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7144 S Bennett Avenue, Chicago
$217,000
10 Beds ⋅ 3 Baths ⋅ 12798671 MLS ⋅ NEW Status
THE LOT. THE LOCATION. THE UPSIDE. Welcome to 7144 S Bennett Avenue, a substantial three-story brick three-flat in Chicago's South Shore neighborhood, situated on an impressive 50 x 135 oversized lot. Featuring a reported 10 bedrooms, 3 bathrooms, a full basement, and garage parking, this property offers the scale and potential experienced investors look for. Near Jackson Park, Lake Michigan, public transportation, and the Obama Presidential Center, the location adds another compelling reason to take a closer look. A BIG PROJECT WITH BIG POTENTIAL! Restore, reposition, and explore the possibilities of this classic Chicago multifamily property. Extensive rehabilitation required. Known building violations and structural concerns exist. Sold strictly AS-IS. Buyer to verify condition, legal use, and renovation feasibility. Bring your contractor. Run your numbers. Schedule your showing today!

7144 S Bennett Avenue, Chicago

7921 S Prairie Avenue, Chicago
$390,000
6 Beds ⋅ 5 Baths ⋅ 12798587 MLS ⋅ NEW Status
Classic brick charm, generous space, and exceptional versatility come together in this two-unit property, located in Chatham on a quiet, well-cared-for block! Each unit offers three generously sized bedrooms, one-and-a-half bathrooms, and separate heating. Central air conditioning adds comfort and appeal. Picture windows and distinctive masonry create striking curb appeal, while the interior showcases light-toned flooring, recessed lighting, a separate dining area, and a stylish kitchen with gray cabinetry and stainless steel appliances. The finished basement provides additional space for related living, including a standout shower with dramatic marble-look tile, rainfall fixtures, and built-in seating. Enjoy backyard gatherings and unwind in the hot tub, which stays with the building. A three-car garage adds valuable parking and storage, and a roof completed in April 2026 rounds out the highlights. An appealing opportunity for an owner-occupant or investor-schedule your private showing and explore the possibilities!

7921 S Prairie Avenue, Chicago

6606 S Rhodes Avenue, Chicago
$715,000
7 Beds ⋅ 6 Baths ⋅ 12798520 MLS ⋅ NEW Status
Classic Greystone character meets modern living at 6606 S. Rhodes Avenue in Chicago's sought-after Woodlawn neighborhood, near the Obama Presidential Center. Completely rehabbed with full permits and approved inspections, this legal three-unit building offers an exceptional opportunity for investors and owner-occupants alike. The thoughtfully designed unit mix includes one three-bedroom and two two-bedroom residences, each featuring two full bathrooms, a primary bedroom with an ensuite bath, and in-unit laundry hookups. Kitchens showcase custom cabinetry, quartz countertops, and stainless steel appliances, complemented by stylish, modern bathrooms throughout. Extensive improvements include a new roof, windows, electrical, plumbing, heating, rear porch, and stairs-providing a fresh start with fewer immediate maintenance concerns. A comprehensive drain tile system and well pump provide added protection for the lower level. Enjoy nearby schools, restaurants, and parks, with the Green Line just blocks away and convenient access to Hyde Park, the University of Chicago, and Chicago's magnificent lakefront. Live in one unit while generating rental income from the others, or add a fully renovated three-unit property to your investment portfolio. Special buyer programs may be available to qualified purchasers. Ask about eligibility and financing options through our preferred lender, and make your move in time for the holidays!

6606 S Rhodes Avenue, Chicago

1242 Wenonah Avenue, Berwyn
$450,000
6 Beds ⋅ 2 Baths ⋅ 12798200 MLS ⋅ NEW Status
Don't miss this great opportunity to own a spacious two-unit property with a basement in Berwyn! Each unit features 3 bedrooms and 1 full bathroom, offering plenty of space and flexibility for homeowners, extended families, or investors looking to generate rental income. With two separate living units and a basement providing additional space and storage potential, this property offers endless possibilities-live in one unit and rent out the other, or add it to your investment portfolio. Situated on a quiet, tree-lined street in a highly walkable neighborhood, it's just steps from the vibrant restaurants, music venues, and culture of nearby Oak Park, minutes from the Depot District's shops and dining, and close to parks like Proksa Park, Berwyn Gardens, and Mraz Park. Enjoy easy access to Metra BNSF (Berwyn Station ~6 minutes) and the CTA Blue Line for a quick commute to downtown Chicago (~20 minutes), plus nearby shopping along Harlem Avenue and Cermak Road, local schools, and MacNeal Hospital. Schedule your showing today!

