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Best Deals in Winchester, Connecticut

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$90,000

Residential / Single Family Residence For Sale

Days on Market: 254

51 Pratt Street
Winchester, CT 06098

4.0 Bedrooms

2.0 Bathrooms

2,239 sqft

Come check out this lovely property nicely tucked away in historic Winsted. This home features over 2,200 square feet of gross interior living space. Large kitchen, dining and living room areas is a plus. With a little TLC, this can become ones dream home. Property also featured four bedrooms and one and a half baths. Schedule your showing today before possibly missing out on this amazing deal!

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$99,900

Residential / Single Family Residence For Sale

Days on Market: 321

155 Mathew Road
Winchester, CT 06098

2.0 Bedrooms

1.0 Bathrooms

1,536 sqft

Please submit your highest and best by Monday Aug 23 2021 at 5pm . year round home close to highland lake, seasonal views in winter . short drive to town beach . Handy man special, good bones but needs updating. Main Level features living room, kitchen 2 bedrooms and bath , lower level has family room, den, laundry room and storage/ workshop . The back deck is unsafe do not walk out in back yard , lots of bees. Home will be cleaned out the next 7 days .walk in front door from gate near road, do not climb steps from driveway , that gate is locked. Private road maintained poorly by home owners , cost for plowing and repairs are suppose to be split by homeowners on this road,

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$225,000

Residential / Single Family Residence For Sale

Days on Market: 108

290 Colebrook Road
Winchester, CT 06098

6.0 Bedrooms

3.0 Bathrooms

2,979 sqft

If you are thinking of building but intimidated by all of the components of what is involved? Then look no further. We have plans for a beautiful 2900 sq ft Contemporary Cape style home and the foundation, well, septic, electrical and nice oversized barn are all in place. Literally all you need to do is pick your builder and pull the building permit. You can be in your new home for Thanksgiving. All site work is completed and this lot has a nice brook running through the rear of it. This price is for the plans and all current improvements only.

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$139,000

Residential / Single Family Residence For Sale

Days on Market: 363

24 High Street
Winchester, CT 06098

3.0 Bedrooms

2.0 Bathrooms

1,645 sqft

Looking for lots of room and character? This beautiful home offers 3 levels of finished living space. 1 1/2 baths, wood floors throughout, pocket doors, fireplace, and a grand entry. Level in town lot includes what used to be a garage and plenty of parking for everyone! Walking distance to downtown. Come see what this home has to offer!

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$175,000

Residential / Single Family Residence For Sale

Days on Market: 389

54 Hinsdale Avenue
Winchester, CT 06098

3.0 Bedrooms

2.0 Bathrooms

2,005 sqft

Beautiful older home with yesteryears charm that offers large rooms which include a large Living room, a large dining room with bay/bow windows, large eat-in kitchen, and a study that is previously used as a bedroom on the 1st floor. The second floor has three very large, spacious rooms with ample closet space. It also offers 1.5 baths and a 1 car garage and a wonderful porch where you can enjoy the summer evenings. House being sold "as is" exterior needs painting and the new price reduction reflects the proposal price from "Mountaintop Trucking" for tearing down the garage. With a little TLC this home will shine like a gem. Come take a look and bring us an offer.

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Photo by Ralph Kelly on Unsplash
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$144,000

Residential / Single Family Residence For Sale

Days on Market: 203

120 Moore Avenue
Winchester, CT 06098

3.0 Bedrooms

2.0 Bathrooms

1,602 sqft

This is wonderful home just outside of all the Shopping and Highways and the back yard is open with a nice deck. The inside just needs some cosmetic finishes, large rooms and plenty of storage. This home will only go Cash/or some Hard Money Loans and no utilities will be turned on. Seller is “Secretary of Veterans Affairs " 'may qualify for seller financing (vendee). and Unknown if the furnace works or the well. "Due to condition, the property may have health/safety risk(s). Prior to entry / access, all parties must sign a Hold Harmless Agreement and the property may only be shown by appointment" Hold Harmless is attached to this listing. Purchase as is,. Agent /Brokers All offers will be submitted through VRMProperties.com after you register.

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$129,000

Residential / Single Family Residence For Sale

Days on Market: 112

59 Hubbard Street
Winchester, CT 06098

3.0 Bedrooms

1.0 Bathrooms

1,384 sqft

HIGHEST AND BEST OFFERS DUE BY SATURDAY 3/19/22 AT 5PM. Priced to sell. Newly updated kitchen cabinetry! Tired of paying someone else's mortgage? A 1,384 square foot single family home, located on a dead end road with no through traffic, is the perfect starter home if you're tired of renting. This cute home boasts 3 bedrooms, a bonus room that can be used as an office or another bedroom, and 1 newly updated bathroom. Also great as a purchase to hold to collect rent; an investor's dream. Natural light illuminates entire home that reflects off of the hardwood and laminate floors throughout. New electric range stove top. Storage available in basement and walk-in attic. One paved parking spot in front of home, and off street parking available. Cute neighborhood. Come take a look! You won't be disappointed. Owner is negotiable. Throw out an offer!

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$147,500

Residential / Single Family Residence For Sale

Days on Market: 339

453 North Main Street
Winchester, CT 06098

3.0 Bedrooms

2.0 Bathrooms

1,488 sqft

With a little bit of elbow grease this home will shine right up. Large 1.28 acre lot with plenty of room for gardening and other outdoor activities. The home features 4 bedrooms, 1.5 baths and a 2 car detached garage. Worth a look and certainly worth the effort.

