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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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: 3.33% last updated on Apr 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: 3.33% last updated on Apr 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: 3.33% last updated on Apr 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. Re

$
$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 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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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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 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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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: 3.33% last updated on Apr 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

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: 3.33% last updated on Apr 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: 3.33% last updated on Apr 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 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: 3.33% last updated on Apr 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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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: 3.33% last updated on Apr 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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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: 3.33% last updated on Apr 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

MLS Number 170193987

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

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 CENTURY 21 Command Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 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.