Winchester 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. 

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

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139 Grantville, Winchester, CT 06098

Price$3,295,000

Est. Mortgage: $/month

MLS Number 170104937

  • Land
  • Acreage 412.09

This Litchfield county estate comprising of 419+ acres offers innumerable possibilities for today's buyer. The 1830 Colonial-style residence needs renovation. Its features include built-ins, many large windows, fireplaces, and wide plank hardwood floors. The acreage has flat, moderate, and steep terrain with open meadows and wooded areas. There is 5615 feet of frontage on a town maintained, paved road and an additional 2000+ ft frontage on an abandoned town road. A large pond, access to the Mad River, stone walls, a swimming pond and a quarry are also on the property. This is a place where only the noise of nature will fill your senses.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 10, 2019
* 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 Grantville, Winchester, CT 06098

Price$3,295,000

Est. Mortgage: $/month

MLS Number 170105658

  • Single Family
  • Property Style Colonial
  • Bedrooms 6
  • Bathroom 5
  • Acreage 419.09

This Litchfield county estate comprising of 419+ acres offers innumerable possibilities for today's buyer. The 1830 Colonial-style residence needs renovation. Its features include built-ins, many large windows, fireplaces, and wide plank hardwood floors. The acreage has flat, moderate, and steep terrain with open meadows and wooded areas. There is 5615 feet of frontage on a town maintained, paved road and an additional 2000+ ft frontage on an abandoned town road. A large pond, access to the Mad River, stone walls, a swimming pond and a quarry are also on the property. This is a place where only the noise of nature will fill your senses. Owner says 4172 sq. ft.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 10, 2019
* 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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538 Wheelers, Winchester, CT 06098

MLS Number 170113448

  • Single Family
  • Property Style Tudor, Other
  • Bedrooms 5
  • Bathroom 3
  • Acreage 0.7

Highland Lake Waterfront with views up and down this wonderful clean boating lake. Complete with private landing and take off rights for your sea plane! This eclectic, charming home exudes warmth and style from the moment you enter the spacious sun room with its heated radiant floor and the living room with its wood trusses, stone fireplace and access to the terrace with pergola. The cook's kitchen is complete with a cook top with grill, two double ovens and a pretty tiled floor, farm sink, and center island. Leaded glass french doors open to a most comfortable dining room complete with window seat with lake views, dry bar and wainscoting. A separate breakfast room with skylights takes you back to the 1950's with its banquette seating done in upholstered vintage colors. Three bedrooms and bath are on this level and a nice master suite is located on the second level with loft, walk in closet and attic space. The lower level has a newly remodeled bedroom and bath with shower. A workshop, storage area and mechanical room are there as well. The outdoor areas are one of the best for entertaining with several terraces, a 28X30 two tiered wood deck and lawn areas taking in the wonderful views. Great dockage for your boat(s), walk-in swimming area and two sheds . Wheelers Point is a private lane with five other waterfront properties. This 444 acre lake is known for boating, fishing and its cleanliness. This is truly a remarkable property and home inside and out!

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 10, 2019
* 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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123 Ashley, Winchester, CT 06098

MLS Number 170083510

  • Single Family
  • Property Style Barn
  • Bedrooms 3
  • Bathroom 3
  • Acreage 3

Welcome to "Water Haven" - a truly serene private setting awaits you. Come watch the sunshine glisten on the water and take in the mesmerizing views from virtually every room. "Water Haven" sits on 3 acres with 250 ft. of water frontage on the shore of Connecticut's beautiful 82 acre Park Pond in the foothills of the Berkshires, offering four seasons of beautiful scenery and outdoor activities. Getting away from a busy life starts here with a true post and beam Yankee Barn home built in 2005 offering a casual and comfortable home of 2812 sq. ft. with two stone fireplaces. This three bedroom, 2.1 bath residence has an open floor plan with a large deck to enjoy the natural lake front setting with a beautiful stone bulkhead, a 20 ft. dock and floating dock as well as a sandy launch area for your kayak or canoe. Your guests will be happy to have their own private quarters with kitchen and bath. The lower level offers radiant heated floors and 10 ft. ceilings. This home also has solar panels to offset electric costs. This is a rare offering on a much sought after pond. Park Pond has residences scattered around the perimeter and offers four seasons of beautiful scenery and outdoor activities. It's a great place to kick back, relax and enjoy the beauty and tranquility of this special well cared for home on the pond. If you are a car buff or hobbyist you will certainly enjoy the heated garage space this home offers.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 10, 2019
* 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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129 East Lake, Winchester, CT 06098

Price$848,000

Est. Mortgage: $/month

MLS Number 170122413

  • Single Family
  • Property Style Colonial
  • Bedrooms 3
  • Bathroom 4
  • Acreage 0.6

