The Matthews Team

William Raveis Lifestyles Realty

Winchester - Winsted 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. 

Winchester Real Estate

Contact the William Raveis Lifestyles Team at 860-868-0511 with any questions or to schedule a private tour.

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111 Riverton Road Winchester CT 06098

Winchester, CT111 Riverton Road

Price$158,000

Est. Mortgage: $/month

MLS Number 170538094

  • Condo
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 1,204

The condo has been Freshly painted features Stainless Steel Kitchen Appliances. New Carpeting, New Energy efficient Windows & Sliders! Open Living Room and Dinning Area with Fire Place. Second level features the Bedrooms, Bath with skylight. Just bring your belongings! A must see!! Being sold "AS IS" inspections are for informational purpose.

Listed by Linda Ganem of Borla & Associates LLC Real Estate

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$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* 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 Avenue Winchester CT 06098

Winchester, CT23 Wetmore Avenue

Price$299,000

Est. Mortgage: $/month

MLS Number 170538044

  • Multi Family Multi-Family For Sale
  • Square Feet 3,303
  • Acreage 0.18

Immaculate fully rented 3 family. First floor unit is rented through 2024 and has two bedrooms, full bath, washer/dryer in basement, kitchen has newer dishwasher, refrigerator and gas range. Walk in pantry, dining room and living room, hardwood floors with sitting area, and front porch. Second floor has two bedrooms full bath, washer/dryer in kitchen, with large walk-in pantry, unit also has newer refrigerator and gas range, dining room with built-in china closet and large living room as well as private second story front porch as well as rear porch and hardwood floors. Third floor unit has two bedrooms, a galley kitchen full bath, large living room and hardwood floors. Desirable neighborhood and large level lot. All units have been fully updated since 2016. Detached 2 car garage, paved shared driveway. Close to college shopping restaurants and Rt 8 South. Broker and Owner related.

Listed by Suzie Larson of Turning Point Realty,LLC

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$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* 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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228 Holabird Avenue Winchester CT 06098

MLS Number 170538355

  • Single Family
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 2,150
  • Acreage 0.27

Modest in town 4 bedroom Colonial with 4+ car garage. The main living level features a large kitchen with adjacent pantry and laundry area, formal dining room, large living room and attached den/family room with the ability for a wood stove. The upper level contains 4 large bedrooms and a full bath. The walk up attic has room for plenty of storage and a semi finished room for an office or such. Mechanical features are an automatic transfer whole house generator, two oil storage tanks and an updated boiler. The over size garage has room enough for all your toys or will make a really nice workshop.

Listed by David Sartirana of Northwest CT Realty

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$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* 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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155 West Road Winchester CT 06098
Active With Contract

MLS Number 170537908

  • Single Family
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,608
  • Acreage 2.05

Directly across from 246 acre Winchester lake. Great views and lake access, just walk across the street. Single level country ranch house in great shape with numerous updates, mature plantings, private deck with outdoor shower, barn and greenhouse.

Listed by Dale Savage of Mary Stevens Realty

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$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* 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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22 Riveredge Drive Winchester CT 06098

MLS Number 170532030

  • Condo
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 992

This spacious condo offers privacy and light-filled rooms in a quiet community close to town amenities. There are two bedrooms and a full bath on the second floor. An open living area has access to a private terrace. This unit is ideal for single living, couples, or a family. All offers are subject to probate. All buyers must be prequalified prior to viewing.

Listed by Thomas McGowan of Elyse Harney Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* 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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29 Crescent Street Winchester CT 06098
Pending Continue to Show

MLS Number 170536504

  • Single Family
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 1,386
  • Acreage 0.23

Nicely maintained and updated in-town Colonial with easy walk to downtown shopping and schools. This 4 bedroom 1.5 bath home offers room for everyone with some energy efficient features that include, natural gas heating (with potential to add A/C), thermo-pane windows, blown in insulation along with other recent updates. The first floor features a large living room, compact kitchen, dining room, large multi-purpose room that includes the laundry, 1/2 bath and a mudroom. Upstairs you will find 4 bedrooms (2 with access to rear porch) and a full bath. The owner has shaped the rear yard into a nice usable space.

