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!

174 Wallens, Winchester, CT 06098

MLS Number 170144140

  • Condo
  • Property Style Ranch
  • Bedrooms 1
  • Bathroom 2
  • Square Feet 1,334

Very well maintained one bedroom end unit which has been updated within the past 5 years. Features include, granite counters, gas heat, gas-fired fireplace, front porch, attached garage and wide enough driveway area to accommodate guests. Over 55 community.

Listing Courtesy of Borla & Associates LLC Real Estate

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Federal 30-year interest rate: 4.94% last updated on Nov 15, 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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72 Mountain, Winchester, CT 06098

MLS Number 170144069

  • Single Family
  • Property Style Colonial
  • Bedrooms 3
  • Bathroom 1
  • Acreage 0.3

Corner Lot, Three Bedroom Colonial on quiet street. Nice, spacious backyard with apple and pear trees. Fenced side yard.

Listing Courtesy of Sullivan Real Estate Inc

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Federal 30-year interest rate: 4.94% last updated on Nov 15, 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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146 Elm, Winchester, CT 06098

MLS Number 170144014

  • Rental
  • Property Style Colonial
  • Bedrooms 1
  • Bathroom 1
  • Acreage 0.24

Cute and clean 1 bedroom apartment. Off street parking for one car. Absolutley NO smoking and NO pets. Easy walk to downtown. Broker is owner

Listing Courtesy of Northwest CT Realty

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Federal 30-year interest rate: 4.94% last updated on Nov 15, 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 Pratt, Winchester, CT 06098

MLS Number 170144003

  • Rental
  • Property Style Colonial
  • Bedrooms 2
  • Bathroom 1
  • Acreage 0.17

Nice and clean 2 bedroom, first floor apartment. This apartment features large rooms, hardwood floors, gas fireplace in living room and includes washer and dryer in the basement. Available immediately. Absolutely NO pets and NO smoking. First and 1 month security.

Listing Courtesy of Northwest CT Realty

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$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 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

MLS Number 170143910

  • Rental
  • Property Style Colonial
  • Bedrooms 3
  • Bathroom 1
  • Acreage 0.26

Three bedroom, 2nd floor apartment. Living room, dining room, large kitchen and a mud room. Freshly painted, great front porch, close to college and town. Pets considered. Credit and background check required, $30 per person. First month and two months security unless over 62.

Listing Courtesy of The D'Amore Agency, LLC

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$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 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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50 Benton, Winchester, CT 06098

MLS Number 170143840

  • Multi Family Multi-Family For Sale
  • Bedrooms 6
  • Bathroom 2
  • Acreage 0.41
  • Square Feet 2,280

This well cared 2 family is located on a nice quiet street with an extra large level lot. Each unit has three bedrooms, large kitchens, living room and three bedrooms. The first floor is currently unoccupied and has brand new carpet and is ready for its new owner. Each unit has newer heating systems, their separate basements, separate driveways and entrance. Nicely landscaping and a great yard. There is a 20 year tenant on the second floor that would very much like to stay. Agent related.

Listing Courtesy of William Pitt Sotheby's Int'l

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$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 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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136 Meadow, Winchester, CT 06098

MLS Number 170143455

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 2
  • Acreage 0.25

This is a short sale. This is an older house in need of some TLC and upgrades. Bring your imagination.

Listing Courtesy of Realty Experts LLC

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$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 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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450 Platt Hill, Winchester, CT 06098

MLS Number 170143190

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 3
  • Acreage 2.75

Great opportunity to own in the Winchester Center area of Winsted. This 4 bedroom Colonial is central to Highland Lake, Winchester Lake and Park Pond. Enjoy almost 3 acres of lightly wooded privacy! Features hardwood floors thru out, Central air, Security system, Thermal paned windows, brand new drive way, New kitchen with granite counters and stainless steel appliances, Fireplaced living room, Master bedroom suite with full bath and walk-in closet, wired for generator, underground fence system for dogs, large back deck for entertaining! First floor bedroom or office 14x12. Bonus great room 26x14. Walk out basement ready to be finished to your liking! This home has it all! Many updated features:2 Newly installed top of the line central air systems with A/C units and air handlers,Premium Aztek maintenance free deck with techo block paver patio and stairs. Newer appliances and granite kitchen with induction stove , double ovens and pantry. Security system with cameras. Main floor office or bedroom. Nearby lot for sale for additional land.

Listing Courtesy of Hunter Real Estate, LLC

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$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 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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234 Oak, Winchester, CT 06098

MLS Number 170081381

  • Single Family
  • Property Style Colonial
  • Bedrooms 3
  • Bathroom 2
  • Acreage 0.28

Charming 3 bedroom, 2 bath Colonial with many updates. Beautiful front porch, new deck and private back yard. Large rooms, hardwood floors, new appliances, laundry on the main level, updated kitchen and baths.

Listing Courtesy of The D'Amore Agency, LLC

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$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 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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51 Elm, Winchester, CT 06098

MLS Number 170142247

  • Rental
  • Property Style Colonial
  • Bedrooms 2
  • Bathroom 1
  • Acreage 0.12

Bright and Sunny, 2nd floor 2 bedroom apartment with heat and hot water included. Off street parking, close to downtown. First month and two months security. No animals, no smoking. Credit and background check required, $30 per person.

Listing Courtesy of The D'Amore Agency, LLC

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$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 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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25 Griswold, Winchester, CT 06098

MLS Number 170117382

  • Single Family
  • Property Style Contemporary
  • Bedrooms 4
  • Bathroom 2
  • Acreage 0.65

WATER FRONT! 150" Are you looking for PARADISE? Well your search is over! Direct water front Lake Home on Winchester Fish and Game Club Pond! Coveted 30 acres. Spring and stream fed. Over 150' of lake front property. Not only is this a summer paradise but winter as well. The high elevation of 1170 feet lends itself to ice fishing, hockey and skating. Skiing is not far away as well. Small electric fishing motor allowed. No outside boats allowed to keep the lake from cross contamination. A new dam was built in 2011-2012. the house features, the first floor features Cathedral Ceiling Dining area with slider to deck. 2 story living room with wood stove, lots of windows and 2 sliders to large beautiful deck overlooking the lake and wooded yard, lots of privacy. A first floor bedroom and full bath. Upper level has a loft area to kick back on a rainy day and relax. Also a bedroom. Lower level features 2 additional bedroom, family room and full bath. Slider to lower deck. So come enjoy all that Mother Nature has to offer from Fire flies in July to Fall Foliage to Snow capped Mountains. It's all here for you! Right of first refusal and contingent upon Sellers finding a home of their choice. $1500 one time association fee and yearly association dues.

Listing Courtesy of William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 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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237 East Wakefield, Winchester, CT 06098

MLS Number 170141217

  • Rental
  • Property Style Hi-Ranch
  • Bedrooms 3
  • Bathroom 3
  • Acreage 0.28

This beautiful home features New Hardwood floors, Ledge Stone fire place, Granite and Marble counters tops, Large family room. Spacious Master bedroom suite with walk in closet, and custom bathroom. Lake rights and Boating rights. Oversize heated garage. Rent with option to buy. Heated garage. Must have good credit and good references.

Listing Courtesy of Better Living Realty, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 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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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.