Oakland Real Estate

Oakland: A Hidden Gem in Illinois

Located in the state of Illinois, Oakland is a charming neighborhood that offers a unique blend of suburban tranquility and urban convenience. Situated in the heart of Coles County, Oakland is a small community with a rich history and a tight-knit community.

One of the standout features of Oakland is its natural beauty. The neighborhood is surrounded by picturesque landscapes, including rolling hills, lush forests, and serene lakes. This makes it a haven for outdoor enthusiasts who enjoy activities like hiking, fishing, and boating. The peacefulness of the area also makes it an ideal place for families looking to escape the hustle and bustle of city life.

Despite its small size, Oakland has a range of amenities to offer its residents. The neighborhood boasts excellent schools, including Oakland Community Unit School District, which is known for its high-quality education. There are also several parks, playgrounds, and recreational facilities that provide ample opportunities for leisure and entertainment.

In terms of real estate, Oakland offers a variety of housing options to suit different preferences and budgets. From cozy single-family homes to spacious apartments, there is something for everyone. The neighborhood also has a strong sense of community, with friendly neighbors and a welcoming atmosphere.

If you're looking for a peaceful and close-knit community in Illinois, Oakland is a hidden gem worth considering. Its natural beauty, range of amenities, and strong sense of community make it an ideal place to call home.

Newest Listings in Oakland

$2,150,000

12673900 MLS ⋅ NEW Status

Once in a Generation, The Crown Jewel of Oakland set on a botanical campus spanning 70 feet of frontage. If you seek the best, if you have exquisite taste, if you want a one of a kind with an elevator that opens directly into most apartments with grand terraces, you have arrived. Located in an exclusive community alongside million dollar homes & within 1/4 block of Mandrake Park, 5 minute walk to the lakefront at the very north end of Drexel Blvd, with its idyllic fountain & cul-de-sac is a magical whimsical storybook setting offering 5 Massive full-floor units ultra-luxurious 3-4 Bed/2-3 Bath residences set in a made for TV boutique, elegant, Gothic Greystone. Be inspired by the grand, formal lobby with inlaid stone floors, intricate woodwork, stunning modern art, a crystal cut chandelier & super "mod" LED wall sconces. The elevator opens directly into most residences' private foyer, which leads to a massive great room, with soaring ceilings & 7' tall window bays that capture phenomenal sun soaked south & west vistas up & down lush & forested Drexel Boulevard. Gorgeous plank hardwood floors, which contrast with sleek 7" crown & baseboard moldings, 8' tall solid core doors, polished chrome door handles & accessories, a custom designed & built fireplace with glass, stone & quartz mantel + gorgeous lighting with Decora switches & dimmers. Adjacent to the great room, cook, entertain & eat in a true & REAL gourmet kitchen with 1 1/4" thick quartz countertops, a massive work island with bar stool seating, state-of-the-art stainless appliances, a multi burner stove, tunnel exhaust hood, dishwasher, 36" refrigerator with ice & water dispensers, built-in microwave drawer & brilliant porcelain full height backsplashes. Other features include strategically placed cable & electric for flat screen televisions, Hi Efficiency HVAC, high tech LED lighting & many other features. Gracious jaw dropping primary bedroom suite with an infusion of natural light from tall south facing windows, enormous walk-in closet is ready to house a large wardrobe, with custom double hanging SS organizers some which include 20 lineal feet of hanging & 55 lineal feet of shelves. Resort Luxury spa bathroom with heated porcelain tile heated floors, steam shower, quartz bench, a custom designed floor to ceiling glass wall & door system, a rain shower, handheld shower & separate body washes, 6' air bath, a wall mounted floating double bowl vanity & two large mirrored medicine cabinets. Numerous oversized rear terraces offer respite to enjoy cocktails, read a book or have breakfast through dinner, private & spacious with sweeping downtown views. Full Laundry Center complete with full size washer & dryer, countertops & cabinetry cabinets. Enjoy fully curated exotic botanical gardens fully with specimen trees & bushes, many grafted, from around the world, including Japan, various countries in Eastern Europe, Canada & the USA ( all irrigated controlled by app) topped off with 9 car garage (2 of 9 Tandem). Fully stabilized with exceptional longer term tenants, this stunning, unique, trophy property offers a rare hybrid opportunity pairing investment with legacy. Full financials, floorplans, survey, and extensive pictures available. Actual Annual Income $213,045/NOI $141,525 / 6.5CAP Pre Approved buyers only. 48-72 hours' notice to show M-F (no weekend showings)

