Heart of Chicago Real Estate

Heart of Chicago Real Estate

**Discover the Heart of Chicago: A Neighborhood Like No Other**

Nestled in the vibrant city of Chicago, the Heart of Chicago neighborhood offers a unique blend of rich cultural heritage, community spirit, and urban convenience. Located in Cook County, this charming area is a true reflection of the Windy City’s diverse character and welcoming ambiance.

One of the standout features of the Heart of Chicago is its rich Italian heritage, evident in the delicious eateries and bakeries that line the streets. From classic pizzerias to family-owned trattorias, food lovers will find themselves in culinary heaven. Stroll down the tree-lined avenues and savor the aroma of freshly baked bread or indulge in a delectable cannoli, all while enjoying the warm, inviting atmosphere that this neighborhood exudes.

The Heart of Chicago is not just about great food; it’s also a hub for community engagement. Residents take pride in their neighborhood, hosting various events throughout the year, from summer street festivals to winter holiday celebrations. These gatherings foster a sense of belonging and camaraderie among neighbors, making it an ideal place for families and individuals alike.

For those who appreciate the outdoors, the Heart of Chicago offers access to beautiful parks and recreational spaces. Enjoy a leisurely afternoon at the nearby parks, where you can unwind, play sports, or simply soak in the beauty of nature amidst the urban landscape.

With its rich history, vibrant community, and convenient access to public transportation, the Heart of Chicago is not just a neighborhood; it’s a lifestyle. Whether you’re looking to buy, rent, or simply explore, this enchanting area promises a warm welcome and endless opportunities for enjoyment. Come discover the Heart of Chicago, where every corner tells a story!

Newest Listings in Heart of Chicago

$475,000
3 Beds ⋅ 3 Baths ⋅ 12715696 MLS ⋅ NEW 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
$789,900
6 Beds ⋅ 4 Baths ⋅ 12714347 MLS ⋅ ACTIVE Status

2012 W 21St Place, Chicago
$599,999
9 Beds ⋅ 4 Baths ⋅ 12710176 MLS ⋅ ACTIVE Status
Discover an exceptional investment opportunity in the heart of Pilsen! This spacious property offers a total of 9 bedrooms and 4 bathrooms, providing outstanding income potential for both investors and owner-occupants. The first and second floor units each feature 3 bedrooms. The lower level adds even more value with a 2 bedroom garden apartment plus a separate studio apartment, offering additional rental income possibilities. Conveniently located near parks, schools, restaurants, shopping, public transportation, and with easy access to downtown Chicago, this versatile multi-unit is an excellent addition to any investment portfolio. Don't miss your chance to own a high-income property in one of Chicago's most sought-after neighborhoods!

2340 W 21St Place, Chicago
$345,000
3 Beds ⋅ 2 Baths ⋅ 12707832 MLS ⋅ ACTIVE Status
Modern 3-Bed Oasis in the Heart of Pilsen! Welcome home to this impeccably designed 3-bedroom, 2-bathroom condo, offering sleek modern aesthetics and high-end finishes. Built in 2018, this all-masonry first-floor home is flooded with light from a sunny southern exposure. The open-concept living space is perfect for entertaining, featuring custom flat-panel cabinetry, quartz countertops, and premium stainless steel appliances. Professionally designed and freshly painted, the condo includes a brand-new furnace and water heater. Enjoy true city living with a spacious private rear patio and the convenience of in-unit, full-size laundry. Located just two blocks from the Pink Line and minutes from I-55/I-290, you are perfectly situated near UIC, the Medical District, Taylor Street, and Pilsen's best dining/shopping. Easy Street Parking Available. Move-in-ready-this is a true Pilsen gem!

2108 W 18Th Place Unit #2, Chicago
$500,000
6 Beds ⋅ 4 Baths ⋅ 12704298 MLS ⋅ ACTIVE Status
In the heart of Pilsen, Legal 3 Flat Building. Unit #1 is a 2bd/1ba, which features a separate Living room and Dining room area. Unit #2 is the same floorplan, featuring vaulted ceilings in the primary bedroom, washer and dryer in unit with access ladder up to the unfinished Attic. Lower level has a 1 bedroom unit. There is a small grass area in the back of the building with a 2 car garage. Rents are below market value and all 3 tenants are month to month. Excellent opportunity to add value for both Investors and/or Owner Occupants. Close proximity to shopping, restaurants, art galleries, and the Medical District.

2144 W 19Th Street, Chicago
$1,250,000
12 Beds ⋅ 8 Baths ⋅ 12700558 MLS ⋅ ACTIVE Status
Located in the heart of Pilsen, this well-maintained, all-brick property underwent a complete gut rehab in 2014 and features four legal dwelling units. The property consists of a three-unit front building and a separate coach house with additional storage space below. Each unit has been fully remodeled with modern finishes and includes in-unit laundry, central air conditioning, and updated interiors designed for comfortable living. Unit 1's lease expires on August 31, 2026, providing an excellent opportunity for an owner-occupant or added flexibility for future leasing plans. This is a rare investment opportunity in one of Chicago's most sought-after neighborhoods, offering strong rental income potential and pride of ownership.

