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$2,400,000
9 Beds 5 Baths 12764691 MLS NEW Status
Rare opportunity to own a distinguished four-flat in the heart of Chicago's coveted Old Town Triangle. Built in 1894, this architecturally significant brick building showcases remarkable historic character, highlighted by its steamboat Gothic front porch featuring turned balusters, decorative spindles, cast iron railings, and an elegant limestone facade adorned with festoons beneath the windows. The property consists of four well-appointed units, including a spacious owner's residence offering 3 bedrooms, 2 bathrooms, and private outdoor space. Three additional units feature oversized two-bedroom layouts. A large lower level provides abundant storage and includes shared laundry facilities. One garage parking space completes the offering. Nestled on a picturesque, tree-lined street in the idyllic Old Town Triangle neighborhood, this exceptional property presents multiple opportunities for investors, owner-occupants, or those seeking to convert the building into a spectacular single-family residence. A rare blend of historic charm, income potential, and premier location.

230 W Saint Paul Avenue, Chicago

$1,100,000
8 Beds 6 Baths 12760990 MLS NEW Status
Excellent investment opportunity in the heart of West Town! This fully occupied 4-unit property features two units in the front building and two additional units in the rear coach house. Each spacious unit offers a functional 2-bedroom layout, along with granite countertops, stainless steel appliances, generous room sizes, and convenient in-unit laundry. Ideally located near public transportation and surrounded by West Town's restaurants, shopping, and neighborhood amenities. With all four units currently occupied, the property offers immediate rental income while also presenting a great future opportunity for an owner-occupant looking to live on-site while generating income from the remaining units. A versatile addition to any investment portfolio in a highly desirable Chicago neighborhood.

1464 W Ohio Street, Chicago

$900,000
4 Beds 4 Baths 12761589 MLS NEW Status
2418 N Western Avenue is a well-configured four-unit property located in the heart of Bucktown. The property features three units in the front building plus a detached coach house in the rear, offering four separate 1-bedroom/1-bathroom units. Each unit is separately equipped with its own HVAC system, hot water tank, and electric panel. The property also features common-area laundry located in the basement of the rear coach house, along with one exterior parking space accessible from the alley. Rents are currently below market, providing meaningful upside for a new owner. The four units currently generate an average rent of $1,756 per month compared to an estimated market average of $2,300 per month. Unit 2F is currently in the process of moving out, creating an opportunity for an owner-occupant or investor seeking flexibility. Ideally situated at the convergence of Bucktown, Logan Square, and West Lakeview, 2418 N Western Avenue offers convenient access to the Western Blue Line station, expressway, and multiple bus routes. The property combines strong neighborhood connectivity with immediate rental upside and a flexible four-unit configuration.

2418 N Western Avenue, Chicago

$1,599,900
9 Beds 4 Baths 12758652 MLS NEW Status
Introducing 3208 North Seminary tucked into the heart of Lakeview, just a block from the Belmont CTA and a short walk from Wrigley Field and the energy of Clark Street, this four-unit building with a two-car garage sits where renters want to live. It has had the same owner since 2002 and it shows. Every unit has been fully renovated in the last ten years with hardwood floors, granite countertops and porcelain-tiled baths, and the updates have kept coming, including new windows, LED lighting, electronic entry locks, and new furnaces, A/C units and appliances in 2024. Two 3-bedroom units, a renovated 2-bedroom duplex and a garden 1-bedroom each have their own heating, cooling and hot water, which keeps the owner's costs low. The building is fully leased through June 2027 and brings in $139,674 a year against just $24,547 in expenses, for a 6.57 cap rate at $1,600,000. Rents are still below market, with about $11,400 a year in upside, and the building has stayed full anyway. That gives an investor steady income today and a clear path to more as the leases come up.

