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$449,000
6 Beds 3 Baths 12734070 MLS CONTINGENT Status
Beautifully updated two-unit building in Chicago's desirable Woodlawn neighborhood, offering an excellent opportunity for both investors and owner-occupants. This well-maintained property features spacious units, modern updates, and flexible living arrangements. The duplexed-down main-level unit offers 4 large bedrooms and 2 full baths, while the upper-level unit features 3 bedrooms and an updated full bath. Both units offer bright, inviting living spaces, generous bedrooms, ample storage and renovated finishes throughout. The refreshed eat-in kitchens feature breakfast nooks, newer cabinetry, modern quartz countertops, stainless-steel appliances, and custom tiled backsplashes creating a clean, contemporary feel. Large windows fill the units with natural light, while updated flooring throughout adds to their move-in appeal. Classic Chicago architecture blends seamlessly with modern updates, creating a property that is both charming and practical. Ideally located near public transportation, parks, shopping, restaurants, and major roadways, this property provides convenient access to surrounding neighborhoods and downtown Chicago. Its proximity to the University of Chicago, Jackson Park, and the Obama Presidential Center further enhances its appeal. Whether you're looking to expand your investment portfolio or live in one unit while generating rental income from the other, this versatile property is an opportunity worth exploring.

7026 S Eberhart Avenue, Chicago

$325,000
5 Beds 3 Baths 12734579 MLS CONTINGENT Status
Exceptional investment opportunity in Chicago! This solid brick, 3-unit building is ready for its next chapter and offers tremendous potential for investors, developers, or owner-occupants willing to bring some TLC. Situated on an oversized corner lot, this classic Chicago 2-flat, plus garden unit, enjoys a convenient location just steps from the vibrant 26th Street corridor and close to schools, shopping, dining, CTA transportation, and expressway access. The property features 3 residential units, extra storage in the basement offering additional possibilities, and a detached 2-car garage for added convenience and value. While the building needs some extra love, its solid construction, desirable multi-unit configuration, generous lot, and established location provide an excellent foundation for a thoughtful rehab. Bring your vision and transform this well-located building into a standout investment!

4134 W 25Th Place, Chicago

$899,000
9 Beds 6 Baths 12736649 MLS ACTIVE Status
Discover timeless Chicago architecture in this stately three-unit greystone located in the heart of Bronzeville. Showcasing the distinctive Romanesque style-one of Chicago's most recognized architectural traditions-this classic building blends historic character with modern convenience. Each spacious residence features 3 bedrooms, 2 full bathrooms, and a separate formal dining room offering generous living space ideal for both everyday living and entertaining. The thoughtfully designed interiors include hardwood floors, soaring ceilings, in-unit laundry, and abundant natural light. Spacious kitchens are appointed with granite countertops, ample cabinetry, and room for a breakfast table or casual dining. Each unit is separately metered and equipped with its own furnace and water heater, providing convenience, efficiency, and simplified property management. The first and second-floor units are occupied by long-term tenants, providing immediate, stable rental income. The third-floor unit is currently vacant, presenting an ideal opportunity for an owner-occupant to move right in while benefiting from rental income, or for an investor to lease the unit and maximize the property's income potential. Step outside to enjoy brand-new rear porches, providing each unit with a private outdoor deck. The property also features gated parking with one dedicated parking space for each unit, offering added convenience for residents. The full basement provides additional value with the potential to create an additional dwelling unit or expand the property's existing living space. Situated on a picturesque tree-lined street, this exceptional investment or owner-occupant opportunity is just minutes from public transportation, neighborhood parks and green spaces, and the vibrant dining, shopping, and cultural attractions of nearby Hyde Park and South Loop. Whether you're looking to expand your investment portfolio or own a piece of Chicago's architectural heritage, this exceptional Bronzeville greystone offers the perfect blend of historic character and modern amenities. Enjoy stable rental income or sell later as individual condos. An outstanding opportunity for both investors and owner-occupants.

