Jefferson Park Homes for Sale

• 

  

  

  /15

  $249,999

  • 2 Beds
  • 1 Bath

  5312 W Windsor Ave Unit 2W, Chicago, IL 60630

  Bright, move-in ready, and investor-friendly! This second-floor 2-bedroom, 1-bath condo offers desirable southern exposure, an open layout, fresh paint, and brand-new carpeting throughout. Natural light fills the spacious living room, which opens to a large private balcony-perfect for relaxing or enjoying your morning coffee. The kitchen offers plenty of cabinet space and ceramic tile flooring,

  Maureen Parrish RE/MAX Suburban

  5312 W Windsor Ave Unit 2W, Chicago, IL 60630
• Selling your home? Sell it faster and for more with a Homes.com Boost.

  Learn More
• 

  

  

  /32

  $560,000

  Pending

  • 4 Beds
  • 3 Baths
  • 1,296 Sq Ft

  5203 W Carmen Ave, Chicago, IL 60630

  Well-maintained brick home featuring 3 bedrooms and 2 full bathrooms on the main level, plus a fully finished basement with an additional bedroom and full bathroom. The main level offers hardwood flooring, a bright living area, and a functional eat-in kitchen with ample cabinet and counter space. The finished basement provides a spacious recreation/family room, recessed lighting, newly updated

  Qian Kun Chen Kale Realty

  5203 W Carmen Ave, Chicago, IL 60630
• 

  

  

  /51

  $919,000

  $10K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,213 Sq Ft

  5047 W Winnemac Ave, Chicago, IL 60630

  Welcome Home to this beautifully maintained contemporary residence, where modern design meets comfortable everyday living right on the border of Jefferson Park and Forest Glen! Thoughtfully designed for both entertaining and every day life, this super spacious home offers 4 bedrooms, 4 baths, a fully finished basement, two additional rooms and a beautifully landscaped backyard. The open-concept

  Stephanie Spenner Compass

  5047 W Winnemac Ave, Chicago, IL 60630
• 

  

  

  /14

  $399,900

  Pending

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft

  5425 N Linder Ave, Chicago, IL 60630

  Don't miss the chance to own this wonderful brick, octagon bungalow in Jefferson Park! Hardwood floors and original woodwork throughout. Eat-in kitchen with a walk in pantry. Enclosed porch with a big window overlooks the yard and serves as an entryway for your shoes and coats. Full basement great for storage has a shower enclosure and toilet. Attic was finished a long time ago and current owners

  Gary Dailey House Quest Inc

  5425 N Linder Ave, Chicago, IL 60630
• 

  

  

  /31

  $829,900

  $5K PRICE DROP

  • 8 Beds
  • 5 Baths

  5789 N Elston Ave, Chicago, IL 60646

  BEAUTIFULLY MAINTAINED NEWER BRICK 2-FLAT WITH A GARDEN APARTMENT IN THE MOST DESIRABLE NORWOOD PARK LOCATION. GREAT OPPORTUNITY FOR INVESTORS OR MULTI-FAMILY LIVING. JUST MINUTES AWAY FROM TOP-RATED SCHOOLS. FARNSWORTH ELEMENTARY SCHOOL AND TAFT HIGH SCHOOL. THE FIRST AND SECOND UNITS FEATURES 3 BEDROOMS, 1 1/2 BATHS. LARGE KITCHEN WITH A DINETTE AREA. All SEPERATE UTILITIES. NEWER WINDOWS. 2.5

  Nancy Sliwa Coldwell Banker Realty

  5789 N Elston Ave, Chicago, IL 60646
• 

  

  /26

  $679,000

  • 6 Beds
  • 2 Baths
  • 2,348 Sq Ft

  5720 N Manton Ave, Chicago, IL 60646

  Spacious historic Chicago bungalow set on an oversized lot along a beautiful tree-lined street, blending timeless architectural character with generous living space and an exceptional outdoor setting. The sun-filled main level showcases gorgeous oak hardwood floors, rich original wood trim and baseboards, an inviting living room, separate formal dining room, and a full bathroom conveniently

  Halina Latuszek K & L REALTY, INC

  5720 N Manton Ave, Chicago, IL 60646
• 

  

