Fully Renovated 8-Unit Multifamily Gem Sells Off-Market in Uptown Chicago
Sale at a Glance
On November 16, 2023, an impeccably renovated 8-unit center-entry building at 4927-4929 N. Winthrop Ave. was sold for $2,425,000 in an off-market deal that underscores the enduring allure of classic Chicago multifamily assets. Represented by Matthew Fritzshall (President & Founder) and Harrison Cohen (SVP & Principal) of Triton Realty Group LLC, both seller and buyer found synergy in a transaction shaped by trust, timing, and a clear vision of long-term value. Every unit in this fully occupied property offers generous three-bedroom, two-bath layouts, just steps from Andersonville, the Argyle entertainment corridor, and multiple transportation links. This sale is a beacon for investors seeking stability, future upside, and prime location in one of Chicago’s most dynamic neighborhoods.
Sale Details
This transaction demonstrates the power of relationships and nuanced market expertise in unlocking off-market opportunities.
Sale Price & Date: Closed for $2,425,000 on November 16, 2023
Brokerage: Triton Realty Group LLC
Lead Brokers: Matthew Fritzshall (President & Founder), Harrison Cohen (SVP & Principal)
Unit Count: 8 spacious residential flats, each 3 bedrooms and 2 bathrooms
Parking: 8 dedicated surface spaces, a premium for residents and added income stream
Occupancy: 100% leased at closing, reflecting strong demand and management
Buyer Profile: Out-of-state investor utilizing a 1031 exchange for portfolio growth and tax deferral
Property Highlights
This building blends the historic charm of Uptown with contemporary living standards and rock-solid fundamentals.
Extensive Renovation: Underwent a full, condo-level renovation eight years ago, ensuring modern finishes, improved systems, and long-term durability
Unit Configuration: All units are oversized 3BR/2BA layouts, rare in the submarket and ideal for families or roommates
Garden Units: Two lower-level garden units are bright, airy, and only a few steps below grade, featuring high ceilings and full-size windows—maximizing rentable space and desirability
Prime Location: Steps away from the Argyle Shared Streetscape, vibrant dining, retail, and the CTA Red Line, connecting residents to the heart of Chicago
Parking Advantage: Eight private surface spaces elevate the building’s profile, providing convenience in a dense urban setting
Condo Conversion Ready: The property’s build quality and floor plans make it a natural candidate for future condo conversion, offering an owner multiple exit strategies
Key Investment Features
The asset’s unique characteristics create value across multiple dimensions, making it a magnet for sophisticated investors.
Turnkey Investment: No deferred maintenance, fully stabilized, and producing strong, predictable cash flow from day one
Desirable Tenant Mix: Large, modern units attract stable, higher-income tenants and reduce turnover risk
Multiple Income Streams: Rental income is enhanced by the premium parking and appealing amenities
Upside Potential: While currently stabilized, the building’s size, renovation quality, and location create opportunities for future rent growth, condo conversion, or strategic repositioning
Secure Location: Uptown continues to benefit from infrastructure investment, retail revitalization, and new development, supporting long-term appreciation
Market Strategy and Positioning
The success of this transaction was rooted in deep market knowledge and the ability to forge direct, trust-based relationships. The property was never brought to the open market; instead, Triton Realty Group leveraged its network to match a seller eager to recapture equity with a buyer seeking a reliable, high-upside asset for a 1031 exchange. By focusing on the property’s full renovation, large floor plans, and unbeatable location, the brokers articulated a vision that resonated with sophisticated buyers. The off-market approach ensured discretion, speed, and optimal terms for both parties, and demonstrated how curated brokerage strategies can unlock hidden value in Chicago’s highly competitive multifamily market.
Frequently Asked Questions (FAQs)
This sale highlights what’s possible for investors and owners in Chicago’s evolving North Side.
What makes 4927-4929 N. Winthrop Ave. unique among Uptown multifamily properties?
The building stands apart thanks to its full-scale, condo-quality renovation, all-3BR/2BA layouts, and a coveted location steps from major amenities and transportation. The inclusion of eight surface parking spaces further distinguishes it from most comparable assets.
How did the off-market process benefit the buyer and seller?
Direct negotiation allowed for a seamless transaction tailored to both parties’ needs. The seller recaptured equity efficiently, while the buyer secured a rare, stabilized asset without the competition and uncertainty of a public listing.
Why are three-bedroom units significant in this location?
Larger units attract a broader tenant base, including families and professionals seeking extra space. This reduces vacancy risk and enhances rent potential, especially in neighborhoods like Uptown with diverse housing demand.
What future opportunities are possible for this building?
Given its condo-level renovations and large floor plans, the property is ideally positioned for a future condo conversion or continued rental growth as demand in Uptown intensifies.
How does the parking amenity impact value and tenant appeal?
Parking is a premium in Chicago’s dense North Side. Dedicated surface spaces not only command higher rents but also make the property more attractive to a wider pool of tenants, including those with families or multiple vehicles.
Want to achieve results like this?
Contact Triton Realty Group LLC to discuss your property goals in Chicago’s vibrant multifamily market. Reach out to Matthew Fritzshall and Harrison Cohen at Triton Realty Group for a confidential consultation and discover how strategic brokerage can unlock your asset’s full potential.
