Chi - Kenwood Homes under $500,000

Welcome to the vibrant neighborhood of Chi-Kenwood, nestled in the heart of Chicago, Illinois. This charming area is a hidden gem in Cook County, offering a perfect blend of historic architecture, lush green spaces, and a rich cultural tapestry. Known for its friendly atmosphere and community spirit, Chi-Kenwood is an ideal place for families, young professionals, and anyone looking to immerse themselves in the local culture.

One of the standout features of Chi-Kenwood is its diverse housing market. Here, you can find beautiful homes under $500,000, making it an attractive option for first-time buyers and those seeking affordable living in a bustling city. The neighborhood showcases an array of architectural styles, from classic Chicago bungalows to modern townhomes, ensuring there’s something to suit every taste and lifestyle.

Residents enjoy easy access to an array of amenities, including local parks, shops, and restaurants that reflect the neighborhood's rich heritage. The nearby Washington Park and Jackson Park provide ample opportunities for outdoor activities, picnics, and leisurely strolls, making it easy to enjoy the beauty of nature right at your doorstep.

Additionally, Chi-Kenwood boasts excellent public transportation options, connecting you to the rest of Chicago with ease. With its welcoming community, affordable housing, and convenient location, Chi-Kenwood is not just a place to live—it's a place to thrive. Discover your dream home in this captivating neighborhood today!

Newest Chi - Kenwood Homes under $500,000

1140 E Hyde Park Boulevard Unit #3D, Chicago

$439,900

4 Beds ⋅ 2 Baths ⋅ 12774491 MLS ⋅ NEW Status

Beautifully updated 4-bedroom home in the heart of Hyde Park featuring timeless hardwood floors, soaring ceilings, and an impressive vaulted foyer upon entry. The home has a dramatic 36 ft gallery hallway creating an elegant flow to spacious bedrooms. Sun-filled south-facing exposure pours natural light throughout the home, charming sunrooms at both the front and rear of the property offering the perfect spaces to relax, work, or entertain. Thoughtfully updated while maintaining character and warmth, this home combines classic architecture details and modern comfort in one of Hyde Park's most desirable areas. Enjoy easy access to local coffee shops, restaurants, whole foods, and neighborhood favorites along 53rd Street. Convenient transportation options include Metra, CTA, and easy access to Lake Shore Drive. Garage Parking and large storage space included. This home will not disappoint!

1140 E Hyde Park Boulevard Unit #3D, Chicago

$385,000

3 Beds ⋅ 2 Baths ⋅ 12774294 MLS ⋅ NEW Status

Over 2,000 SQ FT | KENWOOD LEGACY ASSET | Experience the power of scale and heritage in this sprawling 2,000 sq. ft. second-floor condo, perfectly positioned in Chicago's Kenwood neighborhood. This is more than a home. Boasting soaring 12-foot ceilings and intricate architectural details, this 3-bedroom, 2-bath offers the volume and character that modern construction cannot replicate. The expansive floor plan features a grand foyer, a living room anchored by a classic fireplace, and custom-built bookshelves by Arthur Levin. The primary bedroom features a unique vanity transition and shutter-door privacy. With an entertainer's floor plan, you will enjoy a grand foyer, massive formal dining room with bay windows and a large private rear porch overlooking the backyard. In-unit laundry included. Steps from the lakefront and elite dining like Virtue and 14 Parish. Seize this rare opportunity for wealth arbitrage in Chicago's most culturally significant corridor. Position yourself in the heart of Kenwood, schedule your private tour today. Monthly HOA includes:Heat, Water, Common Insurance, Security, Lawn Care, Scavenger, Snow Removal

1354 E 48Th Street Unit #2E, Chicago

4453 S Lake Park Avenue Unit #6, Chicago

$435,000

3 Beds ⋅ 3 Baths ⋅ 12773974 MLS ⋅ NEW Status

8-unit building located in the highly sought-after Kenwood neighborhood. This beautifully designed 3-bedroom, 2.5-bath residence offers the perfect combination of modern finishes, spacious living, and an incredible location. Step inside to an impressive open-concept living space highlighted by floor-to-ceiling windows that fill the home with natural light. Gorgeous hardwood flooring flows throughout, complemented by custom cabinetry, contemporary finishes, and a full suite of high-end stainless steel appliances.

