View All Logan Square Chicago IL STR Income Homes Listings

8 Beds ⋅ 3 Baths ⋅ 12711586 MLS ⋅ CONTINGENT Status

Exceptional investment opportunity in the heart of Logan Square! Situated on charming tree-lined Lyndale Street, this legal three-unit building offers the perfect blend of classic Chicago character and modern functionality in one of the city's most sought-after and rapidly growing neighborhoods. Just a short walk to Logan Boulevard, the Blue Line, parks, and a vibrant mix of restaurants, cafes, and nightlife. Two units features 3 bedrooms and 1 full bathroom & 1 unit 2 bedrooms and 1 full bathroom making the property ideal for both investors and owner-occupants. Updated kitchens and bathrooms complement the building's original charm, while three separate HVAC systems (gas forced heat and central air) provide comfort and efficiency for every unit. The first-floor apartment has been successfully operated as a longer-term Airbnb-style rental catering to working professionals. All indoor and outdoor furnishings shown are included, allowing a buyer to seamlessly continue this proven income model. The remaining units are unfurnished and well-suited for traditional long-term tenants, offering flexible rental strategies and strong income potential. Additional highlights include expansive rear decks, common area laundry in the lower level, and two exterior storage units located beneath the rear stairwells. The rear yard features a full concrete pad, pitched and engineered to support the future addition of an upper garage structure, along with an existing gated parking area accommodating two cars. The rental potential for the three units and parking is approximately $8,500-9,000 per month. Meticulously maintained and thoughtfully improved, this property delivers outstanding comfort, functionality, and long-term value - a rare turnkey multi-unit opportunity in one of Chicago's hottest neighborhoods. Unit 2 currently rented for $3,500 per month & unit 3 for $3,100 per month.

2516 W Lyndale Street, Chicago

$815,000

6 Beds ⋅ 3 Baths ⋅ 12565177 MLS ⋅ CLOSED Status

Exceptional income-producing investment opportunity at the intersection of Bucktown and Logan Square. This all-brick, updated two-unit building-with an owner's duplex-down-has operated as a highly successful Airbnb for over 11 years, demonstrating consistent demand and strong returns. Both 3-bedroom units have been renovated over time and feature updated kitchens and bathrooms, central air, and gas forced heat. The well-maintained property offers two separate units with private entrances, maximizing rental flexibility and income potential. Ideal for investors seeking a proven short-term or long-term rental asset in the city. Refer to the updates and improvements sheet for full details. Property highlights include: Fully fenced lot with landscaped backyard and green space; rebuilt rear decks off both units, two-car garage (spaces rent approx $200 per month); numerous recent updates, making it move-in ready and low-maintenance. Utilities paid by tenants and both units are currently vacant, offering immediate leasing flexibility Located just steps from the Blue Line, residents enjoy acclaimed dining, boutique shopping, and vibrant nightlife across Bucktown, Logan Square, and Wicker Park. Quick access to I-90/94 ensures seamless connectivity throughout the city. This is a rare opportunity to secure a high-demand, income-producing property in one of Chicago's most desirable neighborhoods. See additional info tab with updates and improvements

2427 W Mclean Avenue, Chicago

$925,862

7 Beds ⋅ 3 Baths ⋅ 12564208 MLS ⋅ CLOSED Status

Legal 2-flat plus non-conforming studio, previously used as a short-term rental. Units consist of (2) three bed / 1 bath units with a small rear yard, two parking stalls off the alley, and updated with central air conditioning and common area laundry in the basement.The top floor unit is currently month-to-month and available for owner occupancy. Building has Prime Logan Square, a short walk to the Starbucks at Logan and California. Directly across from Haas Park, a 1.7 acre park which includes a 10,244 SF field house with a full gym, volleyball, basketball courts, and soccer fields. The park hosts movies in the park on summer nights as well as other community events. Rents for the 3-bedroom units are ~20% below-market at $2,350 and could be leased for $2,850.