3208 N Seminary Avenue, Chicago

$1,349,000
6 Beds 4 Baths 12750888 MLS ACTIVE Status
Like brand new construction full brick 2-Flat BUT WITH 4-Legal units at the WORLD district of Devon Ave./California Ave., totally LIKE brand-new interior and exterior with quality work delivery including gourmet kitchens featuring granite counter-tops, quality cabinets with S.S. appliances, bathrooms, hardwood floors and beautiful brand-new decks out of the kitchen. High efficiency individual utilities include new central air, electric and plumbing including E.J. pump and sump pump. High basement ceiling with full 8'. Owned coin laundry room, 8-parking tandem spaces for additional income. Front and back security cameras along with all digital public entrance doors on electronic locks. Walking distance to public transportation, retailers, and restaurants, daily life necessities, minutes to major roads, Lake Shore Dr., northwest suburbs, and interstates. Strong investment area opportunity Fully leased.

6336 N Fairfield Avenue, Chicago

$950,000
10 Beds 4 Baths 12751982 MLS ACTIVE Status
4-UNIT MULTIFAMILY INVESTMENT OPPORTUNITY FEATURING 10 BEDROOMS AND 4 BATHROOMS WITH ESTABLISHED RENTAL INCOME. EXTENSIVE RENOVATIONS AND IMPROVEMENTS COMPLETED IN 2021-2022, INCLUDING NEW WINDOWS AND WINDOW LINTELS, UPDATED ELECTRICAL SERVICE WITH INDIVIDUAL CIRCUIT BREAKERS FOR EACH UNIT, ALL-COPPER PLUMBING, HIGH-EFFICIENCY HVAC, AND INDIVIDUAL 40-GALLON POWER-VENT WATER HEATERS. ADDITIONAL IMPROVEMENTS INCLUDE HARDWOOD FLOORING, UPDATED KITCHENS WITH GRANITE AND QUARTZ COUNTERTOPS, FENCING, REAR PORCH, CONCRETE WORK, AND AN UPDATED MAIN ENTRANCE. CLEAN BASEMENT WITH POTENTIAL FOR FUTURE USE, SUBJECT TO ZONING AND APPROVALS. WELL-MAINTAINED, SUBSTANTIALLY IMPROVED PROPERTY WITH MULTIPLE INCOME-PRODUCING UNITS AND LONG-TERM INVESTMENT POTENTIAL.

6950 S Indiana Avenue, Chicago

$999,999
7 Beds 4 Baths 12749567 MLS ACTIVE Status
Fantastic investment opportunity in highly sought-after Noble Square/East Village! This solid brick 4-flat offers a full basement with laundry, 2-car garage plus an additional parking pad, and four fully occupied units with month-to-month tenants. The property features one 1-bedroom/1-bath unit and three spacious 1-bedroom + den/1-bath units. Tenants pay their own utilities, with each unit featuring individual gas heat, window A/C units, and a dedicated hot water tank located in the basement. Currently 100% occupied with rents below market, offering excellent potential for increased rental income. Units have historically rented quickly, making this a great opportunity for investors looking to add a well-located, income-producing property to their portfolio!

1433 W Superior Street, Chicago

$1,200,000
5 Beds 5 Baths 12644332 MLS ACTIVE Status
HOT WEST TOWN Multi-Family 4 Unit Property- separate front brick facade building featuring 2 units plus a garden unit (Non-conforming garden unit-with no representation of legality of garden unit) and a separate rear building offering an additional 2 one bedroom, one bath units with hardwood floors, all units have Individual Space Heat. Coin-Operated Common Area Laundry Facility. Additional room, and water closet in the lower level for the owner's personal use only. Nice deck in yard, 2 rear parking spaces with privacy gate. Immediate income increase by renting the 2 parking spaces. Easy access to public transportation, just steps to the blue line, grocery stores, convenient highway access, popular restaurants, entertainment, and minutes to River West, Fulton Market and downtown. Build your dream home, hold for long term investment, 1031x, offers R3 zoning. Many possibilities.

