Tri-Taylor Real Estate

Welcome to the vibrant neighborhood of Tri-Taylor in Chicago, Illinois. This charming community is nestled in Cook County and is known for its unique character and convenient location.

Tri-Taylor offers residents a perfect blend of urban amenities and a cozy neighborhood feel. The tree-lined streets are dotted with beautiful homes, ranging from historic brownstones to modern condos, making it an attractive area for a diverse range of residents.

One of the highlights of Tri-Taylor is its proximity to the renowned Illinois Medical District, making it a popular choice for medical professionals and students. The neighborhood also boasts a strong sense of community, with local shops, restaurants, and parks that cater to residents of all ages.

With easy access to public transportation and major highways, Tri-Taylor provides a seamless commute to downtown Chicago and other parts of the city. Whether you're looking to enjoy a leisurely stroll in the park or explore the vibrant dining scene, Tri-Taylor has something for everyone.

Come and discover the unique charm of Tri-Taylor – a neighborhood that seamlessly combines urban convenience with a welcoming community atmosphere. Experience the best of city living in this hidden gem of Chicago.

Newest Listings in Tri-Taylor

$1,850,000

12706824 MLS ⋅ ACTIVE Status

This exceptional investment opportunity offers the acquisition of a modern 6-unit multifamily asset ideally located in the rapidly growing Tri-Taylor neighborhood of Chicago. Constructed in 2014, the property features condominium-quality finishes, efficient building systems, and thoughtfully designed floor plans that continue to attract strong tenant demand and support premium rental rates. The asset presents investors with a rare opportunity to acquire a newer construction multifamily building with minimal deferred maintenance and lower ongoing capital expenditure requirements compared to the area's aging housing stock. Its combination of modern amenities, strong rental appeal, and strategic location near major medical campuses, universities, public transportation, and downtown Chicago positions the property for stable cash flow and long-term appreciation potential. Unit mix: 1 duplex down-4 bed/4 bath, 1 duplex down- 3 bed/2.1 bath, 4 simplex- 2 bed/ 2bath

504 S Oakley Boulevard, Chicago

$349,888

12702426 MLS ⋅ ACTIVE Status

awesome store front location, just west of downtown and west loop, this location in the medical district, offer the value of location, with over 1600 sq feet of space, additional 1500 sq ft basement for storage, featuring high ceilings, 6 private offices/treatment rooms, spacious reception/waiting area, one and half bathroom.can be massage store.

2322 W Roosevelt Road Unit #1, Chicago

$695,000

2 Beds ⋅ 4 Baths ⋅ 12699102 MLS ⋅ ACTIVE Status

Welcome to this stunning, fully remodeled 4-bedroom, 3.5 bathroom home in the highly sought-after Tri-Taylor neighborhood, where timeless character meets today's modern design. From the moment you step inside, you'll be impressed by the beautiful hardwood floors that flow throughout the main level and the bright, open floor plan designed for everyday living and entertaining. The show stopping kitchen features sleek quartz countertops, a large center island, premium cabinetry, and a dramatic quartz backsplash. Every detail has been thoughtfully selected to create a space that is both stylish and functional. Upstairs, you'll find two spacious bedroom suites, each featuring its own private bathroom, creating the perfect retreat for homeowners and guests alike. The fully finished walkout basement adds incredible living space with two additional bedrooms, a beautifully appointed third full bathroom, and convenient exterior access-perfect for guests, extended family, or a private home office setup. Major updates include new windows throughout, all new mechanical systems, and quality finishes from top to bottom, giving you complete peace of mind. Outside, enjoy a charming rear deck ideal for grilling or relaxing, along with a detached two-car garage. Located in the heart of Tri-Taylor, this home offers unbeatable convenience. Enjoy walking distance to neighborhood restaurants, cafes, and parks while being just minutes from the Illinois Medical District, downtown Chicago, major expressways, and public transportation. Front porch concrete is in process of being replaced! Schedule your showing today!

1033 S Claremont Avenue, Chicago

$299,500

2 Beds ⋅ 2 Baths ⋅ 12666658 MLS ⋅ ACTIVE Status ⋅ Tri-Taylor BLDG.

Welcome home to this beautifully maintained 2-bedroom, 2-bathroom condo in an investor friendly building, in the heart of Chicago's vibrant Near West Side. This bright and inviting residence offers an ideal blend of comfort, convenience, and modern updates, making it the perfect place to call home. The thoughtfully updated kitchen features a full suite of newer stainless steel appliances, including a dishwasher, oven, microwave, and refrigerator, all replaced in 2025. Enjoy peace of mind with a brand-new HVAC system installed in 2025, ensuring year-round comfort and energy efficiency. The bathrooms were tastefully remodeled in 2022, providing a fresh and contemporary feel throughout the home. The spacious layout offers generously sized bedrooms, including a primary suite with a private bath, while large windows fill the living spaces with natural light. Whether you're entertaining guests or enjoying a quiet evening at home, this condo provides the flexibility and functionality today's buyers are seeking. Enjoy easy access to some of Chicago's most exciting destinations. Situated near the rapidly growing Illinois Medical District, the neighborhood offers convenient access to major employers including Rush University Medical Center, Stroger Hospital, and the University of Illinois Chicago. Commuters will appreciate proximity to the CTA Blue Line, Pink Line, I-290, and several bus routes, providing quick access to Downtown Chicago, the West Loop, Fulton Market, and beyond. With ongoing development and investment throughout the area, this location continues to attract homeowners and investors alike. Don't miss this opportunity to own a move-in ready condo with recent updates in one of Chicago's most conveniently located and rapidly appreciating neighborhoods.

1015 S Western Avenue Unit #4, Chicago

$874,900

9 Beds ⋅ 4 Baths ⋅ 12653329 MLS ⋅ ACTIVE Status

Welcome to this beautifully maintained classic 2-unit brick building. Located in the vibrant Tri-Taylor neighborhood, just steps away from the Medical District and UIC campus. This prime location offers easy access to a variety of restaurants, shops, and public transportation options, making it perfect for investors and owner-occupants. All units have tenants on a month to month arrangement. Private parking in the back of building with alley access.

2312 W Taylor Street, Chicago

$230,000

12279296 MLS ⋅ ACTIVE Status

Don't miss out on the opportunity to build in the thriving Tri-Taylor neighborhood! This unique corner lot parcel of land offers the perfect redevelopment potential for retail and or residential use, making it an ideal investment for investors or buyers looking to create their vision of the perfect home from the ground up. Why is This Lot So Exceptional: * Prime location: Situated on bustling Taylor Street near Ogden Avenue but also can access property from the residential 900 block of Bell Ave. * High Visibility: Walking distance to the numerous restaurants, Illinois Medical District, United Center, parks and community conveniences. * Thriving Community: A vibrant mix of homes, retail, and activities. * Excellent Transit Access: Convenient public transportation options. Additional Highlights: * Unique location bordering a beautifully landscaped cul-de-sac on Bell Avenue. * Zoned PD-30, allowing for multi-family or mixed-use development. * Steps from the newly created development, featuring exciting new retail, restaurants and hotel, creating even more vibrancy and demand in the area. * Taylor Street is a hub of residential and commercial activity with a strong presence of companies and ongoing development. The Illinois Medical District alone brings a high density of people daily to its campus, driving demand for new growth and opportunities. These are just a few of the many reasons why you would want to commit to this neighborhood, don't miss the chance to be part of it! Act now to secure this fantastic parcel in the heart of Chicago's Historic Tri-Taylor Neighborhood!

2224 W Taylor Street, Chicago

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