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Explore Similar Apartments Within 2 Miles of Jackson Park Highlands, IL

  • /60

    $1,674,900

    • 8 Beds
    • 6 Baths

    6909 S Chappel Ave, Chicago, IL 60649

    Designed by the famous Chicago architect Edward G McClellan in 1925. Mr McClellan left his artistic imprint on this unique one of a kind property. This architectural marvel combines 17th century English Gothic Revival design with 20th century opulence and 21st century modern convenience and amenities. When you add it all up, you have 100 PERCENT luxury and a true one of a kind property. You will

    Agent Photo

    John Wright

    Keller Williams Premiere Properties

    (312) 516-4314

    6909 S Chappel Ave, Chicago, IL 60649
  • /31

    $689,000

    • 11 Beds
    • 5 Baths

    5943 S Indiana Ave, Chicago, IL 60637

    ENORMOUS PRICE REDUCTION !! Timeless Greystone 3 flat building is now available for you in RED HOT Washington Park neighborhood of Chicago. As the owner, you have the flexibility of living in the top floor unit while collecting stable market rents from the tenants on first and second floor, or rent the top floor unit and max out your income!!! Hardwood floors THROUGHOUT each unit. First floor

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    John Wright

    Keller Williams Premiere Properties

    (312) 997-5039

    5943 S Indiana Ave, Chicago, IL 60637
  • /2

    $549,900

    5612 S King Dr, Chicago, IL 60637

    9+ Cap Rate in Woodlawn Neighborhood across the street from Washington Park and the Park District! Multi Unit building owned by sellers for almost 70 years. Invest in your future! Real estate!

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    Kimberly Chase-Harding

    Berkshire Hathaway HomeServices Chicago

    (312) 820-9459

    5612 S King Dr, Chicago, IL 60637
  • /25

    $599,900

    • 12 Beds
    • 4 Baths

    5942 S Calumet Ave, Chicago, IL 60637

    Great Investment Opportunity For Owner Occupant with the potential to live rent free Or Investor looking for a great return on their investment. Fully occupied 3 unit Greystone. Each unit has 4 beds 1 bath and separate utilities. NEW Electrical throughout the building. Water tanks were recently updated for each unit. New Intercom system has been added to the building for your convenience.

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    O'Neia Washington

    O W Auction Group LLC

    (312) 626-8858

    5942 S Calumet Ave, Chicago, IL 60637
  • /2

    $235,000

    • 7 Beds
    • 2 Baths

    7220 S Rhodes Ave, Chicago, IL 60619

    Welcome to 7220 S Rhodes Ave! What an incredible space and layout in this legal 2-unit with 8 total bedrooms and 3 full baths, including a finished basement with a non-conforming 1-bed apartment. Unit 1: 3BR/1BA | Unit 2: 4BR/1BA | Basement: 1BR/1BA. Detached 2.5-car garage, large yard, and strong rent potential. This property provides a great opportunity for house hacking or cash-flow-focused

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    Reginald Patterson

    eXp Realty

    (773) 639-2139

    7220 S Rhodes Ave, Chicago, IL 60619
  • /14

    $394,900 Pre-Foreclosure

    • 6 Beds
    • 2 Baths

    6621 S Marquette Dr, Chicago, IL 60637

    Renovated Two-Unit Greystone in West Woodlawn! This classic Chicago Greystone features two spacious 3 bed, 1 bath units, each updated with hardwood floors, stainless steel appliances, countertops, and modern finishes. Renovated in 2024 before the current tenants moved in. Underground plumbing replaced and updated in 2023 from the building to street. The unfinished basement offers potential for a

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    Devin Burks

    @properties Christie's International Real Estate

    (312) 815-2038

    6621 S Marquette Dr, Chicago, IL 60637
  • /35

    $175,000

    • 5 Beds
    • 2 Baths

    7930 S Luella Ave, Chicago, IL 60617

    SHORTSALE Opportunity. Not finding what you are looking for in a multi unit? Bring your creative ideas for this diamond in the rough. Building does need work which is reflected in the list price. This Multiunit features enclosed front and back porches, tall ceilings, spacious rooms and floor plan. Great Investment Opportunity For Owner Occupant with the potential to live rent free Or Investor

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    O'Neia Washington

    O W Auction Group LLC

    (773) 974-8432

    7930 S Luella Ave, Chicago, IL 60617
  • /17

    $175,000

    • 7 Beds
    • 3 Baths

    6716 S Indiana Ave, Chicago, IL 60637

    Investor Opportunity - 2-Unit Building with Duplex-Down Layout Don't miss this excellent opportunity to own a partially renovated 2-unit building with strong rental or resale potential. Some work has already been started, and now it's ready for the right buyer to complete the vision. The first-floor unit is a spacious duplex-down, featuring four bedrooms and two full bathrooms. The main level

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    Kristen Roussev

    Village Realty, Inc.

