Winchester Real Estate, Homes and Condos for sale

All Winchester homes currently listed for sale in Winchester as of 05/22/2019 are shown below.  You can change the search criteria at any time by pressing the 'Change Search' button below.

If you have any questions or you would like more information about any Winchester homes for sale or other Winchester real estate, please contact us and one of our knowledgeable Winchester REALTORS® would be pleased to assist you.


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$2,899,999
139 Grantville Road, Winchester CT 06098
6
BEDS
5
BATHS
4,172
SQFT
$695
$/SQFT
419.09
ACRES
1830
BUILT
"Classic American Litchfield county colonial dating back to the late 1700s in the foothills of the Berkshires. The current owners descend from Benjamin Franklin, the abolitionist Lucretia Coffin Mott and the founder of the Metropolitan Museum of Art. The farmhouse is a classic colonial dating back to the late 1700s. The approx. 3,000 sq ft house has 6 bedrooms, 4 1/2 bathrooms, 4 original fireplaces and a beehive oven. There are some of the original wide plank floors and there is a playroom with a stone wall fireplace and plenty of original features throughout the house. There is a natural spring-fed swimming pool, a tennis court (in need of resurfacing) and 21 acres of cleared land with the original stone walls. There is an abundance of wildlife (including deer, wild turkeys, quails and many more), wild fruits and native plants. Very peaceful, quiet setting, all major amenities (shops, hospital, transportation) are just a 15 minutes drive away."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $2,999,000 TO $2,899,999 
$1,900,000
210-212 West Wakefield Boulevard, Winchester CT 06098
11
BEDS
9
BATHS
10,000
SQFT
$190
$/SQFT
1.17
ACRES
1923
BUILT
"THIS IS AN EXCLUSIVE OPPORTUNITY TO OWN A TRUE COMPOUND ESTATE ON HIGHLAND LAKE. THIS 1 OF A KIND LOCATION INC 3 HOMES. THE 7000+ SQFT MAIN RESIDENCE HAS 5+ BDRMS, 4.1 BTHS & 7+ CAR GARAGE W/ BOAT STORAGE. THE EXPANSIVE 1ST FLR PLAN FEATURES MB SUITE, OPEN & BEAUTIFUL REMODELED EIK W/GRANITE & SS APPLIANCES, XLG OPEN DR, WARM COZY LR W/FP, A SUN PORCH & A FAMILY ROOM. ALL ROOMS HAVE EXPANSIVE VIEWS OF THE WATER. THERE IS ALSO A DECK SYSTEM THAT STRETCHES ACROSS THE ENTIRE FRONT OF THE HOME OVERLOOKING THE LAKE. THE 2ND FLR HOUSES ALL THE REST OF THE BDRMS & A HUGE BONUS AREA THAT IS CURRENTLY BEING USED AS A MUSIC ROOM. THE 3RD FLR LEVEL IS A TRUE RECREATIONAL SPACE FOR PEOPLE OF ALL AGES THAT CAN BE USED AS ADDED SLEEPING SPACE & IS COMPLETED W/ A FULL BTH. THE WALKOUT LOWER LEVEL IS HEATED PLUMBED, WIRED & WAITING TO BE FINISHED FOR AN AMAZING WATERFRONT ENTERTAINING AREA WHICH COULD INCLUDE AN INFINITY POOL LOOKING OUT TO THE LAKE. THE 2ND HOME IS DIRECT WATER FRONT & DELIVERS A BIG BANG IN A SMALL PACKAGE. IT COMES W/ 2 LEVELS OF LIVING SPACE & 2 LEVELS OF DECK SPACE, A BOAT LIFT, A SWIM DOCK & MULTIPLE AREAS TO ENTER THE WATER. THE 3RD HOME CAN SLEEP 8-10 PEOPLE IN BEDS IN 4 SEPARATE BEDROOM AREAS. IT ALSO HAS A FULL KITCHEN, LR & 1.5 BTHS. THE OUTDOOR ENTERTAINING AREA HAS MULTIPLE LEVELS OF DECKS, A BOAT LIFT & 2 DOCKS. TOGETHER THE HOMES HAVE OVER 250'+ OF WATERFRONT & THE PANORAMIC VIEWS OF THE LAKE ARE 2ND TO NONE ** FOR MORE INFO SEE MLS 170177143 & 170177142**"
$1,500,000
211/212 West Wakefield Boulevard, Winchester CT 06098
5
BEDS
6
BATHS
7,591
SQFT
$198
$/SQFT
1.05
ACRES
1923
BUILT
