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$3,400,000

Est. Mortgage: $/month

MLS Number 170416816

  • Single Family
  • Square Feet 4,609
  • Bedrooms 5
  • Bathroom 4
  • Year Built 1997

A totally nature lovers tranquil & serene hidden location. 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 fenced-in field. Outbuildings include garage with 2-stall horse barn and hayloft, fenced-in small stone building, storage shed. Expansion potential here as equestrian or other agricultural uses. 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: 2.78% last updated on Jul 22, 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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512 West Wakefield Boulevard Winchester CT 06098

MLS Number 170374772

  • Single Family
  • Square Feet 2,003
  • Bedrooms 3
  • Bathroom 2
  • Year Built 1910

One of the gems on highland lake is pine knoll. This breathtaking property is located on a peninsula having water all around it. It's features include a private island and two docks on the cove side for peaceful kayaking, swimming and ease of docking boats all while still having deeded access to deep water side for boating sports. It is a home that suits every season: enjoy long summer days and cool fall nights on the expansive wrap around deck and sweeping front porch. Winter will bring another element of enjoyment to the lake with snowmobiling, skating, ice fishing, snowshoeing and skiing is just a short drive away. Looking from every window is a view of the stunning water and wide professional landscaping making this the most beautiful location on the lake. This home includes plenty of private parking and a two car garage which is a rarity on the lake so no worries about entertaining and having lots of guests. The homes recent interior updates include a remodeled kitchen with granite counters and stainless appliances, a spa quality full bath and hardwood floors throughout the first floor. On the exterior there has been extensive mill work added around the windows. One look and you are home!! All you need to do is unpack your clothes because this is truly turnkey with all personal property and sporting equipment included. Hurry and you can be in to enjoy the whole summer season with your family. *additional bedrooms and a bath could be added in the walk up 3rd floor level*

Listing Courtesy of Berkshire Hathaway NE Prop.

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$
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$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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
  • Zoning R-1

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.

Listing Courtesy of William Pitt Sotheby's Int'l

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$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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
  • Bedrooms 5
  • Bathroom 4
  • Year Built 1903

Western views over protected land from this uber charming Victorian home just south of historic Winchester Center. 5 Bedrooms, 3.5 bathrooms, LR, DR, Library, Just renovated Kitchen, Butlers Pantry, Mudroom/Laundry, Office. Everything you need for todays living with the authentic charm of an antique house. Fabulous wrap around front porch rebuilt to very high standard. Gorgeous hardwood flooring. Incredible 7,000 sq ft peg barn - incredible potential as studio, guest space, pool house, etc. Multiple pool sites. 2 car and 1 car stand alone garages. 3 bay tractor barn. This is a gem just over 2 hours from NYC or Boston. Agent Owner.

Listed by William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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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119 West Wakefield Winchester CT 06098

MLS Number 170330282

  • Multi Family Multi-Family For Sale
  • Square Feet 1,781
  • Bedrooms 5
  • Bathroom 2
  • Year Built 1904

This home and property provide a unique opportunity to own a multi family at Highland Lake that has direct waterfront at a fraction of the taxes and the ability to have a large portion of your expenses covered by the potential income from the rental unit. The first floor unit has two bedrooms, large living room with sliders leading out to the veranda that overlooks first bay and a beautiful upscale kitchen that will make anyone that loves to spend time in the kitchen never want to leave. On the second floor there is a 3 bedroom unit that has been totally updated and will make a great rental unit for long or short term tenants, it too has a large porch overlooking first bay. Outside there is a large yard for recreation or just privacy. Large oversized two car garage and other storage building provide room for all the toys.

