376 E Wakefield Boulevard , Winchester, CT 06098

DREAMING OF A LAKE HOUSE? – This charming renovated 4 BR home with 2 full baths sits on 91 feet of water frontage with its own private dock, sea wall and also has steps to enter the crystal clear water of Highland Lake. You can sit back , relax and enjoy drinks or your morning coffee on the large deck that boats scenic views of the lake surrounded by nature. An brick sidewalk leads the way to this most attractive home where you will find and an open floor plan with a spacious kitchen with built in hutch, dining room and family room with hardwood floors and sliders to the deck. Off the FR area is a dry bar. French doors open to the living room with hardwood floors, built in bookcases and a wood burning fireplace -perfect after a day of skiing, fishing or hiking. There is also a hot tub room with great views of the lake as well as a first floor bedroom and a full bath. The knotty pine walls lend a woodsy country touch to this wonderful home. The second floor is an open area with three skylights and is used as a gaming room with an office overlooking the lake. A master bedroom with stunning lake views and 2 additional bedrooms complete this level. A full walkout basement and two car detached garage offer plenty of space for storing your canoe, kayak or floats. You can gather around a fire pit after a day on the lake or sit by the fireplace after an autumn hike in the mountains. Highland Lake is 444 acres nestled in the Berkshires. 2 hrs to NYC and 20 min to Mass.

372 East Wakefield Boulevard , Winchester, CT 06098

Perched on a nubble overlooking the expands of 2nd bay at Highland Lake. This property offers much privacy as it is located at the end of a private road with only 3 other homes on it.Plenty of room for guest parking. It appears enough room to tear down the cottage and build one of the most private year round homes on the lake. Property faces due west for stunning sunsets. Abutted by 3 acres of preserved land.

25 E Lake Street , Winchester, CT 06098

125+ ft highland Lake direct waterfront with dock,large shed and 1/2 bath with outside access ,paved RV site with electric hook-up, nice large level yard…full in law set-up with bedroom,great room with stainless appliances laundry, french doors to patio with great lake views..main level has foyer, mud room and great room with large island stainless appliances pantry, and awesome lake views, den/dining room/office with wood fired pizza oven and 1/2 bath master bedroom suite with full bath and laundry area two additional bedrooms full bath car garage with second floor workshop,studio…agent owner related

39 East Lake Street , Winchester, CT 06098

Direct Waterfront on Highland Lake! Great house with lots of updates. 71 ft. of lakefront. Property includes a waters edge boathouse with bar and refrigerator, 2 docks, sprawling backyard, & wonderful back deck with an awning. perfect place for a party! Inside has had lots of updates including hardwood floors, kitchen updated, bathroom updates & more. Garden area on side of house. Very tranquil setting to spend your days. Central air is included for hot summer days. also the hot tub is included.

51 East Lake Street , Winchester, CT 06098

This beautiful, stately, A frame chalet was custom built by the owner as his retirement home. With 6 bedrooms, 4 full baths and 2 half baths it is truly a lake house for your whole family. The totally private main suite is on the upper level and features a detached sitting room with balcony overlooking the living area. There is also an additional suite on the main floor. The home has an open, airy feeling with 9 foot ceilings throughout, a cathedral ceiling in the dining/living room and a floor to ceiling fieldstone fireplace. A large composite deck overlooks the water and was designed with an integrated handicap ramp. There is a heated two plus car garage completely equipped with retractable reel style compressed air and water drops, generator hookup as well as a half bath . The heating/air conditioning system features a multi fuel boiler with 4 zones and dual A/C compressor units. All smart home functions including security with indoor/outdoor recording infrared cameras, home temperature control and outdoor sprinkler system can be controlled remotely via most devices. Add a professionally landscaped yard and a beautiful cobblestone patio area. The private waterfront is equipped with electricity, water, sound, two sheds for storage, boat launch area and a permanent concrete pier style composite dock with slide and diving board.

