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Winchester Real Estate, Homes and Condos for sale

All Winchester homes currently listed for sale in Winchester as of 08/20/2019 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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$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**"
* LISTED OVER 120 DAYS 
$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."
* LISTED OVER 120 DAYS 
$925,000
850 East Wakefield Boulevard, Winchester CT 06098
4
BEDS
3
BATHS
3,170
SQFT
$292
$/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, 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)"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $975,000 TO $925,000 
$910,000
534 Wheelers Point, Winchester CT 06098
3
BEDS
2
BATHS
2,746
SQFT
$331
$/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 - $949,500 TO $910,000 
$908,000
28-44 South Main Street, Winchester CT 06098
18
BEDS
8
BATHS
8,457
SQFT
$107
$/SQFT
1.25
ACRES
1900
BUILT
"These 6 contiguous properties located on busy Rte.# 44 are being sold AS IS only as a package , not individually and are located in TG zone . Think of all the Potential development options . This zone is referred to as the Town Gateway , and for good reason . Walking distance to Northwestern Ct. Community College , Restaurants , Park , Recreation facilities and future Medical Facility . Major intersection of Rte.8 & Rte.44"
$849,900
504 West Wakefield Boulevard, Winchester CT 06098
3
BEDS
3
BATHS
2,249
SQFT
$378
$/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."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $895,000 TO $849,900 
$820,000
262 Perch Rock Trail, Winchester CT 06098
7
BEDS
5
BATHS
4,416
SQFT
$186
$/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"
* PRICE LOWERED - $835,000 TO $820,000 
$795,000
543 West Wakefield Boulevard, Winchester CT 06098
4
BEDS
3
BATHS
2,596
SQFT
$306
$/SQFT
1.00
ACRES
1990
BUILT
"METICULOUSLY MAINTAINED YEAR ROUND RESIDENCE AT SOUGHT AFTER HIGHLAND LAKE. 2 - STORY 4 BEDROOM, 3 BATH HOME OFFERS COMBINATION PICTURESQUE WATER VIEW PLUS DIRECT BEACH AREA WATER-FRONTAGE WITH DOCK & BOAT-LIFT. AWESOME CUSTOM DESIGNED CONTEMPORARY STYLE MASTER SUITE. 3 - ZONE HWBB OIL HEAT, CENTRAL AIR. OVERSIZE 2 CAR GARAGE. ALL ROOFING & VINYL SIDING IS 8 YEARS OLD. 10' X 10' REAR DECK INCLUDES UNDERNEATH ENCLOSED STORAGE AREA. HOUSE IS WIRED FOR GENERATOR. (GENERATOR DOES NOT REMAIN) THERE ARE NO DISCLOSURES FOR THIS PROPERTY. AT CLOSING SELLER WILL GIVE BUYER THE REQUIRED CREDIT OF $500.00. SEPARATE FROM THIS LISTED PROPERTY, THE OWNER HAS A WATERFRONT LOT (CTMLS LISTING #170225067) @ 538 W. WAKEFIELD BOULEVARD, AND A WATERVIEW LOT (CTMLS LISTING #170225075) @ 535 W. WAKEFIELD BOULEVARD EACH HAVING FULL APPROVALS WITH PLANS FOR THE CONSTRUCTION OF A SINGLE FAMILY HOME. SUBJECT PROPERTIES COULD MAKE FOR A UNIQUE FAMILY COMPOUND. OWNER WOULD BE OPEN TO A PACKAGE PRICE SALE FOR ADDRESSES 543, 538 AND 535 W. WAKEFIELD BOULEVARD."
