Oakland Homes

/45
$350,000

Pending
- 3 Beds
- 2.5 Baths
- 1,600 Sq Ft
3735 S Lake Park Ave Unit G, Chicago, IL 60653

****H&B OFFERS DUE BY MIDNIGHT TONIGHT (8/13/26)**** This STUNNING villa remodel with GORGEOUS Kitchen and SHOW-STOPPING Bath are just what you've been waiting for -- A spacious and smart 3 Bed, 2.5 bath dream villa with Premium Luxury touches everywhere; THE KITCHEN: Beautiful Navy & Gold cabinets give style and class and Luxurious double-thick Quartz countertop give gravitas to the High-end

Gregory Sytsma @properties Christie's International Real Estate

3735 S Lake Park Ave Unit G, Chicago, IL 60653
Explore Oakland
/2
$3,100 Per Month
- 3 Beds
- 2.5 Baths
- 2,300 Sq Ft
- Condo for Rent
4060 S Ellis Ave Unit 1S, Chicago, IL 60653

Welcome to The Ethel, a luxury duplex-down condominium in the heart of North Kenwood-Oakland. This three-bedroom, 2.5-bath residence offers approximately 2,300 square feet of thoughtfully designed living space across two levels, with custom closets and custom window treatments throughout. The main level features hardwood floors, a bright living room, a dedicated dining area, and a convenient half

Maikol Akintonde

Coldwell Banker Realty

4060 S Ellis Ave Unit 1S, Chicago, IL 60653
/30
$1,466,920

Sold Mar 04, 2026

4043 S Drexel Blvd, Chicago, IL 60653
- Built 2003
Last Sold Summary
- 1% Above List Price
- 235 Days On Market
Last Listing Agent Loreal Urso Baird & Warner

4043 S Drexel Blvd, Chicago, IL 60653

/53
Est $177,000

Not Listed For Sale

3958 S Drexel Blvd, Chicago, IL 60653
- 5 Beds
- 4.5 Baths
- 4,000 Sq Ft
- Built 2019
3958 S Drexel Blvd, Chicago, IL 60653

Last Sold Summary
- 293 Days On Market
Last Listing Agent Arkadiusz Szejgiec Coldwell Banker Real Estate Group

/49
$344,900

Pre-Foreclosure
- 3 Beds
- 3 Baths
4105 S Drexel Blvd Unit 1SR, Chicago, IL 60653

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

Arturo Olivares Premier Choice Realty Inc

4105 S Drexel Blvd Unit 1SR, Chicago, IL 60653
/23
Starting at $1,218 Per Month
- 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

Lake Grove Village

3555 S Cottage Grove Ave, Chicago, IL 60653
/15
$75,000

Sold Sep 10, 2026

4344 S Vincennes Ave, Chicago, IL 60653
- Land
- 0 Sq Ft
Last Sold Summary
- 42% Below List Price
- 1 Day On Market
Last Listing Agent Amal Khalil Coldwell Banker Realty

4344 S Vincennes Ave, Chicago, IL 60653

/29
Est $420,344

Not Listed For Sale

4226 S Ellis Ave Unit 4N, Chicago, IL 60653
- 3 Beds
- 2.5 Baths
- 1,300 Sq Ft
- Built 2018
4226 S Ellis Ave Unit 4N, Chicago, IL 60653

Last Sold Summary
- 157 Days On Market
Last Listing Agent Carl Johnson Century 21 S.G.R., Inc.

/20
$272,000
- 2 Beds
- 1.5 Baths
- 1,640 Sq Ft
830 E Bowen Ave Unit 2A, Chicago, IL 60653

Welcome to this stunning newer-construction duplex in the heart of Bronzeville/North Kenwood. Located in the tranquil Jazz on the Boulevard community, this two-level home offers a rare blend of peaceful, park-like surroundings and vibrant city living-just minutes from the lakefront. The home is filled with natural light and features two generously sized bedrooms and one and a half bathrooms. The

Rafiq Abdullah Kale Realty

830 E Bowen Ave Unit 2A, Chicago, IL 60653
/14
$4,100 Per Month
- 3 Beds
- 3.5 Baths
- 2,400 Sq Ft
- Apartment for Rent
3991 S Drexel Blvd Unit C, Chicago, IL 60653

Well appointed and spacious 3-bedroom, 3.5-bath townhome situated in the one way cul-de-sac on Drexel Boulevard in Bronzeville. The home features an inviting open floor plan with hardwood floors throughout the main living areas. The generously sized primary suite offers vaulted ceilings and a marble bathroom with a whirlpool tub and separate shower. The lower-level third bedroom is ideal for

