West Side Homes with Contemporary Style

Welcome to the vibrant West Side of Chicago, a neighborhood that beautifully marries rich history with contemporary flair. Nestled in Cook County, this dynamic area is known for its diverse culture, thriving arts scene, and a strong sense of community. As you stroll through tree-lined streets, you'll discover a delightful mix of historic architecture and modern developments that reflect the neighborhood's evolution.

The West Side is particularly renowned for its homes with contemporary style, showcasing innovative designs that cater to today’s discerning buyers. From sleek, minimalist facades to open-concept interiors flooded with natural light, these residences offer a perfect blend of comfort and sophistication. Imagine hosting gatherings in spacious living areas that seamlessly connect to gourmet kitchens, or enjoying quiet evenings in private outdoor spaces designed for relaxation and entertainment.

In addition to stunning homes, the West Side boasts an array of amenities that enhance the quality of life for its residents. Explore local parks, trendy cafes, and unique boutiques that contribute to the neighborhood's vibrant atmosphere. The West Side is also well-connected to public transportation, making commuting to downtown Chicago a breeze.

Whether you're a first-time homebuyer or looking to upgrade, the contemporary homes in the West Side offer a unique opportunity to be part of a neighborhood that celebrates both its heritage and its future. Experience the charm of this community, where modern living meets historical richness, and find your dream home today!

Newest West Side Homes with Contemporary Style

$549,999

5 Beds ⋅ 5 Baths ⋅ 12795074 MLS ⋅ ACTIVE Status

Thoughtfully composed for modern ownership, 1433 S. Trumbull introduces a new-construction two-flat where refined design and income-producing flexibility share one cohesive address. Anticipated for November 2026 delivery, the property pairs a contemporary brick-and-Hardie exterior with two independently functional residences, a two-car garage, rear deck, fenced backyard, and approximately 2,900 square feet of combined living space. The approximately 1,900-square-foot duplex-up unfolds across two well-proportioned levels with three bedrooms and 2.5 baths. An open-concept main floor connects the living, dining, and kitchen areas, while expansive west-facing windows invite warm afternoon light. Wide-plank LVT flooring, five-inch baseboards, crown molding, modern lighting, and crisp black accents establish a polished visual language throughout. At the center of the home, custom black-and-white cabinetry is paired with quartz countertops, a substantial island, and a complete GE stainless steel appliance package. Generous storage and workspace support daily routines and larger gatherings, while the adjoining rear deck extends the living space outdoors. Upstairs, the primary suite offers a quiet, design-forward retreat with a spa-inspired bath. A freestanding soaking tub, glass-enclosed walk-in shower with full-body sprayers, double vanity, wood-look accent wall, and curated Kohler, Delta, and Signature Hardware fixtures create a layered, restorative setting. Two additional bedrooms, a second full bath, and second-level laundry complete the duplex with intention. The approximately 1,000-square-foot garden residence adds two bedrooms, two full baths, 10-foot ceilings, a private entrance, full kitchen, in-unit laundry, and separate utility meters. Its independent configuration creates meaningful versatility for rental income, guests, or other flexible living arrangements without compromising privacy. Set in North Lawndale, the home is near historic Douglass Park, the Garfield Park Conservatory, and La Catedral Cafe, a locally loved destination for Guadalajara-inspired breakfast and coffee. The Kedzie Pink Line station, CTA bus connections, and nearby I-290 provide convenient access to the West Loop and Downtown Chicago. More than a new build, 1433 S. Trumbull is a thoughtful approach to city living-designed to support comfort today while creating possibilities for what comes next. Photos depict the previously completed model at 2435 W. Congress Parkway and are representative of the planned design and finishes at 1433 S. Trumbull. Qualified buyers may be eligible for up to $100,000 in purchase-price assistance through the City of Chicago's Building Neighborhoods and Affordable Homes Program. Income, owner-occupancy, program guidelines, and fund availability apply; buyers should independently verify eligibility with the City of Chicago.

