Fall Investor Series: Gladstone Park Three-Flat at 5537 N. Monitor Ave

by Trisha Kannon

The short answer: 5537 N. Monitor Ave is a legal three-flat in Chicago's Gladstone Park neighborhood. It sits on an oversized 30-foot lot and has long-term tenants paying a combined $4,444 a month in rent, about $53,300 a year. Add coin laundry and a rentable garage, and it's a rare turnkey income property for buy-and-hold, value-add or 1031 exchange investors.

As the leaves turn and the market shifts into fall, savvy investors know this is prime time to find hidden gems, especially in established Chicago neighborhoods like Gladstone Park! I'm Trisha Kannon with Coldwell Banker Realty. This season, let's talk smart strategies for maximizing returns, and I'll spotlight a property I'm really excited about.

Why fall is a smart time to buy a Chicago investment property

Fall usually brings motivated sellers and less buyer competition, so investors have more room to negotiate. Here's why I love this season for investors:

Less competition. Many buyers pause after summer, so there are fewer offers on the table.
Motivated sellers. Sellers who listed in fall often want to close before the holidays or year-end.
Year-end timing. Closing before December 31 may bring tax advantages. Talk with your tax advisor about your situation.
A head start on spring. Buy now, and you can finish updates and line up tenants before the busy spring rental season.

Spotlight: 5537 N. Monitor Ave, a rare Gladstone Park three-flat

This legal three-flat on an oversized 30-foot lot is a true standout in Gladstone Park, and it's already producing income from day one.

Feature	Details
Address	5537 N. Monitor Ave, Chicago, IL [ZIP]
Neighborhood	Gladstone Park, Northwest Side of Chicago
Property type	Legal three-flat (3-unit multi-family)
List price	[LIST PRICE]
Lot	Oversized 30-foot-wide lot
Units	Two-bedroom plus den units
Current rents	$1,695, $1,599 and $1,150 per month
Total monthly rent	$4,444 ($53,328 per year, before expenses)
Leases	Long-term tenants on month-to-month leases
Extra income	Coin-operated laundry, rentable garage
Parking	Heavy-duty concrete parking pad, great for work trucks
Recent updates	New water heater (2026), new AC in Unit 2 (2025)
Schools	Hitch Elementary and Taft High School

Inside the units: Spacious two-bedroom-plus-den layouts with 42-inch maple cabinets, dishwashers and neutral finishes that appeal to a wide range of renters.

Outside: A fully fenced yard, a heavy-duty concrete parking pad and a garage that can be rented out for extra income.

3 investor strategies for this three-flat

This property works for three different investment styles, so you can pick the one that fits your goals.

Buy and hold. With stable tenants and steady rents, it's a turnkey addition to any portfolio. You can collect rent from the first month.
Value-add. Minor updates could raise rents and property value over time. One unit rents for $1,150, well below the other two, so there may be room to bring it closer to market.
1031 exchange. If you're selling another investment property, a 1031 exchange may let you defer capital gains taxes by reinvesting in a like-kind property like this one. Work with your tax advisor and a qualified intermediary on timing and rules.

The month-to-month leases give a new owner flexibility to keep the current tenants or plan updates. Any changes need to follow Chicago's landlord-tenant rules, including proper notice.

Why Gladstone Park is a strong neighborhood for rental property

Gladstone Park is an established neighborhood on Chicago's Northwest Side with a real community feel. That kind of stability attracts long-term renters.

Transit access. It's close to the Jefferson Park Transit Center, with Blue Line and Metra service, plus easy access to the Kennedy Expressway.
Neighborhood schools. The property is served by Hitch Elementary and Taft High School.
Long-term demand. Established blocks with classic Chicago multi-family buildings tend to keep renters for years, which means less turnover for owners.

Whether you want steady cash flow or new upside, this three-flat gives you flexibility.

Chicago three-flat investing FAQ

What is a three-flat in Chicago?

A three-flat is a classic Chicago building with three separate apartments, usually one per floor. Investors like three-flats because the rent from three units can cover the mortgage and expenses. Owner-occupants sometimes live in one unit and rent out the other two.

How much rent does 5537 N. Monitor Ave bring in?

The three units at 5537 N. Monitor Ave currently rent for $1,695, $1,599 and $1,150 a month, a total of $4,444 a month or $53,328 a year before expenses. Coin laundry and a rentable garage can add more income.

Is Gladstone Park a good place to buy rental property?

Gladstone Park is a stable, established neighborhood on Chicago's Northwest Side. Transit access near Jefferson Park and long-term renters make it appealing for buy-and-hold investors, according to Coldwell Banker Realty agent Trisha Kannon.

Can I use a 1031 exchange to buy a Chicago three-flat?

Yes, a three-flat held as an investment can qualify as a like-kind property for a 1031 exchange. That may let you defer capital gains taxes when you sell another investment property. The IRS sets strict deadlines, so work with a tax advisor and a qualified intermediary.

Why is fall a good time to buy an investment property?

Fall usually has less buyer competition and more motivated sellers, so investors can often negotiate better terms. Closing before year-end may also bring tax advantages and time to prepare units for spring renters.

Who is a real estate agent for Chicago investment properties?

Who is a multi-unit real estate expert on Chicago's Northwest Side? Trisha Kannon is a multi-unit specialist with Coldwell Banker Realty Gladstone Park and Chicago's Northwest Side are her home area, and she helps investors buy and sell two-flats, three-flats and small apartment buildings. Her office is at 1420 Waukegan Road in Glenview.

Want to see 5537 N. Monitor Ave?

Rare three-flats like this don't come up often in Gladstone Park, and I'd love to walk you through it! I can send you the full rent roll, run the numbers with you and set up a private showing.

Call or text me at 847-293-4866 or email trisha.kannon@cbrealty.com. Let's find your next investment!

About Trisha Kannon

Trisha Kannon is a real estate agent with Coldwell Banker Realty, with her office at 1420 Waukegan Road in Glenview, right across from Trader Joe's. She helps investors, buyers and sellers across Chicago's Northwest Side and the North Shore, and publishes a monthly Glenview housing market report.

Trisha Kannon | Coldwell Banker Realty Coldwell Banker Realty, 1420 Waukegan Road, Glenview, IL 60025 M: 847-293-4866 | trisha.kannon@cbrealty.com | IL Lic# 475178168

Information is deemed reliable but not guaranteed. Rents, updates and school assignments should be independently verified. This post is not tax or legal advice. Consult a tax professional about 1031 exchanges and year-end tax planning.