Off-Market Chicago Land for Local Investors
We source land across Chicago (especially the South Side) and share deals with a small group of investors we work with regularly. If you’re actively buying, let’s connect.
We’re not a big list or a dispo machine.
Dello Investments is a local Chicago operator sourcing land directly from property owners — a lot of it coming from the South Side — and working with a handful of investors to move deals that make sense.
Some deals we keep. Some we pass along.
If you’re actively buying land in Chicago and looking for consistent, straightforward deal flow, we’re always open to building the right relationships.
How We Work With Investors
We source deals directly (organic inbound through our site, mail, local outreach)
We underwrite conservatively — no inflated numbers
We share deals we’re not keeping or can’t take down ourselves
We prefer working with buyers who can move quickly and communicate clearly
This isn’t about blasting deals — it’s about repeat business with people who perform.
What We’re Seeing Right Now
Most of our land opportunities are:
South Side infill lots
Lower entry price points with upside
Scattered lots in neighborhoods like Englewood, Roseland, and South Shore
Occasional multi-lot or portfolio opportunities
We also see deals across other parts of Chicago depending on seller activity.
We spend a lot of time in areas like:
Englewood
Auburn Gresham
South Shore
Roseland
North Lawndale
Austin
These neighborhoods continue to generate opportunity — especially for investors who understand block-by-block variation, zoning, and long-term positioning.
Deal Flow Process
Step 1: We Lock Up the Property
Direct-to-seller, negotiated terms.
Step 2: We Review the Deal Internally
If it fits our criteria, we may keep it.
Step 3: We Share With Our Network
If not, we pass it along to buyers we trust.
Step 4: Assignment + Closing
Handled through a local Chicago title company.
Expectations
Deals are first come, first served
Earnest money required for serious interest
Buyers handle their own due diligence
We value speed + reliability over squeezing every dollar
Why Investors Work With Us
We’re local — not a virtual wholesaler
We don’t overpromise deal quality
We care about long-term relationships, not one-off assignments
FAQs
Are you wholesalers or investors?
Both. We buy and hold some deals, and assign others when it makes sense.
How do you decide which deals to keep?
Based on our current pipeline, capital allocation, and strategy. Some deals just fit better for other investors.
Can I get every deal you have?
We prioritize investors we’ve worked with or who can close consistently.
Do you send out big email blasts?
No — we keep our network relatively tight to avoid noise.
What kind of buyers do you prefer?
People who know their numbers, move quickly, and follow through.
Can I walk lots before committing?
Yes — we expect buyers to do their own due diligence.
Work With Us on Chicago Land Deals
We keep our buyer network relatively small and prioritize investors who can move with clarity and consistency.
If that sounds like you, fill this form out, and we’ll reach out when there’s alignment.