Heart of Chicago Real Estate

Heart of Chicago Real Estate

The Heart of Chicago neighborhood is a vibrant and sought-after area located in the heart of the city of Chicago, Illinois. Situated in Cook County, this neighborhood offers residents a perfect blend of urban living and community charm.

Known for its rich history and diverse culture, Heart of Chicago is a melting pot of different ethnicities, making it a truly unique place to live. The neighborhood is home to a variety of architectural styles, from classic Victorian houses to modern condominiums, providing residents with a wide range of housing options.

In terms of amenities, Heart of Chicago has everything you need within reach. The area boasts a plethora of restaurants, cafes, and shops, offering a diverse culinary scene and an array of shopping opportunities. Residents can also enjoy nearby parks and green spaces, perfect for outdoor activities and relaxation.

What sets Heart of Chicago apart is its convenient location. With easy access to major transportation routes and public transportation options, residents can easily navigate the city and explore all that Chicago has to offer. From world-class museums and theaters to vibrant nightlife and sporting events, the city is at your fingertips.

If you're looking for a neighborhood that combines the best of urban living with a strong sense of community, Heart of Chicago is the place for you. With its rich history, diverse culture, and convenient location, this neighborhood offers an exceptional living experience in the bustling city of Chicago.

Newest Listings in Heart of Chicago

$1,549,000
7 Beds ⋅ 7 Baths ⋅ 12762020 MLS ⋅ NEW Status
Newer Construction Passive Home 3 Unit building right on Harrison Park- Full Masonry Perfect Wall, All Electric energy-efficient and intelligently engineered for optimal living conditions. Three Bedroom/2.1 Bath Duplex, 2nd floor 2 bed/2 bath & Penthouse 2 bed/2 bath with interior stair to penthouse room and full finished rooftop deck. Excellent views of Harrison Park, the City and abundant natural light. Hardwood floors, Modern Kitchens designed for entertaining with Gray shaker cabinets with quartz countertops, island, full backsplash, and stainless-steel appliances. All bedrooms generously sized to accommodate king sized beds and the bathrooms are finished in Carrera porcelains and brushed nickel. Thoughtful storage and walk-in closets throughout. Rear deck system and washer/dryer in each unit. 3 car Outdoor secured parking. Amazing location, very short walk to the Pink Line and 18th Street with all its vibrancy; Thalia Hall, Canton Regio, Brew Brew PLUS Harrison Park with tennis courts, full gym, indoor swimming pool soccer pitch and all Pilsen has to offer! Builder built for himself and spared no expense- top floor will be vacant at close, perfect for owner-occupant! Grss Annual Income $124,740. NOI $96,555. 6.2 Cap Rate

1815 W 19Th Street, Chicago
$575,000
4 Beds ⋅ 2 Baths ⋅ 12761372 MLS ⋅ NEW Status
One Of the Kind opportunity to own a Huge Brick Single family in Pilsen Walking Distance to cta Transportation & L-Train Station,,Walk to Little Italy Restaurants, Minutes To Hospitals District and Downtown Chicago. Main Level offers 3 Bedrooms, Living Room/Formal Dinning Room ,Big Kitchen Full Finished Attic and Finished Basement with a Full bath & 8Ft High Ceilings with front rear entrance ,, a Mechanics Dream 3 Car Brick Garage. must recent Updates Roof,Furnace,Windows.. Great Location. Call Today

2136 W 23Rd Street, Chicago
$349,900
5 Beds ⋅ 3 Baths ⋅ 12700584 MLS ⋅ NEW Status
Welcome to 2041 W 22nd Pl in Chicago, IL 60608. This property contains three units across two buildings. The primary building contains two units. There is a separate coach house behind the primary building that makes up the third unit. Whether you are looking for a starter home, an investment opportunity, or a property to renovate, this home offers a solid place to begin.