"EXCLUSIVE OPPORTUNITY TO OWN AN ESTATE ON HIGHLAND LAKE. THIS AMAZING LOCATION INC 2 HOMES. THE 7000+ SQFT MAIN HOME HAS 5+ BDRMS, 4.1 BTHS, 7+ CAR GARAGE W/BOAT STORAGE AREA. THE EXPANSIVE 1ST FLR PLAN FEATURES MB SUITE, OPEN & BEAUTIFUL REMODELED EIK W/GRANITE COUNTERS, CHERRY CABINETS & SS APPLIANCES, XLG OPEN DR, WARM & COZY LR W/FP, A SUN PORCH & A FAMILY ROOM. ALL ROOMS HAVE AMAZING VIEWS OF THE WATER. THERE IS ALSO A DECK SYSTEM THAT STRETCHES ACROSS THE ENTIRE FRONT OF THE HOUSE OVERLOOKING THE LAKE. THE 2ND FLOOR HOUSES THE REST OF THE BEDROOMS & A HUGE BONUS AREA CURRENTLY BEING USED AS A MUSIC ROOM. THE 3RD FLOOR LEVEL IS A TRUE RECREATIONAL SPACE FIT FOR PEOPLE OF ALL AGES THAT ADDS ADDITIONAL SLEEPING SPACE & IS COMPLETED W/ ANOTHER FULL BATH & LAUNDRY. THE WALKOUT LOWER LEVEL IS HEATED, PLUMBED, WIRED & WAITING TO BE FINISHED FOR AN AMAZING WATER SIDE ENTERTAINMENT AREA WHICH COULD INC AN INFINITY POOL LOOKING OUT OVER THE LAKE. THE 2ND HOUSE IS DIRECTLY ON THE WATER & DELIVERS A BIG BANG FOR A SMALL PACKAGE. IT COMES W/2 LEVELS OF LIVING SPACE & 2 LEVELS OF DECK SPACE, A BOAT LIFT, A SWIM DOCK & MULTIPLE AREAS TO ENTER THE WATER. THE PANORAMIC VIEW FROM EVERY SPOT ARE 2ND TO NONE. THIS AWESOME COMBO OF HOMES CAN BE PURCHASED WITH MLS# 17077143 FOR A DISCOUNTED TOTAL PRICE. THIS WOULD MAKE A TRUE COMPOUND (SEE MLS # 170177145). WITH ALL 3 HOMES YOU WOULD HAVE HOUSING ABILITY OF 11 BDRMS, 9 BATHS, PARKING FOR 20+ CARS & OVER 250' OF DIRECT WATERFRONT ACCESS."
$1,050,000
534 Wheelers Point, Winchester CT 06098
3
BEDS
2
BATHS
2,746
SQFT
$382
$/SQFT
0.54
ACRES
1990
BUILT
"Highland Lake architect designed year round three bedroom home that from lake side is admired by many boaters for its great style, sweeping lawn and gardens. A thoughtful floor plan creates an open feel and allows water views from most rooms. The living room with its vaulted and beamed ceiling has a stunning stone fireplace, hardwood floors and track lighting and flows into the dining room. The well designed kitchen is spacious and also includes a breakfast area with sliders to the deck. There is also a nice den with access to the deck with pergola. The second floor master has gorgeous views of the lake with white beams, two mirrored closets and electronic windows. An additional bedroom and bath are on this level with storage areas. The yard and outdoor entertaining areas are terrific giving you easy access into the water. A boat lift and aluminum dock are included. Very pretty gardens surround this perfect home. There is a large shed type building that can be used for all types of storage. Central air throughout, surround sound, approximately 100 feet of waterfront, circular drive, stone walls and Marvin windows are just a few of the fine components of this property. Walk out lower level has one finished room. All this set on a private lane with five other beautiful lakefront homes. Highland Lake is a 444 acre lake known for its crystal clear water, great fishing and boating. This is a must see home! 2 hrs. to NY&Boston, 30 min. to Bradley International Airport."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $1,100,000 TO $1,050,000 
$999,999
512 West Wakefield Boulevard, Winchester CT 06098
3
BEDS
2
BATHS
2,003
SQFT
$499
$/SQFT
0.86
ACRES
1910
BUILT
