“Honestly, at this point maybe we should all just buy a house together.”
The Multigenerational Home Planner

Could We Actually
Live Together?

Two households. Three generations. One big idea.

Compare buying together, buying a multifamily property, adapting a home you already own, creating separate living space, or keeping one property as a rental before anybody starts packing.

Planning tool only. No email required. Not a mortgage quote, appraisal, legal advice, tax advice, zoning determination or guarantee of costs.

Start with the family, not the floor plan

Maybe everybody keeps joking about living together. Maybe it is not really a joke anymore.

One household needs more space. Another needs less. Childcare is expensive. Aging parents want to be closer. Somebody owns a house with a lot of equity. Somebody else has a mortgage rate they never want to give up.

The point is not to convince everyone to share a roof. It is to compare realistic scenarios, see where the math gets interesting, and figure out what kind of property might actually work.

Step 1: Who are we solving for?
What is bringing everyone together?
Step 2: What does everyone pay now?

Household One

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Household Two

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Combined housing cost now
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Estimated combined equity
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Estimated sale proceeds available
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Step 3: What could living together look like?

Buy One Home Together

Model a larger home that could replace both households' current housing.

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How would the monthly cost be shared?

This does not determine legal ownership. It simply lets you test how the household budget might feel.

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Important: splitting the monthly payment is not the same thing as splitting ownership. Down payments, mortgage liability, title and exit rights need separate legal and financial planning.

Your Buy Together Snapshot

Change any assumption above and this updates automatically.

Current combined cost
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Modeled housing cost
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Monthly difference
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What everyone pays now

Modeled shared housing

The question that matters

 

Step 4: Okay. The math works.

Could you actually live together?

Saving money is lovely. Privacy is also lovely. Rate what your family would need from the property itself.

Feature
Must Have
Would Love
Don't Care
Separate entrance
Separate kitchen
Separate laundry
Private outdoor space
Sound separation
First-floor bedroom
No stairs / accessible route
Accessible bathroom
Dedicated parking
Home office
Separate utilities
Ability to rent part later

Your Multigenerational Home Wish List

Must haves: None selected yet

Would love: None selected yet

Property types worth exploring: Start selecting your privacy, accessibility and independence needs above.

The family meeting nobody wants to have

Before anyone contributes six figures, talk about the awkward stuff.

  • Who is contributing what upfront?
  • Who will actually own the property?
  • Who will be on the mortgage?
  • How are monthly expenses divided?
  • Who pays for a new roof or major repair?
  • What happens if someone's income changes?
  • What happens if someone wants to move out?
  • What happens after a death, divorce or remarriage?
  • Does caregiving count as a contribution?
  • Can one person's ownership interest be bought out?

If answering these questions makes Thanksgiving uncomfortable, imagine answering them after you have bought the house.

A shared real-estate purchase can raise mortgage, title, estate-planning, tax and legal issues. Get advice from appropriately licensed professionals before transferring money, signing financing documents or deciding how title will be held.

Want the real-world version?

Run Our Family's Real Numbers

You did the hypothetical version. I can help investigate what existing homes might realistically sell for, what could be available from a sale, which properties and layouts might work, and what local questions we need to answer next.

No obligation to buy or sell. Sometimes the best answer is that everybody should continue loving each other from separate addresses.

Important: This planner is for general educational and planning purposes only. Results are estimates based solely on user-entered assumptions. It is not an appraisal, comparative market analysis, offer to lend, mortgage quote, loan estimate, zoning determination, permit approval, tax advice, legal advice, investment advice or guarantee of costs, proceeds, rent, approval or payment. Rules for ADUs, separate living spaces, multifamily occupancy, renovations and rentals vary by property and municipality.

Some real life Chicago + suburbs multi-gen housing options

$469,900
8 Beds ⋅ 3 Baths ⋅ 12764393 MLS ⋅ NEW Status
Solid brick 3-flat in North Lawndale offering 8 bedrooms and 3 baths across three above-ground units with individually metered electricity and gas, plus an unfinished basement and 2-car garage. The updated, move-in-ready 1st-floor 2BR/1BA features a large open-concept eat-in kitchen and living area, a second spacious living area, in-unit washer/dryer, dishwasher hookups, and a large rear balcony-ideal for an owner-occupant or immediate rental income. The 2nd and 3rd floors each offer 3BR/1BA layouts with eat-in kitchens opening directly to large rear balconies, providing convenient outdoor dining space. The 2nd floor has W/D and dishwasher hookups, while the 3rd floor features central A/C and Chicago skyline views from the balcony. Both units offer substantial rental upside with future improvements. Recent capital improvements include replacement of the water service line and front sidewalk, completed by the City in 2024; upgraded basement support columns replacing wood posts with steel (2020); rear stair improvements (2026); garage door replacement; and mechanical and appliance updates to the 1st- and 2nd-floor units (2020-2024). Near expansive Douglass Park, offering an outdoor pool, tennis and basketball courts, soccer fields, walking paths, a lagoon and fishing, plus additional recreational amenities. Convenient access to the Illinois Medical District, I-290, public transportation, and the Roosevelt Road corridor.

