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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. If you are interested in any particular property, contact us! We are happy to answer any questions you may have. To save yourself time, register with the site to save your favorite properties and searches. If you already have an account, feel free to sign in!

538 Wheelers, Winchester, CT 06098

Price$1,200,000

Est. Mortgage: $/month

MLS Number 170006285

  • Single Family
  • Property Style Farm House, Tudor
  • Bedrooms 3
  • Bathroom 3
  • Acreage 0.7

Create your legacy here!!! Located on a very private lot that boasts over 360' of waterfront at the end of the prestigous peninsula of Wheelers Point sits this Tudor style Farmhouse. This property offers an abundance of features that will make you feel like you're on vacation from the moment you rise wether your are inside or out. From the moment you walk thru the entryway you will know that you are in a very special place. The home features a lot of old world character with modern conveniences with 3 modest bedrooms and 3 full baths. There is a large cedar deck overlooking the panoramic waterfront, multiple (4+) vessel docking area and private sandy beach/swimming area.

Listing Courtesy of Northwest CT Realty

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The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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

Price$1,190,000

Est. Mortgage: $/month

MLS Number 170072808

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

Rare opportunity to own one of highland lakes gems. Pine knoll is an amazing and classic, updated turn key waterfront home located on the crested area of a peninsula. Beautiful views from every window, most with water view. Sale includes private island, 2 docks, extensive landscaping, most furnishings and water toys including boats. Plenty of room to expand if needed in walk-up attic area. Recent updates include kitchen with granite, spa quality full bath on the first floor, hardwood, and beautiful mill work on exterior windows. Enjoy long lazy summer days on the expansive wraparound deck and sweeping covered front porch. One look and your home all you need to do is unpack.

Listing Courtesy of Berkshire Hathaway NE Prop.

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The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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$1,049,000

Est. Mortgage: $/month

MLS Number 170074186

  • Single Family
  • Property Style A-Frame, Chalet
  • Bedrooms 6
  • Bathroom 6
  • Acreage 0.7

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

Listing Courtesy of Northwest CT Realty

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The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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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129 East Lake, Winchester, CT 06098

Price$919,000

Est. Mortgage: $/month

MLS Number D10228700

  • Single Family
  • Property Style Colonial
  • Bedrooms 3
  • Bathroom 4
  • Acreage 0.6

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

Listing Courtesy of Higgins Group

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The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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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418 East Wakefield, Winchester, CT 06098

Price$849,900

Est. Mortgage: $/month

MLS Number 170001024

  • Single Family
  • Bedrooms 6
  • Bathroom 3
  • Acreage 0.7
  • Square Feet 3,020

Enjoy Highland lake views from most rooms in this beautifully renovated ten room year round direct waterfront home. The cook's kitchen has custom shaker cabinetry, granite, all the bells and whistles and opens to the spacious dining room with built-in cabinetry, two bay windows and access to the upper level deck for outdoor dining. A stone fireplace is the focal point of the living room with access to a 3 season enclosed porch and more water views. A first floor bedroom with newer bathroom, family room and laundry complete the first floor. On the second level are five more bedrooms and two updated full baths all attractively done. Also a study or office on the second level with a large heated room that can be used for many things. Mechanically, the house has C/A multi-zone Buderis newer furnace & hot water heater. A whole house generator, newer roof and windows, well and public sewer are assets to this fine property. Not only is this home charming and updated, there are expansive views and sun all day on the desirable east side of this pristine 444 acre lake in the Berkshire Mountains of Litchfield County. The mahogany decks have lighting, outdoor speakers, 105 ft. of waterfront . Lots of privacy, beautiful perennials and great parking with its two garages. Enjoy ice fishing in the winter, boating in the summer and the beautiful foliage in the fall. Great skiing, hiking in nearby towns. Less than 2 hrs. to NYC. Come see "Lake Haus"-we have a seat on the deck for you!

Listing Courtesy of William Pitt Sotheby's Int'l

{$agent->Name}

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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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Winchester, CT 06098

Price$798,000

Est. Mortgage: $/month

MLS Number 170013381

  • Land
  • Acreage 160

Step away from the pressure of city life and enjoy your own enchanted retreat. Just minutes from schools and entertainment, in Winsted, CT, and less than 2.5 hours to either NYC or Boston, this 5 bedroom home on 160 lush acres, could be your perfect private getaway. This vintage charmer is conveniently located to Route 44 and Route 8; is backed by state land and a breathtaking pond; and also offers a separate dwelling, currently used as a workshop and art studio, along with other smaller out-buildings. Approximately 20 acres of beautiful, gently sloping fields, provide opportunity to keep horses, if you wish; or just enjoy nature all around you, easily accessed by the old logging trails through the woods ..... Almost the entire parcel is in PA 490, which results in the incredibly low assessment and taxes ..... Bring your imagination, and come see this stunning property! Reference Residential listing MLS#170012830

