Agent profile image in chat bubble
Agent profile image in chat header

IDX Support

sales rep | Brivity IDX

Agent profile image in message

4448 N Tripp Ave , Chicago, IL 60630
$1,099,000
Est. Payment: $5,896.65/mo
5 Bed
6 Bath
0.09 Acres
Status: active | Days on site: 7
Get Pre-Qualified
3804 - 43696
By proceeding and clicking the sign up button, you consent to receive calls and texts (SMS/MMS) including marketing and promotional communications, from IDX Support, its affiliates, and agents or vendors acting on their behalf. These communications may be delivered using an automatic telephone dialing system or by using an artificial or prerecorded voice. Message and data rates may apply. To opt out of text messages, reply STOP. Your consent is not required as a condition of any purchase. By continuing, you also agree to our Terms of Use and Privacy Policy.

House Description

Welcome to this exceptional Greystone vintage 2-unit building with a garden apartment on the lower level - offering 5 bedrooms, 5 full bathrooms, and 1 half bathroom, perfectly blending classic Chicago charm with modern comfort. Featuring beautiful landscaping, a fenced backyard, and thoughtfully designed living spaces, this remarkable property presents an outstanding opportunity for both homeowners and investors. A stunning hardwood staircase welcomes you through the main entrance, providing access to both the first- and second-floor units. Let's begin with the second-floor residence. As you enter, you're greeted by a bright and spacious living room, highlighted by a beautiful English skylight lantern above the foyer and oversized windows that fill the home with abundant natural light. Located just off the living room, the primary suite offers a private retreat with a separate sitting area, generous closet space, direct access to a private balcony, and large windows that create a warm and inviting atmosphere. On the opposite side of the living room, the second bedroom features a walk-in closet and ample living space. The unit includes two full bathrooms-one with a luxurious walk-in steam shower and the other with a relaxing soaking tub. Conveniently located between the bedrooms, the dedicated laundry room adds everyday comfort and functionality. Toward the rear of the home, the open-concept family room and kitchen create the perfect gathering space, centered around a cozy fireplace with both gas and wood-burning options. The kitchen is beautifully appointed with stainless steel appliances, a large center island with breakfast bar seating, pantry storage, and expansive windows that surround the space with exceptional natural light. The first-floor unit mirrors the upper-level layout, offering incredible flexibility for multi-generational living or rental income. It features its own fully equipped kitchen, two full bathrooms, a dedicated laundry room, and an added layer of security with alarm sensors installed on every window. From the rear staircase, you'll find access to the basement studio unit. Before entering the studio, you'll pass a spacious recreation room, utility area, and a separate laundry room dedicated exclusively to the lower-level residence. Inside the studio, you'll find a thoughtfully designed living space featuring a full kitchen with stainless steel appliances, a microwave, air fryer, and range hood. The studio also includes one full bathroom, one half bathroom, and generous closet space, creating a comfortable and functional living arrangement that's perfect for guests, extended family, or rental income. The rear staircase also provides convenient access to the rooftop, the first-floor unit, and the second-floor residence, making movement throughout the building both practical and efficient. Designed with long-term comfort and peace of mind, the property is equipped with multiple tankless water heaters, multiple zoned furnaces, multiple sump pumps, and a comprehensive security system, showcasing the exceptional care and quality invested throughout the home. Step outside to enjoy the beautifully landscaped, fenced backyard featuring a brick paver patio, mature landscaping, and multiple outdoor seating areas-an ideal setting for entertaining family and friends or simply relaxing outdoors. Conveniently located near public transportation, bus routes, restaurants, grocery stores, shopping, and everyday conveniences, this exceptional Greystone offers the perfect combination of timeless Chicago architecture, modern functionality, and outstanding investment potential. Don't miss this rare opportunity to own a versatile, meticulously maintained multi-unit property that seamlessly blends historic character, modern upgrades, and exceptional income potential-all in one of Chicago's most desirable neighborhoods.

Highlights

Listed by Jane Lee , 847-295-0800 RE/MAX Top Performers , 847-295-0800. Midwest Real Estate Data mls logo

Property Type

Multi-Family

Lot/Acreage
0.09

Year Built

1910

County

Cook

Area

CHI - Irving Park

School District

299

Listing ID

12790750

Questions about this listing?

Contact Agent

Interior Features

Bedrooms and Bathrooms
  • ▪ Bedrooms:5
  • ▪ Bathrooms:6
Appliances:Humidifier, Security System,CO Detectors,Sump Pump,Backup Sump Pump;,Multiple Water Heaters
Basement:Finished,Full
Water:Lake Michigan

Exterior Features

Lot Dimensions:25x157x25x156
Garage Capacity:2
Roof:Asphalt
Others:
  • ▪ Additional:Balcony
Sewer:Public Sewer
Parking Features:Yes,Garage Owned,Detached,Garage
Principal Interest
$5,897
Taxes
$1,071

Home Price

$1,099,000

Loan Details

30 yrs
7.08%

Down Payment

20%
$219,800
All calculations are estimates and provided by Blueroof360. Today’s Rates provided by Blueroof360. Information and interactive calculators are made available to you only as self-help tools for your independent use and are not intended to provide investment or tax advice. We cannot and do not guarantee their applicability or accuracy in regards to your individual circumstances. All examples are hypothetical and are for illustrative purposes. We encourage you to seek personalized advice from qualified professionals regarding all personal finance issues.
Monthly Price:
$5,896.65

Principal

Taxes

Principal Taxes HOA Total
Monthly $5,896.65 $1,070.55 $0.00 $6,967.21
Yearly $70,759.84 $12,846.63 $0.00 $83,606.47
Total $2,122,795.07 $385,398.90 $0.00 $2,508,193.97
Lender profile image
Master Chief
Lender
GET PRE-QUALIFIED

Never Miss a Property

Be the first to know when a property hits the market.

Current Listings

Last 30 Days
N/A
Oct 2026

Average Price

All Price Ranges
N/A
Oct 2026

Average Days on Market

All Price Ranges
N/A
Oct 2026
Market insight data is pulled from the same city as the listing being viewed (Chicago, IL).

The schools listed are within a 2-mile radius of the property; however, attendance is not guaranteed. Please contact the local school district to confirm zoning and enrollment options.

Based on information submitted to the MRED as of the date listed below. All data is obtained from various sources and has not been, and will not be, verified by broker or MRED. MRED supplied Open House information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. IDX information is 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. Data is deemed reliable but is not guaranteed by MTP or MRED. The use of the MRED Data may be subject to an end user license agreement prescribed by the Member Participant's applicable MLS if any and as amended from time to time.

Based on information submitted to the MLS GRID as of the date listed below. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. IDX information is provided exclusively for consumers' personal non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, that the data is deemed reliable but is not guaranteed by MLS GRID, and that the use of the MLS GRID Data may be subject to an end user license agreement prescribed by the Member Participant's applicable MLS if any and as amended from time to time. MLS GRID may, at its discretion, require use of other disclaimers as necessary to protect Member Participant, and/or their MLS from liability. Some listings have been excluded from this website.

IDX service by Blueroof 360

Data last updated: 2026-10-27T04:57:04.000Z

© 2026 Midwest Real Estate Data

MLS Logo - Midwest Real Estate Data