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57 Sunnyside Ave, Watertown
$359,900
4 Beds ⋅ 2 Baths ⋅ 24209970 MLS
ATTENTION INVESTORS & OWNER-OCCUPANTS! This longtime-owned two-family in the Oakville section of Watertown offers a unique opportunity with multiple possibilities. Set on a beautiful & spacious 1.17 acres, the property is ideal for an owner-occupant, investment, or multi-generational living arrangement. The second-floor owner's unit is filled with charm and character, featuring one bedroom with a bright bonus room right off of it flooded with natural light-perfect for a home office, art room, library and reading sanctuary or quiet retreat. The living room offers hardwood floors and a custom cherry built-in wood cabinet, while the partially finished third-floor attic includes two additional rooms with built-in beds and dressers. The first-floor apartment is ready for its next chapter, with much of the space already gutted to the studs, insulated and prepared for renovation. Major updates include a newer furnace, hot water heater, updated electrical and replacement windows. Add a welcoming front porch with the original antique carved hardwood front door with custom glass window, carport, off-street parking and convenient access to Route 8, I-84, shopping and area amenities. Bring your vision and make this unique property your own!

57 Sunnyside Ave, Watertown

19 Pythian Ave, Watertown
$435,000
8 Beds ⋅ 3 Baths ⋅ 24209524 MLS
ASSUMABLE MORTGAGE 5.5%. Investor-ready three-unit multifamily offering strong cash-flow potential in Watertown. 19 Pythian Avenue features two spacious side-by-side 3-bedroom units, plus a fully finished lower-level 2-bedroom unit, creating multiple income streams under one roof. This property is built for an investor looking for a straightforward addition to their portfolio - collect the keys, collect the rents, and start generating income. Major improvements include a roof approximately three years old, helping reduce near-term capital expenditure concerns. A standout feature is the property's solar system, which provides an additional income stream to the landlord through energy sold back to the grid, currently generating approximately $640+ per month. Combined with rental income from all three units, this creates an attractive opportunity to maximize the property's overall revenue potential. The property also offers convenient off-street parking and a practical multifamily layout that supports strong tenant demand. Whether you're expanding an existing portfolio, purchasing your first multifamily investment, or looking for an income-producing property with multiple revenue streams, 19 Pythian Avenue presents a compelling opportunity in Watertown. Three units. Multiple income streams. Parking. Newer roof. Solar revenue. Ready to cash flow. SOLD AS IS

19 Pythian Ave, Watertown

77 Westbury Park Rd, Watertown
$379,000
4 Beds ⋅ 2 Baths ⋅ 24187591 MLS
Investors delight! A Prime, downtown located, aesthetically appealing, 1500 sf+, 2 family w/ ample off street parking, just oozing with potential! This 1915 home has stood the test of time and welcomes your finishing touches to restore her luster to generate optimal passive income. Previously utilized as a single family residence, this balanced estate can easily be converted back with minimal investment. Each unit offers a main level eat in kitchen, a generous family room with front porch access, and spacious rear sunroom. Units upper living space adorns 2 commodious bedrooms and full bathrooms. Bring your vision as you convert and transform this home to optimize investment income! This jewel of an investment is ripe for the taking!

77 Westbury Park Rd, Watertown

805 Main St, Watertown
$3,668,000
7 Beds ⋅ 3 Baths ⋅ 24185537 MLS
Rare opportunity to acquire a well-maintained 28-unit multifamily portfolio spanning 8 buildings across 4 tax parcels in Watertown, CT. The portfolio includes 15 Pythian Ave, 20 Pythian Ave, 28, 38, 48, 58 and 68 Atwood Court, and 805 Main St. Under single ownership for five years, the current owner has completed significant capital improvements including new roofs, siding, and porches throughout, with the majority of units already renovated. At 96.4% occupancy, long-term tenants have kept rents below market, creating immediate upside as units turn over. Current rents generate $32,665/month across a diversified mix of 1, 2, and 3 bedroom units. At $3,668,000 ($131K/door), the property delivers a 7.54% in-place cap rate on current signed leases. Watertown boasts a median household income of $103,200, well above neighboring Waterbury, supporting strong and consistent rental demand. Quiet, private setting within walking distance to local retail. Simple 4-parcel closing structure. Turnkey value-add with the heavy lifting already done.

805 Main St, Watertown

87 Woodruff Ave, Watertown
$345,900
4 Beds ⋅ 2 Baths ⋅ 24184144 MLS
Welcome home to this beautiful two-family property located in the heart of Watertown. Sitting on a spacious .66 acre lot, this home offers a perfect blend of comfort, space, and convenience. The first floor features three bedrooms, a full bathroom, a bright living room, a formal dining room, and a well-appointed kitchen-ideal for everyday living or entertaining. Upstairs, the second unit offers three bedrooms, a full bathroom, a cozy living room, a dining area, and a functional kitchen with a walk-in pantry, providing a great layout for extended family or rental income potential. Located just a short walk from Watertown's vibrant downtown, you'll enjoy easy access to local shops, restaurants, parks, and public transportation. Whether you're looking for an investment opportunity or a place to call home, this property has it all.

87 Woodruff Ave, Watertown

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