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5 Flat Apartment Buildings For Sale In Chicago IL

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Newest 5-flats Properties In Chicago

163 W Division Street, Chicago
$2,000,000
12785939 MLS ⋅ NEW Status
163 W. Division Street Chicago, A RARE INVESTMENT OPPORTUNITY IN A PRIME CHICAGO LOCATION! Financial Package Can Be Requested. Exceptional opportunity to own five beautifully furnished Units Currently operating as a successful Airbnb, ideally situated between the prestigious Gold Coast and historic Old Town neighborhoods. This highly desirable Near North Side location offers outstanding walkability, convenient public transportation, and easy access to some of Chicago's most popular dining, shopping, entertainment, and cultural destinations. The Gold Coast is renowned for its upscale lifestyle, beautiful tree-lined streets, historic mansions, luxury residences, designer boutiques, and celebrated restaurants. Residents and visitors enjoy the vibrant dining and nightlife along Rush Street and Division Street, premier shopping along Oak Street and the Magnificent Mile, and convenient access to Oak Street Beach, the Lake Michigan lakefront and scenic walking and biking paths. Nearby attractions include the Newberry Library, 360 CHICAGO Observation Deck, and the Museum of Contemporary Art. Historic Old Town is Just a short walk away and offers a distinctive blend of historic charm and lively urban energy, known for its picturesque residential streets, vintage architecture, unique boutiques, neighborhood restaurants, and vibrant entertainment scene, Old Town is home to the world-famous Second City comedy theater, the historic Old Town Triangle District, and the popular Wells Street corridor, featuring an array of dining, nightlife, and entertainment options. Its inviting neighborhood atmosphere and proximity to downtown make it an enduringly desirable destination for residents and visitors alike. Enjoy easy access to Chicago's premier attractions, including the Magnificent Mile, Oak Street Beach, Lincoln Park, the Chicago lakefront, and the city's renowned restaurants, shopping districts, and cultural venues. The nearby CTA Red Line at Clark/Division provides convenient connectivity throughout the city, making this location attractive to both long-term residents and visitors seeking an authentic Chicago experience. An outstanding opportunity for investors! These five-unit property offers the potential to lease all five units for traditional rental income or explore the opportunity to continue the existing successful Airbnb business. With its prime location, walkable surroundings, and access to Chicago's most desirable neighborhoods, this property presents an exciting opportunity for investors seeking to expand their portfolio in a sought-after urban market. A rare opportunity to capitalize on the appeal of Chicago's Gold Coast and Old Town neighborhoods in one strategic investment. Investor has the option to continue Airbnb or Lease units out. No caps or rental restrictions in this building.

163 W Division Street, Chicago

6501 S Saint Lawrence Avenue, Chicago
$250,000
12778120 MLS ⋅ ACTIVE Status
Prime Corner Commercial Investment Opportunity in the Woodlawn Redevelopment Corridor Located at the high-visibility corner of 65th Street and St. Lawrence Avenue in the rapidly evolving Woodlawn neighborhood, this versatile multi-unit commercial property presents exceptional upside for investors, developers, owner-users, and entrepreneurs seeking to capitalize on one of Chicago's emerging growth corridors. *Two units require roof replacement. Those units need repairs. Buyer to verify all roof and unit conditions during inspection. Price reduced to reflect roof replacement and unit repairs; sold as is.* This approximately 2,980 square foot commercial property features five retail/commercial spaces with a mix of turnkey occupancy and value-add redevelopment potential. Existing improvements include: * Fully built-out hair salon with modern styling stations and furnishings * Professional office suite with reception/waiting area * Multiple storefront entrances providing flexibility for multi-tenant occupancy * Updated mechanical systems including newer HVAC and water heater * Strong visibility and neighborhood presence * Flexible floorplans suitable for retail, beauty, office, creative workspace, service businesses, storage, or mixed commercial use Three additional units present an outstanding opportunity for customization, repositioning, or income-producing redevelopment. **Schedule your showing today and envision the possibilities!**