    (312) 584-9396

    6716 S Indiana Ave, Chicago, IL 60637
  • /14

    $325,000

    • 5 Beds
    • 2 Baths

    6510 S Rhodes Ave, Chicago, IL 60637

    Turnkey Greystone with Additional Lot - Prime West Woodlawn Investment Discover a rare opportunity to own a beautifully kept two-unit Greystone with endless income potential in the fast-growing West Woodlawn community. Ideally located near the University of Chicago, this property offers convenience, stability, and growth for seasoned investors and first-time buyers alike. The first-floor

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    Kristen Roussev

    Village Realty, Inc.

    (773) 917-0332

    6510 S Rhodes Ave, Chicago, IL 60637
  • /30

    $194,900

    • 5 Beds
    • 2 Baths

    3011 E 80th St, Chicago, IL 60617

    Classic multi-family home offering a total of five bedrooms and two bathrooms across 2,000 square feet of living space. This property exudes timeless charm while featuring hardwood floors and a spacious living room. Recent updates include a new hot water heater, faucet replacements, and bathroom re-caulking, ensuring the home is move-in ready. With built-in laundry facilities and a history of

    Jaime Birks eXp Realty

    3011 E 80th St, Chicago, IL 60617
  • /35

    $275,000

    • 7 Beds
    • 2 Baths

    8348 S Saginaw Ave, Chicago, IL 60617

    Great investment opportunity with this multi-unit property! This property has 2 legal units and an additional 2 non-conforming units that provide endless opportunities. All 4 units have been updated in the last 5 years and feature vinyl plank flooring throughout. Unit 1 & 2 both have 2 bedrooms, a full bath, spacious living rooms and great sized kitchens. Parking pad in the rear of the home.

    Cesar Juarez Redfin Corporation

    8348 S Saginaw Ave, Chicago, IL 60617
  • /14

    $829,000

    • 9 Beds
    • 6 Baths

    6349 S Maryland Ave, Chicago, IL 60637

    Set in exceptionally well-located Woodlawn on the confluence of Hyde Park walking distance to University of Chicago Campus. Built New 2022 Developer Owned and Operated. Expansive footprint, 3 flats all 3 bedroom 2 baths Exceptional Elegance, Intelligent Design, Professional Fully Appointed Kitchen Cabinetry, Integrated Appliances, Quartz Island Engineered floors, Fireplace, Curated Gallery of

    Karen Biazar North Clybourn Group, Inc.

    6349 S Maryland Ave, Chicago, IL 60637
  • /47

    $495,000

    • 9 Beds
    • 3 Baths

    6605 S Maryland Ave, Chicago, IL 60637

    Fully Rehabbed 2-Unit in Prime East Woodlawn! Welcome to this spacious two-unit building in East Woodlawn, near the University of Chicago and the Obama Presidential Center. Tons of new construction on Maryland Ave. The property has 9 bedrooms and 3 bathrooms, offering great living space and rental potential. Each unit has separate utilities. While there's no central air, both units have HVAC

    Phillip Younan Fulton Grace Realty

    6605 S Maryland Ave, Chicago, IL 60637
  • /11

    $315,000

    • 5,736 Sq Ft

    1526 E 72nd Place, Chicago, IL 60619

    Maximize your ROI with this exceptional middle-income rental development opportunity! This solid Chicago brick building, complete with balconies, is strategically located in a transit-connected hub, blocks from Metra, Jackson Park, and the Obama Library site, and just a stone's throw from the lakefront. Though in need of a full rehab, the payoff is immense. Currently set up as six 2 Bed/1 Bath

    Derek Walvoord Exit Strategy Realty / EMA Management

    1526 E 72nd Place, Chicago, IL 60619
  • /50

    $625,000

    7831 S Colfax Ave, Chicago, IL 60649

    Stunning 8-Unit Gem in South Shore! Just a few blocks from beautiful Lake Michigan, this fully occupied 8-unit building offers an incredible opportunity in one of Chicago's most vibrant neighborhoods. Featuring all-new electric, plumbing, and HVAC, plus a newer roof with skylight and two brand-new rear porches. All city violations have been cleared and title is clean.Each unit showcases spacious

    Damaris Santiago Manage Chicago, Inc.

