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$1,795,000

Est. Mortgage: $/month

MLS Number 170280294

  • Land
  • Acreage 433.9

Attention all developers! Stunning Property with 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. Located just 10 minutes from Yale in Norfolk and 45 minutes from Tanglewoods. Don't miss out on this amazing property. MOTIVATED SELLER! Also be sold as Residential Listing with home - See listing # 170238009

Listing Courtesy of Neumann Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 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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139 Grantville Winchester CT 06098

Winchester, CT139 Grantville Road

Price$1,795,000

Est. Mortgage: $/month

MLS Number 170238009

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

MOTIVATED SELLER. REDUCED $455,000. BRING ALL OFFERS! 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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 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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614 East Wakefield Winchester CT 06098

MLS Number 170265800

  • Single Family
  • Property Style Colonial
  • Bedrooms 6
  • Bathroom 3
  • Acreage 0.45

*Highland Lake Waterfront Compound* Spectacular views and access to the beautiful clean waters of Highland Lake, a 444-acre boating lake, in the town of Winchester, Litchfield County CT. The property was meticulously renovated in 2016 by Third & Bay Design. Every detail was thoughtfully executed, from the main house, the guest house, to the original boathouse (one of only 5 original boathouses on the lake). The open floor plan and spectacular wrap-around porch on the main house affords unobstructed breathtaking views of the lake. Enjoy new appliances from Big Chill in the state-of-the-art retro kitchen, new bathrooms, fieldstone gas fireplace, security system, and new mechanicals. The camp-style property layout enjoys a main house, guest cottage with a porch and spectacular lake views, basketball court, and a boathouse having its own spacious deck and dock. Situated on the desirable east side of Third Bay, the property enjoys sun all day and unforgettable sunsets. With 100' of lake frontage, there is plenty of room for private swimming and boat/recreational toy docking. Outdoor amenities include beautiful stone walls accompanied by professional landscaping, as well as a substantial level lawn and raised stone fire pit for entertaining. Indulge your guests inside or outside the boathouse, relax on the expansive porch overlooking the water, or hang out in the picture-perfect guest house. What an incredible opportunity to own your Dream Waterfront Luxury Lake Home!

Listing Courtesy of Re/Max Right Choice

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 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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512 West Wakefield Winchester CT 06098

MLS Number 170308678

  • Single Family
  • Property Style Victorian
  • Bedrooms 3
  • Bathroom 2
  • Acreage 0.86

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.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 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
Pending

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: 3.03% last updated on Jul 9, 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: 3.03% last updated on Jul 9, 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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 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 170308450

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 3
  • Acreage 1.02

Beautiful four bedroom year round home with spectacular views of pristine Highland Lake. The current owner rebuilt this property as his retirement home. It has 2x6 construction, high end windows, 3 sliding glass doors, ledger board already in place for huge wrap around deck if desired. Unique 26 x 16 master bedroom with vaulted ceilings, hardwood floors, en suite bath with double vanity, jacuzzi style tub, shower and walk in closet. There is an attached, oversized, heated two car garage. Included on the opposite side of the road is an approx. 90 x 20 waterfront sand patio area with steps leading into the water.

Listing Courtesy of Northwest CT Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 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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522 East Wakefield Winchester CT 06098
Pending

MLS Number 170303072

  • Single Family
  • Property Style Ranch
  • Bedrooms 4
  • Bathroom 2
  • Acreage 0.6

Waterfront 4 bedroom, 2 bath, oversized 2 car garage, 2 fireplaces, screened porch and huge waterside deck are just some of the wonderful features offered with this year round home. This home was originally two homes, now connected by a huge light filled great room with a beautiful fireplace, hardwood floors and cathedral ceiling. Many newer items in the last few years. The floor plan offers many options for remodeling or living and entertaining in the currant configuration. Come see all the wonderful this home offers! The sale of this home includes a second .12 acre parcel.

Listing Courtesy of Vision Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 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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714 West Wakefield Winchester CT 06098
Pending

MLS Number 170193987

  • Single Family
  • Property Style Cape Cod
  • Bedrooms 3
  • Bathroom 4
  • Acreage 0.17

PRICE REDUCED! Ready to escape the hustle and bustle of the city? Ever dream of lakefront living? This is your chance! Admire the views from this newly constructed, year-round home located on Highland Lake. The home has an open floor plan with three levels. The main level consists of an open concept kitchen and living room, a combination mud room and half bath, as well as a master bedroom with a walk in closet and bath overlooking the lake. The top floor has two bedrooms, both looking out over the lake, laundry, and a full bathroom. Lake life is made easier from this bottom floor family/rec room designed for easy access to the lake and made for entertaining with a wet bar, laundry, and full bathroom. The spectacular views from nearly every room will say it all! Come take a look for yourself today! Highland Lake is a 444-acre lake nestled in the Berkshire Mountains of Litchfield County near the city of Winsted, Connecticut. Known for its crystal-clear water as well as for its fishing, boating, swimming and water-skiing opportunities. Enjoy the many area venues in the Berkshires for all seasons with skiing and hiking nearby as well. Minutes to Rt 8, under an hour to Hartford or Bradley International Airport, two hours to NYC, and two and a half hours to Boston. Owner/Agent related.

Listing Courtesy of Connecticut Realty, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 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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711 west wakefield Winchester CT 06098

Winchester, CT711 west wakefield

Price$583,000

Est. Mortgage: $/month

MLS Number 170315802

  • Single Family
  • Property Style Farm House
  • Bedrooms 3
  • Bathroom 4
  • Acreage 0.71

50 feet of deepwater frontage, plenty room for; family, parking, pool, and parties.

Listing Courtesy of Sullivan Real Estate Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 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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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.