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!

143 Meadow, Winchester, CT 06098

MLS Number 170122857

  • Single Family
  • Property Style Colonial
  • Bedrooms 3
  • Bathroom 3
  • Acreage 0.26

Three Bedroom , 2 bath 1823 colonial with front porch and on level centrally located parcel . In past 5-6 years , new furnace and updated Kitchen & baths. .Hardwood floors .

Listing Courtesy of The D'Amore Agency, LLC

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Federal 30-year interest rate: 4.65% last updated on Sep 20, 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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17 Rowley, Winchester, CT 06098

MLS Number 170127452

  • Commercial
  • Square Feet 6,300

2 story free standing local, long time quality dining favorite says “Time To Sell”. Once in a lifetime opportunity to carry on a tradition. Affluent vacationers as well as dedicated local customers are ready for an update to the concept. Restaurant for sale also for $125,000. Market value for this property is $477,100. Facilities: 6,300 sq. ft. built in 2005, CB 2 Zone well and septic, Natural Gas, 2nd floor storage with bathroom. Land 0.68 acres great universal parking. Restaurant seating bar and lounge -26, dining 55, well appointed Chef's Kitchen with 16' hood.

Listing Courtesy of Commercial Services Realty

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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 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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23 Wetmore, Winchester, CT 06098

MLS Number 170118225

  • Rental
  • Property Style Colonial
  • Bedrooms 2
  • Bathroom 1
  • Acreage 0.18

Immaculate owner's unit, recently completely and tastefully renovated, super clean and bright. Top floor, spacious layout. 2 bedroom, hardwood floors and tile throughout. Glass shower, pet may be considered. Small sewer and water fee quarterly of $33.00 per month additional. Washer and Dryer in unit. All brand new appliances, gas range. Off street parking for the inclement weather. Landlord takes care of snow/ice/lawn and maintenance. Looking for long term professionals. Credit and back ground check, use brokers application. $40.00 credit and background fee non-refundable. First month's rent and 2 months security if applicable. First time offered for rent, you definitely don't want to miss this rental!

Listing Courtesy of Turning Point Realty, LLC

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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 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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85 Lake, Winchester, CT 06098

Price$129,900

Est. Mortgage: $/month

MLS Number 170127226

  • Single Family
  • Property Style Other
  • Bedrooms 3
  • Bathroom 2
  • Acreage 0.32

Located in the heart of Winchester, this beautiful home is walking distance from downtown, the boat launch and beach! Freshly painted and kitchen has new kitchen countertops and backsplash. The deck is great for entertaining. Three bedrooms and two full bathrooms. Washer and dryer hookups on main level. Hardwood and carpet throughout... MUST SEE!

Listing Courtesy of Cohen Agency SiM, LLC

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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 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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521 East Wakefield, Winchester, CT 06098

MLS Number 170112143

  • Single Family
  • Property Style Ranch
  • Bedrooms 2
  • Bathroom 1
  • Acreage 0.27

Enjoy your summers on the lake or live here all year long and enjoy all 4 seasons! Deeded access to the lake with boat mooring. This adorable 5 room ranch is off the main road offering privacy and has an open floor plan with updated kitchen and bath. The dining room has 2 walls of sliders allowing a beautiful view while you dine. Outdoors you'll find a good sized yard, 2 patios, a deck and just a very short walk to the lake. There is a detached 2 car garage, with storage, and a large area for plenty of parking.

Listing Courtesy of The Washington Agency

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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 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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55 Hurlbut, Winchester, CT 06098
Pending

MLS Number 170123261

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 1
  • Acreage 0.91

Spacious vinyl sided Colonial located 2/10th of a mile from Highland Lake and the public beach! Featuring 4 bedrooms, generous kitchen, sun room and wood floors through out. Nice sized deck overlooking the back yard. All situated on almost 1 acre.

