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$1,150,000
Monthly Est:$5,724
5 Beds
- 6 Baths
--sqft
4448 N Tripp Ave, Chicago, IL 60630
$1,150,000
$5,724/moEst:
Get Pre-Approved
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

Part of
Property Details
Status
Active
Type
Multi Family
No. of Stories
-
County
City
Neighborhood
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
Open House

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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
| Date | Event | Price |
|---|---|---|
09/18/2026 Source: | Listing Removed | $1,150,000 $0/sqft |
09/18/2026 Source: | Listed for Sale | $1,150,000 $0/sqft |
09/16/2026 Source: | Price Decreased | $1,150,000 -4.09% $0/sqft |
09/04/2026 Source: | Listing Removed | $1,199,000 $0/sqft |
09/04/2026 Source: | Listed for Sale | $1,199,000 $0/sqft |
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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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