
Visionary Off-Market Multifamily Acquisition: 16-Unit Legacy Building Sells in Andersonville Amid COVID Uncertainty
Sale at a Glance
In a bold, off-market transaction that captured both heart and strategy, 5424-5426 N. Ashland Ave. was acquired for $2.3 million on September 14, 2020. Triton Realty Group’s President & Founder Matthew Fritzshall guided a local investor to secure this 16-unit gem in Andersonville—a building held by the same family for decades. The sale, orchestrated during the height of the pandemic, stands as a testament to intuition, relationships, and the magnetic pull of Chicago’s north side multifamily market.
Sale Details
This transaction exemplified the power of local knowledge, swift execution, and trust in uncertain times.
Sale Date: September 14, 2020
Sale Price: $2,300,000
Buyer Broker: Triton Realty Group, Matthew Fritzshall (President & Founder)
Seller Representation: Residential agent entrusted with the listing through a family connection
Buyer: Private local investor with existing neighborhood holdings
Seller: Multi-generational family ownership, reflecting deep neighborhood roots
Total Units: 16 residential apartments
Unique Approach: Direct, pre-market negotiation bypassed traditional listing competition
Property Highlights
This stately, corner-lot building radiates classic Andersonville charm and enduring investment appeal.
Expansive Corner Lot: Maximizes natural light, privacy, and curbside visibility—inviting prospects and tenants alike
Architectural Integrity: Decades of family stewardship preserved vintage details, hardwood floors, and original layouts
Spacious Layouts: Generously sized units, a rarity in the current apartment landscape
Community Connection: Located in one of Chicago’s most vibrant, walkable neighborhoods—steps from Clark Street’s boutiques, grocers, and nightlife
Long-Term Stability: Quality tenants and minimal turnover, reflecting the asset’s reputation and desirability
Key Investment Features
A rare convergence of scale, location, and upside potential sets this property apart for the discerning investor.
Portfolio Expansion: 16 units in a single acquisition offers immediate scale for multifamily investors seeking critical mass in a top submarket
Value-Add Opportunity: Untapped potential for interior renovations, amenity upgrades, and rent optimization
Strong Fundamentals: High occupancy and resilient demand, even amid pandemic challenges
Future-Proof Location: Andersonville’s status as a destination neighborhood provides insulation against market swings
Legacy Asset: First time available in generations, signaling a unique chance to steward a piece of neighborhood history
Market Strategy and Positioning
This sale was rooted in proactive vision and deep local ties. Rather than waiting for the property to be broadly marketed, Matthew Fritzshall of Triton Realty Group identified the asset’s latent promise and reached out directly to the family ownership, establishing trust and a shared sense of timing. The buyer, already invested in the area, recognized the once-in-a-decade nature of the opportunity and moved decisively. By sidestepping the conventional listing process, both parties avoided uncertainty and competition, achieving a full-price closing in the midst of Chicago’s COVID lockdowns. Navigating tenant communications and access was handled with sensitivity, ensuring a smooth transition despite unprecedented logistical hurdles.
Frequently Asked Questions (FAQs)
This Andersonville sale is a case study in why local expertise and relationships matter—especially in uncertain times.
Q: What drew the buyer to this particular Andersonville property?A: The building’s pedigree, corner location, and untapped value-add potential made it a compelling target for growth-focused investors looking for solid returns and neighborhood stability.
Q: How did this deal avoid the challenges of a competitive, open-market process?A: By engaging directly with the seller pre-listing, the buyer leveraged Triton Realty Group’s relationships and market insight, creating a low-drama, high-trust environment that accelerated the deal.
Q: What were the most significant hurdles to overcome during the pandemic?A: Coordinating tenant access for inspections and walkthroughs required careful negotiation and empathy, ensuring safety while maintaining momentum.
Q: Why is Andersonville considered a resilient multifamily market?A: The neighborhood’s unique mix of independent businesses, cultural vibrancy, and strong sense of community continues to attract renters and investors, even through economic downturns.
Q: What should future investors know about buying in a legacy neighborhood like this?A: Opportunities to acquire multi-generational assets are rare—success hinges on understanding both the property’s history and its long-term promise, and on acting decisively when the right moment arrives.
Want to achieve results like this?
Contact Triton Realty Group to discuss your property goals in Chicago and discover how local expertise and visionary strategy can unlock your next great investment.

