Jefferson Park Homes for Sale

Welcome to 5136 Winona St, an exceptional Chicago bungalow that seamlessly blends timeless character with thoughtful modern updates, ideally positioned on a quiet, tree-lined street in the heart of Jefferson Park. Situated on an extra-wide lot, this residence offers an expansive and highly functional layout across three beautifully finished levels. The main level showcases sun-drenched living and

Maria Montes De Oca Keller Williams Premiere Properties

Luxuriously renovated 1.5-story single-family home situated on an oversized 30x125 lot. This spacious and functional home is thoughtfully designed to accommodate a variety of lifestyle needs while maintaining a warm and inviting atmosphere. Home features 6 bedrooms and 3 full bathrooms, well distributed across three levels. A welcoming front entrance leads into a bright, open-concept main level.

Iwona Jankowska HomeSmart Connect LLC

Completely rehabbed all-brick English Tudor in beautiful Jefferson Park, perfectly set on an extra-wide 40' x 133' lot with a spacious backyard and oversized deck ideal for entertaining. This thoughtfully redesigned home blends classic character with modern efficiency and upscale finishes throughout. Featuring 4 bedrooms (2 upper level, 1 main, 1 lower), each with custom closet organizers, and 3

Dora Karlos Berkshire Hathaway HomeServices Starck Real Estate

Welcome to this Big House Ideal for a Large Family or for Extra Income. MAIN Level Features 2 Bedrooms with Separate Living and Dining Rooms, Bathroom, Family Room that can also be used as another bedroom, Updated Kitchen with Plenty of Cabinets with Granite Countertops. UPPER Level Comes 2 Large Bedrooms, Full Bathroom, Kitchen and Living Room with Separate Entrance. The BASEMENT Offers 2

Pedro Astudillo RE/MAX City

Welcome to this beautifully updated home where modern finishes, thoughtful design, and inviting living spaces come together seamlessly. From the moment you arrive, the striking curb appeal sets the tone with newer exterior finishes, a welcoming front porch with seating space, and meticulously maintained landscaping. Inside, you'll find a warm and stylish living room highlighted by bay windows,

Josephine Ceglarek Coldwell Banker Realty

Discover an incredible opportunity in the heart of Jefferson Park with this versatile 4-bedroom, 2-bathroom home, perfectly suited for savvy investors or motivated homeowners looking to build instant equity. The main level boasts classic hardwood floors throughout, featuring three comfortable bedrooms and a full bath, while the expansive upstairs primary suite provides a private retreat with its

Ivan Santos O'Neil Property Group, LLC

A luxurious penthouse on the top floor of a three-apartment building. Step inside and you'll find everything you desire. Beautiful hardwood floors throughout. Exceptionally bright, spacious rooms. You'll be flooded with natural light, including skylights above to truly warm the space. This unit's fireplace can be used with gas or real wood. The kitchen boasts stainless steel appliances and

Eric Sadowski arhome realty

Nice corner well maintained legal 2 flat with additional in law apartment in basement. All are spacious apartments including basement. 1st and 2nd floor units have formal dining rooms. All separate utilities. New furnace and AC units on each apartment. 1ST and 2nd floor have new SS appliances. Coin-operated laundry located in the basement. Good rents make this a great investment.

Tony Garcia Terra Nova Realty Group Corp

Suburban Size Home With City Address! Jefferson Park Impressive 2014 Built Extra Wide 5 Bedroom 3.5 Bath Newer Construction Resale With 4 Large Bedrooms Upstairs. Great Sunlight Throughout This Entire Home With Oversized Windows and Dramatic Ceiling Height On Every Level. Full Hardie Board Siding All Around Exterior and New Roof Completed on Home and Garage in 2025. Front Living Room With Bay

John Huebner @properties Christie's International Real Estate

Rare opportunity to own a well-maintained legal 2-flat in the highly sought-after Jefferson Park neighborhood. Ideally located near O'Hare Airport, major expressways, public transportation, and shopping, this property offers both convenience and long-term value. The building features a total of three bedrooms and three full bathrooms, with Unit 2 fully updated and showcasing modern finishes. A

Spencer Engquist HomeSmart Connect LLC

One of two impeccable 4 bedroom, 3.1 bath new construction single-family homes steps from the Metra in Jefferson Park. Spacious floor plan featuring design forward fixtures and finishes. Open concept living/dining area with direct vent gas fireplace and beautiful oak hardwood flooring. Chef quality eat-in kitchen perfect for entertaining features stainless Bosch appliance package, oversized