1233 S Spaulding Avenue, Chicago

$750,000
5 Beds ⋅ 5 Baths ⋅ 12769620 MLS ⋅ NEW Status
***$20,000 Grant Approved Through the Cook County Land Bank!*** Rare opportunity in the Historic Garden district of East Garfield! Welcome to 2832 W Wilcox, a truly one-of-a-kind property that offers the best of both worlds. A rare cross between a traditional 2 flat and a single family home. This legal 2-flat encompasses 3150 Square feet, a total 5-bedrooms, 4.1 bath spanning 3 levels of living space. You can't get better than a dual Primary Suite, dual HVAC, dual Laundry area, and dual Kitchen. Private side entry for each unit. Whether you are searching for a multi-generational living arrangement, an owner-occupied investment, or a flexible property with endless possibilities, this unique residence delivers. Nestled on a tree line street, this sought after East Garfield property is just minutes away from the United Center and the transformative 1901 redevelopment project. This distinctive home offers an adaptable floor plan that provides the privacy and comfort of a single-family residence. Upper level showcases a primary suite with pass thru dual walk-in closets, a spectacular primary bath with dual vanity, freestanding tub, and oversized separate shower. Enjoy two generous guest bedrooms, oversized guest bath with double vanity sinks and laundry center. The incredible English garden level offers 2 Bedrooms and 2 bath, full living room, full kitchen with quartz countertops and stainless appliances. Your opportunity awaits so schedule your private tour today.

2832 W Wilcox Street, Chicago

$534,900
4 Beds ⋅ 3 Baths ⋅ 12762190 MLS ⋅ NEW Status
Fantastic opportunity in this beautifully maintained brick bungalow, currently configured as a legal 2-flat with a fully finished basement offering additional living space and exciting future potential. The second-floor unit is an immaculate 1-bedroom, 1-bath residence offering approximately 800 square feet, a beautifully updated kitchen and bath, private entrance, and separate gas and electric meters. The main-floor unit is currently duplexed into the finished basement, creating a spacious 3-bedroom, 2-bath residence. The main level features approximately 960 square feet with 2 bedrooms, 1 full bath, an updated kitchen, and separate gas and electric. The beautifully finished basement adds approximately 900 square feet with an additional bedroom, full bath, and generous living space. This flexible layout offers several possibilities for an owner-occupant or investor. Live in one unit while generating rental income from the other, maintain the current 2-unit configuration, or explore the potential of creating a separate garden-level unit, subject to applicable zoning, permitting, and City of Chicago requirements. Other notable improvements include a flood-control system in the basement designed to help protect against water intrusion, a new sewer line, and an additional sump pump for added protection and peace of mind. The brickwork, roof, and mechanical systems have also been well maintained. With updated interiors, separate utilities, multiple living spaces, and a versatile floor plan, this property offers an outstanding combination of condition, flexibility, and long-term potential.

3434 N Nagle Avenue, Chicago

$1,100,000
9 Beds ⋅ 5 Baths ⋅ 12769232 MLS ⋅ NEW Status
Stunning classic Greystone offering incredible character, spacious floor plans, and strong income potential in the heart of Edgewater. This legal 3-unit building also features a 1-bedroom, 1-bath in-law suite on the lower level, providing additional flexibility and income. The first and second floors each offer expansive 3-bedroom, 1-bath layouts with soaring ceilings, beautiful vintage details, generous room sizes, great natural light, and outdoor space. Much of the original woodwork and architectural character has been preserved while the building has been updated for modern living with forced-air heat, central air conditioning, dishwashers, and other improvements. The top-floor unit is an impressive 2-bedroom, 2-bath residence featuring vaulted ceilings, an updated kitchen and baths, in-unit laundry, a gas fireplace, and a bright, open feel. Current rent roll includes the lower-level 1-bedroom in-law suite at $900/month with a long-term month-to-month tenant; the first-floor 3-bedroom is currently vacant; the second-floor 3-bedroom rents for $1,900/month with a long-term month-to-month tenant; and the top-floor 2-bedroom, 2-bath rents for $2,600/month and is leased through August 2027. The property offers an excellent opportunity for a new owner to make improvements over time and further enhance an already beautiful vintage building. Several of the current rents reflect long-term tenancies and are below current market levels, offering additional income potential as units are updated and rents are brought closer to market. The vacant first-floor unit provides an immediate opportunity to make it your own, establish market rent, or owner-occupy while collecting income from the other units. A rare opportunity to own a beautiful Chicago Greystone combining vintage character, modern conveniences, existing rental income, and future upside. Out of respect for tenant privacy, only floor plans of the occupied units are included in the listing, but a full virtual tour is available. The vacant first-floor unit is available for showings at any time. All other units are available to be shown with a minimum of 48 hours' notice.

5835 N Winthrop Avenue, Chicago

$1,750,000
10 Beds ⋅ 5 Baths ⋅ 12764264 MLS ⋅ NEW Status
HOT LAKE VIEW 3 FLAT + 3 FLOOR COACH HOUSE | INCOME-PRODUCING | LIVE-IN & RENT | OPEN SAT & SUN | OFFERS REVIEWED THURSDAY Welcome to an exceptional rare investment opportunity in the heart of Chicago's highly desirable Lake View neighborhood. This Victorian 3 Flat with Coach house is offering four income-producing units that includes a separate coach house, these 2 properties present the kind of versatility that sophisticated investors and owner-occupants look for. Whether your vision is to maximize rental income, live in one residence while generating income from the others, or hold a multi-unit asset in a premier Chicago location, this property provides a range of possibilities. Beyond the income potential, the location is a true standout. Enjoy the best of Lake View living with an abundance of restaurants, cafes, shopping, entertainment, parks, neighborhood amenities, and convenient transportation just moments away. It is a location that continues to attract residents who want the energy of the city while enjoying the character and community of a sought-after neighborhood. 4 units total, that includes the 3 flat and a separate Coach house. 2 amazing properties. An outstanding Chicago Lakeview location. Multiple strategies. One exceptional opportunity. Properties offering this combination of income potential, flexibility, and location are not often available. Whether you're an experienced investor or seeking a property with income-producing potential, this unique opportunity is ready for your vision and investment strategy. Come experience the property and explore the possibilities firsthand. Seller intends to review offers following the weekend, with a target of Thursday for highest and best. This is the Lake View opportunity you've been waiting for. Come see it, bring your vision, and make it yours. Serious inquiries only!