"ONE OF THE GEMS ON HIGHLAND LAKE IS PINE KNOLL. THIS BREATHTAKING PROPERTY IS LOCATED ON A PENINSULA HAVING WATER ALL AROUND IT. IT'S FEATURES INCLUDE A PRIVATE ISLAND AND TWO DOCKS ON THE COVE SIDE FOR PEACEFUL KAYAKING, SWIMMING AND EASE OF DOCKING BOATS ALL WHILE STILL HAVING DEEDED ACCESS TO DEEP WATER SIDE FOR BOATING SPORTS. IT IS A HOME THAT SUITS EVERY SEASON: ENJOY LONG SUMMER DAYS AND COOL FALL NIGHTS ON THE EXPANSIVE WRAP AROUND DECK AND SWEEPING FRONT PORCH. WINTER WILL BRING ANOTHER ELEMENT OF ENJOYMENT TO THE LAKE WITH SNOWMOBILING, SKATING, ICE FISHING, SNOWSHOEING AND SKIING IS JUST A SHORT DRIVE AWAY. LOOKING FROM EVERY WINDOW IS A VIEW OF THE STUNNING WATER AND WIDE PROFESSIONAL LANDSCAPING MAKING THIS THE MOST BEAUTIFUL LOCATION ON THE LAKE. THIS HOME INCLUDES PLENTY OF PRIVATE PARKING AND A TWO CAR GARAGE WHICH IS A RARITY ON THE LAKE SO NO WORRIES ABOUT ENTERTAINING AND HAVING LOTS OF GUESTS. THE HOMES RECENT INTERIOR UPDATES INCLUDE A REMODELED KITCHEN WITH GRANITE COUNTERS AND STAINLESS APPLIANCES, A SPA QUALITY FULL BATH AND HARDWOOD FLOORS THROUGHOUT THE FIRST FLOOR. ON THE EXTERIOR THERE HAS BEEN EXTENSIVE MILL WORK ADDED AROUND THE WINDOWS. ONE LOOK AND YOU ARE HOME!! ALL YOU NEED TO DO IS UNPACK YOUR CLOTHES BECAUSE THIS IS TRULY TURNKEY WITH ALL PERSONAL PROPERTY AND SPORTING EQUIPMENT INCLUDED. HURRY AND YOU CAN BE IN TO ENJOY THE WHOLE SUMMER SEASON WITH YOUR FAMILY. *ADDITIONAL BEDROOMS AND A BATH COULD BE ADDED IN THE WALK UP 3RD FLOOR LEVEL*"
$975,000
850 East Wakefield Boulevard, Winchester CT 06098
4
BEDS
3
BATHS
3,170
SQFT
$308
$/SQFT
0.43
ACRES
1926
BUILT
"The Waterfront Home You Have Been Waiting For!! Escape to the tranquility of year round lake living - this beautiful three bedroom, three full bath home was renovated in 2002 and has approx. 100 ft of water frontage as well as a three car heated detached garage with a fabulous three room apartment above perfect for guests or income. Walk through the door of this well maintained home and you will fall in love with the pretty custom kitchen with granite counters, a travertine tile back splash, under counter lighting, a deep sink, skylights and hardwood floors. The breakfast nook in the kitchen offers you peaceful panoramic water views of the lake. Off the kitchen you will find an upper deck perfect for enjoying your morning coffee or for barbecuing and taking in the sounds of nature and of course those gorgeous views of the lake and mountains. The natural light from the windows in the living room/dining room create a bright and airy space and allow you to take in the absolute BEST water views - what a relaxing way to live. The brick fireplace is wonderful for those chilly nights. There is a guest bedroom on the main floor with a full bath. A beautiful staircase leads the way to the second floor master bedroom with great closets and yes views of the lake - waking up to a water view doesn't get any better. There is an additional bedroom on this floor and a full bath. (see additional remarks)"
$895,000
504 West Wakefield Boulevard, Winchester CT 06098
3
BEDS
3
BATHS
2,249
SQFT
$398
$/SQFT
0.57
ACRES
1995
BUILT
"Privacy, views & approximately 350' of waterfrontage - contemporary lakehouse with 2250 SF. Great floor plan for entertaining. Boathouse, 2 docks, swimming area, stone walls, vinyl decking, patios, expansive lawns and nicely landscaped property-a large, sunny, level parcel (over half an acre). The home features a large kitchen w/breakfast bar, granite countertops, tile floor; hardwood flooring in LR w/cathedral ceiling, sliders to deck and stunning lake views. DR has coffered ceiling. All bedrooms have walkin closets plus three full baths; separate laundry room with built ins; walk up attic for storage; family room w/tile floors and antique wood stove with access to covered patio area. Additional room used as office/exercise area. Stone stairs access the swimming area. Whole house generator just installed. Owner/Agent."
