Luxury homes for sale & real estate in Winchester, CT

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538 Wheelers Pt, Winchester, CT 06098

ABOUT THIS HOME
Luxury Home for sale in Winchester, CT:
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! A Most Unique Lakehouse!!

$1,880,000

4 beds3 baths2,496 sq ft

538 Wheelers Pt, Winchester, CT 06098

0.7 acre lot • $50 HOA • Garage

435 W Wakefield Blvd, Winchester, CT 06098

ABOUT THIS HOME
Luxury Home for sale in Winchester, CT:
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, wh

$1,700,000

8 beds4.5 baths5,231 sq ft

435 W Wakefield Blvd, Winchester, CT 06098

1.51 acre lot • 6 garage spots • Car-dependent

431 W Wakefield Blvd, Winchester, CT 06098

ABOUT THIS HOME
Luxury Home for sale in Winchester, CT:
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

$2,800,000

9 beds5.5 baths7,000 sq ft

431 W Wakefield Blvd, Winchester, CT 06098

1.9 acre lot • 2 garage spots • Car-dependent

119 W Wakefield Blvd, Winchester, CT 06098

ABOUT THIS HOME
Luxury Home for sale in Winchester, CT:
Stunning Lake Vistas! Have you been dreaming of a lake view and a property that is Special, Unique and TURN KEY? Fifty feet of waterfront property is included with boat dock and lift for lake enthusiasts! Nestled across from the serene First Bay, this beautifully renovated two-family home can be used as a single family and offers breathtaking water views and modern comforts. Perfect as a family retreat or an income-generating property, the home is fully renovated with upscale finishes throughout and boasts central air, newer appliances, windows, siding, and high-efficiency propane-fueled furnaces. Gorgeous details throughout make this a truly exceptional property. On the first floor, you'll

$859,900

4 beds2 baths1,781 sq ft

119 W Wakefield Blvd, Winchester, CT 06098

0.62 acre lot • 2 garage spots • Car-dependent

711 W Wakefield Blvd, Winchester, CT 06098

NEW CONSTRUCTION

ABOUT THIS HOME
Luxury Home for sale in Winchester, CT:
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.

$1,500,000

3 beds2.5 baths2,664 sq ft

711 W Wakefield Blvd, Winchester, CT 06098

0.61 acre lot • 2 garage spots • Car-dependent

175 Main St, Winchester, CT 06098

$995,000

14 beds7 baths4,860 sq ft

175 Main St, Winchester, CT 06098

5,662 sq ft lot • Very walkable

508 W Wakefield Blvd, Winchester, CT 06098

$1,650,000

7 beds4 baths2,687 sq ft

508 W Wakefield Blvd, Winchester, CT 06098

1.63 acre lot • 3 garage spots • Car-dependent

469 Platt Hill Rd, Winchester, CT 06098

$1,100,000

4 beds2 baths3,088 sq ft

469 Platt Hill Rd, Winchester, CT 06098

7.11 acre lot • Car-dependent

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$850k+

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77 Deer Hill Rd, Colebrook, CT 06021

ABOUT THIS HOME
Luxury Home for sale in Winchester, CT:
Enchanting Antique Dutch Colonial Estate with Carriage House and Barn. Nestled in a serene and private 51.2-acre haven, this stately home is a harmonious blend of historic charm and modern sophistication. As you traverse the meandering stone walls and explore the mix of sun-kissed meadows and whispering forests, you'll discover a world where time stands still, yet every modern convenience is at your fingertips. The property's outdoor allure is undeniable. Multiple walking or riding trails invite adventure, and the gardens, barn, carriage house and stone outbuilding offer endless possibilities for outdoor enjoyment. Step inside and be greeted by the warm embrace of rich hardwood floors, two

$1,200,000

5 beds2.5 baths3,307 sq ft

77 Deer Hill Rd, Colebrook, CT 06021

51.28 acre lot • Car-dependent

399 Colebrook Rd, Colebrook, CT 06021

VIDEO TOUR

ABOUT THIS HOME
Luxury Home for sale in Winchester, CT:
HILLTOP COMFORT IN COLEBROOK - Welcome home and put those cares aside in this meticulously maintained Country Colonial, a home transformed in the 1990's with a seamless conversion from a single level house to a spacious two level home. The 10.15 acres includes two additional building lots, a spring fed pond, apple trees, stone walls, gardens that delight in any season, and a wonderful patio that overlooks the meadow. The 4 bay garage includes a 2nd level for additional storage. The home features a south facing 3 season Porch, hardwood floors, a brick hearth wood burning fireplace, light filled rooms, a thoughtfully appointed Kitchen, a Primary Bedroom Suite that includes a sunny Balcony - a

$925,000

4 beds3 baths3,016 sq ft

399 Colebrook Rd, Colebrook, CT 06021

10.15 acre lot • 4 garage spots • Car-dependent

841 Winchester Rd, Norfolk, CT 06098

ABOUT THIS HOME
Luxury Home for sale in Winchester, CT:
Gracefully nestled at water's edge among lofty pines on over 115 utterly private and unspoiled woodland acres, this breathtaking lakefront country home features five bedrooms and four-and-a-half bathrooms and over 8,000 sq ft of luxurious living space. With extraordinary craftsmanship and exceptional materials, this custom built contemporary residence harmoniously integrates with its natural surroundings, showcasing cathedral ceilings, custom cherry cabinetry, heart pine and stone floors, and expansive stone fireplaces. Seemingly endless Albertini sliding glass doors and large windows frame captivating views of the manicured grounds and Winchester Lake, a 229-acre body of water known for it

$9,750,000

5 beds4.5 baths8,240 sq ft

841 Winchester Rd, Norfolk, CT 06098

115 acre lot • 3 garage spots • Pool

Luxury Homes for Sale in Winchester

There are currently 8 luxury homes for sale in Winchester at a median listing price of $362K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Winchester stay on the market for 63 days and receive 4 offers. This map is refreshed with the newest listings in Winchester every 15 minutes.

In the past month, 10 homes have been sold in Winchester. In addition to houses in Winchester, there were also 4 condos, 0 townhouses, and 3 multi-family units for sale in Winchester last month. Find your dream home in Winchester using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Winchester are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Winchester. If you're looking to sell your home in the Winchester area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Winchester with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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