FINDING HOME IN CHICAGOLAND isn’t luck. it’s strategy.
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.

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Modeled housing cost
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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

$449,900
6 Beds 4 Baths 12730101 MLS NEW Status
Exceptional 4-Unit Investment Opportunity in Park Manor! Welcome to 7348 S. Vernon Avenue, a spacious all-brick multifamily property offering an outstanding opportunity for investors looking to expand their Chicago real estate portfolio. This well-maintained building features four residential units with a total of 6 bedrooms and 4 full bathrooms, plus a full basement offering additional storage and future possibilities. The property underwent significant improvements, including an updated boiler, electrical wiring, plumbing, kitchens, bathrooms, appliances, beautifully refinished hardwood flooring, and improvements to the enclosed porch area. Throughout the building, you'll find generously sized living spaces, hardwood floors, and beautiful original woodwork that preserves the character and craftsmanship of this classic Chicago property. Situated on a residential block in the desirable Park Manor community, the property offers convenient access to public transportation, neighborhood amenities, and major expressways, including I-90/I-94.The landlord currently pays gas and electric for the building/tenants, except Unit 1F pays its own electric. Whether you're an experienced investor or looking to add your next multifamily property to your portfolio, 7348 S. Vernon offers space, character, location, and income-producing potential all under one roof. Opportunities to acquire a four-unit brick building like this don't come along every day-schedule your private showing and discover the possibilities!

7348 S Vernon Avenue, Chicago

$619,000
7 Beds 4 Baths 12729584 MLS NEW Status
Rare 4-Unit in the Heart of Pilsen! Exceptional investment opportunity on an approximately 25' x 125' corner lot (per survey) with RT-4 zoning (buyer to verify). Rare opportunity to acquire a legal 3-unit PLUS a separate coach house in one of Chicago's most sought-after investment neighborhoods. Coach house with front door direct access to Wood Street, allowing it to function much like a standalone single-family home. The front building offers a spacious first-floor duplex-down with soaring ceilings and finished lower level, a rear first-floor 2-bedroom with excellent duplex potential, and a bright, sun-filled second-floor 2-bedroom. The coach house features its own private entrance, lofted ceilings, a 2-bedroom/1-bath layout, and a full unfinished basement offering exceptional storage and future expansion potential. Substantially renovated in 2003, the property features separate electric service and HVAC for all four units. Additional improvements include a front building roof replacement (approximately six years ago) and a new furnace and central air system in the coach house (2025). Offered AS-IS, the property is ready for thoughtful updating and presents an outstanding value-add opportunity. Lovely long-term tenants provide stable in-place income while offering significant upside through future renovations, lease optimization, and rent growth. Current Gross Income: $44,280/year ($3,690/month) Current Rent Roll * Unit 1F: 1BR/1BA duplex-down | $1,100/month | Lease through 5/31/27 * Unit 1R: 2BR/1BA | $700/month | Month-to-month * Unit 2F: 2BR/1BA | $690/month | Month-to-month * Coach House: 2BR/1BA | $1,200/month | Month-to-month Three of the four units are month-to-month, providing immediate flexibility to implement a value-add strategy while maintaining current cash flow. Ideally located in the heart of Pilsen, just steps from the vibrant 18th Street corridor featuring neighborhood favorites including 5 Rabanitos, Los Comales, Pizza Nova, and Carniceria Maribel. Conveniently located near the CTA Pink Line, UIC, the Illinois Medical District, and Downtown Chicago. First showings by appointment only July 10, 11 & 12. Buyer to independently verify zoning, legal unit count, redevelopment potential, and all property information.