    7831 S Colfax Ave, Chicago, IL 60649
  • /22

    $249,000

    • 8 Beds
    • 3 Baths

    8253 S Brandon Ave, Chicago, IL 60617

    Solid income producing potential! Currently set up as 3 Units, this building offers a competitive cap rate, making it a great opportunity for an owner occupant or a smart investor. Units 1F & 1R offer 2BR/1BA each, with an open floorplan and hardwood floors. Kitchen and baths feature tasteful espresso cabinets, granite counters, and tile finishes. Unit 2 is a huge 4BR/1BA apartment that occupies

    Andria Hernandez Compass

    8253 S Brandon Ave, Chicago, IL 60617
  • /17

    $350,000

    • 4 Beds
    • 4 Baths

    8150 S Clyde Ave, Chicago, IL 60617

    Outstanding income-producing opportunity 4-unit building. Most units feature hardwood flooring. Each apartment offers 1 bedroom plus a sunroom-often used as a second bedroom; adding a closet may convert it to a true 2BR. Consistent, renter-friendly layout with generously sized bedrooms, a spacious living room, and a separate dining room. Amenities include a massive fenced backyard and a solid

    Karmen Spears POWER Realty Chicagoland,PLLC

    8150 S Clyde Ave, Chicago, IL 60617
  • /22

    $7,000,000

    • 40,000 Sq Ft

    Unlisted Address

    Pleased to present the multifamily property at 7270 S. South Shore Dr. This asset represents a compelling investment opportunity in a vibrant community. The subject property is a 53-unit multifamily elevator building with a rooftop venue located in the heart of Chicago's tree-lined South Shore neighborhood. It is conveniently situated fifteen minutes from the Loop and one block from the

    Travis Montgomery Keller Williams ONEChicago

    Unlisted Address
  • /10

    $270,000

    • 6 Beds
    • 5 Baths

    6911 S Jeffery Blvd, Chicago, IL 60649

    Solid Brick 2-Flat with great potential! Each spacious unit offers 3 bedrooms and 2 full bathrooms, providing plenty of room for comfortable living. The property also features a full basement with an additional bathroom, offering extra living or storage options. A 2-car brick detached garage adds value and convenience. While the property needs some TLC, it has good bones and is a fantastic

    Kason Wallace Premier Midwest Realty, INC

    6911 S Jeffery Blvd, Chicago, IL 60649
  • /49

    $295,000

    • 5 Beds
    • 3 Baths

    8210 S Manistee Ave, Chicago, IL 60617

    Nestled on a generous 48' x 124' lot, this versatile 2-family property offers an exceptional opportunity for homeowners and investors alike. With a spacious layout, classic features, and modern conveniences, this property is a must-see! Brand new siding throughout. Unit 1: This expansive unit is duplexed to the basement, offering 4 bedrooms and 2 bathrooms. The main level boasts beautiful

    Crystal Smith, REALTORĀ® Illinois Real Estate Partners

    8210 S Manistee Ave, Chicago, IL 60617
  • /16

    $655,000

    7931 S Manistee Ave, Chicago, IL 60617

    Located in the South Chicago neighborhood, the building has 7-units, all consisting of 3 bedrooms and 1 bathroom. The backyard is fully fenced, with 4 parking spaces available if new owner wants to open the fence. The building has been well maintained over the last 6 years of ownership, setting things up like two washers and dryers and storage units for all apartments in the basement, as well as

    Peter Deja Cross County Realty Inc.