  /58

  $369,900

  $30K PRICE DROP

  • 4 Beds
  • 3 Baths

  5160 W Sunnyside Ave, Chicago, IL 60630

  "BACK ON THE MARKET - Buyer got cold feet. Their loss is your buyer's gain!" Bring your vision and creativity to this classic brick two-unit property offering exceptional flexibility, generous living space, and outstanding potential in one of Chicago's most desirable Northwest Side neighborhoods. Whether you envision living in one unit while generating rental income from the second, creating the

  Fernando Godoy eXp Realty

  5160 W Sunnyside Ave, Chicago, IL 60630
• 

  

  /34

  $714,900

  Pending

  • 5 Beds
  • 3.5 Baths
  • 2,866 Sq Ft

  4909 N Merrimac Ave, Chicago, IL 60630

  Extensively remodeled brick bunglalow in desirable Jefferson Park The main level features dramatic ceilings and an open floor plan. It showcases attention to detail with white oak Purezawood engineered hardwood flooring, oversized moldings, recessed can lighting, with complimenting natural light. The modern kitchen features forty two inch white shaker cabinetry, a thirty six inch custom range

  Rafal Szypcio Coldwell Banker Real Estate Group

  4909 N Merrimac Ave, Chicago, IL 60630
• 

  

  /4

  $585,000

  • 4 Beds
  • 2 Baths

  4855 N Mcvicker Ave, Chicago, IL 60630

  Opportunity awaiting! Chicago's desirable Jefferson Park, two units property with a two car garage. Unit one features two bedrooms and one bathroom, unit two also offers two bedrooms and one bath. Basement is unfinished waiting for your ideas. Property is habitable needs work and is sold AS IS.

  Martha Silveyra Re/Max Cityview

  4855 N Mcvicker Ave, Chicago, IL 60630
• 

  

  /13

  $389,000

  • 4 Beds
  • 2 Baths
  • 1,230 Sq Ft

  4921 N Moody Ave, Chicago, IL 60630

  Estate Sale .Bring your ideas and vision to this spacious 4 bedroom 2 bath house .Great opportunity for investors ,rehabber and savvy buyers looking to build instant equity .The main level with hardwood floors featuring 2 bedrooms living room ,dining room , and full bath .Second floor featuring 2 bedrooms, living room , full bath and second kitchen perfect for in law arrangement. Partially finish

  Dariusz Zelazko Landmark Realtors

  4921 N Moody Ave, Chicago, IL 60630
• 

  

  /26

  $439,000

  Pending

  • 3 Beds
  • 1.5 Baths
  • 1,288 Sq Ft

  5326 N Lockwood Ave, Chicago, IL 60630

  Must See This Gorgeous Georgian Perched On A Picturesque Tree Lined Street In Jefferson Park, This Well Loved and Well Maintained 3 Bedroom 2 Bathroom Home Boasts Hardwood Floors Throughout And Plenty Of Upgrades and Updates Including: Furnace, Roof, Windows, Water Heater, Flood System(CheckValve), Garage Door + Motor, Concrete Patio As Well As a New Powder Room in Basement. All Of This Could Not

  Teri Patient Fourth Watch Real Estate LLC

  5326 N Lockwood Ave, Chicago, IL 60630
• 

  

  /26

  $550,000

  • 6 Beds
  • 2 Baths

  5102 W Sunnyside Ave, Chicago, IL 60630

  Great opportunity to own 2-unit property located in Chicago's Portage Park neighborhood minutes from Jefferson Park and Mayfair. Both units are currently occupied with leases in place through May 2027. Tenants pay electric and gas. Interiors feature vintage character, including woodwork and built-in hutches, with spacious kitchens and formal dining rooms. The property also includes enclosed back

  Antje Gehrken A.R.E. Partners Inc.

