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$749,900
2 Beds 1 Baths ACTIVE Status 24192463 MLS
Year-round waterfront retreat with breathtaking sunrise views from one of the widest sections of the lake! This well-maintained 2-bedroom, 1 bath home offers comfortable living with a flexible loft area for additional sleeping space and a convenient half bath on the lake level. The updated kitchen and new windows provide modern comfort while showcasing expansive water views throughout the home. Outdoor amenities include a spacious waterfront patio, outdoor shower, and walk-in staircase for easy water access, making it ideal for swimming, boating, and relaxing lakeside. Adjacent to a state park, the property enjoys a picturesque setting with added privacy and natural surroundings. Move right in and enjoy as-is or update to suit your personal style. An additional parcel across the street is included, providing extra space and excellent long-term potential. Whether you're looking for a year-round residence, vacation getaway, or investment opportunity, this waterfront property offers an exceptional combination of location, views, and lifestyle.

812 W Wakefield Blvd, Winchester

$389,900
3 Beds 2 Baths ACTIVE Status 24184417 MLS
Welcome to East Lake Street at Highland Lake, where privacy, comfort, and lake living come together. Set back from the road on a private lot in the desirable First Bay area, this well-maintained lake-style home offers a quiet setting with seasonal lake views and refreshing breezes throughout. Offering 1,820 square feet, the home is listed as a 3-bedroom with a first-floor finished 4th room for added flexibility. The updated kitchen features quartz counter tops, stainless steel appliances, and ample cabinetry, with warm pine ceilings adding character throughout. Additional features include two full baths, first-floor laundry, newer windows, public water and sewer, natural gas, on-demand hot water, and a wood stove. Outside, enjoy a peaceful backyard garden and convenient rear access from Ontario Street. Located within one mile of local schools and a half mile of town, the home offers easy access to everyday amenities while maintaining a peaceful lake setting.

132 E Lake St, Winchester

$499,900
6 Beds 5 Baths ACTIVE Status 24178149 MLS
Charming Multi-Family Property with steady income potential! Welcome to your next lucrative investment venture! Nestled on an expansive 1-acre lot, this multi-family property features 5 distinct living spaces, making it an ideal addition to your real estate portfolio. This property comprises 4 studio apartments and a spacious 2-bedroom apartment, catering to a variety of tenants and maximizing rental income. With a current monthly gross income of $4,200, you can enjoy steady cash flow while benefiting from an increasingly competitive rental market. Located in a desirable neighborhood with public water and access to public sewer, this property is perfectly positioned to attract long-term tenants. Its proximity to local amenities, schools, and public transportation enhances its appeal, ensuring high occupancy demand. Each unit boasts separate electrical meters, providing tenants with individual control over their utilities. The common laundry facilities in the basement offer added convenience for residents, further enhancing the livability of the space. Recently paved parking enhances accessibility for both residents and guests, while dual heating units ensures comfort during colder months. This property is not only inviting but also functional, providing a hassle-free living experience for tenants. It also comes with established tenants, solid rental history, and a reliable mechanicals, allowing you to step into a well-oiled investment without the headaches of initial setup.

205 Old New Hartford Rd, Winchester

$549,000
11 Beds 6 Baths ACTIVE Status 24166332 MLS
*PRICE REDUCTION* 150 Oak St. is a fully rented, rare, charming 1920's 5-family apartment home located in a beautiful residential neighborhood in Winsted/Winchester, CT. Old World charm with original woodwork, high ceilings, mostly hardwood floors, and hallways connecting the spacious rooms in 4 of the units -which feature 2 bedrooms and a dining room. The 5th floor is a 3-4 bedroom, 1 1/2 bath unit with electric H&HW. There is a 4-bay detached garage -some rented separately. 1 garage bay is rented to a non-tenant at $65/mo. A great investment opportunity! New since between 2021-2023: roof, 4 hot water heaters and 3 furnaces! Walking distance to Northwestern CT Community College and Downtown Winsted. Nearby shopping, indoor and outdoor activities. Easy commute to Rte 8 South and Rte 8 North to Western MA Pioneer Valley towns and the Berkshires. @ 25 miles to Rte 20 and Becket, MA. Several more miles on Rte 20 to the Lee Outlet and the MassPike!

150 Oak St, Winchester

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