299 Homes with Tennis Court(s) Community Features

Our website features the best real estate search for homes, condos, land and foreclosure properties available in 299 and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes.

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire.

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood!

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Newest 299 Homes with Tennis Court(s) Community Features

$449,900

4 Beds ⋅ 3 Baths ⋅ 12794711 MLS ⋅ NEW Status

Spacious 6-Bedroom, 3-bath Home in a Prime Belmont Cragin Location! Welcome to this spacious two-story frame home offering an abundance of living space, versatile room arrangements, and an unbeatable Northwest Side location! The first floor features an open-concept living and dining room, three bedrooms, an updated kitchen, and a full bathroom. The second floor offers one additional bedroom, a comfortable family room, and another full bathroom. The finished basement provides even more living space, with two additional bedrooms, a family area, and a large laundry room-ideal for accommodating extended family, guests, or creating a home office or recreation space. Quality updates include complete gut rehabs of the first floor and basement in 2012, featuring updated electrical, plumbing, kitchens, bathrooms, and flooring. The roof, olive-colored siding, and window capping were completed in 2014. Location is everything, and this home delivers! Just one block from the Galewood Metra station, with a CTA bus stop right at your front door. Enjoy being only two blocks south of Riis Park and close to the Brickyard and Bricktown shopping centers. Plus, O'Hare International Airport is approximately 20 minutes away, making commuting and travel convenient. A spacious home, extensive living options, and a fantastic location all in one! Don't miss this opportunity to make this Belmont Cragin property your next home.

2106 N Narragansett Avenue, Chicago

$449,000

4 Beds ⋅ 2 Baths ⋅ 12789830 MLS ⋅ NEW Status

FIRST TIME ON THE MARKET IN OVER 70 YEARS! This beautifully maintained brick bungalow offers timeless charm, exceptional curb appeal, and an incredible opportunity on a lovely tree-lined street in the heart of Jefferson Park! Lovingly cared for by the same family for decades, this home features original woodwork, hardwood floors, and generously sized living spaces throughout. A classic entryway welcomes you into a bright and spacious living room featuring a gas fireplace and an abundance of natural light. The separate formal dining room is perfect for entertaining and leads to a spacious kitchen that opens to a comfortable family room, creating an inviting space for everyday living. The main level also features two generously sized bedrooms and a full bathroom complete with a shower and body sprays and main level laundry. Upstairs, you'll find two additional bedrooms and an abundance of storage space along w/ a bonus sitting room. The expansive unfinished full basement is home to the mechanicals and plenty of additional space with endless possibilities. Outside, enjoy a private backyard with a deck and a detached 2-car garage. Meticulously maintained over the years, this home presents a fantastic opportunity to make cosmetic updates while preserving its original character and building equity. Ideally located near shopping, restaurants, nightlife, parks, public transportation, the Blue Line, Metra, and easy access to I-90/94. A rare opportunity to own a classic Chicago bungalow in one of the Northwest Side's most convenient neighborhoods. Bring your ideas and make this special home your own!

