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Explore Similar Houses Within 2 Miles of Oakland, IL

  • /33

    $1,699,900

    • 5 Beds
    • 5 Baths
    • 4,500 Sq Ft

    1150 E 49th St, Chicago, IL 60615

    Custom renovation in Historic Kenwood! Sophisticated single-family home offers a perfect blend of mid-century charm and modern living. Large garden is a lovely oasis which includes a private pergola and formal dining area. Dine al fresco with family and friends using the large outdoor cooking area and expansive front yard. The home was completely reconstructed to the studs by the owner. The

    Agent Photo

    Kimberly Chase-Harding

    Berkshire Hathaway HomeServices Chicago

    (773) 945-0384

    1150 E 49th St, Chicago, IL 60615
  • /24

    $1,895,000

    • 6 Beds
    • 6 Baths
    • 5,127 Sq Ft

    4942 S Ellis Ave, Chicago, IL 60615

    Huge Sunny Hyde Park/South Kenwood 6 bedroom Greystone is totally upgraded and has space to add a 2 car garage. Note that this Greystone is an end unit and is therefore only attached on one side and thus gets lots of light. This move-in ready elegant home has an open floor plan which is designed for entertaining. This home has maintained all the vintage details: built in book cases,

    Agent Photo

    Shirley Walker

    Berkshire Hathaway HomeServices Chicago

    (872) 312-2609

    4942 S Ellis Ave, Chicago, IL 60615
  • /78

    $3,100,000

    • 7 Beds
    • 6.5 Baths
    • 7,000 Sq Ft

    5235 S University Ave, Chicago, IL 60615

    Stunning and impressive Hyde Park home and coach house designed by architect, James Gamble Rogers, is a short walking distance to The University of Chicago campus and hospital. This Collegiate Gothic architecture is similar to The University of Chicago impressive Gothic buildings. This home is filled with original classical architectural details and is tastefully updated to fit today's modern

    Agent Photo

    Shirley Walker

    Berkshire Hathaway HomeServices Chicago

    (872) 278-4641

    5235 S University Ave, Chicago, IL 60615
  • /23

    $229,000

    • 3 Beds
    • 1 Bath

    4842 S Wallace St, Chicago, IL 60609

    Endless possibilities await in this charming 3-bedroom, 1-bath ranch home nestled in the heart of Canaryville. Whether you're an investor, savvy DIYer, or a homeowner ready to bring your vision to life, this property offers great bones and a solid foundation to build on. Inside, you'll find a functional layout full of potential, while outside, a spacious yard with a deck provides the perfect

    Stefanie D'Agostino Redfin Corporation

    4842 S Wallace St, Chicago, IL 60609
  • /42

    $595,000

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

    4914 S Washington Park Ct, Chicago, IL 60615

    Completely rehabbed in 2018, this beautifully updated 4BD/3.5BA Greystone blends historic charm with modern upgrades. Original woodwork and early 1900s architecture are preserved alongside a stylish kitchen (updated 2021) and sleek bathrooms (primary en-suite updated 2022). Main level features spacious living room, formal dining with dry bar, modern kitchen, and family room. Upstairs offers 3

    Stefanie D'Agostino Redfin Corporation

    4914 S Washington Park Ct, Chicago, IL 60615
  • /38

    $615,000

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

    4637 S Michigan Ave, Chicago, IL 60653

    Welcome to this beautifully crafted 5-bedroom, 3.5-bath home built in 2019 and set on an impressive 160-foot deep lot. With a spacious 2-car garage and an expansive backyard, this property seamlessly blends luxury and functionality. Inside, you'll find custom kitchen cabinetry, a large quartz island, designer backsplash, and rich solid oak hardwood flooring. Detailed millwork and wainscoting add

