Near East Side Homes under $500,000

Our website features the best real estate search for homes, condos, land and foreclosure properties available in Near East Side 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 Near East Side Homes under $500,000

201 N Westshore Drive Unit #2804, Chicago

$450,000

2 Beds ⋅ 2 Baths ⋅ 12789647 MLS ⋅ NEW Status

Experience elevated city living in this elegant 2-bedroom, 1.5-bath residence on the 28th floor of The Lancaster, showcasing breathtaking views of Lake Michigan, Harbor, and the surrounding parks. Enjoy stunning sunrises from your spacious east-facing balcony and an inviting open-concept living space featuring hardwood floors, rich cherry Brookhaven cabinetry, granite countertops, stainless steel appliances, and in-unit laundry. The Lancaster offers exceptional amenities, including a spectacular 30th-floor rooftop deck with panoramic skyline and lake views, a state-of-the-art fitness center, resident lounge with a full kitchen, fireplace and workspace, 24-hour door staff, and on-site management. Nestled in the peaceful and highly desirable Lakeshore East neighborhood, just steps from Lakeshore East Park, Millennium Park, Maggie Daley Park, the Lakefront Trail, Chicago Riverwalk, and Michigan Avenue's premier shopping and dining. Storage is included, and deeded garage parking is available for an additional $35,000. An exceptional opportunity to enjoy luxury living, spectacular views, and an unbeatable downtown location!

201 N Westshore Drive Unit #2804, Chicago

400 E Randolph Street Unit #2218, Chicago

$285,000

1 Beds ⋅ 1 Baths ⋅ 12789344 MLS ⋅ NEW Status

BRING YOUR CREATIVE SIDE AND MAKE IT YOUR OWN! This spacious 825 sq. ft. one-bedroom offers a wonderful opportunity to create a home that reflects your personal style. Do as much-or as little-as you want! Enjoy a generous floor plan, huge private terrace, and beautiful views in a fantastic location. The home is priced with its current condition already considered, giving you the flexibility to update, renovate, or simply move in and make changes over time. A great opportunity to add your own finishing touches without paying for someone else's renovation choices. GREAT LOCATION, GREAT BUILDING & GREAT VIEWS! The building offers strong reserves and solid finances, along with an impressive array of amenities. Enjoy a full-service lifestyle with a health club and spa, indoor pool, fitness facilities, sundeck and more. Whether you're looking for a primary residence, in-town home, or a property you can personalize over time, this is an opportunity to get a large one-bedroom with exceptional outdoor space in a highly desirable building and location. Bring your ideas, bring your style, and make this one your own!

400 E Randolph Street Unit #2218, Chicago

400 E Randolph Street Unit #1515, Chicago

$425,000

1 Beds ⋅ 1 Baths ⋅ 12788521 MLS ⋅ ACTIVE Status ⋅ New Eastside BLDG.

Gorgeous world-class LAKE views for life! Great large condo with sunny South views of the lake, harbor, park, and skyline. Large private terrace. Full-sized 1-bedroom with 825 sqft. Financially strong building. Newer windows, new risers, newer health club, new elevators and more! This is a great unit in the heart of Chicago's New Eastside (60601). Come see the exciting "New Eastside" neighborhood. The building, Outer Drive East, is almost new again, with numerous renovations and strong financials. All-new lobby with glistening white terrazzo floors. New windows, new 5-star resort-like health-fitness spa. Racquetball, basketball, free weights, machine weights, cardio, massage therapy, children's playroom, and a famous geodesic domed year-round sunny pool. Hospitality/party room, business center with resident computers and a printer, library, community BBQ grills, and a bi-level sun deck. HOA includes heat, a/c, gas, cable, cable with TiVo 6 DVR, 24/7 lobby desk, security, and door attendants. 3 bike rooms and 3 car-washing stalls. A restaurant bar/grill, a beauty and nail salon, and several other businesses are located on the 7th floor. There are two grocery shopping options: either Bockwinkel's Harbor Market (across the street) or a 2-story Mariano's grocery store with good prices and a wide selection for your daily shopping needs. Very friendly building with lots of social activities and events, including a book club, world affairs club, bingo, summer picnic, children's Halloween party, children's holiday party, and a resident holiday party, to name a few. Great Outer Drive East community in the New Eastside neighborhood. Nestled in the New Eastside neighborhood is Lakeshore East Park. This 6-acre oasis in the neighborhood's nucleus includes large grassy areas, a children's playlot, and a dog park. Maggie Daley Park is across Randolph Street to the south and incorporates tennis courts, a children's activity area, park district facilities with programming, the famous ribbon ice skating rink, mini-golf, and professional outdoor climbing walls. Millennium Park is a block away from all the world-famous music venues, including the Grant Park Orchestra, Saturday morning exercise classes, and outdoor movies in the summer. 30-minute free parking for showings, guests, and deliveries. Located in the New Eastside neighborhood, this prestigious condo is just moments away from fine dining, upscale shopping, the lake and harbor, and cultural landmarks.

