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. 

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139 Grantville Winchester CT 06098

Price$2,999,000

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: 4.28% last updated on Mar 21, 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$2,999,000

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: 4.28% last updated on Mar 21, 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: 4.28% last updated on Mar 21, 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: 4.28% last updated on Mar 21, 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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51 East Lake Winchester CT 06098

Price$795,000

Est. Mortgage: $/month

MLS Number 170157342

  • Single Family
  • Property Style Contemporary
  • Bedrooms 6
  • Bathroom 5
  • Acreage 0.7

This spacious and well maintained one owner year round Contemporary offers abundant room for a growing family or generational gatherings offering six bedrooms and 4.1 baths. The living room has hardwood floors with a floor to ceiling stone fireplace and a vaulted ceiling and flows into the dining room with access to a large wrap around composite deck perfect for sunning or a barbecue. The stairs down the center of the deck lead the way to a a beautiful lawn for the dog or the children to play and to hold family picnics. The kitchen is well equipped with two double ovens, a five burner cook top and has granite counters. There is a master bedroom en-suite on the main floor as well as a nicely sized half bath and full laundry room. The second floor has a loft area which overlooks the living and dining room and offers great views of the lake, a generous master bedroom en-suite as well as two other bedrooms and a full bath. A finished walkout lower level completes the home with three additional bedrooms, a full bath with whirlpool tub and a family/media room with sliders to a paver patio. The lawn is professionally landscaped and also has an irrigation system in place. There are two sheds located on the property and are a bonus to store all your watercraft needs or even an extra refrigerator at water's edge. A pure sandy beach walk in access is perfect for swimming or to launch your kayak or paddle board. There is also a composite dock for your boat as well as a water slide.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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 year round home has 4-5 bedrooms with 3 baths and a 25 x 25 deck with awning overlooking the water. It has been renovated by its present owner with an addition , newer 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 back splash and breakfast area with water views. A dining room, mudroom with cedar closet, pantry area and new full bath completes the first floor.Two additional baths with the 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. Two hours to NY. 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 and priced to sell.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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: 4.28% last updated on Mar 21, 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: 4.28% last updated on Mar 21, 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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878 West Wakefield Winchester CT 06098

MLS Number 170160974

  • Single Family
  • Property Style Split Level
  • Bedrooms 4
  • Bathroom 2
  • Acreage 0.35

Fantastic waterfront home. 4 bedrooms and a huge family room with wet bar and sliders that lead to a 14'x26' deck. There is another deck that is 14'x21'. Both decks feature retractable awnings. 16'x17' waterfront patio and gazebo. Large LR with FP., formal dining room and a cozy breakfast room overlooking the lake. Large workshop in the lower level. Long dock gives you plenty of room for all your watercraft. Private location at the end of the Lake. This house features solar panels which provide you with affordable electricity. Come live your dream in this lovely waterfront home!

Listing Courtesy of Mary Stevens Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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 170119988

  • Single Family
  • Property Style Antique, Farm House
  • Bedrooms 5
  • Bathroom 2
  • 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. So bring your offers and live nearly "off the grid" on the magical mountain-top paradise. Per owner sq ft under roof is approx 3,500.

Listing Courtesy of Town & Country Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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: 4.28% last updated on Mar 21, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

39 East Lake Winchester CT 06098

MLS Number 170042130

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 2
  • Acreage 0.69

Spacious, direct waterfront 8 room colonial featuring a 20x22 lower level family room with fireplace that opens onto a large private deck with hot tub. Home has tastefully updated kitchen and baths, hardwood floors and a master bedroom overlooking the lake. Beautifully landscaped yard with plenty of room for volley ball and outdoor activities. Enjoy sunsets and cocktails at the waters edge in the "crabshack" This island style cabana comes complete with a four seat bar that divides the interior sitting area from the covered outside porch. There is over 70 feet of waterfront with two permitted docks. This is the perfect setup for entertaining and enjoying the lake!

Listing Courtesy of Northwest CT Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

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.