1801 W 21St Place, Chicago

$670,000
5 Beds 4 Baths 12728975 MLS NEW Status
Good News! This Home Qualifies for the Cook County first time home buyer grant! Experience luxury living and exceptional investment potential with this stunning 2-unit property in the heart of Woodlawn. Built in 2021 and never lived in and upgraded in 2026 this vast and lavish residence offers the cutting edge in amenities and creature comforts. Experience the feel of brand-new construction with some of the highest forms of modern upgrades around. Featuring a spacious owner's duplex-up first floor unit paired with a fully independent, income-producing garden unit, this property is an outstanding opportunity for owner-occupants, investors, house hackers, or short-term rental strategies such as Airbnb. The expansive owner's duplex-up features 3 bedrooms, and 3 bathrooms. The open-concept floor plan features soaring 10-foot ceilings, oversized bay windows, abundant natural light, and premium 3/4-inch hardwood flooring throughout. The designer kitchen, complemented by it's spacious outdoor 15x19' deck showcases quartz countertops, stainless steel appliances, and a dramatic waterfall island that flows seamlessly into the spacious dining and living areas anchored by a beautiful fireplace which are flanked furthermore by picturesque Bay windows in the dining area to ensure consistent natural lighting. Upstairs, the spacious primary suite features a private ensuite bathroom, while the second bedroom and additional full bathroom provide comfort and flexibility for growing families. An in-unit LG washer and dryer add everyday convenience. Designed for entertaining, the home also features a custom wet bar with attached drinks refrigerator, and commercial-grade glass rinser to enhance the at-home mixologist cocktail connoisseur experience, creating a sophisticated focal point for gatherings. Premium finishes continue throughout the property with LED vanity mirrors, smart sensor automatic flush toilets, night-light dimmer switches, recessed exterior windows, and sound-deadening construction designed to enhance privacy and comfort. The fully finished garden unit offers its own private entrance and was designed as a truly independent living space. It features 2 bedrooms, 1 lavish full bathroom, quartz countertops, stainless steel appliances, its own 2-in-1 washer and dryer, separate HVAC system, and independent water service. The second unit provides excellent flexibility for long-term rental income, permitted short-term rental use, house hacking, or multigenerational living. The property is high efficiency gas and solar powered with privately owned solar panels, allowing the future homeowner to fully benefit from solar-generated electricity and greatly reduce their electric utility costs- make this property more energy efficient than its new construction neighbors. The solar panels are available to be included with the sale. Upon entering the second unit you will be greeted by a newly renovated living room fitted with a hydraulic mounted large flat screen TV and chef's kitchen fitted all-new stainless appliances with 42 inch cabinets which have been painted a luxurious satin money-green A newly constructed 2-car garage is also EV-ready, with the option for the builder to install a Tesla or other electric vehicle charger upon request. Enjoy outdoor living on the rear deck and patio, which connect seamlessly to the kitchen through two large glass patio doors, creating an inviting indoor-outdoor living experience while bringing abundant natural light into the home. Located in Woodlawn near transportation, parks, dining, hotels, and ongoing neighborhood development, the property is also conveniently positioned near the Obama Presidential Center, adding to the area's appeal for homeowners and investors. With luxury finishes, two independent living spaces, solar panels, income-producing potential, and a prime Woodlawn location, this property offers an exceptional combination of lifestyle and investment opportunity.

6547 S Evans Avenue, Chicago

$750,000
5 Beds 4 Baths 12711401 MLS NEW Status
Exceptional opportunity to own a beautifully maintained and thoughtfully updated two-flat on one of Avondale's most desirable tree-lined streets. Whether you're an investor seeking a turnkey income property or an owner-occupant looking for a flexible multi-unit living arrangement, this property offers incredible versatility, thoughtful updates, and future upside. The sun-filled owner's unit lives like a single-family home, spanning the second and third floors and featuring 3 bedrooms, a den, 2 full bathrooms, two separate living rooms, a formal dining room, and in-unit laundry. The attic has been completely transformed into a luxurious primary suite complete with a spacious bedroom, full bathroom, laundry, and an additional living space-creating the perfect private retreat, home office, nursery, or lounge. The first-floor unit offers 2 bedrooms plus a den, a formal dining room, one full bathroom, basement laundry, and a private rear deck, making it an attractive rental or ideal space for extended family. Step outside and enjoy one of the home's most impressive features-a beautifully landscaped backyard with a large patio, perfect for entertaining, grilling, gardening, or simply relaxing on warm Chicago evenings. The property also includes one rear parking space, a valuable convenience in this sought-after neighborhood. It's a truly special outdoor space that's been lovingly cared for over the years. For buyers looking to add even more value, there is potential to duplex the first-floor unit into the basement (buyer to verify feasibility), creating additional living space and increasing future income potential. Perfectly situated in the heart of Avondale, you'll love being just minutes from neighborhood favorites including Brands Park, the Chicago Riverwalk Trail, Sleeping Village, Avondale Bowl, Revolution Brewing's Kedzie Taproom, Loaf Lounge, and an ever-growing collection of acclaimed restaurants, coffee shops, and breweries. Commuting is effortless with easy access to the CTA Blue Line, multiple bus routes, and I-90/94, putting downtown Chicago, Logan Square, and O'Hare all within easy reach. Sunny, spacious, meticulously maintained, and filled with opportunity, this is a rare chance to own a move-in-ready two-flat in one of Chicago's fastest-growing and most desirable neighborhoods. Whether you're looking for a turnkey investment, a flexible owner-occupied property, or a home with room for extended family, 3748 N. Spaulding is a property you won't want to miss.

