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5 Flat Apartment Buildings For Sale In Chicago IL

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Newest 5-flats Properties In Chicago

$2,150,000
12673900 MLS NEW Status
Once in a Generation, The Crown Jewel of Oakland set on a botanical campus spanning 70 feet of frontage. If you seek the best, if you have exquisite taste, if you want a one of a kind with an elevator that opens directly into most apartments with grand terraces, you have arrived. Located in an exclusive community alongside million dollar homes & within 1/4 block of Mandrake Park, 5 minute walk to the lakefront at the very north end of Drexel Blvd, with its idyllic fountain & cul-de-sac is a magical whimsical storybook setting offering 5 Massive full-floor units ultra-luxurious 3-4 Bed/2-3 Bath residences set in a made for TV boutique, elegant, Gothic Greystone. Be inspired by the grand, formal lobby with inlaid stone floors, intricate woodwork, stunning modern art, a crystal cut chandelier & super "mod" LED wall sconces. The elevator opens directly into most residences' private foyer, which leads to a massive great room, with soaring ceilings & 7' tall window bays that capture phenomenal sun soaked south & west vistas up & down lush & forested Drexel Boulevard. Gorgeous plank hardwood floors, which contrast with sleek 7" crown & baseboard moldings, 8' tall solid core doors, polished chrome door handles & accessories, a custom designed & built fireplace with glass, stone & quartz mantel + gorgeous lighting with Decora switches & dimmers. Adjacent to the great room, cook, entertain & eat in a true & REAL gourmet kitchen with 1 1/4" thick quartz countertops, a massive work island with bar stool seating, state-of-the-art stainless appliances, a multi burner stove, tunnel exhaust hood, dishwasher, 36" refrigerator with ice & water dispensers, built-in microwave drawer & brilliant porcelain full height backsplashes. Other features include strategically placed cable & electric for flat screen televisions, Hi Efficiency HVAC, high tech LED lighting & many other features. Gracious jaw dropping primary bedroom suite with an infusion of natural light from tall south facing windows, enormous walk-in closet is ready to house a large wardrobe, with custom double hanging SS organizers some which include 20 lineal feet of hanging & 55 lineal feet of shelves. Resort Luxury spa bathroom with heated porcelain tile heated floors, steam shower, quartz bench, a custom designed floor to ceiling glass wall & door system, a rain shower, handheld shower & separate body washes, 6' air bath, a wall mounted floating double bowl vanity & two large mirrored medicine cabinets. Numerous oversized rear terraces offer respite to enjoy cocktails, read a book or have breakfast through dinner, private & spacious with sweeping downtown views. Full Laundry Center complete with full size washer & dryer, countertops & cabinetry cabinets. Enjoy fully curated exotic botanical gardens fully with specimen trees & bushes, many grafted, from around the world, including Japan, various countries in Eastern Europe, Canada & the USA ( all irrigated controlled by app) topped off with 9 car garage (2 of 9 Tandem). Fully stabilized with exceptional longer term tenants, this stunning, unique, trophy property offers a rare hybrid opportunity pairing investment with legacy. Full financials, floorplans, survey, and extensive pictures available. Actual Annual Income $213,045/NOI $141,525 / 6.5CAP Pre Approved buyers only. 48-72 hours' notice to show M-F (no weekend showings)

3967 S Drexel Boulevard, Chicago

$1,560,000
12730594 MLS ACTIVE Status
Exceptional Turnkey 5-Unit Asset in Prime Pilsen with Strong 7.15% Cap Rate & Significant Immediate Upside. Originally reconfigured as an owner-occupied building. Highly lucrative, fully permitted 5-unit commercial residential building situated on a prominent corner lot in Pilsen. Extensively gut-rehabbed to the studs between 2013-2023 with all-new building systems, modern layouts, and premium finishes. Operating at a strong 7.15% current Cap Rate with a projected 1.42 Debt Coverage Ratio (DCR), this asset offers rare immediate bankability and day-one cash flow. UNMATCHED VALUE-ADD OPPORTUNITY: The 1st-floor 1,500 sq. ft. 1BR/1BA loft tenant is vacating, creating an immediate, frictionless opportunity to capture a massive market rent increase or split the oversized floor plan to maximize total yield. Both 1701 W 21st St and 2102 S Paulina St addresses included in sale on single PIN. PREMIUM MECHANICALS & INFRASTRUCTURE: Fully updated water service replaced with copper directly to the city main. Low expenses: Tenants responsible for utilities with separately metered gas and electric. Individual furnaces, central AC, and separate tank/tankless water heaters for every unit. Attached 2-car garage off the alley providing additional premium rental income. Full unfinished basement housing utilities with storage spaces for tenants. HIGH RENTER RETENTION: Well-appointed apartments feature stone/quartz countertops, stainless steel appliances, premium hardwood or engineered flooring, masterfully tiled baths, and convenient in-unit washers and dryers. Superb location with immediate access to Pilsen public transit. Currently self-managed with zero historic vacancy. Clean rent roll, P&L, and T12 commercial underwriting documents available upon request.

