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69 Winsted, CT 06098 Houses For Sale

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$160,000Est. Payment
1 Bed | 1 Bath | 782 Sqft

115 Laurel Way, Winchester, CT 06098

House For Sale

Cozy stone fireplaced one bedroom Cabin with Vinyl sided shakes , hardwood floors ,all kitchen appliances plus washer dryer and central A/C Propane warm air heat . Pull down attic stairs . Includes a detached one room office/hobby shop with a split Heater/Air conditioner . Chimney needs liner to burn wood .

$126,000Est. Payment
4 Beds | 3 Baths | 2,031 Sqft

421 North Main Street, Winchester, CT 06098

House For Sale

Solid Antique Colonial home needs some elbow grease but well worth the effort. Large rooms gives everyone their own space. Large level yard for playing and barbecques. Town shows multi but home is being used as one family with only one kitchen, make an offer today.Minutes to the Winsted Green, Northwestern CT Community College, shopping, restaurants and beautiful Highland Lake. Shared driveway. LBP. Buyer team to conduct their own due diligence and are responsible for inspections, smoke cretifications, utility activations and any and all costs associated.

$949,000Est. Payment
4 Beds | 4 Baths | 3,401 Sqft

159 Losaw Road, Winchester, CT 06098

House For Sale

"TRANQUIL ACRES" appropriately named for this one owner custom built ten room Farmhouse Colonial. Privately set on 11.53 acres on a country road bordering the Winchester/Colebrook line. This residence consists of 3-4 bedrooms, 3.5 baths, an attached three car over sized heated garage, 18x36 inground heated pool as well as a 32X44 carriage barn with lighted cupola and adds just the right amount of country style to modern family life. The chef of the family will be impressed with the well prepped kitchen which offers custom cabinetry, granite counters, travertine back splash, under and upper cabinet lighting, propane cook top, double ovens, ss refrigerator, dishwasher, a breakfast counter and a walk in pantry. The kitchen's casual dining area is adjacent to a delightful sun room that overlooks the pool and grounds. The two story great room boasts a handcrafted floor to ceiling stone fireplace flanked by custom built cabinetry, custom glass sliders to the rear mahogany porch, terrace and pool. The master bedroom en suite is located on the first floor and quietly tucked away with no bedrooms above and features hardwood floors, a tray ceiling, an atrium door leading to the rear mahogany porch and two walk in closets. The master bathroom has a heated tiled floor, a whirlpool tub and glass shower. Both the dining and living room have french doors leading out to the spacious front mahogany porch. Sit back and relax on the front porch and take in the sounds of nature and the beautiful morning sun while having your coffee or relax in the rocking chairs. The upper level consists of two additional bedrooms, two full baths and a beautiful home office which overlooks the pool and back yard. There is bonus room space over the garage (not included in square footage). The inground heated pool was strategically designed to receive full sun all day and in the evening you get to take in a beautiful sunset beyond pool and carriage barn. The 32X44 carriage barn is attractive and compliments the main house with shiplapped knotty pine, a slate colored concrete floor, a second floor storage area and a beautifully lighted cupola set on a timer. It has plenty of space for the car collector, man cave, entertainer or hobbyist. Views of the mountains and the sunsets are spectacular. The grounds are landscaped with lush green box woods and several perennial gardens. Beautiful stone pillars and lamp posts line driveway - this meticulous home is totally private and surrounded by nature. Central Air, Andersen 400 series windows, automatic generator, alarm systems, infra-red sauna. A secluded horse farm on road for boarding or lessons. A 5 minute drive to beautiful Highland Lake - a resort lake, where you can rent a dock slip or boat and enjoy our beautiful clean lake. 2 Hrs. to NYC and Boston, 15 min. to Litchfield, 30 min. to Bradley International Airport, 40 min. to Great Barrington, MA. Wonderful restaurants, ski areas, theaters, farmers markets, state forests, hiking trails, parks, Yale School of Music & Art and shopping nearby.