1433 S Trumbull Avenue, Chicago

$724,900

11 Beds ⋅ 7 Baths ⋅ 12792292 MLS ⋅ ACTIVE Status

Discover an incredible multi-family asset in a booming neighborhood with unlimited income potential. Originally constructed as luxury condominiums-offering an investor the future flexibility to deconvert and sell individually-this fully gated building delivers top-notch construction and modern convenience throughout. Property Highlights: Spacious Layouts: Three expansive units, each offering approximately 1,400 sq. ft. of living space with hardwood floors throughout and convenient in-unit laundry. Unit Features: Each unit boasts 3 bedrooms and 2 full bathrooms, including a private en-suite 2nd bath in the primary bedroom. Enjoy a large, well-appointed kitchen and dining area with abundant cabinetry and newer stainless steel appliances, plus private outdoor decks accessible from both the primary bedroom and kitchen. Flexible Living Options: The first-floor unit was originally configured as a 5-bedroom, 3-bathroom duplex-down with a spacious family room. Currently converted to a 2-bedroom, 1-bathroom layout, it can easily be converted back for related living or duplex-down arrangements. Utilities & Efficiency: Independent HVAC and central air for every unit. Equipped with 4 gas meters and 4 electric meters-the owner pays water only. Recent Upgrades & Maintenance: Brand new roof installed in 2023, newer mechanical equipment in most units, and recent tuckpointing and block sealing (October 2026). Exterior & Security: Fully gated property featuring 3 secure parking spaces and dedicated secure storage for every unit. Prime Location: Situated directly across the street from a wonderful neighborhood park in a rapidly growing area surrounded by new development. Financial Potential: With estimated rental values easily reaching $2,500 per unit, this turnkey property represents a fantastic, high-yield addition to any investor's portfolio. Units 1-3 are projected, unit 4 is actual.

720 N Central Park Avenue, Chicago

$1,599,900

2 Beds ⋅ 4 Baths ⋅ 12786938 MLS ⋅ ACTIVE Status

Modern home in West Town, which Time Out just named one of the world's 20 coolest neighborhoods (No. 18 for 2026). It's also in the top-rated Mitchell Elementary School District. Designed by Studio Dwell, this 4,100 sq ft house has open, sun-filled living space and top-quality finishes throughout. The main floor brings the living, dining, and family rooms together with the kitchen: Italian Arclinea cabinets, Miele, Sub-Zero, and Gaggenau appliances, a serving area, and a bar with a wine fridge. Oversized custom Pella sliding glass doors open to a large private deck with a natural gas grill hookup. There's more outdoor space on top of the garage: a custom rooftop deck with a pergola and privacy panels. The primary suite takes up half of the second floor and feels like a very good hotel. Closet space is generous: a fully organized walk-in plus 18 linear feet of reach-in closets. Bathrooms have Zuma, Duravit, Grohe, and Toto fixtures, and two are finished in Japanese glass tile from Oramano. Hardwood floors run through the first and second levels. The lower level has radiant-heated epoxy floors, a rec room with a wet bar, and a FireOrb fireplace by Spark Modern Fires. Other details: Lutron lighting controls, dual HVAC, built-in speakers, and a 2-car garage. Walk to Smith Park, the Grand Ave Metra station, and the shops, galleries, and restaurants along Chicago Ave. A few local favorites close by: coffee at Dark Matter or Match-a, pastries at Guillotine Bakery, dinner at Elina's or Sabroso, drinks at Lemon or Tuman's Tap, home finds at The Golden Triangle and Neybir Home, and the latest show at Andrew Rafacz Gallery.

2325 W Erie Street, Chicago

$819,000

3 Beds ⋅ 4 Baths ⋅ 12729296 MLS ⋅ ACTIVE Status

70 DAYS OUT. Chicago developer Home& is building the latest addition to the "The 12", known as Phase 3. The original project started on the former site of William King Elementary that once sat at 2500 W. Lexington St. - one of the 50 CPS schools shuttered in 2014. Since the project first began in 2020, Home& successfully sold out of both the 1st and 2nd Phases of this project, which are located on Polk, Lexington, and a portion of Fillmore, which has brought rapid growth to the Tri-Taylor area. With delivery expected in late December of this year, we're pleased to present you the latest offering of this new construction rollout, which consists of 10, 4Bed/3.1Bath SFH's, on the 2500 W block of Fillmore. Each home features a contemporary floor-plan with generously proportioned rooms throughout - designed for effortless everyday living and entertaining alike. The first floor consists of an open layout that flows seamlessly from the living room all the way into the kitchen. Additional features of the first floor include a rear mudroom, pantry, powder room, and access to the back deck and yard. The second floor is highlighted by three large bedrooms, one of which is a gorgeous primary suite with vaulted ceilings, two walk-in closets, and a spa-like bath with dual vanities, and a walk-in shower. Second laundry hookup is in place for added convenience on this level. The basement offers a spacious family/rec room complimented with a fully integrated wet-bar, a fourth bedroom, full bath, and a large laundry room. Conveniently located near the Blue Line, I-290, Little Italy, the Medical District, United Center, multi-billion dollar 1901 project, parks, schools, restaurants, and shops. Buyers still have the opportunity to customize select finishes, making it possible to put a personal stamp on your new home before move-in. INTERIOR PHOTOS ARE OF LAST PROJECT (PHASE 2).

