1,741

Oakland Homes

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  • /29

    $499,500 Pending

    • 3 Beds
    • 4 Baths
    • 1,600 Sq Ft

    4134 S Ellis Ave, Chicago, IL 60653

    Newer Construction, 4 Bedroom, 2 Full Bath, 2 Half Bath Single Family Home in the Oakland/Kenwood Neighborhood with close proximity to the Lake, Hyde Park and Bronzeville. The residence is situated on a lovely tree lined, one way street on an oversized city lot with a two car garage and huge backyard. The main floor is open floor plan and features hardwood flooring, a gas fireplace in the living

    Rosa Sanchez-Fryer @properties Christie's International Real Estate

    4134 S Ellis Ave, Chicago, IL 60653
  • /23

    $1,100 - $1,485 per month

    Lake Grove Village

    1-3 Beds

    3555 S Cottage Grove Ave, Chicago, IL 60653

    INCOME RESTRICTION: Individual - $50,400, Two People - $57,600, Three People - $64,800New AppliancesLuxury Vinyl Plank Flooring in Kitchen, Foyer, and BathOutstanding Lake, Skyline, and City ViewsWalking Distance to Grocery, Shopping, and Fitness Nearby (Lake Meadows Shopping Center)Ground Floor Laundry Room with new Laundry Equipment (2021)Steps

    3555 S Cottage Grove Ave, Chicago, IL 60653
  • /2

    $260,000 Sold Jul 11, 2025

    • 1,200 Sq Ft
    • $217/SF
    • 44 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1920

    844 E 40th St Unit A2, Chicago, IL 60653

    Wonderful condo off historic Drexel Blvd. just blocks to the 39th St. beach/DuSable LSD with open floor plan, patio and a garage space. The spacious main living space features a corner gas log fireplace, breakfast bar, SS appliances, granite counters and newer laminate flooring. The ensuite primary bedroom has a walk-in closet and steam shower. Two more bedrooms provide space for a home office

    Marie Levesque Compass

    844 E 40th St Unit A2, Chicago, IL 60653
    • /29

      Est $665,626 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 3,100 Sq Ft

      4120 S Berkeley Ave, Chicago, IL 60653

      4120 S Berkeley Ave, Chicago, IL 60653
  • /11

    $224,999

    • 2 Beds
    • 1.5 Baths
    • 1,300 Sq Ft

    3811 S Langley Ave Unit 301, Chicago, IL 60653

    Welcome home to this sunlit 2-bedroom, 1.5-bath penthouse condo-just steps from Lake Michigan and minutes from downtown! Perched on the top floor of a well-maintained building, this residence boasts an open-concept layout ideal for entertaining. The bright and spacious living room sits at the front of the unit, flowing seamlessly into a combined dining area and open kitchen, creating the perfect

    Danielle Dowell Berkshire Hathaway HomeServices Chicago

    3811 S Langley Ave Unit 301, Chicago, IL 60653
  • /30

    $3,700 per month

    • 4 Beds
    • 2 Baths
    • 1,900 Sq Ft
    • Condo for Rent

    4021 S Ellis Ave Unit 5S, Chicago, IL 60653

    PURE LUXURY, 4 bed/2 bath condo available 9/1! Live large in this top floor, stunning newer construction unit, featuring beautiful hardwood floors throughout, updated Chef's kitchen, with high-end appliances and tons of storage. Master Bedroom has private balcony & WIC with built in shelving. All closets feature custom California Closets. Unit features rooftop deck, washer & Dryer in Unit, garage

    Desmond Lathan Fulton Grace Realty

    4021 S Ellis Ave Unit 5S, Chicago, IL 60653
  • /13

    $128,000 Sold May 29, 2025

    • Land
    • 0.07 Acre
    • $1,828,571 per Acre
    • 169 Days On Market

    3616 S Lake Park Ave, Chicago, IL 60653

    What an amazing opportunity to build your dream home or investment property in the vibrant area of Bronzeville... known for its beautiful beaches, cultural landmarks and expansive parks... With this property being zoned RM-5 this allows you to build up to (4) stories high for a stunning view of the lake. This property sits in an ideal location... right down the street from the 35th St.

