The Matthews TeamWilliam Raveis

The Matthews Team

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 Matthews Team at 860-868-0511 with any questions or to schedule a private tour.

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201 South Road Winchester CT 06098

Winchester, CT201 South Road

Price$2,900,000

Est. Mortgage: $/month

MLS Number 170416816

  • Single Family
  • Square Feet 4,609
  • Bedrooms 5
  • Property Style Colonial, Chateau
  • Year Built 1997

A totally nature lovers tranquil & serene hidden location. Not visible from access road. First time offered for sale is this personal residence of long time established connecticut commercial builder / contractor. Constructed in 1997, this 4,600 +/- square foot brick & stone chateau style colonial affords the ultimate in privacy on 60 beautiful acres. One-third mile paved & lighted driveway leads to this park-like setting. 10 spacious rooms, offers country kitchen, 5 bedrooms, 3.5 baths, formal living & dining rooms, 3 fireplaces. Multiple open and covered decks / porches. In-ground heated salt water pool. Attractive landscaped grounds, large open 15 - 20 acre fenced-in field. Outbuildings include garage with 2-stall horse barn plus hayloft, fenced-in small stone building, storage shed. Expansion potential here as equestrian or other agricultural uses. Potential subdivision. Country location, yet close by for general retail shopping, medical services. Short distance to lakes, state parks, ski areas.

Listing Courtesy of Cohen Agency

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$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 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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132 Spencer Hill Road Winchester CT 06098

MLS Number 170207910

  • Land
  • MLS Status Active
  • Acreage 82
  • Other Amenities Golf, Waterfront
  • Subdividable

Very special land parcel. Western views overlooking Highland Lake. Pastures, fields, stone walls, brook & wooded areas showcase this wonderful building site. Ideal single family or subdivision potential. Land is actual several parcels on both Spencer Hill Rd and Spencer St totaling 81 +/- acres, Sewer & water nearby, but not yet permitted. Taxes and assessment are for both parcels.

Listing Courtesy of William Pitt Sotheby's Int'l

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$
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$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 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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652 East Wakefield Boulevard Winchester CT 06098
Pending Continue to Show

MLS Number 170440461

  • Single Family
  • Square Feet 2,879
  • Year Built 1963
  • Bathroom 3
  • Bedrooms 3

THE WAIT IS OVER*** THE EAST SIDE LAKE HOUSE EVERYONE HAS BEEN WAITING FOR***This home has been enjoyed and cared for by the same family since 1972. You are sure to enjoy all of the entertaining areas this home has to offer with family and guests. The living room has wonderful lake views and boasts a beautiful stone wood burning fireplace and faux beams. A side door leads the way to a large deck to soak up the sun, sit back and read a book, dine and enjoy the beautiful scenery on and around the lake. The master bedroom is located on the main floor and offers a nicely sized master bath. The kitchen is light filled with a breakfast nook. The dining room has adequate room for enjoying the holidays with family and friends. The second floor consists of two guest rooms and a full bath. The lower level offers a cozy family room with wood stove and awesome views of the lake and is open to a kitchen which makes it easy to cook and entertain guests on the covered lower level deck. There is a lower level guest room and room for the grandkids to bunk. There is also a full bath. The large lower level deck has a built in grill - you won't miss socializing w/ family and friends. Three car detached garage for your boat and cars with a loft above. A huge plus and of the best additions to this home is that you have your own boat launch area. Wow! The paved driveway goes all the way to the lake. What is important when purchasing a lake home you ask? - Parking, Garages, Waterfrontage, Location,

Listing Courtesy of William Pitt Sotheby's Int'l

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$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 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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760 Lake Drive Winchester CT 06098

Winchester, CT760 Lake Drive

Price$735,000

Est. Mortgage: $/month

MLS Number 170414426

  • Single Family
  • Square Feet 838
  • Bedrooms 3
  • Bathroom 3
  • Year Built 1910

**Exciting direct waterfront property! This is your escape to paradise! Highland Lake is approx.2 hrs. from NYC or Boston, minutes to Rt 8 and close to all the restaurants, wine trails and breweries Litchfield County has to offer. This exquisite home was entirely rebuilt in 2012! Enjoy lots of beautiful sunsets, sun filled rooms, 3 fireplaces and all the accoutrements of lakeside living. This home has it all! Three bedrooms, 3 bathrooms, and a great room with beautiful vaulted ceilings and many windows, allowing natural light to fill your home. The beautiful view from your trex decks and dock will inspire you! Beautiful open living and kitchen area with all the appliances and work space any chef would want. Lovely master bedroom with gas fireplace vaulted ceiling, hardwood floors and walk in closet. This is a home or hideaway for every season! Pay for your own vacation home with weekly rentals at $3000 or nightly at $400 as current owner has been doing!! Town hall square footage does not include finished upper story.

