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: 3.75% last updated on Jul 11, 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: 3.75% last updated on Jul 11, 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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512 West Wakefield Winchester CT 06098

MLS Number 170177137

  • Single Family
  • Property Style Victorian
  • Bedrooms 3
  • Bathroom 2
  • Acreage 0.86

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*

Listing Courtesy of Berkshire Hathaway NE Prop.

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$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 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: 3.75% last updated on Jul 11, 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$949,500

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: 3.75% last updated on Jul 11, 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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850 East Wakefield Winchester CT 06098

MLS Number 170177978

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 3
  • Acreage 0.43

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)

Listing Courtesy of William Pitt Sotheby's Int'l

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$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 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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424 East Wakefield Winchester CT 06098
Pending

MLS Number 170176483

  • Single Family
  • Property Style Victorian
  • Bedrooms 5
  • Bathroom 2
  • Acreage 0.59

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

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 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$869,000

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: 3.75% last updated on Jul 11, 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: 3.75% last updated on Jul 11, 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: 3.75% last updated on Jul 11, 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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123 Ashley Winchester CT 06098

Price$749,500

Est. Mortgage: $/month

MLS Number 170210594

  • Single Family
  • Property Style Ranch
  • Bedrooms 3
  • Bathroom 3
  • Acreage 3

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!

Listing Courtesy of Century 21 AllPoints Rlty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 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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422 East Wakefield Winchester CT 06098

MLS Number 170103261

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 3
  • Acreage 0.48

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.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 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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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.