1242 Wenonah Avenue, Berwyn

15525 W Hoff Road, Manhattan
$649,999
6 Beds ⋅ 3 Baths ⋅ 12798232 MLS ⋅ NEW Status
Your country lifestyle awaits! This unique 10-acre Manhattan property offers 6 bedrooms, 3 full bathrooms, and a 4-6 car garage that can double as a workshop space. The home features 3 bedrooms on the mail level and 3 bedrooms upstairs providing plenty of room for family, guests, or home office space. The farmhouse- style kitchen was updated in 2021 and appliances that stay. Additional highlights include a dining room, family room, breakfast nook, first floor laundry, and newer bamboo flooring throughout. Equestrian enthusiasts will love the 11 horse stalls, 3 corrals, and horse arena. Enjoy the outdoors with a lovely patio and a playground that was added in 2023. Schedule your showing today- there is so much more to appreciate when you see the property firsthand!

15525 W Hoff Road, Manhattan

8019 S Eberhart Avenue, Chicago
$400,000
6 Beds ⋅ 3 Baths ⋅ 12798271 MLS ⋅ NEW Status
Stunning, fully renovated brick 2-flat offering the perfect blend of timeless Chicago character and modern luxury! Whether you're an owner-occupant looking to help out your mortgage or an investor seeking a turnkey income-producing property, this beautifully updated building checks every box. Each spacious unit has been thoughtfully renovated with gleaming hardwood floors, recessed lighting, and an open, light-filled layout. The modern kitchens feature espresso shaker cabinetry, granite countertops, stainless steel appliances, subway tile backsplashes, and abundant cabinet space, creating an ideal setting for everyday living and entertaining. The expansive living rooms showcase beautiful bay windows that flood the space with natural light, while the generously sized bedrooms and updated bathrooms provide both comfort and style. Major improvements throughout offer peace of mind, making this a truly move-in-ready investment. Situated on a quiet, tree-lined street, the property offers easy access to public transportation, major expressways, parks, schools, shopping, and dining. Conveniently located near the University of Chicago, the future Obama Presidential Center, and several ongoing neighborhood revitalization projects, this is an exceptional opportunity to own in one of Chicago's rapidly appreciating South Side communities.

8019 S Eberhart Avenue, Chicago

401 W Elm Street, Urbana
$340,000
7 Beds ⋅ 3 Baths ⋅ 12797549 MLS ⋅ NEW Status
Originally built as a duplex in 1914, this distinctive West Urbana property offers historic charm, generous living space, and investment potential. Designed with two mirror-image residences, the property retains beautiful original woodwork, hardwood floors, fireplaces, and unique architectural details, including back-to-back staircases. Previously utilized as professional office space, the building was reconfigured in 2013 to feature one spacious, renovated kitchen and expansive common areas. The current layout includes 10 bedrooms, consisting of six generously sized bedrooms and four additional bedrooms, along with three full bathrooms. Conveniently located near downtown Urbana, shopping, dining, and local amenities. Fully leased through July 2028, offering an established rental income opportunity for investors.

401 W Elm Street, Urbana

170 Round House Street, Braidwood
$325,000
10 Beds ⋅ 6 Baths ⋅ 12798101 MLS ⋅ NEW Status
Offered at $325,000, representing an entry basis of just $81,250/unit (as a 4-unit) or $54,166/unit(upon 6-unit conversion), and approximately $62.70/sq. ft. across the primary floors. Massive Floorplate & Scale: Substantial footprint totaling ~5,182 sq. ft. across two primary levels (~2,591 sq. ft. per floor), allowing for oversized, high-demand 2-bedroom rental layouts. Unit Density Expansion: Full attic space provides the immediate physical potential to add 2 studio apartments, increasing the property from a 4-unit to a high-density 6-unit income generator. Substantial Forced Equity & Cash Flow: Blank canvas condition allows an investor to select high-durability, modern finishes to capture top-of-market rental rates in a strong local rental market. Durable Masonry Construction: Solid all-brick exterior concrete block building with concrete precast floors. ongoing structural and exterior maintenance overhead. Favorable Will County Location: Positioned with convenient access to Route 53, I-55, and regional industrial/logistics employment lPrime Value-Add Multi-Family Opportunity | High-Upside All-Brick Asset 170 Roundhouse St, Braidwood, IL 60408 Solid, all-brick multi-family property offering massive value-add potential and significant scale. The building features an expansive footprint with approximately 2,591 square feet per floor, currently configured as four large 2-bedroom apartments ready for modern finishes and premium rental rates. Heavy Value-Add & Density Upside: Existing layout comprises four generous 2-bedroom units, with direct potential to build out the full attic space into two additional studio apartments-transforming the asset into a high-yielding 6-unit building. Substantial Scale: ~2,591 sq. ft. per floor delivers excellent room sizes, efficient mechanical routing, and optimal floor plans. Durable All-Brick Construction: Robust exterior framework minimizes long-term structural maintenance. Strong Pro-Forma Income: An ideal project for experienced investors or developers looking to maximize unit count, force appreciation, and capture strong cash flow. Prime Will County location with convenient access to regional employment corridors and Route 53 / I-55. Ideal for a 1031 exchange or portfolio addition. Sold as-is