3748 N Spaudling Avenue, Chicago

$329,000
7 Beds 2 Baths 12727628 MLS NEW Status
NEWLY RENOVATED 2-FLAT | CONDO-QUALITY FINISHES | 7 BEDROOMS TOTAL Welcome to 6940 S. Bishop, a beautifully renovated two-flat that blends timeless architecture with sophisticated, modern design. Thoughtfully redesigned from top to bottom, this impressive property offers seven total bedrooms across two spacious apartments, making it an exceptional opportunity for an owner occupant, multigenerational household, or savvy investor seeking quality and versatility. The first-floor residence features 3 bedrooms and 1 full bathroom, while the second-floor residence offers 4 bedrooms and 1 full bathroom. Both units showcase true condo-quality craftsmanship, including fully refinished hardwood flooring, designer accent walls, elegant millwork and wainscoting, and modern LED lighting that creates a polished, contemporary atmosphere throughout. The kitchens are designed to make a statement, featuring rich, dark cabinetry, sophisticated quartz countertops, and durable vinyl kitchen flooring that complements the upscale finishes while providing everyday functionality. Each bathroom has its own distinctive personality, with unique color palettes and designer-inspired finishes. One features striking gold fixtures and accents, while the other incorporates sleek black finishes, creating two distinctly stylish spaces. Beyond the individual units, the property continues to impress with a completely renovated common hallway, giving the building a fresh, cohesive appearance from the moment you enter. The combination of hardwood flooring, contemporary lighting, accent walls, and detailed millwork gives this property the look and feel of a high-end condominium while maintaining the flexibility and investment potential of a two-flat. The basement is unfinished, offering valuable additional space for storage and future possibilities. With its extensive renovation, spacious bedroom count, designer finishes, and attention to detail, 6940 S. Bishop is a turnkey opportunity that delivers style, functionality, and long-term value. This is not your typical renovated two-flat-the quality and design details set it apart.

6940 S Bishop Street, Chicago

$389,000
6 Beds 3 Baths 12724345 MLS NEW Status
Rare Incredible opportunity to own a well maintained Legal 2 Unit with Related Living in the Hot Little Village-La Villita/North Lawndale Neighborhood. 1st Floor has Living Room, Eat-In Kitchen, 3 Bedrooms & Full Bath. 2nd Floor has Open Concept Eat-In Kitchen with Separate Living Room area and large bedroom with sitting area rare find in the area and Full Bath. 3rd Floor Related Living has open concept as well with separation of the rooms, Kitchen, Living Room & Dining Area. Large 1 Bedroom with closets. Utilities are separate, GFA, Water Heaters & Electrical Panel in each unit. Central AC in 1st & 2nd Floor Units, plus all units have in unit laundry. Remote control gates to front exterior parking for 4 cars. Note, over $30k spent on New Water line out to the street. Property next door (2515) is also available for sale wrought iron fence separates/connects properties. You can purchase both properties and keep the separation fence or Owner will fence off. Rents are low due to long term tenants. Bring your renovation ideas to increase rental income. Property is being sold "AS IS" Located right off of El Arco de La Villita/26th Street Commercial Corridor-one of the highest-grossing shopping neighborhoods in the city, filled with Restaurants, Shopping, Banks, Street Vendors, Murals-Minutes from I-55 & I-290 Expressways, Public Transportation, Midway Airport, El Train-Pink Line, Pilsen, Ogden Avenue for a quick drive to Downtown Chicago and all that the City has to offer.