2421 N Washtenaw Avenue, Chicago

$900,000

7 Beds ⋅ 4 Baths ⋅ 12489426 MLS ⋅ CLOSED Status

This gorgeous Logan Square two-flat is set on a beautifully landscaped oversized lot with a custom concrete patio and newer 3 car garage. The building has been lovingly updated by the current owners to include a fully renovated 2 bed 1 bath main floor unit with a finished 1 bed, 1 bath basement retreat that contains a sizable rec room/office with wet bar and a shared laundry room. The updated 2nd floor apartment has ample sunlight and living space, along with a renovated kitchen and bath, while the top floor in-law suite contains 2 bedrooms with an updated bath and kitchen area - both are currently occupied with annual leases. The property sits on a classic Chicago tree lined street with an updated front porch. Walk to the farmers market, bars, restaurants, coffee shops, grocery, two parks, and the Logan Square L stop. The top floor was previously listed as a successful short term rental and the bottom floor could allow the same flexibility if desired. Opportunities abound!

2706 N Monticello Avenue, Chicago

$701,000

3 Beds ⋅ 4 Baths ⋅ 12478639 MLS ⋅ CLOSED Status

**Multiple offers received. Highest and best offers due by 6 pm Monday, 9/29** Freshly-rehabbed 2 flat in booming Avondale with a charming finished studio in the attic! First floor unit features 2 beds and 1 bath with a beautifully-renovated kitchen and bathroom, rented through 5/31/26. Second floor is 1 bed/1 bath, currently owner-occupied and completely rehabbed including a magazine-worthy pantry off the kitchen. Finished attic is separately accessed through the rear stairwell and features a charming new kitchenette and full bath, perfect for working from home, hosting guests, or generating short-term rental income. A partially-finished basement provides yet more space for in-laws or a possible duplex with the first floor. Shared basement laundry plus a 2-car detached garage round out this spectacular, hard-working property. Short walk to Logan Square blue line station and all the dining, shopping, and culture that Avondale and Logan Square have to offer. Welcome home!

2952 N Wisner Avenue, Chicago

$730,000

6 Beds ⋅ 4 Baths ⋅ 12455699 MLS ⋅ CLOSED Status

Welcome to 3575 W Dickens Ave - Your new investment is a LEGAL 4 Unit building in the highly sought-after Logan Square neighborhood. Where do I start? This beautiful building has been renovated over the last year, it has newer electrical, newer plumbing, new roof, new flooring, new kitchens, new bathrooms, most of the windows are new, new siding, new grass, etc. The list goes on. 6 Total bedrooms & 4 bathrooms. As you enter the building you will find a studio apartment to your right with open concept living. Behind that unit you will find unit #2 that features 2 bedrooms. As you go up the stairs you will find 2 more units featuring 2 bedrooms each for a total of 6 bedrooms & 4 full bathrooms. Laundry room (hook ups) for the building located on the main level in the rear. Also features a big back yard with secure parking pad. Instant equity with this one & GREAT potential for rental income or SHORT-TERM rentals! Where else are you going to secure a move in ready legal 4 unit in Logan for under 800k? - Seller is Motivated

3575 W Dickens Avenue, Chicago

$1,300,000

10 Beds ⋅ 4 Baths ⋅ 12407303 MLS ⋅ CLOSED Status

FULL WALK THRU VIDEO OF BUILDING ON VORTUAL TOUR BUTTON. Brand new LEGAL 3 unit s/w CORNER Armchair investment in the Logan/Avondale area. (rental comps have building producing over 130k a year) Almost 5k sqft of above-grade sqft - no basement all above ground sft). Fully gutted - everything is new! 3 Massive units - all ready to go. All units have forced Air and Gas Heat - all kitchens brand new with dishwashers/micro/fridge/range, all units have their Washer and Dryers. All units are on their own gas and electric accounts. The owner pays for only water/common insurance and the electricity bill for common lights and garage power. First floor = 3 bed/Den/1 full bath. Unit 2 = 3 bed/1bth. Unit 3 = duplex unit 4 beds/2 full baths/large storage room. Common backyard - 2 car garage. Cap rate with all expenses and stabilized rent is over 8% on your money. It could also be a great owner-occupied with a regular monthly renter and 1 Airbnb unit. No deferred maintenance for a long time - perfect armchair or owner-occupied building or blended with short term rentals

