4448 N Tripp Avenue Chicago, IL $ 1,399,000
4448 N Tripp Avenue
$ 1,399,000
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4448 N Tripp Avenue

Chicago, IL, 60630
$ 1,399,000
Bedrooms5 Baths6.1 Sq 3,927

Monthly Estimate*

$ 8,833

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Multi-Family Home for sale in Chicago, IL

for $1,399,000 with 5 bedrooms and 6 full baths, 1 half bath. This 3,927 square foot home was built in 1910 on a lot size of 0.09.

Welcome to this exceptional Greystone vintage 3-unit building 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.

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Multi-Family Active

Price

$ 1,399,000

Bedrooms

5

Full Bath

6

Half Bath

1

Property Type

Multi-Family

Taxes

$ 12,846

Style

Lot Size

0.09

Year Built

1910

Town/City

Chicago

County/Region

Cook

MLS | Web ID

12688751

Features
General
Sewer Public Sewer
Heating Natural Gas Forced Air Sep Heating Systems - 2+ Indv Controls Zoned
Possession Closing
Roof Asphalt
Appliances Humidifier
Garage Spaces 2
Construction Materials Stone
Year Built 1910
Township Jefferson
Tax Year 2024
Ownership Fee Simple
Community Features Curbs Sidewalks Street Lights Street Paved
County Cook
New Construction N
Property Type Residential Income Two to Four Units
Total Rooms 11
Status New
Directions I90/ W MONTROSE AVE E ON W MONTROSE AVE L ON TRIPP AVE
High School Schurz High School
City Chicago
High School District 299
MLS Area CHI - Irving Park
Elementary School Belding Elementary School
Tax Annual Amount 12846.63
Middle/Junior High School Belding Elementary School
Standard Status Active
Middle/Junior School District 299
Elementary School District 299
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Interior
Basement Finished Full
Total Bedrooms 5
Total Baths 6
Bedrooms Possible 5
Bathroom Separate Shower Steam Shower Soaking Tub
Full Baths Building 5
Half Baths Building 1
Total Number of Units 3
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Exterior
Exterior Amenities Balcony
Parking Features Yes Garage Owned Detached Garage
Water Source Lake Michigan
Total Parking 2
Lot Dimensions 25x157x25x156
Lot Size Acres 0.09
Waterfront Y/N N
Other Equipment Security System CO Detectors Sump Pump Backup Sump Pump; Multiple Water Heaters
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* Excluded Features
List By
Re/Max Top Performers

Broker

janeleeteam1@gmail.com

Email

Affordability Calculator

$9,904
Per Month
89%
11%
0%
Monthly Principal & Interest
$8,833
Monthly Property Taxes
$1,071
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
908886 Elementary School
908886 Middle School
Schurz High School High School
Pricing History
DatePricePrice ChangeDescription
7/2/2026$1,399,000 Listed Price

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4448 N Tripp Avenue, Chicago, IL, 60630 is a Multi-Family Home for sale at $1,399,000 with 3,927 sqft and a lot size of 0.09. 4448 N Tripp Avenue has 5 bedrooms, 6.1 baths, and was built in 1910. The property's zip code is 60630 which is in Chicago, IL