2110 W 18Th Place, Chicago
$1,095,000
12697652 MLS ⋅ ACTIVE Status
5-unit multifamily investment opportunity in Chicago's historic Pilsen neighborhood! The property features four 2BR/1BA units and an incredibly spacious, detached rear Coach House (3BR/1BA) - offering a high-demand mix with strong rental upside. Interiors feature updated finishes and classic wood flooring throughout. Units have central heat and shared laundry. Laundry is shared in the basement. Highly desired location just blocks from 18th Street's dining scene and a quick two-block walk to the Damen Pink Line station for an effortless downtown commute. Current revenue is 107K and market revenue is ~115k. Buy at a 10x GRM and stabilize at a 9.5x GRM or ~7 per cent Cap Rate

1801 W 21St Street, Chicago
$1,395,000
12697616 MLS ⋅ ACTIVE Status
Fantastic 7-unit multifamily investment opportunity in Chicago's historic Pilsen neighborhood! This turnkey building features an ideal high-demand unit mix: two 1BR/1BA, four 2BR/1BA, and one 3BR/1BA. Units boast modern finishes and LVP flooring throughout. High demand location just blocks from 18th Street's dining scene and a quick two-block walk to the Damen Pink Line station for an effortless downtown commute. Units feature central heat and window AC (except for the former storefront unit, 1F, which has central heat and AC). Building has shared laundry in the basement of the neighboring property at 1801 W 21st. Buy as a package or individually. Current rents are well below market and both units CH1 and 3F were recently vacated. Price reflects a 10x GRM on market rents.

1759 W 21St Street, Chicago
$659,900
7 Beds ⋅ 4 Baths ⋅ 12644428 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
$659,900
3 Beds ⋅ 2 Baths ⋅ 12698348 MLS ⋅ ACTIVE Status
Stop scrolling. This is the penthouse buyers wait years to find. Brand-new 2025 construction in a boutique elevator building, this extra-wide 3-bedroom, 2-bath home delivers something almost impossible to find in Pilsen: breathtaking downtown skyline views, an elevator that takes you all the way to your private rooftop deck, and a level of space and design that feels more like a single-family home than a condo. Natural light pours through oversized windows, illuminating the wide-open living space, rich hardwood floors, and seamless flow to a spacious balcony-perfect for morning coffee or sunset cocktails with the skyline as your backdrop. The designer kitchen is built for both everyday living and entertaining, featuring a large island, custom cabinetry with pantry storage, Samsung stainless steel appliances, and a vented exterior hood. The primary suite is a true retreat with a generous walk-in closet and a spa-inspired bath showcasing a dual vanity, oversized shower with rain head and body sprays, and stylish barn doors. Two additional bedrooms offer plenty of flexibility for guests, family, or work-from-home needs, while the oversized laundry room provides the kind of storage every homeowner wishes they had. Need even more space? The enormous private storage room in the basement is large enough to become your home gym, office, hobby room, or all three. Then there's the showstopper: your private rooftop deck. Ride the elevator straight to the top, relax beneath the brand-new pergola, and take in spectacular skyline and sunset views that are simply the best in the building. With only two residences per floor, garage parking included, and an unbeatable location on one of Cermak's quieter stretches, you'll enjoy the best of every world. Walk to the Damen Pink Line, explore the beloved restaurants of Heart of Italy, grab incredible Thai at Ghin Khao just across the street, and immerse yourself in Pilsen's celebrated dining scene. Luxury, privacy, views, and location-all wrapped into one unforgettable penthouse. This isn't just another new construction condo. It's the one everyone will be talking about.

2135 W Cermak Road Unit #4N-PH, Chicago
$1,549,000
7 Beds ⋅ 7 Baths ⋅ 12685158 MLS ⋅ ACTIVE Status

Chicago
$1,200,000
11 Beds ⋅ 8 Baths ⋅ 12691518 MLS ⋅ ACTIVE Status
Large rarely seen 4 unit building where all 4 units are duplexes providing 2 floors for extra space in each unit. All Units are rented below market rents. Great, sought after area on lively 18th street is short walk to several nearby restaurants, parks, art center, cta pink line. Near Ashland Costco, uic, rush medical districts and hospitals with staff often renting the units. No vacancy in 10 years. 3 units are 3 bed 2 bath and one unit is 2 bed, 2 bath. 5191 square foot multi family home with 11 bedrooms and 8.0 bathrooms. Kitchens with stainless steel appliances with wonderful high ceilings. Income generating property with no vacancies in sought after area located at 2148 W 18th St, Chicago, IL 60608.

2148 W 18Th Street, Chicago
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