About this home

*Highest & best offers due by Tuesday 10/20 at 5 PM* Downtown convenience, classic character, and two-family potential come together at 219 Pearl Street! Wesleyan University is just a few blocks away, and Main Street's restaurants, shops, and local favorites are within walking distance! Russell Library, parks, public transportation, and convenient access to Route 9 add to the appeal. Two apartments on separate floors offer flexibility for investors or owner-occupants looking to offset housing costs with rental income. Both kitchens feature quartz countertops, with stainless steel appliances and a stackable washer/dryer in the first-floor unit. Wood flooring and generous windows bring warmth and natural light, while the second-floor screened-in porch offers a place to relax. A HUGE walk-up attic is a standout feature, offering abundant storage and exciting finishing potential for a buyer with the right vision. The sewer line was relined in 2021, a major infrastructure improvement! The paved driveway provides plenty of off-street parking, and the level rear yard adds outdoor space to enjoy. An unfinished basement, public water and sewer, natural gas, and a Navien tankless water heater installed in 2020 round out the features. Whether you're looking to house hack, generate rental income, or explore the home's untapped potential, this downtown two-family deserves a look. Make it yours today, this one won't last! --------Enjoy the energy of downtown Middletown with restaurants, coffee shops, independent stores, and community events close to home! Pearl Street puts you within walking distance of Main Street, where international dining, local favorites, and historic storefronts make an ordinary evening out feel like an occasion. Recognized by the National Trust for Historic Preservation as one of the country's most romantic Main Streets, downtown combines small-city charm with plenty to explore. Middletown's community calendar brings that setting to life with annual traditions including Cruise Night on Main Street, Holiday on Main Street, PrideFEST, and the city's waterfront Fireworks Festival. Nearby Wesleyan University adds another layer of culture through visual arts, performances, and world music events, while Russell Library offers programs and resources in the heart of downtown. Spend time along the Connecticut River, enjoy nearby parks, or head downtown for dinner without planning your whole day around the trip. Public transportation and convenient access to Route 9 make it easy to connect with surrounding towns, employment centers, and the rest of central Connecticut. For buyers drawn to a walkable downtown, an active arts scene, and a community with year-round reasons to get out and explore, Middletown has plenty to offer! *Highest & best offers due by Tuesday 10/20 at 5 PM*

Facts and features

Schools

• Macdonough School

  elementary · K-5 · 0.1 mi

  5

• Middletown High School

  high · 9-12 · 1.5 mi

  4

• Keigwin Middle School

  elementary · 6 · 1.6 mi

• Roadside Academy

  elementary · K-8 · 0.3 mi

• Beman Middle School

  middle · 7-8 · 1.8 mi

  4

• St John School

  elementary · K-8 · 0.4 mi

Price history

• Oct 9, 2026 · Listed$274,900
• Nov 12, 2020 · Sold$188,000
• Sep 28, 2020 · Listing Removed—
• Sep 7, 2020 · Relisted$190,000
• Aug 7, 2020 · Listing Removed—
• Jul 30, 2020 · Listed$189,900
• Aug 17, 2019 · Listing Removed—
• Aug 6, 2019 · Listed For Rent$950

Tax history

• 2026$5,770 tax · $141,420 assessed
• 2022$3,772 tax · $85,730 assessed
• 2021$3,772 tax · $85,730 assessed
• 2020$3,789 tax · $85,730 assessed
• 2018$3,746 tax · $85,730 assessed
• 2017$4,755 tax · $112,140 assessed
• 2016$4,620 tax · $112,140 assessed
• 2015$4,441 tax · $112,140 assessed

Home value

$297,400

• Cotality$297,400
• Collateral Analytics$308,000
• Quantarium$270,802

Where it is