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264 Florence St, Winchester
$265,000
3 Beds ⋅ 2 Baths ⋅ COMING SOON Status ⋅ 24213670 MLS
Charming 3 bedroom 2 bath Cape, Oil heat with Natural gas connected if you'd prefer to switch over at some point. Nicely landscaped yard, repl windows, propane insert fireplace, wood floors, wired for a portable generator, new garage door (2025), furnace (2003), hot water heater (2026), 100 amp service, Central air. Well established, wonderful neighborhood, priced to sell. Rare opportunity to downsize or realize the dream of your 1st home!

264 Florence St, Winchester
240 Florence St, Winchester
$264,900
2 Beds ⋅ 1 Baths ⋅ COMING SOON Status ⋅ 24213928 MLS
Make yourself at home while exploring the possibilities this property has to offer. Fresh paint in both bedrooms, the bathroom, and hallway, along with refinished hardwood floors in both bedrooms, gives the interior a refreshed feel. Enjoy the enclosed porch, three garage spaces for vehicles or hobbies, and a spacious unfinished attic with potential for additional living space additional living space. Features include replacement windows, 200-amp electrical service, an on-demand hot water heater, and a furnace installed in 2016. Home is generator ready. The sale includes two 0.55-acre parcels totaling approximately 1.10 acres, offering additional outdoor space to enjoy. Enjoy privacy, an expansive yard, and room to garden in a convenient Winsted location. Existing garden beds offer a head start for growing vegetables or flowers, with plenty of outdoor space for entertaining or simply relaxing.

240 Florence St, Winchester
205 Perch Rock Trl, Winchester
$350,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24210637 MLS
Valued by Redfin at $497,000 and Realtor at $516,000 - this house is a gem! 205 Perch Rock Trail, a spacious 4-bedroom, 2.5-bath home in the highly desirable Highland Lake area of Winsted. New siding and roof October 2026. Offering an incredible combination of space, location, and value, this property is a rare opportunity for a buyer looking to create something special. The home needs renovations and is being sold As Is, but the potential is substantial.The home offers approximately 2,369 square feet of living space, including a finished lower level with a kitchenette and full bath - ideal for an in-law setup, guest suite, home office, recreation space, or extended-family living. Enjoy lake views, nearby water access, a private backyard, two fireplaces, a balcony, generous storage, and an under-house garage. Public water and public sewer. With 4 bedrooms, multiple living areas, and flexible lower-level space, the possibilities here are exceptional. Whether you are looking for a year-round residence, weekend lake retreat, renovation opportunity, or investment property, 205 Perch Rock Trail offers tremendous upside. Bring your vision and make this Highland Lake gem your own!

205 Perch Rock Trl, Winchester
150 E Lake St, Winchester
$449,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24208283 MLS
Enjoy lake living with this inviting 3 bedroom, two and a half bath home located directly across the street from Highland Lake. Offering water views and a convenient location, this property is a wonderful opportunity for a year round residence or weekend getaway. The home features a two car garage and plenty of parking and storage. Enjoy the convenience of having two beaches and a boat launch within walking distance, making it easy to spend your days swimming, boating, fishing, or simply relaxing by the water. Come take a look!

150 E Lake St, Winchester
50 Palmer Ave, Winchester
$429,000
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24206936 MLS
Originally built in 1940, this charming Cape has been completely transformed-taken down to the studs and thoughtfully renovated from top to bottom, blending classic character with the comfort and style of a modern home. The inviting open floor plan features a gorgeous kitchen with a large center island, granite countertops and stainless-steel appliances, flowing seamlessly into the spacious living area. The main-level primary suite is a true retreat with its own fireplace and private full bath. A convenient laundry room completes the first floor. Upstairs, you'll find two generously sized bedrooms and a beautifully updated full bath. The renovated lower level provides additional usable space and includes a garage bay under the house. Adding even more versatility is a detached two-car garage equipped with heating and air conditioning-ideal for a workshop, hobby space, car enthusiast or additional storage set in a peaceful location with a park directly across the street, this beautifully reimagined home offers the charm of a 1940 Cape with the extensive updates and functionality today's buyers are looking for. Truly move-in ready and a must-see!

50 Palmer Ave, Winchester

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