$875,000
424 East Wakefield Boulevard, Winchester CT 06098
5
BEDS
2
BATHS
3,693
SQFT
$237
$/SQFT
0.59
ACRES
1890
BUILT
"This Stunning Victorian Beauty is one of the prettiest homes on the lake built circa 1890 its a fabulous entertainment house! also a great investment for a rental. The sellers have done extensive improvements since purchasing this home to open it up to the commanding lake view it affords. New French doors to a new covered porch, deck and three season screened porch with mahogany flooring. More improvements to this five bedroom two full bath home include: kitchen renovation in 2010 to include granite countertops, deep sink, cabinetry and stainless appliances. Flooring installed in 2019. Totally remodeled and expanded second floor full bath with soaking tub and double quartz sinks. Rebuilt three second floor bedrooms, including adding cathedral ceiling and major custom window array in master bedroom. Rebuilt third floor, added dormer over the stairs and the front and back facing dormers, expanded carpeted bedroom with window-bed overlooking the lake with electric heat. Dock built in 2008, This home also has a fully insulated detached two car garage with upstairs artists studio built in 2009 and incredible amount of parking as well which is hard to find on the lake. Highland Lake is 445 acres and valued for fishing, boating, swimming and water skiing with a maximum depth of 63 feet. The Department of Environmental Protection stocks it annually with fish and considers it a trophy trout and bass management Lake. Two hours from Manhattan"
$869,000
262 Perch Rock Trail, Winchester CT 06098
7
BEDS
5
BATHS
4,416
SQFT
$197
$/SQFT
0.24
ACRES
2005
BUILT
"Amazing sunsets await you in this year round 6-7 br, 4.1 ba. waterfront home located on a quiet side street with little traffic on beautiful Highland Lake. The home's front foyer flows to a glass-walled living room with stunning views of the lake. The living room also features an attractive stone fireplace, built-ins and gleaming cherry floors. You will enjoy cooking and entertaining in the spacious kitchen which offers double ovens, a dacor 6 burner gas cook top, center island breakfast bar and cherry cabinets. The dining room is open to the kitchen and has hardwood floors. The first floor bedroom or office offers water views and a large closet. A laundry room and powder room complete the first floor. There is nothing better than waking up to lake views in the master bedroom which has its own private balcony, a walk in closet, a full bath w/ double sinks, a whirlpool tub for soaking and taking in the views and a walk in shower. Two other bedrooms share a jack & jill bath. The lower level of this home features a family room with a wood burning fireplace, a full bar for entertaining all your lake guests, a guest bedroom with water views, a walk in closet and a full bath. The family room opens onto a large paver patio perfect for grilling, dining, cocktails, hanging out with friends and family or sitting back with a good book. That's not all this home has to offer there is a also a private guest or in-law apartment with a living room with"
$849,500
123 Ashley Road, Winchester CT 06098
3
BEDS
3
BATHS
2,812
SQFT
$302
$/SQFT
3.00
ACRES
2005
BUILT
"Welcome to Water Haven - a truly serene private setting awaits you. Come watch the sunshine glisten on the water and take in the mesmerizing views from virtually every room. Water Haven sits on 3 acres with 250 ft. of water frontage on the shore of Connecticut's beautiful 82 acre Park Pond in the foothills of the Berkshires, offering four seasons of beautiful scenery and outdoor activities. Getting away from a busy life starts here with a true post and beam Yankee Barn home built in 2005 offering a casual and comfortable home of 2812 sq. ft. with two stone fireplaces. This three bedroom, 2.1 bath residence has an open floor plan with a large deck to enjoy the natural lake front setting with a beautiful stone bulkhead, a 20 ft. dock and floating dock as well as a sandy launch area for your kayak or canoe. Your guests will be happy to have their own private quarters with kitchen and bath. The lower level offers radiant heated floors and 10 ft. ceilings. This home also has solar panels to offset electric costs. This is a rare offering on a much sought after pond. Park Pond has residences scattered around the perimeter and offers four seasons of beautiful scenery and outdoor activities. It's a great place to kick back, relax and enjoy the beauty and tranquility of this special well cared for home on the pond. If you are a car buff or hobbyist you will certainly enjoy the heated garage space this home offers."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $875,000 TO $849,500 
