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The Matthews Team

Winchester - Winsted 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 Team at 860-868-0511 with any questions or to schedule a private tour.

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711 West Wakefield Boulevard Winchester CT 06098

MLS Number 170498612

  • Single Family
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 3,000
  • Acreage 0.74

Largest lot available on lake . Room for parking , pool , partys See also mls 170498605

Listed by Peter C Kores of Turning Point Realty,LLC

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$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* 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 Road Winchester CT 06098

MLS Number 170207910

  • Land
  • Acreage 82
  • Zoning R-1

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. Taxes and assessment are for both parcels.

Listed by Stephen M Drezen and Karen Newton of William Pitt Sotheby's Int'l

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%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* 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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411 West Wakefield Boulevard Winchester CT 06098
Pending Continue to Show

MLS Number 170500270

  • Single Family
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 2,963
  • Acreage 0.73

Welcome to beautiful Highland Lake. This charming home has 2 parcels of land totaling .83 acre. The first piece (.73) of property has the beautifully maintained, year round 3 bedroom 2 bath home with a private backyard, and magnificent views of the lake from many areas. The second waterfront parcel (.10 acre) is 167' long, 2 docks, a boat launch, sea wall and a Klotter Farm shed. The main level features a warm, inviting iiving Rm with a stone fireplace, built-ins for storage and beautiful hardwood floors. The newer applianced, L-shaped Kitchen has it's own dining area, pantry and large window to view the private rear yard, or go relax on your beautiful stone patio. There is a main floor bedroom, an office with laundry facilities and a full bath to complete the main level. Upstairs is the 17x15 primary bedroom and the 3rd bedroom, both with hardwood floors and the second full bath. For added storage there is also a walk-in attic on this level. Back to the main level where there is a bonus 30 x 30 ' partially finished addition, originally planned as an in-law set-up. Here you can let your imagination go wild and finish this area, or alter it to suit your wants or needs. . The 28' Breezeway connects the main house to the addition area and the spacious 25 foot three season room plus the 35 foot deck.

Listed by Cathy Zuzick of RE/MAX RISE

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$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* 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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874 West Wakefield Boulevard Winchester CT 06098

MLS Number 170486677

  • Single Family
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 2,240
  • Acreage 0.09

Looking for your year round retreat? This builder/designer's immaculate home is set in a private cove waterside. A lifetime of memories will be made here. Newly built, this stunning mid century modern style home is located on the sunny side of prestigious Highland Lake. You will enjoy high end finishes and 360 degree views. 3 Floors each have their own oversized trex decks (almost 1000 sqft total). Fabulous open floor plan, European designed kitchen created for the most discerning buyer has:an expansive 13 foot, granite waterfall island w/ample seating; imported, chic tiles; ss appliances;& perfect cabinetry. This room opens into a sun filled living rm surrounded by windows and cozy F/P. Beautifully appointed bathrms. The primary bedrm is captivating. This home comfortably sleeps 10 which includes an adorable bunkie rm; additional sleeping possibilities on the 3rd flr. Relax in the media rm. Enjoy spectacular sunsets & your own private beach. You can sit back and unwind as this home is turnkey & requires zero maintenance. A perfect all season hideaway w/ private dock. Magical views and blue skies abound. Highland Lake is a fun, clean recreational lake! Summer, popular activities include swimming, boating, kayaking, paddleboarding, tubing & fishing.During the winter, CC skiing, ice fishing, skating & snowmobiling. Skiing close by as well. For more information on the lake, check out hlwa.org. Conveniently located 2.5 Hours to Boston/NYC, 45 Minutes to Hartford.

Listed by Lori Elkins Ferber of William Pitt Sotheby's Int'l

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%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* 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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535 East Wakefield Boulevard Winchester CT 06098

MLS Number 170500368

  • Single Family
  • Bedrooms 5
  • Bathroom 3
  • Square Feet 3,395
  • Acreage 0.19

