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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!

120 Torringford, Winchester, CT 06098

Price$249,900

Est. Mortgage: $/month

MLS Number 170106853

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 2
  • Acreage 12.35

Once the Formica Farm, this 1838 Colonial sits on 12 acres with scenic views over the city and reaching to the west towards Norfolk. There is much potential for the acreage to be used for farming, horses, Christmas trees or even a small subdivision and has frontage on Torringford St and Moore Ave. The home has 10 rooms and up to 5 bedrooms and is serviced by public water and sewer. The lower level is partially finished and has a walk in cooler. Conveniently located with easy access to Rte 8 and 44 and nearby shopping. Owner owns abutting property which is also available for sale (170095436) and is willing to make a package deal.

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: 4.53% last updated on Jul 12, 2018
* 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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151 Newfield, Winchester, CT 06098

Price$114,500

Est. Mortgage: $/month

MLS Number 170106748

  • Single Family
  • Property Style Cape Cod
  • Bedrooms 2
  • Bathroom 1
  • Acreage 0.35

Cute Cape Cod home nestled atop of Newfield Road, offering over 1200 square feet with 2 bedrooms and 1 bathroom. Room first floor with large living room with a nice fireplace to enjoy. Kitchen flows into the dining area. Full basement for added storage and detached garage is roadside. Make sure to schedule your showing today!

Listing Courtesy of Silver and Oak 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: 4.53% last updated on Jul 12, 2018
* 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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139 North Main, Winchester, CT 06098

Price$44,900

Est. Mortgage: $/month

MLS Number 170071810

  • Multi Family Multi-Family For Sale
  • Bedrooms 7
  • Bathroom 3
  • Acreage 0.26
  • Square Feet 2,118

There is much potential to turn this three family house into a money maker for you! Located across the street from Northwest Community College. Metal roof. This is a Fannie Mae HomePath property.

Listing Courtesy of RE/MAX Premier REALTORS

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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: 4.53% last updated on Jul 12, 2018
* 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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35 Woodruff, Winchester, CT 06098

Price$129,900

Est. Mortgage: $/month

MLS Number 170106234

  • Single Family
  • Property Style Colonial
  • Bedrooms 3
  • Bathroom 1
  • Acreage 0.28

Lots of updating done to this very affordable home located on the very quiet street. There is a large backyard which extends all the way back to the next street. New floors, tall ceilings, and lots of light. Solid and level move in ready home with lots of work done in the past two years.

Listing Courtesy of Realty Experts LLC

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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: 4.53% last updated on Jul 12, 2018
* 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$350,000

Est. Mortgage: $/month

MLS Number 170102797

  • Land
  • Acreage 98

Charming and rural Winchester! 98 acres with potential distant views! Surveyed and tested several years ago.

Listing Courtesy of The D'Amore Agency, LLC

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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: 4.53% last updated on Jul 12, 2018
* 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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178 Boyd, Winchester, CT 06098

Rental Price$895

MLS Number 170075637

  • Rental
  • Property Style Half Duplex
  • Bedrooms 2
  • Bathroom 1
  • Acreage 0.1

Totally remodeled duplex with lake views. Two bedrooms, laundry hook-ups, new kitchen, high ceiling and new windows. Pets considered. Credit and background check done by listing office.

Listing Courtesy of The D'Amore Agency, LLC

{$office->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: 4.53% last updated on Jul 12, 2018
* 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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45 Willow, Winchester, CT 06098

Price$12

MLS Number 170105675

  • Commercial Lease Commercial For Lease
  • Acreage 0.53
  • Square Feet 9,438

Property is visable from route 44 (aka main street) and fronts on willow street. Facility has been both an auto dealer & a boat dealer. Property would need alterations and upgrades to accomodate new tenants. Building has a total of 12 hver-head doors. Owner would work with tenant to accomodate upgrades and alterations. Building could be leased in it's entirety or sub-divided to individual tenants.

Listing Courtesy of Cohen Agency

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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: 4.53% last updated on Jul 12, 2018
* 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

139 Grantville, Winchester, CT 06098

Price$3,295,000

Est. Mortgage: $/month

MLS Number 170105658

  • Single Family
  • Property Style Colonial
  • Bedrooms 3
  • Bathroom 3
  • Acreage 419.09

Stunning land. 419 +- acres of rolling, open, flat, treed land. House is in need of renovation or removal and is sold as is. Call or email listing agent for all info.

Listing Courtesy of William Pitt Sotheby's Int'l

{$office->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: 4.53% last updated on Jul 12, 2018
* 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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12 Chestnut, Winchester, CT 06098

Price$159,900

Est. Mortgage: $/month

MLS Number 170105628

  • Single Family
  • Property Style Ranch
  • Bedrooms 3
  • Bathroom 2
  • Acreage 0.15

This 1982 Ranch is in excellent condition. On the main level there are 3 modest size bedrooms, kitchen, living room with fireplace, full bath and access to a private deck. The upper level contains a suite with full bath.This space could suit many purposes. You can't find a more convenient location to shopping, restaurants and anything downtown than this.

Listing Courtesy of Northwest CT Realty

{$office->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: 4.53% last updated on Jul 12, 2018
* 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

41 Perkins, Winchester, CT 06098

Price$100,000

Est. Mortgage: $/month

MLS Number 170105602

  • Single Family
  • Property Style Ranch
  • Bedrooms 2
  • Bathroom 1
  • Acreage 0.19

Quaint home in a quiet neighborhood. Close to everything. Perfect starter home or ready for the down-size. Freshly painted. New hot water heater. New Roof. Replacement windows. Newer furnace and oil tank. FHA compliant. Bring your buyers - this house is ready for its next owners!

Listing Courtesy of Integrity Real Estate

{$office->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: 4.53% last updated on Jul 12, 2018
* 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

28 Maloney, Winchester, CT 06098

Price$124,900

Est. Mortgage: $/month

MLS Number 170105456

  • Single Family
  • Property Style Cape Cod
  • Bedrooms 3
  • Bathroom 2
  • Acreage 0.21

Vinyl Sided 3-4 Bedroom Cape has new Carpeting in all bedrooms , Entire interior repainted , New Kitchen and new Full bath on first floor and 2nd floor . New Furnace .THERMO PAINE WINDOWS . 14 x 30 fireplaced living room dinning room combo with hardwood floors . neighborhood playground and EZ access to Shopping and recreation . .Elevated fireplaced front patio plus a 2nd fireplaced rear pation ideal for cookouts . Many inprovements due to recent fire .

Listing Courtesy of The D'Amore Agency, LLC

{$office->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: 4.53% last updated on Jul 12, 2018
* 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

139 Grantville, Winchester, CT 06098

Price$3,295,000

Est. Mortgage: $/month

MLS Number 170104937

  • Land
  • Acreage 412.09

Stunning land - 412+ acres - in lovely Winchester. 5,614 feet of frontage. Open meadows and treed areas with stone walls and a part of the Mad River and a pond. Sub-dividable. House on property is as is. House is winterized. Magical. Sotheby's agent will accompany.

Listing Courtesy of William Pitt Sotheby's Int'l

{$office->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: 4.53% last updated on Jul 12, 2018
* 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.