    Paula Boudos Keller Williams Preferred Rlty

    3616 S Lake Park Ave, Chicago, IL 60653
    • /15

      Est $354,740 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,300 Sq Ft

      3735 S Lake Park Ave Unit 2S, Chicago, IL 60653

      3735 S Lake Park Ave Unit 2S, Chicago, IL 60653
  • /24

    $355,000 Open Sat 10AM - 2PM

    • 3 Beds
    • 2.5 Baths
    • 2,300 Sq Ft

    3733 S Lake Park Ave Unit 1, Chicago, IL 60653

    This is an amazing space! It's a 2,300 square foot, 3 bedrooms, 2.1 bathrooms, 1st floor condo. Spacious kitchen with granite counter top and stainless steel appliances. And it includes 1 garage space, in unit laundry, and private deck. This condo is fabulous!

    Loretta Fields On Point Realty Pros LLC

    3733 S Lake Park Ave Unit 1, Chicago, IL 60653
  • /20

    $3,000 per month

    • 2 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Condo for Rent

    4234 S Ellis Ave Unit 4B, Chicago, IL 60653

    Available 9/16. Come check out this stunning Penthouse unit in a boutique elevator building in the Heart of Bronzeville! This spacious 2 bed, 2 bath condo features hardwood flooring throughout, extra tall ceilings, designer light fixtures, southern exposure with tons of light, and more. The open concept kitchen boasts white shaker cabinets with crown moulding, granite countertops and backsplash,

    Matt Engle Fulton Grace Realty

    4234 S Ellis Ave Unit 4B, Chicago, IL 60653
  • /40

    $659,000 Sold May 20, 2025

    • 3,436 Sq Ft
    • $192/SF
    • 11 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 1888

    1034 E 41st Place, Chicago, IL 60653

    This extensively renovated 3-story, 5-bedroom, 3.5-bath Graystone is located on a landmark block in Chicago's Oakland neighborhood -- an architecturally rich enclave between Kenwood and Bronzeville. Ideally situated near parks, Lake Shore Drive, and the 41st Street Pedestrian Bridge, it offers easy access to lakefront recreation and an effortless commute to downtown or Hyde Park. After an

    Jennifer Ames Engel & Voelkers Chicago

    1034 E 41st Place, Chicago, IL 60653
    • /28

      Not Listed For Sale

      • 7 Beds
      • 4 Baths
      • 4,549 Sq Ft

      4123 S Drexel Blvd, Chicago, IL 60653

      4123 S Drexel Blvd, Chicago, IL 60653
  • /20

    $350,000

    • 3 Beds
    • 2 Baths
    • 1,800 Sq Ft

    4105 S Drexel Blvd Unit 1N, Chicago, IL 60653

    Welcome home to your beautiful new 3 bedroom/2 bathroom condo in the highly sought out Oakland area with a gated parking spot and large storage unit! You'll live right on the lush and historic Drexel Boulevard, just a short walk to 41st Street Beach. You're going to love the wood and marble fireplace, updated sparkling quartz kitchen countertops, stainless steel appliances, in-unit front loading

    Keesha Merritt Coldwell Banker Realty

    4105 S Drexel Blvd Unit 1N, Chicago, IL 60653
  • /18

    $2,250 per month

    • 2 Beds
    • 1.5 Baths
    • 950 Sq Ft
    • Condo for Rent

    926 E 43rd St Unit 303, Chicago, IL 60653

    38 units boutique rental development in popular Bronzeville neighborhood; parking space included in rent; elevator; washer and dryer in the unit; several units have balconies; Kinzini kitchens; SS appliances; quartz countertops; elegant bathrooms; individual heat and AC controls; tankless water heaters; high efficiency HVAC; close foam insulation on all outside walls, soundproofing in floors and

    Joanna Olszynska Compass

    926 E 43rd St Unit 303, Chicago, IL 60653
  • /14

    $268,000 Sold Apr 30, 2025

    • 2,584 Sq Ft
    • $104/SF
    • 154 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 2003

    4068 S Lake Park Ave Unit 1, Chicago, IL 60653

    Condo- Simply move in! Hardwood floors. New carpet installed. Parking included! This is a must see! Close to all accommodations including schools, parks, shops, restaurants and more! 2 levels of living space. Private Patio. Fireplace. Gourmet Kitchen with granite counters and Stainless Steel appliances. Luxury Master Bath with Walk in Shower and whirlpool. Close to 41st St Pedestrian Bridge,