1542 W Thomas Street, Chicago

$1,200,000
11 Beds 7 Baths 12726785 MLS ACTIVE Status
Turnkey cash flowing Rarely Available 4 Flat Building Located in prime East Woodlawn desirable community just steps from Obama Presidential Library, University of Chicago Campuses including Medical School, Law School, University of Chicago Hospital, Charter School, Museum of Science and Industry, Chicago Theological Seminary, Mount Carmel High School, Lake Michigan, Grocery Stores, Multiple Eatery's including the South Shore Cultural Center. A true gem for investors and or owner occupant alike. The 3 above ground oversized units each feature 3 bed/2 Full baths configurations & 1 lower level features an oversized 2 bed 2bath configuration. Property features new interior upgrades such as Copper Plumbing infrastructure, Electrical infrastructure, HVAC infrastructure and drywall. Open floorplan concept layout within each unit with the top floor unit giving a penthouse vibe. Kitchens positioned in the front of each unit 42' Maple shaker style cabinets, granite & laminate countertops, stainless steel appliances & recessed lighting. Meticulously preserved & refinished woodwork architecture & hardwood flooring in the property was blended with new upgrades to keep the charm & character of this historic property. Exterior upgrades include new vinyl windows, concrete parking pad with rear wrought iron gated fence, front wrought iron gated fence with intercom system, treated wood The lower level was renovated by excavating the floor & creating higher head space & upgrading to a new sump pump rainwater drainage system & concrete slab. The property shares a common area laundry with washer/dryer owned by Landlord. Each unit is individually metered & has separate HVAC & Hot Water Heater tanks.

6638 S Woodlawn Avenue, Chicago

$985,000
8 Beds 4 Baths 12742505 MLS ACTIVE Status
NEW & IMPROVED in the heart of Pilsen! This legal 4-unit property which includes a coach house and 2-car garage is back on the market with meaningful improvements, refreshed units, improved pricing, and an even stronger overall package for both owner-occupants and investors. Since its previous offering, the property has benefited from additional improvements including tuckpointing, unit refreshes, and an updated owner's duplex that now offers 3 bedrooms and 1 bath creating an even more attractive live-in opportunity. Another significant improvement: the property taxes now reflect the Homeowner Exemption, reducing the tax bill from approximately $14,000 to under $9,000. All units feature separate utilities, with in-unit laundry in the owner's duplex and a common laundry area serving the remaining units. The combination of multiple units, a coach house, and a rare 2-car garage provides tremendous flexibility for an owner-occupant looking to offset housing costs or an investor seeking a well-located multifamily asset. Conveniently located near the CTA Pink Line at 18th Street with direct access to the Loop, multiple bus routes along 18th and Ashland, and easy connections to I-290, I-90/94, and I-55. Proximity to the UIC Medical District, along with Pilsen's restaurants, shops, arts, and neighborhood amenities, adds to the property's long-term appeal.

1527 W 18Th Place, Chicago

$950,000
8 Beds 4 Baths 12731559 MLS ACTIVE Status
Attention, attention! This solid brick 4-unit building offers an excellent owner-occupant or investment opportunity. Each unit has its own boiler, with tenants responsible for their individual heating costs. All four units have been updated and feature in-unit washers and dryers. Water hater, furnace and roof are newer. Two bathrooms have been renovated, The property has been exceptionally well cared for and the full unfinished basement provides potential for additional storage or future expansion, subject to applicable approvals. The property also includes three rear parking spaces. One unit is currently vacant (listed for rent) and has been fully rehabbed, making it ideal for an owner-occupant to move right in. With rental from the other three units, an owner-occupant has the potential to significantly or potentially cover-their mortgage and living expenses.

4112 W Wellington Avenue, Chicago

$1,099,000
9 Beds 4 Baths 12728301 MLS ACTIVE Status
Well maintained 4 flat in the middle of UIC area. Great short street with Arrigo park at the end of the block. Three units are occupied and one is intentionally left vacant for new owner. Three occupied units have leases expiring July, 2027. The 3rd floor will expire July 31, 2025 after a $50 rent increase effective 8/1/24. Units are in very good condition with SS dishwashers, refrigerators, stoves, over range microwaves and 3 units have washer and dryers in unit. There is an existing garage structure that no longer has alley access, so it is essentially a large shed, work area, other - it has lots of potential (possibly a 5th unit). Four water heaters and 4 forced air furnaces (2 with central air). Roof was a tear-off and replaced in 2014 by Reed Roofing.