400 E Randolph Street Unit #1515, Chicago

400 E Randolph Street Unit #1223, Chicago

$309,900

1 Beds ⋅ 1 Baths ⋅ 12774511 MLS ⋅ ACTIVE Status

An enviable east-facing exposure fills this 1-bedroom, 1-bath residence with natural light, showcasing beautiful lake views from both the living room and bedroom. Step outside onto your private 15-foot balcony with east facing lake views and New Eastside architecture. Space for morning coffee and a dining area. Modern kitchen with granite counters, all stainless steel appliances (2yrs old), gas cooking range, in-sink waste disposal, microwave, dishwasher, kitchen island with bar seating. Enjoy organized living with ample storage in the walk-in closet adjacent to the bathroom. Large light- filled bedroom with full wall of windows that allows for fresh air and space for both king size bedroom suite and office. Full wall closet in bedroom with shelving and depth. The bathroom features a shower and tub combination, along with a ceiling fan with integrated lighting. This prestigious and historic condo is just moments away from fine dining, upscale shopping, the lake and Monroe harbor. Nestled in the New Eastside neighborhood is Lakeshore East Park. This 6-acre oasis in the neighborhood's nucleus includes large grassy areas, a children's playlot, and a dog park.Steps to Millenium Park or Navy Pier, Bockwinkel's Harbor Market , 2-story Marianos, Avli & Wildberry. Parking is all rental at $220/month(indoor heated garage) Very easy to show. Vacant and furniture negotiable. Monthly association fees cover heating & AC, gas, TV & cable, internet. Building amenities include *Iconic Indoor Heated Pool & Whirlpool *Sundeck *Q Spa Plus (facials,skincare,waxing and brows) & Health Club *Sauna *Steam Room *Basket Ball Court *Racquet Ball Court *Ping-pong table *Bike room **24/7 Doorman, security, and onsite maintenance staff** Storage options include an assigned 4x4 locker issued by management upon availability or a public self storage facility on site.

400 E Randolph Street Unit #1223, Chicago

201 N Westshore Drive Unit #2006, Chicago

$382,500

1 Beds ⋅ 1 Baths ⋅ 12774416 MLS ⋅ ACTIVE Status

Bright, beautifully updated one-bedroom with stunning lake, river, harbor, and city views in the heart of Lakeshore East. Floor-to-ceiling windows fill the home with natural light, while a private balcony offers the perfect place to take in the skyline. The residence features hardwood floors, an in-unit washer/dryer, and a sleek chef's kitchen with quartz countertops, brass fixtures, stainless steel appliances, and modern cabinetry. Full-amenity building with 24-hour door staff, state-of-the-art fitness center, resident lounge, rooftop deck, dry cleaner, storage, bike room, and on-site management. Prime Lakeshore East location just steps from the lakefront, Riverwalk, Millennium Park, Maggie Daley Park, Navy Pier, Pedway, Mariano's, restaurants, shops, theaters, museums, and more. Parking is additional 35k

201 N Westshore Drive Unit #2006, Chicago

$349,000

1 Beds ⋅ 1 Baths ⋅ 12774226 MLS ⋅ ACTIVE Status ⋅ Harbor Point BLDG.

10! Totally Upgraded Condo with dramatic 49th floor views of Navy Pier and the Lakefront. Spacious, bright open layout perfect for entertaining. Hardwood bamboo floors, remodeled kitchen with stainless steel appliances, custom marble tile backsplash, lots of cabinetry, granite counters, island with breakfast bar, Grohe faucet and Bosch dishwasher. Master bedroom easily accommodates a King bed. Natural stone bathroom with granite countertop and additional storage. Custom lighting throughout, in-suite laundry/pantry with full size front-loading washer/dryer. Heated rental garage parking, valet available. Full amenity, pet friendly building with 24hr door staff, indoor pool, large fully-equipped fitness room, sauna, steam room, sun deck with grills, owner's lounge and party room, storage locker. On-site Bockwinkles market and dry cleaners. Located in the heart of the New East Side, Chicago's neighborhood enclave close to Millennium Park, Maggie Daley Park, Mariano's, Michigan Ave.

