Legacy Andersonville Six-Unit Walkup Sells Off-Market for $1.5M—A Story of Family, Precision, and Neighborhood Excellence
Sale at a Glance
Nestled in the heart of Andersonville, 5334 N. Glenwood Ave. | 1400-06 W. Summerdale Ave. stands as a testament to both generational stewardship and forward-looking investment. In April 2022, the property transitioned from a family who had lovingly owned and managed it for over five decades to a seasoned local investor eager to expand within one of Chicago’s most coveted neighborhoods. Orchestrated by Triton Realty Group in a bespoke, off-market transaction, this six-unit building achieved a sale price of $1.5 million at full occupancy—underscoring Andersonville’s enduring demand for quality multifamily assets.
Sale Details
This transaction brought together a deeply invested seller and an ambitious buyer through a confidential, expertly managed process.
Sale Price: $1,500,000
Closing Date: April 15, 2022
Listing Broker: Triton Realty Group, led by SVP & Principal Harrison Cohen and President & Founder Matthew Fritzshall
Buyer: Longstanding client actively seeking to scale their footprint in Andersonville
Units: 6 spacious two-bedroom apartments
Occupancy at Sale: 100%
Ownership Legacy: Family-held for over 50 years, with hands-on management by the son for the last 12 years following his father’s passing
Property Highlights
This classic Chicago brick walkup distinguishes itself with its blend of historical character, large living spaces, and thoughtful modernization.
Expansive Living: Each residence offers a generous 5.5-room, 2-bedroom, 1-bath layout—rare for the North Side rental market
Infrastructure Upgrades: 400AMP electrical service and modern circuit breaker panels (2013) ensure reliability and safety
Recent Capital Improvements: Newly rebuilt porches (2022) and an 80-gallon water heater (2020) minimize deferred maintenance
Prime Andersonville Location: Steps from Clark Street, public transit, and the neighborhood’s celebrated dining and retail scene
Key Investment Features
The property’s compelling fundamentals and future upside stood out to strategic investors.
Stabilized Asset: Fully leased at closing, with a track record of strong occupancy
Operational Ease: Recent upgrades translate into reduced capital expenditures and ease of ownership
Unmatched Neighborhood Appeal: Andersonville’s reputation as a vibrant, inclusive, and nationally recognized community elevates both rentability and appreciation prospects
Value-Add Potential: Spacious vintage apartments allow for future interior enhancements to boost revenue
Market Strategy and Positioning
Triton Realty Group leveraged its deep ties and nuanced understanding of Andersonville to quietly connect the right buyer and seller. Recognizing the emotional weight of transitioning a multi-generational asset, the team pursued a “sniper rifle” approach—eschewing public marketing in favor of highly targeted outreach to select, qualified investors. This bespoke strategy honored the seller’s privacy, fostered trust, and delivered a seamless experience while maximizing value. The result: a swift, confidential closing that respected the building’s legacy and set the stage for its next chapter.
Client Testimonial
“Working with Triton was a breath of fresh air. Their knowledge of Andersonville’s unique market and their sensitivity to our goals made all the difference. They didn’t just find us a building—they secured a true piece of the neighborhood’s history. We’re excited to continue growing here.”— Mitchell Zamost, AlJack Investments
Frequently Asked Questions (FAQs)
This off-market Andersonville transaction shines a light on what’s possible with local expertise and strategic matchmaking.
What distinguished this property from others in Andersonville?The rare combination of long-term family ownership, meticulous care, and turnkey condition made it a standout asset in a supply-constrained neighborhood.
Why was an off-market approach chosen for this sale?The seller prioritized discretion and a tailored process, which Triton Realty Group delivered through strategic, relationship-driven outreach.
What are the next steps for the new owner?With recent major upgrades and stable tenancy, the buyer can focus on incremental interior improvements and continued stewardship.
How does Andersonville’s market climate influence investment decisions?Andersonville’s national recognition for culture, safety, and community engagement fuels strong rental demand and long-term appreciation.
What role did Triton Realty Group play in navigating this sale?Their hyper-local expertise, trust-based relationships, and bespoke marketing approach enabled an outcome that benefited both buyer and seller.
Want to achieve results like this?
Contact Triton Realty Group—SVP & Principal Harrison Cohen and President & Founder Matthew Fritzshall—to explore your investment goals in Andersonville and across Chicago.