Jonathan Lavinier Baird & Warner

3991 S Drexel Blvd Unit C, Chicago, IL 60653
/30
$425,000

Sold Jun 26, 2026

3968 S Ellis Ave Unit 2N, Chicago, IL 60653
- 3 Beds
- 2 Baths
- 2,200 Sq Ft
- Built 2004
Last Sold Summary
- $193/SF
- 8 Days On Market
Current Estimated Value $424,251

Last Listing Agent Jean Walker Redfin Corporation

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

/2
Not Listed For Sale

4002 S Ellis Ave, Chicago, IL 60653
- 5 Beds
- 4 Baths
- 1,616 Sq Ft
- Built 1883
4002 S Ellis Ave, Chicago, IL 60653

Last Sold Summary
- 62 Days On Market
Last Listing Agent Takenya Moore TMM Realty Group LTD

/14
$199,900
- 1 Bed
- 1 Bath
- 908 Sq Ft
803 E 41st St Unit 1B, Chicago, IL 60653

Prime Bronzeville/North Kenwood condo with a rare private attached single space garage! This first floor walk-in unit features an open-concept layout with hardwood floors in the main living area, a large kitchen with a breakfast bar, bedroom has newer engineered flooring, and in-unit stackable laundry. Private fenced yard for grilling or enjoy the peaceful central community courtyard. Unbeatable

Walker Robinson RE/MAX Premier

803 E 41st St Unit 1B, Chicago, IL 60653
/21
$2,995 Per Month
- 3 Beds
- 2 Baths
- 1,700 Sq Ft
- Condo for Rent
3862 S Lake Park Ave Unit 1S, Chicago, IL 60653

Beautiful condo walking distance from the beach available for rent. Unit features 3 bedrooms, 2 bathrooms, granite countertops, hardwood floors throughout. There is laundry in the unit. Parking available for an additional $150. The bedrooms provide ample closet space and an impressive oversized master bathroom. Come see this unit today.

Genaro Bucio Selective Realty Services Inc

3862 S Lake Park Ave Unit 1S, Chicago, IL 60653
/20
$362,000

Sold Jun 05, 2026

4248 S Drexel Blvd Unit 3S, Chicago, IL 60653
- 3 Beds
- 2 Baths
- 1,700 Sq Ft
- Built 2008
Last Sold Summary
- 2% Above List Price
- $213/SF
- 6 Days On Market
Current Estimated Value $357,938

Last Listing Agent Eric Marcus Keller Williams ONEChicago

4248 S Drexel Blvd Unit 3S, Chicago, IL 60653

/28
Not Listed For Sale

4123 S Drexel Blvd, Chicago, IL 60653
- 7 Beds
- 4 Baths
- 4,549 Sq Ft
- Built 1908
4123 S Drexel Blvd, Chicago, IL 60653

Last Sold Summary
- 42 Days On Market
Last Listing Agent Sybil Martin Coldwell Banker Realty

/68
$2,150,000
3967 S Drexel Blvd, Chicago, IL 60653

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

Karen Biazar North Clybourn Group, Inc.

3967 S Drexel Blvd, Chicago, IL 60653
/14
$3,000 Per Month
- 3 Beds
- 2 Baths
- 1,600 Sq Ft
- Apartment for Rent
3723 S Lake Park Ave Unit 1, Chicago, IL 60653

New construction luxury apartments available for immediate move. Each unit features 3 bedrooms 2 bathroom. The master suite includes a private balcony, walk in closet and spa like master bathroom. Units features in unit washer/dryer, open open plan , lots of sunlight and top of the line appliances and finishes.

Colleen Berg Berg Properties

3723 S Lake Park Ave Unit 1, Chicago, IL 60653
/23
$285,000

Sold Feb 07, 2026

4014 S Drexel Blvd Unit 4R, Chicago, IL 60653
- 3 Beds
- 2 Baths
- 1,900 Sq Ft
- Built 1925
Last Sold Summary
- 8% Below List Price
- $150/SF
- 71 Days On Market
Current Estimated Value $301,905

Last Listing Agent John Hockberger @properties Christie's International Real Estate

4014 S Drexel Blvd Unit 4R, Chicago, IL 60653

/13
Est $247,257

Not Listed For Sale

4248 S Drexel Blvd Unit GN, Chicago, IL 60653
- 3 Beds
- 2 Baths
- 1,600 Sq Ft
- Built 2009
4248 S Drexel Blvd Unit GN, Chicago, IL 60653

Last Sold Summary
- 112 Days On Market
Last Listing Agent Janece Simmons EXIT Strategy Realty