708 S Ada Street, Chicago

$1,450,000
7 Beds 7 Baths 12705248 MLS ACTIVE Status
Rare opportunity to own a turnkey, legal all-brick 3-flat in the heart of Chicago's highly-coveted Bucktown neighborhood. Perfectly suited for an investor looking for premium rental yields or an owner-occupant looking to live in one unit while letting three others pay the mortgage. Each of the three spacious units features a highly rentable 2-bedroom, 2-bathroom layout, complete with central air, and abundant natural light. Originally rehabbed in 2002, the building has been meticulously maintained and upgraded: Decks and Porches were rebuilt in 2012. Seller does not make any representation on the legality of the garden unit, this unit was fully rehabbed in 2019, tuckpointing was professionally completed in 2021, and the HVAC systems were fully updated in 2025. Unmatched outdoor space includes private decks for every individual unit, plus an expansive common deck equipped with a private Jacuzzi-an entertainer's dream. To top it off, this property solves Chicago's toughest challenge by offering 6 dedicated parking spaces in addition to easy street parking. Located just steps from Bucktown's premier dining, boutique shopping, Mariano's, parks, and the Blue Line. Also steps from the Clybourn Metra stop which runs nonstop to the Ogilvie Transportation Center Exceptional cash flow potential in an A+ location!Tax Assessment has been successfully appealed for an expected reduction of $1,512.00.

1808 W Armitage Street, Chicago

$1,200,000
8 Beds 4 Baths 12688343 MLS ACTIVE Status
A phenomenal Bucktown location, zero vacancy, and an incredible rent roll - this classic four-flat is a rare fully-leased investment opportunity, with all four units occupied at market rents and income in place from day one. Set a half-block west of Damen on a quiet residential street surrounded by single-family homes, the building offers four full-floor units, each with two bedrooms, one bath, hardwood floors throughout, in-unit laundry, and independently updated mechanicals - HVAC, electrical, and plumbing serving each unit separately. Several systems were replaced between 2019 and 2024, and Unit 1F was fully remodeled in 2020, keeping deferred maintenance light for years to come. Gated entry, a shared deck, and two to three exterior parking spaces at the rear round out the building. Location does the heavy lifting on rental demand here: the 606 Trail, Walsh Playground, and Mariano's all sit within a short walk, the Blue Line is under a mile away, and I-94 access is just blocks off - the kind of walkability that keeps units leased and turnover low. A walk-up of this vintage is some of Bucktown's most resilient building stock, ideally suited to a long-term hold. Strong bones, a strong corner of the city, and a stabilized, fully-performing asset in one of Chicago's most in-demand neighborhoods.

2040 W Charleston Street, Chicago

$1,300,000
10 Beds 5 Baths 12669951 MLS ACTIVE Status
Rarely available and meticulously maintained, this turn-key Sheridan Park gem offers an unmatched investment opportunity for savvy buyers and portfolio collectors alike. This premier estate showcases an exceptional pride of ownership, featuring a classic, solid brick 2-flat, a fully finished walk-out garden unit, and a spectacular, detached multi-level brick coach house. Generating four distinct income streams, the property provides incredible financial versatility, allowing a live-in owner or a seasoned investor to maximize immediate rental yields. Every inch of this building reflects an extraordinary attention to care and structural maintenance, making it a truly worry-free asset. The primary building delivers three distinct, high-income living spaces with excellent layouts, generous square footage, and 2 to 3 separate entrances or exits per unit for optimal privacy and safety. The middle and upper units boast airy ceiling heights, spacious bedrooms, beautiful hardwood flooring, upgraded windows, and gourmet kitchens complete with granite countertops and eat-in islands. The sun-drenched upper-floor unit features a three-bedroom, one-bathroom floor plan with bright living areas, a dramatic marble tile fireplace, & custom wet bar. Below it, the middle-floor unit provides an exceptionally functional two-bedroom, two-full-bathroom layout that is perfect for roommates or families seeking extra privacy. The fully finished walk-out lower level houses an in-law garden unit complete with three bedrooms, a private bathroom, open concept kitchen, sunny windows, modern flooring, and contemporary lighting. This level also features a designated shared laundry room for the main building units, accessible via the shared walk-out basement entrance or multiple interior entrances. Enjoy ample storage and workshop space in the basement. Stepping into the backyard reveals a private outdoor oasis that feels completely removed from the bustle of the city. The deep lot is landscaped to include beautiful gardens, a relaxing pergola, pristine swimming pool, an expansive patio for grilling. Tucked away at the rear of this urban sanctuary sits the private, multi-level solid brick coach house. This unique detached structure boasts an open-concept living and dining area, galley-style kitchen with granite countertops, two bedrooms, full bathroom, and basement with its own dedicated, private in-unit laundry. It even features a private patio with a mini garden, making it a highly coveted rental asset. Convenience, accessibility, and vibrant neighborhood amenities are unmatched at this prime location. The property includes ample off-street parking, a rare commodity on a quiet, tree-lined residential street. Commuters will love being just a short distance from major CTA bus routes, Metra, and CTA. Near Red, Purple, Green, & Brown line. Residents will enjoy being steps away from the historic Green Mill jazz club & Chase Park's tennis, athletic field, & playground. Take a short drive to nearby beautiful Montrose Beach or enjoy vibrant dining, shopping, and entertainment just steps away. Character, cash flow, and pristine condition converge perfectly in this unique multi-unit compound.