Listing Courtesy of Northwest CT Realty

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%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 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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203 West Wakefield Boulevard Winchester CT 06098
Pending Continue to Show

MLS Number 170457609

  • Single Family
  • Square Feet 2,470
  • Year Built 1907
  • Bathroom 3
  • Property Style Cape Cod

Breathtaking Sunrises & Bright Eastern Exposure in this 4 bed/3 full bath Year Round LAKE HOME. Loads of space to Entertain & Enjoy UNOBSTRUCTED VIEWS. 2 Living rms, 2 First floor full baths, Wood stove & Marvin French Doors that open to an Expansive 2 LEVEL DECK. Rear access off Von's Lane. First Floor Primary Bed ensuite with Huge walk-in closet! Full bath off Primary enjoys a walk-in tiled shower. Second 1st floor bedroom (can be a home office too), Wet/coffee bar & Main level laundry are just a few of the Amenities in this Lovely Home. The Eat in Kitchen has plenty of room to Relax & Soak In a long view of the lake! This Sunny Kitchen features an EXPANSIVE LAKE VIEW, Marvin French Doors, Living/Dining seating area, Stnlss Appliances, Wine fridge, Commercial faucet, a Chic barn door and a Gorgeous butcher block counter top! Enjoy your morning coffee on one of the two decks as you take in the scenery! Upstairs boasts 2 addt'l bedrooms w a full bath. Renovated to the studs in 2011! Improvements include a Newer Hot Water Heater, NEW FURNACE, Mini split system & Ample parking for all of your guests. This home is located in Second Bay on Highland Lake, a 444 acre boating lake located in picturesque Litchfield Cty. Included separate waterfront parcel with ENTERTAINMENT DECK & plenty of dock space for your boat! You will own one of the very few grandfathered lots at Highland Lake with an OVER THE WATER DECK! City water and Public sewer make this year round home an easy choice!

Listing Courtesy of Re/Max Right Choice

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$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 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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Winsted-Norfolk Road Winchester CT 06098

MLS Number 170304263

  • Land
  • MLS Status Active
  • Acreage 131.5
  • Other Amenities Waterfront
  • Zoning RR and GB

Absolutely beautiful land with a mixture of fields and forest. This listing is for a total of 5-6 parcels of land and is being sold together. Two of the lots are located in the town of Colebrook (Map 2 lot 33 with +-37.5 acres, about half of which is zoned General Business and Map 2 lot 34 on about half an acre, zoned General Business). The lots in Winsted are all zoned RR and are described as: Map 8, Block 155, Lot 1 with +-45 acres, Map 8, Block 155, Lot 18 with +-42 acres and finally Map 2 Block 152 Lot 41X (which is combined with lot 41AA) on +-6.5 acres. This property is also listed in the MLS in the town of Colebrook with the same information. All the land is currently being taxed as Forest Lane (490). Total taxes owed currently with the Forest Land designation are: $1,475.26, or would be $11,460.31 if not in Forest Land now (Colebrook's mill rate:30.90). There are many logging trails throughout the property, some of the highest elevation in Winsted, springs and brooks. This is beautiful property, please call to schedule a showing! Please also see MLS #170304367 in the town of Colebrook. There are so many possibilities for this land!

Listing Courtesy of Locust Lane Realty LLC

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$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 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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349 West Wakefield Boulevard Winchester CT 06098
Pending Continue to Show

MLS Number 170448204

  • Single Family
  • Square Feet 1,086
  • Property Style Bungalow
  • Bedrooms 1
  • Year Built 1923

Meticulously maintained vinyl sided year round lake house on beautiful Highland Lake with plenty of parking and a 13 X 30 detached garage built in 2018 with a loft above providing extra storage and possibilities. The living room is spacious and offers a stone fireplace for those chilly evenings, pine floors and sliders to a Trex deck with wonderful views of the lake. The kitchen has been updated with granite counters and stainless steel appliances. The master bedroom on the main floor has pine floors and a nice size closet. The full bath is delightful and has a frameless glass shower, tile and a granite sink. The lower level offers a large guest room/office with sliders to a beautiful stone terrace - a nice place to sit on a swing and take in the beauty of nature that surrounds. There is also a half bath with laundry. The driveway is paved and there is plenty of parking for all your lake guests. Behind the house you will find a private deck and patio for entertaining with family and friends. There is also additional paved parking across the street. Your own waterfront parcel is included in this sale and consists of 0.40 acres and approx. 50 feet of waterfront with great views, a worry free 40 X 8 PVC Evergrain Cement Board Dock, concrete seawall, privacy fence and ladder into the water. The boat lift is also included. Private well & Town sewer.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 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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121 West Wakefield Boulevard Winchester CT 06098
Pending Continue to Show

