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$1,195,000

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 170390640

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

PRICED TO SELL - 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: 2.94% last updated on May 13, 2021
* 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$1,195,000

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 170390642

  • Land
  • Acreage 433.9

PRICED TO SELL - 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 listed as a residential listing with home see listing #170390640.

Listing Courtesy of Neumann Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 2021
* 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 170374772

  • 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: 2.94% last updated on May 13, 2021
* 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: 2.94% last updated on May 13, 2021
* 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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118 Newfield Winchester CT 06098

MLS Number 170372717

  • Single Family
  • Property Style Antique, Victorian
  • Bedrooms 5
  • Bathroom 4
  • Acreage 8.12

Western views over protected land from this uber charming Victorian home just south of historic Winchester Center. 5 Bedrooms, 3.5 bathrooms, LR, DR, Library, Just renovated Kitchen, Butlers Pantry, Mudroom/Laundry, Office. Everything you need for todays living with the authentic charm of an antique house. Fabulous wrap around front porch rebuilt to very high standard. Gorgeous hardwood flooring. Incredible 7,000 sq ft peg barn - incredible potential as studio, guest space, pool house, etc. Multiple pool sites. 2 car and 1 car stand alone garages. 3 bay tractor barn. This is a gem just over 2 hours from NYC or Boston. Agent Owner.

Listed by William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 2021
* 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: 2.94% last updated on May 13, 2021
* 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

MLS Number 170368687

  • Single Family
  • Property Style Colonial
  • Bedrooms 3
  • Bathroom 4
  • Acreage 0.7

Our plan or yours Large lot for the lake, 50 feet on the water, Easy access from forest ave. Plenty room to park andd party!!

Listing Courtesy of Turning Point Realty, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 2021
* 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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62 Lakeview Winchester CT 06098

MLS Number 170394530

  • Single Family
  • Property Style Contemporary, Ranch
  • Bedrooms 5
  • Bathroom 4
  • Acreage 2.31

Whether you are looking for a weekend retreat or a place to call home year round, this fabulous Craftsman Colonial offers the perfect blend of tranquil country living and convenience. Architecturally designed addition over $800k in 2003. Beautiful handcrafted millwork featuring masterful stairways, cabinetry, paneled walls and furniture grade built-ins, sun washed interiors and oversized windows. Dramatic Great room with spectacular floor-to-ceiling stone fireplace is truly a show stopper. An Entertainer's DREAM! Formal dining room is perfect for fireside dinners and conversation. Enjoy the smart design of the well-equipped gourmet kitchen w/stainless appliances and Rainforest Green marble counters complimented by breakfast bar for two, dining area with banquette seating, and gorgeous custom built desk. Main floor includes three good sized bedrooms and master with white spa-like bath w/sliders that lead to private deck. Loft w/library overlooking great room and second floor guest suite complete the upper level. Finished lower level includes a cool home theater just perfect for movie night, an exercise room, full-bath and 23' x 16' versatile office/guest suite/family room with fireplace. Heated garage, quarter sawn white oak floors, new kitchen appliances 2019, new pool liner, new septic tank 2015. Majestic sunrises and sunsets, beautiful snowfalls, summer fun at the saltwater pool, gorgeous fall foliage. Your very own private oasis. Exceptional Experience. Exceptional Home.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 2021
* 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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401 West Wakefield Winchester CT 06098

MLS Number 170386449

  • Single Family
  • Property Style Contemporary
  • Bedrooms 3
  • Bathroom 2
  • Acreage 0.75

Perched over the beginning of Third Bay, this home sits across the street from the water yet offers some spectacular all season views over Highland Lake while maintaining affordable taxes. Included in the sale is a waterfront parcel with a modest size cabana used for storage in the winter and entertaining in the summer. The contemporary style home features 3 bedrooms and 2 full baths. Enter the home from the large wraparound deck overlooking the lake into the large family room that contains a nice dining area, breakfast bar and wood stove for cozy winter nights, the is lots of glass affording great lake views. French doors lead you into the remodeled kitchen and from there you can enter the living room with a fireplace and propane log set, another set of french doors lead you into a bedroom overlooking the lake. On the upper level there is a full bath and two modest size bedrooms. This home has much to offer and is great for entertaining from a very intimate to the largest of gatherings.

Listing Courtesy of Northwest CT Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 2021
* 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. This is beautiful property, please call to schedule a showing! Please also see MLS #170304367 in the town of Colebrook. There are so many possibilities for this land!

Listing Courtesy of Locust Lane Realty LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 2021
* 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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 2021
* 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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359 Winchester Winchester CT 06098

MLS Number 170397824

  • Single Family
  • Property Style Colonial
  • Bedrooms 3
  • Bathroom 3
  • Acreage 7.55

Hidden from behind this welcoming traditional Colonial home in hillside country are the most beautiful views imaginable. Come take a look for yourself and you won't want to leave! This pristine, sun-filled home with nearly 3000 sq. ft., has been lovingly cared for. Off the two-story foyer, open floor design features living room and dining room joined by a floor-to-ceiling fieldstone fireplace. Dining room with its spectacular views, can easily accommodate large crowds and opens to a knock-your-socks off screened-in porch, where you may relax, unwind and enjoy the calm, serene setting w/ distant views of Highland Lake. Luxury kitchen remodel by master craftsman with gorgeous white birch cabinetry, soapstone counters, stone subway backsplash, farmhouse sink, and Sub-zero fridge. An Entertainer's Dream Home! The view from the kitchen sink is a Don't Miss. Office off front foyer, mudroom, laundry and half bath complete main level. Upstairs find en suite master bedroom and 2 additional nice-sized bedrooms and full bath. The 27' x 21' family room, known as the “Skybox”, finished over the garage 2017 is accessed by a 2nd staircase off kitchen. The “Skybox” has separate heating/cooling system, surround sound and hook-ups for live music performances! The backyard is flanked by magnificent stone wall, emerald green meadows, 2 sheds, one of which is a 2 stall run-in shed w/ tack room. Breathtaking VIEWS! Perfect location. EZ commute to NYC and Boston.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 2021
* 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 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 2021 Smart MLS, Inc. All rights reserved.