$265,000Est. Payment
4 Beds | 2 Baths | 2,102 Sqft

78 Rockwell Street, Winchester, CT 06098

House For Sale

Looking for maintenance free living inside and out? Maybe a great second home within walking distance to Resha Beach and Hurtbut Cove on Highland Lake with lots of space for family gatherings and/or entertaining. A must see and new from top to bottom. The owners have spared no expense bringing this home up to date and luxurious. It was stripped and put back together from the lowest level of pouring a new concrete basement, insulating it well, installing new drywall throughout, to the top including a new roof with asphalt shingles and outside getting all new vinyl siding. Not a thing was skipped, the home receive new plumbing and electrical throughout (including the fuse box), hard wired smoke/CO2 detectors a new central air system and new hot water heater. Top of the line materials have been used including stainless steel appliances, cherry kitchen cabinets, granite counters, polished porcelain marble tiled floor and beautiful hardwood floors. Along with the 4 bedrooms the home offers a carpeted bonus room as well as an additional bonus/sitting room at the top of the stairs/landing. Outside you'll find Treks composite decks with three entrances into the home. With this large home may come a large family and/or entertaining and you'll find ample parking which is rare find in the area. So much room and so much to see. Schedule your showing now.

$1,350,000Est. Payment
7 Beds | 7 Baths | 10,123 Sqft

211 W Wakefield Blvd, Winsted, CT 06098

House For Sale

Incredible Waterfront Luxury Including Two Dwellings in 2nd Bay On Spectacular Highland Lake, a 444-acre boating lake, in Litchfield County CT. This Compound is Ideal for Multi-Generational Living or Rental Income. New England Charm abounds in this Amazing Opportunity! The Main Home has a Gorgeous Faade w Intricate Shake & Stone. Featuring a Phenomenal Expansive Floorplan Perfect for Entertaining & Enjoying Lake Living to its Fullest! 6+ Beds, 5 Full/2.5 Bths,Multiple Living Spaces,Renovated Enormous Chefs Eat In Kitchen w Two Islands, Granite, Stnls Appl, Double Ovens, Opening into Lg Dining Area, Versatile Living Options thruout incl 1st Fl Master Suite w WI Closet, & Lg Master Bth w WI Tiled Shower, Soaking Tub, & Double Sinks, Inviting Family Rm w Original Stone FP & Built Ins, Huge Living Rm/Sunrm, Heated Porch Area, Upstairs 4 Very Generous Beds incl an Enormous Bonus Rm (could also be a 2nd Fl Master), Two addt'l Full Baths Complete 2nd Fl Layout 3rd Fl is a Dream Rec/Game Space complete w Addt'l Full Bath & 2nd Lndry! Loads of Storage Space in this Home! Walkout Lower Level that is Unfinished but Fully Finishable-already plumbed, heated & ready for addt'l easy to access living space! Cottage is Direct Water Front w Panoramic Views!2 Open Flrs Family Rm w Half Bath & Upstairs Bed/Full Bth. 2 Levels of Decking to Optimize Views & Entertaining, Dock/Boat Lift are INCLUDED! Generator, Multiple Trex Decks w Views, Patios, 5+ Car Gar. Your Sanctuary At The Lake Awaits!

$1,350,000Est. Payment
7 Beds | 7 Baths | 10,123 Sqft

211/212 West Wakefield Boulevard, Winchester, CT 06098

House For Sale

Incredible Waterfront Luxury Including Two Dwellings in 2nd Bay On Spectacular Highland Lake, a 444-acre boating lake, in Litchfield County CT. This Compound is Ideal for Multi-Generational Living or Rental Income. New England Charm abounds in this Amazing Opportunity! The Main Home has a Gorgeous Faade w Intricate Shake & Stone. Featuring a Phenomenal Expansive Floorplan Perfect for Entertaining & Enjoying Lake Living to its Fullest! 6+ Beds, 5 Full/2.5 Bths,Multiple Living Spaces,Renovated Enormous Chefs Eat In Kitchen w Two Islands, Granite, Stnls Appl, Double Ovens, Opening into Lg Dining Area, Versatile Living Options thruout incl 1st Fl Master Suite w WI Closet, & Lg Master Bth w WI Tiled Shower, Soaking Tub, & Double Sinks, Inviting Family Rm w Original Stone FP & Built Ins, Huge Living Rm/Sunrm, Heated Porch Area, Upstairs 4 Very Generous Beds incl an Enormous Bonus Rm (could also be a 2nd Fl Master), Two addt'l Full Baths Complete 2nd Fl Layout 3rd Fl is a Dream Rec/Game Space complete w Addt'l Full Bath & 2nd Lndry! Loads of Storage Space in this Home! Walkout Lower Level that is Unfinished but Fully Finishable-already plumbed, heated & ready for addt'l easy to access living space! Cottage is Direct Water Front w Panoramic Views!2 Open Flrs Family Rm w Half Bath & Upstairs Bed/Full Bth. 2 Levels of Decking to Optimize Views & Entertaining, Dock/Boat Lift are INCLUDED! Generator, Multiple Trex Decks w Views, Patios, 5+ Car Gar. Your Sanctuary At The Lake Awaits!