    7931 S Manistee Ave, Chicago, IL 60617
  • /60

    $745,000

    • 8 Beds
    • 3 Baths

    6347 S Drexel Ave, Chicago, IL 60637

    $15,000 seller credit and a low interest rate! A Greystone rebuilt with permits in vibrant Woodlawn. This 2023 gut-rehab blends historic elegance with modern upgrades. Potential rental income of up to $6,000/month. With the seller's credits you can reduce your mortgage payment to around $4,000, offering up to a potential $2,000 in monthly profit. The property features tall ceilings, hardwood

    Phillip Dixon Compass

    6347 S Drexel Ave, Chicago, IL 60637
  • /25

    $559,000

    • 7 Beds
    • 3 Baths

    6336 S Eberhart Ave, Chicago, IL 60637

    GREAT WOODLAWN INVESTMENT OPPORTUNITY, NEW CONTRUCTION ALL AROUND, INCLUDES A NEW MULTI MILLION DOLLAR COMMUNITY CENTER JUST FOOTSTEPS AWAY. OBAMA LIBRARY NEARBY. Welcome to 6336 S Eberhart, a stunning newly rehabbed two-unit property that has been thoughtfully renovated from top to bottom. The spacious lower unit is duplexed into the basement, offering a generous layout with 4 bedrooms and 2

    Johnathan Clancy Keller Williams Premiere Properties

    6336 S Eberhart Ave, Chicago, IL 60637
  • /35

    $269,900

    • 8 Beds
    • 3 Baths

    7836 S Constance Ave, Chicago, IL 60649

    *Multiple Offers Received. Highest and Best due by 9-11-25.* Gain instant sweat-equity with this classic brick 3-unit in the Auburn Gresham. This property offers two 3-bed, 1-bath units featuring and one 2-bed, 1-bath: sun-filled living rooms with decorative fireplaces; formal dining rooms; large kitchens with shaker cabinets, quartz counts, stainless appliances and loads of storage; stylish

    Anthony Disano Parkvue Realty Corporation

    7836 S Constance Ave, Chicago, IL 60649
  • /18

    $349,900

    • 6 Beds
    • 3 Baths

    8048 S Champlain Ave, Chicago, IL 60619

    Your next investment just arrived. Great 3 brick 3 flat brownstone ready for its next owner. 1st and 3rd floor have been renovated. New paint, new windows, new trim, updated kitchen and bathrooms. 2nd floor tenant month to month. Each unit is 2 bed 1 bath. Each floor has an amazing wood deck in the back for relaxing. An amazing deal, with still room to add some sweat equity! 3 car garage in the

    Mark Rantis Keller Williams Success Realty

    8048 S Champlain Ave, Chicago, IL 60619
  • /39

    $699,900

    • 8 Beds
    • 7 Baths

    6527 S Drexel Ave, Chicago, IL 60637

    Beautiful 3 unit building, in the heart of Woodlawn. (2) 2bd/2bth and (1) DUPLEX with 4bd/3bth. Completed in 2008, this building has been well maintained. New decks installed 2022, primed and re-painted 2025, tuck pointed and sealed 2025, new stairwell carpet and paint 2025, New water heaters in each unit and more! Full list of improvements available. Premier block in Woodlawn, minutes from

    Jaki Harding Berkshire Hathaway HomeServices Starck Real Estate

    6527 S Drexel Ave, Chicago, IL 60637
  • /15

    $285,000

    • 6 Beds
    • 2 Baths

    8329 S Burnham Ave, Chicago, IL 60617

    Solid South Chicago 2-Flat Spacious bedrooms + eat-in kitchens big enough for a dining table! Super dry basement w/ coin laundry & tenant storage, plus enclosed back porch for totes/holiday decor. CHA voucher tenants in place (both planning to move), with rents currently low-huge upside for an investor ready to raise them! Systems serviced this year + roof in great shape. Off-street parking pad

    chequita dobson Coldwell Banker Realty

    8329 S Burnham Ave, Chicago, IL 60617
  • /17

    $350,000

    • 5 Beds
    • 3 Baths

    6547 S Drexel Ave, Chicago, IL 60637

    Stunning Woodlawn Greystone - Steps from the University of Chicago! This classic 2-flat blends historic charm with incredible potential. Featuring a spacious layout, fenced backyard, and a solid brick 2-car garage, it's ideal for both living and investment. The first floor is already set up as a single unit, with renovations underway to duplex down-opening the door to a 4-bed, 2-bath dream

    Keona Robinson Real People Realty

    6547 S Drexel Ave, Chicago, IL 60637
  • /14

    $365,000

    • 7 Beds
    • 3 Baths

    7100 S Prairie Ave, Chicago, IL 60619

    Great "live in" investment opportunity! This sturdy structured 2unit, features a duplex down from the 1st floor to the basement. The duplex unit has 4beds 2baths and the 2nd floor unit has 3beds 1bath. Located 3 blocks from the express way and surrounded by public transportation.