2519 W Fillmore Street, Chicago

$819,000

3 Beds ⋅ 4 Baths ⋅ 12717658 MLS ⋅ ACTIVE Status

2517 W Fillmore Street, Chicago

$670,000

4 Beds ⋅ 4 Baths ⋅ 12707063 MLS ⋅ ACTIVE Status

Rarely available newer huge single family construction in Pilsen. Beautiful curve appeal is just the beginning. This 3-level single family has all the space you need and more. Main level entrance welcomes you to High 10ft ceilings and grand open space area with a fire place and open concept kitchen eating area. The hardwood floors compliment the open kitchen area and and complete main level. Entertaining here is waiting to happen. First floor also hosts a 1 bedroom, full bath and clear hallway access to the outside patio and 2 car Brick garage with extra party door. Open staircase leads to the 2nd floor and its 3 add'l bedrooms and full bath. Front high ceiling bedroom is huge with a beutiful view of the chicago skyline. Rear Master bedroom is grand with a 14ft at peak high Cathedral Ceiling and private balcony. Wait there's more. The basement is set up for entertaining and family gatherings. Clomplete open space with an extra guestroom and full bath. Laundry area. Basement has access to the rear patio. There are two (2) HVAC systems. Close to 18th Street andBlue Island the Heart of Pilsen. This house was built to owners needs and expectations at the time that it was constructed. It's now time for new owners to make their own changes or updates and call this beauty their own. Bring your ideas and personal touches and enjoy what Pilsen is all about.

1435 W 16Th Street, Chicago

$599,997

5 Beds ⋅ 5 Baths ⋅ 12662032 MLS ⋅ ACTIVE Status

Thoughtfully composed for modern ownership, 1435 S. Trumbull introduces a new-construction two-flat where refined design and income-producing flexibility share one cohesive address. Anticipated for November 2026 delivery, the property pairs a contemporary brick-and-Hardie exterior with two independently functional residences, a two-car garage, rear deck, fenced backyard, and approximately 2,900 square feet of combined living space. The approximately 1,900-square-foot duplex-up unfolds across two well-proportioned levels with three bedrooms and 2.5 baths. An open-concept main floor connects the living, dining, and kitchen areas, while expansive west-facing windows invite warm afternoon light. Wide-plank LVT flooring, five-inch baseboards, crown molding, modern lighting, and crisp black accents establish a polished visual language throughout. At the center of the home, custom black-and-white cabinetry is paired with quartz countertops, a substantial island, and a complete GE stainless steel appliance package. Generous storage and workspace support daily routines and larger gatherings, while the adjoining rear deck extends the living space outdoors. Upstairs, the primary suite offers a quiet, design-forward retreat with a spa-inspired bath. A freestanding soaking tub, glass-enclosed walk-in shower with full-body sprayers, double vanity, wood-look accent wall, and curated Kohler, Delta, and Signature Hardware fixtures create a layered, restorative setting. Two additional bedrooms, a second full bath, and second-level laundry complete the duplex with intention. The approximately 1,000-square-foot garden residence adds two bedrooms, two full baths, 10-foot ceilings, a private entrance, full kitchen, in-unit laundry, and separate utility meters. Its independent configuration creates meaningful versatility for rental income, guests, or other flexible living arrangements without compromising privacy. Set in North Lawndale, the home is near historic Douglass Park, the Garfield Park Conservatory, and La Catedral Cafe, a locally loved destination for Guadalajara-inspired breakfast and coffee. The Kedzie Pink Line station, CTA bus connections, and nearby I-290 provide convenient access to the West Loop, Downtown Chicago, and surrounding neighborhoods. More than a new build, 1435 S. Trumbull is a thoughtful approach to city living-designed to support comfort today while creating possibilities for what comes next. Photos depict the previously completed model at 2435 W. Congress Parkway and are representative of the planned design and finishes at 1435 S. Trumbull. Qualified buyers may be eligible for up to $100,000 in purchase-price assistance through the City of Chicago's Building Neighborhoods and Affordable Homes Program. Income, owner-occupancy, program guidelines, and fund availability apply; buyers should independently verify eligibility with the City of Chicago.

1435 S Trumbull Avenue, Chicago

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West Side Homes with Contemporary Style

Newest West Side Homes with Contemporary Style

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