Prestige. Growth.
Lasting value.
Prosperity Group is an approved Keller Williams expansion team in commercial real estate. Chicago is the brain; the map is the market. We connect owners, brokers, and well-capitalized funds with funding to deploy, in the metros and the tertiary markets beyond them.
No. 1 U.S. real estate franchise brand (T3 Sixty Real Estate Almanac 2026) · No. 1 brand by sides and volume (RealTrends Verified 2026)
Core Offerings
National commercial real estate expertise spanning acquisitions, investment sales, leasing, and value-add execution. We connect a national network with local market intelligence and stay involved to help advance your investment plan.
INVESTMENT SALES
Position your property for a successful sale with informed pricing, targeted marketing, and buyer outreach through our national real estate network. We guide owners through negotiations and closing with a strategy built around their objectives.
ACQUISITIONS & DEAL SOURCING
Our strategic partners have priority buy boxes and capital ready to deploy. Bring us the rent roll and the P&L; we underwrite fast and answer in days, not quarters.
LEASING & OCCUPANCY
Turn available space into your next opportunity. Through property positioning, targeted tenant outreach, and lease negotiations, we help owners backfill vacancies, strengthen tenant mix, and align leasing decisions with their investment strategy.
VALUE-ADD STRATEGY & EXECUTION
Our involvement continues beyond closing. We work alongside investors and their project teams to help execute repositioning plans, identify opportunities to improve property performance, and advance the business plan throughout ownership. We stay through the hold period.
The Prosperity Standard
Clear communication, disciplined execution, and a seat at the table after closing — backfilling vacancies, repositioning, and advancing the value-add plan. Brokers are welcomed and protected here; share an opportunity with confidence.
Selected Closed Transactions
Built on Chicago's South Side and grown across the Midwest: multifamily, mixed-use, and retail, valued honestly and repositioned with the owner.
5228 S. Blackstone Ave
South Side Multifamily Portfolio
5451–61 S. Everett Ave
1507 N. Sedgwick
Single assets, portfolios, and notes.
$2M–$15M. Retail centers, warehouses, multifamily, self-storage. Flexible enough to make deals work with vacancy between 60–80%. We love tertiary markets — that's where the story is.
- Share the asset.
- We underwrite — a rent roll and a P&L is enough.
- A range in days, a firm offer in 24–48 hours with full information.
- Deal team assembled.
- Close, and we stay through the hold period.
If you had a million dollars you had to invest in this property, where would you put it? Our partners can be the capital that puts it there.
Grow your commercial practice.
Top commercial agents, not exclusively Keller Williams. Give us a focused day a week inside our models and systems and you can and may grow your existing production. We are not a lead service — we equip agents with strategy, tools, and the network to grow their commercial practices.
Meet the director who opens the door: Rashauna Scott →Not a lead service
We equip agents with strategy, tools, and the network to grow their commercial practices — a focused day a week inside our models and systems.
Prosperity is a group project.
Every opportunity we work has a market center, a brokerage team, an industry body, and a well-capitalized partner behind it.
Let's talk.
2211 N. Elston Ave. #400, Chicago, IL 60614 · (312)-815-2232 · investment@kwcommercial.com
Connect With Prosperity Group
Share an opportunity or talk to our team about joining.