2901 N Sacramento Avenue, Chicago

$695,000

6 Beds ⋅ 3 Baths ⋅ 12404222 MLS ⋅ CLOSED Status

Welcome to this beautifully maintained and thoughtfully upgraded single-family home located on the border of Logan Square and East Humboldt Park-just steps from the 606 Trail and Humboldt Park's sports fields, fishing lagoon, and inland beach! Offering nearly 2,700 sq ft of finished living space, this home is perfect for those seeking flexible living arrangements-ideal for multi-generational living, house hacking, a private guest suite, or short term rental. The main residence features four bedrooms and two full bathrooms, including two bedrooms and a full bath on the main level, and two bedrooms with another full bath upstairs. The recently remodeled main-level bathroom features timeless hexagon tile, subway shower tile, and elegant gold finishes. Upstairs, the primary suite offers a generous soaking tub with a rainfall showerhead, creating a relaxing, spa-like retreat. The main kitchen blends vintage charm with modern convenience, showcasing classic showcase cabinetry, granite countertops, stainless steel appliances, a walk-in pantry, and a reverse osmosis water system installed in 2024. You'll also find a dedicated dining room perfect for hosting, a bright and inviting living room, and a versatile den-ideal as an office, playroom, or fitness space. Flooring throughout the main level was recently updated in May 2025, adding fresh appeal. The remodeled garden-level suite, completed in 2020 with separate front and rear entrances, includes two bedrooms, one full bathroom, a full kitchen, living room, and den. The bathroom features a jacuzzi tub, and the largest bedroom includes a custom-built closet with pull-out shelving. The kitchen is beautifully updated with quartz countertops, a fish scale tile backsplash, stainless steel appliances, and its own reverse osmosis water system. This level offers tall ceilings, a functional layout, and a private feel-making it perfect for related living, guest accommodations, or a caregiver suite. A secure, shared laundry room is easily accessible to both levels and includes an extra refrigerator for added storage and convenience. Additional highlights include a two-car garage, a fully fenced backyard with new privacy fencing, and a spacious low-maintenance patio strung with charming lights-an ideal setting for outdoor entertaining or quiet evenings. The backyard is designed for ease, with no grass to maintain. There's also a workshop and storage area in the basement, attic storage above, and a new electrical panel. The home is equipped with a Nest thermostat for energy efficiency and peace of mind. Extensive upgrades have been made over the years, including new siding and exterior stairs in 2024, a new garage in 2018, a roof installed in 2016, updated windows, gate, fence, and patio in 2018, newly asphalted alley in 2025, and updated plumbing and electric systems in 2019. The furnace and AC were replaced in 2018, and the hot water tank was installed in 2019. Whether you're looking for flexible living options, income potential, or simply a beautifully updated home in one of Chicago's most dynamic neighborhoods, this property offers exceptional space, versatility, and comfort. Don't miss your chance to own this one-of-a-kind, move-in-ready home!

1659 N Francisco Avenue, Chicago

$840,000

5 Beds ⋅ 4 Baths ⋅ 12389329 MLS ⋅ CLOSED Status

Located in the highly sought-after Logan/Palmer Square neighborhood, this beautifully maintained legal 3-flat offers a fantastic investment opportunity! All three units have been fully remodeled within the last five years, featuring modern updates such as new plumbing, electrical systems, kitchens, bathrooms, and flooring. The building also offers brand-new siding and gutters for added peace of mind.The top-floor unit is currently rented long-term for $2,395/month and offers 2 bedrooms, 1 bath, plus a den. The middle unit is an income-generating 2 bed/1 bath, rented through Airbnb, while the garden unit (1 bed/1 bath) is listed on VRBO-providing both consistent rental income and short-term leasing flexibility.The property also includes a shared front patio, free laundry, extra basement storage, and exterior parking spaces for each unit. Situated in a vibrant neighborhood close to Logan Square and Palmer Square parks, trendy cafes, restaurants, and public transportation, this location is perfect for tenants seeking a lively community atmosphere.This is a turnkey investment opportunity with prime updates and a great location-don't miss out!