$795,000
51 East Lake Street, Winchester CT 06098
6
BEDS
5
BATHS
3,888
SQFT
$204
$/SQFT
0.70
ACRES
1999
BUILT
"This spacious and well maintained one owner year round Contemporary offers abundant room for a growing family or generational gatherings offering six bedrooms and 4.1 baths. The living room has hardwood floors with a floor to ceiling stone fireplace and a vaulted ceiling and flows into the dining room with access to a large wrap around composite deck perfect for sunning or a barbecue. The stairs down the center of the deck lead the way to a a beautiful lawn for the dog or the children to play and to hold family picnics. The kitchen is well equipped with two double ovens, a five burner cook top and has granite counters. There is a master bedroom en-suite on the main floor as well as a nicely sized half bath and full laundry room. The second floor has a loft area which overlooks the living and dining room and offers great views of the lake, a generous master bedroom en-suite as well as two other bedrooms and a full bath. A finished walkout lower level completes the home with three additional bedrooms, a full bath with whirlpool tub and a family/media room with sliders to a paver patio. The lawn is professionally landscaped and also has an irrigation system in place. There are two sheds located on the property and are a bonus to store all your watercraft needs or even an extra refrigerator at water's edge. A pure sandy beach walk in access is perfect for swimming or to launch your kayak or paddle board. There is also a composite dock for your boat as well as a water slide."
$750,000
200 Perch Rock Trail, Winchester CT 06098
3
BEDS
3
BATHS
2,331
SQFT
$322
$/SQFT
0.21
ACRES
1948
BUILT
"THIS is a dream home. When you walk through the front door, you will know you have arrived. Your very own private oasis to relax and unwind in your serene, peaceful, beautiful lake home. Everything is perfect. Walking over that threshold, you immediately see clear views of the lake complimented by the gorgeous kitchen with spectacular 4' x 10' island and beautiful custom white cabinetry. Phenomenal sunrises and sunsets, exquisite sunlit spaces, sparkling new everything... Pristine, Immaculate, Turn Key, Water Front, Year Round Dreamy Lake Home! Soak in the absolutely breathtaking panoramic views of the water and landscape. Home is perched on the east shore of Highland Lake, a 444 acre lake known to be one of the cleanest lakes in Connecticut and where there is so much fun to be had! 2 beaches, a boat launch for swimming, stocked lake for fishing, water skiing, boating, sailing, kayaking, ice fishing in the winter months and sunshine all day long. This exquisite home has been completely rebuilt top to bottom and features a sun filled open floor plan, spectacular chef's kitchen, brand new second floor, spa-like baths, new mechanicals, new central air, new roof, new generator, brand new, expansive low maintenance Azek deck - the perfect spot for entertaining. Public water and sewer. Just 3/4 of an hour to Hartford, 2 hours to NYC and 45 minutes to the airport. Escape to the Hills. You will want to stay forever."
$745,000
436 Winchester Road, Winchester CT 06098
3
BEDS
3
BATHS
2,881
SQFT
$259
$/SQFT
52.36
ACRES
1988
BUILT
"Southwestern style and ambiance with dramatic details throughout in this custom built, one owner home. Thoughtfully designed, carefully constructed, and beautifully maintained, all on 52 acres for privacy and recreation. A chef's ideal kitchen, stone fireplaces in both the Master Bedroom and Great Room (with a warming oven), vaulted ceilings and beams, a Sun Room overlooking the front gardens, a 3 season rear Porch, granite and marble counters in the Kitchen and baths, state of the art wood and oil heating systems - and that's just the beginning. Please see this one for yourself, it will not disappoint."