1529 W Nelson Street, Chicago

$650,000
6 Beds ⋅ 4 Baths ⋅ 12766158 MLS ⋅ NEW Status
Rare Oak Park 3-unit opportunity on a deep 50x171 lot! This classic stucco two-flat plus coach house offers flexibility few properties can match: live in one unit and let the other two help fund the mortgage, keep extended family close while everyone has their own space, or add a solid income property to your portfolio. Each unit has its own kitchen and hardwood floors, and old-world character shines throughout with high ceilings, crown molding, and working pocket doors. Tenants pay their own electric, gas, and heat. Outside, relax on the backyard patio and garden beneath mature trees, and enjoy 5 exterior parking spaces, a true rarity in Oak Park. The full, partially finished basement adds storage and flexibility, and there's room for dedicated home offices. Long-time owners are moving on and thoughtful updates offer a clear path to growing rents. First floor unit in main house has 2 bedrooms on first floor and 2 in the basement. Second floor unit has 2 bedrooms. The main house has been owner occupied for over 20 years. Coach house has 1 bedroom on the first floor and 2 in the basement. Tenants pay 1,800 in rent per month and are month to month with 60 day notice. The location is hard to beat: walk to the L train, Whittier School, Oak Park and River Forest High School, Pete's Fresh Market, the GRC, skate park, Ridgeland Common's pool and ice arena. The Daily Bagel and Thai Neighbor restaurant just steps away. Easy access to downtown Chicago. Don't miss this one!

540 N Harvey Avenue, Oak Park

$1,199,999
9 Beds ⋅ 6 Baths ⋅ 12768124 MLS ⋅ NEW Status
Rock Star Location, Uncompromising Livability, Intentional Design, and Architectural Significance. This Newly built 3 -story full masonry building is ready for delivery whether you are looking for a spacious home to live in, or for an effortless investment opportunity. The site location is strategic--the property is located just 2 blocks from the elevated train line and not on top of it which makes it close enough, and yet far enough away( Access without the noise) The Architectural design was thought out and improved on to ensure each bedroom, kitchen, living area and bathroom was maximized for functionality and the highest form of livability. The site lines from the extra tall vaulted ceilings with massive front elevation windows, wide open spaces and natural light directed from all sides. The finishes have been thoughtfully curated and intentionally designed to make for a timeless and exceptional living experience rather than conforming to what is trending. Living space matters and so each unit offers a generous 1400 Sq ft floor plan. The outdoor space is proprietary to each floor and spans wide and runs deep coming in at about 14 x 10 for each balcony. There is a 3 car masonry garage to take the guess work out of where to park, and no car needs to settle for an outdoor space come winter! The garage was constructed with a higher load capacity truss system for your potential ideas to do so much more. The property lends itself to the owner/ user with an opportunity to capture additional income from the other two units, or serves as an ideal investment for an arm chair investor for incredible income potential. The property is brand new and so there is literally nothing to do but manage it. You can have it all, location, spacious living areas, outdoor space, full masonry structure, 3 car masonry garage and the peace and quiet you want and deserve! Experienced Development team with over 40 years building from the ground up, and so the property is backed by a warranty.

4217 S Indiana Avenue, Chicago

$650,000
8 Beds ⋅ 3 Baths ⋅ 12767655 MLS ⋅ NEW Status
Stunning, fully renovated 2-flat with an updated additional in-law suite, offering modern design, beautiful finishes, and extensive upgrades throughout. Thoughtfully updated from top to bottom, this move-in-ready property combines style, comfort, and functionality. The first-floor unit features a spacious living room that flows into an open-concept kitchen and dining area, creating a bright and inviting main living space. The beautifully renovated kitchen features modern cabinetry, quartz countertops, new hardwood flooring, and contemporary finishes. Completing the first-floor layout are three generously sized bedrooms and a beautifully updated full bathroom with a tub. The second-floor unit offers a similar thoughtfully designed layout, featuring a spacious living room, open-concept kitchen and dining area, three generous bedrooms, and a renovated full bathroom with a tub. The finished basement features an updated additional in-law suite with two additional rooms and one full bathroom, providing versatile additional living space. Each unit is equipped with its own HVAC system, electrical panel, water heater, and washer and dryer hookups, providing independent comfort, convenience, and efficiency. Extensive improvements throughout the property include new electrical, new plumbing, new windows, central air, new mechanicals, new flooring, new tuckpointing, a new roof, new sump pump, and new ejector pump. The property also features a newly constructed wood porch with deck, providing additional outdoor space. A spacious concrete parking area accommodates at least four vehicles, offering excellent off-street parking and added convenience. Beautifully redesigned with attention to detail throughout, this impressive 2-flat with an additional in-law suite presents an excellent opportunity for owner-occupants or investors. A must-see property that is ready for its new owner. Schedule your showing today!

