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. 

Winchester Real Estate

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

Winchester, CT139 Grantville Road

Price$2,250,000

Est. Mortgage: $/month

MLS Number 170238009

  • Single Family
  • Property Style Colonial, Antique
  • Bedrooms 6
  • Bathroom 5
  • Acreage 433.9

This Classic Historic New England, Antique Colonial Farmhouse dating back to the late 1700's, is beautifully sited on 433.9+ acres in the foothills of the Berkshire Mountains. The home offers the original wide plank flooring, four fireplaces and plenty of original features throughout the house. The home is in need of renovations to be brought back to its original beauty. There is a natural spring-fed swimming pool with 21 acres of cleared land with the original stone walls and large pond on the property. This truly is an amazing property and the beauty of nature abounds in this magnificent setting. The opportunities are endless for this property. It could make an amazing Equestrian Facilty, Hunting Lodge, Glamping property, Camp for Fishing, Training, Hiking, Rehabiltation Facililty, Recreation Area, Corporate Campus, Country Inn and Resort, Bed and Breakfast, Wedding Venue, Destination Retreat and Spa, Development - Estate, Lots. This property is CERTIFIED ORGANIC, so it could be used for Farm-to-Table farming, Apple/Pear/Fruit Trees, herbs, vegetables, farming for grains, hops and/or barley for micro breweries, a farming industry that has become a giant, fast-growing investment opportunity. Don't miss out on this amazing property. MOTIVATED SELLER!

Listing Courtesy of Neumann Real Estate

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$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 2020
* 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 Winchester CT 06098

MLS Number 170207910

  • Land
  • Acreage 82

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. Re

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$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 2020
* 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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208 Coe Winchester CT 06098

MLS Number 170240956

  • Single Family
  • Property Style Colonial
  • Bedrooms 5
  • Bathroom 6
  • Acreage 1.5

"THE OVERLOOK" Walk through this gated unique, solid well built duplex Colonial with its own separate first floor in-law apartment. Two car attached garage. Included in this home are 5 bedrooms, 5 baths and 1 half-bath. Two kitchens, two living rooms, a formal living room, study, library, den, office and furnished full season sun-room. It features pocket doors, partial central air, wood floors, a garden window in the bright kitchen, chair-rail throughout, and a complete master suite with his & hers baths and a soaker tub, dressing room, walk-in closets, and gas fireplace. These spacious rooms allow for large gatherings and entertaining. Escape outside to the beautiful manicured lawn with fruit trees, shrubbery, and perennials. Entertain at the above ground pool and relax at the "tiki" bar. On the chilly nights sit by the fire pit, or relax on the beautiful stone terrace. Property also consists of the year round Indian Meadow stream. This home also features outside lighting, a full house generator, wired surveillance camera system, and a security system. Travel one hour to Tanglewood & the Southern Berkshires, or closer to Norfolk's Infinity Hall & Bistro. Two hours and your in NYC or Boston.

Listing Courtesy of Donna Molon Real Estate, LLC

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$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 2020
* 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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208 Coe Winchester CT 06098

MLS Number 170240955

  • Multi Family Multi-Family For Sale
  • Bedrooms 5
  • Bathroom 6
  • Acreage 1.5
  • Square Feet 5,284

"THE OVERLOOK" Walk through this gated unique, solid well built duplex Colonial with its own separate first floor in-law apartment. Two car attached garage. Included in this home are 5 bedrooms, 5 baths and 1 half-bath. Two kitchens, two living rooms, a formal living room, study, library, den, office and furnished full season sun-room. It features pocket doors, partial central air, wood floors, a garden window in the bright kitchen, chair-rail throughout, and a complete master suite with his & hers baths and a soaker tub, dressing room, walk-in closets, and gas fireplace. These spacious rooms allow for large gatherings and entertaining. Escape outside to the beautiful manicured lawn with fruit trees, shrubbery, and perennials. Entertain at the above ground pool and relax at the "tiki" bar. On the chilly nights sit by the fire pit, or relax on the beautiful stone terrace. This home also offers the year round Indian Meadow stream. This home also features outside lighting, a full house generator, wired surveillance camera system, and a security system. Travel one hour to Tanglewood & the Southern Berkshires, or closer to Norfolk's Infinity Hall & Bistro. Two hours and your in NYC or Boston.

Listing Courtesy of Donna Molon Real Estate, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 2020
* 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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406 East Wakefield Winchester CT 06098

MLS Number 170209084

  • Single Family
  • Property Style Contemporary
  • Bedrooms 4
  • Bathroom 3
  • Acreage 0.92

Welcome to Eagle Point, sited on a private location on Highland Lake noted for its clean water. Pretty places to gather guests start at the deck. The nearby stone patio offers an outdoor dining area. The lawn is lush and is the perfect place for a game of corn hole. Guests and family will want to wander down to the shoreline and sit back in the shaded lounge area and take in the magnificent views of the lake. Beautiful renovation of this year round 4 bedroom, 3 full bath waterfront home began in 2015 and is situated in the heart of the Litchfield Hills at the gateway to the Berkshires in one of the most scenic sections of Connecticut. As you enter the mudroom with white washed brick floor you will fall in love with this special year round home. The kitchen is spacious and will remain unfinished so the buyer(s) can finish to their liking. The kitchen is enhanced by one wall of beautiful stone and local wide board pine floors. A walk in pantry is a bonus to the chef of the family and there is also a breakfast/dining area off the kitchen. The living room with its large windows provides peaceful and panoramic views of the lake and the mountains. Step out on the pressure treated deck and hear the sounds of nature - you are sure to spot the eagle landing in the tree as well as blue heron gliding across the lake. The family room is located off the kitchen and has a cathedral ceiling, stunning two story stone fireplace with sliders to the patio and lake views.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 2020
* 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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28-44 South Main Winchester CT 06098