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$218,000

Residential / Single Family Residence For Sale

Days on Market: 220

59 Hinsdale Avenue
Winchester, CT 06098

3.0 Bedrooms

2.0 Bathrooms

2,124 sqft

Make your appointment today to view this gracious 3-4 bedroom home with a Victorian flair. This home has had many updates over the years and is ready to move in. Enter the home through the enclosed front porch into a delightful foyer. On the main living level, you will find the living room with newer brick fireplace, a formal dining room, both with crown moldings and hardwood floors and a beautiful kitchen and adjacent half bath. Use the staircase from the foyer or the second staircase from the kitchen to make your way to the second floor with 3 bedrooms, all with large closets, there is also a full bath at this level. You will find that the attic is fully finished and provides enough space for a fourth bedroom and yet several other multi-purpose rooms/spaces. Heat is provided by a steam boiler with vintage radiators and cooled in the summer by a two zone central air system. Conveniently located on a corner lot close to schools and shopping this home is one to be proud of.

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$139,000

Residential / Single Family Residence For Sale

Days on Market: 353

329 Colebrook Road
Winchester, CT 06098

3.0 Bedrooms

1.0 Bathrooms

1,267 sqft

SUNRISE COTTAGE is set back on lush grounds with a mountain backdrop and open and forested foreground. The home offers an open living room, kitchen, and family room. There is a first-floor bedroom and a full bath with two additional bedrooms upstairs. An enclosed porch opens to a large deck with a beautiful aboveground pool and privacy. There is an oversized garage with a workshop. The location is ideal with shopping, recreation, and activities nearby in Winsted, Norfolk, and Colebrook. The home is ready for personal enhancements. This property is being sold "as/is". Inspections are for informational purposes only.

Tour these homes now!

Call 1-855-440-1362
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Photo by Ralph Kelly on Unsplash
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$178,200

Residential / Single Family Residence For Sale

Days on Market: 158

181 Stanton Avenue
Winchester, CT 06098

3.0 Bedrooms

1.0 Bathrooms

1,594 sqft

Tremendous opportunity to own this cozy Bungalow on Stanton Ave! The property offers over 1,500 square feet of living space, 3 bedrooms and 1 bathroom. Private driveway with ample parking in the rear.

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$196,500

Residential / Single Family Residence For Sale

Days on Market: 395

344 Taylor Brook Road
Winchester, CT 06098

2.0 Bedrooms

1.0 Bathrooms

1,752 sqft

Welcome to this unique and affordable Old Style/Log Cabin Style home sitting on a 7 acre lot -- Enjoy having acreage, privacy, wildlife, and character -- So much potential here! The spacious Log Cabin addition has a metal roof and adds aprox. 900 sq ft -- cathedral ceilings, skylights, large windows bringing in tons of natural light and beautiful nature views! Home offers 2 bedrooms, 1 bath, an office space with French doors, recent updates to the Kitchen, and a separate laundry room; which could easily be converted into a larger bathroom. Newer hot water heater and well pump, non-metal part of roof and replacement windows are less than 8 yrs old. Add some finishing touches and make this home your own!

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$325,000

Residential / Single Family Residence For Sale

Days on Market: 259

100 Hinsdale Avenue
Winchester, CT 06098

4.0 Bedrooms

3.0 Bathrooms

2,799 sqft

Stately Colonial in area of beautiful older homes. Don't let the opportunity to own this fantastic piece of Winchester history go by. Sitting on over an acre of land is this wonderful home. You will first enter into a small vestibule where you will find a coat closet and a place to put your umbrellas and boots. Next, you will enter into a wide, open foyer showcasing a lovely staircase to the second floor, openings into the living room, dining room and straight back into the kitchen. The living room is a front to back room with a window seat, built-in bookcases, storage compartments, a cozy working fireplace to take the chill out of those soon to be here autumn days and the cold winter nights. Left of the foyer is a formal dining room that will welcome a large table to accommodate family gatherings that can easily spill out onto the lovely covered porch through the french doors. Off the dining room is a perfect place for your at home office, den, extra bedroom, exercise room. You can quickly access the kitchen through the butlers pantry which has an abundance of cabinets and counter space. The kitchen is large enough for a small table and chair set and you have access to a back covered porch. Don't forget to notice the in-wall ironing board and the laundry chute! Heading up the wide open front staircase you will find the primary bedroom at the front of the house which has double closets and a 3 piece attached bath. There is also direct access from the primary bedroom

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$1,195,000

Residential / Single Family Residence For Sale

Days on Market: 444

139 Grantville Road
Winchester, CT 06098

6.0 Bedrooms

5.0 Bathrooms

4,509 sqft

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!

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$189,900

Residential / Single Family Residence For Sale

Days on Market: 254

135 Marshall Street
Winchester, CT 06098

2.0 Bedrooms

1.0 Bathrooms

1,570 sqft

Move in Ready Home for any type of buyer! This home welcomes you to many indoor updates including floor to ceiling bookshelves, new windows, new appliances, new flooring, new propane furnace and a finished basement. The welcoming continues once you step outside onto the sprawling deck which is perfect for entertaining or just spending some quiet time overlooking the spacious back yard. This home is a must see !!

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