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.

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538 Wheelers, Winchester, CT 06098

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

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$
$
%
$/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$949,000

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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Winchester, CT 06098

Price$850,000

Est. Mortgage: $/month

MLS Number 170012830

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

Have you dreamed of living "off the grid" or do you just love nature? Step into your back yard and hear the birds singing. Watch the bees and butterflies in the apple trees and garden. Enjoy the trails in the woods (on your horse, if you like), and the open pasture. This home, on 160 acres, could be your perfect, private getaway! Conveniently located to Route 44 and Route 8, the home offers 5 bedrooms, and vintage charm. There is also a separate cabin (currently used as a workshop and art studio), along with other smaller out-buildings. The property is powered by Solar panels, with the excess going back to the electric grid; which has generated a payment back to the owners, each year. The woods are ready to be logged again (last time was about 15 years ago). That could result in approx $40-50K of income. Income could also be derived from harvesting walnut trees and various species of burls, which are highly valued in high end carpentry ..... Almost the entire property is in PA 490, which results in the incredibly low Assessment and Taxes ..... Bring your imagination, and come see this stunning property! Reference Land listing MLS#170013381.

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$850,000

Est. Mortgage: $/month

MLS Number 170013381

  • Land
  • Acreage 160

Have you dreamed of living "off the grid" or do you just love nature? Step into your back yard and hear the birds singing. Watch the bees and butterflies in the apple trees and garden. Enjoy the trails in the woods (on your horse, if you like), and the open pasture. This home, on 160 acres (10+ acres is pasture), could be your perfect, private getaway! Conveniently located to Route 44 and Route 8, the home offers 5 bedrooms, and vintage charm. There is also a separate cabin (currently used as a workshop and art studio), along with other smaller out-buildings. The property is powered by Solar panels, with the excess going back to the electric grid. This has generated a payment back to the owners, each year. The woods are ready to be logged again (last time was about 15 years ago). That could result in approx $40-50K of income. Income could also be derived from harvesting walnut trees and various species of burls, which are highly valued in high end carpentry ..... 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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418 East Wakefield, Winchester, CT 06098

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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734 Lake, Winchester, CT 06098

MLS Number 170027956

  • Single Family
  • Property Style Cape Cod
  • Bedrooms 3
  • Bathroom 2
  • Acreage 0.44

This fabulous year round Cape home sits on the tip of Bartons Point at Highland Lake in Winchester Ct, one of the best western facing points on the lake. This home is on Lake Drive , one of the few private roads on the lake. Very private level lot with fencing and professional landscaping, plus over 100 feet of lakefront with a permanent 40 foot dock. This home is completely done and the perfect entertainment waterfront paradise, ready to move in and enjoyed this summer. Included are indoor and outdoor bars with refrigerators, ice makers and TV's. Huge custom made awning over the outdoor bar that makes for three season entertaining. Built in outdoor grille and burners adjacent to bar with granite surface plus a large patio and a built in fire-pit. Inside there are three generous size bedrooms. The huge master has a commanding view of the lake and the spectacular sunsets. The large guest room can easily sleep four and has a separate entrance via a spiral staircase. There are two full bathrooms. The large open floor plan includes a great room with a beautiful fireplace, a wall of windows plus two large bow windows all overlooking the lake. The entrance and wet bar have cathedral ceilings with skylights, track lighting, plus beautiful pine walls and ceilings. Home is equipped with a new security system with four cameras, a wireless thermostat. All controlled by your smart phone. Hot tub, pool table, eight skylights Rheem tankless water heater, central AC, central Vac and so much

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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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.