2041 W 22Nd Place, Chicago
$350,000
2 Beds ⋅ 2 Baths ⋅ 12758786 MLS ⋅ NEW Status
Welcome home to this spacious and thoughtfully updated 2-bedroom, 2-bath duplex in an intimate all-brick, 5-unit building tucked away on a quiet, tree-lined cul-de-sac directly across from Harrison Park. Just off the vibrant 18th Street corridor, this home offers an ideal combination of neighborhood convenience and unexpected privacy, with the community garden next door and the 18th Street Pink Line, Thalia Hall, restaurants, coffee shops, parks, and everything Pilsen has to offer just blocks away. The bright, south-facing main level features an open-concept layout with hardwood floors and plenty of room for both living and dining. The kitchen has been refreshed with painted cabinetry, granite countertops, stainless steel appliances, a tile backsplash, and an open pantry converted from the former coat closet for added everyday storage. Nearly every light fixture has been upgraded with warm, modern selections, and most of the home has been freshly painted. A full stone bath with glass-enclosed shower and full-size side-by-side in-unit laundry complete the main level. Downstairs, the private bedroom level features two impressively sized bedrooms, both with room for king-size beds, including a spacious primary with a walk-in closet. The bedrooms share an updated stone Jack-and-Jill bath with a jetted tub, while newer carpet adds comfort throughout the lower level. Additional improvements include a new front screen door, updated hardware and vents, plus significant recent building improvements including a new roof, flashing, and skylights in 2024 and rear staircase repairs, replacement work, and exterior painting completed in August 2026. Unused chimneys were also removed in August 2026. Direct rear stairwell access provides an additional entry and a small outdoor area just beyond the lower-level entrance. Low assessments and dedicated exterior parking included complete this move-in-ready Pilsen home.

1745 W 18Th Place Unit #1R, Chicago
$779,000
7 Beds ⋅ 3 Baths ⋅ 12755104 MLS ⋅ ACTIVE Status
Prime Pilsen Multi-Unit Opportunity! This large and well positioned legal 3 unit property offers an excellent opportunity to own an income producing asset in the heart of Chicago's vibrant Pilsen neighborhood. Featuring a total of 7 bedrooms and 3 bathrooms, the property offers spacious layouts and excellent rental potential across all three units. Currently fully rented and generating $5,300 in monthly rental income, this property is an ideal opportunity for an investor looking to add a solid multi-unit asset to their portfolio or an owner occupant seeking the benefits of rental income. A convenient 2-3 car parking pad provides valuable off street parking, an attractive feature for both owners and tenants. Located directly across from Cooper Elementary School and close to Pilsen's renowned restaurants, cafes, shops, parks, public transportation and everyday neighborhood amenities. With its established rental income, generous bedroom count, parking and desirable location, 1643 W 19th St is an excellent opportunity to own and invest in one of Chicago's most dynamic neighborhoods.

1643 W 19Th Street, Chicago
$559,999
4 Beds ⋅ 2 Baths ⋅ 12740089 MLS ⋅ ACTIVE Status
Beautiful 4bedroom 2bath home in the heart of Chicago's vibrant Pilsen neighborhood, combining classic Chicago character with modern finishes throughout. Step inside to a bright open concept floor plan featuring recessed lighting, new flooring, a spacious living and dining area ideal for everyday living and entertaining. The beautifully designed kitchen features white shaker cabinetry, quartz countertops, stainless steel appliances, and a large center island. Both full bathrooms have been completely updated with modern vanities, tile, and contemporary finishes. The fully finished lower level provides an impressive amount of additional living and entertainment space, complete with a full bathroom, laundry room and a unique spiral staircase connecting the levels. A two car garage provides the added convenience of off street parking. Convenient access to I-55, CTA Pink line, near restaurants, shops, parks and everything the city has to offer. A move in ready home with space, style and location you've been looking for!

2042 W Coulter Street, Chicago
$2,300,000
12732371 MLS ⋅ ACTIVE Status
12-unit multi-family investment opportunity in Chicago's historic Pilsen neighborhood with significant mark-to-market upside! Offered as a portfolio listing combining two adjacent properties (1759 W 21st St & 1801 W 21st St). Total unit breakdown includes two 1BR/1BA units, eight 2BR/1BA units, one 3BR/1BA unit, and a spacious detached rear Coach House (3BR/1BA). High-demand unit mix with strong rental upside, central heat, shared laundry facilities, LVP/hardwood flooring, and modern finishes throughout. Located just blocks from 18th Street dining and a short walk to the Damen Pink Line station. Buy together at $2.3M for an efficient, high-yield Pilsen portfolio asset.

