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

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Nov 14, 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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210-212 West Wakefield Winchester CT 06098

MLS Number 170177145

  • Single Family
  • Property Style Other
  • Bedrooms 11
  • Bathroom 9
  • Acreage 1.17

This is an exclusive opportunity to own a true compound estate on highland lake. This 1 of a kind location inc 3 homes. The 7000+ sqft main residence has 5+ bdrms, 4.1 bths & 7+ car garage w/ boat storage. The expansive 1st flr plan features mb suite, open & beautiful remodeled eik w/granite & ss appliances, xlg open dr, warm cozy lr w/fp, a sun porch & a family room. All rooms have expansive views of the water. There is also a deck system that stretches across the entire front of the home overlooking the lake. The 2nd flr houses all the rest of the bdrms & a huge bonus area that is currently being used as a music room. The 3rd flr level is a true recreational space for people of all ages that can be used as added sleeping space & is completed w/ a full bth. The walkout lower level is heated plumbed, wired & waiting to be finished for an amazing waterfront entertaining area which could include an infinity pool looking out to the lake. The 2nd home is direct water front & delivers a big bang in a small package. It comes w/ 2 levels of living space & 2 levels of deck space, a boat lift, a swim dock & multiple areas to enter the water. The 3rd home can sleep 8-10 people in beds in 4 separate bedroom areas. It also has a full kitchen, lr & 1.5 bths. The outdoor entertaining area has multiple levels of decks, a boat lift & 2 docks. Together the homes have over 250'+ of waterfront & the panoramic views of the lake are 2nd to none ** for more info see mls 170177143 & 170177142**

Listing Courtesy of Berkshire Hathaway NE Prop.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Nov 14, 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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856 West Wakefield Winchester CT 06098

MLS Number 170252061

  • Single Family
  • Property Style Other
  • Bedrooms 4
  • Bathroom 5
  • Acreage 0.96

This fabulous Hinkle designed Adirondack home, brings to light high-quality features and expression that mirrors the best in country living. With its spectacular waterfront including three docks, to the outstanding sunset views, this home is a must see for those looking for an adventure on the water. This home features an open country kitchen with high-end stainless-steel appliances, plus a Wolf multi burner gas range, w/ a double oven. Main level native stone fireplace creates a story telling environment enjoyed by all that gather in the great room. The home features hand cut cedar wood staircase, the walls are barn wood from New York State, hard pine floors from Alabama. Eagle windows, now owned by Anderson, Rocky Mountain door hardwood barnboard panels throughout, Buderus oil heating system, whole house generator (Guardian Model), Antique wood wainscoting panels, mahogany veranda deck, Ensuite Master bedroom, twin walk in closets, massive stone and woodburning FP w/ mantle & hearth, random hard pine floors, private w/ long lake views, open stone multi head shower, jetted tub, heated floor & more. Private office off wing of master suite. Each of the additional bedroom features a different themed ceiling The homes lower level includes a stained floor, a BR, half bath with sauna, summer kitchen,exercise/game & video room, & walks out to the patio complete w/ a stone fire pit over looking the lake. Take time to visit this one a kind property, you won't be disappointed.

Listing Courtesy of William Pitt Sotheby's Int. Re

$
$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Nov 14, 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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211/212 West Wakefield Winchester CT 06098

MLS Number 170177142

  • Single Family
  • Property Style Colonial, Other
  • Bedrooms 5
  • Bathroom 6
  • Acreage 1.05

Exclusive opportunity to own an estate on highland lake. This amazing location inc 2 homes. The 7000+ sqft main home has 5+ bdrms, 4.1 bths, 7+ car garage w/boat storage area. The expansive 1st flr plan features mb suite, open & beautiful remodeled eik w/granite counters, cherry cabinets & ss appliances, xlg open dr, warm & cozy lr w/fp, a sun porch & a family room. All rooms have amazing views of the water. There is also a deck system that stretches across the entire front of the house overlooking the lake. The 2nd floor houses the rest of the bedrooms & a huge bonus area currently being used as a music room. The 3rd floor level is a true recreational space fit for people of all ages that adds additional sleeping space & is completed w/ another full bath & laundry. The walkout lower level is heated, plumbed, wired & waiting to be finished for an amazing water side entertainment area which could inc an infinity pool looking out over the lake. The 2nd house is directly on the water & delivers a big bang for a small package. It comes w/2 levels of living space & 2 levels of deck space, a boat lift, a swim dock & multiple areas to enter the water. The panoramic view from every spot are 2nd to none. This awesome combo of homes can be purchased with mls# 17077143 for a discounted total price. This would make a true compound (see mls # 170177145). With all 3 homes you would have housing ability of 11 bdrms, 9 baths, parking for 20+ cars & over 250' of direct waterfront access.

Listing Courtesy of Berkshire Hathaway NE Prop.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Nov 14, 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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614 East Wakefield Winchester CT 06098

MLS Number 170246296

  • 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: 3.75% last updated on Nov 14, 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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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: 3.75% last updated on Nov 14, 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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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: 3.75% last updated on Nov 14, 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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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: 3.75% last updated on Nov 14, 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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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: 3.75% last updated on Nov 14, 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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28 South Main Winchester CT 06098

MLS Number 170215824

  • Commercial
  • Acreage 1.25
  • Square Feet 8,457

These 6 contiguos properties located on busy Ete.# 44 are being sold as a package , not individually and are located in TG zone

Listing Courtesy of The D'Amore Agency, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Nov 14, 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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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: 3.75% last updated on Nov 14, 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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262 Perch Rock Winchester CT 06098

Winchester, CT262 Perch Rock Trail

Price$820,000

Est. Mortgage: $/month

Pending

MLS Number 170193205

  • Single Family
  • Bedrooms 7
  • Bathroom 5
  • Acreage 0.24
  • Square Feet 4,416

Amazing sunsets await you in this year round 6-7 br, 4.1 ba. waterfront home located on a quiet side street with little traffic on beautiful Highland Lake. The home's front foyer flows to a glass-walled living room with stunning views of the lake. The living room also features an attractive stone fireplace, built-ins and gleaming cherry floors. You will enjoy cooking and entertaining in the spacious kitchen which offers double ovens, a dacor 6 burner gas cook top, center island breakfast bar and cherry cabinets. The dining room is open to the kitchen and has hardwood floors. The first floor bedroom or office offers water views and a large closet. A laundry room and powder room complete the first floor. There is nothing better than waking up to lake views in the master bedroom which has its own private balcony, a walk in closet, a full bath w/ double sinks, a whirlpool tub for soaking and taking in the views and a walk in shower. Two other bedrooms share a jack & jill bath. The lower level of this home features a family room with a wood burning fireplace, a full bar for entertaining all your lake guests, a guest bedroom with water views, a walk in closet and a full bath. The family room opens onto a large paver patio perfect for grilling, dining, cocktails, hanging out with friends and family or sitting back with a good book. That's not all this home has to offer there is a also a private guest or in-law apartment with a living room with

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Nov 14, 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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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.