Listing Courtesy of Northwest CT Realty

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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 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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97 Spencer Hill, Winchester, CT 06098

MLS Number 170093232

  • Single Family
  • Property Style Split Level
  • Bedrooms 2
  • Bathroom 1
  • Acreage 1.98

Nicely maintained and ready to move in Split-level located on the edge of city limits. Easy to get to conviences yet the quite of the country. This home features hardwood floors in the bedrooms and in the large dining area that is completely open to the living room with access to the private covered deck overlooking the rear yard. The kitchen provides plenty of counter and cooking space. In the walk out basement there is a laundry room, workshop and space for a rustic man cave. The large back yard provides many options for gardening and tucked back in the wooded area is a stand of ancient apple trees that still produce fruit.

Listing Courtesy of Northwest CT Realty

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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 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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295 Torringford, Winchester, CT 06098

MLS Number 170125821

  • Single Family
  • Property Style Ranch, Split Level
  • Bedrooms 3
  • Bathroom 2
  • Acreage 1.2

Must See...Uniquely Designed 3 Bedroom 2 Bathroom Ranch that has multiple split levels for an open plan airy feel. Located directly across the way you will find beautiful views of Green Woods Golf Course. This property also has a nice ample size lot of 1.2 acres... The property is in overall very good move in condition and with some aesthetic updating the home is truly a potential gem. The fire placed living room along with a family room and large den offers plenty of extra square footage to spread out and relax. All offers will move quickly and are subject to probate approval.

Listing Courtesy of Town & Country Real Estate

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$
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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 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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7 Stadler, Winchester, CT 06098

Price$150,000

Est. Mortgage: $/month

MLS Number 170125905

  • Land
  • Acreage 20.87

Perfect for an outdoor lifestyle, sportsmen or nature lover! Private setting, private road - last lot in an 8-lot subdivision. Homesite has been cleared and processed gravel driveway to clearing has been installed. Eastern view potential. Hike or cross-country ski right out your door. Meandering path leads to a brook. Abundant wildlife. Property is close to Greenwoods Country Club, West Hill and Routes 183, 44, 202. Schools: Batcheler (K1), Hinsdale (2-4), Pearson (5-6), Gilbert (7-12). *Gas line easement to rear of property is accessible on West Hill Road.*

Listing Courtesy of Marrin Santore Realty LLC

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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 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 East Lake, Winchester, CT 06098

MLS Number 170125664

  • Single Family
  • Property Style Colonial
  • Bedrooms 3
  • Bathroom 3
  • Acreage 0.55

Magnificent waterfront home on over 150' of shore on Highland Lake. This immaculate home sits pretty on a spacious flat property in first bay, with plenty of room for gatherings, outdoor activities, and a large driveway with ample parking space and more room for play! There is a large deck overlooking the lake with a large retractible awning to provide some late day shade. Both the main living level and upper floor bedrooms are adorned with Brazilian Teak wood flooring. The unique layout of the land allows for a super shallow area along the seawall perfect for wading and small children. The dock is located in deeper water so you can dive from there, there is a boat slip and jet ski mooring. Roast marshmallows over the fire pit in the evening and be the last home on the lake to watch the sun go down- this location really is the best! Highland lake is a 444 acres 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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 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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37 Case, Winchester, CT 06098

MLS Number 170125582

  • Rental
  • Property Style Colonial
  • Bedrooms 3
  • Bathroom 1
  • Acreage 0.14

Large, first floor, 3 bedroom with washer dryer hook-up in the unit. Large backyard and garage, off street parking. First month and 2 month's security. Credit and background check required.

Listing Courtesy of The D'Amore Agency, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 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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32 Riveredge, Winchester, CT 06098

MLS Number 170125393

  • Condo
  • Property Style Townhouse
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 992

Stunning condo newly renovated! Tucked away in a secluded little complex this unit shines! A must see!

Listing Courtesy of Classic Real Estate LLC

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$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 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.