* NEW LISTING 
$789,000
51 East Lake Street, Winchester CT 06098
6
BEDS
5
BATHS
3,888
SQFT
$203
$/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."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $795,000 TO $789,000 
$728,900
403 West Wakefield Boulevard, Winchester CT 06098
3
BEDS
2
BATHS
2,242
SQFT
$325
$/SQFT
0.56
ACRES
1981
BUILT
"Highland Lake Waterfront! Impeccably maintained, year-round waterfront home with upscale, multi-level floor plan features 120 feet of Waterfront and a Guest Cottage! The main home with 2,242 SF offers an open, bright L-shaped LR/DR with floor to ceiling Fireplace. Sunken Sunroom faces the backyard. Kitchen w/Breakfast Bar & plenty of cabinet space. Atriums to large, 28x16 Private Deck offers relaxing water views! Impressive Bath w/marble floors, marble counters w/ double sinks, sunken whirlpool tub, double shower enclosure & built in marble bench. Multi-level Master BR w/ vaulted ceiling, walk-in cedar closet, ductless A/C unit & Expansive windows for fabulous lake views. The fully finished, walk out lower level, with its built-in entertainment center, cedar pantry, fully tiled Bath with Shower, offers more living space or gives guests their own privacy! Spacious outbuilding. 2 car Garage w/newer doors (2016), Pella windows (2015), Driveway (2016), HW Heater (2014), Furnace (2014), 200 AMP service & more! The Guest cottage w/ its knotty pine interior couldn t be more charming w/ 352 SF, a Half Bath, Kitchen & Sliders to the expansive deck that cantilevers over the water. The cottage offers New Roof (2018), Gorgeous, panoramic views, Dock, lawn space & New Fence (2019). Public Sewer. Great lake location! Highland Lake is a fun, super clean recreational lake! 2HR to Boston/NYC, 45 min to Hartford. Close to the marina, fine eateries, the new Brewery & shopping"
$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."
$695,000
123 Ashley Road, Winchester CT 06098
3
BEDS
3
BATHS
2,812
SQFT
$247
$/SQFT
3.00
ACRES
2005
BUILT
"This beautiful Barn style Ranch sits on 3 acres of absolutely gorgeous private land with 250 feet of water frontage on Park Pond (an 82 acre getaway in the foothills of the Berkshires). This three bedroom Yankee Barn home built in 2005 is 2,812 finished square feet of living space in all. 2 custom built stone fireplaces to sit by and enjoy. Floating dock area with direct water access and sandy launch area for canoeing or kayaking. Lower level offers radiant heat with 10 foot ceilings and your guests own private quarters. Solar panels do wonders to offset the heating costs when the seasons change. Ample space for car enthusiasts or hobbyist with a 6 car heated garage and a lift! Perfect place to sit back relax and enjoy life. Priced to sell!"
* PRICE LOWERED - $749,500 TO $695,000 
$695,000
436 Winchester Road, Winchester CT 06098
3
BEDS
3
BATHS
2,881
SQFT
$241
$/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."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $745,000 TO $695,000 
$675,000
348 West Wakefield Boulevard, Winchester CT 06098
3
BEDS
2
BATHS
2,058
SQFT
$328
$/SQFT
0.08
ACRES
2002
BUILT
"Exceptional craftsmanship and stunning lake views in this immaculate custom built year round waterfront home. Built in 2002 this 3 bedroom, 2 full bath home makes entertaining a breeze with its thoughtful and open floor plan. An upscale kitchen with custom cabinets, limestone counter tops, a travertine backsplash, custom paneled refrigerator, center island with cook top and wall oven. The chef of the family gets to prepare while being able to socialize with guests and watch the boats cruise by. The dining room is nicely sized and is open to the living room with beautiful lake views with floor to ceiling Anderson windows, a fireplace for those chilly nights, surround sound, crown molding and a separate sitting/breakfast area with sliders leading to a 30 X 10 trex deck. Sit back and relax in the lounge chairs and take in the expansive views of the lake. The main floor has radiant heat and a full bath. The second floor master bedroom offers gorgeous views of the lake and is a wonderful retreat with gleaming hardwood floors, a fireplace and plantation shutters. Who doesn't want to wake up in the morning to that view!! The full bath is nicely sized and has Kohler fixtures, a large tiled shower and whirlpool tub. You won't be disappointed!! Two other bedrooms complete this home. A private level yard is perfect for a game of corn hole with family and friends. Approx 100 ft. of waterfront. This lake house is the ticket to the perfect oasis you've been dreaming of."
* PRICE LOWERED - $695,000 TO $675,000 
$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***"
* LISTED OVER 120 DAYS 
$630,000
714 West Wakefield Boulevard, Winchester CT 06098
3
BEDS
4
BATHS
2,400
SQFT
$262
$/SQFT
0.17
ACRES
2019
BUILT
"DON'T DELAY...Have input on the finishing touches! 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. You can select your cabinets, flooring, fixtures and more. This is a must see!! The home has an open floor plan with three levels. The main level consists of an open concept kitchen and living room, a combination mud room and half bath, as well as a master bedroom and bath overlooking the lake. The top floor has two bedrooms, both looking out over the lake, laundry, and a full bathroom. Lake life is made easier from this bottom floor family/rec room designed for easy access to the lake and made for entertaining with a kitchen and full bathroom. The spectacular views from nearly every room will say it all! Come take a look for yourself today! Owner/Agent related."