Listed by David Sartirana and Amy Sartirana of Northwest CT Realty

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$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* 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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11 Cherry Street Winchester CT 06098
Pending Continue to Show

MLS Number 170536204

  • Single Family
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,324
  • Acreage 0.37

Looking for a 3 bedroom, 1 1/2 bath Ranch home near Highland Lake with an attached 2 car garage, two porches - one at the front and an enclosed one off the garage in the back - a fire-placed living room, large dining room, AND A BRAND NEW ROOF (11/2022)??!! Well here it is! Enter through the front door into the living room with built-ins, hardwood flooring and a fireplace to help reduce that heating bill. Just off the living room is a large bedroom with hardwood flooring and ample storage that could also be a den or an office. Straight back you will find the large dining room with hardwood flooring and a beautiful view of the back yard. The kitchen with tiled flooring is just to the right. A newer refrigerator and dishwasher (both within a year) are in place and there are plenty of cabinets for the space. Down the hall you fill find a full bath with an easy access shower, a modest size bedroom with an adjoining 1/2 bath and another large bedroom with storage. Back in the kitchen you have easy access to the garage so no need to trudge groceries through bad weather. The basement entry is in the garage. You will find more storage shelves in the basement. Outside there is plenty of room for gardening in the sunny yard whether it be vegetables, flowers or both. Book a showing today!!

Listed by Amy Sartirana and David Sartirana of Northwest CT Realty

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$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* 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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114 Moore Avenue Winchester CT 06098

Winchester, CT114 Moore Avenue

Price$234,900

Est. Mortgage: $/month

MLS Number 170535721

  • Single Family
  • Bedrooms 7
  • Bathroom 2
  • Square Feet 2,580
  • Acreage 1.61

The 1914 Farmhouse sits on 1.6 acres with its own pond and barn. The possibilities are endless. No doubt it needs work! But it will be well worth the effort and time. Restoring this to its original state could be the challenge you have been waiting for. Possibly a bed and breakfast? Wanting to raise chickens? Have old cars needing storage? Barn for hobbys. Large family needing space? Possible accessory apartment? Wanting to raise your own vegetables? The list goes on. Close to town for shopping, restaurants and community college. Easy access to highway. Close to Health care. Home will be sold "As Is" to settle Estate.

Listed by Joanne M Donne of The Washington Agency

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$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* 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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341 North Main Street Winchester CT 06098

Winchester, CT341 North Main Street

Price$219,000

Est. Mortgage: $/month

MLS Number 170535926

  • Single Family
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 1,972
  • Acreage 0.32

Need space? This is clean, well-maintained, federal brick home with stone foundation that has an over the garage apartment with oak strip floors offering potential to be a private home office, studio, guest suite, man cave or improved for rental income. The attached garage has an indoor entrance to the mud/laundry room directly off the kitchen. Hardwood floors are throughout the house with an expanded walk in closet in the main bedroom. An infrared space heater in the living room, directly fed by city gas, is an alternative source of heat with the turn of a knob. A hardwired generator hook up is easily connected to your generator for power outages. The walkup attic has a thermostat-controlled fan that draws air up from open windows to cool the whole home and a large amount of storage space. The fenced-in back yard has a small garden and room to build a gazebo. Through the back entrance of the garage, a picnic area can be created in the fenced-in side of the house. The home is connected to both public water and public sewer. Improvements include a whole house water filter on the main water line, reverse osmosis filter at the kitchen sink, Buderus furnace, newer electric hot water heater (less than two years old), bathroom plumbing, toilet, sink and fixtures. This IS the solid, well-built home, with the private extra space you are looking for!

