The Matthews Team

William Raveis Lifestyles Realty

Winchester - Winsted CT Real Estate

Winchester, famously known as the Gateway to the Berkshire Mountains, is a town that promises an excellent quality of life with its stunning lakes and numerous recreational activities. Residents can indulge in popular pastimes such as swimming, fishing, boating, and water skiing.

The Winchester Business Park is home to several merchants and manufacturers, adding to the town's economic diversity.

If you're looking for a town that offers a perfect blend of natural beauty and business opportunities, browse our listings below to discover all available real estate and homes for sale in Winchester, CT.

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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52 Overlook Road Winchester CT 06098
Open House

MLS Number 170557057

  • Single Family
  • Next Open House: Sat 03/25 11:00 am. to 1:00 pm.
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 1,512

Come enjoy this spacious home with large eat in kitchen and living room. 2-3 bedrooms. Front porch facing Highland Lake perfect for relaxing. Home was just hooked up to city water! Extra large 20x40 foot garage with high ceilings. First floor laundry area. Open yard with plenty of room for gardening.

Listed by Sullivan Real Estate Inc

$
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$/month over payments
Federal 30-year interest rate: 6.6% last updated on Mar 16, 2023
* 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 Boyd Street Winchester CT 06098

Winchester, CT139 Boyd Street

Price$249,900

Est. Mortgage: $/month

MLS Number 170554262

  • Multi Family Multi-Family For Sale
  • Square Feet 2,104
  • Acreage 0.22

Very nice duplex style home features 2 units . Left side unit has 5 rooms 2 bedrooms and gas heat . Right side unit has 4 rooms 2 bedrooms and gas heat . The basement is insulated and most windows are vinly replacement . nice corner lot with paved parking . The roof is approx 10 years old,.The tenants pay there own utilities , There are 2 electric circuit breakers panels and 2 gas furnaces ,laundry hook ups . The house exterior was painted approx 2 years ago . The home has City water and city sewe and is close to Highland Lake beach and boar ramp . 1 days notice to show .no after 6pm showings . One or more owners is a licensed Real Estate agent in the state of Connecticut . Not the listing agent . Tenants are in the process of moving

Listed by Mary LeBlanc Realty

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$
%
$/month over payments
Federal 30-year interest rate: 6.6% last updated on Mar 16, 2023
* 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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Norwood Road Winchester CT 06098

Winchester, CTNorwood Road

Price$14,500

Est. Mortgage: $/month

MLS Number 170553198

  • Land
  • Acreage 0.06
  • Zoning HLD

Ideal location for storing your boat, rv or any other toys that take up garage space. 25x100 lot

Listed by Houlihan Lawrence WD

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$
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$/month over payments
Federal 30-year interest rate: 6.6% last updated on Mar 16, 2023
* 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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Norwood Road Winchester CT 06098

Winchester, CTNorwood Road

Price$8,990

Est. Mortgage: $/month

MLS Number 170552729

  • Land
  • Acreage 0.06
  • Zoning Residential

Ideal location for storing your boat, rv or any other toys that take up garage space. 25x100 lot

Listed by Houlihan Lawrence WD

$
$
%
$/month over payments
Federal 30-year interest rate: 6.6% last updated on Mar 16, 2023
* 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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522 West Wakefield Boulevard Winchester CT 06098

MLS Number 170551900

  • Single Family
  • Bedrooms 2
  • Bathroom 1
  • Square Feet 1,134
  • Acreage 1

LOCATION! LOCATION! LOCATION! Direct Waterfront Lake Property on a VERY RARE 1 ACRE level & private CORNER LOT with tons of parking on the highly sought after pristine, glistening & scenic Highland Lake in Winsted, Litchfield County, CT This property has approx 400 ft of waterfront w/a bonus pond area for small boat launch & is situated on the West side of 3rd Bay (close to Strong & Club Islands) of the 444 acre boating, paddle boarding, kayaking, swimming & abundant fishing Lake with a State owned & operated boat launch & is approx 45 mins from Bradley Airport & 2 hrs from NYC/Boston, minutes from Rt 8. The location of Highland Lake makes it a desirable destination being situated near the foothills of the Berkshires, approx 20 mins to Sundown Ski Resort, Platt Hill State Park Scenic Reserve, close proximity to the Town and all the fine dining, theater & shopping experiences you'll need. This home needs updating, it could be expanded upward, renovated or start from the footprint to build your own lakefront dream house. The house, property & all outbuildings are being sold "AS-IS". *Note: Current 2022 Assessment is $558,950. New Mill Rate will be decided in Late Spring - payments not due until July 2023 based on new mill rate*. Town Sewer & Private Well. For more information check out www.hlwa.org. Schedule your appt today!

Listed by Showcase Realty,Inc.

