About this home

Investor package - 299 Oak St is sold together with 301 Oak St (see related MLS listing 24218005); package price $369,900 for both parcels, this listing reflects the allocation for 299 only. Two-family built 1889 with a separate studio over the detached garage. Both apartments are 2 bed / 1 bath: the first floor is intact and needs cosmetics; the second floor kitchen and bath are gutted, the rest is cosmetic. Flat-roof rear addition takes on water and the roof is likely due; stone basement; three electric panels; electric heat. Studio over the garage is gutted. Next door, 301 Oak St is a one-story 3-unit with two fully renovated apartments - six potential units across the package, buyer to verify unit count and zoning with the City of Waterbury. Strictly as-is. Cash or hard money only. Bring your contractor and your vision.

Facts and features

Schools

• Woodrow Wilson School

  elementary · K-5 · 0.2 mi

  3

• Crosby High School

  high · 9-12 · 2.7 mi

  1

• Michael F. Wallace Middle School

  elementary · 4-8 · 2.7 mi

  4

• Impact Christian Academy

  elementary · K-5 · 0.8 mi

• Waterbury Career Academy

  high · 9-12 · 0.2 mi

  7

• Woodrow Wilson Bdlc

  elementary · 1-5 · 0.2 mi

Price history

• Oct 30, 2026 · Listed$166,900
• Feb 19, 2020 · Sold$100,000
• Nov 22, 2019 · Listing Removed—
• Oct 29, 2019 · Listed$184,900

Tax history

• 2026$4,651 tax · $107,310 assessed
• 2022$4,218 tax · $70,050 assessed
• 2021$4,218 tax · $70,050 assessed
• 2020$4,218 tax · $70,050 assessed
• 2019$4,401 tax · $73,090 assessed
• 2018$4,401 tax · $73,090 assessed
• 2017$4,431 tax · $73,600 assessed
• 2016$4,431 tax · $73,600 assessed

Where it is