4453 S Lake Park Avenue Unit #6, Chicago

$325,000

3 Beds ⋅ 2 Baths ⋅ 12771807 MLS ⋅ ACTIVE Status

4710 S Ellis Avenue Unit #3N, Chicago

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

5000 S East End Avenue Unit #15C, Chicago

$439,900

3 Beds ⋅ 3 Baths ⋅ 12761034 MLS ⋅ ACTIVE Status

Perched high above Hyde Park on the 15th floor of one of the neighborhood's most distinguished vintage buildings, this exceptional residence offers sweeping panoramic views of Lake Michigan. Originally configured as a four-bedroom, the approximately 2,200-square-foot home has been thoughtfully reconfigured to create an elegant and highly functional three-bedroom, two-and-one-half-bath residence with 9.5-foot ceilings, gracious proportions, and abundant natural light. Substantially renovated in 2014, the home beautifully balances the craftsmanship of the 1920s with sophisticated contemporary design. Original plaster moldings were carefully preserved and restored, while dark-stained wood floors and sophisticated lighting bring refinement throughout. The spacious foyer leads to expansive entertaining rooms, with the formal living and dining rooms oriented toward spectacular lake views. The generously proportioned eat-in kitchen is designed for both everyday living and entertaining, with custom cabinetry, new quartz countertops, cabinetry panel high-end appliances, and excellent storage. The dining room opens naturally to both the kitchen and living room, creating an ideal setting for intimate dinners or larger gatherings. Wake up to lake views in the spacious primary bedroom, which offers generous storage and a fully updated bath with dual sinks and a large walk-in shower. A third bedroom is currently configured as a comfortable family room/den and could easily serve as a bedroom, home office, or library. Generous closets throughout include custom California-style storage and a cedar coat closet. In-unit laundry, air conditioning, and humidification provide modern comfort in every season. The meticulously maintained building is renowned for its attentive service and gracious common spaces, including 24-hour door staff, on-site management, secure gated parking, an exercise room, private resident garden with dining areas and gas grills, and generous individual storage. Each elevator serves only two residences per floor, providing an unusual degree of privacy. The building is fully accessible and has been carefully maintained, with substantial improvements to the sidewalks, landscaping, entrance, and other common areas. Located just steps from the lakefront, parks, and beaches and within easy reach of the University of Chicago, the new Obama Presidential Center, and the restaurants, shops, and neighborhood amenities of Hyde Park, this is a rare opportunity to enjoy the scale and elegance of a grand vintage residence-beautifully updated and move-in ready-with the comfort and service of a full-service building.

5000 S East End Avenue Unit #15C, Chicago

5036 S Drexel Boulevard Unit #3N, Chicago

$499,000

4 Beds ⋅ 3 Baths ⋅ 12757973 MLS ⋅ ACTIVE Status

Set along the historic Hyde Park/Kenwood Boulevard, this top floor condo offers the space of a single-family home. With 2,600 square feet, four bedrooms, separate dining room and two outdoor private living areas this is a home offering inviting places to entertain, unwind or simply settle in. The spacious living and family rooms offer comfortable places to gather around original fireplaces, while the dining room with its coffered ceiling, original built-ins and park views create the ideal space for weeknight dinners to long evenings with friends. Throughout the home, pocket doors, original hardware and beautifully preserved architectural details tell the story of its past while providing comfortable modern living. The updated kitchen brings a fresh layer to the home with Bosch appliances, granite countertops, marble tile, and a custom movable island. A butler's pantry and beverage center add extra function and storage, while French doors open to the private rear deck. At the front of the home, a second private terrace overlooking Drexel Boulevard creates a quiet spot to start or end the day. Four spacious bedrooms provide flexibility for family, guests or a home office, complemented by updated baths, in-unit laundry and generous storage. Just minutes away from Hyde Park shops and restaurants, The University of Chicago campus including the upcoming Cancer Pavilion, the Obama Library, the lakefront and public transportation, this is a home with history, space and character, ready for its next chapter.

5036 S Drexel Boulevard Unit #3N, 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

$479,000

2 Beds ⋅ 4 Baths ⋅ 12734285 MLS ⋅ ACTIVE Status

Opportunity knocks! Incredible find in the Historic Kenwood/Hyde Park area. Spacious three level corner townhome with hard wood floors on the first level, high ceilings throughout, fireplace, remodeled kitchen with quartz countertops and stainless-steel appliances and every level has a bathroom. The upper level has skylights and vaulted ceiling which makes the rooms light and airy. Located near the lake, shopping, restaurants and public transportation. Priced right "as is". No HOA fees!

4611 S Lake Park Avenue, 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

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