1015 N Laramie Avenue, Chicago

$799,000
6 Beds ⋅ 5 Baths ⋅ 12767898 MLS ⋅ NEW Status
Mid-Century Modern four-unit property in a highly desirable Elmwood Park location! Offering more than 5,000 square feet of living space, this fully leased building with 100K in RECENT IMPROVEMENTS presents an outstanding sole investment or owner-live-in opportunity! The current rent roll includes Unit 1 at $1,995 per month, Unit 2F at $1,350, Unit 2R at $1,250, Unit G at $1,250, and the garage at $175. GMR totals $6,020 per month, or $72,240 annually. The property includes six bedrooms and five full bathrooms across four apartments. Each residence has its own thermostat and individually controlled AC unit. Tenants share a basement common area and laundry room with a free, owner-owned washer and dryer. The detached garage accommodates approximately 2.5 cars and is leased separately. The building combines vintage character with thoughtful updates, including striking tiger mahogany cabinetry and stainless-steel appliances. Approximately $100,000 in improvements have been completed since October 2024, with major investments in the property's systems. Updates include a brand-new Weil-McLain gas boiler, a new common water heater with annual service, a full electrical upgrade, sewer-main hydro jetting, camera inspection and repairs, new copper piping in the mechanical room, a new hot-water supply line to the garden unit, and a sprinkler system in the basement common area. Additional improvements include repainting, carpet cleaning, rent-ready repairs, new locks, deep cleaning, and new laminate flooring in Unit 1. Earlier improvements include tuckpointing, glass-block windows, and plumbing work. The building is also a prime value add candidate with large basement common room that can easily become a unit addition. As well as the opportunity for cosmetic upgrades to increase an impressive rent toll. Conveniently located within walking distance of the train, parks, and schools, this well-maintained income-producing property offers a compelling combination of location, vintage character, modernized building systems, and future rental upside.

2631 N 74Th Avenue, Elmwood Park

$699,900
6 Beds ⋅ 3 Baths ⋅ 12767756 MLS ⋅ NEW Status
WONDERFUL NORTH MAYFAIR YOU WILL FIND THIS FANTASTIC UPDATED OWNER LIVE IN WIDE BRICK 2 FLAT WITH GREAT CURB APPEAL. 1ST FL= 6RMS, 2 BEDRM, 1 BATH(UPDATED) ,HARDWOOD FLOORS, CHERRY KITCHEN FULLY UPDATED WITH LOTS OF CABINETS, GRANITE COUNTERS, STAINLESS STEEL APPLIANCES PLUS A STAINLESS STEEL & GLASS EXHAUST HOOD OVER THE RANGE & DISHWASHER. 1ST FLOOR & LOWER LEVEL HAS CENTRAL AIR. IF YOU NEED EXTRA LIVING SPACE THE LOWER LEVEL IS COMPLETELY FINISH INTO A FAMILY ROOM, BEDROOM / OFFICE, FULLY UPDATED BATH,LAUNDRY ROOM PLUS EXTRA STORAGE. FRONT EXIT WINDOW CAN BE INSTALL TO GET A 2ND EXIT (RIGHT NOW ONLY REAR EXIT ). 2ND FLOOR = BEAUTIFUL HARDWOOD FLOORS , 7 ROOM, 3BEDROOMS, 1 BATH (UPDATED) SEPARATE HOTWATER HEATER. A WONDERFUL FRONT SUNROOM WITH MAPLE FLOORS OPEN UP TO LIVING RM. LOTS OF MORNING LIGHT FROM THE EAST. THIS OWNER LIVE IN BUILDING WAS PROFESSIONALLY RENOVATED OVER THE YEARS ,THE WAY BUILDINGS SHOULD BE CARE FOR. UPDATES IN THE LAST 10 TO 12 YEARS INCLUDES: THERMO WINDOWS,ALUMINIUM CAPPING, TUCKPOINTING, 3+ FEET OF PARAPIT WALLS ( COMPLETE NEW BRICK) WITH COPPER COPING WITH A RUBBER STYLE ROOF WITH SILVER COATING. SEPARATE HEATING = 1 FORCE -AIR WITH CENTRAL AIR & 1 HOTWATER BOILER, 2 CIRCUIT BREAKER BOXES WITH NEW WIRING THROUGHOUT PLUS LOTS OF CUSTOM LIGHT SWITCHES ,RECESS LIGHTING THROUGHOUT, COPPER PLUMBING, 2 SEPARATE HOTWATER TANKS, 3 UPDATED BATHROOMS, 1ST FL RENOVATED KITCHEN, NEWER CONCRETE SIDEWALKS ON BOTH SIDES OF BUILDING, NEWER 2 1/2 CAR GARAGE WITH A YARD PARTY DOOR, AND 8 FOOT ALLEY OVERHEAD DOOR WITH OPENER. REAR OF BUILDING WAS NICLY SIDED. BACK STAIR FULLY ENCLOSED FROM BASEMENT TO 2ND FLOOR (NO SNOW OR RAIN INSIDE) . 31X126.7 LOT SIZE . FRONT AND REAL HALLWAYS HAS PORCELAIN FLOORING. PROPERTY WILL VACATED AT CLOSING AND SELLER ATTORNEY HAS ALL PAPERWORK READY TO CLOSE FAST. ATTACHED IS AN APPRAISAL REPORT FOR $735,000 FROM SEPTEMBER 2026 PLUS A HOME INSPECTION REPORT FROM A BUYER THAT COULDNT DO THE DEAL (SELLER WAS SOLD BY OWNER BUT 2DAYS BEFORE CLOSING -IT FELL APART. SORRY NO INTERIOR PICTURES DO TO SELLER WAS PREPARED TO MOVE AND TOO MANY THINGS ARE IN THE WAY. APPRAISAL REPORT HAS PICTURES. DONT WAIT IT THIS ONE WONT LAST.