1759 W 21St Street, Chicago
$1,560,000
12730594 MLS ⋅ ACTIVE Status
Exceptional Turnkey 5-Unit Asset in Prime Pilsen with Strong 7.15% Cap Rate & Significant Immediate Upside. Originally reconfigured as an owner-occupied building. Highly lucrative, fully permitted 5-unit commercial residential building situated on a prominent corner lot in Pilsen. Extensively gut-rehabbed to the studs between 2013-2023 with all-new building systems, modern layouts, and premium finishes. Operating at a strong 7.15% current Cap Rate with a projected 1.42 Debt Coverage Ratio (DCR), this asset offers rare immediate bankability and day-one cash flow. UNMATCHED VALUE-ADD OPPORTUNITY: The 1st-floor 1,500 sq. ft. 1BR/1BA loft tenant is vacating, creating an immediate, frictionless opportunity to capture a massive market rent increase or split the oversized floor plan to maximize total yield. Both 1701 W 21st St and 2102 S Paulina St addresses included in sale on single PIN. PREMIUM MECHANICALS & INFRASTRUCTURE: Fully updated water service replaced with copper directly to the city main. Low expenses: Tenants responsible for utilities with separately metered gas and electric. Individual furnaces, central AC, and separate tank/tankless water heaters for every unit. Attached 2-car garage off the alley providing additional premium rental income. Full unfinished basement housing utilities with storage spaces for tenants. HIGH RENTER RETENTION: Well-appointed apartments feature stone/quartz countertops, stainless steel appliances, premium hardwood or engineered flooring, masterfully tiled baths, and convenient in-unit washers and dryers. Superb location with immediate access to Pilsen public transit. Currently self-managed with zero historic vacancy. Clean rent roll, P&L, and T12 commercial underwriting documents available upon request.

1701 W 21St Street, Chicago
$619,000
7 Beds ⋅ 4 Baths ⋅ 12729584 MLS ⋅ ACTIVE Status
Rare 4-Unit in the Heart of Pilsen! Exceptional investment opportunity on an approximately 25' x 125' corner lot (per survey) with RT-4 zoning (buyer to verify). Rare opportunity to acquire a legal 3-unit PLUS a separate coach house in one of Chicago's most sought-after investment neighborhoods. Coach house with front door direct access to Wood Street, allowing it to function much like a standalone single-family home. The front building offers a spacious first-floor duplex-down with soaring ceilings and finished lower level, a rear first-floor 2-bedroom with excellent duplex potential, and a bright, sun-filled second-floor 2-bedroom. The coach house features its own private entrance, lofted ceilings, a 2-bedroom/1-bath layout, and a full unfinished basement offering exceptional storage and future expansion potential. Substantially renovated in 2003, the property features separate electric service and HVAC for all four units. Additional improvements include a front building roof replacement (approximately six years ago) and a new furnace and central air system in the coach house (2025). Offered AS-IS, the property is ready for thoughtful updating and presents an outstanding value-add opportunity. Lovely long-term tenants provide stable in-place income while offering significant upside through future renovations, lease optimization, and rent growth. Current Gross Income: $44,280/year ($3,690/month) Current Rent Roll * Unit 1F: 1BR/1BA duplex-down | $1,100/month | Lease through 5/31/27 * Unit 1R: 2BR/1BA | $700/month | Month-to-month * Unit 2F: 2BR/1BA | $690/month | Month-to-month * Coach House: 2BR/1BA | $1,200/month | Month-to-month Three of the four units are month-to-month, providing immediate flexibility to implement a value-add strategy while maintaining current cash flow. Ideally located in the heart of Pilsen, just steps from the vibrant 18th Street corridor featuring neighborhood favorites including 5 Rabanitos, Los Comales, Pizza Nova, and Carniceria Maribel. Conveniently located near the CTA Pink Line, UIC, the Illinois Medical District, and Downtown Chicago. First showings by appointment only July 10, 11 & 12. Buyer to independently verify zoning, legal unit count, redevelopment potential, and all property information.