170 Round House Street, Braidwood

5747 S Peek Home Road, Polo
$775,000
12 Beds ⋅ 9 Baths ⋅ 12798020 MLS ⋅ NEW Status
**HISTORIC CHARACTER, MODERN IMPROVEMENTS & ENDLESS POSSIBILITIES ON Approx 4 ACRES!** Discover a truly unique opportunity in the peaceful countryside of Polo, Illinois. Originally built in 1930, this impressive approximately 10,000-square-foot, 10 plus bedroom estate combines timeless architectural character with substantial recent investments in infrastructure, mechanical systems, and interior renovations. Situated on 10 scenic acres, with an additional 10 acres available for purchase, this one-of-a-kind property offers extraordinary space, versatility, and potential. The current owners have invested extensively in updating and improving the property, addressing many of the significant expenses associated with restoring a historic estate. Major improvements include a new septic system (2025), all-new exterior windows and doors (2025), updated PEX plumbing, electrical improvements, a new air conditioning system (2026), well improvements, and a substantial garage addition. Interior upgrades include approximately $110,000 in bathroom renovations, $75,000 in kitchen improvements, beautifully restored hardwood flooring, fresh interior and exterior paint, and extensive carpentry and common-area improvements. Throughout the residence, you'll appreciate the charm and craftsmanship of original millwork, two fireplaces, and expansive living spaces that offer flexibility for a variety of uses. While significant renovations have already been completed, the home presents an exciting opportunity for its next owner to add personalized finishes and bring their vision to life. The expansive grounds provide a picturesque country setting with numerous outbuildings, including a hay barn, grain barn, mini barn with paddock, a five-car detached garage, and an attached two-car garage. Recent improvements to the grounds include landscaping, tree removal, and the removal of aging structures. An EV charger adds another modern convenience. Whether you're searching for a grand private residence, a multigenerational family compound, or a distinctive property with potential for other uses subject to applicable zoning and approvals, the possibilities are exceptional. **With its remarkable scale, historic charm, extensive recent improvements, and additional acreage opportunity, this is a rare chance to make an extraordinary property your own.**

5747 S Peek Home Road, Polo

1116 S California Avenue, Chicago
$375,000
9 Beds ⋅ 6 Baths ⋅ 12798003 MLS ⋅ NEW Status
This exceptional investment opportunity is ideally located just steps away from beautiful Douglas Park. Situated close to the vibrant Tri-Taylor and Illinois Medical District neighborhoods, this property is perfectly positioned in one of Chicago's rapidly developing areas, surrounded by ongoing growth and redevelopment. Surrounded by nearby public transportation options and quick access to the I-290 expressway, providing an easy connection to downtown Chicago and surrounding neighborhoods. The location also places you minutes from major hospitals, universities, and local dining and shopping destinations. The property has been fully gutted, presenting a rare blank canvas for investors, developers, or homeowners with a vision. With the interior already cleared out, it's ready for your custom design, renovation plans, or redevelopment ideas to bring new life to this promising space.

1116 S California Avenue, Chicago

7929 S Harvard Avenue, Chicago
$250,000
6 Beds ⋅ 3 Baths ⋅ 12797897 MLS ⋅ NEW Status
Great opportunity to own this classic brick 2-unit building in the West Chatham neighborhood! Perfect for investors or owner-occupants looking to generate rental income while building equity. Boiler and Water Heater completed replaced in 2020. Each unit features 2 bedrooms and 1 bathroom, spacious living areas, hardwood floors, beautiful original woodwork, and charming architectural details throughout. The property offers generously sized rooms, kitchens with ample cabinet space, and plenty of potential for updates and customization. The basement provides additional space and includes an extra bathroom. Outside, enjoy a fenced backyard, and 2-car detached garage. Whether you're looking to live in one unit while renting the other or expand your investment portfolio, this property offers an excellent opportunity to add value while preserving its original charm. Bring your vision and make this property your own. Schedule your showing today!

