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Best Deals in Winchester, Connecticut

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$729,000

Residential / Single Family Residence For Sale

Days on Market: 468

62 Lakeview Road
Winchester, CT 06098

5.0 Bedrooms

4.0 Bathrooms

4,709 sqft

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.

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$219,500

Residential / Single Family Residence For Sale

Days on Market: 276

15 Baker Street
Winchester, CT 06098

3.0 Bedrooms

2.0 Bathrooms

1,416 sqft

Newly remodeled Cape featuring spacious backyard with large patio and firepit. The lot also offers perennials gardens, fruit trees, blueberry bushes and grapevines. This three bedroom, two bath home has been well loved and cared for, we have given it a new face with brand new roof, siding, windows, and doors. Luxury vinyl has been put throughout, as well as the addition of a new woodstove. Located on a quiet street minutes away from schools and easy access to route 44. It is also close to multiple state parks, paved walkways and biking trails.

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$129,900

Residential / Condominium For Sale

Days on Market: 416

111 Riverton Road #70
Winchester, CT 06098

2.0 Bedrooms

2.0 Bathrooms

1,204 sqft

Welcome home to this charming two bedroom Condo in River Walk! The interior features a wonderful open floor plan with a bright kitchen, sliders to the deck overlooking the beautiful yard, comfortable living room with fireplace, beautiful hardwood floors, a large master bedroom and attached 2 car garage with new upgraded, insulated doors. Minutes to shops, restaurants and highways making this a great commuter location! Don't miss this incredible opportunity! Why rent when you can own?

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$139,900

Residential / Single Family Residence For Sale

Days on Market: 118

151 East Wakefield Boulevard
Winchester, CT 06098

3.0 Bedrooms

1.0 Bathrooms

946 sqft

Nice 2-3 bedroom ranch with views of and within walking distance to the beach at Highland Lake. These owners have owned this home for over 4o years and have nicely maintained it. Great affordable starter home or great for a year round weekend escape. Here today and gone tomorrow.

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$127,900

Residential / Condominium For Sale

Days on Market: 300

111 Torringford Street #7
Winchester, CT 06098

2.0 Bedrooms

2.0 Bathrooms

1,156 sqft

Clean and neat! Very well maintained unit. Master bedroom and a full bathroom are located on the main level, along with the kitchen and combination living room/dining room and a slider to private back deck. Second level has a second bedroom and another full bath. Large loft area in the upper level with skylight could be used as a bedroom or office space. Gas heat and hot water except in the loft which has electric heat. Basement is unfinished and offers plenty of storage.

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$315,000

Residential / Single Family Residence For Sale

Days on Market: 416

115 Chapel Road
Winchester, CT 06098

3.0 Bedrooms

2.0 Bathrooms

1,962 sqft

A superb opportunity to enjoy a secluded but convenient home located in the countryside of Winchester Center. This home features 3 bedrooms and 1.5 baths. The fresh open floor plan is accented with wide wood flooring, French doors that lead to a modest deck and a two sided brick fireplace between the living and dining rooms. The kitchen has a gas cooktop range, plenty of light wood cabinets and a breakfast bar. Generous sized bedrooms and one that has a small deck.  An abundance of windows make this home light and bright. Also includes a two car walkout garage. There is mountain laurel blooming around the house giving a feeling of serenity. The property is close to the center of Winsted, Platt Hill State Park and Highland Lake. Platt Hill State Park offers 159 acres with hiking trails, picnicking sites, and views of the surrounding area. Highland Lake is famous for its fishing, boating, swimming and water sports opportunities. With easy access to highways, less than two hours from NYC, 2 hours into Boston, 40 minutes to Bradley Airport.

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$164,900

Residential / Single Family Residence For Sale

Days on Market: 353

114 Colony Drive
Winchester, CT 06098

3.0 Bedrooms

2.0 Bathrooms

1,008 sqft

Make no mistake this property is in "as is" condition. Build sweat equity in this 3 bedroom ranch with a bath and a half, fireplace in the living room with a bay window, slider to ground level deck. New roof 2020, oil HWBB heat, 1 car garage under, room for expansion in the lower level. This home will not quality for a government loan unless it is a rehab loan,

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$265,000

Residential / Single Family Residence For Sale

Days on Market: 336

101 Laurel Way
Winchester, CT 06098

3.0 Bedrooms

2.0 Bathrooms

1,618 sqft

Set on a country road above Highland Lake, is this 3 bedroom, 2 bath Cape Cod style home idyllically set 3 open, level acres. Bring the animals! The eat-in kitchen features granite counters, stainless appliances and new flooring. The living room has hardwood flooring, a lovely bay window and a wood stove if you want to save on heating costs. There are 2 more rooms on the main level plus an full bath. The upper level features a large master bedroom & bath with a large walk-in closet. There is another room on the upper level that can be used as an bedroom or home office . The house also features a whole house generator and tankless propane water heater. The property is ideal for gardening and keeping animals. There is a small barn with water and electricity and another outbuilding. It is less than 15 minutes to shopping, restaurants, major commuter routes, Highland Lake, Ski Sundown and other recreational activities.