4408 S Michigan Avenue, Chicago

$949,900
4 Beds 4 Baths 12735514 MLS CONTINGENT Status
Perfect updated 2 flat on a tree lined street in the heart of Andersonville! Top floor unit was completely reconfigured and renovated by the current owner to include a massive sun filled great room, 2 beds, and 2 baths. Stunning custom kitchen with stainless appliances, great storage, and additional dry bar! Top floor has newer HVAC, In Unit Laundry and hardwood flooring throughout! Primary suite with dressing area and ensuite bath featuring oversized vanity, and huge walk in shower with glass surround! First floor 2 bed plus den, 1.1 bath unit with generous public rooms, kitchen with great storage and stainless appliances, opens to eating area/ sitting room. First floor unit also has central HVAC, and private laundry in the basement. Enclosed rear stairs to great landscaped yard! 1.5 car garage with plenty of space for a 2 car garage if needed. Extensively updated and well maintained by the current owner, the building provides a unique and flexible asset with room for considerable upside with full basement! Seconds to the best of Clark Street restaurants , and transportation including Metra! Must See!

1633 W Olive Avenue, Chicago

$130,000
8 Beds 3 Baths 12737206 MLS ACTIVE Status
Great opportunity to complete and customize this spacious West Garfield Park multi-unit property. Major improvements have already been started, with several rooms featuring fresh paint, updated windows, and new finishes, while additional renovations remain to unlock the property's full potential. The home offers generous living space, large bedrooms, a full basement for storage or future expansion possibilities, and a fenced yard. The upper level showcases significant progress, while the main level, kitchen, and bathrooms provide an excellent opportunity for a buyer or investor to finish to their own specifications. Whether you're looking to renovate and occupy, add to your investment portfolio, or create long-term rental income, this property presents tremendous value with much of the heavy lifting already underway. Conveniently located near parks, schools, public transportation, and expressways. Sold as-is. Bring your vision and finish this promising project.

4150 W Carroll Avenue, Chicago

$465,000
9 Beds 4 Baths 12728571 MLS PENDING Status
Spacious brick three-flat offering three 3-bedroom apartments, a partially finished basement with an additional bathroom and a 3-car detached garage. Two units are currently occupied, while the vacant third-floor apartment provides an excellent opportunity for an owner-occupant or investor seeking additional rental income. Numerous capital improvements have been completed, including replacement of the original boiler with three individual gas forced-air furnaces, upgraded electrical wiring, extensive plumbing improvements featuring copper supply lines with individual unit shutoff valves, a newer 75-gallon hot-water tank and separate gas and electric meters for each apartment. A fourth gas meter serves the building's common utilities. Additional updates include vinyl flooring throughout all three apartments, newer windows throughout much of the building, recent roof maintenance, garage repairs and a replaced main water shutoff valve. Each apartment features three bedrooms with separate living and dining rooms. The partially finished basement provides additional storage and utility space. With spacious units, separate mechanical systems and meaningful infrastructure improvements already completed, this property offers flexibility for owner-occupants and investors alike. Schedule your private tour today.

7841 S Wolcott Avenue, Chicago

$869,000
7 Beds 3 Baths 12736110 MLS CONTINGENT Status
Welcome to 2323 W. Charleston - a fantastic Bucktown opportunity with incredible potential! This spacious 2-flat offers great bones, a flexible layout, and an oversized dormered attic featuring a full bath and multiple skylights. While the property needs work, the possibilities are endless and the property is ideally suited for a single-family conversion or an investor looking to create value in one of Chicago's most desirable neighborhoods. The property also offers a unique no-setback configuration, creating the opportunity for a generous yard area between the building and garage. Located just steps from Holstein Park, with easy access to neighborhood restaurants, shopping, transportation, and all that Bucktown has to offer. Bring your architect, contractor, and vision-this is a rare opportunity to transform a property with tremendous upside into something truly special. Easy to show!