Recently expanded and beautifully remodeled colonial with hardwood floors and high end finishes throughout; enjoying expansive views of the lake from all three levels of living space. The pictures/slide show only tells part of the story. This house was carefully designed with a focus on entertaining for family and friends with an open floor plan and abundance of light. A true feature of the house and statement piece are the two folding glass doors merging the lake and large deck with the living room. The finished basement room with half bath enables full use of the backyard, hot tub, and waterfront dock. The dock house offers a relaxing shelter right on one of the largest lake frontages. An additional feature is the boating inlet next to the dock house; making launching of kayaks, canoes, jet skis, and other small boats easy. Just minutes from town and shopping, the house is conveniently situated. Though originally built in 1910 the house went through extensive remodeling/renovation in 2016.

Listing Courtesy of Higgins Group

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$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 10, 2019
* 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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422 East Wakefield, Winchester, CT 06098

MLS Number 170103261

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 3
  • Acreage 0.48

Highland Lake in hot demand for its 444 acres of clean water , great fishing and boating. This charming home is a real home, not an old cottage with some updates . It is a 4-5 bedroom home with a 25 x 25 deck over looking the water. It has been renovated by its present owner with an addition , a new kitchen, garage, central air in most of the home , newer roof and composite dock. The living room has a stone fireplace, vaulted ceiling, skylights and built-ins. A family room off the sun filled kitchen has direct access onto the deck with steps leading to a waterfront deck area and newer dock. The kitchen is very adequate with nice cabinetry, tile backspash and breakfast area with water views. A dining room, mudroom with cedar closet, pantry area and new full bath completes the first floor which has hardwood and tile flooring, Two additional baths with 4-5 bedrooms are on the second floor along with a laundry room/office . Pretty plantings surround the property with a seasonal brook and newer detached two car garage with storage. Newer well, sewers and good parking are a plus. Minutes to Rt 8 and under an hour to Hartford and Bradley International Airport. Enjoy great summer venues in the area, farmer's markets, the Berkshires , hiking , kayaking and skiing in the winter. Winsted has some great eateries, terrific cinema with dining, and NW Community College. This is a must see house in a beautiful setting.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 10, 2019
* 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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167 West Wakefield, Winchester, CT 06098

MLS Number 170072831

  • Single Family
  • Property Style Contemporary
  • Bedrooms 3
  • Bathroom 2
  • Acreage 1.4

The panoramic view from the deck of this custom Lindell Cedar home allows views of First bay through the first narrows into Second Bay and into Third Bay. You will receive sunshine from sunrise till sundown. Set on over 200' of waterfront that allows for multiple docking positions. This home features two main level bedrooms along with an open kitchen, dining and main living area with cathedral ceilings and wall of windows with the same panoramic view as the deck The second floor contains the master suite with master bath and walk in as well as a loft area for den or office.The lower level offers approximately 600 square feet of expandable living space with walkout to the waterfront. Need space to park the toys, there is an oversized three bay heated garage with expandable second floor. Highland lake is a 444 acre lake and is noted for its clean water, one of the reasons is this property along with 95% of the properties on the lake are connected to city sewer. Just 45 minutes to Hartford and Bradley International Airport. The Berkshires are very close by as well as Infinity Music Hall and Warner Theater. 2 hrs. To NYC and 2/12 to Boston.

Listing Courtesy of Northwest CT Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 10, 2019
* 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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234 Perch Rock, Winchester, CT 06098

Price$679,000

Est. Mortgage: $/month

MLS Number 170098926

  • Single Family
  • Property Style Colonial
  • Bedrooms 3
  • Bathroom 2
  • Acreage 0.2

Highland Lake waterfront gem. One owner custom built three bedroom, two bath home carefully designed for easy maintenance, open floor plan and spacious entertaining areas. Built in 2002 the owner has used this lovely home as a second residence. Gleaming hardwood floors in the open living room/dining room and kitchen have lake views with access to a spacious covered and open deck. The kitchen has nice cabinetry and a mudroom -pantry area and full bath complete the first floor. Three bedrooms and large bath with whirlpool tub and separate shower are on the second floor. An unfinished walk out lower level consisting of approx. 960 ft is easy to finish off if needed with a flu for a pellet stove and ejection pump for a bathroom. The back yard is level with wide launch and walk access to the water. A beautiful dock is included. Town water and sewer are a plus, maintenance free siding, garage, central air, central vac and automatic generator are just a few of the nice features of this home. Approx. 75 ft. of waterfront. Priced to sell on a lovely side street with great views. Enjoy great fishing, boating, kayaking, paddleboarding at this sparkling clean 444 acres lake which is a hidden gem. Less than an hour to Bradley Airport and the Berkshires for wonderful year round venues. Skiing, hiking, great restaurants are very short distances.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 10, 2019
* 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, Winchester, CT 06098

Price$675,000

Est. Mortgage: $/month

MLS Number L10231012

  • Single Family
  • Property Style Colonial
  • Bedrooms 3
  • Bathroom 3
  • Acreage 0.2

Your new adventure starts right here... Move right in to this beautiful upscale all season home located on 3rd bay of Highland Lake. Everything rebuilt with all amenities brand new 2012. Open interior floor plan design with larger windows for the best natural light views of lake. Massive outdoor composite decks for entertaining. With sandy waterfront and a boating dock with exposure to western sunsets make this property a true gem. Take advantage of the year round lifestyle of lakeside living at its finest. Additional .08 acres included.