155 N Harbor Drive Unit #4905, Chicago

420 E Waterside Drive Unit #2602, Chicago

$375,000

1 Beds ⋅ 1 Baths ⋅ 12756096 MLS ⋅ ACTIVE Status ⋅ Regatta BLDG.

Best one bedroom floor plan at the Regatta in Lakeshore East with balcony overlooking popular park. Grand foyer, hardwood floors, brand new carpeting, freshly repainted and deep cleaned, in unit washer and dryer. Vast living, dining space with open kitchen concept, seating at the bar, rounded edge 1.25" granite counters, stainless steel KitchenAid appliances Snaidero Cabinetry with cylinder pulls. Bedroom with walk in closet. Bathroom dressed in honed marble, separate shower and soaking tub, Snaidero vanity, medicine chest. Enjoy views of the city lights, views of the Lakeshore East Park, Maggie Daley, Millennium Parks. The Regatta is a full amenity building including 24 hour doorstaff, onsite property manager, building engineer, maintenance staff, indoor pool and whirlpool, state of the art gym, community and game room for casual use and private events. Deeded garage parking @ $35,000.

420 E Waterside Drive Unit #2602, Chicago

360 E Randolph Street Unit #403, Chicago

$415,000

1 Beds ⋅ 2 Baths ⋅ 12765778 MLS ⋅ ACTIVE Status ⋅ Buckingham Residences BLDG.

Move-in ready 1-bedroom, 1.5-bathroom condo at The Buckingham, in Chicago's New East Side next to Lakeshore East. This 1,000-square-foot residence enjoys open, unobstructed views toward Millennium Park, a rare find on a lower floor. Recent updates include a new energy-efficient HVAC system, installed in 2024, and a brand-new refrigerator, just installed, and freshly painted throughout. The open living and dining area connects to a spacious kitchen, and the 1.5-bath layout adds a powder room for guests alongside the primary suite's full private bathroom. In-unit washer and dryer. One heated indoor garage parking space (#P5-241) is included in the price. Amenities include an indoor rooftop pool, rooftop sundeck, fitness center, steam room, on-site dry cleaner, bike room, and a private storage cage (#P1-292). The attached garage provides hand car wash service and valet parking for visitors. Walk to Maggie Daley Park, Millennium Park, Grant Park, and Lakeshore East Park, with Mariano's, CVS, cafes, restaurants, and salons just steps away. The Lakefront Trail, Chicago Riverwalk, Museum Campus, Monroe Harbor, and the Loop theater district are all close by. Commuters can reach Metra Millennium Station, the Pedway, and CTA Loop trains at Washington/Wabash in minutes. The monthly assessment covers heat, air conditioning, water, cable, internet, and full access to all building amenities. The Buckingham is a financially strong, boutique high-rise with approximately $7 million in reserves. Investor friendly: rentals are allowed with a 1-year minimum lease. Park views, a newer heat pump, heated parking, and an all-inclusive assessment, in an exceptionally well-managed building in the heart of the New East Side!

360 E Randolph Street Unit #403, Chicago

360 E Randolph Street Unit #3205, Chicago

$419,000

1 Beds ⋅ 2 Baths ⋅ 12759607 MLS ⋅ ACTIVE Status

Welcome to The Buckingham, perfectly positioned in Lakeshore East - one of downtown Chicago's most unique pockets, where the city feels just outside your door while home still feels tucked away from it all. Perched on the 32nd floor, this spacious 1-bedroom, 1.5-bath residence offers approximately 1,000 square feet with beautiful views overlooking Lakeshore East Park and the surrounding skyline. The thoughtfully updated interior features hardwood floors, an updated kitchen with stainless steel appliances, generous living and dining space, in-unit laundry, ample storage, and a spacious bedroom with room to truly settle in. Heated, deeded garage parking is included in the sales price - an increasingly valuable downtown convenience. The Buckingham offers full-service living with 24-hour door staff, on-site management and engineering, an indoor rooftop pool, fitness center, sauna, sundeck, party room, bike storage and more. What really sets this home apart is the neighborhood. Lakeshore East feels like its own residential oasis surrounded by parks, yet you're moments from everything that makes downtown Chicago so desirable. Mariano's is right around the corner, with additional everyday conveniences throughout the Lakeshore East Village. Walk to Millennium Park, Maggie Daley Park, the Riverwalk, lakefront, Michigan Avenue, restaurants and shopping, with convenient access to Millennium Station, CTA buses and the Loop for an easy commute. A true neighborhood feel in the middle of the city - with the space, views, amenities and included parking to make downtown living easy!