    Christopher Lobrillo Grandview Realty, LLC

    4068 S Lake Park Ave Unit 1, Chicago, IL 60653
    • /31

      Not Listed For Sale

      • 7 Beds
      • 3 Baths
      • 3,441 Sq Ft

      3604 S Lake Park Ave, Chicago, IL 60653

      3604 S Lake Park Ave, Chicago, IL 60653
  • /14

    $450,000

    • 3 Beds
    • 2.5 Baths

    4226 S Ellis Ave Unit 4S, Chicago, IL 60653

    Newer construction 3 bed/2.5 bath in booming Kenwood! Top floor unit with spacious floor plan and tall ceilings allows for plenty of natural light. Highly upgraded chef's kitchen includes modern cabinetry, Quartz countertops, island bar and high-end stainless steel appliances. Combined living/dining room with a modern fireplace, surround sound speakers, covered balcony and 1/2 bath off of kitchen

    Michelle Michalski Berkshire Hathaway HomeServices Chicago

    4226 S Ellis Ave Unit 4S, Chicago, IL 60653
  • /22

    $2,995 per month

    • 3 Beds
    • 2 Baths
    • 1,900 Sq Ft
    • Apartment for Rent

    4014 S Drexel Blvd Unit 3R, Chicago, IL 60653

    Gorgeous 3 Bed 2 Bath, Living/Dining, 2 Outdoor Spaces. Available furnished or unfurnished. Updated Unit. In-Unit Washer/Dryer. Central Air/Heat. Pets at the Owner's discretion with a $ 50.00 pet rent per month, upon approval (No aggressive breeds or puppies). There is a one-time non-refundable Move-in fee of $ 1000.00 in lieu of no Security Deposit. Parking is Included in the rent. Available Now

    Ankeit Ghai RCI Realty LLC

    4014 S Drexel Blvd Unit 3R, Chicago, IL 60653
  • /29

    $334,900 Sold Apr 18, 2025

    • 1,800 Sq Ft
    • $186/SF
    • 58 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2007

    3932 S Lake Park Ave Unit 2S, Chicago, IL 60653

    Are you looking to take it to the next level for your new home in the city? Do you love to cook and entertain? Want to be close to everything but not congested in downtown traffic. Do you love the outdoors? How about a walk or bike ride along the lakefront? This beautiful 3 bed 2 bath condo is waiting for you! Enjoy 10-foot-high ceilings and an open concept perfect for entertaining with beautiful

    O'Neia Washington O W Auction Group LLC

    3932 S Lake Park Ave Unit 2S, Chicago, IL 60653
    • /13

      Est $275,794 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,600 Sq Ft

      4248 S Drexel Blvd Unit GN, Chicago, IL 60653

      4248 S Drexel Blvd Unit GN, Chicago, IL 60653
  • /15

    $299,900

    • 2 Beds
    • 2 Baths
    • 2,000 Sq Ft

    3976 S Ellis Ave Unit GS, Chicago, IL 60653

    Discover this stunning condo just minutes from downtown and steps away from Oakwood Beach and Lakeshore Drive. Stunning and completely updated, this gorgeous 2004 construction condo with 2-bedrooms and 2-bathrooms in the highly desirable Oakland/North Kenwood area. Soaring 12FT ceilings make this bright garden feel open and airy. Spacious kitchen with 42" maple shaker style cabinets, huge island

    Christopher Pertile Compass

    3976 S Ellis Ave Unit GS, Chicago, IL 60653
  • /2

    $2,700 per month

    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • House for Rent

    4204 S Drexel Blvd, Chicago, IL 60653

    VINTAGE BLDG.DUPLEX 3 BEDROOMS 2 BATHS MOVE IN CONDITION,HARDWOOD FLOORS, PRIVATE DECK,WASHER AND DRYER HOOKUPS,GREAT AREA !

    Magdalena Gruszka Archer Home Center

    4204 S Drexel Blvd, Chicago, IL 60653
  • /31

    $725,000 Sold Apr 14, 2025

    • 3,300 Sq Ft
    • $220/SF
    • 4 Beds
    • 3.5 Baths
    • Built 1893

    3982 S Lake Park Ave, Chicago, IL 60653

    Stately Vintage 3 story Greystone. Current owner a long time Chicago architect has loving restored the home maintaining much of the original charm and character. The home features a sprawling open floor plan full of character at every turn. Patterned mahogany wainscoting wrap 3 stunning levels of stairs, intricate ornamental plaster ceiling inlays, turret rooms, 7 fireplaces, and a turn of the

    Matthew Mika Compass

    3982 S Lake Park Ave, Chicago, IL 60653
    • /17

      Est $334,154 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,600 Sq Ft

      3631 S Cottage Grove Ave Unit 4, Chicago, IL 60653

      3631 S Cottage Grove Ave Unit 4, Chicago, IL 60653
  • /30

    $1,692,600

    4043 S Drexel Blvd, Chicago, IL 60653

    Exceptional 2006-built 8-units located in the heart of the rapidly appreciating Bronzeville neighborhood. This well-maintained, elevator building features eight spacious units available with separate utilities, ensuring ease of management and lower operating costs. Investors will appreciate the 8 exterior parking spaces, plus a garage space, offering ample tenant parking-a rare find in the area.