* PRICE LOWERED - $650,000 TO $630,000 
$622,120
120 Ashley Road, Winchester CT 06094
3
BEDS
3
BATHS
2,556
SQFT
$243
$/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."
* PRICE LOWERED - $639,900 TO $622,120 
$580,000
309 Colebrook Road, Winchester CT 06098
5
BEDS
2
BATHS
2,132
SQFT
$272
$/SQFT
160.00
ACRES
1903
BUILT
"NATURE LOVERS RETREAT! ENDLESS POSSIBILITIES! SECLUDED 160 acre mountain top nature sanctuary. Once a working cattle farm, the 160 mountain top acres are 90 % gently rolling, suitable for clearing and multiple uses. Included is a 13 room home, barn/lodge with huge fireplace, sheds, outbuildings and farm equipment! With old logging roads throughout and approx 20 acres of open fields the possibilities are endless. The abundance of wildlife, birds and butterfly's cannot be overstated on this nearly unspoiled land. The home 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 - $589,000 TO $580,000 
$575,000
87 East Lake Street, Winchester CT 06098
3
BEDS
2
BATHS
1,518
SQFT
$379
$/SQFT
0.11
ACRES
1920
BUILT
"Beautiful year round home on Highland Lake. You will not find many stylish renovated lake houses that give the WOW factor as soon as you open the door. Brazilian cherry floors throughout the first floor and a well equipped kitchen with soft washed look cabinetry, granite tile counters and excellent storage space. The open living room and dining room brings the waterfront, views and sunlight through. Sliders to a 26 foot deck is a great extension for enjoyment from the living room. A full bath and laundry complete this level. The second floor master has its own lake view balcony and ample closets and the tiled bath with shower is handsome with its tiled floor and skylight. There are two additional bedrooms with Brazilian cherry floors. The lower level has a family room with stone tile floor, track and recessed lighting. There are also storage areas and a mechanical room. A stone patio at this level meets a nice lawn with walk in access to the water. The aluminum dock is easy maintenance and in good condition. Central Air, Oil heat. Do not miss the opportunity to own on this clean hidden gem of a lake located at the foothills of the Berkshires. Highland Lake is a 444 acre boating lake, kayaking, paddle boarding, sailing and trophy fishing lake. 30 min. to Bradley International Airport, 20 minutes to Litchfield, 2 hrs. to NY & Boston. Fine restaurants, music venues, great shops and ski areas close by. It is a beautiful lake to enjoy all four seasons. Town water and sewer."
$575,000
878 West Wakefield Boulevard, Winchester CT 06098
4
BEDS
2
BATHS
2,490
SQFT
$231
$/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!"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $597,000 TO $575,000 
$569,900
848 East Wakefield, Winchester CT 06098
3
BEDS
2
BATHS
1,462
SQFT
$390
$/SQFT
0.13
ACRES
1964
BUILT
"Year round or 2nd home Direct waterfront 2 living levels, 2-3 bedrooms,2 full bathrooms 2 stone fireplaces. Lower level MBR suite w/full bath, it's own fireplace living area and access to waterfront patio. Main level kitchen with newer SS appliances overlooking sunken living room with double sliders to deck. Awesome views of entire lake, great waterfront with permanent boat dock (no in or out with the seasons) Shed for all the waterfront toys and 2nd shed on upper level. Ample parking for owners and quests. Short trip to Winsted/Torrington for shopping. 40 min to Bradley Airport and under 2 hours to NYC."
$559,120
120 Ashley Road, Winchester CT 06098
3
BEDS
3
BATHS
2,556
SQFT
$219
$/SQFT
10.00
ACRES
2005
BUILT
"Welcome to tranquil Winchester Center where time slows down to a peaceful pace is where you will find this true gem of a home nestled in the Litchfield Hills. Situated 300' from the road for privacy & seclusion! 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 throughout that include James Harde Plank siding, Arch. lifetime shingles, 2x6 Construction, structural laminate beams, footing drains, 1600sq ft stone patio overlooking the beautifully landscaped grounds & babbling brook, Marvin Integrity Low E Argon filled windows, over sized 3 car garage with 10' doors & 11' ceilings sure to accommodate your own collectibles/hobbies. 1000 gallon I/G propane tank, Central Air, Masonry 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/Chefs 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. Central Vac w/2 vacuum pans. Monitored Alarm & Fire System in place."
$519,000
39 East Lake Street, Winchester CT 06098
4
BEDS
2
BATHS
2,182
SQFT
$238
$/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 - $549,000 TO $519,000 
 
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