4828 N Karlov Avenue, Chicago

$1,650,000
7 Beds ⋅ 5 Baths ⋅ 12758878 MLS ⋅ NEW Status
Charming 4-unit building with a true owner's unit on beautiful Lill Ave in the heart of Lincoln Park. The front building consists of 2 units: a 2-bedroom, 1-bathroom rental apartment and a 3-bedroom, 2-bathroom owner's duplex-up. The rear coach house features two 1-bedroom, 1-bathroom apartments. Between the buildings is a lovely shared yard with new patio pavers, mature landscaping, garden plots, outdoor furniture, and a grill. The owner's duplex is filled with natural light and overlooks the tree-lined street. The open concept layout features a dramatic vaulted ceiling in the living room and a dining area that opens into the recently updated kitchen. 2 bedrooms and a full bath complete the main level. Upstairs, the huge primary suite has an attached bath, walk-in closet, and a laundry room. All apartments have been thoughtfully updated, making them both aesthetically beautiful and comfortable for the long-term tenants. All apartments have central HVAC and separate utilities. The owner is responsible for common electric, water, and trash. The front building has in-unit laundry and the rear building has shared laundry in the basement. The building has been lovingly cared for by the live-in owner. Extensive updates and meticulous maintenance are evident. Amazing location, steps from Halsted St & Lincoln Ave shopping, dining & entertainment. Easy train access, and walkable to Alcott Elementary. 2 nearby leased parking spaces are transferable.

828 W Lill Avenue, Chicago

$850,000
6 Beds ⋅ 3 Baths ⋅ 12767465 MLS ⋅ NEW Status
Exceptional opportunity to own a beautifully updated 3-flat in the highly sought-after Logan Square neighborhood! This well-maintained, income-generating property offers a perfect blend of modern updates and classic charm, making it ideal for both investors and owner-occupants. Each unit features gleaming hardwood floors throughout, thoughtfully updated kitchens with stainless steel appliances, and stylishly renovated bathrooms complete with ceramic tile finishes. High ceilings and oversized windows create bright, airy living spaces filled with natural light, while all bedrooms are generously sized to comfortably accommodate a variety of living arrangements. The building is designed for convenience and privacy, offering separate entrances for each unit along with individually metered utilities-allowing tenants to pay their own gas, electric, and other services. Outdoor amenities include a rear patio, private backyard, and balcony/deck space-perfect for relaxing, entertaining, or enjoying Chicago's warmer months. A 2-car garage adds even more value, with one parking space already rented for $100/month, presenting an additional stream of income. Situated in a prime Logan Square location, this property is just steps away from a vibrant mix of local shops, popular restaurants, cafes, and nightlife. Enjoy easy access to the 606 Trail for walking, running, and biking. Commuting is a breeze with nearby public transportation options and quick access to major expressways. Whether you're looking to expand your investment portfolio or live in one unit while generating rental income from the others, this property checks all the boxes-location, condition, and income potential.

3041 W Fullerton Avenue, Chicago

$755,000
7 Beds ⋅ 3 Baths ⋅ 12764380 MLS ⋅ NEW Status
Rare opportunity to own a fully renovated, income-producing 2-flat in the heart of Jefferson Park! Offering more than 3,000 square feet of living space and impressive rental income, this turnkey property is ideal for investors or owner-occupants looking to supplement housing costs with rental income. Unit 1 is currently rented for $3,200/month, while the beautifully remodeled second-floor unit offers projected rental potential of approximately $2,900/month, bringing total pro forma rental income to approximately $6,100/month or $73,200 annually. Each unit features three bedrooms, one full bath, abundant natural light, and separate utilities including Central Air. The first-floor unit offers hardwood floors, a generous living and dining space, and a spacious kitchen with white cabinetry, stainless steel appliances, granite countertops, and an oversized island with seating for four. The second-floor unit was remodeled just this year and features luxury vinyl flooring, a gorgeous new kitchen with white cabinetry, quartz countertops and new stainless steel appliances, plus its own in-unit washer and dryer and updated bathroom. Finally, the finished lower level with a washer / dryer, large family room, additional non-conforming bedroom and full bath provides exceptional additional living space. 3 floors and 3 bathrooms - one on each level! Major property improvements include a newer roof, drain tile and sump pump. Outside, enjoy a fully paved, low-maintenance backyard, two-car garage, and additional parking pad. Conveniently located near the Jefferson Park Blue Line and Metra stations, I-90/94, O'Hare, schools, parks, shopping and restaurants. With substantial current and projected rental income, extensive recent improvements, separate utilities, and excellent long-term potential, this is a truly turnkey opportunity in one of Chicago's most desirable Northwest Side neighborhoods.

