Chi - Kenwood Homes under $300,000

Chi - Kenwood Homes under $300,000

Welcome to the vibrant neighborhood of Chi - Kenwood, a hidden gem nestled in the heart of Chicago, Illinois. Known for its rich history and diverse community, Chi - Kenwood is a wonderful place to call home, offering an eclectic mix of culture, convenience, and charm.

As you stroll through the tree-lined streets, you'll discover a delightful blend of architectural styles, from classic brick bungalows to modern townhouses. The neighborhood is not only aesthetically pleasing but also boasts a strong sense of community. Residents enjoy the benefits of local parks, such as the scenic Washington Park, perfect for weekend picnics or leisurely walks.

One of the most appealing aspects of Chi - Kenwood is the affordability of its real estate market. With homes available for under $300,000, this area presents an excellent opportunity for first-time buyers, young professionals, and families looking to settle in a dynamic urban environment. You can find cozy two and three-bedroom homes that provide ample space for comfortable living, all while remaining within reach of the city’s amenities.

Chi - Kenwood is well-connected to public transportation, making commuting a breeze. With easy access to downtown Chicago, residents can enjoy the bustling city life while retreating to the tranquility of their neighborhood. Additionally, the area is home to a variety of local shops, restaurants, and cultural institutions, ensuring there's always something to explore.

Whether you're looking for a starter home or a cozy retreat, Chi - Kenwood offers an inviting community with a wealth of opportunities. Come and discover the charm of this remarkable neighborhood!

Newest Chi - Kenwood Homes under $300,000

4850 S Lake Park Avenue Unit #308B, Chicago
$47,500
2 Beds ⋅ 1 Baths ⋅ 12770645 MLS ⋅ ACTIVE Status
Beautifully updated and move in ready 2 bed, 1 bath co-op in sought-after Hyde Park has custom closets throughout. North-facing unit offers peaceful tree-top views over the courtyard. Unbeatable location just steps to the University of Chicago, Lakefront Trail, Whole Foods, Trader Joe's, Metra Electric Line, CTA buses, and Michelin-starred restaurants. Cash transactions only; rentals not permitted. In addition to the purchase price, a $5,620 transfer shares deposit to Harper Square Cooperativ is required.

4850 S Lake Park Avenue Unit #308B, Chicago
4939 S Dorchester Avenue Unit #5F, Chicago
$147,000
1 Beds ⋅ 1 Baths ⋅ 12767252 MLS ⋅ ACTIVE Status
Updated one bedroom condo in an investor-friendly building across the street from the green oasis of Kenwood Community Park. This top floor condo features hardwood floors, combined living/dining space, spacious bedroom, and updated kitchen with stainless steel appliances and granite counters. The low monthly assessment of $301 includes heat and cooking gas. Access to the CTA #6 bus, University of Chicago UGo shuttle and #172 bus, and Metra Electric train station is within a short walking distance. Dog-friendly Kenwood Community Park, spanning 7 expansive acres, features tennis courts, baseball fields and athletic field for soccer or football. There is a wait list for onsite parking and ample street parking along Dorchester Ave.

4939 S Dorchester Avenue Unit #5F, Chicago
4537 S Drexel Boulevard Unit #203, Chicago
$185,000
1 Beds ⋅ 1 Baths ⋅ 12760987 MLS ⋅ ACTIVE Status
Investor Special!!! Turnkey income-producing opportunity in the highly sought-after historic Drexel Boulevard corridor. This spacious 1-bedroom, 1-bath condominium offers wood-finish flooring throughout, a cozy fireplace, a large bathroom with dual vanities, and an efficient layout that appeals to long-term tenants. The well-maintained building features secure fob entry, an assigned exterior parking space, and low HOA dues. The unit is currently leased to an excellent long-term tenant paying $1,750 per month through March 1, 2027, providing immediate, stable cash flow from day one with no vacancy concerns. Seller is also offering a $2,500 appliance credit, allowing the new owner or future occupant to update the appliances to their personal preference while adding value to the property. A professionally managed, investor-friendly building that allows rentals, making this a rare opportunity to acquire a turnkey asset with immediate income and future upside.

4537 S Drexel Boulevard Unit #203, Chicago
4950 S Chicago Beach Drive Unit #4A, Chicago
$250,000
4 Beds ⋅ 4 Baths ⋅ 12759360 MLS ⋅ ACTIVE Status ⋅ Powhatan BLDG.
Huge (4197 sq. ft.), 4 br/4 bth sun-filled apartment w/ wonderful lake and park views at the Powhatan, an intimate 40-unit 1929 landmark designated Art Deco building overlooking Lake Michigan in Hyde Park. This beautiful apartment features gracious foyer opening to huge living rm ideal for family living and entertaining; large separate dining rm w/ 1920's chandelier sourced for the apartment; 4 ensuite bedrooms including luxurious primary suite w/ custom built-in closets and separate dressing rm; and bright, south-facing office/library w/ built-in bookshelves. Large gourmet kitchen features new maple countertops and painted tile commissioned by second homeowners from MoMA artist Jane Dickerman in the 1950's. The apartment also boasts high ceilings, parquet floors, new light fixtures throughout, washer/dryer, and assigned on-site self or valet parking in secure, gated lot. This full amenity building, famous for its exceptional service, includes 24-hour doorperson; on-site engineer; 24-hour elevator operator who accompanies all guests and residents to their apartments; roof top ballroom w/ piano, terraces and catering kitchen; indoor pool; exercise rm; bike rm; laundry rm and large private storage rm. Assessment includes parking, real estate taxes, and all building amenities and services.