2323 W Charleston Street, Chicago

$799,999
6 Beds 3 Baths 12734609 MLS CONTINGENT Status
2826 W. Wellington Ave. is a well-maintained, brick, 3-unit, residential asset located in the heart of Chicago's desirable Avondale neighborhood. The property consists of three spacious 2-bedroom, 1-bathroom floor plans, offering investors a low-maintenance asset with immediate rental upside and no near-term capital expenditure requirements. The property features strong mechanical infrastructure, including newer individual HVAC systems and dedicated hot water heaters for each unit. Unit finishes vary, highlighted by a high-end "owner's unit" on the ground floor that provides premium finishes and immediate flexibility for an owner-occupant or top-of-market rental rates. The "owner's unit" was previously converted from 3-bedrooms to 2-bedrooms, and could easily be converted back to 3-bedrooms. All units are fully equipped with in-unit laundry. Additional value-add potential exists with the detached garage, currently owner-utilized, which can be leased to existing tenants or neighborhood residents for an estimated $250/month. Previously owner-occupied, this property represents an ideal turn-key opportunity for an investor seeking stable cash flow, low operational friction, and clear path to increase the gross income. Located steps from key transit options, residents enjoy fast access to the CTA Blue Line (Belmont and Logan Square stations) and I-90/94 (Kennedy Expressway), along with the vibrant retail and dining corridors along Milwaukee, Belmont, and California Avenues.

2826 W Wellington Avenue, Chicago

$569,000
3 Beds 2 Baths 12735726 MLS ACTIVE Status
WOW! amazing Well-maintained legal 2-flat in desirable Portage Park! Come see the classic charm of this 2 unit that has stained glass, built-ins original woodwork with crown molding. Also features forced heating and Central air for both units which is rare for this type of buildings The main floor has all beautiful hardwood floors, a spacious Spacious living room, formal dining room, also has additional sunroom that was finished and insulated which can be used for Den or Office! 1st floor has eat in kitchen with back porch that can be used for extra storage. The bright second-floor unit features large kitchen formal living and dining rooms all hardwood floors. Bathroom features beautiful bath tub and standup shower! Each unit has a separate forced air furnace and AC unit along with its own hot water heater! Outside, you'll find a good-sized yard with plenty of green space along with garage with o the yard-perfect for outdoor entertaining and gatherings. Building has all newer windows copper plumbing mechanicals are in good shape as well. This corner 2 unit is on a great block Conveniently located near shopping, public transportation, restaurants, parks, and more.

5258 W Dakin Avenue, Chicago

$479,900
5 Beds 2 Baths 12731426 MLS CONTINGENT Status
Set on a great residential street, this classic 2-flat offers the character that people want with the flexibility that investors and homeowners appreciate. Each of the two apartments are complemented by enclosed porches, wood accents and beautiful floors. The kitchens are well sized so they can accommodate a table and have a walk-in pantry. The finished attic provides an exciting opportunity for future expansion and may be able to add additional living space which is an attractive value add. The building is conveniently located near public transportation, shopping, schools and the expressway which offers easy access to everyday amenities. The building is currently occupied and being offered As-Is. This is an excellent opportunity for a homeowner or investor that is ready to acquire a great building. Call today to schedule a tour.

2720 N Monitor Avenue, Chicago

$1,050,000
8 Beds 4 Baths 12735942 MLS CONTINGENT Status
Ideally located just steps from Humboldt Park, this rare income property features an oversized all-brick building on an extra-wide and extra-deep 30 x 130 lot in one of Chicago's most dynamic neighborhoods, where rents are surging and investment momentum continues to accelerate. This fully leased investment property generates $107K in annual rent delivering strong, reliable cash flow from day one. All units have been extensively renovated within the last 2-7 years, featuring modern kitchens and baths, drywall, copper plumbing, and conduit electrical. Two front units boast fantastic private balconies, while two rear units feature enclosed porches that are ideal for additional storage or flexible living space. All four conforming, have separated utilities, gas forced-air heat, and central AC, & are fully leased. The garden unit is a value-add opportunity. Three-car parking pad on-site, with one space currently unrented allowing for easy additional income. Strong Cash Flow, Quality Bones, & Highly Renovated. This is a rare opportunity to own a high-performing asset in a corridor with genuine momentum, before the market catches up.