5351 W Foster Avenue, Chicago

$995,000
6 Beds ⋅ 3 Baths ⋅ 12747849 MLS ⋅ NEW Status
This one is special! Truly unique, move in ready, classic Andersonville vintage brick 2 flat with custom condo quality owners unit 3bed/2bath duplex down and sunny vintage 3bed/1bath rental up! Unlike every other 2 flat in the city, this one has fantastic light & views due to it's unique lot next to 4 SFH to the west with leafy backyard gardens with wide setbacks and NO alley or garages! A unique, mid-block position on this quiet, one-way tree lined street gives you a nice backyard view & sunny, south facing garden! Bright & light filled units -- even on the 1st floor. A slightly extra long 130' lot with an adorable brick 2 car garage with a fully fenced yard with just enough grass & a paver patio are ready for your kids, pets and parties! So much has been done to this c. 1913 gem and yet so much could still be done to give it a 21st century upgrade. Would make an amazing investment property for a live in owner or perfect candidate for SFH deconversion. Basement has a side AND back entry with potential to add a 3rd rental unit/ADU. HUGE Upgrade - all new lead free water service installed 2026! Original woodwork, hardware, built-ins, and vintage details remain beautifully intact throughout! .3 miles to Bryn Mawr red line, .7 miles to Peterson Metra, .7 miles to Hollywood Beach & lakefront trails. Incredible walkable location a block and a half off Clark St. with some of the north side's best cafes, dining, shopping & entertainment just steps from your front door! See additional docs for list of improvements.

1335 W Hollywood Avenue, Chicago

$675,000
6 Beds ⋅ 3 Baths ⋅ 12766920 MLS ⋅ NEW Status
Legal 2-unit frame multi-family building on a 3,125 sq ft lot with a nice backyard and 2-car garage. Attractive greyish exterior with roof extension/dormer. Substantially rehabbed in 2020 with new mechanicals (furnaces and water heaters in both units from 2020), updated appliances, and targeted renovations. Unfinished lower-level houses electrical panels plus Unit 1's furnace and water heater. Separate entrances. Unit 1 (first floor): 3 bed / 1 bath, approximately 1,200 sq ft. Fully rebuilt to the studs with a complete remodel. In-unit washer/dryer toward the rear near the third bedroom and back exit to the porch/staircase. Quiet mechanicals located downstairs. Unit 2 (duplex-up): 3 bed / 2 bath. approximately 2400 sq ft. Own entrance via staircase; and shortcut staircase entrance to upper level. Main level features a large living room with tall windows and strong natural light overlooking the avenue, laundry room, bedroom with normal closet space, kitchen with newer white Shaker upper cabinets / dark brown lower cabinets and 2020 appliances, generous dining room surrounded by windows, and rear exit. Upper level with secondary access via rear staircase includes a craft station with cabinetry and sink, access to a private wooden deck overlooking the property, second bedroom with normal closet space, full bath with vintage green tile and Hollywood-style circular bulbs (partial upgrades only during rehab-not fully gutted), and a very large master bedroom with vanity fireplace, nice closet space, and closeted mechanicals (unit's furnace and water heater). This unit received targeted renovations- kitchen updates, and first-floor bath work; remaining areas fixed up. Ideal for owner-occupant (live in one, rent the other) or investor. Both units available for viewing. Unit 1: May 31st, 2027, lease, $1995 with tenant planning to move. Rent projections $2400. Unit 2: Freshly vacated, rent projections $3500. Location in the 60647 area near North Avenue offers access to neighborhood amenities.

1621 N Talman Avenue, Chicago

$1,310,000
6 Beds ⋅ 6 Baths ⋅ 12766902 MLS ⋅ NEW Status
Introducing a stunning new construction two-flat in the heart of historic Pilsen. Designed with flexibility and lifestyle in mind, this beautifully crafted property is ideal for multigenerational living, owner-occupants seeking rental income, or savvy investors looking for a standout opportunity in one of Chicago's most vibrant neighborhoods. The garden unit is over 1200 sf offering 2 bedrooms and 2 full baths. The duplex up is over 2430 sf and lives like a single-family home, including 4 bedrooms and 3.5 baths. Both homes are filled with natural light and complemented by beautifully designed and well-proportioned kitchens with open concept large family rooms connected to outdoor space, in-unit laundry and generous storage. Both kitchens include white oak cabinetry, quartz countertops, decorative backsplashes and stainless-steel appliances including beverage centers. Abundant private outdoor space offers true indoor/outdoor living including gas, electricity, and water hookups. The garden unit has 2 outdoor living spaces including the shared backyard and private front patio while the duplex unit highlights vaulted ceilings with a large custom designed enclosed deck off the family room extending the living and entertaining space adding a dramatic finishing touch. The back patio offers a retreat off the primary bedroom with city skyline views. With excellent closet space, refined design details, and quality craftsmanship throughout, these homes deliver both comfort and sophistication. Enjoy the best of Pilsen just outside your door-renowned dining, easy access to transportation, neighborhood events, and the unmistakable energy of the community. This is a rare opportunity to own a thoughtfully designed, expertly built new development in an unbeatable location.

1118 W 19Th Street, Chicago

$425,000
6 Beds ⋅ 2 Baths ⋅ 12766266 MLS ⋅ NEW Status
Welcome to 2753 W 38th St, a great investment opportunity located in the Brighton Park neighborhood of Chicago. This property offers excellent potential for investors looking to add to their portfolio or owner-occupants seeking a property with existing rental income. The property currently has 1 tenant on a month-to-month basis one did just move out , it was generating a combined monthly rental income of $3,050 ($1,500 and $1,550). The existing rental income provides an immediate income stream while offering the new owner flexibility with future plans for the property. The property is well insulated, including the interior and exterior walls, floors, and ceilings, providing added comfort and energy efficiency throughout the home. An adjacent, separate lot is also available and can be purchased separately or together with the property it is not included in the price. This additional parcel provides an excellent opportunity for a buyer looking for additional land, potential future development, parking, or other permitted uses. Conveniently located near major streets, public transportation, shopping, restaurants, schools, parks, and other neighborhood amenities. The property provides easy access to surrounding Chicago neighborhoods and major transportation routes. This is an excellent opportunity for an investor seeking an income-producing property with additional land available, or for a buyer looking for a property with multiple options for future use. Schedule your showing today and explore the possibilities this property and adjacent lot have to offer. Property is an estate sale being SOLD AS IS. Property was reactivated due to issues with buyers loan.