    Adam Zagata Baird & Warner

    4043 S Drexel Blvd, Chicago, IL 60653
  • /21

    $295,000 Sold Apr 11, 2025

    • 1,735 Sq Ft
    • $170/SF
    • 3 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2008

    4105 Maryland Ave, Chicago, IL 60653

    Welcome to 4105 S Maryland, a four-level townhome nestled in a private Bronzeville community. This property, offered as-is, has served as a rental for the past decade and presents an excellent opportunity for those looking to invest in a home with immense potential. While it requires some cosmetic updates, these enhancements are poised to significantly boost the property's value. The townhome

    Joshua Mercer Premier Chicago Real Estate

    4105 Maryland Ave, Chicago, IL 60653
    • /26

      Est $305,629 Not Listed For Sale

      • 3 Beds
      • 2 Baths

      822 E Bowen Ave Unit 3A, Chicago, IL 60653

      822 E Bowen Ave Unit 3A, Chicago, IL 60653
  • /13

    $221,500

    • 2 Beds
    • 1.5 Baths
    • 1,200 Sq Ft

    3817 S Ellis Ave Unit 101, Chicago, IL 60653

    This beautifully updated 2-bedroom, 1.5 bath condo on a quiet, tree-lined street near the picturesque shores of Lake Michigan perfectly blends modern comfort and convenient living. Enter to find a great open concept kitchen, living room/dining room area with an abundance of natural light, creating a warm atmosphere ideal for relaxation and entertaining. The updated kitchen includes a large

    Maya Puentes Baird & Warner

    3817 S Ellis Ave Unit 101, Chicago, IL 60653
  • /39

    $650,000 Sold Apr 04, 2025

    • 3,300 Sq Ft
    • $197/SF
    • 0 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2005

    817 E 38th St, Chicago, IL 60653

    Discover this stunning 4-bedroom, 3.5-bath single-family home in the sought-after Oakland community of Bronzeville! This beautifully designed home offers an ideal layout, with three bedrooms on the second floor, including a spacious primary suite with a private en-suite bath. The fully finished lower level (completed in 2022) features a versatile fourth bedroom, perfect as a second primary suite

    Krystal Corley RE/MAX Premier

    817 E 38th St, Chicago, IL 60653
    • /12

      Est $241,803 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,500 Sq Ft

      4165 S Ellis Ave Unit 1N, Chicago, IL 60653

      4165 S Ellis Ave Unit 1N, Chicago, IL 60653
  • /23

    $275,000

    • 2 Beds
    • 1 Bath
    • 1,200 Sq Ft

    4226 S Ellis Ave Unit 1B, Chicago, IL 60653

    Experience the perfect combination of historic charm, modern style, and everyday comfort in this condominium located in the heart of North Kenwood. Spanning approximately 1,200 square feet, this beautifully designed two-bedroom, one-bathroom home offers a bright and open layout ideal for both entertaining and relaxing. The spacious living area is flooded with natural light and seamlessly connects

    Paulette Edwards Coldwell Banker Realty

    4226 S Ellis Ave Unit 1B, Chicago, IL 60653
  • /31

    $219,000 Sold Mar 28, 2025

    • 1,200 Sq Ft
    • $182/SF
    • 137 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 2003

    825 E 41st St Unit 2B, Chicago, IL 60653

    Beautiful!!! Your Client will Love this Awesome Condo. 2 Bedrooms, 1.1 bath, Laundry room, attached indoor parking. Garbage disposal. Condo include Stove, Refrigerator, washer, dryer, and Microwave. There is a deck near the dining area. Property is minutes from downtown Chicago and walking distance to the lake, parks, and public transportation. Property show very well. This is a must see. easy

    Rochelle Williams Royal Kingdom Realty Inc.