360 E Randolph Street Unit #3205, Chicago

$389,000

1 Beds ⋅ 2 Baths ⋅ 12754520 MLS ⋅ ACTIVE Status ⋅ Harbor Point BLDG.

Experience ultimate high-rise living in the iconic Harbor Point--one of Chicago's first condo buildings. This stunning, light-filled 2-bedroom, 1.1-bathroom unit in coveted Lakeshore East neighborhood! Perched perfectly to capture panoramic East and North exposures, this unit boasts breathtaking, unobstructed views of Lake Michigan, Navy Pier and the iconic city skyline. The open-concept kitchen flows effortlessly into a spacious living and dining area, making it an entertainer's dream-especially during Navy Pier summer fireworks! Storage is never an issue here, with an abundance of oversized closets and dedicated storage space throughout. The thoughtfully designed layout features two separate bathrooms, providing excellent privacy for guests Equipped with hardwood floors throughout, washer/dryer in-unit and spacious primary suite. Located in a premier, full-amenity luxury building with too many to list: residents enjoy 24-hour door staff, a state-of-the-art fitness center, an indoor pool, premium lounge spaces both indoor and outdoor, grocery store, on-site mgmt, racquetball/pickleball courts with valet parking garage for extra monthly cost. All of this is just steps from the award-winning Lakeshore East Park, the Lakefront Trail, Maggie Daley Park, Mariano's, and world-class dining. This is urban luxury at its absolute finest!

155 N Harbor Drive Unit #2007, Chicago

$449,000

1 Beds ⋅ 1 Baths ⋅ 12748443 MLS ⋅ ACTIVE Status

Live above it all in this beautifully upgraded 1-bedroom residence on the 36th floor of the iconic Cirrus Condominiums in Lakeshore East. Floor-to-ceiling windows showcase stunning skyline views and fill the home with natural light, while high-end finishes, smart blinds, a custom walk-in closet, and in-unit laundry create effortless everyday living. The sleek modern kitchen features quartz countertops, contemporary cabinetry, and premium Gaggenau and Bosch appliances. Garage parking is available for an additional $50K, storage is included, and the home can be purchased partially furnished if desired. Cirrus delivers an unparalleled resort-style lifestyle with an extraordinary collection of indoor and outdoor amenities. Enjoy indoor and outdoor pools, a hydrotherapy pool, state-of-the-art fitness center, strength and motion studios, steam rooms, sauna, winter garden conservatory, salon, golf simulator, screening room, music and maker spaces, kids club, work-from-home lounges and meeting rooms, and more. The spectacular 41st-floor amenity level offers breathtaking views of Lake Michigan, DuSable Harbor, and Navy Pier, along with a rooftop terrace, lawn, fire pit, grilling stations, chef's kitchen, private dining space, and wine lounge. Pet-friendly amenities include an indoor dog run, pet spa, and outdoor Bark Park. With direct access to lakefront trails and an unbeatable location moments from the lake, Cascade Park, Maggie Daley Park, Millennium Park, dining, shopping, and everything downtown Chicago has to offer, Cirrus provides the ultimate combination of luxury, convenience, and lifestyle. LEED Gold and Fitwel Certified. Take a 3D Tour-click the 3D button and walk around!

211 N Harbor Drive Unit #3605, Chicago

225 N Columbus Drive Unit #6009, Chicago

$330,000

1 Beds ⋅ 1 Baths ⋅ 12748600 MLS ⋅ ACTIVE Status

Nothing more complete in Lakeshore East than Aqua Tower. Residence 6009 showcases views of Lake Michigan, the Lakeshore East Park, Pritzker Pavilion at Millennium Park, the Chicago Art Institute and the architectural wall of yesteryear down Michigan Avenue. Floor to ceiling windows and large balcony off living area. Easiest access to the Lakeshore East Park, Mariano's and Chicago's Underground Pedway. Aqua is a full service high-rise with 120,000 square feet of amenities space including an indoor lap pool, finest gym, basketball court, cardio room, steam, sauna, movie theatre and game rooms. Outdoor lap pool on sundeck, running track, fire pits, various lounge spaces. 24 hour doorstaff. Residence 6009 features Snaidero kitchen and bathroom cabinetry, KitchenAid stainless steel appliances, granite stone counter tops, Grohe/Moen Toto plumbing fixtures. Two customized closets with built in organizers. In unit washer and dryer. Hardwood floors throughout this home. Garage Parking available for purchase through separate owner in the building. Ask Co-Lister for more information.

225 N Columbus Drive Unit #6009, 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.

Near East Side Homes under $500,000

Newest Near East Side Homes under $500,000

How much is your home worth?

How much is your home worth?