4749 N Dover Street, Chicago

$3,600,000
7 Beds 7 Baths 12644647 MLS ACTIVE Status
33 E Division was originally constructed in 1881. This historic Potter Palmer Greystone sits on a rare 23.5-foot-wide lot - one of the few wider residences built in the Gold Coast during that era. This historic property encompasses over 7,000 square feet across six levels and is currently configured as four income-producing apartments, with a rare four-car tandem garage created from the former fifth apartment and the original one-car garage. Whether maintained as an investment property, transformed into a boutique luxury residence, or restored into a magnificent single-family mansion, the opportunities here are truly endless. Each apartment throughout the building includes soaring 10+ foot ceilings, original millwork, stained glass, hardwood floors, carved oak mantels, and marble fireplaces. Lovingly maintained by the same owner for nearly 50 years, the property has many updates, including windows, electrical, plumbing, HVAC systems, and roof #1: A ground-level studio with a fireplace, generating $2,000 per month. Lease expires 4/30/27 #2: A generously sized bi-level 2-bedroom, 2-bath residence featuring four fireplaces, a formal dining room, a jacuzzi tub, a steam shower, a private deck (20.5 x 8.0), and rare 4-car parking, generating $5,500 per month. Lease expires 4/30/27. #3: A 1-bedroom apartment and fireplace generating $2,500 per month. Lease expires 10/31/26. #4: A large bi-level 3-bedroom residence featuring three fireplaces, a balcony, a jacuzzi tub, a steam shower, and an expansive private rooftop deck (39.9 x 15.10), generating $6,200 per month. Lease expires 7/31/26 Located in the heart of Chicago's prestigious Gold Coast, just steps from the lakefront, Oak Street Beach, the Magnificent Mile with shopping & fine dining, plus designer boutiques on Oak Street. Just moments from Oak Street Beach and Lake Michigan, Michelin-rated dining, world-class shopping, celebrated entertainment, and renowned cultural attractions, this address delivers the very best of Gold Coast living.

33 E Division Street, Chicago

$950,000
12 Beds 4 Baths 12654695 MLS ACTIVE Status
Rare opportunity to purchase entire 4-unit brick building on a double wide lot with a large backyard that borders a golf course. Entire building has recently been tuckpointed. 2 new furnaces installed in July 2026. Each unit has 3 bedrooms and 1 bath. One unit has been completely rehabbed including a complete gut rehab bathroom with beautiful tilework, complete rehab kitchen with premium cabinets & luxury vinly flooring, and refinished hardwood flooring throughout. The selection of granite countertops and appliances still available for the owner to choose. The other 3 units are ready for customization or can be rented out. Actual taxes paid in 2025 -- $8,158 (does not include all home owners exemptions). Excellent income earning potential.

6626-6628 N Seeley Avenue, Chicago



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