A waterfront dock on Highland Lake for your boat, with plenty of space to enjoy swimming, sunning, floating and sunsets! With a water front storage building as a bonus. Across the street walk through the front door of this lovely 3395 square foot home into a foyer with an open staircase and stone floors. The foyer flows nicely into the large eat in kitchen with hardwood floors, granite counters and stainless steel appliances. The living room has beautiful views of Highland Lake and the western hills of Winchester. The living room also has a large fieldstone fireplace and hardwood floors. The 2nd staircase in the living rooms leads to 3 bedrooms and a full bathroom. The original house is connected to an addition that was added in 2006. A wide hallway is open to the open front foyer and has a large window for tons of natural light and lake views. This hall leads to the primary bedroom suite, which has a walk-in closet, a full bath with spa bathtub and a shower. The bedroom connects to a laundry room and an additional room that can be a 5th bedroom, office or den. As an additional bonus there is a room in the attic with lake views that would also make a great office or play space. This house has the flexibility for whatever your needs are. You can have the best of both worlds, private lake access and much lower taxes then having main house directly on the lake. There is a 3 car garage an additional outbuilding for storage. Additional interior photos on Sunday.

Listed by Liz Zakrzewski of Coldwell Banker Realty

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$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* 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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206 East Wakefield Boulevard Winchester CT 06098
Under Agreement

MLS Number 170493421

  • Single Family
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,248
  • Acreage 0.12

**Turn Key** Highland Lake Direct Waterfront! Spectacular easterly views and access to the beautiful clean waters of Highland Lake, a 444-acre boating lake, in the town of Winchester, Litchfield County CT. COMPLETELY REBUILT in 2014, this LOW MAINTENANCE beautiful lake home boasts 3 beds and 1.5 baths with an amazing EXPANSIVE DECK! Beautiful vinyl plank wood floors, bead board and moldings through out. Gorgeous kitchen with granite countertops, stainless steel appliances, hood and two built in ovens. OPEN FLOOR PLAN with wide open views across the lake. Heated with the latest technology in electric resistance glass panel heaters. and electric baseboards. A tankless hot water heater with never-ending hot water! 3 generous sized bedrooms with a luxurious shower in the full bath occupy the second floor. Primary bedroom looks east over the lake. Plenty of closet space and a full basement for all of your storage needs. Worry free living in this totally secure home built with a camera and alarm systems and keyless entry. Spacious wrap around no maintenance deck with glass railings to preserve the view. Entertainment made easy with outdoor sound system and exterior lighting. No maintenance powered dock with lights. Parking for at least 5-6 cars. This YEAR ROUND RETREAT comes TURN KEY with all interior and exterior furnishings including TVs and sound system, grills, fire pits, 2 kayaks and 1 paddle board. Conveniently located 2.5 Hours to Boston/NYC, 45 Minutes to Hartford.

Listed by Kate D'addabbo and Mela Veltri Case of Re/Max Right Choice

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$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* 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 Road Winchester CT 06098

MLS Number 170304263

  • Land
  • Acreage 131.5
  • Zoning RR and GB

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!

Listed by Jill Vantine of Locust Lane Realty LLC

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$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* 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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194 Losaw Road Winchester CT 06098

Winchester, CT194 Losaw Road

Price$675,000

Est. Mortgage: $/month

Under Agreement

MLS Number 170464980

  • Single Family
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 2,033
  • Acreage 27.13

Quality Built Log Home situated on 27.13 acres in Litchfield County! Surrounded by beauty & steps away from Beaver Pond add to the peaceful feeling. Quiet country rd - perfect for all your outdoor activities. Property equipped for horses w/riding trails in your own backyard or venture out onto the country dirt road to enjoy the scenery. The private horse amenities accommodate up to 4 horses, large paddock easily divided into 2 w/ 2 run-in sheds, storage for 200+ bales of hay & grain & tack - water & electricity within, NEW electric fence re-strung 2021. Perfect for your horse care needs and enjoyment! Watch your horses from the windows while working in your office - Absolutely a wonderful set-up! The warmth of this home is felt upon entrance into the front door - The combination Living/Dining rm comfortable for gathering in front of the wood stove w/vaulted ceilings. Stylish kitchen offers a spacious granite kitchen island - fabulous views from 2-story windows while preparing your meals for the day! Offering 4 bedrms, spacious closets (including 2 cedar), inviting loft area, separate laundry rm, 2 full baths and walk-out basement for more living space. Multiple zone heating, New water tank 2022, newer roof 2016, newer well pump 2019, recently stained to maintain the beauty of the exterior logs 2019. Come see all this property has to offer with its near-by show barn w/indoor arena, beautiful lakes, hiking areas, skiing areas, 15 min to Infinity Music Hall and more!

