View All Portage Park Chicago IL Homes with Pool House Listings

6 Beds ⋅ 3 Baths ⋅ 12712329 MLS ⋅ ACTIVE Status

Welcome to this legal 3 unit property located in the heart of the highly desirable Portage Park neighborhood. Enjoy the perfect blend of vintage charm and modern updates in this bright, spacious building on tree-lined Byron Street. Perfectly suited for an investor looking for strong rental yields or an owner-occupant looking to house-hack and have their tenants pay the mortgage! New siding (2026), Roof (2025), and all kitchens have been redone in the last 5 years! Unit 2 is vacant for an owner occupied buyer and Unit 1 and Unit G are leased through May 2027. Outdoors, you'll find a fully fenced-in backyard-ideal for summer gatherings or pets-and a secure, detached 2-car garage. An absolute walker's paradise! Enjoy an unbeatable location just a short stroll away from the historic Six Corners shopping, dining, and entertainment district. Commuting is a breeze with easy access to I-90/94, multiple Blue Line stations, and the Grayland Metra station just minutes away. Best of all, you are blocks from the expansive 40-acre Portage Park, featuring magnificent green space, playgrounds, athletic fields, and its famous Olympic-size pool. Don't miss out on adding this turnkey gem to your portfolio! Owner is a licensed real estate broker.

4824 W Byron Street, Chicago

$410,000

3 Beds ⋅ 2 Baths ⋅ 12221623 MLS ⋅ CLOSED Status

Charming Georgian home looking out to the park! If you're familiar with the huge neighborhood amenity and community gathering space that is Portage Park with its park district programming, softball fields, tennis and pickleball courts, playground, pool, and more then you'll appreciate the advantage this location offers. This home has spacious, separate living and dining rooms on the main level with well kept hardwood floors. Beyond you will find the kitchen and the 3rd bedroom (currently a play room) with an adjacent enclosed rear porch. Both upper bedrooms have nice size, and the lower level offers both a rec room as well as a large rear laundry / mechanical room with enough space to house an exercise studio or workshop as well. This all brick home is well maintained and provides opportunity for the new owner to either move right in or put their personal touch on it. It has a nice sized backyard and patio as well as a 2 car garage. You can also simply cross the street to travel by park paths to neighborhood spots like Portage Grounds and get a workout at LA Fitness. You'll find many restaurant options within a few blocks as well. Come take a look and celebrate the holidays with a home purchase!

4116 N Central Avenue, Chicago

$397,000

2 Beds ⋅ 2 Baths ⋅ 12100512 MLS ⋅ CLOSED Status

Portage Park, light filled bungalow, family owned since 1998. Move-in ready, immaculate home with HW floors throughout the first floor. The LR has a bay of large picture windows with area for a nice window seat. The spacious LR and DR are open concept, fresh and contemporary, with plenty of room for oversized furniture and formal dining. The kitchen has maple cabinets with granite countertops and is adjacent to a nice breakfast nook with sliding glass doors that lead to the backyard oasis with composite deck and pool. There are 2 good sized bedrooms and a full bath on the 1st floor. Upstairs is a spacious primary bedroom with a cozy sitting area. The finished basement has a really nice rec room with built-in bar, warm pine paneling and 1/2 bath. There is also a bonus room perfect for a work-out room or office, plus laundry area and storage. This house is designed for entertaining family and friends. Great location, just walking distance to Portage Park with its Olympic-size outdoor pool, indoor pool, baseball fields, tennis courts and dog park. Conveniently located to the Metra, CTA, 90/94, downtown and O'Hare, local trendy shops and restaurants. Schedule your showing today!