7929 S Harvard Avenue, Chicago

7524 S Wentworth Avenue, Chicago
$300,000
6 Beds ⋅ 3 Baths ⋅ 12797860 MLS ⋅ NEW Status
Two units. More space. More possibilities. 7524 S Wentworth Avenue is a brick two-unit property with six bedrooms and three bathrooms across two separate residences. The spacious lower unit is a two-level duplex with four bedrooms and two baths. The upper unit offers two bedrooms and one bath. Both units have in-unit laundry, and the water heaters have been replaced. A three-car detached garage adds parking and storage. The lower unit is leased month-to-month at $1,850 per month, and the upper unit will be delivered vacant at closing. That makes this a fit for an owner-occupant who wants rental income or an investor adding to a portfolio. Both units could use some updating, so there's room to add value and build equity. The Red Line at 79th Street, a nearby bus stop, and quick access to the Dan Ryan Expressway make getting around easy. Sold as-is. Cash and fast-closing offers preferred. Seller is an Illinois licensed real estate broker.

7524 S Wentworth Avenue, Chicago

5412 N Western Avenue, Chicago
$825,000
7 Beds ⋅ 5 Baths ⋅ 12797854 MLS ⋅ NEW Status
Built in 1922, this gorgeous, extra-wide brick two-flat plus in-law suite sits in Budlong Woods on the western edge of Lincoln Square. Boasting seven bedrooms and a rare five full baths across three levels (first and second floor have two full baths each), livability and income potential are maximized. The building faces east across Western Avenue toward open green space. Morning sun beams straight through the front windows and in the evening, the enclosed back porches catch the sunset. Top floor has 3 bedrooms, 2 full baths, a formal living room, separate dining room, and enclosed back porch. First floor has 2 bedrooms, 2 full baths, a foyer, living and dining rooms, an electric fireplace and its own enclosed back porch. Both units have repurposed some of the original wooden doors to a "barn door" configuration to maximize space and can be reinstalled in the original fashion. First floor enjoys floating engineered flooring over sound-dampening underlayment, with the original hardwood still underneath and ready for refinishing. The lower level has 2 bedrooms, 1 full bath, stainless appliances, newer windows, lighting, radiators, and a marble-tiled entryway. Owner makes no representation as to the legality of the lower level unit. Shared coin laundry. 2-car garage plus a tandem parking pad for two additional cars. Out front: covered stair entries and a stylish patio for entertaining. The Western bus stops steps away and you're a short jaunt to Lincoln Ave, with its restaurants, coffee shops, Giddings Plaza and the Brown Line.

5412 N Western Avenue, Chicago

7712 S Ridgeland Avenue, Chicago
$299,000
6 Beds ⋅ 4 Baths ⋅ 12797733 MLS ⋅ NEW Status
***ACCEPTING CASH OFFERS!!!! BUYER COULDN'T GET FINANCED. Will not pass FHA inspection. Mold present in the basement.*** Majestic beautiful legal 4 flat on serene tree lined street. These 3 units of 2 bed/1 bath have the largest footprint in all of South Shore!!! These are regal sun drenched units with huge formal living room, separate formal dining room, breakfast nook off the kitchen with walk-in pantry, 2 massive oversized bedrooms, and fabulous long hallways that make the perfect gallery for art or family photos!!! Hardwood floors throughout!!! Units are so oversized, you can easily add a 3rd bdrm and another full bath. Full unfinished english basement large enough for an additional 2 or 3 bedroom unit, lovely cemented backyard and a 3 car garage!!! Entry reception hall into each unit with glass door enclosed built-in bookshelves. Regal building entry vestibule that's large enough to hold 30 people comfortably. Amazing spaces!!! Updates needed throughout. AS-IS! Mold present in basement. ****Must sign hold harmless prior to viewing!!!!