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$269,900

Residential / Single Family Residence For Sale

Days on Market: 131

148r Mountain Road
Winchester, CT 06098

3.0 Bedrooms

2.0 Bathrooms

1,728 sqft

Welcome home to privacy, situated on 2.84 acres! This well cared for bright 3 bedroom, 2 full bathroom home features many updates including a year old roof, freshly painted siding and interior, a spacious deck, recently replaced well pump, updated electrical, and hardwired smoke detectors. Inside you are greeted by inlaid hardwood flooring and a kitchen featuring corian countertops and a spacious granite island with seating. The lower level contains a bonus room with plently of space for all your hobbies, schedule your showing today!

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$329,900

Residential / Single Family Residence For Sale

Days on Market: 475

180 East Lake Street
Winchester, CT 06098

3.0 Bedrooms

2.0 Bathrooms

1,955 sqft

Old world charm fully updated 3 bedroom 2 full bath year round home overlooking Highland Lake. Enjoy the fabulous view of the lake while sitting out on your front porch enjoying an afternoon refreshment or just chilling out. This home is situated steps away from the boat marina and 2 public beaches. Enjoy all of the activities Highland Lake has to offer for a fraction of the taxes of waterfront property. This home is truly in move in condition. It has hardwood floors throughout, updated Kitchen and bathroom, huge laundry room on the main level, fully fenced in yard that is perfect for entertaining family and friends. This one won't last!!

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Call 1-855-440-1362
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Photo by Ralph Kelly on Unsplash
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$169,900

Residential / Single Family Residence For Sale

Days on Market: 142

123 Stanton Avenue
Winchester, CT 06098

3.0 Bedrooms

1.0 Bathrooms

1,040 sqft

A little paint will go a long way. This 3 bedroom ranch is located close to all conveniences and is in very nice condition. Windows are fairly new and the roof is a 35 year architectural shingle this is only 11 years old. The walk out lower level with one car garage is easily finished for more living space. Other features are a fireplace in the living room and a walk up attic.

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$179,900

Residential / Single Family Residence For Sale

Days on Market: 310

271 Colebrook Road
Winchester, CT 06098

2.0 Bedrooms

1.0 Bathrooms

1,040 sqft

Beautiful country setting with open meadow views is where you'll find this 2 bedroom, 1 bath ranch with laundry/utility room on main level. Clean, neat and tidy plus a 11x16 enclosed seasonal porch with brick grill. Property will transfer "as is ". All windows on porch do not all open. Well is located in the back under pedestal for bird bath. Septic is in front of home. Furnace is serviced annually. *** Watch the Virtual Tour ***

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$329,000

Residential / Single Family Residence For Sale

Days on Market: 359

113 Hollow Hill Road
Winchester, CT 06098

2.0 Bedrooms

2.0 Bathrooms

1,872 sqft

PRIVACY IN WINCHESTER CENTER - Tucked away off of peaceful Hollow Hill amidst stone walls in a classic New England setting, you'll find this well kept one owner Colonial with a unique, versatile layout. The 240 sq ft heated recreation room, which is not included on the town assessor's tax card, brings the total square footage to 2,112. An interior balcony, a Den that could serve as a Guest Room or 3rd Bedroom, a spacious Rec Room, a brick hearth fireplace - there is a lot to enjoy here. Minutes from kayaking and fishing at Park Pond or Winchester Lake, power boating and the town beach at Highland Lake, and all of the outdoor recreation available in the Litchfield Hills, this is an ideal location to enjoy all that the area offers. Winsted's Gilson Theatre, The Infinity Theatre and the Yale Summer Music series in Norfolk, farm to table restaurants throughout the region are just the beginning. Come see for yourself!

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$122,500

Residential / Condominium For Sale

Days on Market: 188

45 Riveredge Drive #45
Winchester, CT 06098

2.0 Bedrooms

2.0 Bathrooms

992 sqft

Well cared for Two Bedroom Once and Half Bath Condo in move in condition. The Kitchen features Classic White Cabinets with SS appliances and Tile Flooring. Living Room and dinning area features Laminate Flooring with the slider to private back patio. Dining and entertainment and recreation are only a few minutes away. There is fun for all seasons!! The garage offers additional storage. Don't miss this Condo.

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$279,000

Residential / Single Family Residence For Sale

Days on Market: 172

27 Lanson Drive
Winchester, CT 06098

2.0 Bedrooms

1.0 Bathrooms

1,548 sqft

Awesome opportunity to own 2 homes on one lot AND a commercial space for storage. This property features a ranch style move in shape 2 bedroom 1548 sq ft home with hardwood floors, open floor plan, fireplaced living room and large dining room. Main bedroom includes an additional sitting room 10x7 for a home office or dressing room. There is both a living room and a family room/den/ If you love the knotty pine look and hardwood floors, this home is for you! Thermal paned windows, newer furnace and new roof... The second 1 bedroom home is currently rented to a tenant of 30yrs for $700, month to month and includes a separate garage. There is also a commercial storage facility that needs repairs but currently rented month to month for $650. Unique Property!!! Subject to court approval.

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