    Stefanie D'Agostino Redfin Corporation

    4637 S Michigan Ave, Chicago, IL 60653
  • /39

    $1,149,000 New Construction

    • 5 Beds
    • 3.5 Baths
    • 3,900 Sq Ft

    3300 S Giles Ave, Chicago, IL 60616

    Spectacular, Custom and Ultra Upgraded New Home right here in Chicago's Premier Gap Neighborhood. Move In Ready All Brick Home at 3300 S. Giles pulls out all the stops. Walk in and you'll be greeted with Red Oak flooring throughout the home, Sun drenched living room with electric fireplace. Walk through to the Amazing Custom Chef's Kitchen complete with a Quartz book matched waterfall island with

    Michael Giliano Compass

    3300 S Giles Ave, Chicago, IL 60616
  • /26

    $815,000

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

    1015 E 43rd St, Chicago, IL 60653

    Welcome home to this stunning newer masonry 4BD/3.5BA luxury home, featuring top-tier craftsmanship and high-end finishes throughout. Enjoy a custom gourmet kitchen with quartz countertops, island, and premium SS appliances. Wide-plank hardwood floors, large windows, and custom millwork create a bright, modern feel with lots of natural light. The spacious primary suite offers a spa bath, jumbo

    Joanna Olszynska Compass

    1015 E 43rd St, Chicago, IL 60653
  • /42

    $739,900

    • 4 Beds
    • 3.5 Baths
    • 2,940 Sq Ft

    334 E Pershing Rd, Chicago, IL 60653

    Step into a home that feels like it was designed just for you-where modern luxury meets everyday ease in a quiet, gated enclave in the heart of Bronzeville. This 4-bedroom, 3.1-bath residence at The Collection on the Drive welcomes you with soaring 14-foot ceilings and tilt-and-turn windows that flood the living room with natural light. The open layout is refined yet connected, anchored by a

    Jennifer Bell Fulton Grace Realty

    334 E Pershing Rd, Chicago, IL 60653
  • /43

    $850,000 Open Sat 11AM - 1PM

    • 5 Beds
    • 4.5 Baths
    • 4,400 Sq Ft

    4243 S King Dr, Chicago, IL 60653

    This stunning historic Greystone, located in the heart of Bronzeville on iconic King Drive, seamlessly blends timeless Chicago architecture with modern luxury. Thoughtfully renovated, the home features a spacious and airy main level designed for both everyday living and entertaining. The first floor includes a formal sitting room, dining room, living room, and a stylish kitchen-complete with

    Krystal Corley RE/MAX Premier

    4243 S King Dr, Chicago, IL 60653
  • /40

    $597,000

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

    3530 S Union Ave, Chicago, IL 60609

    Welcome to timeless charm reimagined for modern living in this recently renovated home, nestled in Bridgeport's vibrant and highly sought-after neighborhood. Completely renovated from top to bottom, this open-concept residence blends historical charm with contemporary finishes and thoughtful design throughout. As you step inside, you're greeted by a bright, open concept main floor that seamlessly

    Carol O'Malley HomeSmart Connect LLC

    3530 S Union Ave, Chicago, IL 60609
  • /23

    $907,500

    • 4 Beds
    • 3.5 Baths
    • 3,200 Sq Ft

    4110 S Vincennes Ave, Chicago, IL 60653

    Experience luxury living in the heart of Bronzeville with this stunning 5-bedroom, 3.5-bathroom home, built new in 2018 and meticulously maintained. Move-in ready, this residence boasts countless upgrades including custom paint, elegant window treatments, trey ceilings, integrated surround sound, and a fully finished garage that is insulated, has an EV charger and can double as a studio, office,

    Sheila Dantzler Jameson Sotheby's Intl Realty

    4110 S Vincennes Ave, Chicago, IL 60653
  • /2

    $799,000

    • 5 Beds
    • 5 Baths
    • 4,638 Sq Ft

    5028 S Blackstone Ave, Chicago, IL 60615

    Welcome to this stunning brick single-family home located in Chicago's architecturally rich and historic Kenwood District. Spanning an impressive 4,458 square feet, this timeless residence presents a rare opportunity-a versatile canvas for your next inspired design. Thoughtfully reimagined with a focus on both aesthetics and infrastructure, the home blends classic character with modern updates.

