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Explore Similar Townhomes Within 2 Miles of Oakland, IL

  • /40

    $1,350,000

    • 3 Beds
    • 4 Baths

    1917 S Calumet Ave, Chicago, IL 60616

    Welcome to 1917 South Calumet Avenue, a stunning embodiment of modern luxury nestled in the Historic Prairie District of the South Loop. This impeccably designed three-bedroom, two full and two half bathroom townhome boasts an expertly crafted living space with completely customized modern touches. Features include heated herringbone hardwood floors on all levels, an inviting 60-inch vent free

    Agent Photo

    Nadine Ferrata

    Compass

    (773) 328-8035

    1917 S Calumet Ave, Chicago, IL 60616
  • /25

    $925,000

    • 3 Beds
    • 2.5 Baths

    4840 S Dorchester Ave Unit A, Chicago, IL 60615

    The Dorchester Collection is a newly-constructed elegant gated townhome development located in the prestigious Hyde Park/Kenwood neighborhood. A total of 13 townhouses are supported by a courtyard, a communal garden, and a landscape front yard. This 3 bedroom, 2.5 bath townhome is a dream for anyone looking for something a little extra from their home. The one-of-the-kind 3-story luxury residence

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    David Schatz

    Baird & Warner

    (872) 285-7391

    4840 S Dorchester Ave Unit A, Chicago, IL 60615
  • /24

    $850,000

    • 4 Beds
    • 3.5 Baths

    4840 S Dorchester Ave, Chicago, IL 60615

    6 out of 13 units sold! The Dorchester Collection is a newly-constructed elegant gated townhome development located in the prestigious Hyde Park/Kenwood neighborhood. A total of 13 townhouses are supported by a courtyard, a communal garden, and a landscape front yard. This 4 bedroom, 3.5 bath townhome is a dream for anyone looking for something a little extra from their home. This stunning facade

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    David Schatz

    Baird & Warner

    (872) 335-3203

    4840 S Dorchester Ave, Chicago, IL 60615
  • /20

    $1,100,000

    • 4 Beds
    • 3.5 Baths

    4840 S Dorchester Ave Unit 11, Chicago, IL 60615

    6 out of 13 units sold! The Dorchester Collection is a newly-constructed elegant gated townhome development located in the prestigious Hyde Park/Kenwood neighborhood. A courtyard, a communal garden, and a landscape front yard support a total of 13 townhouses. This 4 bedroom, 3.5 bath townhome is a dream for anyone looking for something a little extra from their home. This stunning facade is

    Agent Photo

    David Schatz

    Baird & Warner

    (872) 312-9193

    4840 S Dorchester Ave Unit 11, Chicago, IL 60615
  • /35

    $1,550,000

    • 3 Beds
    • 4.5 Baths
    • 3,797 Sq Ft

    1733 S Prairie Ave, Chicago, IL 60616

    Welcome to an exquisite residence at 1733 South Prairie Avenue, located in the heart of Chicago's Historic Prairie District. This elegant three-bedroom, four and a half bath townhome is a true modern masterpiece, offering 3,797 square feet of living space. As you approach, you'll be greeted by a gated front yard and garden, leading to a charming patio perfect for outdoor relaxation. Step inside

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    Nadine Ferrata

    Compass

    (872) 324-3917

    1733 S Prairie Ave, Chicago, IL 60616
  • /28

    $710,000

    • 3 Beds
    • 2.5 Baths
    • 2,400 Sq Ft

    5414 S Greenwood Ave Unit 2, Chicago, IL 60615

    Enormous Hyde Park Townhome with 2400 interior SF, additional three outdoor spaces and two car plus garage. Overlooking gorgeous Stout Park literally outside your front door. Entry level is a big rec room, outdoor patio, generous closet space and wet bar hook-up along with direct access to your 2 car plus garage. On the main living level, views of the park greenery greet you from your living

    Ann Carson @properties Christie's International Real Estate

    5414 S Greenwood Ave Unit 2, Chicago, IL 60615
  • /23

    $499,800

    • 3 Beds
    • 3.5 Baths
    • 2,500 Sq Ft

    4926 S Cornell Ave Unit C, Chicago, IL 60615

    Rarely available and truly move-in ready, this spacious Cornell Square townhome offers the comfort of a single-family home in an exceptional location. Nestled on a quiet, tree-lined one-way street, this 3-bedroom, 3.1-bath residence spans three levels of thoughtfully designed living space and includes a private, attached 2-car garage. Enter inside to a welcoming foyer that leads to a versatile

