Winchester Real Estate

Welcome to Winchester, Connecticut – a hidden gem nestled in the heart of Litchfield County. This picturesque town, steeped in history and natural beauty, offers a perfect blend of small-town charm and modern convenience. With its serene lakes, lush forests, and rolling hills, Winchester is a haven for outdoor enthusiasts and families alike.

At the center of the community lies the stunning Lake Winchester, a popular destination for swimming, fishing, and boating during the warm summer months. The surrounding parks and nature trails provide ample opportunities for hiking, biking, and enjoying the breathtaking scenery that each season brings. Whether you're taking a leisurely stroll through the quaint downtown area or exploring the expansive parks, the natural beauty of Winchester is sure to captivate you.

Winchester boasts a rich historical background, with landmarks that tell the story of its past. The town is home to several charming historical buildings, including the elegant Winchester Center and the iconic Town Hall, which reflect the architectural beauty of yesteryear. The local community is warm and welcoming, with a vibrant calendar of events that bring residents together throughout the year, from farmers' markets to seasonal festivals.

For families, Winchester offers a strong sense of community and excellent educational opportunities, with well-regarded schools that prioritize student success. With its convenient location just a short drive from larger cities, residents enjoy the peace of suburban living while still having easy access to urban amenities.

Discover the unique allure of Winchester, CT – where history, nature, and community come together to create an idyllic place to call home.

Newest Listings in Winchester

$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

$359,900

6 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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

ACTIVE Status ⋅ 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

$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

$325,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24199882 MLS

Investment Opportunity! Well-maintained two-family house offering the ideal combination of functionality and income potential. Each unit features 5 rooms, including 2 bedrooms and 1 full bath. Enjoy the benefits of a convenient downtown location, close to schools, shopping, dining, and everyday conveniences. Both units are currently rented, making this property a strong choice for investors seeking steady cash flow.

48 Center St, 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

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