2519 S Kedzie Avenue, Chicago

$375,000
8 Beds 2 Baths 12639070 MLS NEW Status
Historic jumbo Chicago Greystone in West Garfield Park, recently operating at a 9.5-10 percent cap rate. This spacious 2-unit property is zoned RT-4 and eligible for the City of Chicago's ADU Program, offering strong current income, a vacant unit ready for immediate market-rate rental, and compelling value-add potential for investors looking to increase long-term returns. The first-floor unit features 3 bedrooms and 1 bathroom. The second-floor unit features 5 bedrooms and 1 bathroom. All bedrooms are generous in size, and both units offer huge living rooms, large dining rooms, and expansive enclosed rear porches. Both units went through extensive cosmetic renovations in 2024, including new bathrooms, lighting, flooring, paint, and stainless steel stove and refrigerator appliances. Unit 1 received copper plumbing and electrical updates, as well as a new furnace and water heater in 2024. Unit 2 received copper plumbing, electrical updates, and a furnace replacement in 2021, along with a new water heater in 2023. Additional improvements include a new basement furnace in 2024, several new windows in 2024, roof maintenance and repairs in 2024, and a new sump pump installed in March 2026. Unit 1 is currently rented to a CHA tenant for $1,600/month, with 89% paid by CHA. Unit 2 is currently vacant and ready for immediate market-rate rental. It was recently rented for $2,519/month through CHA, and the seller has active interest from new CHA tenants at $2,850/month. Tenants pay heat, gas, and electric. With much of the framework already in place, the basement provides a unique opportunity to further maximize the property's long-term income potential. The basement offers 8-foot ceilings, three separate entrance/exit points, and is currently framed out as a spacious 1-bedroom unit. Prior kitchen plumbing locations are visible, and the bathroom area is framed out with prior drain locations visible for a sink, toilet, and shower. The layout also allows for separate access to storage, mechanicals, and a future laundry area. The rear of the property includes a concrete parking pad inside a fully fenced yard. This is a solid investment opportunity with size, character, recent updates, existing rental income, separate utilities, and room to add future value.

4225 W Jackson Boulevard, Chicago

$749,000
7 Beds 3 Baths 12713816 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

$565,000
5 Beds 3 Baths 12725191 MLS ACTIVE Status
Welcome to 3623 S. Emerald Avenue - a beautifully updated brick two-flat in the heart of Bridgeport, showcasing a classic Chicago facade, bold yellow entry doors, and bright, modern interiors throughout. Thoughtfully renovated, this property is ideal for investors and owner-occupants alike, offering style, comfort, and income potential in one of the city's most walkable historic neighborhoods. Each of the two units offers a smart, modern layout with tall ceilings, hardwood floors, and oversized windows that fill the space with natural light. Kitchens are appointed with rich espresso cabinetry, granite countertops, and stainless steel appliances, while updated bathrooms feature contemporary finishes, sleek vanities, and walk-in showers for true turnkey appeal. Both units include central air conditioning for year-round comfort. The finished lower level adds valuable living space, including a flex room and full bathroom - perfect for a home office, guest suite, or recreation room. A shared laundry area adds everyday convenience, and a 2-car exterior parking pad provides rare off-street parking in the city. Located in one of Chicago's most vibrant and historic neighborhoods, you'll enjoy exceptional walkability to local dining, coffee shops, parks, and community hotspots. Stroll to Armour Square Park, catch a game at Guaranteed Rate Field, or hop on nearby CTA buses and the Sox-35th Red Line stop for an easy commute. Quick access to I-90/94 and I-55 makes getting around the city seamless. Whether you're looking to live in one unit and rent the other or expand your investment portfolio, 3623 S. Emerald Avenue delivers the perfect blend of location, character, and opportunity.