$735,000
422 East Wakefield Boulevard, Winchester CT 06098
4
BEDS
3
BATHS
2,544
SQFT
$289
$/SQFT
0.48
ACRES
1924
BUILT
"Highland Lake in hot demand for its 444 acres of clean water , great fishing and boating. This charming year round home ( not a renovated cottage) has 4-5 bedrooms with 3 baths and a 25 x 25 deck with awning overlooking the water. It has been renovated by its present owner with an addition , newer kitchen, garage, central air in most of the home, newer roof and composite dock. The living room has a stone fireplace, vaulted ceiling, skylights and built-ins. A family room off the sun filled kitchen has direct access onto the deck with steps leading to a waterfront deck area and newer dock. The kitchen is very adequate with nice cabinetry, tile back splash and breakfast area with water views. A dining room, mudroom with cedar closet, pantry area and new full bath completes the first floor.Two additional baths with the bedrooms are on the second floor along with a laundry room/office . Pretty plantings surround the property with a seasonal brook and newer detached two car garage with storage. Newer well, sewers and good parking are a plus. Minutes to Rt 8 and under an hour to Hartford and Bradley International Airport. Two hours to NY. Enjoy great summer venues in the area, farmer's markets, the Berkshires , hiking , kayaking and skiing in the winter. Winsted has some great eateries, terrific cinema with dining, and NW Community College. This is a must see house in a beautiful setting and best value on the lake."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $789,000 TO $735,000 
$699,000
276 Pratt Street, Winchester CT 06098
3
BEDS
3
BATHS
3,072
SQFT
$228
$/SQFT
77.90
ACRES
1760
BUILT
"Nestled in the rolling hills of Litchfield County, in bucolic Winchester--the Gateway to the Berkshire Mountains --this quintessential 1760 Connecticut farmhouse, with its recent additions, is the perfect country retreat to repair from busy city life. The charming home is set high on 77.9 acres, allowing for expansive vistas of perennial gardens, meadows, woodlands and hills beyond. Situated near Highland Lake makes it a wonderful weekend or an ideal year-round home. Imagine a fabulous equestrian estate with paddocks, meadows and meandering private trails--the possibilities are endless. Don't miss this rare opportunity to make this serene property your own private oasis."
$675,000
760 Lake Drive, Winchester CT 06098
3
BEDS
3
BATHS
2,400
SQFT
$281
$/SQFT
0.20
ACRES
1910
BUILT
"Your new adventure starts right here... Move right in to this beautiful upscale all season home located on 3rd bay of Highland Lake. Everything rebuilt with all amenities brand new 2012. Open interior floor plan design with larger windows for the best natural light views of lake. Massive outdoor composite decks for entertaining. With sandy waterfront and a boating dock with exposure to western sunsets make this property a true gem. Take advantage of the year round lifestyle of lakeside living at its finest. Additional .08 acres included."
* LISTED OVER 120 DAYS 
$674,000
210 West Wakefield Boulevard, Winchester CT 06098
4
BEDS
2
BATHS
1,526
SQFT
$442
$/SQFT
0.12
ACRES
2010
BUILT
