Winchester Homes with Colonial Style

Welcome to Winchester, Connecticut – a charming town nestled in the picturesque Litchfield County. Known for its serene landscapes and rich history, Winchester offers a delightful blend of rural charm and modern amenities. With its stunning lakes, lush forests, and vibrant community, this town is an ideal place for families, retirees, and anyone looking to embrace the beauty of New England living.

One of the standout features of Winchester is its variety of architectural styles, particularly the classic Colonial homes that grace its streets. These homes, characterized by their symmetrical facades, gabled roofs, and elegant columns, exude timeless charm and sophistication. With spacious layouts and often set on generous lots, Colonial-style homes provide ample room for families to grow and thrive. Imagine hosting gatherings in expansive living areas, preparing meals in well-appointed kitchens, and enjoying quiet evenings on picturesque porches.

Winchester's Colonial homes not only offer aesthetic appeal but also reflect the town’s rich history, providing a glimpse into its past while accommodating modern lifestyles. The community is known for its friendly atmosphere, excellent schools, and a plethora of recreational activities, from hiking and fishing to community events that foster connection among residents.

Whether you’re drawn to the historical significance of Colonial architecture or the natural beauty surrounding Winchester, this town promises a fulfilling lifestyle. Discover the perfect Colonial home in Winchester, where history meets contemporary living in a community that feels like home. Your dream home awaits in this enchanting corner of Connecticut!

Newest Winchester Homes with Colonial Style

$959,900

2 Beds ⋅ 2 Baths ⋅ COMING SOON Status ⋅ 24194765 MLS

Exceptional Highland Lake waterfront Colonial rebuilt in 1996 to modern standards and codes, offering quality construction and timeless appeal. Perfectly positioned with 58 feet of direct northwest-facing waterfront, this home is designed to capture breathtaking lake views from nearly every angle. The spacious living/great room features a dramatic fieldstone fireplace and walls of glass with multiple sliders leading to a large wraparound waterfront deck, creating a seamless connection between indoor and outdoor living. The beautiful oak kitchen is highlighted by quartz countertops, newer stainless steel appliances, and an open layout that flows effortlessly into the main living areas, making it ideal for entertaining. Upstairs, the primary bedroom boasts soaring 12-foot cathedral ceilings and an abundance of windows overlooking the lake, providing a spectacular place to wake up each morning. Outside, the waterfront has been thoughtfully improved with an updated seawall that includes an aluminum dock, making it easy to enjoy boating, swimming, fishing. Highland Lake is a pristine 444-acre lake renowned for its clean water. Conveniently located just 45 minutes from Hartford and Bradley International Airport, and within easy reach of the Berkshires, Infinity Music Hall, the Warner Theatre, New York City, and Boston, this property offers the perfect blend of year-round living and a weekend retreat. A rare opportunity to create a lifetime of memories.

204 E Wakefield Blvd, 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

$1,600,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24187886 MLS

Experience the best of lakefront living with breathtaking views, spectacular sunsets, and exceptional outdoor spaces. This amazing waterfront home features a brand-new 100' x 14' Brazilian hardwood deck, a 35' x 6' stationary Trex and steel dock, and a private cabana-perfect for relaxing, boating, swimming, and entertaining. Soak in panoramic water views from multiple vantage points, including the expansive patio, upper wraparound deck, front sunroom, and many windows throughout the home. The interior also offers numerous updates, including renovated kitchens and bathrooms, beautiful hardwood flooring, and an open-concept main living area with a cozy fireplace. The inviting layout provides the perfect setting for everyday living and entertaining. A finished lower-level studio apartment adds valuable versatility, offering ideal guest accommodations, a private retreat, home office space, or potential rental income opportunity. Don't miss this exceptional waterfront property offering the perfect blend of comfort, updates, and year-round lake enjoyment!

