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Multi family home for sale at 4448 N Tripp Ave, Chicago, IL 60630 | MLS# 12763441 | Listing updated on 2026-09-25
Photo 1 of Multi family home for sale at 4448 N Tripp Ave, Chicago, IL 60630 | MLS# 12763441 | Listing updated on 2026-09-25
Photo 2 of Multi family home for sale at 4448 N Tripp Ave, Chicago, IL 60630 | MLS# 12763441 | Listing updated on 2026-09-25
Photo 3 of Multi family home for sale at 4448 N Tripp Ave, Chicago, IL 60630 | MLS# 12763441 | Listing updated on 2026-09-25
Photo 4 of Multi family home for sale at 4448 N Tripp Ave, Chicago, IL 60630 | MLS# 12763441 | Listing updated on 2026-09-25
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$1,150,000

Monthly Est:$5,724

  • Beds Icon5 Beds
  • Beds Icon
    6 Baths
  • Beds Icon--sqft

4448 N Tripp Ave, Chicago, IL 60630

$5,724/moEst:

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  • Multi Family

  • Built in 1910

  • $-- HOA

  • 3,920.4 sqft lot

  • --/sqft

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.

  • Houzeo last checked: 45 minutes ago
  • Listing updated: September 25, 2026 at 8:02 am
  • Listing Provided by: Jane Lee | RE/MAX Top Performers (847) 295-0800
  • Source: MRED MLS-IL | MLS#: 12763441 MRED MLS-IL

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Building
4448 N Tripp Ave
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Property Details

  • Status

    Active

  • Type

    Multi Family

  • No. of Stories

    -

  • County

    Cook County

  • City

    Chicago

  • Neighborhood

    Irving Park

  • Year Built

    1910

  • HOA Fees

    -

  • Finished Area

    - sqft

  • Lot Size

    3,920.4 sqft lot

  • Basement Area

    - sqft

  • MLS Name

    MRED MLS

  • MLS Number

    12763441

  • MLS Status

    Active

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Location

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 5

    Bathrooms: 6

Interior

  • Exterior Features

    Balcony

  • Sewer

    Public Sewer

  • Window Features

    Screens

  • Heating

    Natural Gas, Forced Air, Sep Heating Systems 2+, Indv Controls, Zoned

  • Appliances

    Humidifier

Construction

  • Year Built

    Year Built: 1910

  • Home type

    Multi Family

  • Construction Materials

    Stone

  • Roof

    Asphalt

Utilities & Energy

  • Parking Features

    Yes, Garage Owned, Detached, Garage

  • Basement

    Finished, Full

  • Water Source

    Lake Michigan

Other Features

  • Patio And Porch Features

    Patio

  • Community Features

    Curbs, Sidewalks, Street Lights, Street Paved

Price History

DateEventPrice

09/18/2026

Source: mls_logoMRED MLS-IL #MRD12752105

Listing Removed

$1,150,000

$0/sqft

09/18/2026

Source: mls_logoMRED MLS-IL #MRD12763441

Listed for Sale

$1,150,000

$0/sqft

09/16/2026

Source: mls_logoMRED MLS-IL #MRD12752105

Price Decreased

$1,150,000 -4.09%

$0/sqft

09/04/2026

Source: mls_logoMRED MLS-IL #MRD12714372

Listing Removed

$1,199,000

$0/sqft

09/04/2026

Source: mls_logoMRED MLS-IL #MRD12752105

Listed for Sale

$1,199,000

$0/sqft

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Irving Park Ranks #56 in Chicago, IL

Homes for sale
74

Homes

Rental prices
$1,216

Rental Prices

Median Home Price
$480K

Median Home Price

Irving Park, Chicago, IL neighborhood guide

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This representation is based in whole or in part on data supplied by Midwest Real Estate Data, LLC through Oct 09, 2026, 12:00PM. Midwest Real Estate Data, LLC does not guarantee nor is it in any way responsible for its accuracy. Data maintained by Midwest Real Estate Data LLC may not reflect all real estate activity in the market.

Based on information submitted to the MLS GRID as of Oct 09, 2026, 12:00PM. All data is obtained from various sources and has not been, and will not be, 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. This website may not include listings or property addresses of sellers who have directed their listing brokers to withhold their listing or their property address from display on the Internet. Some IDX listings have been excluded from this website. Information is provided exclusively for consumers’ personal non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID, MRED or Houzeo. The use of the MLS GRID Data may be subject to an end user license agreement. Properties displayed may be listed or sold by various participants in the MLS,

Listings courtesy of MRED as distributed by MLS GRID. ©2026 Midwest Real Estate Data LLC. All Rights Reserved

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