    Mike Checuga RE/MAX PREMIER

    4926 S Cornell Ave Unit C, Chicago, IL 60615
  • /25

    $498,999 Open Sat 11AM - 1PM

    • 3 Beds
    • 3 Baths
    • 2,200 Sq Ft

    4530 S Woodlawn Ave Unit 102, Chicago, IL 60653

    Rare opportunity to own in the Private Shakespeare Townhome New luxury flooring installed in office/bedroom/family room and foyer (5/5/2025). New Carpet installed in all bedrooms and 2nd floor stairs (5/5/2025). Level 2 EV charger installed (2025).New smart stainless steel appliances (2025). New Quartz countertops (2025) New furnace (2025) A gorgeous, huge, three-story townhome in North Kenwood,

    Lorenzo Garth HomeSmart Connect LLC

    4530 S Woodlawn Ave Unit 102, Chicago, IL 60653
  • /17

    $485,000

    • 3 Beds
    • 3 Baths
    • 2,187 Sq Ft

    308 E 25th Place, Chicago, IL 60616

    Prime Location Near McCormick Place & Lake Michigan! Located within walking distance to McCormick Place Convention Center and just a 12-minute drive to 12th Street Beach by Adler Planetarium, this bright and spacious townhome offers the feel of a single-family home. With north and south-facing windows, natural light fills every level. The main level features a versatile space perfect for a home

    Carmen Zhen Coldwell Banker Realty

    308 E 25th Place, Chicago, IL 60616
  • /45

    $479,000

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

    353 E Eastgate Place, Chicago, IL 60616

    Built in 2007, featuring 3-Levels of living space with 2 bedrooms, 3 full baths approximately 2,000 Sq. ft. Kitchen Island with S.S. appliances, hardwood floors, 2nd level deck with gas pipeline for BBQ, and roof top deck. 2-Attached car garage. Convenient location with short distance and access to I-55, Dan Ryan, Kennedy, Lake Shore Dr., Parks, Soldier Field, Lakefront via the 18th St. bridge,

    Mark Ahmad Century 21 Circle

    353 E Eastgate Place, Chicago, IL 60616
  • /25

    $605,000

    • 4 Beds
    • 2.5 Baths
    • 2,500 Sq Ft

    4721 S Woodlawn Ave Unit E, Chicago, IL 60615

    One dedicated parking space is included right at the front door. Located near Metra transportation, the University of Chicago and all the Hyde Park and Kenwood communities have to offer! Over 2500 Square feet of living space.

    Tammy Jackson KM Realty Group, LLC

    4721 S Woodlawn Ave Unit E, Chicago, IL 60615
  • /14

    $485,000

    • 2 Beds
    • 2 Baths
    • 1,850 Sq Ft

    2321 S Wabash Ave Unit 12, Chicago, IL 60616

    Beautiful courtyard community in the rapidly developing South Loop area. 3-story townhouse featuring 2 bedrooms, large multi-purpose room, 2 baths, deck & attached 2-car garage. Granite kitchen countertops, newly refinished bathroom, washer & dryer, garbage disposal, hardwood floors in open floor plan living/dining room & kitchen. End unit with north, south and east exposure. Close to the Loop,

    Ran Cao Concentric Realty Inc.

    2321 S Wabash Ave Unit 12, Chicago, IL 60616
  • /17

    $535,000

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

    70 E 18th St Unit 4E, Chicago, IL 60616

    Lovely penthouse duplex loft in Chicago's exciting South Loop! 20 foot atrium is at the heart of this home with double height windows and pretty south facing neighborhood and city views. Great private terrace! 3 nice sized bedrooms with an abundance of closets and two full baths. Intimate boutique building with convenient access to the lakefront trail, Museum Campus, Chicago Women's Park and

    Cara Buffa Berkshire Hathaway HomeServices Chicago

    70 E 18th St Unit 4E, Chicago, IL 60616
  • /31

    $899,000

    • 3 Beds
    • 4 Baths
    • 2,815 Sq Ft

    324 E 17th St Unit 324, Chicago, IL 60616

    Welcome to this expansive and sun-drenched 3-bedroom, 4-bathroom corner-unit townhouse, perfectly positioned in the heart of the South Loop's coveted Prairie District. With over 2800 square feet of thoughtfully designed living space, this home offers exceptional flexibility to meet today's lifestyle needs. Enjoy three distinct outdoor retreats: a ground-level patio with low-maintenance

    Nancy Simonson Keller Williams ONEChicago

    324 E 17th St Unit 324, Chicago, IL 60616
  • /13

    $525,000

    • 3 Beds
    • 1.5 Baths
    • 1,400 Sq Ft

    1428 E 55th St, Chicago, IL 60615

    Exceptional opportunity for homeownership! At the most desirable location of Hyde Park, this charming 3-bedroom, 1.5-bathroom townhouse offers 1,400 sq ft of living space. Built in 1964, by renowned architects I.M. Pei. The home features solid oak hardwood floors throughout with skylight, and a big private yard. Conveniently situated near the University of Chicago campus, shopping centers, and

    Megan Chen Prosperity Homes Co.