Listing Courtesy of Town & Country Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 10, 2019
* 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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210 West Wakefield, Winchester, CT 06098

MLS Number 170052256

  • Single Family
  • Property Style Colonial, Bungalow
  • Bedrooms 4
  • Bathroom 2
  • Acreage 0.12

"Takitezy" is the perfect name for this 2011 year round direct waterfront Colonial which, in our opinion, has the best panoramic views over Highland Lake. At water's edge the present owner carefully designed the floor plan to take advantage of water views from all rooms while using fine quality materials and mechanicals. This like new gem offers an open floor plan on the main level that includes a well equipped kitchen, dining area and living room with French doors to a 24 X 24 Trex deck where the views will sell this house - simply spectacular! There are four bedrooms and 1.5 baths and hardwood flooring. The master bedroom has its own private balcony. A new generator is in place to be connected by buyer, town water and sewer, propane heat and 200 amp electrical service. The grounds are designed with just the right amount of flowers and shrubs to give privacy while you are on the 8 ft. cantilever trex dock or enjoying the sitting area with benches and an outdoor fireplace. A boat lift is in place for permit purposes and a floating dock for sunbathing or cannonballs into this crystal clear 444 acre lake. Parking for 6-8 cars, 150 ft. of waterfront with great fishing and boating opportunities. Great amenities, seasonal venues, restaurants, easy access to Rt. 8 and the Berkshires are just a few of this area's amenities. Waterfront living just doesn't get any better than this and it all can be yours for $675,000 and is priced to sell!

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 10, 2019
* 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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376 East Wakefield, Winchester, CT 06098
Pending

MLS Number 170145565

  • Single Family
  • Property Style Cape Cod, Cottage
  • Bedrooms 4
  • Bathroom 2
  • Acreage 0.3

Chic direct year round waterfront renovated home on Highland lake noted for its clean water, fishing and boating. The waterfront at this recently renovated special residence is a must see as it has wonderful vistas, lawn, sunshine and dock at waters edge. A brick walk leads you into this contemporary cape style home. Unlike many other waterfront properties, many rooms including the master bedroom, family room, sunroom, office and living room have water views. Nothing to do but move in to this thoughtful renovation which includes two new bathrooms, one on each floor including one first floor bedroom. The kitchen has new granite counters, painted cabinets and new appliances opening to a good sized dining area and family room that has sliders to a great deck. The atrium sunroom with its new floor can be used for a treadmill, reading room, breakfast area or you decide with its great views. A brick fireplace, beams and original real wood paneling is so cozy on cool nights. All flooring on the main level rooms are original wood in newly refinished condition. The second level brings you to a nice loft area for a playroom, gaming area or sitting room and opens to an office or extra sleep area. Three additional bedrooms with new carpet on the second floor which includes the master which has great water views and a second floor newly remodeled full bath.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 10, 2019
* 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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309 Colebrook, Winchester, CT 06098

MLS Number 170122764

  • Land
  • Acreage 160

Offered is the perfect location for your mountain retreat, estate, horse farm, or nature sanctuary. Once a working cattle farm, the 160 mountain top acres are 90 % gently rolling, suitable for clearing and multiple uses. Still in place is the original 13 room home, barn, sheds, outbuildings and farm equipment from yesteryear! With old logging roads throughout and approx 20 acres of open fields, you need only add the horses. The abundance of wildlife, birds and butterfly's cannot be overstated on this nearly unspoiled land. The home with its old world charm, is hooked into a HUGE solar panel system that creates more energy than needed and actually credits the owners annually. The property borders state land and large pond to the south side. Per owner there are a number of mature black walnut trees through-out the property and the last time the wooded 140 acres was harvested was about 25 years ago. Bring offers

Listing Courtesy of Town & Country Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.45% last updated on Jan 10, 2019
* 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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Information contained in this Smart MLS listing has been compiled from various sources, all of which may not be completely accurate. Smart MLS makes no warranty or representation as to the accuracy of listing information. All information that influences a decision to purchase a listed property should be independently verified by the purchaser. Copyright 2017 Smart MLS, Inc. All rights reserved.