6501 S Saint Lawrence Avenue, Chicago

3967 S Drexel Boulevard, Chicago
$2,150,000
12780789 MLS ⋅ ACTIVE 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

4363 N Lincoln Avenue, Chicago
$2,395,000
12775292 MLS ⋅ ACTIVE Status
Trophy building at the heart of Lincoln Square, a highly visible corner across from Welles Park and Small Cheval. The building is anchored by L&M Deli, a neighborhood staple serving deli sandwiches, high-end groceries, as well as beer, wine, and liquor. In addition, there are four large apartments (1) 3 bed / 1 bath and (3) 2 bed / 1 baths. The building underwent significant renovation in 2007 including the replacement of all copper water lines, all electric, a new main water line, new windows, and the cosmetic renovation of all units. In 2022, new HVAC was installed for all of the retail space. The apartments all have central air AC with clean, rental quality finishes (hardwood floors, laminate counters, and entry level appliances). Laundry is a shared community room on the 2nd floor of the building. L&M Deli has been in business at this location for six years with four years remaining on their lease and (2) five-year options. The space has had extensive upgrades including two large, walk-in freezers, a 1,500 SF air-conditioned prep kitchen in the basement, as well as ventilation and black iron for the kitchen. In-place gross revenue is $229,000; a 10.26x Gross Rent Multiple; and a 6.9% cap rate on in-place income. Existing apartment rents are below-market, averaging $2,173 for the 2 Bed / 1 Bath units and $2,575 for the 3 Bed / 1 Bath. If rest to market rents, a new buyer could achieve stabilized gross revenue of $250,000 within one year of ownership; a 9.6x stabilized Gross Rent Multiple and a 7.7% return-on-cost. A new buyer has the opportunity to mark the existing apartment rents to market amid growing rental pressure and a lack of available supply, all while owning a trophy building with cash flow in place.

4363 N Lincoln Avenue, Chicago

838 N Wolcott Avenue, Chicago
$1,425,000
12761705 MLS ⋅ ACTIVE Status
Welcome to 838 N. Wolcott Avenue (the "Property"), a light value-add multifamily asset ideally positioned in the heart of Chicago's highly sought-after East Village / West Town neighborhood. Situated just north of the vibrant Chicago Avenue retail corridor, the Property offers investors the rare opportunity to acquire a well-maintained, cash flowing asset with meaningful rental upside in one of Chicago's strongest and most supply-constrained rental submarkets. The Property consists of three (3) 2 Bed / 1 Bath + Den units and two (2) 1 Bed / 1 Bath + Den units. These spacious floor plans are uncommon within the surrounding submarket and appeal to a broad tenant base seeking larger living spaces, work-from-home flexibility, and convenient access to the neighborhood's retail and dining amenities. Current ownership has invested significant capital into both the building's physical structure and major mechanical systems. Recent improvements include a complete tear- off roof and tuckpointing in 2024, basement repairs and a new basement entry door in 2025, and a new central A/C condenser in 2024. Unit-level mechanical updates have also been completed throughout the Property, including a new water heater and washer/dryer in Unit 1F (2025), a new washer/dryer in Unit 1R (2026), a new water heater and washer/ dryer in Unit 2F (2024) along with a new refrigerator in 2025, and a new dishwasher and faucet in Unit 3F (2024) followed by a new water heater and washer/dryer in 2025. The rear units have been renovated with condo-quality finishes, featuring stainless steel appliances, espresso and white cabinetry, granite countertops, and hardwood flooring throughout. Positioned one block north of Chicago Avenue, residents are within walking distance of notable local and national destinations including Lush Wine & Spirits, Beatnik, Forbidden Root, Opart Thai House, Arami, Roots Pizza, West Town Bakery, and the Chicago Public Library. The Property also benefits from exceptional transit connectivity, located approximately 0.2 miles from both the Kennedy Expressway and the CTA Blue Line, providing seamless access to Downtown Chicago, O'Hare International Airport, and surrounding neighborhoods. With its premier West Town location, oversized floor plans, recent capital improvements, and clear path to future rent growth, 838 N. Wolcott Avenue represents an exceptional opportunity to acquire a stable, operationally efficient multifamily asset with long-term upside in one of Chicago's most competitive rental markets.

838 N Wolcott Avenue, Chicago

1701 W 21St Street, Chicago
$1,499,000
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

2711 W Haddon 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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