  5102 W Sunnyside Ave, Chicago, IL 60630
• 

  

  /31

  $599,000

  Pending

  • 5 Beds
  • 3 Baths
  • 2,208 Sq Ft

  5230 N Mcvicker Ave, Chicago, IL 60630

  Nestled on a quiet, tree-lined street in one of Chicago's most established Northwest Side neighborhoods, this spacious Jefferson Park bungalow offers an impressive 2,208 square feet of living space with 5 bedrooms and 3 full bathrooms. Whether you're searching for room to grow, space to work from home, or the perfect multi-generational living arrangement, this home delivers exceptional

  Carlos Saldana Baird & Warner

  5230 N Mcvicker Ave, Chicago, IL 60630
• 

  

  /4

  $465,000

  Pending

  • 4 Beds
  • 3 Baths

  5212 N Ludlam Ave, Chicago, IL 60630

  Fantastic investment opportunity in Chicago! This 2-flat offers strong income potential with two legal units, each featuring 2 bedrooms and 1 bath, along with hardwood floors throughout. Ideal for investors. The property also includes a nonconforming basement unit, offering additional flexibility and potential for extended living or storage. A detached garage provides an added income stream,

  Niki Syllantavos Redfin Corporation

  5212 N Ludlam Ave, Chicago, IL 60630
• 

  

  /29

  $525,000

  Pending

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

  5042 N Melvina Ave, Chicago, IL 60630

  Beautiful Jefferson Park home offering vintage character, thoughtful updates, flexible living space, and incredible storage! Situated on a quiet residential street near shopping, restaurants, and Austin Foster Park. This large brick home welcomes you with a landscaped front yard and charming porch. Inside, hardwood floors and oversized wood crown molding add classic character. (The living rooms

  Jennifer Teadt-Long @properties Christie's International Real Estate

  5042 N Melvina Ave, Chicago, IL 60630
• 

  

  /13

  $500,000

  • 5 Beds
  • 3 Baths

  5730 W Windsor Ave, Chicago, IL 60630

  This legal 2-flat with a non-conforming garden unit sits on a generous 37-foot-wide lot with garage parking in one of Chicago's most in-demand Northwest Side neighborhoods. Portage Park delivers everything income-focused buyers look for: easy access to CTA bus and nearby Metra service, walkable proximity to grocery stores and everyday retail, and several neighborhood parks within blocks - the

  Ryan Douglas Wells Keller Williams ONEChicago

  5730 W Windsor Ave, Chicago, IL 60630
• 

  

  /46

  $624,900

  $25K PRICE DROP

  • 4 Beds
  • 3 Baths

  4984 N Major Ave, Chicago, IL 60630

  **Beautifully Maintained All-Brick Two-Flat in Desirable Jefferson Park! Well-maintained all-brick two-flat featuring 2 generous 2-bedroom, 1-bath units ~Each unit offers a spacious living room, formal dining room, eat-in kitchen, and a versatile den that can be used as an office, craft room, or additional living space ~Vintage charm throughout includes Craftsman-style oak doors, trim, crown

  Marla Kubik HomeSmart Connect LLC

  4984 N Major Ave, Chicago, IL 60630
• 

  

  /39

  $540,000

  Pending

  • 5 Beds
  • 2 Baths
  • 3,750 Sq Ft

  5501 N Parkside Ave, Chicago, IL 60630

  Step into history with this beautifully preserved Chicago bungalow, where classic craftsmanship meets modern potential. Original stained glass windows cast vibrant light throughout the main level, while exquisite burl wood interior doors add a touch of timeless elegance. The home already features a rare upstairs addition complete with a second kitchen-perfect for multigenerational living, guest

  Andrew Aguilera You Properties LLC

  5501 N Parkside Ave, Chicago, IL 60630
• 

  

  /23

  $329,900

  Pending

  • 2 Beds
  • 2 Baths

  4806 N Milwaukee Ave Unit 2W, Chicago, IL 60630

  Please note: this home does NOT face Milwaukee Ave. Gorgeous and spacious 2-bedroom, 2-bath condo in the heart of Jefferson Park, offering an open-concept layout, garage parking, and a private west-facing balcony tucked away at the rear of the building. The great room offers plenty of flexibility for both dining and living space. The kitchen features 42-inch maple cabinetry, granite countertops,

  Martha Balleza Realty of America, LLC

  4806 N Milwaukee Ave Unit 2W, Chicago, IL 60630
• 

  

  /26

  $579,000

  • 4 Beds
  • 3 Baths

  4923 N Mason Ave, Chicago, IL 60630

  Beautiful, Legal 2 Flat with in-law arrangement in the heart of Jefferson Park. Excellent building includes top floor unit 2 Bed 1 Bath. First floor unit 2 Bed 1 Bath and in-law down for an additional Bed and Bath. Bright open units each equipped with private rear porches. Pictures only reflect second floor unit but first floor is even bigger and more updated. Long time owner, solid and well

