55 Connecticut Properties

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Wakefield Boulevard
$2,800,000

Winchester, CT
House
Rooms: 12
Bedrooms: 9
Bathrooms: 6
Web ID: 24042374

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...

(203) 253-1800

Wheelers Point
$1,855,000

Winchester, CT
House
Rooms: 8
Bedrooms: 4
Bathrooms: 3
Web ID: 24052635

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!

(203) 253-1800

W Wakefield Boulevard
$1,650,000

Winchester, CT
House
Rooms: 11
Bedrooms: 7
Bathrooms: 4
Web ID: 24024787

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...

(203) 253-1800

W Wakefield Boulevard
$1,500,000

Winchester, CT
House
Rooms: 12
Bedrooms: 8
Bathrooms: 5
Web ID: 24047556

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...

(203) 253-1800

W Wakefield Boulevard
$1,500,000

Winchester, CT
House
Rooms: 6
Bedrooms: 3
Bathrooms: 3
Web ID: 24022821

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.

(203) 253-1800

Main Street
$950,000

Winchester, CT
House
Rooms: 28
Bedrooms: 14
Bathrooms: 7
Web ID: 24073478

Addresses include 175 Main Street and 183 Main Street in Winsted, CT. Amazing opportunity to acquire a 9 Unit Asset (7 Apartments + 2 Retail) in Winsted with anchor tenant Noli's Restaurant (Rent $2,266 w 3% increase/year) w over 20 years in business! Pride of Ownership is evident with Capital Improvements made by the current owners, including: new water heaters, heating zones, electrical upgrades, fire rated tenant main doors & new fire alarms/strobes in both buildings. The unit mix is: 1, 4 bedroom ($1,100); 4, 2 bedrooms ($1,000; $1,050; $900; the other can be rented for up to $1500 per month) and 2, 1 bedroom units ($950 each). The 175 Main St had a roof replacement in 2021, a privacy fence enclosure installed & all 4 residential units have gone through renovations. 183 Main St has had a roof replacement in 2023, aft wall structural repair, new studs, insulation, beams...

(203) 253-1800

W Wakefield Boulevard
$849,900

Winchester, CT
House
Rooms: 9
Bedrooms: 4
Bathrooms: 2
Web ID: 24075940

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...

(203) 253-1800

W Wakefield Boulevard
$849,900

Winchester, CT
House
Rooms: 9
Bedrooms: 4
Bathrooms: 2
Web ID: 24058804

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...

(203) 253-1800

S Main Street
$749,900

Winchester, CT
House
Rooms: 17
Bedrooms: 9
Bathrooms: 5
Web ID: 24027049

THREE PROPERTIES ONE PRICE!!! Includes single family, multi family & additional lot totaling 4.36 acres. 1. 3500 sq ft 2 family home featuring 1800's architecture including massive period correct windows, wrap around porch, beautiful stone foundation, and detached 2 car garage. 5 bed, 2 1/2 bath main house with 2 bed, 1 bath attic apartment, freshly updated. Brand new whole house natural gas heating system! 1.08 acres 2. Updated 960 sq ft ranch. 3 bed, 1 bath, walk out basement, great backyard with tons of potential. .37 acres. 3. 2.9 acres of undeveloped land. Potential for multiple access points. Condo's? Apartments? Parking garage? Bring your ideas and imagination. All properties sold together. Tax & Square footage is total for all three properties.

(203) 253-1800
Contract Signed
Property for Sale at South Road, Winchester, Connecticut - Bedrooms: 4 
Bathrooms: 3 
Rooms: 11  - $679,000 Previous PhotoNext Photo

South Road
$679,000

Winchester, CT
House
Rooms: 11
Bedrooms: 4
Bathrooms: 3
Web ID: 24076783

Discover your private sanctuary in the heart of historic Winchester Center, where tranquility meets nature! This contemporary Cape-style home boasts spacious, light-filled rooms that have been thoughtfully updated throughout. Elegant details such as crown molding, beams, skylights & oversized windows invite the beauty of the outdoors in-all showcasing your private pond! The main floor is designed for comfort & functionality, featuring a chef's kitchen with walk-in pantry, dining room, formal living room, library, den, office & generous great room currently used as a primary bedroom. A sunroom finishes off the main level & as you step outside to the terrace, you'll find a Gunite pool surrounded by seating areas with sweeping views-the perfect setting for entertaining or relaxing. Upstairs, the primary suite offers a spa-like retreat with a soaking tub. Two additional bedrooms w/ bath provide privacy & comfort. A central loft overlooks the living room, while a dedicated laundry...

(203) 253-1800

18 Taylor Brook Road
$650,000

Winchester, CT
House
Rooms: 7
Bedrooms: 3
Bathrooms: 3
Web ID: 170551066

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!

(203) 253-1800

Walnut Street
$550,000

Winchester, CT
House
Rooms: 15
Bedrooms: 5
Bathrooms: 3
Web ID: 24071827

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...

(203) 253-1800

Torringford Street
$535,000

Winchester, CT
House
Rooms: 8
Bedrooms: 4
Bathrooms: 3
Web ID: 24067951

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...

(203) 253-1800

Pratt Street
$480,000

Winchester, CT
House
Rooms: 7
Bedrooms: 4
Bathrooms: 2
Web ID: 24073605

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.

(203) 253-1800
Contract Signed
Property for Sale at Sunny Ridge Drive, Winchester, Connecticut - Bedrooms: 3 
Bathrooms: 3 
Rooms: 7  - $399,900 Previous PhotoNext Photo

Sunny Ridge Drive
$399,900

Winchester, CT
House
Rooms: 7
Bedrooms: 3
Bathrooms: 3
Web ID: 24075058

Charming One-Owner Split Level in a Private Rural Setting. Discover the perfect blend of privacy, space, and convenience in this beautifully maintained 1,800 sq. ft. split-level home, nestled on a serene 1-acre lot at the end of a cul-de-sac abutting the Barkhamsted town line. This home offers seven well-appointed rooms, including a spacious living room with a propane stove set in the fireplace, a formal dining room, a bright and functional kitchen, a cozy family room, three generously sized bedrooms, and 2.5 baths. Step outside to enjoy the peaceful surroundings from the modest deck off the back of the home, which overlooks the private backyard-an ideal spot for relaxation or outdoor gatherings while taking in the sights and sounds of nature, including frequent visits from deer, songbirds, and other local wildlife. Designed for comfortable living, this home boasts an abundance of closets and storage throughout. The attached two-car garage features...

(203) 253-1800

Orchard Street
$399,900

Winchester, CT
House
Rooms: 8
Bedrooms: 4
Bathrooms: 2
Web ID: 24061642

Renovated to 4 Bedroom and 3 Full-bath home with 2028 SQFT, this stunning Colonial on Private Road a short walk to Highland Lake. This newly remodeled 1875 home seamlessly blends historic charm with modern amenities. Inside discover a spacious floor plan offering an abundance of natural light perfect for both entertaining and everyday living. The custom kitchen is a chef's dream featuring sleek quartz and waterfall counter-tops, gorgeous ceramic tile, high end stainless steel appliances and wine refrigerator. Every detail in this home has been carefully thought out adding the laundry on upper level, 3 full custom bathrooms, solid oak hardwood floors, and ample storage for comfort and flow. The upper level has a large primary with en-suite bathroom, ensuring privacy & relaxation. The 3rd bedroom can function as a home office, offering a peaceful & productive space with views of the Mountains. Equipped w/ energy-star rated systems this home...

(203) 253-1800
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