5111 W Dakin Street, Chicago

$715,000

4 Beds ⋅ 3 Baths ⋅ 12093123 MLS ⋅ CLOSED Status

Introducing a Remarkable updated and meticulously well maintained jumbo Brick Bungalow nestled in the heart of Portage Park, boasting a seamless blend of classic charm and modern elegance. This incredible home was expanded to optimize interior living space, featuring 4 bedrooms plus a loft and 3 full baths, offering ample room for comfortable living. Step inside to discover original details such as a large living room adorned with original stained glass windows and an original fireplace surround, lending character to the home. The dining room flows into the modern kitchen featuring all stainless steel appliances including a brand new stove and refrigerator, new LVT flooring, white quartz counters, subway tile backsplash and warm toned cabinets giving Studio McGee vibes. Two spacious bedroom and a luxurious marble full bathroom complete the main level. On the second level, the enormous primary bedroom impresses with cathedral ceilings creating an airy ambiance, while an adjoining marble spa bath invites relaxation with its separate tub, shower, and expansive walk-in closets, providing a luxurious retreat. The second bedroom where you will find hidden pulldown access to a fully finished attic space, perfect for storage, office or even a play fort. The lofted Space/Family Room offers wonderful natural light, high ceilings, and relaxation this space can easily be converted into a third bedroom on this level. Entertain with ease in the fully finished walkout basement, complete with a spacious wet bar, perfect for hosting gatherings and creating lasting memories, LVT flooring, loads of storage and an additional full bath. The mudroom was built with intention creating the perfect storage solutions right out your back door. Outside you will find a sprawling back deck overlooking the lush grassy yard, ideal for outdoor enjoyment and al fresco dining. A convenient newly built 2 1/2 car garage offers ample parking and storage space. Situated on a picturesque tree-lined street, this residence embodies quintessential Chicago living. Walking distance to the renowned 36 acre Portage Park with multiple playgrounds, tennis courts, baseball diamonds, soccer/football fields, an olympic size pool and field house. Plus enjoy a variety of nearby restaurants such as Community, Tatas Tacos, Moonflower, Easy Street, and Ciao Ciao Gelato. Don't miss the opportunity to make this extraordinary property your new home sweet home.

5321 W Dakin Street, Chicago

$616,000

4 Beds ⋅ 2 Baths ⋅ 12089237 MLS ⋅ CLOSED Status

Fabulous American Four Square located on a phenomenal block of single family homes - only 8/10ths of a mile, and a 15 minute walk to the Blue Line and Metra stops on Montrose! The perfect blend of original charm combined with many updates make this home ideal for today's contemporary living. Enter through the practical mudroom and you are greeted by a spectacular oak staircase and a gracious foyer. While this summer you'll appreciate the new Central Air unit, next winter you'll want to gather family and friends around your living room woodburning fireplace (w/ gas starter) flanked by bookcases that retain their original glass doors! The adjacent family room can be utilized more casually - for watching the Bears in the next Super Bowl perhaps? If you are working from home these days, the French doors of the living room lead to a wonderful sun room, which will make your work feel much less like work! Do plan to entertain, or host next Thanksgiving in the formal dining room, which features a beamed ceiling and several original stained glass windows! The updated kitchen has plenty of cabinets and granite counter space, and overlooks a very spacious rear deck - perfect for those BBQs! By the way, the deck overlooks the rear yard and garden, and has been incorporated into a pandemic-constructed Tree House for children - or maybe your inner child! Three spacious bedrooms and a bath are located on the second floor, and the walk-up attic has recently been renovated into an incredibly spacious and bright 4th bedroom, which could also be an ideal work-at-home office - complete with its own mini-split system for heat and air conditioning. The 7'+ tall unfinished basement features a drain tile & sump pump system together with the laundry, abundant storage, and space to work out. There is definite value-add potential there! The two car garage is accessed via the rear alley, and you have a unique side drive in front, which means you always have easily accessible and super convenient parking for family and guests! Beyond this block and its amazing Annual Block Party, you can stroll to the Portage Park itself - featuring ball fields, tennis courts, outdoor pool (site of the 1972 US Olympic Swimming Trials), dog park and a wonderful Farmer's Market in just 3.5 blocks to the west! Furthermore, there are restaurants, coffee shops, and much, much more all along Irving Park Rd. and Milwaukee Ave.! What are you waiting for? Call me today for a showing!

