent opportunity for homeowners or investors seeking value in the Winsted community.

416 Horne Ave, Winchester

$339,900

2 Beds ⋅ 2 Baths ⋅ 24206905 MLS

Private Country Living on 16 Acres! Enjoy the peace and privacy of this charming ranch nestled on expansive acreage, offering the feel of a true country compound. Features include 2 bedrooms, a family room with fireplace, kitchen, three-season enclosed porch, heated possible office, and large deck. Plenty of cleared land surrounds the homesite while mature trees provide exceptional privacy. Possible subdivision potential adds even more opportunity. Buyer to verify with the town. A rare opportunity for those seeking space, privacy, and endless possibilities!

320 Colebrook Rd, Winchester

$749,900

3 Beds ⋅ 2 Baths ⋅ 24206406 MLS

Highest and best offer by noon on Monday 21st. 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.

180 Shore Dr, Winchester

$359,900

4 Beds ⋅ 2 Baths ⋅ 24206509 MLS

Discover this versatile two-family residence offering a blend of modern updates and timeless charm. Each unit boasts three bedrooms and a full bath, providing ample space and comfort for tenants or multi-generational living. Both units have been beautifully renovated, featuring a brand-new kitchen with stylish finishes, updated bath, gleaming hardwood floors, and plush new carpet in the bedrooms. This level offers a fresh, move-in-ready appeal that renters or owners will love.

77 Hubbard St, Winchester

$299,900

5 Beds ⋅ 2 Baths ⋅ 24206151 MLS

Well-maintained two-family home offering excellent owner-occupant or investment potential. First-floor unit features 3 bedrooms, kitchen, and living room and is currently rented. Second-floor unit is vacant and offers 2 bedrooms, living room, and kitchen. Separate utilities and laundry for each unit. Full basement provides additional storage. Entire home has undergone lead remediation. Great opportunity to live in one unit while generating rental income.

18 Pratt St, Winchester

$850,000

24196886 MLS

An exceptional opportunity to create your dream home on the shores of highly sought-after Highland Lake. This waterfront property at 414 E Wakefield Boulevard offers the perfect setting to bring your vision of lakefront living to life. Existing plans for an impressive approximately 4,000-square-foot waterfront home are available, giving you the option to move forward with an already thoughtfully designed residence-or start fresh and create a custom home uniquely your own. Imagine walls of glass framing spectacular lake views, expansive outdoor living spaces, and your own private waterfront just steps from your door. Whether you envision a sophisticated year-round residence or an unforgettable family lake retreat, this property offers the rare opportunity to design around the lifestyle you've always wanted. You have the location. You have the lake. Now create the dream.

414 E Wakefield Blvd, Winchester

Start Your Search

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.