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

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426 East Wakefield Winchester CT 06098

MLS Number 170354356

  • Single Family
  • Property Style Contemporary
  • Bedrooms 3
  • Bathroom 3
  • Acreage 1.04

This custom-built year-round home offers one of the best locations on glistening Highland Lake. Enjoy over 130' of direct deepwater frontage & a southwest aspect that ensures stunning sunset views from the comfort & privacy of your very own deck. There is an impressive 2,000sqft of living space inc 3 bdrms, 2.2 baths. HW floors flow thru out the main living zone, dining area & into the EIK kitch where the home chef will discover plenty of storage w/in the custom cabinets & a suite of SS high quality appliances. The sumptuous owner's suite is positioned on the 1st flr w/ direct acc out to the deck + an ensuite w/ a steam shwr & a jet tub. The laundry is also housed on this level. If you need more room, there is an add 1,250sqft walkout LL w/ tall ceilings just waiting for you to transform into any space you need. This spectacular home is set back from the street on a level 1.04-acre zoning-compliant lot. There have been a host of updates to ensure a move-in-ready abode from the updated air-conditioner (2017) to the updated furnace (2015) & the architectural roof that was installed in 2000 & has been cleaned & treated regularly. The long list of extra features continues w/ a security system should you want to use this home as a holiday hideaway, + cedar siding, an attached oversized garage, a connection to city sewer & a well, + a natural granite waterfront that eliminates the need for wall maintenance. There is hydro-air heating & a gas fireplace for your year-round comfort.

Listing Courtesy of Berkshire Hathaway NE Prop.

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$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 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'l

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$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 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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119 West Wakefield Winchester CT 06098

MLS Number 170330282

  • Multi Family Multi-Family For Sale
  • Bedrooms 5
  • Bathroom 2
  • Acreage 0.64
  • Square Feet 1,781

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: 2.72% last updated on Nov 25, 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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123 Ashley Winchester CT 06098

MLS Number 170344075

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

It's been given the name "Water Haven". Come enjoy the Captivating views and live the lake life on Connecticut's 82 acre Park Pond. Once in a lifetime opportunity to own an absolutely stunning Yankee Barn home. Built in 2005 and set on three private acres with gorgeous water views, this three bedroom, two and one-half bath custom post and beam home has 2812 square feet of living space with two spectacular stone fireplaces, spacious bedrooms, beautiful hardwood floors and walk in closets. Soaring ceilings along with stunning water views from virtually every room add to the tranquility, beauty and serenity of lake life living. Come enjoy its understated elegance with its open floor plan and large deck offering captivating views, all of which make this an extremely inviting area for entertainment. The lower level has ten foot ceilings with cozy and comfortable private living quarters, kitchen area and a fireplace along with radiant floor heat. The home boasts an understated Garage lovers garage, offering radiant floor heat, an installed 11,000 lb. capacity vehicle lift and a large bonus room above that offers potential additional living space. An additional and separate lower level area also has radiant heat and an oversized garage door for additional vehicles or related equipment such as tractors/loaders/backhoes. Environmentally sensitive, solar panels are professionally installed to offset the costs of electricity.

Listing Courtesy of Coldwell Banker Realty

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$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 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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760 Lake Winchester CT 06098

Winchester, CT760 Lake Drive

Price$739,900

Est. Mortgage: $/month

MLS Number 170328177

  • Single Family
  • Bedrooms 3
  • Bathroom 3
  • Acreage 0.12
  • Square Feet 1,764

**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!!

Listing Courtesy of Northwest CT Realty

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$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 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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Winsted-Norfolk Winchester CT 06098

MLS Number 170304263

  • Land
  • Acreage 131.5

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. There are so many possibilities for this land! The seller is including a 1969 D8H Caterpillar Doxer to help the new owner work on the land where desired. Please call to schedule a showing. Please also see MLS #170304367 in the town of Colebrook.

Listing Courtesy of Locust Lane Realty LLC

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$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 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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107 West Wakefield Winchester CT 06098

MLS Number 170357239

  • Single Family
  • Property Style Contemporary
  • Bedrooms 3
  • Bathroom 3
  • Acreage 0.23

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

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$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 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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268 Perch Rock Winchester CT 06098

MLS Number 170342916

  • Single Family
  • Property Style Bungalow
  • Bedrooms 2
  • Bathroom 1
  • Acreage 0.16

Welcome Home to Highland Lake! A great place to work and play. Whether you need a home office with an amazing view or just a place to rest and relax or both, this 4-season Lakefront property has it all. The private setting is off the main road with an ample yard, plenty of parking and an attached carport. This home includes central air, pellet stove, fireplace and a generator that is turnkey ready. On the lakeside, steps lead right into the water to cool off on a hot day and a dock where you can fish and moor your boat. The unfinished basement has potential for more living space. The sunset views are waiting for you! Co-Realtor is related to owner.

