The Matthews GroupWilliam Raveis

The Matthews Group

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 Group 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
  • Property Style Colonial, Chateau
  • Bedrooms 5
  • Bathroom 4

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: 3.05% last updated on Oct 14, 2021
* 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: 3.05% last updated on Oct 14, 2021
* 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

MLS Number 170440461

  • Single Family
  • Square Feet 1,949
  • Year Built 1963
  • Bedrooms 3
  • Bathroom 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: 3.05% last updated on Oct 14, 2021
* 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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118 Newfield Road Winchester CT 06098

MLS Number 170372717

  • Single Family
  • Square Feet 3,075
  • Property Style Antique, Victorian
  • Bedrooms 5
  • Year Built 1903

Nestled on top of a gentle hillside with western views on over 8 acres just south of Winchester Center. Originally built as a summer home for the daughter of a prominent NYC/Boston businessman, this property was carefully crafted and well built in the boom of the Victorian period. This property has served as a working farm. Move right in and set up a farm for work or play. The house features 5 spacious bedrooms, 3 1/2 baths, living room and dining room with butlers pantry and two staircases. Original impeccable hardwood floors throughout. Freshly renovated kitchen with new appliances and cabinetry. Plenty of closet space, partially finished basement with wine room. Separate wing from previous caretaker quarters, and private attic wing with its own bathroom. 2 working fireplaces. Beyond the house comes a 7,000 sq ft peg barn with updated electrical, plenty of space for parties, storage, livestock or has the potential to be converted into a guest house. Additional 3 bay tractor barn that once belonged to the 1700's farmhouse that was on site until the mid century. 2 car garage with attic plus a single garage used for tools and equipment but can easily be a 3rd garage. Property has potential to store 10+ vehicles between the buildings. This is a gem just over 2 hours from NYC or Boston. Minutes to Litchfield, Goshen, Highland lake and Torrington areas. Agent Owner.

Listed by William Raveis Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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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711 West Wakefield Boulevard Winchester CT 06098

MLS Number 170368687

  • Single Family
  • Square Feet 2,660
  • Bedrooms 3
  • Bathroom 4
  • Year Built 2021

Our plan or yours Large lot for the lake, 50 feet on the water, Easy access from forest ave. Plenty room to park andd party!!

Listing Courtesy of Turning Point Realty,LLC

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$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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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804 East Wakefield Boulevard Winchester CT 06098

MLS Number 170424516

  • Single Family
  • Square Feet 2,492
  • Property Style Colonial
  • Year Built 1945
  • Bedrooms 3

Do you love watching magnificent sunsets over the lake? You can choose your haven at this beautiful lake front home! From the Brazilian hardwood stationary dock or three tiered patio with sun setter canopy and covered dining or inside by a cozy fire or maybe just relaxing on the balcony off the master bedroom. Set in a quiet cove on the east side of Highland Lake this 2400 sf colonial has so much to offer. The great room and dining room combo has huge windows to give you the most beautiful view of the lake, a lovely washed brick fireplace & gorgeous hardwood floors. The updated kitchen features Corian counters and Hickory cabinets. A bedroom and full bath finish the main floor. The second-floor offers two more bedrooms with new hardwood floors & cathedral ceilings. The breathtaking master bedroom has as much glass that the home designer allowed & a full length glass walled balcony. The guest bedroom can fit a whole crew of folks. For your entertaining pleasure the walk out basement offers a 25x16 tiled room with a refrigerator, sink, cabinetry and a 1/2 bath with laundry. Outside you'll find a hard covered dining area open to the 3 tiered patio with bluestone stairs right to the water. The stunning stationary dock has hardwired lights, under-dock lighting, a concrete pillar and pad, and is constructed with steel beams for years and years of enjoyment. All 4 seasons are beautiful on the lake, even winter, watching cross-country skiers glide across the lake.

Listing Courtesy of William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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: 3.05% last updated on Oct 14, 2021
* 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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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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39 South Main Street Winchester CT 06098

MLS Number 170365799

  • Multi Family Multi-Family For Sale
  • Square Feet 3,486
  • Bedrooms 7
  • Bathroom 4
  • Year Built 1900

Three properties totaling 4.41 acres for one price! 1. 3500 sq ft 2 family home featuring 1800's architecture including massive period correct windows, wrap around porch, beautiful stone foundation, and detached 2 car garage. 5 bed, 2 1/2 bath main house with 2 bed, 1 bath attic apartment. Brand new heating system installed this year! 1.13 acres 2. Freshly updated 960 sq ft ranch. 3 bed, 1 bath, walk out basement, great backyard with tons of potential. .37 acres. 3. 2.9 acres of undeveloped land. Potential for multiple access points. Condo's? Apartments? Parking garage? Bring your ideas and imagination. All properties sold together. Total tax $8102/year Assessments 2 family $150,710 1 family $82,530 Land $8,120

Listing Courtesy of The D'Amore Agency,LLC

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$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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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401 West Wakefield Boulevard Winchester CT 06098
Pending Continue to Show

MLS Number 170386449

  • Single Family
  • Square Feet 2,050
  • Bathroom 2
  • Year Built 1930
  • Bedrooms 3

Perched over the beginning of Third Bay, this home sits across the street from the water yet offers some spectacular all season views over Highland Lake while maintaining affordable taxes. Included in the sale is a waterfront parcel that contains 200' of direct waterfront with a modest size cabana used for storage in the winter and entertaining in the summer. The contemporary style home features 3 bedrooms and 2 full baths. Enter the home from the large wraparound deck overlooking the lake into the large family room that contains a nice dining area, breakfast bar and wood stove for cozy winter nights, there is lots of glass affording great lake views. French doors lead you into the remodeled kitchen and from there you can enter the living room with a fireplace and propane log set, another set of french doors lead you into a bedroom overlooking the lake. On the upper level there is a full bath and two modest size bedrooms. This home has much to offer and is great for entertaining from a very intimate to the largest of gatherings.

Listing Courtesy of Northwest CT Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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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870 West Wakefield Boulevard Winchester CT 06098
Pending Continue to Show

MLS Number 170429416

  • Single Family
  • Square Feet 1,682
  • Bedrooms 2
  • Bathroom 1
  • Year Built 1900

Come see....It's a perfect getaway! Highland Lake waterfront year round ranch cottage located at the east end of 3rd bay. Open floor plan for one level living or expand the lower unfinished level w/plumbing in for future bath. Lower level walk out basement leads to a beautiful stone patio and a sandy area to waters edge with concrete steps into the water. No lawn to mow here. You & your family will love playing in this sandy area. Close to Rt8, restaurants, breweries, shopping and all Litchfield County has to offer. 30 min drive to Bradley Airport and 2 1/2 hours to NYC

Listing Courtesy of Northwest CT Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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

MLS Number 170399855

  • Single Family
  • Square Feet 2,265
  • Year Built 1996
  • Bathroom 4
  • Property Style Colonial

This impressive colonial was designed in 1996 and sits at a higher elevation than most homes on Highland Lake. The property stands tall on a 1 acre lot and is generously sized with 4 bedrooms, 3.5 baths and an in-law apartment off of the kitchen. TONS of space and potential with the full basement and the 2 car garage. You can relax by fire pit in the backyard, the fireplace in the living room or move the jacuzzi on the back deck! Stunning views from the master bedroom's glass enclosed deck - a beautiful place to wake up in the morning. Walk down the hill, set your feet in the lake on your new dock and call Highland Lake “Home”. Agent/Owner related.

Listing Courtesy of Berkshire Hathaway NE Prop.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 2021
* 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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