2753 W 38Th Street, Chicago

$449,000
6 Beds ⋅ 3 Baths ⋅ 12766153 MLS ⋅ NEW 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

$849,900
6 Beds ⋅ 5 Baths ⋅ 12763542 MLS ⋅ NEW Status
Legal two-unit building in Irving Park. The property consists of two three-bedroom units: a three-bedroom, two-bath unit and a three-bedroom, one-bath unit. A non-conforming garden-level unit with a full bathroom adds extra flexibility. The property is eligible by right for the Chicago ADU program, offering a buyer a path to add value by creating an additional legal unit. The garden-level space currently has its own bathroom and electric service. The existing garden unit is non-conforming, and any future use or conversion would need to be researched and approved by the buyer. Buyer to verify zoning, ADU eligibility and compliance. This property is perfect for house hackers looking to start their investment journey using conventional financing. The layout suits owner-occupants who want to live in one unit and offset the mortgage with the other, and investors seeking long-term rental demand. There is room to add value through interior renovations and rent optimization. The property is currently owner-occupied with no tenants in place, so it's an easy move-in. A new owner can live in one unit, set market rents on the other, and reposition the asset through strategic capital improvements. The property is in the heart of Irving Park, with tree-lined blocks / nearby parks / dining and shopping on Irving Park Road, Elston or Milwaukee. It has proximity to the Blue Line, Metra, or CTA bus routes, strong tenant demand and long-term appreciation drivers.

3634 N Troy Street, Chicago

$899,900
9 Beds ⋅ 6 Baths ⋅ 12765362 MLS ⋅ NEW Status
FOR A LIMITED TIME, THE DEVELOPER IS OFFERING A SELLER CONTRIBUTION EQUAL TO TWO POINTS OF THE PURCHASE PRICE THAT BUYERS CAN USE TOWARD AN INTEREST-RATE BUYDOWN. Introducing a stunning newer construction 3-unit building in the heart of Woodlawn-an exceptional, income-producing investment opportunity in one of Chicago's most rapidly evolving neighborhoods. With two units currently rented and Unit #3 vacant, this property offers immediate cash flow with the added flexibility for an owner-occupant or premium lease-up. This beautifully designed building features a total of 9 bedrooms and 6 bathrooms, thoughtfully crafted to blend modern sophistication with everyday functionality. Each unit showcases design-forward interiors, including curated kitchens with custom cabinetry, decorative wood panel accents, professional-grade appliances, quartz countertops, and sleek designer backsplashes. Engineered hardwood flooring flows throughout, creating a cohesive and elevated living experience. The spacious primary suites serve as a true retreat, complete with spa-inspired bathrooms featuring oversized frameless glass showers and high-end fixtures. Additional highlights include closet systems, sprinkler systems, and dedicated parking. Perfectly positioned on a picturesque Woodlawn block, this property offers unbeatable access to some of Chicago's most iconic destinations, including the University of Chicago, Jackson Park harbor, the lakefront and beaches. Just moments away, the highly anticipated Obama Presidential Center continues to drive growth and long-term value in the area. Residents will also enjoy proximity to local dining, coffee shops, grocery stores, and the vibrant energy of nearby Hyde Park. Whether you're expanding your portfolio or seeking a turnkey investment with strong rental potential, this is a rare opportunity to own a high-performing asset in a thriving community. Photos are of the model unit at 6508 S. Ingleside Additional offering: 6500-6508 S. Ingleside Ave. is also available, consisting of four (4) luxury, new construction 3-unit buildings featuring spacious 3 bed / 2 bath layouts with condo-quality finishes throughout. The properties may be purchased individually or as a portfolio package of two, three, or all four buildings-presenting a unique opportunity to scale in one of Chicago's most promising submarkets. Contact me today to schedule your private showing!

6506 S Ingleside Avenue, Chicago

$899,900
9 Beds ⋅ 6 Baths ⋅ 12765356 MLS ⋅ NEW Status
FOR A LIMITED TIME, THE DEVELOPER IS OFFERING A SELLER CONTRIBUTION EQUAL TO TWO POINTS OF THE PURCHASE PRICE THAT BUYERS CAN USE TOWARD AN INTEREST-RATE BUYDOWN. Introducing a stunning newer construction 3-unit building in the heart of Woodlawn-an exceptional, income-producing investment opportunity in one of Chicago's most rapidly evolving neighborhoods. With two units currently rented and Unit #3 vacant, this property offers immediate cash flow with the added flexibility for an owner-occupant or premium lease-up. This beautifully designed building features a total of 9 bedrooms and 6 bathrooms, thoughtfully crafted to blend modern sophistication with everyday functionality. Each unit showcases design-forward interiors, including curated kitchens with custom cabinetry, decorative wood panel accents, professional-grade appliances, quartz countertops, and sleek designer backsplashes. Engineered hardwood flooring flows throughout, creating a cohesive and elevated living experience. The spacious primary suites serve as a true retreat, complete with spa-inspired bathrooms featuring oversized frameless glass showers and high-end fixtures. Additional highlights include closet systems, sprinkler systems, and dedicated parking. Perfectly positioned on a picturesque Woodlawn block, this property offers unbeatable access to some of Chicago's most iconic destinations, including the University of Chicago, Jackson Park harbor, the lakefront and beaches. Just moments away, the highly anticipated Obama Presidential Center continues to drive growth and long-term value in the area. Residents will also enjoy proximity to local dining, coffee shops, grocery stores, and the vibrant energy of nearby Hyde Park. Whether you're expanding your portfolio or seeking a turnkey investment with strong rental potential, this is a rare opportunity to own a high-performing asset in a thriving community. Additional offering: 6500-6508 S. Ingleside Ave. is also available, consisting of four (4) luxury, new construction 3-unit buildings featuring spacious 3 bed / 2 bath layouts with condo-quality finishes throughout. The properties may be purchased individually or as a portfolio package of two, three, or all four buildings-presenting a unique opportunity to scale in one of Chicago's most promising submarkets. Contact me today to schedule your private showing!