3623 S Emerald Avenue, Chicago

$1,225,000
9 Beds 6 Baths 12725597 MLS ACTIVE Status
Welcome to the Calumet Collection, Magical Storybook Street Setting, Magazine Caliber, Simply Spectacular. Expansive footprint New Construction 3 flat all 3 bedroom 2 baths Exceptional Elegance, Intelligent Design, Floor to Ceiling Windows, Professional Fully Appointed Slim Line Sleek Kitchen Cabinetry, Under Cabinet Lighting, Integrated Stainless Steel Appliances, Quartz Island Full Back Splash & Waterfall Edge. Custom Mill Work, Wet and Dry Bars, Premium Wide Plank White Oak Hardwood Floors, Acoustic Panel Feature Wall with Media Console, Cohesive Design offering relief from ordinary, sequestered primary suite, lifestyles primary bathroom offer Opulent oversized Shower w/ Frameless Glass, Double Vanity, Custom Mirrors & Niches paired with designer plumbing fixtures. Professional closet organizers throughout. Unit 3 features interior Floating Staircase to Loft Bonus room with Wet Bar and Cantilevered Roof Deck equipped with gas, water, power completed in composite with option to expand offers Sensational City Views plus Additional Front Glass Terraces, rear patio and 3 Car Covered Carport Urban Intimacy w/ Hyper Convenience Experience excellence. Hands on Veteran developer includes 1 year builder warranty. Hyper Convenient, AAA Trophy Piece Perfect Turnkey, Owner Occupied, Investor or 1031. This is part of a 3 building series. This is exceptional property and location. IMMEDIATE Delivery. Pictures are from actual project. Projected Monthly $9650/ $115,800 Annual/ 7.8 CAP

4130 S Calumet Avenue, Chicago

$850,000
5 Beds 2 Baths 12722368 MLS ACTIVE Status
Located in the heart of Avondale, this well-maintained corner brick 2-flat with a non-conforming garden unit offers exceptional flexibility for investors, owner-occupants, short-term rental opportunities, or a future single-family conversion. Just steps from neighborhood favorites, this prime location enjoys strong tenant demand and is situated on a beautiful, tree-lined block with easy access to the Blue Line and expressways. Filled with natural light, the spacious second-floor unit features three bedrooms and one bath, a refreshed kitchen with white shaker cabinetry and quartz countertops, and a thoughtful blend of hardwood flooring, wood-look tile, and luxury vinyl plank. Stylish window treatments and a private rear porch. The first-floor unit offers two bedrooms, an open-concept living and dining area, and an updated kitchen with white shaker cabinetry and quartz countertops. A charming rear porch extends the living space and has made this unit a guest favorite on Airbnb. The spacious non-conforming garden unit is beautifully finished with one bedroom, a breakfast bar, a large walk-in shower, and a built-in desk-Seller used as their personal in-town unit. All three units feature central heat and air conditioning, in-unit laundry, and updated finishes. Outside, enjoy a nicely landscaped backyard and an oversized detached contractor's garage with ample storage and workspace. With numerous improvements throughout, this turnkey property is a solid investment opportunity in one of Chicago's most sought-after neighborhoods and ready to generate income from day one. (Seller is a licensed Real Estate Broker in the State of Illinois and a Wisconsin REALTOR, but is not the listing agent.)

2857 W Fletcher Street, Chicago

$599,900
5 Beds 5 Baths 12723960 MLS ACTIVE Status
Say hello to 1443 S. Trumbull, one of seven new construction two-flats coming to North Lawndale-where thoughtful design and elevated everyday living come together in a fresh, modern way. From the moment you arrive, the blend of brick and Hardie siding sets a strong, contemporary tone for what's inside. The home is designed around how people actually live-open, connected spaces, abundant natural light, and finishes that feel cohesive from room to room. Wide-plank LVT flooring runs throughout, paired with 5" baseboards and crown molding for an elevated aesthetic. The kitchen is the heart of it all-anchored by a striking black-and-white cabinetry contrast that brings a timeless, architectural edge. Quartz countertops, a large central island, custom cabinetry, and a full GE stainless steel appliance package come together to create a space built to be a conversation starter. From the kitchen, the space naturally opens into the family room-centered around a sleek fireplace and framed by expansive west-facing windows that draw in soft afternoon light. Built-in nooks are thoughtfully placed beside the windows, creating a quiet space to sit, reset, or simply take in the view. From here, the layout flows directly onto the rear deck. Upstairs, the primary suite is designed as a private escape. The spa-inspired bath features a walk-in glass shower with full-body sprayers, a dual vanity, and a freestanding soaking tub, paired with curated finishes from Kohler, Delta, and Signature Hardware. Two additional bedrooms and a second-floor laundry area complete the level with everyday practicality in mind. The garden unit adds incredible flexibility with 2 bedrooms, 2 full baths, and a private entrance-ideal guest or house-hacking opportunity: live comfortably in the main residence while offsetting your mortgage with income from the garden unit. A two-car garage and a spacious backyard round out the home, offering both convenience and room to enjoy. Located near Douglas Park and the Garfield Park Conservatory, with quick access to I-290, the CTA Green and Pink Lines, and just minutes from the West Loop and Downtown Chicago-this home places parks, culture, and city energy all within easy reach. MODEL HOME: 2435 W Congress Pkwy