5001 W Wilson Avenue, Chicago

$884,900

4 Beds ⋅ 4 Baths ⋅ 12791054 MLS ⋅ ACTIVE Status

Imagine coming home to a place where luxury feels effortless, every room invites you to stay a little longer, and there's always space to make beautiful memories. Welcome to an extraordinary newer construction home in the heart of Bronzeville, where sophisticated design, exceptional craftsmanship, and everyday comfort come together beautifully. Set on an expansive 25 x 162.5 lot, this stunning 4-bedroom, 3.1-bath home offers two spacious stories, a finished lower level, and an exceptional outdoor retreat. From the moment you enter, soaring 10-foot ceilings, dramatic oversized windows, and impressive 8-foot interior doors create a sense of grandeur rarely experienced in everyday living. Sunlight pours into beautifully appointed spaces, illuminating rich hardwood floors, custom cabinetry, exquisite millwork, designer tile, and elegant Calacatta quartz finishes. Every detail feels intentional, every finish thoughtfully selected. Picture slow Sunday mornings enjoying coffee at your spectacular waterfall kitchen island, preparing your favorite meals in the chef-inspired kitchen, or hosting lively dinner parties that effortlessly flow from the elegant dining room into the inviting family room. As the evening winds down, curl up beside the warmth of the gas fireplace and enjoy the simple pleasure of being home. And then there are the closets! Beautifully designed custom closets transform everyday organization into a luxurious experience. Imagine opening the doors to thoughtfully arranged spaces where your favorite shoes, handbags, and wardrobe have their own special place. Getting dressed becomes something to look forward to, with storage that feels more like a beautifully curated boutique than an ordinary closet. It's the kind of thoughtful luxury that makes everyday living feel extraordinary. Step outside and discover your own private backyard sanctuary! The exceptionally deep lot offers an incredible extension of your living space, complete with a patio and gazebo. Imagine summer evenings entertaining beneath the gazebo, weekend barbecues, intimate outdoor dinners, or simply enjoying a peaceful morning surrounded by the comforts of your own retreat. There's room to entertain, unwind, and create lasting memories throughout the seasons. The beautifully finished lower level offers even more possibilities. Envision a fabulous movie lounge, fitness studio, recreation room, or welcoming guest retreat. A second laundry setup in the basement adds exceptional convenience, making this home as functional as it is beautiful. Situated in historic Bronzeville, one of Chicago's most architecturally significant and culturally celebrated neighborhoods, this residence offers an exceptional lifestyle surrounded by the energy, character, and charm of a thriving community. Some homes are simply places to live. Others become the backdrop for everything that makes life beautiful. From celebrations with the people you love to the quiet moments you'll treasure, this is a home designed for living exceptionally well. Your next chapter begins here. Welcome home!

4542 S Prairie Avenue, Chicago

$1,550,000

6 Beds ⋅ 3 Baths ⋅ 12788493 MLS ⋅ ACTIVE Status

Lincoln Park- This turnkey, legal 3-unit building sits on a quiet tree-lined street in one of Chicago's most desirable neighborhoods. Just 4 blocks from the Diversey Brown Line and only a short walk to the lakefront with easy access to Lake Shore Drive as well, this building has never had a vacancy as the location simply can't be beaten! This property sits in one of Chicago's designated Additional Dwelling Unit Zones and has highly favorable RT-4 zoning and an exceptionally deep 162 ft lot. As such, building an additional dwelling unit/coach house is possible, as is future new development for condos or single-family home. Due to the large lot size, there is a very big back yard and 4-car parking pad with room to increase the number of parking spaces for additional income if so desired. Current rents are generating $111,600 per year but could be higher without any improvements as they are below market value. All three apartments have their own separate gas forced air heating and cooling systems with central air conditioning and all have updated kitchens with dishwashers, granite counters and 42' cabinetry. The top two apartments have spacious private back decks and the first-floor apartment has its own front patio. Tenants pay their own electric and gas bills keeping owner expenses low. Don't miss out on this exceptional investment opportunity in one of Chicago's most sought-after neighborhoods.

740 W Schubert Avenue, Chicago

$399,900

5 Beds ⋅ 3 Baths ⋅ 12789056 MLS ⋅ ACTIVE Status

Classic jumbo red brick bungalow offering 5 bedrooms, 2.5 baths, and a full second-story addition, pairing distinctive architectural character with generous space across three levels. Intricate ceiling trim gives the living and dining rooms a memorable focal point, while first-floor hardwood floors, freshly sanded and stained in light walnut, complement the home's classic appeal. The living and dining areas offer space for everyday gatherings and entertaining. In the kitchen, new stainless steel appliances include a French-door refrigerator. Updated bathrooms feature modern black fixtures. With five bedrooms, the home offers flexibility to arrange sleeping and work spaces to suit your needs. A full, partially finished basement extends the usable space, with two additional rooms for storage or potential office use. A new rear staircase serves both back doors. Set on a 35-foot-wide lot, the property includes a detached 2.5-car garage with a party door, plus a parking pad, providing three total parking spaces in the backyard. Across the street, 18.7-acre La Follette Park adds a wide range of recreation options close to home. Enjoy an indoor pool, fitness center, tennis and basketball courts, an artificial-turf athletic field for football or soccer, playgrounds, and a water play area. From its detailed ceilings and refinished floors to its expanded layout and convenient parking, this bungalow brings together character, practical updates, and room to make the space your own.