3245 W Division Street, Chicago

$250,000
8 Beds 3 Baths 12735976 MLS ACTIVE Status
**Multiple offers received. H/B due by 4:00PM on 8/20/2026.** Attention developers and investors: SHORT SALE opportunity in North Lawndale. Unlock the potential of this legal 3-flat with tons of upside. Each unit features 3 bedrooms and 1 full bath, 9' ceilings and hardwood floors. A full, unfinished basement offers future expansion potential. This building is situated on an oversized lot, with plenty of space for a garden, a playset a storage shed or just some extra elbow room. With the right vision, an experienced rehabber can create an oasis in the heart of the city. Easy access to public transit at Roosevelt and Pulaski. Close to I-290. Renovated three bedroom apartments are fetching $1800-$2000/month. ARV $515,000 based on recent sales within half a mile of this property. Seize this chance to own an all-brick, legal 3-unit on a huge lot before it's gone!

3943 W 14Th Street, Chicago

$875,000
6 Beds 2 Baths 12735632 MLS CONTINGENT Status
Welcome to this beautifully renovated grey stone at 3329 W Pierce, offering classic Chicago charm paired with thoughtful, move-in-ready updates. This turnkey property is ideal for an investor or an owner-occupant looking for strong rental income alongside their own comfortable unit. The top floor unit features 3 generously sized bedrooms and 1 full bath, with a bright, open living and dining layout framed by elegant bay windows that flood the space with natural light. Rich hardwood floors run throughout, complemented by high ceilings and classic millwork that speak to the building's vintage character. The updated bathroom is a standout, with floor-to-ceiling subway tile, a marble accent band with black tile detailing, and a striking black-and-white hexagon custom mosaic floor - a timeless design that never goes out of style. Each bedroom offers comfortable proportions and ample closet space, and the unit's layout flows easily from the front entry through the living and dining rooms to the eat-in kitchen, with direct access to a private extra-large outdoor deck - perfect for morning coffee or evening relaxation. The first floor unit includes two bedrooms and one bathroom with all of the same amazing finishes and amenities as the top floor. The fully finished garden unit (Non-Conforming) offers a spacious studio with an enormous bathroom and walk-in shower, high end stone, custom tile, and radiant heated floors. The kitchen is incredibly cool with reeded wood paneling, natural stone counters/backsplashes, and moody lighting, ideal for owner occupancy, extended family, or additional rental income. Additional improvements include a brand new oversized 2-car garage, extra-large outdoor decks for both upper floor units, basement storage space, community laundry, and a work area with built in tool bench. Outside, the property is fronted by a custom cedar privacy fence and gate with wire mesh trellises and planters, creating a private grotto with established handsome greenery. The building includes a dedicated multi-unit mailbox setup, offering the ease and functionality of a well-managed investment property. Located on a quiet, tree-lined residential block with easy access to Humboldt Park, the 606 trail, dining, and transportation. A rare opportunity to own a piece of Chicago's architectural history with all the modern comforts already in place - nothing to do but move in and enjoy.

3329 W Pierce Avenue, Chicago

$364,999
8 Beds 2 Baths 12735939 MLS CONTINGENT Status
Step into a classic 1898 Chicago Greystone, ideally situated in the evolving North Lawndale neighborhood just west of Douglas Park, between Roosevelt and Douglas Blvd. This area is seeing exciting revitalization-Inside, both units offer a layout with formal living room and dining room, hardwood floors. The first-floor unit features 4 Bedrooms and is currently rented month to month. Upstairs, the second unit has 4 Bedrooms and is currently rented on a fixed lease. Recent updates include new hot water tanks for both units and individual forced-air heating systems, offering convenience and independence for each space. The unfinished basement opens the door to future possibilities-whether you envision a duplex-down for added living space or a separate finished area for additional rental income. 2 parking spots on the back parking pad, new fence was recently installed. A new roof was installed 2 years ago. With both front and rear access, the potential here is easy to imagine. A location that keeps you connected-close to CTA lines, I-290, the Illinois Medical District, UIC, Pilsen, the West Loop, and downtown. A property with character, flexibility, and upside in a neighborhood on the rise-come take a look and see how it fits your vision.

1418 S Saint Louis Avenue, Chicago



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