1443 S Trumbull Avenue, Chicago

$799,000
6 Beds 4 Baths 12702247 MLS ACTIVE Status
Welcome to this absolutely stunning & unique 2-unit home nestled on a quiet tree-lined street in prime East Garfield Park, less than a block from the $42M newly announced Madison Street Athletic & Cultural Complex. Must see to really appreciate this a fully reimagined frame/brick home showcasing meticulous craftsmanship and high-end designer finishes throughout. Unlike in most multi-unit properties, the upstairs duplex lives like a sophisticated single-family residence with great entertaining space, high ceilings, formal dining, along with 4 bedrooms and 2.5 baths. The main upstairs unit features a spa-inspired primary bath suite that is nothing short of true luxury. The first floor offers a bright open-concept layout, anchored by a chef's kitchen with 36-inch range, hidden walk-in pantry, wine fridge, dramatic waterfall island, custom cabinetry, and premium SS appliances, including a second, separate beverage center. There are also custom built-in cabinets in the dining room, as well as crafted shelving & an electric fireplace wall with recessed TV in the Family room that all come together beautifully with the gleaming Amish-grade hardwood floors and custom lighting throughout that helps create a warm and cozy environment. Heading out from the kitchen is an amazing mudroom that leads straight out to the newly built metal/concrete raised back deck and cozy landscaped back yard that creates a refined space for entertaining or relaxing. The stamped and stained concrete in the back add to the experience. This home has been beautifully and thoughtfully renovated to enhance the character and charm while being completely updated to exceed today's standards. In addition to the upstairs luxury home, it also has an amazing garden unit that will generate more than enough income to cover property taxes, maintenance, utilities, insurance, and even some debt coverage on the loan. This garden 2 bed/1 bath unit is no exception to quality, and will make for an ideal rental, in-law suite, guest quarters, nanny suite, work space or there's potential to expand the upstairs unit to create an even larger single family home. The garden simplex has 2 bedrooms, 1 modern bath with a tub, a bright and airy living room, a separate dining area, a beautiful custom kitchen with new SS appliances and quartz counters, not to mention in-unit laundry hook-up and warm porcelain tile throughout. All of the mechanicals are new and include new copper water service, all new underground plumbing with backflow prevention valve, all new 400 Amp electric, each unit has separate energy efficient furnaces, A/C's and individual tankless hot water heaters. New rood, new gutters, new siding, spray insulation for added efficiency, all new energy efficient windows, and a new heated flat-roof garage that could be converted to a rooftop deck. There is simply too much to list.

2839 W Monroe Street, Chicago

$899,000
9 Beds 6 Baths 12724368 MLS ACTIVE Status
Your home should work harder for you. This brand-new construction Three Flat is perfect for first-time buyers and those seeking low-maintenance ownership with income, accessibility, affordability, or multigenerational living. Built by an award-winning home builder this high-performance, all-electric, three-unit building combines elegant design with cutting-edge building science. Every detail, from the premium Hardie Board exterior to the designer interior and gated intercom security, is crafted for effortless, low-maintenance living. All three units offer a condo-quality 3 Bedroom + 2 Bath layout upstairs with a with East facing great rooms with a glimpse of the new Obama Presidential Library from the top floor primary unit. Each unit also features a chef's kitchen with custom cabinetry, quartz countertops, and a premium induction ranges. Three Parking spaces in the rear. Live in one unit and generate high-value rental income to enhance your affordability.Each Greenline Home is appointed by a designer with tastemaker-grade finishes. Embrace custom cabinetry, designer quartz, and induction cooking in a home designed for the next 100 years, not the last. With triple-pane windows for ultimate thermal comfort and a fully paid-for solar PV system, enjoy ultra low utility costs without compromising on lifestyle. Your comfort and investment in this home will last for generations. Experience a healthier, wealthier, and more comfortable lifestyle-your best life begins here. Schedule your showing today to explore Chicago's best-priced new construction.