4950 S Chicago Beach Drive Unit #4A, Chicago
4800 S Lake Park Avenue Unit #206, Chicago
$30,000
2 Beds ⋅ 1 Baths ⋅ 12752829 MLS ⋅ ACTIVE Status
Welcome home to an abundance of natural light IN this South facing unit at Harper Square Co-op. Seller is highly motivated and looking for a serious buyer ready to bring their ideas to this 2 bed/1 bath. Perfect blend of comfort, convenience, security, and affordability with access to premium building amenities and city living near downtown Chicago. Perfect location and minutes from Chicago lakefront. University of Chicago and Lake Shore Dr to downtown. Metra, CTA, museum, shopping, restaurants are within walking distance. Co-op assessments include heat, air conditioning, water, cable, taxes, 24 hr. doorperson, huge party room and laundry room. No rentals allowed. Please be aware that the co-op board enforces strict management policies and requires timely, and complete application submissions. CASH DEALS ONLY

4800 S Lake Park Avenue Unit #206, Chicago
4850 S Lake Park Avenue Unit #709, Chicago
$40,000
2 Beds ⋅ 1 Baths ⋅ 12741378 MLS ⋅ ACTIVE Status
A well-maintained residence offering excellent value and strong long-term potential. Located on the 7th floor, this unit provides bright natural light and pleasant open views. The building features a fully renovated marble lobby, 24hour reception, and onsite security, creating a secure and welcoming environment for residents and guests. The home includes 2 bedrooms, 1 bathroom, and a functional combined living/dining/kitchen layout that offers flexibility for updates or customization. Ideal for buyers seeking an affordable entry into the Hyde Park/Kenwood market or investors looking for a value-add opportunity. Close to the lakefront, parks, public transit, and neighborhood amenities. Cash only!

4850 S Lake Park Avenue Unit #709, Chicago
4731 S Ingleside Avenue Unit #A3, Chicago
$229,999
2 Beds ⋅ 2 Baths ⋅ 12755276 MLS ⋅ ACTIVE Status
BEAUTIFUL TOP-FLOOR 2-BEDROOM, 2-BATH CONDO IN KENWOOD! This bright and spacious home features a desirable open-concept living and dining area with soaring ceilings and rich cherry hardwood floors throughout. The primary suite offers a private bath and a generous walk-in closet, creating the perfect retreat. The updated kitchen is equipped with stainless steel appliances, ample cabinetry, and an in-unit washer and dryer for added convenience. Low HOA assessments make this home an exceptional value. Ideally located in the heart of Kenwood, you'll enjoy easy access to the University of Chicago, shopping, restaurants, public transportation, Lake Shore Drive, and the expressway. Just minutes from downtown Chicago, this home offers the perfect combination of comfort, convenience, and location. Don't miss the opportunity to make this exceptional condo your new home!

4731 S Ingleside Avenue Unit #A3, Chicago
4800 S Chicago Beach Drive Unit #1911S, Chicago
$144,900
1 Beds ⋅ 1 Baths ⋅ 12750129 MLS ⋅ ACTIVE Status ⋅ Newport Condominiums BLDG.
Perched on the 19th floor of The Newport Condominiums, Residence 1911S pairs elevated lakefront living with the character and culture that make Hyde Park one of Chicago's most celebrated neighborhoods. This south-facing home is filled with natural light, showcasing sweeping views of Lake Michigan, Lake Shore Drive, and the surrounding neighborhood from nearly every room. The thoughtfully renovated interior features an open-concept kitchen completed in 2018, creating an effortless flow between the kitchen, living, and dining spaces-ideal for entertaining or unwinding against a beautiful lakefront backdrop. Coordinating appliances from the renovation include a sleek integrated dishwasher for a clean, streamlined finish, while the updated bathroom adds to the home's polished appeal. The Newport offers 24-hour door staff and security, on-site convenience store, common-area laundry, rooftop access with panoramic Chicago skyline views, and one assigned storage space. Heat, water, scavenger service, waste management, and extermination are included in the monthly HOA dues. The indoor pool, sauna, and fitness center are available through an optional annual membership for an additional fee. Parking for this residence is leased separately for an additional monthly fee. With no rental cap, this residence also presents an attractive opportunity for investors seeking a property in a desirable lakefront community. Cats are welcome; dogs are not permitted. The current special assessment has been paid in full by the owner for this unit. Just moments from the lakefront trails, beaches, the University of Chicago, the Museum of Science and Industry, neighborhood cafes, local dining, shopping, and convenient transportation downtown, Residence 1911S offers a refined yet connected Hyde Park lifestyle-with some of the city's most captivating views waiting at home. Schedule your private showing today.