7712 S Ridgeland Avenue, Chicago

2124 S Trumbull Avenue, Chicago
$499,959
9 Beds ⋅ 3 Baths ⋅ 12797063 MLS ⋅ NEW Status
Investor's Dream: Fully Remodeled Multi-Family Gem This unique, high-yield investment opportunity is a true "cash cow" that checks every box for the savvy investor or the smart home buyer. Recently remodeled and move-in ready, this property features an efficient layout designed for consistent cash flow and high tenant demand. Property Highlights: * Unit 1: Spacious 5-bedroom, 2-bathroom layout located on the ground floor. * Unit 2: Well-appointed 4-bedroom, 1-bathroom residence on the second floor. * Upgrades: Recent renovations ensure low maintenance and immediate occupancy. * Prime Location: Situated in a highly desirable area with seamless access to public transportation, major commuter rail lines, and local shopping hubs. This property offers an exceptional blend of modern updates and strategic location, making it the perfect addition to any investment portfolio. Don't miss out on this rare chance to secure a turnkey asset in a thriving market-schedule your private tour today!

2124 S Trumbull Avenue, Chicago

1314 W Carmen Avenue, Chicago
$1,200,000
6 Beds ⋅ 2 Baths ⋅ 12797184 MLS ⋅ NEW Status
Andersonville- Most two-flats blend in, but this one breaks the mold! This classic Chicago brick 2-flat sits on an impressive 40 ft by 150 ft lot, allowing for over 3,400 sq ft of finished living space, a larger foot print than typical, a huge backyard that is a gardener's dream, and a beautiful custom bluestone patio. Both apartments are extra large with living rooms, family rooms and dining rooms as well. They both also feature private balconies. The first floor owner's unit has an internal staircase leading to the basement, providing easy access for potential duplex down conversion. The current owners have lovingly remodeled the space with attention to improvements while maintaining the original architectural details including untouched woodwork, some gas-light fixtures, speaking tubes & vintage ornate doorknobs. Most impactful is the creation of a kitchen that is straight out of a magazine and that you'd normally only see in a multi-million-dollar single family home! It boasts a custom oversized quartzite island with a cherry butcher block, a double-sized 48-inch Sub-Zero refrigerator, and a 48-inch Wolf double oven and stove top. High-end recessed lighting, in-ceiling speakers, and radiant floor heating enhance comfort during cooler months. The wall separating the kitchen and dining room was removed to create an open layout with a spacious dining room/great room area with the original built-in dining hutch still intact! The bathroom has been completely remodeled with new tile, custom quartz counters, a new triple-pane window, and a custom-built vanity. It features a walk-in shower with a bench, a custom shower door, premium fixtures, and radiant floor heating. Additional improvements include refinished walls in both apartments, new and refurbished lighting fixtures, and upgraded electrical service with two new panels (2025). The second floor has a different layout than the first with a fabulous family room adjacent to the kitchen, which has great storage and an original built-in butler's pantry. The full basement, with direct access to the first-floor apartment, offers ample storage space, a workshop area, and upgraded electrical systems, a new laundry room with beautiful tile walls, new cast-iron drains for the washer and dryer, a dog wash sink, new copper plumbing, and building-wide wired network and security cameras. Although there currently isn't parking behind the building, there are options for installing a garage, parking pad or doing a curb cut in front of the property. All this located in a spectacular Andersonville location just a couple of blocks from Clark Street with its wonderful shopping, restaurants, and bars, as well as the Red Line, and only a short distance to the lakefront and Lake Shore Drive as well. Top floor is rented for $3150 per month through the end of April 2028.

1314 W Carmen Avenue, Chicago

2235 Gunderson Avenue, Berwyn
$465,000
6 Beds ⋅ 3 Baths ⋅ 12797485 MLS ⋅ NEW Status
Brick 3-flat in Berwyn with three units: a 2-bedroom, 1-bath first-floor apartment, a 2-bedroom plus den, 1-bath second-floor apartment and a 2-bedroom, 1-bath garden unit. The City of Berwyn's October 2026 presale compliance report recognizes all three apartments. The second-floor unit is vacant, with hardwood floors, a den, a built-in hutch, a pantry and its own forced-air furnace: an owner-occupant can move in, or an investor can lease it. The garden unit has vinyl plank floors and a stainless gas range and is leased at $1,200/month through 9/30/27. The first-floor unit is leased at $1,525/month through 5/31/27. Shared basement laundry, fenced rear yard with patio, and a 2-car detached garage. Sold as-is: under Berwyn's code, the buyer takes on the items in the city's compliance report. Tenant-occupied. Showings by appointment only, with 48 hour notice.

2235 Gunderson Avenue, Berwyn



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