What $1.595M Buys in Lakeview Chicago: 2-Flat + Garden Unit Near Southport Corridor
1244 W Oakdale Ave · Chicago, IL 60657 · Lakeview / Southport Corridor
Includes an additional non-conforming garden unit. Buyers should independently verify permitted use, zoning, unit legality, measurements and future conversion options. Pricing and availability are subject to change.
At 1244 W Oakdale Ave, Chicago, IL 60657, buyers get a classic Lakeview 2-flat with an additional non-conforming garden unit, approximately 2,502 square feet of living space, 8 total bedrooms, 4 bathrooms, a 2-car detached garage, and a rooftop deck.
The property sits on a tree-lined residential street near the Southport Corridor, creating an opportunity for investors or owner-occupants looking for a multi-family property in one of Chicago's most established North Side neighborhoods.
A Classic 2-Flat With Additional Garden-Level Space
The building combines traditional Chicago multi-unit character with updates designed for modern living.
Across the property, buyers will find hardwood floors, high ceilings, generous room sizes, and abundant natural light.
The kitchens in Units 1 and 2 feature custom wood cabinetry, granite countertops, backsplashes, and ample storage, while spacious living and dining areas give each residence room to function comfortably beyond the bedrooms.
The additional garden unit is described in the current listing as non-conforming, an important distinction buyers should understand when evaluating occupancy, financing, rental use, and future plans for the property.
8 Bedrooms, 4 Baths and Flexible Future Use
Altogether, the property offers 8 bedrooms and 4 bathrooms across its residential spaces.
The second-floor residence also presents an additional value-add opportunity. The listing notes that it may be possible to convert the unit into a duplex-up, with plumbing already in place.
Any future conversion would require buyers to independently verify building plans, permits, zoning, code requirements, and feasibility before moving forward.
For an owner-occupant, the property's multiple living spaces may create flexibility to occupy part of the building while generating rental income from the remaining units. Investors may instead evaluate the property around lease structure, market rents, operating expenses, renovation needs, and longer-term appreciation potential.
Rooftop Deck, 2-Car Garage and Private Sauna
The property includes several features that are less common in vintage Chicago multi-family buildings.
A 2-car detached garage adds dedicated parking, while the rooftop deck creates outdoor space above the building.
The ground-floor common area also includes a full bathroom, private sauna, and laundry, giving the building additional shared functionality beyond the individual residences.
Units 1 and 2 have central heat and air conditioning, while the garden residence has central heat.
Why Southport Corridor Matters
Location is a major part of the value proposition.
The property sits near the Southport Corridor, one of Lakeview's most active neighborhood retail and dining districts, with restaurants, coffee shops, boutiques, fitness businesses, groceries, and entertainment within the surrounding area.
Option Premier recently covered the continued investment happening along the corridor in New Southport Corridor Development Brings Retail and Residences to Lake View.
That project adds another example of how Southport continues to attract new residential and commercial investment while retaining its walkable neighborhood character.
Lakeview Access to Transit, Wrigley Field and the Lakefront
The broader Lakeview location also keeps residents close to Wrigley Field, parks, Lake Michigan, and several CTA rail options.
The listing highlights access to the Brown, Purple, and Red Lines, giving residents multiple ways to reach Downtown Chicago and surrounding neighborhoods.
Buyers unfamiliar with the area can explore our Lakeview neighborhood guide for more on local housing, transportation, restaurants, entertainment, and lifestyle.
For investors specifically comparing multi-unit properties in the neighborhood, our recent Lakeview Multi-Family Investment Property Just Closed also provides another example of current investment activity in the area.
Who Could This Lakeview Property Fit?
A property like 1244 W Oakdale Ave can appeal to several different types of buyers.
An investor may focus on the building's multiple income-producing spaces, garage parking, location, condition, and future upside.
An owner-occupant may instead value the ability to live in part of the property while potentially using rental income from the other spaces to offset ownership costs.
Either strategy requires a careful review of leases, current rents, operating expenses, taxes, insurance, property condition, financing, and the legal status of the non-conforming garden unit.
Interested in This Lakeview 2-Flat?
At $1,595,000, 1244 W Oakdale Ave offers a combination of approximately 2,502 square feet, 8 bedrooms, 4 bathrooms, a 2-car garage, rooftop deck, private sauna, and future layout potential near the Southport Corridor.
Contact Serena Phillips-Dunn of The Cory Tanzer Group at Option Premier to schedule a private showing, request additional property details, or compare this opportunity with other Lakeview multi-family properties for sale.
Lakeview & Chicago Multi-Family Real Estate
Meet Serena Phillips-Dunn, Your Local Lakeview Real Estate Expert
COO & Team Lead, The Cory Tanzer Group at Option Premier
Serena Phillips-Dunn helps buyers, sellers, and property owners navigate Lakeview and the broader Chicago real estate market. With a background in marketing, an M.A. in Journalism, and previous experience as a CBS field producer, Serena brings strong communication, strategic thinking, and negotiation experience to residential and multi-family transactions throughout Chicago.