/33
$799,000

$36K PRICE DROP
- 5 Beds
- 3 Baths
- 4,000 Sq Ft
4126 S Lake Park Ave, Chicago, IL 60653

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

Sheila Dantzler Jameson Sotheby's Intl Realty

4126 S Lake Park Ave, Chicago, IL 60653
/2
$947,000

Sold Jan 16, 2026

922 E 42nd Place, Chicago, IL 60653
- 6 Beds
- 4.5 Baths
- 2,316 Sq Ft
- Built 1888
Last Sold Summary
- 5% Below List Price
- $409/SF
- 78 Days On Market
Last Listing Agent Jennifer Bell Fulton Grace Realty

922 E 42nd Place, Chicago, IL 60653

/12
Est $361,586

Not Listed For Sale

3862 S Lake Park Ave Unit 3S, Chicago, IL 60653
- 3 Beds
- 2 Baths
- 1,700 Sq Ft
- Built 2007
3862 S Lake Park Ave Unit 3S, Chicago, IL 60653

Last Sold Summary
- 49 Days On Market
Last Listing Agent Aliyah Perkins eXp Realty

/23
$400,000

Pending
- 3 Beds
- 2.5 Baths
- 2,300 Sq Ft
3733 S Lake Park Ave Unit 1, Chicago, IL 60653

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

Loretta Fields On Point Realty Pros LLC

3733 S Lake Park Ave Unit 1, Chicago, IL 60653
/36
$615,000

Sold Jun 12, 2026

Unlisted Address
- 4 Beds
- 5 Baths
- 3,500 Sq Ft
- Built 2016
Last Sold Summary
- 1% Below List Price
- $176/SF
- 11 Days On Market
Current Estimated Value $611,221

Last Listing Agent Jessica Macey Real Broker LLC

Unlisted Address

/28
Est $387,587

Not Listed For Sale

3862 S Lake Park Ave Unit 3N, Chicago, IL 60653
- 3 Beds
- 2 Baths
- 1,850 Sq Ft
- Built 2007
3862 S Lake Park Ave Unit 3N, Chicago, IL 60653

Last Sold Summary
- 15 Days On Market
Last Listing Agent Kellye Jackson Redfin Corporation

/38
$775,000

Open Sun 10:30AM - 12PM
- 4 Beds
- 2.5 Baths
- 2,800 Sq Ft
3901 S Lake Park Ave, Chicago, IL 60653

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

Ardit Dizdari @properties Christie's International Real Estate

3901 S Lake Park Ave, Chicago, IL 60653
/26
$364,900

Sold Dec 15, 2025

4114 Maryland Ave, Chicago, IL 60653
- 3 Beds
- 2 Baths
- 2,200 Sq Ft
- Built 2008
Last Sold Summary
- 8% Below List Price
- $166/SF
- 93 Days On Market
Current Estimated Value $385,808

Last Listing Agent Carolyn Durocher Coldwell Banker Realty

4114 Maryland Ave, Chicago, IL 60653

/14
Est $228,261

Not Listed For Sale

3815 S Langley Ave Unit 301, Chicago, IL 60653
- 2 Beds
- 1.5 Baths
- 1,200 Sq Ft
- Built 2007
3815 S Langley Ave Unit 301, Chicago, IL 60653

Last Sold Summary
- 22 Days On Market
Last Listing Agent Jean Walker Redfin Corporation

/2
$350,000
- Land
- 4,356 Sq Ft
- $3,500,000 per Acre
4545 S Champlain Ave, Chicago, IL 60653

Explore the potential of this expansive lot located at 4545 S Champlain Avenue. This is a multizoned, double back lot. Nestled within a thriving area near the Obama Presidential Library, this parcel presents a unique opportunity to design and build in a community that values growth and development. Whether envisioning a residential project or a creative venture, the spacious grounds accord ample

Misael Chacon Beycome Brokerage Realty LLC

4545 S Champlain Ave, Chicago, IL 60653
/5
$489,112

Sold Mar 04, 2026

4043 S Drexel Blvd Unit 104, Chicago, IL 60653
- 3 Beds
- 3 Baths
- 2,500 Sq Ft
- Built 2005
Last Sold Summary
- 11% Above List Price
- $196/SF
Current Estimated Value $429,198

Last Listing Agent Brian Brak Brak Realty Inc.

4043 S Drexel Blvd Unit 104, Chicago, IL 60653

/15
Est $221,442

Not Listed For Sale

3815 S Langley Ave Unit 201, Chicago, IL 60653
- 2 Beds
- 1.5 Baths
- 1,086 Sq Ft
- Built 2007
3815 S Langley Ave Unit 201, Chicago, IL 60653

Last Sold Summary
- 37 Days On Market
Last Listing Agent Todd Hague 1st Cornerstone Realty Inc.