  Gregorio Cirone xr realty

  4923 N Mason Ave, Chicago, IL 60630
• 

  

  /13

  $549,900

  • 4 Beds
  • 4 Baths
  • 1,839 Sq Ft

  5137 N Menard Ave, Chicago, IL 60630

  5137 N Menard Ave offers a layout built for daily practicality and easy entertaining in Jefferson Park. The main floor features a defined, formal dining room-ideal for sit-down meals or dedicated hosting space-alongside a functional, updated kitchen with modern updates for immediate move-in readiness. Four full bedrooms and 2.5 baths provide complete flexibility for family living, guest rooms, or

  Corina Flores-Moradi Re/Max Cityview

  5137 N Menard Ave, Chicago, IL 60630
• 

  

  /49

  $464,000

  • 3 Beds
  • 2 Baths
  • 800 Sq Ft

  5505 N Nagle Ave, Chicago, IL 60630

  Charming and efficient single-family home in the heart of Chicago's desirable Jefferson Park neighborhood! This detached 2-bedroom, 2-bathroom residence offers an ideal blend of classic character and modern convenience. Boasting 820 square feet of comfortable, central-air-conditioned living space, this home features an asphalt shingle roof. Perfect for first-time buyers or downsizers, the

  Sean Oneill American Realty Services, Inc.

  5505 N Nagle Ave, Chicago, IL 60630
• 

  

  /36

  $599,900

  Pending

  • 4 Beds
  • 3 Baths

  5430 N Lieb Ave, Chicago, IL 60630

  Located on a tree-lined block in sought-after Jefferson Park, this single-family home is one to remember. This 4-bedroom, 3-bathroom all-brick bungalow has been lovingly maintained over the years and is filled with countless updates. As you first take in the home, you will note the charming curb appeal thanks to fresh landscaping. Walk through the front door and take note of the spacious living

  Melanie Everett Compass

  5430 N Lieb Ave, Chicago, IL 60630
• 

  

  /24

  $389,900

  Pending

  • 3 Beds
  • 1.5 Baths
  • 1,610 Sq Ft

  5228 N Ludlam Ave, Chicago, IL 60630

  ***MULTIPLE OFFERS*** Highest & Best due by 5:00pm, Tuesday, September 22nd. NO Escalation Clauses. NO love letters. Charm, character, and a truly special garden await in this classic Jefferson Park home! From the moment you arrive, the inviting front porch, picket fence, and lush landscaping set this home apart. Step inside to find wonderful vintage details including original woodwork, hardwood

  Kristi Roque Baird & Warner

  5228 N Ludlam Ave, Chicago, IL 60630
• 

  

  /44

  $644,900

  $14K PRICE DROP

  • 4 Beds
  • 3 Baths

  5849 W Wilson Ave, Chicago, IL 60630

  Rare opportunity to own a well-maintained legal 2-flat situated on an oversized 43' x 125' lot in the Jefferson Park/Portage Park area. The property features two spacious units, each with 2 bedrooms and 1 full bath, offering flexibility for owner-occupancy, extended family, or investment. A full basement provides additional finished space, including a full bathroom, an additional room, and a

  John Castelli Castelli Management LLC

  5849 W Wilson Ave, Chicago, IL 60630
• 

  

  /38

  $239,990

  • 2 Beds
  • 1.5 Baths
  • 1,002 Sq Ft

  5447 W Lawrence Ave Unit 203, Chicago, IL 60630

  Beautifully refreshed and move-in ready, this bright 2-bedroom, 1.5-bath second-floor condominium enjoys a prime location directly across from Jefferson Park. Freshly painted and enhanced with brand-new carpeting installed in April 2026, the home features a spacious, functional layout with an expansive living room, a separate dining area, and a generously sized eat-in kitchen offering abundant

  Mark Minorczyk Keller Williams ONEChicago

  5447 W Lawrence Ave Unit 203, Chicago, IL 60630
• 

  