Listing Courtesy of Northwest CT Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 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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147 Newfield Winchester CT 06098

MLS Number 170334696

  • Single Family
  • Property Style Contemporary
  • Bedrooms 3
  • Bathroom 3
  • Acreage 10.89

Enjoy all of the benefits the Energy Star certified home has to offer. This architect designed Contemporary home is constructed of extremely energy efficient structural panels and sits on nearly 11 acres at the top of the hill and offers plenty of privacy and distant westerly views that provide great sunsets and from the moment you pull into the driveway you can tell that this home and property are nothing short of well thought out. The main living level consists of an open concept kitchen and living room area, formal dining room with magnificent built ins, master suite with full bath, mudroom and laundry room with half bath. The upper level contain a full bath and two modest bedrooms. The home faces South providing passive solar benefits. There are currently 3 paddocks with run ins or the horses and passways leading to several acres of fenced in pasture. Lots of wild blueberries and mountain Laurel adorn the property as well.

Listing Courtesy of Northwest CT Realty

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$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 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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107 Spencer Hill Winchester CT 06098

Winchester, CT107 Spencer Hill Road

Price$525,000

Est. Mortgage: $/month

MLS Number 170271395

  • Single Family
  • Property Style Ranch
  • Bedrooms 3
  • Bathroom 3
  • Acreage 16.29

Your holidays will be perfect in this stunning home that sits high on a ridge, overlooking Highland Lake offering phenomenal sunrise and sunset views. This gorgeously updated Ranch sits on 16.29 sub-dividable acres where you can relax out on your front patio and enjoy the breathtaking seasonal views during warm weather months. Not to worry, you will enjoy the same wondrous views from inside your glass fronted living room during the colder months. This extraordinary home is a true private oasis; perfect for anyone who desires a retreat from the modern world. Known as Firefly Farm, this delightful one level home overlooks a charming meadow filled with over 500 pounds of wildflowers; a vision of loveliness all summer long! From your welcoming entry to the dynamic sunken living room boasting a sophisticated stone fireplace and gorgeous wood beamed ceiling, this gem of a home is sure to impress! The master suite is a splendid haven with a completely remodeled en-suite bath featuring stunning black bamboo floors and an incredible soaking tub that is sure to please. His and her walk in closets and cozy wall to wall carpeting complete your remarkable master suite. Set up your work-from-home space in the den or one of the additional bedrooms. A whole house generator will keep you toasty! Delightfully unique, this home affords you plenty of space and is perfect home for entertaining both inside and out. This is a once in a lifetime opportunity to own a slice of heaven on earth!

Listing Courtesy of Keller Williams Realty

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$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 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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601 East Wakefield Winchester CT 06098

MLS Number 170355823

  • Single Family
  • Property Style Ranch, Bungalow
  • Bedrooms 3
  • Bathroom 3
  • Acreage 0.46

Highland Lake-This house has 3 bedrooms-3 full baths-a 24x24 family room with gas log fireplace. Remodeled kitchen with new SS appliances & quartz countertops. Master Bedroom with slider to covered deck overlooking lake. Lower level rec room or possible in-law with full bath, gas fireplace and its own private patio. Upper level covered porch with awesome views of the lake. Rear deck overlooking private back yard. Own private lake front with dock. Two car attached garage plus a single detached garage. Short trip to Winsted or Torrington for shopping. 40 minutes to Bradley Airport and under two hours to NYC.

Listing Courtesy of Northwest CT Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 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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152 Ashley Winchester CT 06098

MLS Number 170340693

  • Single Family
  • Property Style Cape Cod
  • Bedrooms 4
  • Bathroom 4
  • Acreage 12.49

Wowsers!!! Large expanded Cape on over 12 secluded acres in the heart of Winchester Center with 3 Master Bedrooms Suites all containing full baths, hardwood floors and walk in closets. 1st floor master has pass-thru gas fireplace from bathroom suite to bedroom. Each bathroom has his and hers sinks. 2 extra bedrooms being used as a library with built in book shelves and a 1st floor office with another 4th bathroom or guest bathroom. Large open floor plan with hardwood floors thru out. Formal dining with wainscoting and open Living room with a flue for your Wood stove. Large back deck on ground level for cozy evenings to warm yourself by the fire pit. 3 storage sheds could be used a dog house, chicken coop or extra storage for gardening equipment. The oversized 2 car attached garages are heated. Large open basement ready to be finished for extra space or to be used with your imagination; art studio, gaming area, etc... Large wrap around porch overlooking private front yard. House can not be seen or heard from the road. The entryway mud room and 1st floor laundry room offers convenient location from garage to kitchen. This home comes complete with Central Air and Central Vacuum.

Listing Courtesy of Hunter Real Estate, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 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 TourAsk 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.