1701 W 21St Street, Chicago

$415,000
12715119 MLS RE-ACTIVATED Status
** BACK ON THE MARKET! This exceptional FULL-brick 5-unit investment opportunity near Downtown Oak Park is available again after the buyer was unable to secure financing. An excellent opportunity for investors looking for a well-located multifamily property.** This rare opportunity to own a meticulously maintained, fully brick 5-unit apartment building located on a quiet residential street just over one mile from vibrant Downtown Oak Park and only eight miles from Downtown Chicago. This turnkey multifamily property offers dependable cash flow, strong rental demand, and exceptional long-term appreciation potential. Each of the five spacious units offers generous living space with well-designed floor plans that appeal to today's renters. The property has been exceptionally maintained and features a private parking lot with space for up to 7 vehicles, an on-site coin-operated laundry that provides additional income potential, and separate hot water tanks for each unit, enhancing both tenant convenience and operational efficiency. The owner currently pays heat for four of the five units, along with common area electric, water, insurance, and real estate taxes, while the garden unit tenant pays all of their own utilities. Combining solid brick construction, oversized apartments, ample off-street parking, and a prime location near shopping, dining, parks, public transportation, and downtown Chicago, this property is an outstanding investment opportunity. Whether you're looking to expand your portfolio or acquire your first multifamily asset, this well-performing income property offers the perfect blend of stability, value, and future growth potential.

5220 W Washington Boulevard, Chicago

$1,230,000
12714298 MLS ACTIVE Status
RARE investment opportunity in the heart of Bronzeville-a beautifully restored 1903 historic mansion thoughtfully converted into four oversized luxury apartments on a rare double-wide lot with additional value-add potential. This architect-designed 2025 renovation masterfully blends timeless vintage character with modern functionality, preserving original stained and leaded glass, intricate woodwork, hardwood floors, pocket doors, fireplaces, built-ins, and original doors throughout while introducing all new plumbing, upgraded 400-amp electrical service with separate meters, water heaters, insulation, custom kitchens, designer bathrooms, and individual HVAC/mini-split systems. Residents enjoy exceptional outdoor amenities including a welcoming front porch, private rear decks, side yard, and common courtyard patio. A substantial brick coach house provides three garage parking spaces on the main level while the upper level offers an outstanding opportunity for future expansion. Previously configured as additional living space, it presents tremendous potential for a fifth residential unit, guest suite, studio, office, or other income-producing use, subject to buyer verification and any required approvals. Each apartment occupies nearly an entire floor and benefits from four exposures, flooding the homes with natural light while offering spacious layouts, large bedrooms, in-unit laundry, private storage, and thoughtfully designed kitchens featuring soft-close cabinetry, solid surface countertops, induction cooking, upgraded appliances, designer backsplashes, and vent hoods. Bathrooms have been beautifully updated with a combination of walk-in showers, marble flooring, restored clawfoot tubs, and custom vanities. Quietly situated on a charming residential street surrounded primarily by single-family homes, this truly one-of-a-kind turnkey investment combines luxury finishes, irreplaceable historic architecture, and strong long-term rental appeal, with the added opportunity to further enhance value through the coach house. A rare offering in one of Chicago's most dynamic and appreciating neighborhoods.

4541 S Forrestville Avenue, Chicago

$1,250,000
12635682 MLS ACTIVE Status
Five units. Two buildings. Value-add opportunity in one of Chicago's most coveted neighborhoods. This classic East Humboldt Park brick 3-flat plus coach house sits just steps from the energy of Division Street and Milwaukee Avenue - walkable to Big Star's legendary tacos, Bongo Room brunch, Antique Taco, and the boutique shops, vintage stores, and nightlife that make this corridor one of the most sought-after in the city. Two blocks away, Humboldt Park delivers 207 acres of green space, a stunning lagoon, the beloved boathouse, walking and biking trails, and some of the most beautiful mature tree canopy in Chicago. The Blue Line is right there. The 606 trail is close. In a market where renters compete fiercely for quality units, this is the address that wins. The front building delivers three spacious 2-bedroom, 1-bath apartments - each featuring a sunroom, living room, kitchen, and timeless Chicago brick character - with genuine upside for the investor willing to roll up their sleeves. Kitchens and baths are ripe for updates, and this neighborhood rewards every dollar invested. The full unfinished basement offers coin-operated laundry with room to add a second washer/dryer and built-out storage lockers for all five units - bikes, gear, the works. Out back, a shared yard with a pergola creates rare outdoor living space that tenants love and prospects remember. The coach house delivers two beautifully renovated open-concept studios, each with a full bath and modern finishes; the second-floor unit is flooded with natural light. Recent improvements include new front stairs and replacement windows. Tenants pay their own electric and heat; owner expenses are limited to water, trash, insurance, and first floor and common area electric.

2711 W Haddon Avenue, Chicago

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