5053 W Potomac Avenue, Chicago

$419,900

4 Beds ⋅ 2 Baths ⋅ 12787643 MLS ⋅ ACTIVE Status

Great deal in Albany Park on an extra-wide 36-foot lot, this four-bedroom, two-bath single-family home is fully cleared and ready for its next owner. A welcoming front porch leads to a gracious foyer with a carved staircase. The upper level features two generously sized bedrooms, a kitchen, and a full bath. On the main level, you'll find a spacious living room, formal dining room, well-appointed kitchen with pantry, two additional bedrooms, and a second full bath. Both levels offer a sundeck and exterior access. The unfinished basement includes a washer and dryer, while the expansive yard and two-car garage add to the home's appeal. Located in a City of Chicago Additional Dwelling Area, the property is eligible for additional dwelling unit permits.

4541 N Harding Avenue, Chicago

$654,900

8 Beds ⋅ 3 Baths ⋅ 12787329 MLS ⋅ ACTIVE Status

NORWOOD PARK oversized legal nonconforming 2 flat with newer related living in the lowest level with an "outstanding" curb appeal! You will be proud to come home! All Rooms in all units are good size. Approximately 3000sf of living space. This "tight" building has a $241/monthly Peoples Gas bill. Tear off roof and replacement gutters and siding done in 2023. 1 year old hot water tank; 1 year old garage door; The 16 year old boiler was overhauled and improved in 2023. Brand new flooring in the kitchen and back bedroom on the main level. 1/2 block to Rosedale Park and nearby highways and mass transit creating easy commutes to Ohare International Airport and downtown Chicago.

5856 N Mobile Avenue, Chicago

$555,000

5 Beds ⋅ 4 Baths ⋅ 12787344 MLS ⋅ ACTIVE Status

Prime Chicago Location. Spectacular 5BR, 3.1BA Brick English style home nestled on a quiet tree-lined street in North Mayfair. Offering three levels of living space with baths on all levels. This home has been lovingly cared for by just one family for the last 80 yrs. This residence offers generously sized bedrooms with 2 bedrooms on the main level and 2 upstairs-along with three full bathrooms. The first-floor features include a living room with wood floors, classic dining room, nice size kitchen with plenty of cabinet space and room for a table. 2 main floor bedrooms plus an additional tandem room perfect for home office or 5th bedroom plus a full bath complete the 1st floor. The recently partially dormered second level features 2 more bedrooms and 2 full baths, including a generous primary suite with ensuite bathroom with ample closets. Modern bathroom fixtures with wall hung toilets offers a sleek design and easy to clean floors. New dedicated GFA Carrier furnace and central air on 2nd floor. Stairwell from 1st to 2nd floor has a separate rear entry. The full basement partially finished with half bath, rec room and laundry room with 2 washer/dryers and utility sink. Ample storage. Outside, enjoy a private fenced backyard and a detached two-car brick garage with an extended covered patio area ideal for relaxing or entertaining. Located just steps from Gompers Park with its pool, playgrounds, sports courts, and scenic trails connecting to LaBagh Woods and Forest Glen Woods. Close to Palmer Elementary, shopping, dining, public transit, and I90/94 expressways. One of Chicago's most desirable neighborhoods. Seller is a licensed real estate broker in IL