    1428 E 55th St, Chicago, IL 60615
  • /5

    $900,000 New Construction

    • 4 Beds
    • 3.5 Baths

    4719 S Ingleside Ave, Chicago, IL 60615

    Come and See These State of the Art Row Homes. The rarity of new construction in a historical setting like the Kenwood community is just the beginning. Each of the homes has been designed with a full masonry exterior for maximum durability, architectural aesthetic comfort, quiet and enjoyment. Interior design elements have been carefully selected and incorporate a variety of textures and choice

    Wilfredo Aguilar Compass

    4719 S Ingleside Ave, Chicago, IL 60615
  • /14

    $315,000

    • 2 Beds
    • 2 Baths

    4532 S Woodlawn Ave, Chicago, IL 60653

    Welcome to this beautifully maintained 2-bedroom, 2-bathroom townhome offering a perfect blend of comfort and convenience. The spacious kitchen boasts ample cabinet space, stainless steel appliances, and an eat-in counter, ideal for everyday living and entertaining. It opens seamlessly into a large living room highlighted by hardwood floors and a cozy gas log fireplace. Venture outside to a

    Scott Newman Keller Williams ONEChicago

    4532 S Woodlawn Ave, Chicago, IL 60653
  • /9

    $150,000

    • 2 Beds
    • 1 Bath
    • 960 Sq Ft

    75 E 37th Place, Chicago, IL 60653

    Attention investors! This 2-bedroom, 1-bathroom property in the heart of Bronzeville is an income-producing asset with a tenant already in place, leased at 1,500/month until August 1st, 2025. Enjoy a steady cash flow from day one without the hassle of securing a renter. Located just blocks from Illinois Institute of Technology (IIT), Guaranteed Rate Field (White Sox Stadium), and Mariano's, this

    Nadiia Glavin Keller Williams ONEChicago

    75 E 37th Place, Chicago, IL 60653
  • /10

    $150,000

    • 2 Beds
    • 1.5 Baths

    109 E 37th Place, Chicago, IL 60653

    Attention investors! This 2-bedroom, 1-bathroom townhome in the heart of Bronzeville is an income-producing asset with a tenant already in place, leased at $1,500/month until the end of March, 2026. Enjoy a steady cash flow from day one without the hassle of securing a renter. Located just blocks from Illinois Institute of Technology (IIT), Guaranteed Rate Field (White Sox Stadium), and

    Nadiia Glavin Keller Williams ONEChicago

    109 E 37th Place, Chicago, IL 60653
  • /30

    $335,000

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

    4102 S Cottage Grove Ave Unit 3S, Chicago, IL 60653

    Welcome home to this stunning and spacious duplex condo in historic Bronzeville! Offering 3 bedrooms, 3 full bathrooms, and an impressive 2,700 square feet, this duplex-up gem blends modern comfort with classic charm. Step inside to a bright, open layout featuring a chef's stove, 42" hardwood cabinets with granite countertops, a cozy gas fireplace, and exposed brick walls. Enjoy the convenience

    Rene Perez eXp Realty

    4102 S Cottage Grove Ave Unit 3S, Chicago, IL 60653
  • /20

    $429,900

    • 2 Beds
    • 2 Baths
    • 1,401 Sq Ft

    2305 S Wabash Ave, Chicago, IL 60616

    This South Loop townhouse has three levels of living space, each featuring oak floors. Entry level features an office, full bathroom and attached two car garage. The second level features kitchen with granite countertops, living room with fireplace and balcony off kitchen. Two bedrooms, a full bath and laundry on the third level. SELLER DOES NOT PROVIDE SURVEY. Seller is open to concessions

    Robert Padron Re/Max Cityview

    2305 S Wabash Ave, Chicago, IL 60616
  • /26

    $420,000

    • 3 Beds
    • 1.5 Baths
    • 1,548 Sq Ft

    2237 S Stewart Ave, Chicago, IL 60616

    Great Chinatown location, close to shopping, restaurant, bus train station and easy assess express free way, three level townhouse, 3 bedroom and 1.5 baths, gated community, central heat and air,, hardwood floor through out the whole house, kitchen with all appliance, washer and dryer and roof deck and one car garage.

