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 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: 2.87% last updated on Sep 17, 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 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: 2.87% last updated on Sep 17, 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: 2.87% last updated on Sep 17, 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: 2.87% last updated on Sep 17, 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: 2.87% last updated on Sep 17, 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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630 East Wakefield Winchester CT 06098

MLS Number 170329359

  • Single Family
  • Property Style Colonial, Cottage
  • Bedrooms 3
  • Bathroom 2
  • Acreage 0.45

Enjoy Four Levels of living on Highland Lake's Pristine Third Bay. A Spectacular 100' Waterfront Property rarely available. This Property includes Two New Docks and a Boat Lift. This home is a MUST SEE for those looking for a true TURN KEY Lake Front home with character and plenty of room for family and guests. This thoughtfully renovated home features an Open Living and Dining Room Floor Plan and a Lower Level Bonus Room complete with a Beautiful Granite Top Wet Bar, Full Bath with Walk-in Shower complete with a Marble Top Vanity and it's own Deck. Living Room Features a Central Fireplace with Wood Stove Insert for those Chilly Nights and Energy Efficiency, 3 Bedrooms on the Second Floor with Newer Full Bath with Marble Top Vanity, Floor and Tub/Shower and Laundry Area. The Third Floor sleeps up to 8 additional people! Outstanding Sunset Views on the Main Level Covered Porch with plenty of room to Relax or Entertain. The Maintenance Friendly Exterior features NEWER Anderson Thermopane Windows and Doors, Vinyl Siding and Composite Deck flooring on both decks. Updated 200 amp Electrical, Blown In Insulation Throughout, Newer Concrete Foundation, Sea Wall and Newer Roof are just a few of the updated Improvements. Enjoy the fire pit in the beautiful outdoor garden area overlooking the Lake! Lots of Off Street Parking and Room for Garage. This home is move in ready for the Fall season!

Listing Courtesy of Re/Max Right Choice

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 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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536 Wheelers Winchester CT 06098

Winchester, CT536 Wheelers Point

Price$874,000

Est. Mortgage: $/month

MLS Number 170326407

  • Single Family
  • Property Style Cottage
  • Bedrooms 3
  • Bathroom 3
  • Acreage 0.37

Full of old world charm and located at one of the most sought after locations on Highland Lake this 3 bedroom, 2.1 bath lake house offers mesmerizing long views of the lake. The kitchen has been remodeled with new cabinetry, granite counters, a deep sink, stainless steel appliances and new flooring. The open living room/dining room boasts a stunning stone wood burning fireplace that will warm you while you sit back with a good book, a glass of wine or have great conversations with your guests. French doors lead the way to a family room/sun room with a full wet bar and skylights and a half bath. This wonderful room will wow your friends and family with its long lake views. There is also two bedrooms with a full bath located on the main floor. An additional bedroom is on the second floor with a full bath. There are several terraces for outdoor entertaining, grilling and lakeside laughter. Sit back in the lounge chairs on the lush lawn and watch the boats go by or enjoy a game of corn hole. At the approx. 100' waterfront is a sturdy 8' X 40' aluminum dock and a concrete sea wall and wide steps entering the lake. An automatic generator and central air wall unit is another plus to this great property on a private lane with just a few fine homes. The property has a variance in place to construct an addition that would create additional living space and a two car garage. Highland Lake is a 444 acre boating, fishing, swimming lake noted for its exceptionally clean water.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 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: 2.87% last updated on Sep 17, 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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878 West Wakefield Winchester CT 06098
Pending

MLS Number 170160974

  • Single Family
  • Property Style Split Level
  • Bedrooms 4
  • Bathroom 2
  • Acreage 0.35

Fantastic waterfront home. 4 bedrooms and a huge family room with wet bar and sliders that lead to a 14'x26' deck. There is another deck that is 14'x21'. Both decks feature retractable awnings. 16'x17' waterfront patio and gazebo. Don't worry about the parks being closed. Here you have swimming. fishing, boating, ice skating and snow shoeing and snow mobileing all in your front yard. Large LR with FP., formal dining room and a cozy breakfast room overlooking the lake. Large workshop in the lower level. Long dock gives you plenty of room for all your watercraft. Private location at the end of the Lake. This house features solar panels which provide you with affordable electricity. Come live your dream in this lovely waterfront home! All the attractions of Litchfield County and close to the Berkshires. A wonderful family home and a great place to raise a family.

Listing Courtesy of Mary Stevens Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 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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120 Ashley Winchester CT 06098
Pending

MLS Number 170219996

  • Single Family
  • Property Style Contemporary
  • Bedrooms 3
  • Bathroom 3
  • Acreage 10

LOOKING TO SOCIAL DISTANCE??? You have found it here at your private oasis on 10 acres possibly an additional 14 acres available to purchase to social distance from the world! Welcome to tranquil Winchester Center where time slows down to a peaceful pace & where you will find this true gem of a home nestled in the Litchfield Hills. Situated 300' from the road for privacy & seclusion! Travel up your 500' paved driveway to behold this gorgeous custom built 3 bedroom 2.1 bath Contemporary with attention to detail in the finishes throughout that include James Harde Plank siding, Arch. lifetime shingles, 2x6 Construction, structural laminate beams, footing drains, 1600sq ft stone patio overlooking the beautifully landscaped grounds & babbling brook, Marvin Integrity Low E Argon filled windows, over sized 3 car garage with 10' doors & 11' ceilings sure to accommodate your own collectibles/hobbies. 1000 gallon I/G propane tank, Central Air, Masonry wood heater with fireplace heated hearth, wood waiter elevator for ease of bringing your firewood to the Great Room fireplace. All trim & moldings throughout are custom milled wood, interior solid wood 6 panel doors. Cooks/Chefs delight with this gourmet kitchen with granite counters, custom cherry cabinets with 2 pull out spice drawers, pullout & soft closing drawers,4 lazy susans in corner cabinets & 2 appliance cabinets with plugs.GE Monogram appliances, 6 burner propane cook top, vented range hood with heat lamp & lighting.

Listing Courtesy of The Washington Agency

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 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.