$125,000Est. Payment
4 Beds | 2 Baths | 1,344 Sqft

159 Oak Street, Winchester, CT 06098

House For Sale

Opportunity knocks - Investors and trades take notice of this opportunity. New doors, windows, concrete floor in basement, new steel I beam, some new framing, new staircase, new deck, major demo work done and ready for final touches. Ready for electric, plumbing, kitchen, baths, drywall and finishes. House is being sold AS IS. HOME IS UNFINISHED.

$1,200,000Est. Payment
3 Beds | 3 Baths | 2,016 Sqft

426 East Wakefield Boulevard, Winchester, CT 06098

House For Sale

This custom-built year-round home offers one of the best locations on glistening Highland Lake. Enjoy over 130 of direct deepwater frontage & a southwest aspect that ensures stunning sunset views from the comfort & privacy of your very own deck. There is an impressive 2,000sqft of living space inc 3 bdrms, 2.2 baths. HW floors flow thru out the main living zone, dining area & into the EIK kitch where the home chef will discover plenty of storage w/in the custom cabinets & a suite of SS high quality appliances. The sumptuous owners suite is positioned on the 1st flr w/ direct acc out to the deck + an ensuite w/ a steam shwr & a jet tub. The laundry is also housed on this level. If you need more room, there is an add 1,250sqft walkout LL w/ tall ceilings just waiting for you to transform into any space you need. This spectacular home is set back from the street on a level 1.04-acre zoning-compliant lot. There have been a host of updates to ensure a move-in-ready abode from the updated air-conditioner (2017) to the updated furnace (2015) & the architectural roof that was installed in 2000 & has been cleaned & treated regularly. The long list of extra features continues w/ a security system should you want to use this home as a holiday hideaway, + cedar siding, an attached oversized garage, a connection to city sewer & a well, + a natural granite waterfront that eliminates the need for wall maintenance. There is hydro-air heating & a gas fireplace for your year-round comfort.

$499,900Est. Payment
3 Beds | 3 Baths | 2,696 Sqft

601 East Wakefield Boulevard, Winchester, CT 06098

House For Sale

Highland Lake-This house has 3 bedrooms-3 full baths-a 24x24 family room with gas log fireplace. Remodeled kitchen with new SS appliances & quartz countertops. Master Bedroom with slider to covered deck overlooking lake. Lower level rec room or possible in-law with full bath, gas fireplace and its own private patio. Upper level covered porch with awesome views of the lake. Rear deck overlooking private back yard. Own private lake front with dock. Two car attached garage plus a single detached garage. Short trip to Winsted or Torrington for shopping. 40 minutes to Bradley Airport and under two hours to NYC.

$669,900Est. Payment
3 Beds | 3 Baths | 2,392 Sqft

107 West Wakefield Boulevard, Winchester, CT 06098

House For Sale

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

$8,000
$149,900Est. Payment
4 Beds | 2 Baths | 1,375 Sqft

95 Hubbard Street, Winchester, CT 06098

House For Sale

HURRY ... Seller relocating & found a home . Very affordable Vinyl sided 3-4 Bedroom Colonial on cul-de-sac. City sewer/water .Recently remodeled full bath and newer high efficiency natural gas hot water heater . Huge Eat-in applianced kitchen with Island . 22x12 living room with hardwood flooring & Bay window & Replacement windows . Seller installed Black Top Driveway,new Pex plumbing & up graded electrical servise . Walking Distance to Lake , Schools and services . The Town Intends to demolish and clean up the neighboring property at 99 Hubbard St. when the legal requirements for condemnation are completed .

$24,900
$275,000Est. Payment
3 Beds | 2 Baths | 1,927 Sqft

112 Huntington Road, Winchester, CT 06098

House For Sale

METICULOSLY RENOVATED VINYL SIDED THREE BEDROOM HOME NESTLED ON 1+ SURVEYED ACRES MINUTES FROM RIVERTON CENTER AND RECREATION . PRISTINE HARDWOOD FLOORING,MAIN LEVEL HAS A FAMILY SIZE FULLY APPLIANCED KITCHEN WITH SLIDER TO HEATED GAME ROOM THAT OPENS TO DECK . OPEN LIVING ROOM WITH FIREPLACE & PICTURE WINDOW , TWO BEDROOMS AND FULL UPDATED BATH. LOWER LEVEL HAS HUGE CARPETED WALK OUT FAMILY ROOM , FULL BATH , 3RD BEDROOM AND LAUNDRY/MECHANICAL ROOM .