    825 E 41st St Unit 2B, Chicago, IL 60653
    • /20

      Est $286,091 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,250 Sq Ft

      4010 S Drexel Blvd Unit 2S, Chicago, IL 60653

      4010 S Drexel Blvd Unit 2S, Chicago, IL 60653
  • /2

    $220,000

    • Land
    • 0.43 Acre
    • $511,628 per Acre

    4548 S Cottage Grove Ave, Chicago, IL 60653

    This is for vacant land, zoned B1-1 commercial, and is located in the hot Bronzeville community. This 125'x125' plot of land offers unlimited possibilities in an outstanding location. New construction and development all around in Bronzeville HOT** HOT**HOT DEAL**** 4546/4548 S, COTTAGE GROOVE AVAILABLE FOR SALE DOUBLE PACKAGE

    Ola Sanni Centurion Realty & Estates Inc

    4548 S Cottage Grove Ave, Chicago, IL 60653
  • /17

    $403,000 Sold Feb 28, 2025

    • 2,200 Sq Ft
    • $183/SF
    • 140 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2007

    3968 S Ellis Ave Unit 2S, Chicago, IL 60653

    Beautiful Oakland condo for sale! This second floor east facing condo boasts 3 Bedrooms and 2 Bathrooms. It features beautiful hardwood floors with an open concept layout, gas fireplace, a large stainless steel Kitchen with granite counter tops and island. The master bedroom spacious with a walk-in closet and master bath. In-unit washer and dryer hook-up. The bonus is the beautiful back deck for

    Kimberly Offord Coldwell Banker Realty

    3968 S Ellis Ave Unit 2S, Chicago, IL 60653
    • /12

      Est $270,782 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,500 Sq Ft

      3932 S Lake Park Ave Unit 1N, Chicago, IL 60653

      3932 S Lake Park Ave Unit 1N, Chicago, IL 60653
  • /12

    $370,000 Pending

    • 3 Beds
    • 2 Baths
    • 1,700 Sq Ft

    3862 S Lake Park Ave Unit 3S, Chicago, IL 60653

    Welcome to your 3-bedroom, 2-bath condo nestled in the Kenwood/Oakland area! Just a 2-minute walk takes you and your pup to the nearby dog park and Oakwood Beach! You'll also be just minutes from the vibrant shops and dining options in Bronzeville and Hyde Park. This spacious open-concept condo offers beautiful hardwood flooring, sleek granite countertops, stainless steel appliances, in-unit

    Aliyah Perkins eXp Realty

    3862 S Lake Park Ave Unit 3S, Chicago, IL 60653
  • /64

    $650,000 Sold Feb 05, 2025

    • 67 Days On Market
    • 7 Beds
    • 9 Baths
    • Built 1884

    4020 S Drexel Blvd, Chicago, IL 60653

    Wonderful 3 Unit Building. Each Unit Features Hardwood Flooring, 6 Panel Oak Doors & Trim, Updated Kitchen and baths. Separate Heating & Cooling Systems for each Unit along with In-Unit Laundry in Each Unit and Separate Electric Service . Front Entry plus Alley Access to the back of the building. Separate TAX ID's for All Three Units. Property can be utilized as a 3 Unit Building or finish

    Susan Miller Ravinia Realty & Mgmt LLC

    4020 S Drexel Blvd, Chicago, IL 60653
    • /16

      Est $248,048 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 8,448 Sq Ft

      3843 S Langley Ave Unit 201, Chicago, IL 60653

      3843 S Langley Ave Unit 201, Chicago, IL 60653
  • /2

    $295,000 Pending

    • 7 Beds
    • 4 Baths

    816 E 42nd St, Chicago, IL 60653

    INVESTORS ONLY - Code violations and receiver appointed. CASH ONLY. Buyer responsible for all repairs. Buyer must view the property and violations before submitting an offer. THIS IS A SHORT SALE, lender must approve.

    Robert Robinson MRS Real Estate Firm

    816 E 42nd St, Chicago, IL 60653

Showing Results 1 - 40, Page 1 of 18

Home Trends in Oakland, IL

Housing Trends

Median Sale Price
$422,000
Median Single Family Sale Price
$422,000
Median 2 Bedroom Sale Price
$74,900
Average Price Per Sq Ft
$143
Number of Homes for Sale
2
Last 12 months Home Sales
6
Months of Supply
4.00
Median List Price
$479,000
Median Change From 1st List Price
12%
Median Home Sale Price YoY Change
-16%
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