  /43

  $190,000

  • 2 Beds
  • 1 Bath
  • 850 Sq Ft

  5700 W Montrose Ave Unit 1C, Chicago, IL 60634

  Ernesto Escalante Charles Rutenberg Realty

  5700 W Montrose Ave Unit 1C, Chicago, IL 60634
• 

  

  /25

  $345,000

  • 3 Beds
  • 1 Bath
  • 2,239 Sq Ft

  5219 N Marmora Ave, Chicago, IL 60630

  Estate Sale. Being sold as is. SFH Brick 3 bds, 1 bath and a loft area that can be utilized as another bedroom. Hardwood floors throughout home. Large Unfinished basement with endless possibilities for expansion. 2-car Garage. H20 Tank 1/2021. AC Condenser 3/2018. Walking distance to CTA and Austin Foster Park which totals 4.97 acres and contains a junior baseball field, softball field, and

  Jose De Jesus Parkvue Realty Corporation

  5219 N Marmora Ave, Chicago, IL 60630
• 

  

  /19

  $250,000

  Pending

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft

  5865 N Elston Ave Unit 2S, Chicago, IL 60646

  100% CUSTOM-DESIGNED, NEWLY REMODELED! 5865 N Elston Ave is a multi-family condominium building located in the Jefferson Parkneighborhood on the northwest side of Chicago. This traditional, residential property is a reminder of mid-century Chicago, boasting a brick exterior masonry structure with a flat roofline, a perfectly manicured front lawn and easy street parking for guests just yards away.

  Sam Zakarian Century 21 Universal

  5865 N Elston Ave Unit 2S, Chicago, IL 60646
• 

  

  /18

  $559,000

  • 4 Beds
  • 2.5 Baths

  5221 N Marmora Ave, Chicago, IL 60630

  Welcome to your move-in-ready home in the heart of North Jefferson Park! This meticulously maintained Brick English home combines classic Chicago charm with high-end, modern efficiency. This home has been thoughtfully upgraded for the future. Enjoy significantly reduced energy bills with brand-new, fully paid-off solar panels. The exterior is equally impressive, featuring a new roof and most of

  Zakary Dana HomeSmart Connect LLC

  5221 N Marmora Ave, Chicago, IL 60630
• 

  

  /22

  $225,000

  Pending

  • 2 Beds
  • 1.5 Baths
  • 1,000 Sq Ft

  Unlisted Address

  Welcome to 4545 N Milwaukee Ave #6D, a beautifully refreshed 2-bedroom, 1.1 bathroom home in the heart of Jefferson Park. This inviting residence features an open-concept layout that seamlessly connects the living, dining, and kitchen areas-perfect for both comfortable everyday living and entertaining. Enjoy modern conveniences including central air (replaced in 2023), abundant closet space, and

  Loreal Urso Baird & Warner

  Unlisted Address
• 

  

  /10

  $199,500

  $36K PRICE DROP Pending

  • 2 Beds
  • 1 Bath
  • 850 Sq Ft

  5457 W Edmunds St Unit GA, Chicago, IL 60630

  Highly desirable Jeffeson Park area! Nicely updated and well maintained 2 bedroom 1 bath Condo Unit, near I-90 and walking distance to Blue Line and Metra. Storage room included and Coin operated Washer and Dryer in Common Area. Don't miss this great opportunity

  Carlos Rocha Chicagoland Brokers, Inc.

  5457 W Edmunds St Unit GA, Chicago, IL 60630
• 

  

  /26

  $539,900

  • 4 Beds
  • 2 Baths

  5848 W Catalpa Ave, Chicago, IL 60630

  Fantastic investment opportunity in the desirable Jefferson Park neighborhood-a well-maintained and updated 2-flat that offers both turnkey investment potential and the option for owner-occupancy. Each unit features 2 bedrooms and 1 bathroom, complemented by beautiful hardwood floors, central HVAC, and a bonus back porch. The main floor unit boasts modern upgrades, including stainless steel

  Norma Perez Chicagoland Brokers, Inc.

  5848 W Catalpa Ave, Chicago, IL 60630
• 

  

  /19

  $534,900

  $40K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,942 Sq Ft

  4563 N Merrimac Ave, Chicago, IL 60630

  Welcome home to this beautifully maintained 3-bedroom, 1.5-bath home in the heart of Jefferson Park - one of the area's most sought-after neighborhoods! Nestled on a quiet, family-friendly street, this home offers the perfect blend of comfort, convenience, and charm. Inside, you'll find a spacious living room ideal for entertaining or relaxing, along with a finished basement that provides

  Jeffrey Jamrok Village Realty, Inc.