3406 W Dickens Avenue, Chicago

$372,500

3 Beds ⋅ 2 Baths ⋅ 12355819 MLS ⋅ CLOSED Status

This Palmer Square 3 bedroom / 2 bathroom condo is an absolute must see. Right on the boulevard! 1 deeded exterior parking spaced included in the price! With plenty of natural sunlight streaming in, you won't want to miss out on this unit. Located right on Humboldt Boulevard, in the heart of the Palmer Square neighborhood, you'll have easy access to all that Logan Square has to offer - bars, shops, restaurants and more! Not only that but it's also just a few minutes from Humboldt Park and the 606 Trail. This spacious layout has hardwood plank flooring throughout as well as modern kitchen appliances (GE/Whirlpool/Bosch). Plus it includes central heat/air-conditioning with Nest thermostat and a semi-private back porch for those summer days when you want to relax outside. There's even laundry in unit AND is a pet friendly building (cats/dogs allowed). Investor Friendly, Rentals Allowed. No Short Term / AirBNB rentals. Low Monthly HOA dues (water, scavenger, common insurance included). Jacuzzi tub in ensuite bathroom AS-IS.

1925 N Humboldt Boulevard Unit #1, Chicago

$1,078,750

7 Beds ⋅ 4 Baths ⋅ 12329475 MLS ⋅ CLOSED Status

An exceptional investment opportunity awaits in the highly sought-after Logan Square neighborhood with this classic brick 3-unit building. Perfectly blending charm, functionality, and income potential, this well-maintained property stands out in one of Chicago's most desirable communities. Each unit is bright and spacious, featuring high ceilings that create an open, airy atmosphere. The apartments include generous layouts with dedicated dining rooms, spacious living rooms, and abundant natural light throughout. The spacious kitchens in each unit offer an abundance of counter space and ample cabinetry-perfect for both everyday cooking and entertaining. Designed with functionality in mind, these kitchens provide plenty of room for meal preparation and storage.Three of the units offer two-bedroom plus den configurations-ideal for tenants needing extra space for a home office or guest room-while the fourth is a cozy one-bedroom unit. These versatile floor plans appeal to a wide range of renters, ensuring strong occupancy rates. The building is also an excellent option for owner-occupants, with the opportunity to live in one of the larger units while generating a steady rental income from the others. Good-sized bathrooms, central heating for year-round comfort, and convenient on-site laundry further enhance tenant satisfaction. Additional features include a two-car garage offering secure parking or extra rental income, a back porch area ideal for outdoor relaxation, and ample free street parking for guests. Location is key-and this property delivers. Just minutes from I-90, it's perfectly situated for commuters, and a short walk to the Blue Line adds even more convenience for public transit users. Residents will also enjoy proximity to grocery stores, gyms, cafes, entertainment venues, and the vibrant Logan Boulevard, renowned for its tree-lined streets, historic architecture, and strong sense of community. This Logan Square gem is a rare find with immediate income potential and long-term appreciation prospects. Don't miss your chance to own a versatile, income-generating property in one of Chicago's hottest neighborhoods!

2451 N Campbell Avenue, Chicago

$329,000

2 Beds ⋅ 2 Baths ⋅ 12323354 MLS ⋅ CLOSED Status

Your Creative Sanctuary in the Heart of Logan Square -- Welcome to your Logan Square landing pad - a garden-level retreat that balances community, creativity, and calm in all the right ways. At 2636 N Fairfield, Unit G, you're not just buying a home - you're stepping into a lifestyle: block parties and farmers markets, gallery openings and patio brunches, late-night tacos and early-morning coffee walks. It's the kind of neighborhood where individuality thrives - and this home mirrors that vibe perfectly. Inside, the open-concept layout creates a seamless flow between the living room and kitchen - ideal for hosting dinner parties, game nights, or impromptu wine tastings. The stylish breakfast bar invites casual conversations that turn into long, laughter-filled evenings. The primary bedroom is a serene, tucked-away sanctuary with dual vanities and a deep Jacuzzi tub - your own spa-like reset after a high-energy day. Need space to create, work, or welcome guests? The rear bedroom is perfect as a home office, studio, or bonus sleep space. Step outside and you'll find a semi-private patio that feels like a hidden garden, ready for morning coffees, solo journaling, or late-summer hangs with friends. Inside, a generous storage closet means your space stays as clean and calm as you want it to feel. You're in the Brentano School District, just steps from the school - offering access to a highly regarded public education option, whether you're planning ahead or looking to stay rooted in a vibrant neighborhood. Rentals are allowed (excluding short-term), giving you flexibility as your life and needs evolve. Whether you're a rising creative, a community-minded professional, or someone looking for a space that reflects the richness of Logan Square itself, this home is where your next chapter begins.