    Yanfei Hu Berkshire Hathaway HomeServices Chicago

    5028 S Blackstone Ave, Chicago, IL 60615
  • /38

    $1,450,000

    • 4 Beds
    • 3.5 Baths
    • 3,200 Sq Ft

    5729 S Harper Ave, Chicago, IL 60637

    A special home on Harper in move-in condition with garage parking! This thoughtfully redesigned Victorian home is perfectly situated on one of Hyde Park's most popular and charming blocks. Highly upgraded by the current owners, the resulting 5-bedroom, 3.5-bath home retains an abundance of historic vintage detail (high ceilings, hardwood floors), plus numerous modern upgrades, including central

    Robert Sullivan Berkshire Hathaway HomeServices Chicago

    5729 S Harper Ave, Chicago, IL 60637
  • /40

    $800,000

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

    4535 S Evans Ave, Chicago, IL 60653

    Welcome to 4535 S Evans, a nearly new construction home located in the beautiful and historic lakefront neighborhood of Bronzeville. Built in 2023, this modern residence offers all the benefits of new construction-without the wait. Everything in the home, from mechanicals to finishes, is less than a couple years old. Set on an extra-deep lot-over 170 feet long-this property boasts incredible

    Jen Romolo @properties Christie's International Real Estate

    4535 S Evans Ave, Chicago, IL 60653
  • /46

    $749,000

    • 4 Beds
    • 3.5 Baths
    • 4,453 Sq Ft

    3215 S Calumet Ave, Chicago, IL 60616

    Now under $750k! RARELY AVAILABLE! Welcome to Robert Roloson Row in The Gap! Featured in Crain's, this three-story estate is 1 of only 4 Roloson rowhouses that were built by the renowned architect Frank Lloyd Wright. With over 4,500 square feet of living space, this 4 bedroom 3.1 bathroom home has a main level reception room that can be used to a home office, the second level includes a formal

    Vergis Eiland @properties Christie's International Real Estate

    3215 S Calumet Ave, Chicago, IL 60616
  • /19

    $690,000

    • 4 Beds
    • 4 Baths
    • 2,980 Sq Ft

    4456 S Berkeley Ave, Chicago, IL 60653

    Beautiful Graystone in the heart of N Kenwood. This spacious 3 story above ground home, in addition to a finished basement, has been kept and maintained extremely well. 5 Bedroom, and 4 Full baths. Coffered ceiling, wainscoting,and track lighting on the first floor. Gourmet kitchen has Honey Maple cabinets, Stainless Steel Appliances. Breakfast bar. A separate cozy Family Room. Luxurious 3rd

    Talat Arain Coldwell Banker Realty

    4456 S Berkeley Ave, Chicago, IL 60653
  • /38

    $725,000

    • 3 Beds
    • 3.5 Baths

    3125 S Giles Ave, Chicago, IL 60616

    Chic 4BR/3.1BA modern Bronzeville rowhouse! 2-car detached garage with a yard. Everything in the house is 5 years new including windows, roof, millwork, doors, HVAC, electrical, plumbing, floors, kitchen, baths and deck. Chef's kitchen features Bosch professional stainless-steel appliances with vented hood and wine cooler. Beautiful cabinetry with cascade quartz counters and glass tile

    Ken Jungwirth @properties Christie's International Real Estate

    3125 S Giles Ave, Chicago, IL 60616
  • /62

    $975,000

    • 5 Beds
    • 4.5 Baths
    • 3,852 Sq Ft

    4553 S Ellis Ave, Chicago, IL 60653

    Timeless Elegance Meets Modern Luxury in This Stately Greystone Nestled on a prime block in one of Chicago's most coveted neighborhoods, this stately Greystone-built in 1892-seamlessly blends timeless architectural detail with refined modern updates. From the moment you step into the grand entry gallery, you're greeted by a sweeping staircase and an abundance of natural light, setting the tone

