Heart of Chicago Real Estate

Heart of Chicago Real Estate

Welcome to the Heart of Chicago, a vibrant neighborhood that truly embodies the spirit of this iconic city! Nestled in Cook County, this area is renowned for its rich cultural tapestry, diverse community, and a lively atmosphere that attracts both residents and visitors alike.

The Heart of Chicago is characterized by its charming tree-lined streets and historic architecture, offering a unique blend of old-world charm and modern conveniences. As you stroll through the neighborhood, you'll discover an array of local shops, trendy boutiques, and delightful eateries that showcase the culinary diversity of Chicago. Whether you're in the mood for authentic Italian fare, a cozy café, or a lively bar, the Heart of Chicago has something to satisfy every palate.

Families will appreciate the neighborhood’s excellent schools and parks, providing ample opportunities for outdoor recreation and community engagement. With its close-knit community vibe, residents often gather for local events, farmers' markets, and festivals, making it easy to forge lasting connections with neighbors.

Moreover, the Heart of Chicago boasts convenient access to public transportation, making commuting to downtown or exploring other parts of the city a breeze. With its proximity to major attractions, theaters, and cultural landmarks, residents can enjoy the best of urban living while having a peaceful retreat to call home.

In summary, the Heart of Chicago is not just a place to live; it’s a vibrant lifestyle filled with culture, community, and convenience. Come and experience the warmth and charm of this beloved neighborhood!

Newest Listings in Heart of 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
$1,549,000
7 Beds ⋅ 7 Baths ⋅ 12725582 MLS ⋅ ACTIVE 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
$499,000
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
$789,900
6 Beds ⋅ 4 Baths ⋅ 12714347 MLS ⋅ ACTIVE Status

2012 W 21St Place, Chicago
$475,000
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
$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
$579,000
3 Beds ⋅ 2 Baths ⋅ 12641212 MLS ⋅ ACTIVE Status
Amazing, extra-wide, 3 bed / 2 full bath Condo located in the heart of Pilsen. This like-new elevator building (the elevator goes all the way up to the roof) includes in-unit laundry, an indoor garage parking space as well as a gigantic roof top area with some pretty stunning views that almost have to be seen to be believed. The unit also faces south which adds to the quiet, serene atmosphere. Inside features an open living area, hardwood floors, larger windows for tons of natural light, and a sizable, attached, private balcony. Modern kitchen with island, Samsung SS appliances, vented hood, and custom cabinets including pantry. Private master suite offers large walk-in closet, oversized shower w/ rain head & wall spray, 2x vanity, and barn style doors. Large 2nd bathroom and generous-sized rooms for the 2nd/3rd bedrooms. All bedrooms have upgraded, custom closet shelving that are definitely pretty sharp. Storage closet in each unit and possibility to purchase massive additional storage/office/work out rooms in the building on the 1st floor. This is a great location with plenty of shops and restaurants all around. Easy expressway and transportation access as well. Summer in the city is officially underway, do not miss out!!!

2135 W Cermak Road Unit #3S, Chicago
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