5024 W Berteau Avenue, Chicago

$486,000

3 Beds ⋅ 2 Baths ⋅ 12084972 MLS ⋅ CLOSED Status

Beautiful English Tudor is a vintage lovers dream come true. Rare full 2 story with OG flr pln has been lovingly mntnd + improved upon by second owners. Elegant authentic features include sep formal entrance, stained glass windows, lovely French doors, wall sconces, glass door knobs, gleaming oak flrs t/o, plaster walls, 8.5 ft coved clgs, built in Dr hutches, wainscoting + much more. Granite kit w/brkfst nook. Den can be a brkfst room w/ gas stove fplc + exposed brick overlooking the garden. Brick paver patio. Rear ext covered porch/balcony off 2nd flr is a wonderful rare find. Full bth rm has a nice sized clawfoot tub. Good size closets. Freshly painted. Full open bsmt w/glass block. Oversized 2.5 car garage fully drywalled and insulated w/2nd story offc/storage, skylights + heater with 220 electric. Security screen doors. Newer roof-tear off. Pool can be removed, or liner replaced. Schools, parks, trans, shopping close by. True pride of ownership lives here. This house is SPECIAL! Owner is a licensed Real Estate Broker in Illinois.

5744 W Cullom Avenue, Chicago

$635,000

4 Beds ⋅ 4 Baths ⋅ 12061075 MLS ⋅ CLOSED Status

Experience Chicago style luxury with this stunning Colonial home! This is a true gem ready to be moved into! House is situated on a rare double lot (7,560 sq.ft.). Gorgeous hardwood floors. Luxury kitchen with Brakur custom cabinets, Quartz Ctops, Bosch Apps. Both the Dining & Living room have bay windows allowing an influx of natural light & inviting space. There is an adjoining multi-purpose space that can be used as a bedroom, playroom, library or office. 2nd floor has 3 VERY generous size bdrms with 2 Full baths. Master Suite w/private balcony and walk-in closet. Finished Basement allows for additional living space utilized for various purposes (family room, home theater, playroom, home office, guest suite or gym). *Equipped with Smart Home features*. This home provides a lot of storage & a backyard that has endless opportunities! Portage Park has accessible public transit options, proximity to transit hubs and frequent service making it convenient to navigate the city. Enjoy all the facilities the actual park (Portage Park) has to offer including: Green Space, Playgrounds, Swimming Pool (indoor & outdoor, splash playground for children), Programs for all ages the entire year, Walking & Jogging Paths & sports facilities. Live in an area with a strong sense of community spirit!

5935 W Newport Avenue, Chicago

$485,000

2 Beds ⋅ 2 Baths ⋅ 12027546 MLS ⋅ CLOSED Status

Desirable Portage Park - Classic Chicago Brick Bungalow with Modern & Vintage Charm. Enter this well maintained Home with original Oak Hardwood Floors, Archways, Crown Moldings, 2 Panel Doors with Hardware. Well illuminated large Living Room, Separate Dining Room, Kitchen with plenty of Wood Cabinets, Extra Storage in Center Island with Corian counter tops. Enclosed heated porch/sun room (porch area insulated, siding & roof-2017)perfect for additional Sitting Area, Home Office or Play Area. Lower Level offers additional space for Related Living Arrangement with 2 Additional Large Bedrooms, Living Room, Full Bath and Nice Size Kitchen. Bonus - Separate Laundry Area. Need more space, bring your decorating and design ideas and expand the 2nd Floor Attic Space to a Large Primary Suite or 2 additional Bedrooms. Step outside to relax and enjoy your morning coffee or BBQ in the yard with beautiful flower garden and privacy fence. 2 Car Brick Garage. Garage Roof, Tuckpointing, Cement around house, Sump Pump & Water Heater -2017. A block away from Portage Park-Chicago Park District which offers 6 tennis courts, 5 baseball fields, soccer fields, in-line skating, Dog Friendly Area, a bike path, a nature walk, 2 fieldhouses offering all kinds of summer activities plus Olympic-size swimming pool. Minutes from Restaurants, Schools, CTA Public Transportation, O'Hare Airport. This is a must see and truly well loved home. Come view and make this beauty your own.