129 East Lake Street , Winchester, CT 06098

Recently expanded and beautifully remodeled colonial with hardwood floors and high end finishes throughout; enjoying expansive views of the lake from all three levels of living space. The pictures/slide show only tells part of the story. This house was carefully designed with a focus on entertaining for family and friends with an open floor plan and abundance of light. A true feature of the house and statement piece are the two folding glass doors merging the lake and large deck with the living room. The finished basement room with half bath enables full use of the backyard, hot tub, and waterfront dock. The dock house offers a relaxing shelter right on one of the largest lake frontages. An additional feature is the boating inlet next to the dock house; making launching of kayaks, canoes, jet skis, and other small boats easy. Just minutes from town and shopping, the house is conveniently situated.

169 W Wakefield Boulevard , Winchester, CT 06098

Highland Lake â“ Waterfront. Well maintained and designed for easy living, this 1,632 sq. ft. lake home with 2 bedrooms and 1 bath offers a smartly designed open floor plan and beautiful views from most rooms! Eat-in kitchen with breakfast bar. Spacious living/dining room area with hardwood floors and exposed beams add to the charm of this home. The great room with its wall of windows overlooking the water not only offers nice water viewing but also the flexibility to use this room to fit your needs, could be great additional sleeping space for guests. Large master bedroom with walk in closet and water views. The walk out lower level offers additional space for storage, a workshop or could be easily finished for more living space. Additional features of this home include: waterfront with dock, covered patio, public sewer, newer roof, furnace and driveway. Highland Lake is a 444 acre full-service lake offering all-weather activities including boating, skiing, swimming, ice skating, ice fishing & cross country skiing, etc., and is known for itâs great fishing; it is also one of CTs cleanest lakes. Easy travel from NYC, Boston and Southern CT. Minutes to Rte 8. Nearby amenities include Infinity Music Hall, the Berkshires, Warner Theater, shopping and restaurants. This home offers all of the conveniences you want in a lake home while being easy to maintain. Donât miss it!

211-212 W Wakefield Boulevard , Winchester, CT 06098

This spectacular 3 structure compound has a main house of 6800 sq.ft with a wrap around balcony that offers a view of the lake. The large master suite has a walk in closet and luxurious bathroom. The open style kitchen and dining room opens to the balcony and back yard for entertaining. The large bedrooms, music room, game room, living room, sun rooms, and more make it a great family house. It also boasts a 2 and 3 car garage, plus parking for 15 additional cars. The first of two on the lake houses has two bedrooms, a balcony and deck, dock, 1.5 bath, full kitchen and living room. The second has a loft bedroom, 1.5 bath, kitchen,2 decks, balcony, kitchen, storage, and 2 docks with a boat lift. Combined they have 250 ft. of lakefront.

341 W Wakefield Boulevard , Winchester, CT 06098


405 W Wakefield Boulevard , Winchester, CT 06098

Highland Lake, a 444 acre body of water noted as one of the cleanest lakes in Connecticut. This year round one owner home has also been renovated with quality materials and finishes over the last few years. Stunning views from a newer Trex wrap around deck which overlooks a beautifully landscaped property and includes a spacious private waterfront with 115 feet, beach for launching your kyak or boat, a dock, entertaining area with patio and a cabana housing a bathroom, refrigerator and storage. A contemporary post and beam home with an Adirondack feeling in this open floor plan featuring a stone fireplace, vaulted ceiling and great floors and flows into the spacious dining area with access to the deck. Updated chef’s kitchen has a 5 burner gas cook top, center island, pot rack and granite counters. An en suite first floor master bedroom and beautifully appointed bath with private deck. The second level bedroom has a full bath and office area. The finished walk out lower level (450+/- sq.ft) with 1/2 bath can be a third bedroom or game room and has lake views. The attached garage is deep and wide for cars with work area. CertainTeed siding, newer solar skylights, doors, 2017 roof and converted to propane heat. A generator is also included, lighting is built into stone walls, electric and water in the cabana and concrete sea wall. Buyers to assume balance of sewer assessment, approx. $2,900. Enjoy your summers or year round living at this most desirable lake.