MLS Number 170457229

  • Single Family
  • Square Feet 2,265
  • Bedrooms 4
  • Bathroom 4
  • Year Built 1996

This Highland Lake Gem is a diamond in the rough. It has it all with 1 acre of privacy, awesome lake views, 50ft of direct waterfront that has a dock and a deck and there's plenty of parking. It was quality built in 1996 with I-Beam construction and features 9 room, 4 bedroom, 3 1/2 bathrooms, a huge basement with extra high ceilings. The extra space on the main level could be a 1st floor master suite or the separate entrance would make it perfect for an in-law/guest space to use for VRBO rentals. There is also a detached 2 car garage. The back of the home features a deck and a hot tub to enjoy all seasons watching all that nature has to offer. There is also a covered balcony off the master bedroom that over looks the lake where you can enjoy morning coffee or wine and cheese nights.

Listing Courtesy of Berkshire Hathaway NE Prop.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 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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113 Chapel Road Winchester CT 06098

Winchester, CT113 Chapel Road

Price$489,900

Est. Mortgage: $/month

MLS Number 170322315

  • Single Family
  • Square Feet 1,843
  • Bedrooms 4
  • Year Built 1974
  • Property Style Cape Cod

Very well maintained country home. Peace and quiet surround this hidden gem. Open floor plan including a fire placed living room that is open to the dining area. Large eat in kitchen, beautiful wood floors, family room. The garage is heated and would make a great place to enjoy your hobbies. To show is to sell. Several out buildings.

Listing Courtesy of Sullivan Real Estate Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 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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156 Ashley Road Winchester CT 06098

MLS Number 170411814

  • Land
  • MLS Status Active
  • Acreage 57
  • Other Amenities Waterfront
  • Zoning RU-3

Paradise found! Here in the Northwest corner! Come tour this beautiful 57 acre property of endless opportunities. There are 17 sprawling acres of cleared land. It has 2 barns, underground utilities and amazing well water. Another 40 acres of wooded land and apple orchards are waiting for you to customize and build your dream home. The land is very private, yet close to several lakes, ponds and hiking trails.

Listing Courtesy of Northwest CT Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 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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184 Torringford Street Winchester CT 06098
Pending Continue to Show

MLS Number 170413019

  • Single Family
  • Square Feet 2,602
  • Property Style Ranch
  • Bedrooms 3
  • Bathroom 2

This STATELY and ALL BRICK RANCH sits beautifully on approx. 14 acres overlooking a gorgeous pond and 'far as the eye can see' terrain. Conveniently located right off Route 8, this home offers easy access to all major businesses and amenities. From the easy flowing floor plan to the gleaming hardwood floors throughout the main floor, and beautiful bright kitchen with large island with granite countertops, who can ask for more. This home also boasts a spacious and welcoming living room, dining room right off the kitchen, 3 ample sized bedrooms on the main floor and deck off the sunporch. Perfect for barbecuing in the summer. With a kitchen, full bathroom, recreation room and plenty of bonus rooms in the basement, this home is ideal for an IN-LAW apartment complete with a separate back entrance/walk-out. Set up your appointment TODAY before it's too late!!!

Listing Courtesy of Berkshire Hathaway NE Prop.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 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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142 Main Street Winchester CT 06098

MLS Number 170368414

  • Multi Family Multi-Family For Sale
  • Square Feet 3,965
  • Year Built 1900
  • Bathroom 4
  • Bedrooms 6

Currently being used as a 4 unit multi family dwelling and is currently fully occupied. This property was once home to the famous Jessies restaurant. The home boasts much charm and character with charming center staircase, wood flors and lots of moldings. There have been many recent updates that include roof, windows and mechanicals. There is plenty of off street parking with a multi level parking area and two car detached garage along with a nice stone patio. This property has potential for many different uses such as professional offices, retail or even a restaurant. Lots of things happening in downtown Winsted, this could make a great investment.

Listing Courtesy of Northwest CT Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 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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