    Anthony Rouches @properties Christie's International Real Estate

    4553 S Ellis Ave, Chicago, IL 60653
  • /19

    $579,000

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

    5555 S Harper Ave, Chicago, IL 60637

    On the market for the first time in many years, this charming 4-bedroom, 2 full-bath "E" townhouse is located on a quiet street in the University of Chicago campus neighborhood. Designed by I.M. Pei in the early 1960s, it features a wonderfully laid out open floor plan on three above-grade levels and is in excellent condition, freshly painted throughout and with upgraded baths and kitchen

    Robert Sullivan Berkshire Hathaway HomeServices Chicago

    5555 S Harper Ave, Chicago, IL 60637
  • /41

    $999,500

    • 4 Beds
    • 3.5 Baths
    • 3,000 Sq Ft

    1920 S Shelby Ct, Chicago, IL 60608

    Truly One-of-a-Kind! From the moment you arrive, you'll know this home is something special. The bold, modern exterior and custom steel details set the tone for what's inside - a masterfully designed space that blends contemporary style with warm, natural elements. The open-concept main level features a stunning chef's kitchen surrounded by metal, wood, and stone, flooded with natural light and

    Konstantin Shelegeda Inter Properties Inc

    1920 S Shelby Ct, Chicago, IL 60608
  • /44

    $575,000

    • 3 Beds
    • 3.5 Baths
    • 2,900 Sq Ft

    4409 S Prairie Ave, Chicago, IL 60653

    Nestled on the historic and extra-wide Prairie Avenue, this stunning 4-bedroom, 3.5-bath residence offers a thoughtfully designed layout that perfectly blends comfort, style, and versatility. The expansive second level features three generously sized bedrooms, including a serene primary suite, along with a dedicated laundry room for added convenience. The sun-drenched main floor is made for

    Irina Ko Sky High Real Estate Inc.

    4409 S Prairie Ave, Chicago, IL 60653
  • /22

    $697,000 Open Sat 1PM - 3PM

    • 4 Beds
    • 3.5 Baths
    • 2,700 Sq Ft

    4752 S Champlain Ave, Chicago, IL 60615

    Bronzeville. If all "new" is what you desire, look no further. You will enjoy living in this exquisitely redone expansive limestone home, all new with all the finishes and layout features you desire on one of the most desireable and quaint tree-lined streets of Grand Boulevard. Wonderfully styled, this sumptuously large four-bedroom and three-and-a-half-bath home is impressive from the moment you

    Naja Morris @properties Christie's International Real Estate

    4752 S Champlain Ave, Chicago, IL 60615
  • /27

    $750,000

    • 3 Beds
    • 3.5 Baths
    • 4,177 Sq Ft

    4342 S Forrestville Ave, Chicago, IL 60653

    Welcome to 4342 S Forrestville Avenue - A Perfect Blend of Historic Charm and Modern Luxury. Located on a quiet, tree-lined street in the heart of Bronzeville's coveted Oakland neighborhood, this beautifully renovated 4-bedroom, 3.5-bath gated Greystone offers an impressive 4,177 sq. ft of thoughtfully designed living space. The home seamlessly combines timeless architecture with

    Tiffany White @properties Christie's International Real Estate

    4342 S Forrestville Ave, Chicago, IL 60653
  • /19

    $549,900

    • 2 Beds
    • 2 Baths
    • 1,900 Sq Ft

    1816 S Jefferson St, Chicago, IL 60616

    2 lots with 1 single family house and a coach house on one lot. Has renters in both houses. Second lot could park up 14 cars in vacant lot. Could keep renters in one lot and build new homes in vacant lot. Great investment!

    Mona Jee RE/MAX Premier

    1816 S Jefferson St, Chicago, IL 60616
  • /28

    $675,000

    • 5 Beds
    • 4 Baths
    • 3,330 Sq Ft

    4631 S Evans Ave, Chicago, IL 60653

    Welcome to this beautifully renovated 5-bedroom, 4-bathroom single-family home located in the heart of vibrant Bronzeville. This spacious residence has been completely transformed with modern finishes, offering three full levels of luxurious living and an open-concept design perfect for both everyday living and entertaining. The main level features a show-stopping open kitchen with high-end