3967 S Drexel Boulevard, Chicago

$775,000

4 Beds ⋅ 3 Baths ⋅ 12754216 MLS ⋅ NEW Status

2,800 sq. ft., 4-story, 4 BD/2.1 BA townhome + an attached (heated) 2 car garage. Experience unobstructed views of Lake Michigan and the downtown Chicago skyline. Featuring 2 prominent sun exposures - northern & southern plus a 1st floor patio (18' x 7') & 2nd, 3rd, and 4th floor balconies! Throughout the townhome, there are custom wood railings with tempered glass inserts, hardwood flooring, and recessed lighting. The kitchen features an expansive peninsula with rainfall quartz countertops, a built-in dry bar, high gloss cabinetry, a quartz backsplash, and a stainless steel Bosch appliance package including an external venting range hood. Other exciting home features include: an electric fireplace and media wall adorned with marbled quartz, custom Norman window treatments (including mechanical ones in the living room), CAT-6 wiring, a top floor wet bar, Inspired custom closets, and a spa-like primary bathroom with heated floors and a soaring vaulted ceiling. Easy access to I-90/94, I-55, Mariano's, LA Fitness, Jewel-Osco, Bronzeville Dog Park, Ellis, Madden, & Mandrake Parks, Wintrust Arena, Rate Field, Chinatown Square, Illinois Institute of Technology McCormick Place, Soldier Field, Northerly Island, Oakwood Beach, and Burnham Park Harbor. 1.1 miles from the CTA Green Line Indiana Station. 1.3 miles from the CTA Green Line 43rd Station. 1.4 miles from the CTA Green Line Bronzeville-IIT Station. 1.3 miles from the METRA 47th Street/Kenwood Station. HOA $130/monthly (includes water, sewer, trash removal, common area insurance, and common area maintenance). No special assessments ongoing or upcoming. Roofs are unit owner responsibility (10-year warranty). No rental restrictions - corporate rentals, short-term rentals, or even Airbnb/VRBO are allowed.

3901 S Lake Park Avenue, Chicago

$400,000

3 Beds ⋅ 3 Baths ⋅ 12719539 MLS ⋅ ACTIVE Status

Enjoy comfortable living in this beautifully maintained 2,300-square-foot first-floor condo located in Chicago's desirable Oakland community. This spacious residence features 3 bedrooms, 2.5 bathrooms, elegant hardwood floors, and the convenience of in-unit laundry. relaxing or outdoor dining, and a dedicated storage unit. Ideally situated in the historic Oakland neighborhood, this home offers convenient access to the lakefront, parks, public transportation, downtown Chicago, museums, universities, and neighborhood dining. Don't miss this exceptional opportunity to own a spacious, amenity-filled condo in one of Chicago's most convenient South Side communities.

3733 S Lake Park Avenue Unit #1, Chicago

$799,000

5 Beds ⋅ 3 Baths ⋅ 12680626 MLS ⋅ ACTIVE Status

What you've been waiting for in Bronzeville-an extraordinary residence on picturesque Lake Park Avenue that seamlessly blends timeless vintage character with sophisticated modern updates. Far from a cookie-cutter home, this one-of-a-kind residence offers over 4,000 square feet of thoughtfully designed living space across three levels plus a finished basement, creating a floorplan that is as distinctive as it is functional. From the moment you arrive, the stately red-brick exterior and impressive custom solid-wood double doors make a lasting first impression. Step through the private vestibule foyer and into a home filled with architectural details, warm finishes, and captivating design elements rarely found in today's newer construction. A dramatic staircase anchors the home, while the open-concept main level effortlessly balances grandeur and comfort, making it ideal for both everyday living and entertaining. The inviting living room features, soaring ceilings, a striking stone accent wall and cozy fireplace, creating the perfect gathering space. The expansive kitchen serves as the heart of the home, offering abundant cabinetry, stone countertops, stainless steel appliances, and generous space for dining and hosting family and friends. The second level showcases three spacious bedrooms, a full bath, and a versatile family room-an uncommon and highly desirable layout that provides flexibility for growing households, guests, or work-from-home needs. Occupying much of the third floor, the luxurious primary suite serves as a private retreat. The oversized bedroom is complemented by a spa-inspired bath featuring a custom walk-in shower, distinctive tile flooring, dual vanities, and a relaxing whirlpool tub. An additional bedroom on this level is currently configured as a home office, offering endless possibilities. A skylight illumates the stunning staircase. The finished, walk-out, basement extends the living space even further with another family room, a full bathroom, an oversized laundry room, and a private sauna-your own personal wellness retreat. Outdoor living is equally impressive, featuring a large rear deck, yard space, and garage parking. Perfectly situated on one of Bronzeville's most desirable blocks, this home is within walking distance of neighborhood parks and the pedestrian bridges that connect you to Chicago's stunning lakefront. Rich in character, architectural charm, and modern comfort, this is a rare opportunity to own a truly distinctive home in one of the city's most vibrant and historic neighborhoods. Welcome home!

4126 S Lake Park Avenue, Chicago

$344,900

3 Beds ⋅ 3 Baths ⋅ 12685324 MLS ⋅ ACTIVE Status

Welcome to this marvelous over-sized duplex condo in the picturesque sought after neighborhood of historic Bronzeville. Featuring 3 bedrooms and 3 full bathrooms, this beautifully updated duplex offers an abundance of space that is drenched with natural light. The gleaming luxury hardwood floors welcome you in the spacious living room with a grandiose patio door that offers wonderful views of the beautiful tree lined streets. The living room guides you into the spectacular kitchen with amazing high end cabinets, elegant quartz countertops that boast a breakfast bar and stainless steel appliances. The living room offers a serene setting that features a breathtaking fireplace. The main floor also offers a conveniently located full bathroom and a guest bedroom, perfect for when entertaining family and friends. The lower level features two expansive master bedrooms with new carpet, new light fixtures, large walk-in closets and full master baths. The unit also offers plenty of storage space throughout and in-unit laundry room. Enjoy some fresh air on those spring and summer days on your own private balcony. Updates include: New paint throughout, new light fixtures, refinished hardwood floors, new carpet, new kitchen faucet, and new cabinet pulls. The unit includes 1 parking space conveniently located steps away from the backdoor entrance, intercom system, and a private storage locker. Walking distance to the beautiful Oakwood Beach. The proximity to golfing, parks, shopping and dining is outstanding. Pets are welcome.

4105 S Drexel Boulevard Unit #1SR, Chicago

$21,999

12393102 MLS ⋅ ACTIVE Status

DRIVE BY!

1005 N Lewis Avenue, Waukegan

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.