5514 W Dakin Street, Chicago

$523,000

3 Beds ⋅ 3 Baths ⋅ 11999553 MLS ⋅ CLOSED Status

WOW!!! COME CHECK OUT THIS BEAUTIFULLY REHABBED BRICK BUNGALOW LOCATED IN HOT PORTAGE PARK!!! HAS TOTAL OF 5 BRS, A DEN AND 3 BATHS!!! YOU'LL WALK THRU THE MAIN LEVEL THAT HAS A NICE SIZED LIVING ROOM WITH RECESSED LIGHTING LEADING INTO A NICE SIZED FORMAL DINING ROOM. THEN A GORGEOUS KITCHEN WITH GRANITE COUNTERTOPS AND SS APPLIANCES LEADING INTO A BREAKFAST NOOK IN THE BACK. TWO BRS AND A DEN COMPLETE THE 1ST FLOOR. THIS HOME HAS BEAUTIFUL HARDWOOD FLOORS COMBINED WITH SOME WOOD LAMINATE AND VINYL FLOORING THROUGHOUT AS WELL! TO EXPERIENCE THE UPSTAIRS, YOU'LL USE A BEAUTIFUL STAIRCASE WITH WROUGHT IRON SPINDLES THAT INVITES YOU TO THE PRIMARY BEDROOM WITH A LARGE SITTING AREA AND A MASTER BATH! A FULL FINISHED BASEMENT HAS A LARGE FAMILY ROOM, A DECENT SIZED REC RM, THE 4TH AND 5TH BRS. GAS FORCED AIR HEAT/CA UNIT. HAS A NEW COMPLETE TEAR-OFF ROOF ON THE HOUSE AND GARAGE. WALK TO PORTAGE PARK TO ENJOY A PUBLIC SWIMMING POOL, TENNIS COURTS, BASEBALL FIELDS, FOOTBALL FIELD AND PLENTY OF GREENERY! YOUR NEXT NEW HOME IS VACANT AND READY FOR YOUR VISIT! HURRY!!!

4245 N Mason Avenue, Chicago

$619,900

3 Beds ⋅ 3 Baths ⋅ 11965793 MLS ⋅ CLOSED Status

Indulge in the allure of this stunning 4-bedroom, 3-bath bungalow nestled on a serene tree-lined street in Portage Park. A mere three blocks from the park, accessible without navigating busy streets, this residence offers the perfect blend of tranquility and convenience. The main level welcomes you with hardwood floors and elegant wainscoting throughout. A spacious living room, adorned with large picture windows featuring custom curtains, seamlessly flows into a dining room with ample space for a full dining set. Two bedrooms, adorned with room-darkening curtains, and a full bath with a soaking tub complete this level, along with a back porch/mudroom. The chef's kitchen is a culinary haven, boasting granite countertops, a mosaic backsplash, custom cabinets, new light fixtures, and stainless steel appliances. Ascend to the top floor, where the primary suite awaits with an expansive bedroom space, room-darkening curtains, abundant storage, and a full bath, accompanied by extra storage space. The lower level adds versatility with a finished recreation space, an additional bedroom, a storage closet, and a separate laundry room. Step outside to the manicured yard, surrounded by a privacy fence, featuring a new concrete patio that leads to a 2.5-car garage with drywall and epoxy floors. Updates abound, including a new furnace in 2021, a side-by-side washer and dryer, gutters with leaf prevention, ensuring both comfort and efficiency. Located blocks away from retail, dining, buses, the Blue Line, and the iconic Portage Park with its Field house, walking/biking trails, Olympic-sized pool, wading pool, baseball fields, tennis courts, and a dog park. Completely rehabbed in 2015, this residence epitomizes stylish urban living with every amenity at your doorstep.

5347 W Cullom Avenue, Chicago

$415,000

3 Beds ⋅ 3 Baths ⋅ 11848004 MLS ⋅ CLOSED Status

Located in the highly sought after Taft School district, this 3+ bedroom, updated house sits on a hard to find oversized Chicago lot. Check out the low taxes and cost saving Solar Panels on the house. Step up to your sitting porch and in to the open layout of your first floor, which features new hardwood floors in the spacious living area, formal dining room, updated bathroom, and modernized kitchen. The kitchen offers both a breakfast nook and an island for prep. Updates include counter tops, cabinets, and appliances. Upstairs there are three bedrooms, a full bathroom, and lots of closets and storage space. The basement has been used as a bedroom with another full bathroom and a recreation/tv/homework/play area. In the utility area there is a new electrical box, tankless water heater, and washer and dryer. Outside you will notice your privacy and space between the neighbors because of the oversized lot. Even with a full sized pool with custom deck and 2 car garage, this fully fenced yard has room for a patio for grilling and chilling, an oversized 2+ car garage, as well as an area to play. This prime Chicago location is near Smyser Elementary School and Wright College, the historic Patio Theatre, and Portgage Park with its Chicago Parks and Recreation programs. Conveniently located by the Kennedy Expressway, CTA Jefferson Park station, and the shops and restaurants of the Harlem and Irving Plaza like Target, Kohls, Hobby Lobby, Starbucks and Panera. Don't delay, call today!