    Anthony Florentino eXp Realty

    4631 S Evans Ave, Chicago, IL 60653
  • /41

    $675,000

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

    4114 S King Dr, Chicago, IL 60653

    Step into the epitome of modern elegance with this fully renovated, two-story Greystone with views of beautiful King Drive in historic Bronzeville. This generously-proportioned home with an open floor plan is a modern dream for living & entertaining, w/a seamless flow between the main rooms. Entertain guests in the spacious traditional living room, with beautifully crafted details including 11

    Samara Morris Real People Realty

    4114 S King Dr, Chicago, IL 60653
  • /45

    $675,000

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

    4540 S Prairie Ave, Chicago, IL 60653

    This historic Bronzeville Redstone Mansion, rehab 2020, 4500 sw. ft. offers 5 bedrooms on the 2nd level 2.5 baths, newer kitchen with breakfast bar & spacious island, granite counter tops, all stainless steel appliances stay, newer windows, roof, 2 furnaces, 2 a/c units, hardwood floors thru-out, 3 wood burning fireplaces in Living room, Family room & Master bedroom. Enclosed sunroom, deck.

    Mireya Rogoz-Bedore RE/MAX 10

    4540 S Prairie Ave, Chicago, IL 60653
  • /55

    $674,900

    • 4 Beds
    • 6 Baths
    • 3,900 Sq Ft

    4364 S Oakenwald Ave, Chicago, IL 60653

    Welcome to The Oakenwald Estate! Stately 4 bedroom 4.2 bathroom 3,900 square foot 3-story home situated on a double lot in the heart of Kenwood Historic District! This home features an open floor plan on the main level, plenty of natural lighting, a formal living room and dining room, solid vintage oak detail, hardwood floors, an eat-in kitchen with island, custom cabinets and marble countertops

    Vergis Eiland @properties Christie's International Real Estate

    4364 S Oakenwald Ave, Chicago, IL 60653
  • /27

    $549,900

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

    430 E 46th St, Chicago, IL 60653

    This stunning attached single-family Bronzeville Beauty is a rare find. Recently rehabbed and boasting a classic Greystone exterior with a fenced backyard and new parking pad, this property seamlessly blends historic charm with contemporary elegance. Inside, you'll find a spacious main level perfect to accommodate family and friends alike. The 5 generous sized bedrooms are housed on the second

    Perdure Carter Realty of America, LLC

    430 E 46th St, Chicago, IL 60653
  • /7

    $269,000

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

    5217 S Green St, Chicago, IL 60609

    BRICK SINGLE FAMILY, IN VERY NICE CONDITION that features open concept BIG AND OPEN BASEMENT, NEW KITCHEN , NEW BATH BEAUTIFUL FLOORS, EASY TO SHOW, LOW TAXES.

    Juan Loza American International Realty

    5217 S Green St, Chicago, IL 60609
  • /12

    $66,900

    • 5 Beds
    • 2 Baths
    • 1,350 Sq Ft

    5747 S La Salle St, Chicago, IL 60621

    Large single family home sold as-is. Five bedrooms, two bathrooms. House needs work. No survey provided.

    David Williamson Choice Realty Group Inc.

    5747 S La Salle St, Chicago, IL 60621
  • /23

    $2,289,000

    • 5 Beds
    • 3.5 Baths
    • 4,550 Sq Ft

    925 E 49th St, Chicago, IL 60615

    Luxury Living in the Kenwood Historic District - Award-Winning Design, Massive Yard! Nestled in the heart of the prestigious Kenwood Historic District, this luxurious residence is a true architectural gem, boasting a massive, beautifully landscaped yard that spans nearly half the length of a football field. Designed by award-winning architect, Anthony Akindele in 1999, this home blends

    Sheila Dantzler Jameson Sotheby's Intl Realty

    925 E 49th St, Chicago, IL 60615
  • /37

    $424,900

    • 6 Beds
    • 3 Baths
    • 1,584 Sq Ft

    3722 S Wabash Ave, Chicago, IL 60653

    Rare single-family home in the heart of historic Bronzeville, one of the fastest growing neighborhoods in the city! Freshly-painted and full of potential, this renovated six bedroom, three bathroom home is bright, spacious, and ready for a two-unit conversion or multi-generational living. The main level features oak hardwood floors, four bedrooms, two full baths, a formal living and dining room,

