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Enjoy the best of city living in this beautifully maintained three-level townhome on a charming, tree-lined street in the heart of Little Italy. Offering 2 bedrooms, 2 full bathrooms, a functional multi-level layout, attached one-car garage, and multiple outdoor spaces, this home blends comfort, convenience, and the best of urban living. Freshly updated throughout, the home features all-new hardwood floors, new lighting, fresh paint, and freshly carpeted staircases, creating a bright and welcoming feel. The main living level offers an inviting open layout with a spacious kitchen featuring white cabinetry, granite countertops, stainless steel appliances, a new dishwasher, and breakfast bar, flowing seamlessly into the dining and living areas. A dedicated office nook provides the perfect work-from-home space, while the private balcony offers an additional spot to enjoy your morning coffee or unwind. The upper level features two comfortable bedrooms, while the lower-level family room offers flexible living space, a full bathroom, and direct access to the attached garage. Recent improvements include a new furnace in 2024, along with a freshly restained patio and rooftop deck. One of the home's standout features is the private rooftop deck with direct access from inside the unit, offering beautiful skyline views and the perfect setting for entertaining, relaxing, or enjoying Chicago's warmer months. Perfectly positioned just moments from the restaurants, cafes, and shops along Taylor Street, with convenient access to UIC, the Medical District, public transportation, and major expressways. A wonderful opportunity to enjoy the character of Little Italy with the space, privacy, and outdoor living that make townhome living so appealing.

Highlights

  • Residential
  • Townhouse
  • Built in 2000
  • $150/mo HOA
  • 1 Car Garage
  • 7 days on Market

  • Bedrooms
    2
  • Bathrooms
    2
  • Year Built
    2000
  • Stories
    3.0
  • Construction Materials
    Brick
  • Garage Spaces
    1.0
  • Parking Features
    Attached, Garage
  • Interior Features
    Granite Counters
  • Flooring
    Hardwood
  • Cooling
    Central Air
  • Heating
    Forced Air
  • Basement
    None


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Frequently Asked Questions

How do I schedule a tour of 1414 W Fillmore St?

We can make that happen quickly. Click Tour This Home and we'll connect you directly with our vetted local partner to schedule your visit to 1414 W Fillmore St.

They know residentials in the area well and can give you the guidance you need to buy with confidence.

How do I get more information about 1414 W Fillmore St?

Click Ask a Question to talk with our team. You already know it is a 2 bed, 2 bath, listed for $560,000. We can talk through recent upgrades, potential seller motivation, how this townhouse compares to others in Chicago, and can even get you in to see the property quickly.

How much is the monthly mortgage payment for 1414 W Fillmore St?

With a 20% down payment and a 30-year fixed loan at an illustrative 7.25% rate, the ez Mortgage Calculator estimates the monthly payment for 1414 W Fillmore St at around $3,981. This includes estimated property taxes and insurance.

Want to see how this changes with different down payments or interest rates? Jump to the calculator to run the numbers and fine-tune your plan.

How do I get pre-approved to buy 1414 W Fillmore St?

Stand out in a competitive market by getting pre-approved today. Our quick and private pre-approval process helps you understand your true buying power—no credit pull required to explore all of your options.

Or, let us connect you with our preferred local lender in Cook County. They will give you all of your available financing options, based on your specific situation and what is available to you.

Can I negotiate the asking price for 1414 W Fillmore St?

In most cases, yes. Whether 1414 W Fillmore St is priced competitively or not, your best offer depends on your personal situation, the seller's timeline, and recent activity in Chicago's market. Our preferred local partner will help you craft a strategy—factoring in comparable properties that have sold, timing, and deal structure—to make a smart, strong offer. Click here to ask about negotiation opportunities.

How do I make an offer on 1414 W Fillmore St?

We can handle that for you. Our preferred local agent specializes in residentials in Chicago and can guide you through every step of the offer process.

You need an expert who is looking out for your best interests. From market valuation to contingencies and timing, they'll help you present a compelling offer that fits your goals. Click Ask a Question to get started today.

How long has this property been on the market?

1414 W Fillmore St was listed on November 05, 2026, which means it's been on the market for 7 days.

Want to keep tabs on it? Click the ♥ to favorite this home and get notified of price drops or changes.

When was this house built?

This home was built in 2000, making it approximately 26 years old.

What are the property taxes for 1414 W Fillmore St?

The most recent public record shows annual property taxes for 1414 W Fillmore St were approximately $9,527. This may change with reassessment or exemptions. Our local partner can verify current tax amounts and help you estimate future costs based on your situation.

Is there an HOA fee for this property, and what does it cover?

This home has an HOA fee of $150 paid monthly.

Is 1414 W Fillmore St still available for sale?

Yes, this home is still available! Click the ♥ to favorite it so you don't miss any changes—or ask our local expert to schedule a time to see it in person.

Source: ez Home Search, MLS Data

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Listing information provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed by the MLS. Copyright 2026, Midwest Real Estate Data (MRED). All rights reserved.

Last Updated: November 12, 2026 at 07:47AM | Source: Midwest Real Estate Data (MRED) | MLS#: 12802557