Listed by Lisa L Bredice of William Pitt Sotheby's Int'l

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$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* 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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715 West Wakefield Boulevard Winchester CT 06098

MLS Number 170480057

  • Single Family
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 2,318
  • Acreage 0.41

Welcome to 715 West Wakefield Blvd. located on Highland Lake! This property feels like a private getaway. It is tucked back from the road, overlooking the Third Bay, and offers breathtaking views of the water all year round! Enjoy summer sunsets on the lake spent with family and friends on the lovely wrap around Trex Deck, such a perfect location for this spacious 4 Seasons home. Property has been wonderfully maintained. Walk through the front door into an open concept livingroom/kitchen with Breakfast Bar. There are two bedrooms on the main level and two more upstairs. Two full bathrooms each include his and hers sinks and plenty of space! Set up your home office in the loft overlooking the living room! The heated finished basement has large sliding doors that open to outdoor patio area, -perfect game room or den! Also includes a laundry room/storage area. Two car attached garage with ample parking. This house is perfect for all types of gatherings big or small. Easy lakeside living featuring access to Marina with slips, local shops, restaurants, state parks, ski slopes, campgrounds and major highways. New Water Heater

Listed by Christina Ducas of CENTURY 21 AllPoints Realty

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$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* 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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144 Marshall Street Winchester CT 06098

Winchester, CT144 Marshall Street

Price$525,000

Est. Mortgage: $/month

Under Agreement

MLS Number 170469540

  • Single Family
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,744
  • Acreage 55

Amazing Country Escape -- One floor living in this well maintained 3 bedrm home situated on 55 acres of land!!! This Ranch style home offers a spacious family rm separated w/beautiful french doors to allow for a casual area & formal area both equipped w/ fireplaces -- hardwood floors throughout. Fireplace warmth fills the home during the cooler New England days. And during the spring, summer and fall enjoy all the backyard fun -- hiking, 4 wheeling, chilling in the gazebo with beverage of choice & dinner grilled in the great outdoors. For those who love a workshop -- here it is at its best -- Oversized detached 3 car garage w/loft area above. Possibly the upper portion of this oversized garage could be finished off for your Home Office needs -- that would be absolutely amazing space surrounded by nature & separate from your home which is situated down the hill! Another detached 2 car garage to keep your vehicles out of the elements. An adorable shed can be used for tools/equipment -- or could be a perfect small space for those with kids to use as their special "Play House". As you drive up the driveway you will see & feel the charm of this property -- your private escape to call home --- so many possibilties for this property! Just 43 min to Bradley Int'l Airport, 53 min to Hartford & just over 2 1/2 hrs to NYC -- and for those who enjoy live entertainment -- just minutes to the Torrington Warner Theater & Norfolk Infinity Music Hall.

Listed by Lisa L Bredice of William Pitt Sotheby's Int'l

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$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* 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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227 Torringford Street Winchester CT 06098

MLS Number 170470109

  • Single Family
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,240
  • Acreage 15.85

Woodsman dream home located on over 15 acres, rear lot, privacy at its best! Come enjoy this 4 Bedroom 2.5 bath home, spauling front covered porch, fireplace, outdoor wood boiler, wood stove in basement. Just up the road from the Greenwoods Country club and a short drive to route 8. Backs open space! Come see what this home has to offer!

Listed by John T Maier of Maier Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* 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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66 Munro Place Winchester CT 06098

MLS Number 170472423

  • Single Family
  • Bedrooms 5
  • Bathroom 3
  • Square Feet 3,890
  • Acreage 0.4

"THE GOVERNOR'S MANSION" circa 1896 Home of Governor Lorrin A. Cooke 1896-1899 is located in Winsted Connecticut in a historic neighborhood on .4 acres, just a half-mile to beautiful Highland Lake for swimming, boating, and fishing. Just blocks to dining and shopping. The grand house offers 3,890 sq. ft. living space, providing five bedrooms and two and one-half baths with 1,500 sq. ft. additional space on the third floor for expansion. The opulent entrance hall is filled with period detail and opens to formal rooms with a sweeping staircase to the second floor. Each room pulls you into the next and offers multiple living choices. The historical significance of the home is profound. There is a large carriage house, an inground pool, and beautifully appointed grounds. The home will require your personal refurbishing and is well worth the effort.

Listed by Thomas McGowan of Elyse Harney Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* 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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