Search Tri-Taylor Homes For Sale

Homes for Sale in Tri-Taylor Chicago: A Hidden Gem with Old-World Charm

The Tri-Taylor neighborhood in Chicago, located just west of the Illinois Medical District and near Little Italy, offers an inviting blend of historic charm and modern convenience. Named after its triangular shape and Taylor Street, this community is one of Chicago’s lesser-known gems, making it a perfect spot for homebuyers looking for unique properties. Many of the homes here, including 19th-century rowhouses and vintage two- and three-flats, have landmark status, contributing to the area's preserved character.

Why Choose Tri-Taylor?

Tri-Taylor is an ideal location for those seeking proximity to the city while enjoying a quieter, residential atmosphere. The neighborhood is rich in history and features classic European-style homes, as well as newer condos and lofts. With easy access to Rush University Medical Center and UIC, it's a prime spot for medical professionals, students, and anyone who values a short commute into downtown Chicago.

Types of Homes in Tri-Taylor

  • Single-family homes: Historic rowhouses with character and updated interiors.
  • Two- and three-flats: Ideal for investors or those looking for rental income opportunities.
  • Condos and Lofts: Offering modern living with vintage charm, often featuring exposed brick and timber beams.
  • Townhomes: For those who want more space without the upkeep of a detached home.

Living in Tri-Taylor

Tri-Taylor’s prime location means residents can enjoy the best of both worlds. You’re just minutes from downtown Chicago, yet you get to enjoy a quieter, more relaxed vibe. The neighborhood offers proximity to Little Italy’s legendary restaurants on Taylor Street and the dining spots in nearby Greektown. Tri-Taylor is also close to Douglas Park, a green space perfect for outdoor activities, and 13th Street Playlot Park, offering a neighborhood escape for families.

Explore Nearby Communities

If you love Tri-Taylor, you may also want to explore nearby areas like:

  • West Loop: Known for its trendy restaurants, vibrant nightlife, and historic loft conversions, West Loop is perfect for those who want a bustling urban environment close to Tri-Taylor.
  • University Village: A vibrant community with an academic focus.
  • River North: For those who want to be closer to Chicago’s nightlife and galleries.

Start Your Home Search in Tri-Taylor

Whether you're looking for a historic rowhouse, a modern loft, or a family-friendly two-flat, Tri-Taylor has something for everyone. Start exploring homes for sale in Tri-Taylor Chicago and find your perfect home in this charming and well-preserved neighborhood.

Check your Tri Taylor home's value or browse the current listings of tri taylor homes for sale below!



Latest Chicago - Tri-Taylor Homes for Sale

$575,000
3 Beds ⋅ 2 Baths ⋅ 12756472 MLS ⋅ NEW Status
Rarely available 3BR/1.5BA single-family home on a quiet Tri-Taylor cul-de-sac. This meticulously maintained property boasts high ceilings, central air, forced gas heating and hardwood floors. The gorgeous kitchen features stainless steel appliances and granite counters, flowing into a spacious dining area. Upstairs highlights 3 bedrooms and a full bath with a double vanity. The lower-level basement is the perfect space for a family room and provides ample space for additional storage. This home also comes with a full-size washer/dryer. The unbeatable outdoor oasis features a private fenced backyard and an oversized detached 2.5-car garage with a massive rooftop deck-perfect for entertaining! Highly desirable location offering an effortless commute. Walk to Taylor Street dining, UIC, Rush University Medical Center, CTA trains, and the Illinois Medical District. Welcome home!

929 S Bell Avenue, Chicago
$265,000
2 Beds ⋅ 2 Baths ⋅ 12749547 MLS ⋅ ACTIVE Status
Welcome to this spacious first-floor 2-bedroom, 2-bathroom condo in Chicago's highly sought-after Near West Side. Bright, comfortable and move-in ready, this home features beautiful hardwood floors and fresh paint throughout, creating a clean and inviting feel from the moment you walk in. The living room offers plenty of space to relax or entertain and features a cozy gas fireplace. The kitchen includes granite countertops, a breakfast bar, stainless steel appliances and recessed lighting. Both bedrooms are generously sized, with the primary suite offering a private retreat complete with a large closet and en-suite bath featuring a jetted tub and separate glass-enclosed shower. Additional highlights include convenient in-unit laundry and deeded parking in the rear lot. Ideally situated near the West Loop, UIC, Rush University Medical Center and the Illinois Medical District, with easy access to the Blue Line, CTA bus routes and I-290. Just minutes from the Loop, this is an excellent opportunity for both homeowners and investors looking for space, convenience and a prime Near West Side location.

2333 W Harrison Street Unit #1, Chicago
$849,900
9 Beds ⋅ 4 Baths ⋅ 12736859 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
$465,333
3 Beds ⋅ 2 Baths ⋅ 12617723 MLS ⋅ PRICE CHANGE Status
Charming single-family residence located in the heart of Chicago's Little Italy. This elegant home offers a spacious 2,000 square feet of living space, featuring three bedrooms and two bathrooms, making it perfect for comfortable, modern living. For Investors great as a local rental right here in the Medical District of UIC As you step inside, you'll be greeted by the warmth of beautiful hardwood floors that flow seamlessly throughout the ten well-appointed rooms. The inviting living area is highlighted by a cozy fireplace, providing a perfect spot for relaxation and gatherings. The home boasts southern exposure, ensuring every room is bathed in natural light throughout the day. The kitchen is complete with a delightful breakfast nook where you can enjoy your morning coffee. The open layout ensures effortless flow between the kitchen, dining, and living areas, ideal for entertaining. Convenience is at your fingertips with in-unit washer and dryer facilities, adding ease to everyday tasks. The home is equipped with 2 central air conditioning units and 2 forced air gas heat furnaces, ensuring comfort in every season. Descend to the full basement, offering ample storage space and endless possibilities for customization to suit your needs. FHA/VA ok! This property is a true gem, combining classic charm with modern amenities. Don't miss the opportunity to make this delightful house your home. Schedule a viewing today and experience all that 2242 W Taylor St has to offer.

2242 W Taylor Street, 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
$789,900
6 Beds ⋅ 4 Baths ⋅ 12694449 MLS ⋅ RE-ACTIVATED Status
Multiple offers received. Highest & Best due Sunday 8/16 by 5:00PM. Located in Chicago's vibrant Tri-Taylor medical district, 700 S Oakley Blvd is a rare and inviting multifamily property offering timeless character and exceptional versatility. The main building features two spacious units with beautiful original woodwork that adds warmth, charm, and classic Chicago appeal throughout. The property also includes a full basement with thoughtfully divided space, offering laundry facilities on one side and a recreation/craft area on the other-perfect for extra functionality and flexible use. Adding even more value, the property boasts a detached 2-car garage with a 2-bedroom coach house above, creating excellent opportunities for extended living, guest space, or rental income. Additionally, scenes from the hit series Chicago Fire were filmed in Unit 1, giving this one-of-a-kind property a memorable touch of local fame. Don't miss your chance to own this distinctive Chicago gem in a highly sought-after location near the medical district, downtown, and major transportation routes.

700 S Oakley Boulevard, Chicago
$675,000
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
$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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