Listing Courtesy of Northwest CT Realty

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$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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: 2.78% last updated on Jul 22, 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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62 Lakeview Road Winchester CT 06098
Pending Continue to Show

MLS Number 170394530

  • Single Family
  • Square Feet 4,709
  • Bedrooms 5
  • Bathroom 4
  • Year Built 1958

Whether you are looking for a weekend retreat or a place to call home year round, this fabulous Craftsman Colonial offers the perfect blend of tranquil country living and convenience. Architecturally designed addition over $800k in 2003. Beautiful handcrafted millwork featuring masterful stairways, cabinetry, paneled walls and furniture grade built-ins, sun washed interiors and oversized windows. Dramatic Great room with spectacular floor-to-ceiling stone fireplace is truly a show stopper. An Entertainer's DREAM! Formal dining room is perfect for fireside dinners and conversation. Enjoy the smart design of the well-equipped gourmet kitchen w/stainless appliances and Rainforest Green marble counters complimented by breakfast bar for two, dining area with banquette seating, and gorgeous custom built desk. Main floor includes three good sized bedrooms and master with white spa-like bath w/sliders that lead to private deck. Loft w/library overlooking great room and second floor guest suite complete the upper level. Finished lower level includes a cool home theater just perfect for movie night, an exercise room, full-bath and 23' x 16' versatile office/guest suite/family room with fireplace. Heated garage, quarter sawn white oak floors, new kitchen appliances 2019, new pool liner, new septic tank 2015. Majestic sunrises and sunsets, beautiful snowfalls, summer fun at the saltwater pool, gorgeous fall foliage. Your very own private oasis. Exceptional Experience. Exceptional Home.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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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403 West Wakefield Boulevard Winchester CT 06098
Pending Continue to Show

MLS Number 170414688

  • Single Family
  • Square Feet 2,242
  • Bedrooms 3
  • Bathroom 2
  • Year Built 1981

Highland Lake Waterfront! Impeccably maintained, year-round waterfront home with multi-level floor plan features 120 feet of Waterfront and a Guest Cottage! The main home w/ 2,242 SF offers an open, bright L-shaped LR/DR with floor to ceiling Fireplace. Sunken Sunroom faces the backyard. Kitchen w/Breakfast Bar & plenty of cabinet space. Atriums to large, 28x16 Private Deck offers relaxing water views! Impressive Bath w/marble floors, marble counters w/ double sinks, sunken whirlpool tub, double shower enclosure & built in marble bench. Multi-level Master BR w/ vaulted ceiling, walk-in cedar closet, ductless A/C unit & Expansive windows for fabulous lake views. The fully finished, walk out lower level, with built-in entertainment center, cedar pantry, fully tiled Bath with Shower, offers more living space or gives guests their own privacy! 2 car Garage w/newer doors (2016), Pella windows (2015), Driveway (2016), HW Heater (2014), Furnace (2014), 200 AMP service & more! The Guest cottage w/ its knotty pine interior couldn't be more charming w/ 352 SF, a Half Bath, Kitchen & Sliders to the expansive deck that cantilevers over the water. The cottage offers New Roof (2018), Gorgeous, panoramic views, Dock, lawn space & New Fence (2019). Public Sewer. Fantastic lake location in 3rd Bay! Property also includes a total of 1.57 acres of land which borders land owned by the Winchester Land Trust. 402 West Wakefield is the address for cottage, 403 West Wakefield is the main house.

Listing Courtesy of Tier 1 Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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 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: 2.78% last updated on Jul 22, 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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107 West Wakefield Winchester CT 06098

MLS Number 170357239

  • Single Family
  • Square Feet 2,392
  • Bedrooms 3
  • Bathroom 3
  • Year Built 1989

Highland Lake - Waterfront with panoramic views. Enjoy the benefits of direct waterfront without the high taxes! Beautiful updated lake home with 2,392 square feet, 3 bedrooms and 3 full baths. This home features a stylish gourmet kitchen with granite counters, center island and stainless steel appliances, spacious dining room with pellet stove and a large lake facing living room with gas fireplace and dual sliders that open up to the front deck for breathtaking views! Don't miss the master bedroom with spa-like shower, sitting area, cathedral ceiling, sky lights, walk-in closet and sliders to deck. Other special features include: outdoor BBQ area with views, 2 car garage, ample off street parking, public water and sewer. One step into this home and you'll appreciate the attention to detail and the quality improvements; including the tankless hot water heater, roof, windows, central air, furnace, decks and so much more! Easy walk to the beach. One of the best locations to watch the sunrise! Highland Lake is one of CT's cleanest lakes and offers all-season activities. Easy 45 minute drive to Hartford, Bradley International Airport and 2.5 hours to NYC

Listing Courtesy of Northwest CT Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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

MLS Number 170386449

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

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: 2.78% last updated on Jul 22, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

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