1801 W 21St Place, Chicago
$479,900
3 Beds ⋅ 2 Baths ⋅ 12724878 MLS ⋅ ACTIVE Status
LOCATED IN ONE OF THE HOTTEST AREAS OF CHICAGO. THIS NEWER CONSTRUCTION PILSEN CONDO IS LIGHTLY LIVED-IN, EQUIPT WITH ELEGANT SHAKER STYLE KITCHEN CABINETRY, QUARTZ COUNTERTOPS, HIGH END PLUMBING FIXTURES, MODERN LIGHT FIXTURES, SAMSUNG STAINLESS STEEL APPLIANCE PACKAGE, OAK FLOORS THROUGHOUT, 9 FEET CEILINGS. MASTER BEDROOM WITH EN-SUITE MASTER BATH AND DUAL VESSEL SINKS. A LARGE CUSTOM WALK-IN CLOSET. REAR DECK. ONE COVERED PARKING SPACE(CAR PORT) INCLUDED IN THE PRICE. LOW MONTHLY HOA @ $190. PET FRIENDLY, INVESTOR FRIENDLY...ALSO BUYER FRIENDLY, SO COME AND SEE IT IN PERSON!!! THE PILSON AREA IS A COMMUTERS DREAM, MINUTES AWAY FROM HIGHWAYS: 55, 290, 90/94. STEPS FROM PUBLIC TRANSPORTATION: PINK LINE AND ASHLAND/18th STREET BUS ROUTES. SUPER CLOSE TO COSTCO, MEDICAL DISTRICT AND DOWNTOWN.

1738 W 17Th Street Unit #2, Chicago
$399,000
12721069 MLS ⋅ ACTIVE Status
Remarkable Investment Opportunity in the Heart of Pilsen! This is a fantastic, fully-gutted mixed-use building, ready for immediate development. The blueprints and permits are already in place, making it a seamless transition for you to bring your business to the first floor, while enjoying two spacious, two-bedroom apartments on the second floor. Whether you're looking to start a business, expand your current one, or simply invest in a prime location, this property offers endless possibilities. Located in the vibrant and ever-growing Pilsen neighborhood, you'll be surrounded by a dynamic arts scene, unique local businesses, and an incredible sense of community. This is your chance to own a piece of real estate in one of Chicago's most sought-after areas. Don't miss out on this incredible opportunity - schedule a viewing today!

1702 S Paulina Street, Chicago
$449,000
3 Beds ⋅ 3 Baths ⋅ 12715696 MLS ⋅ ACTIVE Status
Great Location On This Single Family With 3 levels of Living space!! Little Italy and West Pilsen Location....the Best of Two worlds. Walk to Little Italy Restaurants and Pilsen nigth life.. Minutes To University Of,Illinois ,Rush and Cook County Hospitals. Few Minutes From I-290 & I55 express ways!!.. and......Downtown,,,, Waooooo...this a 4 Bedroom 2.5 Bath Single Family Home with 2,5 Brick Car Garage....

2237 S Oakley Avenue, Chicago
Start Your Search



The data relating to real estate for sale on this website comes in part from the Broker Reciprocity program of Midwest Real Estate Data LLC. Real Estate listings held by brokerage firms other than our company are marked with the MRED Broker Reciprocity logo or the Broker Reciprocity thumbnail logo (the MRED logo) and detailed information about them includes the names of the listing brokers. Some properties which appear for sale on this website may subsequently have sold and may no longer be available. The accuracy of all information, regardless of source, including but not limited to square footages and lot sizes, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. The information being provided is 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.

Copyright 2026 MRED LLC. All rights reserved.

Based on information submitted to the MLS Grid as of . All data is obtained from various sources and has not been, and will not be, verified by broker or MLS Grid. 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.

NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the DMCA) provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to DMCAnotice@theMLSGRID.com.

The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner’s behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.

Some listings have been excluded from this website.