    Perdure Carter Realty of America, LLC

    7100 S Prairie Ave, Chicago, IL 60619
  • /10

    $298,000

    • 8 Beds
    • 3 Baths

    7514 S Dante Ave, Chicago, IL 60619

    Discover this updated 2023 multi-unit property that blends style, convenience, and income potential. Featuring beautiful hardwood floors throughout, this building offers two tenant-occupied units for immediate rental income, while the 1st floor unit will be delivered vacant prior to closing making this ideal for an owner-occupant. Located in a prime area near a new clinic, shopping, and

    Tom Sweeney Baird & Warner

    7514 S Dante Ave, Chicago, IL 60619
  • /55

    $420,000

    • 9 Beds
    • 6 Baths

    7825 S Phillips Ave, Chicago, IL 60649

    Welcome to 7825 S Phillips Ave in the revitalized South Shore neighborhood- a prime choice for investors or buyers seeking both lifestyle and income potential. This property is a legal 3-flat, with each spacious unit offering 3 bedrooms and 2 baths. The property's updates include newer windows. A full spacious basement, with a 3-car garage with a driveway which provides secure parking- a rare

    Sergio Hernandez Coldwell Banker Realty

    7825 S Phillips Ave, Chicago, IL 60649
  • /12

    $530,000

    • 6 Beds
    • 3 Baths

    6843 S Cornell Ave, Chicago, IL 60649

    Looking to become a homeowner and an investor at the same time? This classic brick three-flat in Chicago's red-hot South Shore neighborhood is your chance to live for less while your investment grows. Live and Invest in a Prime South Shore Location. Just steps from the beautiful Jackson Park Golf Course, the harbor, and the lakefront, this property puts you right in the heart of everything.

    Wayne Beals Exit Strategy Realty / EMA Management

    6843 S Cornell Ave, Chicago, IL 60649
  • /26

    $725,000

    • 8 Beds
    • 6 Baths

    6504 S Maryland Ave, Chicago, IL 60637

    Recently Renovated 3-Unit Investment Opportunity Near the Obama Presidential Center This beautifully rehabbed 3-unit building offers modern living in a prime location, just steps away from the highly anticipated Obama Presidential Library, opening in Spring 2026. Each unit has been thoughtfully updated to include a spacious master bedroom with an en-suite master bathroom, walk-in closet, and

    Brandon Williams Forward Realty

    6504 S Maryland Ave, Chicago, IL 60637
  • /16

    $310,000

    • 6 Beds
    • 3 Baths

    8423 S Muskegon Ave, Chicago, IL 60617

    Time to get off the sidelines!!! Recently updated two unit building located in a highly appreciating neighborhood! 6 bedrooms total with 3 baths! Top unit is a 4 bedroom 2 bath duplex-up that can make an incredible owner's unit or rental unit with high cash flow possibility! Market for a 4bed 2bath in the area ranges from $2600-$3400 according to CHA's site. The building is ready to go with newer

    Dexter Harper Coldwell Banker Realty

    8423 S Muskegon Ave, Chicago, IL 60617
  • /20

    $375,000

    • 7 Beds
    • 3 Baths

    8122 S Kingston Ave, Chicago, IL 60617

    Investor's Dream! Don't miss this opportunity to own a spacious and well-maintained 2-unit property offering immediate rental income. Both units are currently tenant-occupied, providing instant cash flow for the savvy investor. The second-floor unit features a bright and airy 3-bedroom layout filled with natural light. The first-floor unit is a modern 3-bedroom apartment with updated

    Reggie Eaton Park Place Realty Group LLC

    8122 S Kingston Ave, Chicago, IL 60617
  • /2

    $50,000

    • 7 Beds
    • 3 Baths

    8453 S Muskegon Ave, Chicago, IL 60617

    Great Opportunity For Rehabbers And Investors! This 2 Unit Building Offers A Clean Slate Ready For Redesign Or Fresh Ideas. The First Floor Unit Features 5 Bedrooms And 1.5 Baths, While The Second Floor Unit Includes 2 Bedrooms And 1 Bath.Possibilities With 7 Total Bedrooms And 2.5 Baths, This Property Has Incredible Potential For Transformation. Don't Miss Your Chance To Reimagine And Add Value!