2636 N Fairfield Avenue Unit #G, Chicago

$312,500

3 Beds ⋅ 2 Baths ⋅ 12292577 MLS ⋅ CLOSED Status

Step into this spacious 3-bedroom, 2-bathroom corner unit in Logan Square, where comfort meets style. Situated on the second floor, this sunlit home enjoys north and west exposures, flooding the space with natural light. The open floor plan is perfect for entertaining, with a spacious kitchen that includes steel appliances, quartz countertops, and a tiled backsplash. Plus, enjoy your own outdoor patio directly accessible from the kitchen! The large primary bedroom features windows on three sides, ensuring a bright and airy environment with an en-suite bathroom. Two additional generous bedrooms and additional bathroom provide excellent separation, ideal for guests or a home office. Original hardwood floors extend throughout the unit, and ample in-unit closet space ensures all your storage needs are met. Convenient street parking is also available. This well-maintained, self-managed building offers peace of mind with strong reserves and recent updates. The location is unbeatable! You're just moments away from public transportation, trendy Logan Square and Palmer Square attractions, and an array of fantastic restaurants. Don't miss your chance to own this charming unit! (Laundry facilities and additional storage are available in the basement. No rental cap, but no short-term rentals allowed.

2123 N Saint Louis Avenue Unit #2, Chicago

$712,500

4 Beds ⋅ 2 Baths ⋅ 12223400 MLS ⋅ CLOSED Status

Turnkey 2-flat on the edge of Chicago's sought-after Bucktown and Logan Square neighborhoods. Gut-renovated in 2016 with no detail overlooked, this property offers both style and function, making it an exceptional opportunity for homeowners and investors alike. Currently operated as a successful Airbnb, this building is well maintained and a strong income-producer generating $89K in annual revenue (7.7% CAP after expenses). Each of the two units feature 2 bedrooms and 1 bathroom, with thoughtful updates and finishes that appeal to today's renters and short-term guests. From sleek kitchens and baths to a meticulously clean basement/foundation, the quality of the renovation shines through every space. Just off Logan Blvd, this location is close to some of the city's best dining, shopping, and entertainment. Whether you're looking to invest or live in one unit while renting out the other, 2505 N Artesian Ave is an unparalleled opportunity in one of Chicago's most dynamic areas.

2505 N Artesian Avenue, Chicago

$370,000

2 Beds ⋅ 2 Baths ⋅ 12067053 MLS ⋅ CLOSED Status

* Check out the video & the 3D tour of this home * Stunning & unique 2 bedroom, 2 bathroom condo in prime WEST BUCKTOWN/LOGAN SQUARE location, just one block from the 606! This updated unit overlooks the tree-lined street, is one of the largest of the complex, and has the perfect mix of charm & modern updates. Step into this unit and enjoy the sunny & open layout with natural hardwood floors throughout and a wall of windows that bring in lots of natural light. Condo living at its best, this unit has a European-style kitchen with German appliances, including a built-in refrigerator/freezer and dishwasher, and a large granite island with a waterfall edge with custom island dining extension crafted with reclaimed walnut hardwood. The main living space offers flexibility, with a nook ideal for a dining table. Both bedrooms in this unit are nice-sized with ample closet space. The bathrooms boast a modern look with custom tile in each. The first bathroom has a jacuzzi tub, and the second bath has a floating vanity and stand-up shower. A large in-unit laundry room with extra storage space makes housework super convenient. The shared deck off the mud room is perfect for relaxing and enjoying a drink outside after getting your fill from the booming restaurant scene mere blocks from the condo. Additional features include forced-air heating, central air, and a large assigned storage area in the rear common space. Several recent updates include: complete floor to ceiling new paint throughout the unit (2023), New recessed can lights in living/hallway (2024), new custom kitchen island (2023), new Bosch Dishwasher (2023), new standing desk/Elfa storage (2023), Roof repair/replacement (2021), Spot tuckpointing (2021) - Please ask your agent for the full list of improvements to the unit and the building. HOA assessment of $492 per month includes water, common insurance, exterior maintenance, garbage, and snow removal. Easy street parking and permit parking. Professionally managed HOA with extremely healthy reserves: $34,847 (Reserves) and $32,881 (Operating). No special assessment. All BRICK building; gut rehabbed in 2005. 15 total units. Rentals allowed, no short-term rentals. Cats & dogs allowed. Max 2 pets. Pets can't exceed a combined weight of 50 lbs. Fall in love with all that West Bucktown & Logan Square have to offer - Extremely walkable to transit (Western Blue Line train stop & bus stops), popular restaurants/bars/retail, coffee shops, 606 trail, abundant green space, and easy highway access. Welcome home!