    Jerome Harper Keller Williams ONEChicago

    3722 S Wabash Ave, Chicago, IL 60653
  • /2

    $224,900

    • 4 Beds
    • 2 Baths
    • 2,410 Sq Ft

    4917 S Washington Park Ct, Chicago, IL 60615

    Amazing Opportunity on Historic Washington Park Court! Unlock the potential of this charming single-family home nestled on one of the city's most iconic blocks. Bursting with character, this property features original woodwork, hardwood floors, 4-bedrooms, 2-bathrooms and a 2-car brick garage. Bring your vision and transform this timeless beauty into a stunning showpiece. A rare chance to invest

    Shawnda Morris TADD Realty

    4917 S Washington Park Ct, Chicago, IL 60615
  • /24

    $199,900

    • 2 Beds
    • 1.5 Baths
    • 1,141 Sq Ft

    5308 S Peoria St, Chicago, IL 60609

    "Welcome to this renovated single-family home offering the perfect blend of modern updates and everyday comfort. Featuring 2 bedrooms on the main floor, 1 bedroom in the basement and 1.5 bathrooms throughout. When outside, enjoy your brand-new front and rear porches - perfect for morning coffee or evening gatherings. The home also features a 2-car garage, along with 2 additional exterior

    Antonio Rubio eXp Realty

    5308 S Peoria St, Chicago, IL 60609
  • /24

    $479,000

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

    4444 S Berkeley Ave, Chicago, IL 60653

    Great opportunity to live on Berkeley Ave. One of the most lovely historic streets in North Kenwood conveniently located with just blocks to the lake, Du Sable LSD & interstate. The property has been updated over the years however still maintains many of the original details through out the home. The original glass front door welcomes you in where you will be captured by all the wonderful vintage

    Anna Foley-Henry Dream Town Real Estate

    4444 S Berkeley Ave, Chicago, IL 60653
  • /24

    $369,900

    • 3 Beds
    • 1.5 Baths
    • 1,184 Sq Ft

    1703 S Ruble St, Chicago, IL 60616

    Charming 2-Story Home in the Heart of Pilsen - Move-In Ready! Don't miss this beautifully maintained 2-story home located on a quiet street in Chicago's vibrant Pilsen neighborhood! This spacious property features 3 bedrooms, 2 bathrooms, and a warm, open-concept living area filled with natural light. The inviting living room boasts hardwood floors, recessed lighting, and a large bay window.

    Victor Ti RE/MAX Premier

    1703 S Ruble St, Chicago, IL 60616
  • /29

    $530,000

    • 3 Beds
    • 3 Baths

    4805 S Langley Ave, Chicago, IL 60615

    Incredibly Opportunity to Acquire Classic Greystone in Historic Bronzeville Location! Fully Remodeled in 2017 (Bathrooms remolded 2020) with a Blend of Vintage and Modern Finishes Throughout. Top Floor Includes 3 Bedrooms and 2 Bathrooms. Spacious Primary Suite with Double Vanity and Stand Up Shower. Main Level Includes High Ceilings w/ Inviting Open Layout Connecting the Formal Living Room and

    Rafael Nivar North Clybourn Group, Inc.

    4805 S Langley Ave, Chicago, IL 60615
  • /36

    $1,100,000

    • 4 Beds
    • 3.5 Baths
    • 3,200 Sq Ft

    1344 E Madison Park, Chicago, IL 60615

    The historic greystone homes that line the north side of the highly desirable Madison Park community are truly special and seldom come on the market. The listing of this stately property therefore represents a rare opportunity for a discerning buyer seeking a gracious 4-bedroom, 3.5-bath home with garage parking in that very special location. The rooms are all spacious and retain many original

    Robert Sullivan Berkshire Hathaway HomeServices Chicago

    1344 E Madison Park, Chicago, IL 60615
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