"WELCOME TO TAKITEZY BUNGALOW GETAWAY. AS SOON AS YOU ARRIVE YOU WILL BE SWEPT AWAY WITH THE INCREDIBLE PANORAMIC VIEWS OF HIGHLAND LAKE. YOU CAN'T HELP BUT NOTICE THAT THIS HOME WAS DESIGNED WITH FUN AND ENTERTAINMENT IN MIND. THERE ARE MULTIPLE DOCKS, CANTILEVER DECKS AND AREAS TO PARK YOUR BOAT TO ENJOY ALL THAT LAKE LIVING HAS TO OFFER. THIS YEAR ROUND HOMES INTERIOR FEATURES 4 BEDROOMS, 1.5 BATHS, HARDWOOD FLOORS THROUGHOUT AND AN OPEN FLOOR PLAN SO THERE IS PLENTY OF ROOM FOR EVERYONE AND THERE ARE NO WORRIES FOR PARKING BECAUSE YOU CAN FIT 6-8 VEHICLES. THE VIEWS FROM EVERY ROOMS WINDOWS IS SPECTACULAR AND MAKES YOU FEEL AS THOUGH YOUR ACTUALLY ON TOP OF THE WATER. THE MASTER BEDROOM HAS SLIDING GLASS DOORS AND A PRIVATE BALCONY TO ENJOY LAZY MORNINGS WITH A CUP OF COFFEE. THE ADDITIONAL 3 BEDROOMS ARE SPACIOUS AND COULD ACCOMMODATE 2 BEDS IN EACH ROOM FOR UP TO 6+ MORE SLEEPING CAPACITY. THIS HOME WAS COMPLETELY REMODELED IN 2011 AND A WHOLE HOUSE GENERATOR WAS INSTALLED FOR PEACE OF MIND LIVING IN OR AWAY. THERE ARE GREAT AMENITIES CLOSE BY ALSO INCLUDING SHOPPING, RESTAURANTS, MOVIE THEATER, MICRO BREWERY'S, AND A NEWLY REFRESHED MARINA AND BOAT SHOP. THERE'S NO SHORTAGE OF SPORTS AVAILABLE YEAR ROUND EITHER LIKE WALKING/BIKING PATH, HIKING, SKIING, TENNIS, GOLF, RIVER BOATING & TUBING ARE ALL A SHORT DRIVE AWAY. JUST ONE LOOK AND YOU WILL BE SWEPT AWAY. ***THIS HOME CAN BE PURCHASED AS A PACKAGE DEAL W/ MLS# 170177142 SEE MLS# 1701787145 FOR COMPLETE DETAILS***"
$650,000
714 West Wakefield Boulevard, Winchester CT 06098
3
BEDS
4
BATHS
2,400
SQFT
$271
$/SQFT
0.17
ACRES
2019
BUILT
"Ever dream of owning a lake front home? This is your chance! Admire the views from this new home currently under construction, located on Highland Lake. This 445 acre lake is a popular spot for boating, fishing, as well as other recreational purposes. The lake is stocked yearly with fish and considered a Trophy Trout and Bass Management Lake. The home will have an open floor plan with three levels. The main level consists of a open concept kitchen and living room, a combination laundry and half bath, as well as the master bedroom and bath overlooking the lake. The top floor has two bedrooms, both looking out over the lake and a full bathroom. Lake life is made easier from this bottom floor family/rec room designed for easy access to the lake and also has a full bathroom. The spectacular views from nearly every room will say it all! Come take a look for yourself today!"
$639,900
120 Ashley Road, Winchester CT 06094
3
BEDS
3
BATHS
2,556
SQFT
$250
$/SQFT
24.00
ACRES
2005
BUILT
"Welcome to tranquil Winchester Center where time slows down to a peaceful pace & only approx. 25 minutes to The Berkshires!! You will find this hidden gem situated 300' from the road for privacy! Travel up your 500' paved driveway to behold this Gorgeous custom built 3 bedroom 2.1 bath Contemporary with attention to detail in the finishes that include James Harde Plank Siding, Arch. Lifetime shingles, 2 x 6 Construction, structural laminate beams, footing drains, stone patio overlooking the grounds & babbling brook, Marvin Integrity Low E Argon Filled Windows, over sized 3 car garage with 10' doors & 11' ceilings sure to accomodate your own collections/hobbies. 1000 Gallon I/G Propane tank, Central Air, Masonary wood heater with fireplace heated hearth, wood waiter elevator for ease of bringing your firewood to the Great Room fireplace. All Trim & moldings throughout are custom milled wood, interior solid wood 6 panel doors. Cooks delight in your gourmet Kitchen with Granite counters, Custom Cherry Cabinets with 2 pull out spice drawers, pullout & soft closing drawers , 4 lazy susans in corner cabinets & 2 appliance cabinets with plugs. GE Monogram Appliances, 6 burner propane cook top, vented range hood with heat lamp & lighting. Convection wall oven, wall convection microwave, Prep sink for convenience in your large breakfast bar."