6508 S Ingleside Avenue, Chicago

$579,000
4 Beds ⋅ 3 Baths ⋅ 12764061 MLS ⋅ ACTIVE Status
NEW CITY! If you lived here-you'd be enjoying a healthier, more affordable, and comfortable lifestyle with less maintenance! Come your our MODEL HOME in what will be Chicago's largest sustainable community. Excellent location, minutes from the loop, Midway, transit and just a block from beautiful Historic Sherman Park. Greenline Homes, an award-winning developer, is transforming this neighborhood into a sustainable community with homes that truly work for their owners. Perfect for first-time buyers! Rental income helps make your home more affordable, and it's great for multigenerational buyers who want accessibility without sacrificing their lifestyle. This brand-new all-electric two-flat blends beautiful design, thoughtful layouts, cutting-edge building science, and the best materials and equipment available. On the main level, the primary duplex-up unit features a versatile bonus room, perfect for a high-end home office, 3rd bedroom, or recreation room. Upstairs, a private rear balcony, large enough for gatherings and dining, is directly off the great room, creating a seamless indoor-outdoor living experience. The stunning ADA-accessible first-floor unit offers a spacious retreat, ideal for multi-generational living or generating high-value rental income to boost affordability. No compromises here-custom cabinetry, designer quartz, and induction cooking in a home designed for the future. Triple-pane windows ensure ultimate thermal comfort, and a fully paid-for solar PV system means near-zero utility costs without sacrificing style. The super insulated walls and roof make for a library-quiet interior. Plus, an energy recovery ventilator keeps fresh, filtered air flowing 24/7, even when the windows are closed, so you can still enjoy comfort and efficiency. Every detail, from the premium Hardie Board exterior to the EV-ready garage and gated intercom security, is designed for effortless, low-maintenance living. Experience a healthier, wealthier, and more comfortable lifestyle-your best life begins here. And the best part? More houses to come next door...

5236 S Bishop Street, Chicago

$699,000
5 Beds ⋅ 3 Baths ⋅ 12761153 MLS ⋅ ACTIVE Status
Exceptional opportunity to own a beautifully updated 2-flat in a prime Oak Park location-just a 1-minute walk to Rush Oak Park Hospital! This gorgeous property sits on a 40x170 lot and blends original architectural character with extensive modern updates throughout. Both units feature fresh paint, new appliances, updated flooring, custom cabinetry, beautifully tiled bathrooms, and new dual-zoned HVAC, while original hardwood floors and a stunning wood staircase preserve the home's timeless charm. The first-floor unit offers 2 bedrooms plus a spacious main living area, providing excellent flexibility and the potential to function as a 2+ bedroom layout. The second-floor unit features 3 bedrooms, 1.5 baths, generous living space, and its own private side entrance. Above the second unit is an enormous attic offering incredible additional space and endless possibilities. Outside, enjoy a massive fenced yard, large front and rear porches, and FOUR parking spaces conveniently located directly behind the property. Space is truly abundant inside and out! An outstanding option for related living, an investor looking to add a turnkey rental property to their portfolio or an owner-occupant looking to live in one unit while generating income from the other. With Rush Oak Park Hospital practically at your doorstep, easy expressway access, and shopping, dining, transportation, and neighborhood amenities within walking distance, the location is hard to beat. A beautifully updated Oak Park 2-flat offering character, versatility, income potential, and an incredible amount of space! Broker owned interest.

427 Wisconsin Avenue, Oak Park

$1,275,000
6 Beds ⋅ 3 Baths ⋅ 12763197 MLS ⋅ ACTIVE Status
Charming Andersonville 2-Flat with Owner-Occupant & Investment Potential Welcome to 1639 W Rascher Ave, a charming and versatile two-flat located in the heart of Chicago's highly sought-after Andersonville neighborhood. This classic Chicago property offers an excellent opportunity for an owner-occupant, multigenerational household, or investor looking to own in one of the city's most desirable and walkable communities. The property features spacious living areas, classic Chicago character, and a flexible layout that provides the opportunity to live in one unit while generating rental income from the other. With approximately 2,456 square feet of living space and a generously sized lot, there is plenty of room to make this property your own. Enjoy everything Andersonville has to offer just outside your door-from locally owned restaurants, cafes, shops and boutiques to neighborhood parks, community events and easy access to the lakefront. The surrounding residential streets offer a wonderful balance of city convenience and neighborhood charm, making this an appealing location for both families and professionals. The property's two-flat configuration provides multiple possibilities for the next owner: live in one unit and rent the other, accommodate extended family, or maximize its investment potential. Its location, size, and flexible layout make this a unique opportunity to own a piece of one of Chicago's most vibrant neighborhoods. Come experience the character, convenience, and lifestyle that make Andersonville such a special place to call home.

1639 W Rascher Avenue, Chicago

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