1655 N Fairfield Avenue Unit #201, Chicago

$325,000

3 Beds ⋅ 3 Baths ⋅ 12041098 MLS ⋅ CLOSED Status

HUGE LOT and INVESTMENT OPPORTUNITY a few lots in from The 606 Trail. This single family home is on an almost 180 foot deep lot! Dreamy outdoor garden space potential and walking distance to restaurants, Humboldt Park, and beautiful green streets. On the main level there are 2 bedrooms, one bath, a living room and a gigantic kitchen with bonus area on the rear with hardwood floors in most of the space. The 2nd level features a light and bright in-law arrangement with private rear entrance, 1 bedroom and closet, a living area, a 2nd kitchen, dining area and bath. There is also another in-law arrangement in the basement with another full bath, living area, two sleeping areas, and a kitchen with private front entrance and addtl rear entrance. There is a shared laundry room in the basement with 2 electric meters. Building features radiator heat and a more recently updated hot water heater. 2.5 car garage features a new electric garage door and 3-year new roof. Main building also features a 3 year new roof. A large deck serves as entrance to all upper levels on the rear of the home. Front and rear yard are fully fenced. Live on one floor and rent other spaces or use as short term rentals. Building needs some renovation. Or tear down and build new on this amazingly large lot. Sold As-Is. All levels need work and rehab. This is a project property. Month-to-month tenants in both basement and 1st floor.

1828 N Saint Louis Avenue, Chicago

$235,000

2 Beds ⋅ 2 Baths ⋅ 12033074 MLS ⋅ CLOSED Status

Attention Investors!! Unit leased through spring 2025. Beautiful, extremely sunny, updated vintage 2 bed, 2 Bath in hot Logan Square/Avondale. Easy to rent unit in professionally managed building with no rental restrictions (no short-term or air bnb). Unit features contemporary kitchen and baths including ensuite full bath. Great condition hardwood floors throughout. Oversized steel patio in rear redone in 2018. Major tuckpointing and maintenance projects done 2018. Well kept building with healthy reserves. Long term tenants signed through spring 2025.

3100 W Diversey Avenue Unit #2N, Chicago

$1,125,000

3 Beds ⋅ 4 Baths ⋅ 11911292 MLS ⋅ CLOSED Status

This young home is a marvelous amalgam of unrivaled location and beautiful, high quality construction. It's got Hardie panel siding throughout, and timelessly elegant finishes that include recessed panel cabinetry, quartz countertops, BlueStar fridge, Thermador range, full height Vinotemp beverage fridge, hardwood floors, and more. It is modern yet transitionally appointed, opening up countless options for wall art, creative lighting and paint hues aplenty! 3,000+ square feet over 3 levels, warmed and cooled by 2 furnace and a/c systems, all are planned perfectly for short term guests or long term enjoyment throughout the year. The roomy deck overlooks the gorgeous green yard which extends well beyond on its way to the 2-gar garage. The location, serene green and conveniently cozy, is tiny steps from everything that is important about Logan Square - the el and multiple easy downtown routes. the lush boulevard, the farmer's market, the incredible eat and drink spots including Reno, BiXi, Longman, New Wave, Saba and beyond!

2906 N Albany Avenue, Chicago

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