    Toni Dortch Realty of America, LLC

    8453 S Muskegon Ave, Chicago, IL 60617
  • /2

    $200,000

    • 6 Beds
    • 2 Baths

    6620 S Rhodes Ave, Chicago, IL 60637

    Gutted, framed, rough electrical complete. Property sold as is.

    Colleen Berg Berg Properties

    6620 S Rhodes Ave, Chicago, IL 60637
  • /26

    $1,265,000

    • 7,378 Sq Ft

    6646 S Greenwood Ave, Chicago, IL 60637

    Turnkey multi-family investment opportunity in a rapidly appreciating Woodlawn location! This professionally managed six-unit building, constructed in 2007, offers exceptional cash flow from day one and significant equity growth potential. The property is designed for the savvy investor seeking a low-maintenance, stable asset with high-end appeal. Investment Highlights: Strong Cash Flow, Current

    Wayne Beals Exit Strategy Realty / EMA Management

    6646 S Greenwood Ave, Chicago, IL 60637
  • /23

    $1,460,000

    1534 E Marquette Rd, Chicago, IL 60637

    An Investor's Dream: High-Quality Multifamily Asset in Woodlawn's Growth Corridor right along the Lakefront. This professionally managed and meticulously maintained multifamily property at 1534 E Marquette Road is a premier investment opportunity in Chicago's rapidly appreciating Woodlawn community. Positioned for both immediate cash flow and substantial long-term equity growth, this asset

    Wayne Beals Exit Strategy Realty / EMA Management

    1534 E Marquette Rd, Chicago, IL 60637
  • /23

    $240,000

    • 9 Beds
    • 3 Baths

    7316 S Dante Ave, Chicago, IL 60619

    Excellent opportunity in heart of historic South Shore neighborhood. Solid brick 2-flat with spacious updated units and separate utilities. Both units feature large living rooms, separate dining rooms, kitchen with plenty of cabinets, modern baths and enclosed porches. First floor apartment has 3 bedrooms and it's duplexed to the basement with 2 extra bedrooms and additional bath. Second floor

    Grazyna Przybysz Chicago Area Realty Inc

    7316 S Dante Ave, Chicago, IL 60619

Why Live in Jackson Park Highlands

Jackson Park Highlands in Chicago is a neighborhood characterized by its quiet, elm-lined streets and well-maintained front lawns. Established in 1905, it became one of Chicago's model neighborhoods by the 1920s. The area features larger homes built in the early 20th century, including American foursquare, Colonial Revival, Tudor, and prairie styles. Strict property guidelines from the 1920s ensure spacious lots and a sense of privacy, with homes set back at least 30 feet from the property line. Located nine miles south of downtown Chicago, the neighborhood offers a peaceful retreat from the city's hustle and bustle. Residents often commute to downtown via the nearby Bryn Mawr train station. The neighborhood fosters a tight-knit community, with locals hosting social events like "flamingo Fridays."

Jackson Park Highlands is bordered to the north by Jackson Park, which offers numerous recreational activities such as soccer fields, baseball diamonds, tennis courts, and a golf course. The park also features harbors, a boat launch, and miles of paved trails, including a scenic Japanese garden. For dining options, 71st Street provides a variety of local restaurants like Slab Barbecue and Italian Fiesta Pizzeria, as well as convenient amenities such as Local Market Foods. The neighborhood's proximity to South Shore Beach and 63rd Street Beach allows residents to enjoy lakefront beaches and water activities. With crime rates lower than the national average, Jackson Park Highlands offers a safe and serene environment for its residents.

Home Trends in Jackson Park Highlands, IL

Housing Trends

Median Sale Price
$465,000
Median Single Family Sale Price
$465,000
Average Price Per Sq Ft
$157
Number of Homes for Sale
2
Last 12 months Home Sales
11
Months of Supply
2.20
Median List Price
$475,500
Median Change From 1st List Price
10%
Median Home Sale Price YoY Change
-11%
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