Pilsen Potential Unlocked: Prime Probate Property at 1824 S. Ashland Ave Achieves Off-Market Success

Sale at a Glance

In an inspiring example of precision matchmaking and tenacious deal-making, Triton Realty Group’s Matthew Fritzshall and Edward Liss orchestrated the off-market sale of 1824 S. Ashland Ave in Chicago’s iconic Pilsen neighborhood for $910,000. This mixed-use building, with seven large residential units and a prominent commercial storefront, had lingered in probate for years before being brought directly to a seasoned local investor. The September 2025 closing highlighted the immense value of relationships, local knowledge, and market timing, setting this transaction apart in a competitive landscape.

Sale Details

This was no ordinary sale—it was a masterclass in targeted brokerage and strategic negotiation.

Sale Price: $910,000, reflecting the property’s existing condition and untapped value
Sale Date: September 26, 2025
Buyer Profile: A trusted local private real estate company, handpicked for their experience with similar assets and established rapport with Triton
Representing Brokers: Matthew Fritzshall (President & Founder) and Edward Liss (SVP & Co-Founder), Triton Realty Group, providing dual agency for both seller and buyer
Deal Origination: Off-market transaction after years in probate, sourced through deep-rooted relationships and market vigilance
Transaction Structure: Direct placement with a single buyer, bypassing a traditional marketing process for maximum discretion and efficiency

Property Highlights

This Pilsen property stands as a beacon of opportunity, offering scale, flexibility, and future promise.

Unit Configuration: Seven expansive residential apartments and one street-level commercial unit, catering to a diverse tenant base
Corner Visibility: Strategic corner lot ensures abundant natural light for residents and maximum exposure for retail tenants
Room to Reimagine: Large unit layouts provide a canvas for modern renovations and premium rental offerings
Neighborhood Energy: Located in the heart of Pilsen, celebrated for its vibrant culture, top-tier culinary scene, and excellent public transit options
Existing Tenancies: At sale, the property featured a tenant mix that offered the buyer immediate flexibility for repositioning

Key Investment Features

1824 S. Ashland Ave represented a rare chance for transformative value creation in a coveted Chicago enclave.

Full Renovation Play: Acquired specifically for a comprehensive rehab, aligning with the buyer’s expertise and vision for high-quality urban living
Undervalued Asset: Sale price positioned to accommodate substantial capital improvements, enabling the buyer to unlock hidden potential
Market Momentum: Pilsen’s ongoing evolution as a magnet for young professionals and creatives ensures strong future rental demand
Prime Positioning: Corner location amplifies desirability for both residents and commercial occupants, boosting long-term value
Proven Partnership: The buyer’s established track record with Triton Realty Group facilitated a swift, confident transaction process

Market Strategy and Positioning

This sale was propelled by a strategy rooted in discretion, deep market knowledge, and personalized matchmaking. Rather than launching a public marketing campaign, Triton Realty Group sourced the asset off-market, recognizing the nuanced challenges it presented—probate status, multiple decision-makers, limited access, and units needing eviction or compliance. By leveraging trust and prior deal history, the brokers brought in a single, well-vetted buyer, ensuring both seller and buyer expectations were met with clarity and care. Their expertise in navigating legal, logistical, and interpersonal complexities was instrumental in delivering a seamless closing, transforming a long-dormant property into a beacon of new opportunity.

Frequently Asked Questions (FAQs)

This Pilsen probate property piqued the interest of savvy investors and local market watchers alike. Here’s what you need to know:

Q: Why was 1824 S. Ashland Ave available off-market?

A: The property had been in probate for several years, making it unavailable through traditional channels. Triton Realty Group’s local connections enabled them to identify and secure it discreetly.

Q: What challenges did the sale process face?

A: Key hurdles included gaining access to the building, resolving eviction issues, addressing non-conforming units, and coordinating among multiple sellers. Broker experience was essential in overcoming these obstacles.

Q: What are the renovation plans for the property?

A: The buyer intends a full-scale renovation to bring the building up to modern standards, enhancing both the residential and commercial spaces to attract high-quality tenants.

Q: How does the location benefit future tenants and investors?

A: Pilsen is renowned for its cultural richness, culinary hotspots, and connectivity, making it a highly desirable location for renters and businesses alike.

Q: How did broker relationships influence this deal?

A: Triton’s longstanding relationship with the buyer and deep ties in the community enabled a targeted, efficient transaction that maximized value for all parties.

Q: What impact will this sale have on the neighborhood?

A: The revitalization of this property is poised to contribute positively to Pilsen’s ongoing renaissance, offering upgraded housing and amenities while honoring the neighborhood’s unique character.