5012 N Tripp Avenue, Chicago

$439,900

8 Beds ⋅ 3 Baths ⋅ 12786758 MLS ⋅ ACTIVE 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. The 2nd- and 3rd-floor units offer value-add potential through future updates. 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 (2021); 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

$985,000

5 Beds ⋅ 3 Baths ⋅ 12784896 MLS ⋅ ACTIVE Status

Turn of the Century Victorian Home on DOUBLE LOT, 5 bedroom, 3 bath home beautifully loaded with vintage and gorgeous custom features. Sunny large living room, separate parlor/rumpus/TV room/, formal dining room with custom hand milled hutch and pocket door, an AMAZING KITCHEN with 100% all Custom Hand-Milled Poplar and Birch Wood Cabinetry! Renovated First floor bathroom, 2nd floor with 4 bedrooms, full Renovated bath, Attic floor with 5th bedroom and 3rd bath with huge space. Full unfinished walk out basement with dark room, completely fenced back and side yard with newer 3 car garage, with a 2-4 car driveway for extra parking. The BIG EXPENSIVE STUFF, Complete Kitchen, 2 Complete Baths, Roof, Gutters, Electric, Plumbing, Garage, Siding, Windows, Furnace, A/C, Water Heater, Kitchen Appliances, are all NEW or NEWER. Too Much to try to list here. BE SURE TO READ THE ADDITIONAL INFORMATION WITH TONS OF DETAILS IN THE DROPDOWN BOX. A short walk to Redline or Metra, 2.5 blocks to Lake Michigan, Beach and Parks, a short stroll to restaurants, pubs, and shopping! A FABULOUS Home in Rogers Park! Remember, It's ALWAYS Cooler by the LAKE!

6742 N Glenwood Avenue, Chicago

$349,900

2 Beds ⋅ 1 Baths ⋅ 12782556 MLS ⋅ RE-ACTIVATED Status

5431 N Natoma Avenue, Chicago

$459,000

4 Beds ⋅ 3 Baths ⋅ 12775116 MLS ⋅ PRICE CHANGE Status

Welcome to this Bright Beautifully Renovated ALL brick Cape Cod in the Heart of Mount Greenwood! Offering approximately 2,400 square feet of finished living space, this spacious 5 bedroom, 3 bath home combines classic charm with thoughtful modern updates. Updates include: Concrete Repair Front & Rear Stairs 2026. New Front Railings 2026. Roof 2025. HVAC 2020. Kitchen & ALL Bathrooms 2020. Windows 2020. Basement waterproofing 2020. Step inside to find beautiful hardwood floors, elegant wainscoting and a warm, inviting layout designed for comfortable everyday living and entertaining. The updated kitchen features stainless steel appliances, stylish gray cabinetry, soft-close doors and drawers, custom marble countertops and a farmhouse style sink. The kitchen flows seamlessly into the dining area creating a welcoming space for gatherings. The main level offers two bedrooms and full bathroom. Convenient access to the outdoor living space, including a deck and large fully fenced backyard. A detached two (2) car garage provides excellent parking and additional storage. The second floor offers two big bright bedrooms and full bathroom. The spacious primary suite offers a private retreat with a walk in closet and beautifully appointed bathroom featuring a large shower with built in seating, multiple body sprays, wall jets and a relaxing waterfall feature. The fully finished lower level expands the living space with a fifth bedroom, full bathroom, two recreation areas, laundry room and exterior access. Whether used as a family room, home theater, guest suite, or additional entertainment space, the lower level offers exceptional flexibility. Located in desirable Mount Greenwood where there is a real sense of community. This home is close to parks, schools, shopping, dining and transportation. You'd be within walking distance to the celebrated Mt Greenwood Elementary School and Chicago High School for Agricultural Sciences. This home is ready for you to move in and make memories!

10956 S Saint Louis Avenue, 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.

299 Homes with Tennis Court(s) Community Features

Newest 299 Homes with Tennis Court(s) Community Features

How much is your home worth?

How much is your home worth?