4800 S Chicago Beach Drive Unit #1911S, Chicago
4800 S Chicago Beach Drive Unit #308S, Chicago
$119,900
1 Beds ⋅ 1 Baths ⋅ 12731236 MLS ⋅ ACTIVE Status
HUGE PRICE DROP! Perfect for a first time buyer or an investor looking to expand their portfolio! Enjoy lakefront living in this beautifully updated one-bedroom condo at 4800 S. Chicago Beach Drive. Located in a full-service high-rise, this bright and spacious residence features a generous open layout, luxury vinyl flooring, newer kitchen cabinetry and countertops, and stainless steel appliances, including a refrigerator, stove, dishwasher, and microwave.Large windows fill the unit with natural light and offer attractive neighborhood and lake views. The flexible living and dining area provides plenty of space for relaxing, entertaining, or working from home. Residents enjoy a wide range of building amenities, including 24-hour door staff, an indoor swimming pool, fitness center, onsite management, receiving room, laundry facilities, bike storage, and well-maintained common areas. Parking is available for rent. Ideally located near Chicago's lakefront, Jackson Park, the Lakefront Trail, beaches, the University of Chicago, the Museum of Science and Industry, public transportation, shopping, dining, and the Obama Presidential Center. This is an excellent opportunity for an owner-occupant or investor seeking comfort, convenience, and value in the Hyde Park-Kenwood area. Property can be delivered vacant or rented depending on the buyer's request. This Property is priced to sell and will not last! Call or text to schedule a private tour today!

4800 S Chicago Beach Drive Unit #308S, Chicago
5050 S East End Avenue Unit #3B, Chicago
$115,000
2 Beds ⋅ 1 Baths ⋅ 12733343 MLS ⋅ ACTIVE Status
Affordable opportunity to own in a prime Kenwood/Hyde Park location! Skip rising rents and step into a sun-filled, spacious co-op with park views, flexible layout, and easy access to transit, groceries, and the lakefront. Welcome to 5050 S. East End, formally known as The Chippewa - long associated with renowned Chicago architect Mies Van der Rohe. Large windows throughout fill the home with natural light, while newly installed luxury vinyl plank flooring offers a move-in ready feel. Steel kitchen cabinets have mid-century modern vibes creating a space that is both functional and full of personality, further exemplified by parquet wood flooring in the foyer. Oversized bedrooms and a generous combined living/dining area provide flexibility for a variety of living arrangements, whether working from home, entertaining, or creating distinctive spaces. Laundry and additional storage available in the building. Ample street parking and nearby rental options. Residents love the Hyde Park conveniences like Whole Foods, coffee shops, restaurants, community-minded fitness options and transit options for a simple commute. Co-op ownership offers a simplified monthly structure with property taxes, utilities, cable/internet included in the HOA fees. Set in a quiet, walkable, and bikeable neighborhood near the Obama Presidential Center, this is an ideal opportunity to build equity in a well-connected and established community!

5050 S East End Avenue Unit #3B, Chicago
4850 S Lake Park Avenue Unit #903, Chicago
$36,900
1 Beds ⋅ 1 Baths ⋅ 12728372 MLS ⋅ ACTIVE Status
Find yourself at home in an abundance of natural light in this south facing 1 bed 1 bath co-op minutes from everything that sought-after Hyde Park has to offer. Easy access to University of Chicago, Metra, lakefront trail, Museum of Science and Industry, shopping, and award-winning restaurants. Assessments at this fully owner-occupied co-op include heat, AC, water, cable, real estate taxes, 24 hr. door staff, party room, laundry room, fitness center, interior and exterior maintenance. Parking available for additional per month cost. Rentals are not allowed.

4850 S Lake Park Avenue Unit #903, Chicago
5050 S East End Avenue Unit #1E, Chicago
$180,000
3 Beds ⋅ 2 Baths ⋅ 12725289 MLS ⋅ ACTIVE Status
Space, style, and value come together in Hyde Park-Kenwood's most spacious co-op at The Chippewa. This light-filled, first-floor 3BR/2BA co-op is the largest unit in the building, with east-to-west views and a semi-open layout built for gathering. The kitchen delivers custom soft-close cabinetry, white quartz counters, a deep stainless sink, and an LG induction range. Both baths feature white porcelain tile. Enjoy large walk-in closets with California Closets built-ins, custom shades throughout, plus the ease of on-site laundry and additional storage. The flexible third bedroom works as an office, gym, or playroom, perfect for however your life is evolving, in a solid, professionally managed building. The monthly assessment of $2,018 covers property taxes, all utilities, cable, and Wi-Fi, a straightforward, all-inclusive way to budget for homeownership. Location is everything here: exceptionally walkable and bike-friendly, with the Obama Presidential Center, University of Chicago, and 53rd Street's shops, restaurants, and banks all just a quick trip away, buses, trains, and lakefront green space are practically at your doorstep. Sold as is, subject to board approval. Owner is offering four months of paid parking at a designated spot at 5140 Hyde Park Ave. Additional street and rental parking options are also available nearby.

5050 S East End Avenue Unit #1E, 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.