Listed by Marcus Santore of Marrin Santore Realty LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* 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 Elm Street Winchester CT 06098

Winchester, CT45 Elm Street

Price$525,000

Est. Mortgage: $/month

MLS Number 170535181

  • Multi Family Multi-Family For Sale
  • Square Feet 8,382
  • Acreage 0.17

Bring your ideas to this extremely well-maintained 7 unit brick building! Property consists of 5 residential apartments and 2 office spaces. Either keep as-is, and rent out as offices or convert each office to a 2-3 bedroom apartment. Over $80,000 spent in renovations in the last 10 years! Some notable improvements include: full remodel of all commercial office space, all new common hallways, and many updated apartments. The entire building has been converted to natural gas, with both boiler and water heater less than 3 years old. Owner pays for heat/water/sewer (expenses attached). Each tenant gets a designated parking spot; there is plenty of additional off-street parking with a paved lot in rear of building. Replacement windows done in 08. Offices available for the first time in over 20 years. With many long-term renters, this building grosses $54,000 a year with some below market rents. Offering easy access to routes 8 and 44, shopping, Northwestern Community College, dining and recreation, this space is easy to rent. Don't miss this incredible opportunity with a proven money-maker in a fantastic location; schedule your showing today

Listed by Michael P Doherty of KW Legacy Partners

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$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* 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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229 West Wakefield Boulevard Winchester CT 06098

MLS Number 170533607

  • Single Family
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 2,305
  • Acreage 0.39

Waterfront Property!! This spectacular 4 bedroom, 2 bath waterfront home is the luxury year-round lake house of your dreams! Situated on the west side of Second Bay at Highland Lake, this home has unobstructed water views and features a flat, level waterfront lot with over 70 ft of shorefront. Easy access to the water with sandy beach entry. Located in Winchester, Litchfield County CT you can spend your days enjoying all the activities this boating lake has to offer. Meticulously and fully renovated in 2016, this stunning home exemplifies great design. With hardwood floors, state of the art kitchen and bathrooms, a 1-year old roof, central air, fireplace, new windows and doors, all you need to do is move right in! The home's open concept floor plan and spacious living area make entertaining easy as you take in the unobstructed lake views. The eat-in kitchen boasts stainless steel appliances as well as beautiful quartz countertops. The gorgeous sunroom is another ideal spot to take in the beautiful vistas over Highland Lake. Upstairs there are 4 bedrooms and the sprawling primary bedroom is sure to be a serene lakeside retreat. First floor laundry, a generator, a security system, and auxiliary water pump ensure your only worry will be having fun and making memories to last a lifetime. Plenty of storage throughout. With all furnishings included, you can move into this stunning property immediately and have the beautiful clean water of Highland Lake right outside your door!

Listed by Kate D'addabbo of Coldwell Banker Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* 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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208 Coe Street Winchester CT 06098

Winchester, CT208 Coe Street

Price$750,000

Est. Mortgage: $/month

MLS Number 170533300

  • Single Family
  • Bedrooms 5
  • Bathroom 6
  • Square Feet 5,284
  • Acreage 1.5

Welcome to "THE OVERLOOK" Aptly named as it overlooks a gently sloping vast yard complete with fruit trees, tiki hut, garden shed, and the Indian Meadow Stream. An amazing view in all seasons. Imagine the possibilities of this well built, well cared for home. Over 5000 sq feet of living space. Two complete homes that flow from one to the other making single family or multi-generational living a breeze. Or close them off and you have a legal 2 family duplex. Imagine owning your own Bed & Breakfast? With 5 bedrooms, 6 bathrooms, 3 fireplaces, two kitchens, 2 dining rooms, 2 living rooms, and an assortment of extra rooms your dream home/business may become a reality. The primary bedroom suite consists of a large bedroom, a huge dressing room, fire place, office or sitting room, a palatial 2 bathroom combination with soaking tub in the center and a library. These duplexes converge onto the patio which is submersed in nature and is a hummingbird paradise in Spring and Summer. They've been coming since 1994! Other highlights include, 2 car garage, wrought iron entry gate, security system, full house generator, central air, exterior lighting and professional landscaping. You will be the entertainment envy of your friends and family! They may come and never leave! This home is a unique treasure of convenience and character. Only 2 owners in 80 years! Must be seen to truly appreciate. Take advantage of all that the Northwest Corner has to offer.

Listed by Sharon Chase of The Washington Agency

$
$
%
$/month over payments
Federal 30-year interest rate: 6.49% last updated on Dec 1, 2022
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

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