4148 N Moody Avenue, Chicago

$368,000

10 Beds ⋅ 5 Baths ⋅ 11841037 MLS ⋅ CLOSED Status

CASH ONLY !!!!!!! 2 FLAT with a finished basement + 2 FLOORS COACH HOUSE in the back of the lot! The coach house has minor city violations (Interior stair is too narrow and all the fixtures need to be reconnected back). This is it !Welcome to the ultimate opportunity to own a unique property located in the heart of Chicago's most sought-after area. So many updates on main building and the Coach house for the last couple years (electric, plumbing and much more) All the work was done with city permits and plans.Step inside the front building's first floor to discover an enchanting space featuring three capacious bedrooms +one office, a sleek bathroom, and a bright kitchen with a generous supply of natural light that will make you want to cook and entertain all day long. The second floor is currently rented for $800 month to month and presents two spacious bedrooms with the potential to expand to a third bedroom, providing endless possibilities for customization. Need extra space for family, friends, or additional rental income? Look no further than the fully finished basement with two more bedrooms and one more bathroom, offering ample living space to accommodate your needs. But wait, there's more! The legal coach house, situated at the back of the lot, is a unique feature that adds an additional two floors of living space. With a cozy lower level that features one bedroom and one New bathroom and an upper level with two small bedrooms, a kitchen, and another brand New bathroom, this is the perfect spot to host guests, Airbnb, create a private office space, or generate extra rental income. Location is everything, and this property has it all! Enjoy being surrounded by new construction and the new 6 corners new developments, famous Portage Park with Swimming Pool, soccer and baseball fields - all within walking distance. Don't miss this fantastic opportunity to own a 3-unit property in one of Chicago's most vibrant communities, perfect for investors or owner-occupants looking to make the most of rental income. Take advantage of this chance to own an exceptional property that will give you the flexibility to enjoy life to the fullest!

4954 W Byron Street, Chicago

Start Your Search

The data relating to real estate for sale on this website comes in part from the Broker Reciprocity program of Midwest Real Estate Data LLC. Real Estate listings held by brokerage firms other than our company are marked with the MRED Broker Reciprocity logo or the Broker Reciprocity thumbnail logo (the MRED logo) and detailed information about them includes the names of the listing brokers. Some properties which appear for sale on this website may subsequently have sold and may no longer be available. The accuracy of all information, regardless of source, including but not limited to square footages and lot sizes, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Copyright 2026 MRED LLC. All rights reserved.

Based on information submitted to the MLS Grid as of . All data is obtained from various sources and has not been, and will not be, verified by broker or MLS Grid. MRED supplied Open House information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the DMCA) provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to DMCAnotice@theMLSGRID.com.

The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner’s behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.

Some listings have been excluded from this website.

Portage Park, Chicago IL · Curated MLS Search

Homes with Pool House in Portage Park, Chicago IL

An editorially curated view of every active homes with pool house listing in Portage Park, Chicago IL. Updated in real time from the local MLS, presented without the noise.

Browse Active Listings

Portage Park, Chicago IL Market Snapshot

Inventory here shifts week to week. The listings on this page pull straight from the MLS, so what you see is what's actually for sale right now.

Next Steps in Portage Park, Chicago IL

Speak with an Agent

Call (312) 788-7079

Local Portage Park, Chicago IL expertise

Data Brief

Full Portage Park, Chicago IL Market Report

Pricing trends & absorption

Browse Everything

All Portage Park, Chicago IL Listings

Every active property

← Back to Portage Park, Chicago IL Homes for Sale