    Qian Kun Chen Kale Realty

    2237 S Stewart Ave, Chicago, IL 60616
  • /17

    $189,900

    • 2 Beds
    • 1 Bath
    • 848 Sq Ft

    5214 S Calumet Ave, Chicago, IL 60615

    Completely re-designed and rehabbed to perfection... Heres a Great home for a small family or an investor looking to add to the Portfolio... Take a look at this newly rehabbed Townhome located in a desirable area where the property values are on the rise... Schedule an appointment and take advantage of a rare opportunity to own at a great price in a Historic neighborhood...

    LeRoy Willis LeRoy L. Willis

    5214 S Calumet Ave, Chicago, IL 60615
  • /20

    $375,000

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

    1166 E 54th St, Chicago, IL 60615

    Click the 3D tour! Historic Greystone rowhome in a prime Hyde Park location! This gorgeous Greystone is located just blocks from the University of Chicago and within walking distance to the main business corridors of Hyde Park. Situated on a tree lined one way street, this home features three spacious bedrooms on the same level, an updated kitchen with stainless steel appliances and granite

    Lane Chesebro Coldwell Banker Realty

    1166 E 54th St, Chicago, IL 60615
  • /2

    $75,000

    • 2 Beds
    • 1 Bath
    • 1,037 Sq Ft

    4808 S Drexel Blvd Unit N, Chicago, IL 60615

    This property needs your special touches.

    Nicole Wheatly EXIT Strategy Realty

    4808 S Drexel Blvd Unit N, Chicago, IL 60615
  • /2

    $384,000

    • 4 Beds
    • 2 Baths
    • 1,450 Sq Ft

    1409 E 49th St Unit 17, Chicago, IL 60615

    Rare Opportunity! Don't miss out on this incredible 3-story, 4-bedroom, 2-bathroom townhouse nestled in the highly sought-after Hyde Park/Kenwood neighborhood. Tenant-occupied (Month-to-Month) and generating income, this spacious property is a fantastic investment or future home! Completely rehabbed in 2017, featuring stunning kitchen with white cabinetry, granite countertops, full-height

    Omor Eguasa Baird & Warner

    1409 E 49th St Unit 17, Chicago, IL 60615
  • /30

    $1,375,000 New Construction

    • 5 Beds
    • 3.5 Baths
    • 3,415 Sq Ft

    1333 E Madison Park, Chicago, IL 60615

    Welcome home! Discover the elegance of this NEW Construction LUXURY Townhome residence, ready for immediate occupancy! Located and facing the desirable Madison Park in Hyde Park/Kenwood, residence 1333 is the east endcap and newly constructed townhome on the boulevard park. This sophisticated home, crafted by renowned developer ZSD and Studio Dwell, offers a modern and impeccable design with top

    Joanna Olszynska Compass

    1333 E Madison Park, Chicago, IL 60615

Why Live in Oakland

Oakland’s identity is firmly rooted in its evolution over the last century. Located next door to Bronzeville, a hub for African-American culture and business in the early 1900s, the community was long a casualty of historic redlining and housing discrimination. By the hands of local activists, Oakland today is compact with affordably-priced single-family homes, townhouses and condos—and new investors are still breaking ground. “As a homeowner, it’s great to see construction in our community because it brings equity to our homes,” says Shaena Flanagan, an Oakland resident and Luxury Property Specialist with Coldwell Banker Realty. “There were so many empty lots for so long; a lot of housing projects were finally torn down, and they’re never going back up.” The bustling community is home to locally-owned restaurants, shops and parks overlooking Lake Michigan. Residents even share monumental landmarks with neighboring Bronzeville, including Wendell Phillips Academy High School, the oldest predominately African-American high school in the city. At the height of the midcentury, the Chicago Housing Authority constructed several public housing projects in and around Oakland. Over the

Home Trends in Oakland, IL

Housing Trends

Median Sale Price
$334,950
Median Single Family Sale Price
$659,000
Median Townhouse Sale Price
$295,000
Median 2 Bedroom Sale Price
$220,350
Median 1 Bedroom Sale Price
$191,450
Average Price Per Sq Ft
$192
Number of Homes for Sale
7
Last 12 months Home Sales
26
Months of Supply
3.20
Median List Price
$334,900
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
-11%
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