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$
%
$/month over payments
Federal 30-year interest rate: 6.6% last updated on Mar 16, 2023
* 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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66 Spencer Hill Road Winchester CT 06098

MLS Number 170551219

  • Land
  • Acreage 0.6
  • Zoning R-3

Tired of LOOKING for a home ????? Here is a Rare Opportunity to Build a New Home rather than settling for choices in Existing Home inventory . Surveyed .6 Acre Building lot with City sewer and water available at the Street . In established subdivision and Conveniently located close to services and highways. We can provide Builder

Listed by The D'Amore Agency,LLC

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$
%
$/month over payments
Federal 30-year interest rate: 6.6% last updated on Mar 16, 2023
* 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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18-4A Taylor Brook Road Winchester CT 06098

MLS Number 170551066

  • Single Family
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,135
  • Acreage 3.46

Beautiful custom built gem situated on a private site with a stream! Bright, sunny open floor plan with 3 bedrooms, 2.5 baths, great bonus room. Gleaming hardwood floors thru-out, granite tops, stone/marble baths, walk up attic. Large deck off kitchen. Don't miss this incredible opportunity!

Listed by The Washington Agency

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$
%
$/month over payments
Federal 30-year interest rate: 6.6% last updated on Mar 16, 2023
* 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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68 Mountain Avenue Winchester CT 06098

Winchester, CT68 Mountain Avenue

Price$199,900

Est. Mortgage: $/month

Active With Contract

MLS Number 170551070

  • Single Family
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 2,007
  • Acreage 0.23

If a spacious, well-loved and cared for home is what you are looking for then this is it! With four bedrooms, two full bathrooms, just over 2000 square feet and plenty of storage space you won't want to miss out on your chance to call this home. There is no shortage of parking and a covered porch off the kitchen for all your entertaining needs. Close to schools, restaurants, shopping and Route 8. Update this home with your own personal style or move right in! Schedule your tour today!

Listed by Tier 1 Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 6.6% last updated on Mar 16, 2023
* 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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145 Old New Hartford Road Winchester CT 06098
Active With Contract

MLS Number 170550589

  • Single Family
  • Bedrooms 2
  • Bathroom 1
  • Square Feet 1,154
  • Acreage 0.26

Welcome home to this adorable Colonial now available in Winchester! This home has over 1150+ Sqft of space and features 2 bedrooms and 1 full bathroom! Priced to sell, bring your eye for design, and see how you can turn this home into your Dream home! Private tours are available ASAP, schedule your tour today!

Listed by Executive Real Estate Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.6% last updated on Mar 16, 2023
* 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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44 Spencer Street Winchester CT 06098

MLS Number 170549265

  • Single Family
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 2,008
  • Acreage 0.41

This 3 bedroom 1.5 bathroom Victorian home with over 2000 sq ft of living is ready for its new owners. Many recent updates, and this home still has gorgeous original features. On the first floor you will find the kitchen, living room, dining room, den, and a half bath. The spacious 3 bedrooms and a full bathroom are located on the upper level. The primary bedroom has its own private balcony. Lovely crown molding throughout the house. Original built ins in the dining room and den.The backyard patio overlooks a stream. As per owner recent updates include New stainless steel appliances, new paint, all new radiators on first floor, new flooring first floor, butcher block counters, new cupboards/cabinets, newer roof (less then 3 years old), some new replacement windows on first floor, new wall tile in the second floor bathroom shower new faucets in the full bathroom, skylights in kitchen, recessed lighting, gas boiler, high efficiency tankless water heater, Radon mitigation system in basement, new stainless steal double sink and faucet in kitchen. conveniently located close to area amenities. Don't miss out! Schedule a showing today. Seller prefers a closing date on or after April 7th,

Listed by William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.6% last updated on Mar 16, 2023
* 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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59 Chestnut Street Winchester CT 06098
Pending Continue to Show

MLS Number 170549179

  • Multi Family Multi-Family For Sale
  • Square Feet 2,016
  • Acreage 0.28

3-Family home close to downtown. Plenty of off street parking. Needs some TLC but certainly worth the investment. 1st Fl (basement) apartment has a front porch, kitchen, living room, 2 bedrooms and a full bath. 2nd Fl apartment has a front porch, kitchen, living room, 3 bedrooms and a full bath. 3rd Fl apartment has a small back porch & a front porch, kitchen, living room, 2 bedrooms and a full bath. Each unit has their own laundry hook ups. There is access to the walk-up attic from the 3rd Fl apartment. May be subject to probate court approval. 24 hours notice due to tenants in place.

Listed by Northwest CT Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.6% last updated on Mar 16, 2023
* 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 Spencer Hill Road Winchester CT 06098

Winchester, CT146 Spencer Hill Road

Price$544,900

Est. Mortgage: $/month

MLS Number 170547725

  • Single Family
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 3,204
  • Acreage 2.2

Built to Last! Nicely updated Colonial with in law potential and mountainviews. This property features 5 beds, 4 baths, over 3200 square feet of living space, an eat-in kitchen with new cabinets and countertops, updated bathrooms, fresh paint, new flooring, a living room with stone fireplace, a 2 car garage plus 1 car attached carport, and over 2 acres of privacy. This property was built in 2001 and feels more like new construction with these recent updates. Schedule your showing today!

Listed by Century 21 AllPoints Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.6% last updated on Mar 16, 2023
* 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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The data relating to real estate for sale on this website appears in part through the SmartMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SmartMLS through a licensing agreement. Listing information is from various brokers who participate in the SmartMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2023 SmartMLS, Inc.