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25 East Lake, Winchester, CT 06098

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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405 West Wakefield, Winchester, CT 06098

MLS Number 170016587

  • Single Family
  • Property Style Contemporary
  • Bedrooms 2
  • Bathroom 3
  • Acreage 0.47

Highland Lake, a 444 acre body of water noted as one of the cleanest lakes in Connecticut. This year round one owner home has also been renovated with quality materials and finishes over the last few years. Stunning views from a newer Trex wrap around deck which overlooks a beautifully landscaped property and includes a spacious private waterfront with 115 feet, beach for launching your kyak or boat, a dock, entertaining area with patio and a cabana housing a bathroom, refrigerator and storage. A contemporary post and beam home with an Adirondack feeling in this open floor plan featuring a stone fireplace, vaulted ceiling and great floors and flows into the spacious dining area with access to the deck. Updated chef's kitchen has a 5 burner gas cook top, center island, pot rack and granite counters. An en suite first floor master bedroom and beautifully appointed bath with private deck. The second level bedroom has a full bath and office area. The finished walk out lower level (450+/- sq.ft) with 1/2 bath can be a third bedroom or game room and has lake views. The attached garage is deep and wide for cars with work area. CertainTeed siding, newer solar skylights, doors, 2017 roof and converted to propane heat. A generator is also included, lighting is built into stone walls, electric and water in the cabana and concrete sea wall. Buyers to assume balance of sewer assessment, approx. $2,900. Enjoy your summers or year round living at this most desirable lake.

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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118 Newfield, Winchester, CT 06098

Price$699,000

Est. Mortgage: $/month

MLS Number G10192293

  • Single Family
  • Property Style Antique, Victorian
  • Bedrooms 5
  • Bathroom 4
  • Acreage 8.12

Unbelievable price for this one of kind property! Enjoy the tranquility of this stately gentlemen's farm and horse property in historical Winchester Center. This 5 bedroom Victorian, built in 1903, is perched high on 8+ beautifully landscaped and exquisitely manicured acres which lends itself to the perfect summer retreat, weekend get-away or year round living. The formal living room, perfect for entertaining, has a lovely open floor plan with fireplace and uniquely designed hardwood floors. Cozy den with fireplace and large formal dining room also boast their own hardwood floor designs. The 4 bedrooms on second floor are beautifully appointed with lovely hardwood floors, and third floor is a confortable bedroom suite with full bath and lots of storage and built-ins. The mudroom area includes the laundry room and half bath along with an office or media room or small bedroom on its second level. Once a dairy farm, this property can easily be converted to an equestrian property with plenty of space in the carriage house, oversized peg and dowel barn and shed.

Listing Courtesy of Berkshire Hathaway NE Prop.

{$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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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.

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376 East Wakefield, Winchester, CT 06098

MLS Number 170021139

  • Single Family
  • Bedrooms 4
  • Bathroom 2
  • Acreage 0.3
  • Square Feet 1,878

DREAMING OF A LAKE HOUSE? - This charming renovated 4 BR home with 2 full baths sits on 91 feet of water frontage with its own private dock, sea wall and also has steps to enter the crystal clear water of Highland Lake. You can sit back , relax and enjoy drinks or your morning coffee on the large deck that boats scenic views of the lake surrounded by nature. An brick sidewalk leads the way to this most attractive home where you will find and an open floor plan with a spacious kitchen with built in hutch, dining room and family room with hardwood floors and sliders to the deck. Off the FR area is a dry bar. French doors open to the living room with hardwood floors, built in bookcases and a wood burning fireplace -perfect after a day of skiing, fishing or hiking. There is also a hot tub room with great views of the lake as well as a first floor bedroom and a full bath. The knotty pine walls lend a woodsy country touch to this wonderful home. The second floor is an open area with three skylights and is used as a gaming room with an office overlooking the lake. A master bedroom with stunning lake views and 2 additional bedrooms complete this level. A full walkout basement and two car detached garage offer plenty of space for storing your canoe, kayak or floats. You can gather around a fire pit after a day on the lake or sit by the fireplace after an autumn hike in the mountains. Highland Lake is 444 acres nestled in the Berkshires. 2 hrs to NYC and 20 min to Mass.

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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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.