$184,900Est. Payment
4 Beds | 1 Bath | 1,114 Sqft

136 Glendale Avenue, Winchester, CT 06098

House For Sale

Don't miss out on this lovely 4 bedroom cape! Located in a quiet neighborhood minutes from shops and restaurants. This house boasts a spacious backyard and deck for relaxing or entertaining. Partially finished basement has tons of potential to be turned into a playroom, family room, game room, etc. The basement also has a half bath that was added by the seller. Second floor has plumbing set up in the walls for the possibility of a bathroom to be added. Two bedrooms on the main floor, either could easily be used as an office. Schedule your showing today!

$139,900Est. Payment
4 Beds | 1 Bath | 1,244 Sqft

93 High Street, Winchester, CT 06098

House For Sale

Don't miss this lovely, unique 4 bedroom antique home with tremendous character, beautiful front porch, and many remaining original features including exposed heartwood chestnut beams and spacious 21 x 11 primary bedroom. Home includes tasteful upgrades to allow for modern convenience, including new Peerless High Efficiency boiler, new chimney liner and cap, visible electrical wiring, and high efficiency washing machine all installed in 2017. Kitchen and bathroom updated with new sink faucets, lighting, and bathroom exhaust fan in 2017. In addition, kitchen GFCI updated and new vinyl flooring installed in 2017. New asphalt roof within the past 5+- years, shallow roof over unheated attached storage space (22 x 11) has ice/water dam covering and extended under clapboards approximately 2 feet. Wireless security and outside lighting systems installed within the past 5+- years. Usable level yard with great location! Close proximity to restaurants, shopping, schools, medical facilities, and village center -- Won't last!!!

$185,000Est. Payment
4 Beds | 2 Baths | 1,644 Sqft

43 John Street, Winchester, CT 06098

House For Sale

You will not want to miss this beautiful 4 Bedroom, 2 bath, colonial home on a corner lot! Featuring tall ceilings, large windows and hardwood floors. This home has been updated inside and out. New roofing, gutters, energy efficient windows, electric dog fence, ceiling fans, flooring, furnace, water heater, central air, gas pipes, exterior stairs, plus a freshly paved driveway and sidewalk. Both Bathrooms have been recently remodeled. The main bath is spacious with double sinks and laundry right down the hall from the bedrooms. The carriage house was updated recently with a new roof and supports, and has enough room for all your toys!

$199,999Est. Payment
6 Beds | 3 Baths | 2,974 Sqft

117 Holabird Avenue, Winchester, CT 06098

House For Sale

Large and spacious almost 3,000 sq. ft 6 bedroom 3 full bathroom single family house with lots of flexibility to suit your needs (perfect for working or schooling from home). 1900 house charm still present with two original fireplaces and pocket doors on first and second floor. In town access within walking distance to local restaurants and Northwestern Community College with roomy back yard on .40 acres with a few budding fruit trees and room for raised beds and much more. Brand New completely remodeled kitchen in 2020 with newer GE Profile Appliances: Refrigerator, dishwasher, microwave and double oven. Entire house electrical upgraded in 2015 as well as insulation and drywall on first two floors. Spacious with flexible configuration, First floor has a Kitchen, dining room and two other living rooms as well as a full bathroom with walk-in shower. One living has pocket doors and could serve as a bedroom. 2nd Floor has 4 sizable bedrooms and a full bathroom. 3rd Floor has one bedroom, one full bathroom, area with sink and stove hook-up and a large open room that could be configured for an additional bedroom. 2nd and 3rd floor accessible from outside stairwell. Basement has a kitchen with sink and stove with full cabinet array. Second portion of basement is unfinished that offers storage or even possible work area. Spacious remodeled wrap around porch around 400 square feet. Home does need some cosmetic TLC but priced to sell!

$10,000
$139,900Est. Payment
2 Beds | 3 Baths | 965 Sqft

35 Laurel Street, Winchester, CT 06098

House For Sale

This 2 bedroom 1 full and 2 half bath home is a great alternative to a condo and sits just two blocks from the beach at Highland Lake. New roof just installed. The main living level contains a nice maple kitchen with granite counters, combination LR/DR, bedroom and an updated full bath. Upstairs is a modest bedroom with attached office or possible third bedroom and a half bath. The walk out lower level could easily be finished as a family room with a half bath.

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