/4
$285,000
- Land
- 6,969 Sq Ft
- $1,781,250 per Acre
4600 S Champlain Ave, Chicago, IL 60653

Prime CORNER double lot in Bronzeville/Grand Boulevard could be your Next Big Build. A rare find on one of the South Side's fastest-moving corridors: 7,040 square feet of RT-4 zoned land, wrapped by two street frontages on a coveted corner. Ideally situated near neighborhood parks, Lake Michigan lakefront, beaches and trails, public transportation, Hyde Park, the South Loop, Museum Campus and

Kimberly Carmen Berkshire Hathaway HomeServices Chicago

4600 S Champlain Ave, Chicago, IL 60653
/24
$290,000

Sold Sep 26, 2025

3976 S Ellis Ave Unit GS, Chicago, IL 60653
- 2 Beds
- 2 Baths
- 1,875 Sq Ft
- Built 2004
Last Sold Summary
- 3% Below List Price
- $155/SF
- 9 Days On Market
Current Estimated Value $301,115

Last Listing Agent Paulette Edwards Coldwell Banker Realty

3976 S Ellis Ave Unit GS, Chicago, IL 60653

/12
Est $264,903

Not Listed For Sale

4165 S Ellis Ave Unit 1N, Chicago, IL 60653
- 2 Beds
- 2 Baths
- 1,500 Sq Ft
- Built 2007
4165 S Ellis Ave Unit 1N, Chicago, IL 60653

Last Sold Summary
- 49 Days On Market
Last Listing Agent Cherise Baggett Keller Williams Experience

/51
$639,900

Sold Jul 31, 2026

3761 S Lake Park Ave, Chicago, IL 60653
- 5 Beds
- 3 Baths
- 2,556 Sq Ft
- Built 2000
Last Sold Summary
- $250/SF
- 7 Days On Market
Last Listing Agent Benita Cathey The Margie Smigel Group, LLC

3761 S Lake Park Ave, Chicago, IL 60653

/39
Est $343,203

Not Listed For Sale

3932 S Lake Park Ave Unit 3N, Chicago, IL 60653
- 3 Beds
- 2 Baths
- 1,800 Sq Ft
- Built 2007
3932 S Lake Park Ave Unit 3N, Chicago, IL 60653

Last Sold Summary
- 109 Days On Market
Last Listing Agent O'Neia Washington O W Auction Group LLC

/16
$336,172

Sold Apr 10, 2026

3817 S Ellis Ave Unit 302, Chicago, IL 60653
- 3 Beds
- 2 Baths
- 1,700 Sq Ft
- Built 2006
Last Sold Summary
- 1% Below List Price
- $198/SF
- 26 Days On Market
Current Estimated Value $332,315

Last Listing Agent Fei Martin Berkshire Hathaway HomeServices Chicago

3817 S Ellis Ave Unit 302, Chicago, IL 60653

/29
Est $340,363

Not Listed For Sale

3932 S Lake Park Ave Unit 2S, Chicago, IL 60653
- 3 Beds
- 2 Baths
- 1,800 Sq Ft
- Built 2007
3932 S Lake Park Ave Unit 2S, Chicago, IL 60653

Last Sold Summary
- 58 Days On Market
Last Listing Agent O'Neia Washington O W Auction Group LLC

/3
$140,000

Sold Aug 10, 2026

614 E 43rd St, Chicago, IL 60653
- Land
- 0 Sq Ft
Last Sold Summary
- 1% Above List Price
- 12 Days On Market
Last Listing Agent Jason O'Beirne Jameson Sotheby's Intl Realty

614 E 43rd St, Chicago, IL 60653

Showing Results 1 - 40, Page 1 of 18

Illinois Cook County Chicago

Learn more about living in Oakland

Home Prices in Oakland, IL

The median home sale price in Oakland, Chicago is $354,000, up 2% year-over-year. Homes in Oakland sell in 62 days on average, compared to the national average of 55 days.

Home Price Trends

Median Sale Price $354,000	Median Single Family Sale Price $530,000
Median Townhouse Sale Price $386,000	Median 2 Bedroom Sale Price $266,409
Median 1 Bedroom Sale Price $202,450	Average Price Per Sq Ft $197
Number of Homes for Sale 1,628	Last 12 months Home Sales 29
Months of Supply 2.10	Median List Price $357,000
Median Change From 1st List Price 1%	Median Home Sale Price YoY Change 2%

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