752 Lake Dr, Winchester

$579,900

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24185645 MLS

Welcome to 237 Wallens Hill Road, where comfort, quality, and exceptional entertaining spaces come together in a beautiful rural setting. This 9-room Colonial with a farmhouse front porch is set on .80 acres and offers 4 bedrooms and 2.5 baths. The main level features a formal dining room, large family room, mudroom, and an impressive eat-in kitchen with quartz countertops, stainless steel appliances, built-in microwave, stainless hood system, and a large center island with seating for four. A standout feature is the dedicated entertaining room complete with a custom walnut bar, kegerator, and a 5-foot stainless steel hood system over a built-in grill and flat-top griddle. Upstairs, the primary suite offers his-and-her closets and a beautiful full bath, while two additional bedrooms share a full bath. The fourth bedroom could also be used as an office, is located in the lower level. Additional features include hardwood floors throughout most rooms, multi-zone heat, central air conditioning with separate zones for the main and upper levels, a hybrid hot water heater, and a generator transfer switch. Step outside to enjoy a 14-foot pavilion on a stamped concrete and paver patio with a built-in fire pit, and spacious open backyard. Conveniently located near the Farmington River and Peoples State Forest, with easy access to hiking, fishing, kayaking, and other outdoor recreation while remaining close to shopping, dining, and everyday conveniences.

237 Wallens Hill Rd, Winchester

$469,900

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24175936 MLS

Spacious 3 to 4 Bedroom Colonial Style Home on a 0.35 Acre Lot, plus located on a No Through Street. OPEN FLOOR PLAN. Beautifully Remodeled from "TOP TO BOTTOM" for Energy Efficient Living. Redesigned Country Style Kitchen offers Ample Cabinetry and includes New Oven/Range, Microwave, Refrigerator & Dishwasher.. 27' x 12' Living/Dining Combo with Bay/Bow Window that takes in Natural Light on those Sunny Days! Main Level Bath has Walk-In Shower. 3-Bedrooms on Second Floor includes New Full Bath. Staircase leads to Finished Attic offers potential as Loft, Bedroom, Office/Den. Recent Mechanical Upgrades includes Natural Gas Heating System, 200 Amp Electrical Service, Roof, Rebuilt Covered Porches, New Deck off of Kitchen. Finishing touches are being completed on the Rustic Style Detached Garage and 390 +/- Sq. Ft. Barn/Shed, along with Grounds Care. City Water & City Sewer.

9 Loomis St, Winchester

$895,000

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24172121 MLS

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, New propane heat in the sunken living room,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!!

469 Platt Hill Rd, Winchester

$239,000

7 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24169258 MLS

Brand new to the market. Must see large 2 story Colonial featuring 13 rooms, 7 Bedrooms, 3 Bathrooms, Walk up attic and full basement. Includes a 2 story barn. Convenient location in the heart of town lends itself to easy access to many nearby amenities. As an investment this residence also has great potential to convert to a multi family home or could be renovated for commercial office space. The possibilities are endless. The barn has the capability for multiple uses as well such as a workshop, studio, office, storage or to just park vehicles.

Winchester

$1,850,000

9 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 24159989 MLS

Live the Highland Lake Dream - 431 W. Wakefield Blvd, Winchester, CT Summer is just around the corner - and in Winsted, resort living never ends. Recently named one of the most desirable towns to live in, with the breathtaking Highland Lake at its heart, Winchester offers the perfect blend of beauty and lifestyle. This waterfront estate at 431 W. Wakefield Blvd isn't just a home - it's your gateway to the ultimate lake life. Wake each morning to panoramic water views, and step outside to a world of four-season recreation. In summer, enjoy boating, jet skiing, swimming, and fishing right from your private dock, or simply relax by the shoreline. When winter arrives, the lake transforms into your own frozen wonderland for ice fishing, skating, and fireside gatherings. Inside, luxury awaits. The main home features gourmet finishes, a chef's kitchen, and custom craftsmanship throughout. A charming guest bungalow offers privacy for family, friends, or guests. Zoned for a bed and breakfast, and featuring an extra subdividable lot, the property offers immense potential - whether as a private retreat, an upscale B&B, or an investment in future development. Set on 425 feet of pristine water frontage, this estate captures the essence of Highland Lake living - natural beauty, year-round recreation, and endless opportunity.

431 W Wakefield Blvd, Winchester

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