Jason O'Beirne Jameson Sotheby's Intl Realty

5333 W Foster Ave presents a rare opportunity in Jefferson Park with exceptional versatility and long-term upside. This 3-unit property includes a separate coach house and sits on an oversized DOUBLE-LOT, offering strong income potential in one of Chicago's most accessible Northwest Side neighborhoods. With parking for up to 4 cars and tenants already in place, this is an ideal fit for investors,

Phillip Younan Fulton Grace Realty

Excellent opportunity to own a well-maintained 2-flat in the highly desirable Jefferson Park neighborhood, offering strong rental potential and an ideal setup for owner-occupants. This classic Chicago multi-unit features two spacious units, a finished basement, and shared laundry, making it a versatile investment in one of the city's most commuter-friendly areas. The first-floor unit offers 2

Cory Tanzer Option Premier LLC

Meticulously maintained, bright & sunny 2 bedroom + den, 2 bath townhome in highly desirable Jefferson Park location! This unit is tucked behind the front-facing Lawrence Avenue units giving the feel of being on a quiet, private street within a charming courtyard setting. Courtyard is lined with blooming trees and exteriors were recently painted in stylish gray tones. Inside, enjoy large living

Stephanie Pagone Compass

Welcome to Jefferson Park!! This charming Chicago classic corner 2 flat is well maintained and sits on an oversized lot. Perfect for investors or owner-occupants looking to generate rental income potential. Hardwood floors thru-out in both units and generous room sizes. Basement includes washer/dryer for each unit and separate storage spaces. Basement also gives additional living space plus two

Gerry Belpedio Weichert, Realtors - All Pro

Bright and sunny Dutch Colonial two-unit building with an in-law unit in Portage Park. Each unit offers 2 large bedrooms divided by updated bathrooms with an in-law suite in the basement that includes a one bedroom/studio with one bathroom. The property now includes modern heating and cooling systems in all three living areas including ductwork. Unit 1 had additional updates including beautiful

Sarita Scherpereel Kale Realty

Spacious and well-maintained 2-bedroom, 1.5-bath second-floor condo offering a functional layout and an unbeatable location directly across from Jefferson Park. This recently painted unit features a large living room, a sizable dining room, and a kitchen with abundant cabinet and counter space plus room for a breakfast table. New carpet installed April 2026, central A/C replaced in 2017,

Mark Minorczyk Keller Williams ONEChicago

RARE FIND! Step inside this charming 2 bed, 1 bath single family home in the heart of Jefferson Park! Featuring a finished basement with an additional 2 beds, 1 bath and 2 car garage (pull through). Rehabbed in 2026 this home features NEW brick face on the exterior, electric, drywall, insulation, widows, cabinets, lights/fixtures, doors, flooring, furnace, plumbing, wet bar, updated bathrooms and

Megan Grealy Baird & Warner

THIS SUN-FILLED 2 FLAT WITH GREAT CURB APPEAL OFFERS A WONDERFUL OPPORTUNITY FOR INVESTORS OR HOME OWNERS. 1ST FLOOR IS ON MONTH TO MONTH LEASE-PERFECT IF YOU'D LIKE TO BE OWNER OCCUPANT. OR THEY MAY STAY IF YOU PREFER. CURRENTLY BLDG FULLY RENTED! LOCATED IN THE HEART OF LOVELY GLADSTONE PARK. THERE'S ALSO AN ADDITIONAL NON-CONFORMING LIVING ARRANGEMENT IN BASEMENT & A ONE CAR GARAGE WITH BRAND

Christine Gordon Northwest Real Estate Group

Beautifully updated 2 bed / 2 bath condo in an intimate, well-maintained 6-unit all-brick building in the heart of Jefferson Park! This spacious home features an upgraded kitchen with granite countertops, cherry cabinetry, and newer stainless steel appliances. Hardwood floors run throughout the main living areas, with brand new carpeting in both bedrooms. Oversized room sizes and an expansive

Mario DiLorenzo Keller Williams ONEChicago

Great opportunity to own this recently renovated all brick two flat building with additional garden in-law apartment and gorgeous fenced yard and new oversized three car garage that accomodates big veichles. The property features large two bed 1 bath units on 1st and 2nd level (owner's unit) are with CENTRAL AIR AND HEATING and updated kitchens and bathrooms. Tenants are paying own utilities

Milenko Miljevic Coldwell Banker Realty

Rarely available, sun-drenched top-floor corner unit in the heart of Jefferson Park. This vintage-style residence, lovingly maintained by a long-time owner, offers charm paired with everyday comfort in a beautiful courtyard building. Welcoming 2-bedroom, 1-bath home features a bright and spacious living area, filled with natural light from multiple exposures, creating a warm and inviting

Jadranka Signoretto Atlas Realty Group, Inc.