The Matthews Team

William Raveis Lifestyles Realty

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 William Raveis Lifestyles Team at 860-868-0511 with any questions or to schedule a private tour.

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262 Perch Rock Trail Winchester CT 06098

MLS Number 170509862

  • Single Family
  • Bedrooms 6
  • Bathroom 5
  • Square Feet 4,416
  • Acreage 0.24

Your own oasis on the lake! Lovingly renovated waterfront home with western exposures on highly sought-after Highland Lake. As you walk into the grand foyer with cathedral ceilings and a newly built staircase, you are greeted by a living room with floor to ceiling tinted windows overlooking the lake. The main floor has a newly remodeled kitchen with Cambria quartz countertops, custom-built cabinets, high-end stainless-steel appliances, and an expansive island. The upper level boasts a brand-new primary suite, sitting area, with a separately designated walk-in closet and laundry. A brand new luxurious bathroom with custom-made Italian vanities, marble countertops and expansive shower with upgraded low iron frameless glass. Two of the three large upstairs bedrooms have water views! The lower level family room and bedroom walks out to a newly built stone covered sitting area with an outside television and bar for those rainy days and direct water front patio with a new dock and stairs to enter lake. City water/sewer with new high efficiency heating and cooling system and propane whole house generator! Make this place your summer home or live here all year round! Full list of renovations available upon request.

Listed by Jon Sheaffer of Sheaffer & Company Real Estate LLC

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$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 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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552 East Wakefield Boulevard Winchester CT 06098

MLS Number 170509036

  • Single Family
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 2,764
  • Acreage 0.28

Escape to paradise! The property is in the 3rd bay sunny eastside of Highland Lake. A 444-acre lake in Winchester, CT. Just a 30+ min drive to Bradley or appr 2 1/2 hours from NYC or Boston. Just 4 miles from Route 8. This is the lake house of your dreams. Magnificent lake views from every room in the house with a different sunset every night. Something for everyone. A large upper deck to enjoy the sun and a covered patio to enjoy the lake in the shade. Drive your car into the garage and it is just 2 steps into the great room which is open to the dining area and center isle kitchen. Upstairs you will find the master suite with full bath and walk in closes along with two modestly sized bedrooms and another full bath. The lower level features a family room with a fireplace (easily converted to a gas log set) a gorgeous full wet bar with a slider out to the covered patio and just a few steps to the lake. The dock is permanent (no in and out) and the sea wall is gunite (less maintenance). There is a utility shed to hold all your water toys/yard equipment and a small cottage is now used for storage but could be a future quest house. Plenty of off-street parking. The property has a boat lift and jet ski lift permit. Owner and agent related.

Listed by Frank C Carfiro of Northwest CT Realty

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$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 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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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 Emily Kores of Turning Point Realty,LLC

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$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 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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234 Perch Rock Trail Winchester CT 06098

Winchester, CT234 Perch Rock Trail

Price$999,900

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 170510827

  • Single Family
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 1,920
  • Acreage 0.2

Stunning! Highland lake direct waterfront beauty! Custom 3 bedroom 3 bath home with great open floor plan and amazing outdoor space and amenities. Main floor has hardwood floors, great open floor plan with combo living room/dining room all with beautiful lake views. Kitchen is right off the large deck which makes entertaining a breeze. Off the spacious garage is the mudroom, laundry and full bath. Three bedrooms on 2nd floor with large master with amazing windows overlooking the lake, a large bathroom with whirlpool tub and walk in shower. Large walk out lower level with updated full bath and the rest completely open space ready to be finished. The exterior space is simply incredible. Large deck with awning overlooks the lake and yard. Approximately 75' of direct waterfront with dock and decking with chairs and umbrella. Large flat grass yard, generator, plenty of room for boats, jet skis and all of your other toys! This home has it all with town water and sewer. A must see!

Listed by Steffen Reich of Coldwell Banker Realty

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$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 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: 5.22% last updated on Aug 11, 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: 5.22% last updated on Aug 11, 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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120 Ashley Road Winchester CT 06098

MLS Number 170507298

  • Single Family
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,556
  • Acreage 24

Welcome to your secluded oasis & personal nature sanctuary situated on a private 24 acre parcel! This gorgeous custom built 3 bedroom 2.5 bath contemporary home is nestled within the quaint & peaceful Winchester Center & the picturesque Litchfield County. This home is not visible from the road or neighbors. Only 2+/- hours to Boston/NYC, 1/2 hour to Great Barrington & the Berkshires. Attention to detail can be seen throughout with 2x6 construction, floor to ceiling fireplace with wood waiter elevator for ease of bringing firewood from the basement, oversized 3 car garage with 10' doors & 11' ceilings & attic storage. Primary bedroom is on the 2nd level & open to the great room below, with a propane fireplace insert, full bath with Jacuzzi bathtub & balcony. All trim/moldings throughout are custom milled wood, interior solid wood 6 panel doors, gourmet kitchen with granite counters, soft close cherry wood drawers, 6 burner propane cook top. East branch of the Naugatuck river cascading through the property that showcases small islands on the river, huge oak & black cherry trees are plentiful as are deer & other wildlife, gorgeous and pristine Winchester Lake & Park Pond within 1 mile +/- for kayaking, swimming etc, 10 mins +/- to Norfolk Historic District, Winchester/Winsted bustling main st & Rt 8. An abundance of restaurants, breweries, wineries & distilleries in the area as well for all to enjoy! Please DONOT drive up to the house without a confirmed appointment.

Listed by Diane L Carroll of The Washington Agency

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$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 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: 5.22% last updated on Aug 11, 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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268 Perch Rock Trail Winchester CT 06098
Pending Continue to Show

MLS Number 170511074

  • Single Family
  • Bedrooms 2
  • Bathroom 1
  • Square Feet 972
  • Acreage 0.16

Welcome Home to Highland Lake! A great place to work and play. Whether you need a home office with an amazing view or just a place to rest and relax or both, this 4-season Lakefront property has it all. The private setting is off the main road with an ample yard, plenty of parking and an attached carport. This home includes central air, pellet stove, fireplace and a generator that is turnkey ready. On the lakeside, steps lead right into the water to cool off on a hot day and a dock where you can fish and moor your boat. The unfinished basement has potential for more living space. The sunset views are waiting for you!

Listed by John Mahoney of Northwest CT Realty

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$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 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. Property has been wonderfully maintained. Walk through the front door into an open concept living room/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 with 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 driveway 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: 5.22% last updated on Aug 11, 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: 5.22% last updated on Aug 11, 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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113 Chapel Road Winchester CT 06098

MLS Number 170479300

  • Single Family
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 1,843
  • Acreage 2.3

Great opportunity to own this well cared for Cape in Winchester! Peace and quiet surround this hidden gem. Open floor plan with fireplace and eat in kitchen. Beautiful wood floors, family room. Large private deck. A garage lovers dream, room for all the hobbies. Several outbuildings.

Listed by Kelly Sullivan of Sullivan Real Estate Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

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