Winchester CT Real Estate

The town of Winchester, also known as the Gateway to the Berkshire Mountains, offers a good quality of life with beautiful lakes and plenty of recreational activities. Popular activities include swimming, fishing, boating, and water skiing. The Winchester Business Park is home to many merchants and manufacturers. Browse all real estate and homes for sale in Winchester, CT below. 

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210-212 West Wakefield Winchester CT 06098

MLS Number 170177145

  • Single Family
  • Property Style Other
  • Bedrooms 11
  • Bathroom 9
  • Acreage 1.17

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**

Listing Courtesy of Berkshire Hathaway NE Prop.

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$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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211/212 West Wakefield Winchester CT 06098

MLS Number 170177142

  • Single Family
  • Property Style Colonial, Other
  • Bedrooms 5
  • Bathroom 6
  • Acreage 1.05

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.

Listing Courtesy of Berkshire Hathaway NE Prop.

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$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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132 Spencer Hill Winchester CT 06098

MLS Number 170207910

  • Land
  • Acreage 82

Very special land parcel. Western views overlooking Highland Lake. Pastures, fields, stone walls, brook & wooded areas showcase this wonderful building site. Ideal single family or subdivision potential. Land is actual several parcels on both Spencer Hill Rd and Spencer St totaling 81 +/- acres, Sewer & water nearby, but not yet permitted.

Listing Courtesy of William Pitt Sotheby's Int. Re

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$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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406 East Wakefield Winchester CT 06098

MLS Number 170209084

  • Single Family
  • Property Style Contemporary
  • Bedrooms 4
  • Bathroom 3
  • Acreage 0.92

Welcome to Eagle Point, sited on a private location on Highland Lake noted for its clean water. Pretty places to gather guests start at the deck. The nearby stone patio offers an outdoor dining area. The lawn is lush and is the perfect place for a game of corn hole. Guests and family will want to wander down to the shoreline and sit back in the shaded lounge area and take in the magnificent views of the lake. Beautiful renovation of this year round 4 bedroom, 3 full bath waterfront home began in 2015 and is situated in the heart of the Litchfield Hills at the gateway to the Berkshires in one of the most scenic sections of Connecticut. As you enter the mudroom with white washed brick floor you will fall in love with this special year round home. The kitchen is spacious and will remain unfinished so the buyer(s) can finish to their liking. The kitchen is enhanced by one wall of beautiful stone and local wide board pine floors. A walk in pantry is a bonus to the chef of the family and there is also a breakfast/dining area off the kitchen. The living room with its large windows provides peaceful and panoramic views of the lake and the mountains. Step out on the pressure treated deck and hear the sounds of nature - you are sure to spot the eagle landing in the tree as well as blue heron gliding across the lake. The family room is located off the kitchen and has a cathedral ceiling, stunning two story stone fireplace with sliders to the patio and lake views.

Listing Courtesy of William Pitt Sotheby's Int'l

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$
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$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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534 Wheelers Winchester CT 06098

Price$910,000

Est. Mortgage: $/month

MLS Number 170108797

  • Single Family
  • Property Style Cape Cod
  • Bedrooms 3
  • Bathroom 2
  • Acreage 0.54

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.

Listing Courtesy of William Pitt Sotheby's Int'l

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$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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28 South Main Winchester CT 06098

MLS Number 170215824

  • Commercial
  • Acreage 1.25
  • Square Feet 8,457

These 6 contiguos properties located on busy Ete.# 44 are being sold as a package , not individually and are located in TG zone

Listing Courtesy of The D'Amore Agency, LLC

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$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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28-44 South Main Winchester CT 06098

MLS Number 170215808

  • Single Family
  • Property Style Colonial
  • Bedrooms 18
  • Bathroom 8
  • Acreage 1.25

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

Listing Courtesy of The D'Amore Agency, LLC

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$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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504 West Wakefield Winchester CT 06098

MLS Number 170178210

  • Single Family
  • Property Style Contemporary, Ranch
  • Bedrooms 3
  • Bathroom 3
  • Acreage 0.57

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.

Listing Courtesy of Northwest CT Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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262 Perch Rock Winchester CT 06098

Price$820,000

Est. Mortgage: $/month

MLS Number 170193205

  • Single Family
  • Bedrooms 7
  • Bathroom 5
  • Acreage 0.24
  • Square Feet 4,416

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

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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543 West Wakefield Winchester CT 06098

MLS Number 170225059

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 3
  • Acreage 1

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.

Listing Courtesy of Cohen Agency

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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51 East Lake Winchester CT 06098

Price$789,000

Est. Mortgage: $/month

MLS Number 170157342

  • Single Family
  • Property Style Contemporary
  • Bedrooms 6
  • Bathroom 5
  • Acreage 0.7

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.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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147 Torrington Winchester CT 06098

MLS Number 170221311

  • Commercial
  • Acreage 7
  • Square Feet 7,300

Previous use was Sports Complex/Dome. Unlimited uses to consider. 7,300 sq foot (50 x 146 ) Steel frame construction with ample parking and high traffic count. Turn key operation for Construction Company/Fuel Company/Automotive, bring your imagination...

Listing Courtesy of The D'Amore Agency, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Information contained in this Smart MLS listing has been compiled from various sources, all of which may not be completely accurate. Smart MLS makes no warranty or representation as to the accuracy of listing information. All information that influences a decision to purchase a listed property should be independently verified by the purchaser. Copyright 2017 Smart MLS, Inc. All rights reserved.