Listing Courtesy of Integrity Real Estate

{$agent->Name}

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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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Winchester, CT 06098

Price$798,000

Est. Mortgage: $/month

MLS Number 170012830

  • Single Family
  • Property Style Farm House
  • Bedrooms 5
  • Bathroom 3
  • Acreage 160

Step away from the pressure of city life and enjoy your own enchanted retreat. Just minutes from schools and entertainment, in Winsted, CT, and less than 2.5 hours to either NYC or Boston, this 5 bedroom home on 160 lush acres, could be your perfect private getaway. This vintage charmer is conveniently located to Route 44 and Route 8; is backed by state land and a breathtaking pond; and also offers a separate dwelling, currently used as a workshop and art studio, along with other smaller out-buildings. Approximately 20 acres of beautiful, gently sloping fields, provide opportunity to keep horses, if you wish; or just enjoy nature all around you, easily accessed by the old logging trails through the woods ..... Almost the entire parcel is in PA 490, which results in the incredibly low assessment and taxes ..... Bring your imagination, and come see this stunning property! Reference Residential listing MLS#170012830

Listing Courtesy of Integrity Real Estate

{$agent->Name}

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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

276 Pratt, Winchester, CT 06098

Price$769,000

Est. Mortgage: $/month

MLS Number 170046457

  • Single Family
  • Property Style Colonial, Antique
  • Bedrooms 3
  • Bathroom 3
  • Acreage 77.9

Do come and visit this quintessential 1760 Connecticut farmhouse and its recent additions for today's lifestyle. The home is set high on 77.9 acres, allowing for expansive vistas of perennial gardens, meadows, woodlands and hills beyond. Situated in Litchfield County close to Highland Lake makes it a wonderful weekend retreat or year-round home. The property could well become a fabulous equestrian estate with paddocks, meadows and private trails. Don't miss the opportunity to make this special property your own!

Listing Courtesy of Halstead Property

{$agent->Name}

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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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167 West Wakefield, Winchester, CT 06098

Price$759,000

Est. Mortgage: $/month

MLS Number 170072831

  • Single Family
  • Property Style Contemporary
  • Bedrooms 3
  • Bathroom 2
  • Acreage 1.4

The panoramic view from the deck of this custom Lindell Cedar home allows views of First bay through the first narrows into Second Bay and into Third Bay. You will receive sunshine from sunrise till sundown. Set on over 200' of waterfront that allows for multiple docking positions. This home features two main level bedrooms along with an open kitchen, dining and main living area with cathedral ceilings and wall of windows with the same panoramic view as the deck The second floor contains the master suite with master bath and walk in as well as a loft area for den or office.The lower level offers approximately 600 square feet of expandable living space with walkout to the waterfront. Need space to park the toys, there is an oversized three bay heated garage with expandable second floor. Highland lake is a 444 acre lake and is noted for its clean water, one of the reasons is this property along with 95% of the properties on the lake are connected to city sewer. Just 45 minutes to Hartford and Bradley International Airport. The Berkshires are very close by as well as Infinity Music Hall and Warner Theater. 2 hrs. To NYC and 2/12 to Boston.

Listing Courtesy of Northwest CT Realty

{$agent->Name}

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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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25 East Lake, Winchester, CT 06098

Price$750,000

Est. Mortgage: $/month

MLS Number L10206319

  • Single Family
  • Property Style Cape Cod
  • Bedrooms 4
  • Bathroom 5
  • Acreage 0.74

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

Listing Courtesy of The D'Amore Agency, LLC

{$agent->Name}

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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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Winchester, CT 06098

Price$750,000

Est. Mortgage: $/month

MLS Number L10231514

  • Land
  • Acreage 104

104 acres available in charming and rural Winchester. Testing done approximately 10 years ago for 24 lots. Test Info, maps available. Currently in Forestry.

Listing Courtesy of The D'Amore Agency, LLC

{$agent->Name}

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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

760 Lake, Winchester, CT 06098

Price$695,000

Est. Mortgage: $/month

MLS Number L10231012

  • Single Family
  • Property Style Colonial
  • Bedrooms 3
  • Bathroom 3
  • Acreage 0.2

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.

Listing Courtesy of Town & Country Real Estate

{$agent->Name}

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Dec 21, 2017
* 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.