$598,000
309 Colebrook Road, Winchester CT 06098
5
BEDS
2
BATHS
2,132
SQFT
$280
$/SQFT
160.00
ACRES
1903
BUILT
"Offered is the perfect location for your mountain retreat, estate, horse farm, or nature sanctuary. Once a working cattle farm, the 160 mountain top acres are 90 % gently rolling, suitable for clearing and multiple uses. Still in place is the original 13 room home, barn, sheds, outbuildings and farm equipment from yesteryear! With old logging roads throughout and approx 20 acres of open fields, you need only add the horses. The abundance of wildlife, birds and butterfly's cannot be overstated on this nearly unspoiled land. The home with its old world charm, is hooked into a HUGE solar panel system that creates more energy than needed and actually credits the owners annually. The property borders state land and large pond to the south side. So bring your offers and live nearly off the grid on the magical mountain-top paradise. Per owner sq ft under roof is approx 3,500."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $650,000 TO $598,000 
$597,000
878 West Wakefield Boulevard, Winchester CT 06098
4
BEDS
2
BATHS
2,490
SQFT
$240
$/SQFT
0.35
ACRES
1973
BUILT
"Fantastic waterfront home. 4 bedrooms and a huge family room with wet bar and sliders that lead to a 14'x26' deck. There is another deck that is 14'x21'. Both decks feature retractable awnings. 16'x17' waterfront patio and gazebo. Large LR with FP., formal dining room and a cozy breakfast room overlooking the lake. Large workshop in the lower level. Long dock gives you plenty of room for all your watercraft. Private location at the end of the Lake. This house features solar panels which provide you with affordable electricity. Come live your dream in this lovely waterfront home!"
* PRICE LOWERED - $615,000 TO $597,000 
$549,000
39 East Lake Street, Winchester CT 06098
4
BEDS
2
BATHS
2,182
SQFT
$252
$/SQFT
0.69
ACRES
1900
BUILT
"Spacious, direct waterfront 8 room colonial featuring a 20x22 lower level family room with fireplace that opens onto a large private deck with hot tub. Home has tastefully updated kitchen and baths, hardwood floors and a master bedroom overlooking the lake. Beautifully landscaped yard with plenty of room for volley ball and outdoor activities. Enjoy sunsets and cocktails at the waters edge in the crabshack This island style cabana comes complete with a four seat bar that divides the interior sitting area from the covered outside porch. There is over 70 feet of waterfront with two permitted docks. This is the perfect setup for entertaining and enjoying the lake!"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $595,000 TO $549,000 
$524,900
842 East Wakefield Boulevard, Winchester CT 06098
3
BEDS
3
BATHS
2,032
SQFT
$258
$/SQFT
0.23
ACRES
1973
BUILT
"PLEASE NOTE GREAT PRICE IMPROVEMENT!!! The possibilities at 842 East Wakefield are like the view: endless! Two lots for the price of one AND one of the few full length lake views! The two lots are on either side of the road. The garage structure is a blank canvas! The street level is an enormous two bay garage which is large enough for cars, boats, or all of your toy storage. Its upper level was a heated bunk house at one time. Now, it is almost 700 sq.ft. of storage; with, of course, its own stunning full length lake view! This garage lot also has a large terraced lawn and driveway parking for at least 4 cars! But, let's face it: the party is on the water! The direct waterfront home is on three levels. The top floor of the embankment Colonial style dwelling has three bedrooms, one is a master with a private bath. The middle level features a snacks kitchen, a full bath, and a full width family room with a stunning elevated full length lake view, and a fireplace! The lake level has two large open living spaces with a gas fireplace and breathtaking views. No need to crawl up hillsides for an adult beverage either! The main kitchen and convenience powder room are right here! But, the waterfront is the true prize! The deep water concrete dock even has a diving board. The stationary aluminum dock adds even more space for the boats, skis, and any toys imaginable! So, stop by and see this four-season lake today! You will be impressed!"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $559,900 TO $524,900 
$479,900
212 East Wakefield Boulevard, Winchester CT 06098
3
BEDS
2
BATHS
1,320
SQFT
$364
$/SQFT
0.17
ACRES
1937
BUILT
"Waterfront on Highland Lake-this year round 3 bedroom/1.1 bathroom home has great swimming and boating access to the lake with 77.85 ft of frontage, kitchen with dining space and spacious living room with huge windows overlooking the lake, 1st floor half bathroom with laundry hook ups, 2nd floor features all 3 bedrooms and full bathroom, updated mechanicals, central air, plenty of off street parking and large flat yard. Located on first bay, 45 minutes from BDL, approximately 2 hours to Boston and 2.5 hours to NYC. Great private location on the point between shore Dr. and Perch Rock Trail."
* LISTED OVER 120 DAYS 
 
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