Clear Investment Group

Clear Investment Group

Workforce housing-focused real estate investor

Overview

Clear Investment Group is a Chicago-based real estate investment firm that focuses on acquiring undervalued Class C workforce housing in secondary and tertiary U.S. markets. It revitalizes distressed, mid-size apartment communities through strategic renovations and in-house property management, then stabilizes and sells them to yield-focused investors or holds them long-term. The company differentiates itself through vertical integration (self-managing property, leasing, and construction) and by co-investing its own capital (about 10%) alongside limited partners, coupled with a woman-owned leadership and a history of managing over $600 million in transactions across 150+ properties. Its goal is to provide steady, attractive returns for institutional and private investors by building stabilized, cash-flowing portfolios via opportunistic, value-add investments in workforce housing, funded in part by its funds, including Clear Opportunities Fund I and the planned Fund II.

About Clear Investment Group

Simplify's Rating
Why Clear Investment Group is rated
B-
Rated B on Competitive Edge
Rated B on Growth Potential
Rated C on Differentiation

Industries

Financial Services

Real Estate

Company Size

11-50

Company Stage

N/A

Total Funding

N/A

Headquarters

Chicago, Illinois

Founded

2021

Get referred to Clear Investment Group

See people who can refer or advise you

Simplify Jobs

Simplify's Take

What believers are saying

  • Clear launched Fund II in March 2025 and targets over $200 million commitments.
  • Commercial Observer reported Clear secured a $50 million refinance for Langston Views in April 2026.
  • The July 2026 Woodland Estates purchase brought Clear's Washington-area portfolio to nearly 1,000 units.

What critics are saying

  • Syracuse sued Clear in April 2025 over Skyline, 41 violations, and habitability failures.
  • Skyline's court-ordered repairs must finish by April 30, 2026; missed deadlines trigger renewed litigation.
  • A failed turnaround at Langston Views, Woodland Estates, or Syracuse can cripple Fund II fundraising.

What makes Clear Investment Group unique

  • Clear Investment Group self-manages, leases, and constructs, controlling every turnaround lever.
  • Its 2026 acquisitions target 300-1,200 unit distressed portfolios in secondary and tertiary markets.
  • Amy Rubenstein's team buys receivership and foreclosure assets, then rebrands them into workforce housing.

Help us improve and share your feedback! Did you find this helpful?

Benefits

Health Insurance

Dental Insurance

Vision Insurance

Paid Vacation

Paid Holidays

401(k) Retirement Plan

Performance Bonus

Recently Posted Jobs

Sign up to get curated job recommendations

Clear Investment Group is Hiring for 26 Jobs on Simplify!

Find jobs on Simplify and start your career today

Don't see your dream role? Check out thousands of other roles on Simplify. Browse all jobs →