6312 S Champlain Avenue, Chicago

$589,000
4 Beds 3 Baths 12724342 MLS ACTIVE Status
Your home should work harder for you. This brand-new construction Two Flat is perfect for first-time buyers and those seeking low-maintenance ownership with income, accessibility, affordability, or multigenerational living. Built by award-winning Greenline Homes, this high-performance, all-electric, two-unit building combines elegant design with cutting-edge building science. Every detail, from the premium Hardie Board exterior to the EV-ready garage and gated intercom security, is crafted for effortless, low-maintenance living. The primary unit on the second floor offers a condo-quality 2 Bedroom + 2 Bath layout The unit features a chef's kitchen with custom cabinetry, quartz countertops, and a premium Induction range. An expansive private balcony extends from the great room, offering a seamless indoor/outdoor living experience.The stunning grade-level accessible first-floor offers a easy to rent 2 Bedroom + 1 Bath Layout that interfaces well with the private rear yard. This unit provides a spacious retreat, perfect for multi-generational living or generating high-value rental income to enhance affordability. Each Greenline Home is appointed by a designer with tastemaker-grade finishes. Embrace custom cabinetry, designer quartz, and induction cooking in a home designed for the next 100 years, not the last. With triple-pane windows for ultimate thermal comfort and a fully paid-for solar PV system, enjoy near-zero utility costs without compromising on style. Your comfort and investment in this home will last for generations. Experience a healthier, wealthier, and more comfortable lifestyle-your best life begins here. Schedule your showing today to explore Chicago's best-priced new construction.

6553 S Rhodes Avenue, Chicago

$885,000
9 Beds 7 Baths 12723988 MLS ACTIVE Status
Prime Woodlawn Investment Opportunity! Invest in the growth of Chicago's historic Woodlawn neighborhood with this meticulously maintained, condo-quality 3-unit building. Perfectly positioned just blocks from the Obama Presidential Center, this turn-key property is an exceptional opportunity to owner occupy or invest, offering high-end rental income and significant long-term appreciation potential. Property Highlights: Optimal Unit Mix: Three highly desirable, spacious units, each featuring a 3-bedroom, 2-bathroom layout. Premium Floor Plans: The first-floor unit is a sprawling duplex-down, providing massive living space that lives like a single-family home. Condo-Quality Finishes: Beautiful interior details, including exposed brick walls, add character and charm to attract premium tenants while minimizing upkeep. Turn-Key Mechanicals: All major systems-including plumbing, electrical, HVAC have been modernized, and recent tuckpointing, ensuring low maintenance and peace of mind for the next owner. Unmatched Location & Upside: Situated at the epicenter of a multi-billion dollar neighborhood transformation, this building sits directly across the street from a brand-new 8-unit development, signaling strong and continuous local investment. Residents enjoy an incredible quality of life with seamless access to DuSable Lake Shore Drive, the lakefront recreation trail, the renowned Jackson Park Golf Course, the beach, and the harbor. Plus, the vibrant shopping, dining, and entertainment of nearby Hyde Park are just minutes away. Don't miss this rare chance to own a strategic, cash-flowing piece of Woodlawn's exciting future!

1527 E 66Th Place, Chicago

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

1808 W Armitage Street, Chicago

$989,900
6 Beds 7 Baths 12688918 MLS ACTIVE Status
**Exceptional New Construction 3-Unit Investment Opportunity!** Don't miss this beautifully newly constructed brick and Hardie siding 3-unit building, designed with modern finishes, spacious layouts, and outstanding income potential. Whether you're an investor looking for a turnkey rental property or an owner-occupant seeking additional rental income, this property is ready for immediate occupancy after closing. The **first-floor unit** features **2 spacious bedrooms, a private office/den, and 2.5 bathrooms**, offering a flexible floor plan ideal for today's lifestyle. The **second and third-floor units** each offer **2 generously sized bedrooms and 2 full bathrooms**, with open-concept living spaces filled with natural sunlight. Each unit is thoughtfully appointed with: * Beautiful 42-inch kitchen cabinets * Elegant quartz countertops * Stainless steel appliance package * Durable laminate flooring throughout * Bright, sun-filled interiors with abundant natural light * In unit laundry Hook up Minutes from the train station,and expressway. Additional property features include a rear metal porch, wrought iron fencing, a private fenced yard, and secure gated private parking for residents. This turnkey property offers excellent rental income potential and is ready to be leased immediately or occupied upon closing. Investors are welcome! **Disclosure:** Owners of the LLC are licensed Real Estate Brokers in the State of Illinois.

2849 W Monroe Street, Chicago

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