  4563 N Merrimac Ave, Chicago, IL 60630
• 

  

  /46

  $599,900

  Pending

  • 4 Beds
  • 2 Baths
  • 2,914 Sq Ft

  4911 W Argyle St, Chicago, IL 60630

  Welcome to the heart of Jefferson Park in coveted Beaubien School district! This fully renovated 4-bedroom, 2.0- bathroom home boasting three levels of living space on a 31ft. wide lot. Perfect for entertaining, this home features a semi open-concept layout with a great family room with fireplace plus expansive full basement, ideal for additional living and entertaining. This residence offers

  Deborah Hess Compass

  4911 W Argyle St, Chicago, IL 60630
• 

  

  /18

  $459,000

  • 5 Beds
  • 2.5 Baths
  • 2,037 Sq Ft

  5306 N Lynch Ave, Chicago, IL 60630

  CHOICE CORNER LOCATION IN JEFFERSON PARK! This very clean and well-maintained 3-bedroom brick bungalow offers excellent space, flexibility, and a fantastic location. The main level features a flowing living room and dining room combination, along with a kitchen with a comfortable dining area with heated floor. The home has been freshly painted, with new carpeting on the second level. The dry

  Peter Salek Realtogy Co

  5306 N Lynch Ave, Chicago, IL 60630
• 

  

  /42

  $639,900

  • 4 Beds
  • 3.5 Baths

  6051 N Marmora Ave, Chicago, IL 60646

  Charming 4 bedroom, 3.5 bath English Tudor tucked into one of the most desirable pockets of Chicago's Northwest Side! Full of character and natural light, this home features beautiful hardwood floors, fresh paint, and a rare, spacious primary suite with tall ceilings, a huge walk-in closet, and a beautifully renovated private bath. The kitchen is tastefully updated and very spacious featuring a

  Stephanie Welter Keller Williams Success Realty

  6051 N Marmora Ave, Chicago, IL 60646
• 

  

  /23

  $449,900

  • 3 Beds
  • 1.5 Baths
  • 1,296 Sq Ft

  Unlisted Address

  Fabulous fixer-upper in Edgebrook's desirable Indian Woods! This solid built raised ranch is just what you've been looking for! Hardwood floors, plaster walls and a huge unfinished basement waiting for your ideas! Large wide lot w/ side drive and professionally maintained landscaping! Detached garage and large cement driveway plus a partially fenced yard! Close to buses, trains and expressways

  Joan Brennock Baird & Warner

  Unlisted Address
• 

  

  /29

  $455,000

  Open Sat 1PM - 3PM

  • 4 Beds
  • 3 Baths
  • 2,100 Sq Ft

  5445 N Northwest Hwy Unit 1S, Chicago, IL 60630

  Spacious, stylish, and incredibly well located, this duplex-down condo offers an impressive 2 stories of living space with a quiet, private feel in Gladstone Park! The main level features hardwood flooring throughout, along with beautiful details including crown molding, wainscoting, and solid-core interior doors. The kitchen is finished with granite countertops and stainless steel appliances

  Victoria Kroll-Mallek KRG Real Estate

  5445 N Northwest Hwy Unit 1S, Chicago, IL 60630
• 

  

  /18

  $230,000

  Pending

  • 3 Beds
  • 1.5 Baths
  • 1,269 Sq Ft

  4928 N Lester Ave Unit 2B, Chicago, IL 60630

  A rare 3 bedroom and 1.5 bath condo in Jefferson Park! Large eat-in kitchen with newer appliances, ample cabinet and counter space for entertaining and open to the living/dining room. Hardwood floors, new lighting (2026) and freshly painted throughout the unit. Bedrooms are a great size with ample closet space, updated full bath (2026) and also a half bath. Unit has 2 ac wall units, a newer

  Nicole Hajdu Baird & Warner

  4928 N Lester Ave Unit 2B, Chicago, IL 60630

Showing Results 41 - 80, Page 2 of 3