MLS Number 170215808

  • Single Family
  • Property Style Colonial
  • Bedrooms 18
  • Bathroom 8
  • Acreage 1.25

These 6 contiguous properties located on busy Rte.# 44 are being sold " AS IS " only as a package , not individually and are located in TG zone . Think of all the Potential development options . This zone is referred to as the Town Gateway , and for good reason . Walking distance to Northwestern Ct. Community College , Restaurants , Park , Recreation facilities and future Medical Facility . Major intersection of Rte.8 & Rte.44

Listing Courtesy of The D'Amore Agency, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 2020
* 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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112 Newfield Winchester CT 06098

MLS Number 170246346

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 3
  • Acreage 45

When you envision a classic New England country home, set amid the rolling fields and wooded hills of Litchfield County, you have pictured this idyllic property. On 47 acres of meadows and woods, with a pond, stone walls, gardens, and split rail fences, this 1776 Colonial has been loved and improved through the years. The 2002 addition includes a versatile private guest suite that could easily serve as a master bedroom or office and a comfortable 3 season porch. The main house has been updated throughout while retaining many original features, including three fireplaces, one of them a massive cooking fireplace, wide board flooring, and beautiful wood paneling. The updated eat-in kitchen features soapstone counters, exposed beams, wood cabinets, and a large sitting area with French doors to a fieldstone patio. There is a modern boiler and radiant heat throughout the first floor. The vintage post and beam barn is in excellent condition. The village of Winchester is an undiscovered gem, and the location is convenient to recreation and dining in every direction. Come see for yourself!

Listing Courtesy of Elyse Harney Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 2020
* 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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543 West Wakefield Winchester CT 06098

MLS Number 170225059

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 3
  • Acreage 1

Meticulously maintained year round residence at sought after highland lake. 2 - story 4 bedroom, 3 bath home offers combination picturesque water view plus direct beach area water-frontage with dock & boat-lift. Awesome custom designed contemporary style master suite. 3 - zone hwbb oil heat, central air. Oversize 2 car garage. All roofing & vinyl siding is 8 years old. 10' x 10' rear deck includes underneath enclosed storage area. House is wired for generator. (generator does not remain) There are no disclosures for this property. At closing seller will give buyer the required credit of $500.00. "separate from this listed property, the owner has a waterfront lot (ctmls listing #170225067) @ 538 w. Wakefield boulevard, and a waterview lot (ctmls listing #170225075) @ 535 w. Wakefield boulevard each having full approvals with plans for the construction of a single family home." subject properties could make for a unique family compound. Owner would be open to a Package price sale for addresses 543, 538 and 535 w. Wakefield boulevard.

Listing Courtesy of Cohen Agency

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 2020
* 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

Winchester, CT51 East Lake Street

Price$775,000

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: 3.6% last updated on Jan 23, 2020
* 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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436 Winchester Winchester CT 06098

Winchester, CT436 Winchester Road

Price$695,000

Est. Mortgage: $/month

MLS Number 170182397

  • Single Family
  • Property Style Ranch
  • Bedrooms 3
  • Bathroom 3
  • Acreage 52.36

Southwestern style and ambiance with dramatic details throughout in this custom built, one owner home. Thoughtfully designed, carefully constructed, and beautifully maintained, all on 52 acres for privacy and recreation. A chef's ideal kitchen, stone fireplaces in both the Master Bedroom and Great Room (with a warming oven), vaulted ceilings and beams, a Sun Room overlooking the front gardens, a 3 season rear Porch, granite and marble counters in the Kitchen and baths, state of the art wood and oil heating systems - and that's just the beginning. Please see this one for yourself, it will not disappoint.

Listing Courtesy of Elyse Harney Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 2020
* 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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175 Main Winchester CT 06098

MLS Number 170265583

  • Multi Family Multi-Family For Sale
  • Property Style Other
  • Acreage 0.13
  • Square Feet 4,860

Gondek Group is pleased to present 175 & 183 Main Street in Winsted, CT. Please note this is a portfolio being sold with 183 Main Street. These 2 properties consist of 7 apartments and 2 Commercial Units. Beautiful Restaurant with patio overlooking the River and many improvements have been made to the apartments. New separate electrical, Newer roof, new on demand gas for Restaurant. Many Tenants have been long time renters. Great opportunity to buy a double digit cap rate building with additional upside. Medical facilities, CVS and Northwestern Connecticut Community College are close by. Become part of the growing Downtown! Winsted is also the home of Little Red Barn Brewery.

Listing Courtesy of Berkshire Hathaway NE Prop.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 2020
* 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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183 Main Winchester CT 06098

MLS Number 170265596

  • Multi Family Multi-Family For Sale
  • Property Style Other
  • Acreage 0.09
  • Square Feet 5,572

Gondek Group is pleased to present 175 & 183 Main Street in Winsted, CT. Please note this is a portfolio being sold with 175 Main Street. These 2 properties consist of 7 apartments and 2 Commercial Units. Beautiful Restaurant with patio overlooking the River and many improvements have been made to the apartments. New separate electrical, Newer roof, new on demand gas for Restaurant. Many Tenants have been long time renters. Great opportunity to buy a double digit cap rate building with additional upside. Medical facilities, CVS and Northwestern Connecticut Community College are close by. Become part of the growing Downtown! Winsted is also the home of Little Red Barn Brewery.

Listing Courtesy of Berkshire Hathaway NE Prop.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 2020
* 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.