View All Jefferson Park Chicago IL Quick Close Homes Listings

4 Beds ⋅ 3 Baths ⋅ 12693972 MLS ⋅ PENDING Status

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 perfect multi-generational home, or transforming the property into a spacious single-family residence, this home offers endless possibilities to match your lifestyle and goals. Featuring a total of 4 bedrooms, 3 full bathrooms, and a full basement, this property provides the solid foundation to create something truly special while adding your own personal style and finishing touches. Inside, you'll find spacious living areas filled with natural light and traditional layouts that provide excellent functionality. Each unit offers comfortable living and dining spaces, well-sized bedrooms, and kitchens ready to be redesigned and customized to today's preferences. The flexible floor plan allows future owners to preserve the two-unit configuration or reimagine the property as one expansive residence. The full basement adds tremendous value, providing abundant storage space, a dedicated laundry area complete with washer and dryer, and additional room that could serve a variety of future uses, including recreation space, a workshop, hobby area, fitness room, or expanded living space, subject to local requirements and approvals. Outside, the classic brick exterior offers timeless curb appeal and durable construction that continues to be highly desirable. The yard provides space for gardening, outdoor entertaining, summer gatherings, or simply enjoying your own private outdoor retreat. Whether your vision includes enhancing the landscaping or creating additional outdoor living areas, the property offers plenty of opportunity to make it your own. The location is equally impressive. Situated in one of Chicago's most established residential neighborhoods, this home offers convenient access to parks, recreational facilities, shopping, dining, grocery stores, coffee shops, and everyday conveniences. Nearby Portage Park and Jefferson Memorial Park provide green space, athletic facilities, playgrounds, tennis courts, swimming, and year-round recreational activities. The neighborhood is known for its mature tree-lined streets, strong community atmosphere, and well-maintained homes that continue to attract buyers looking for long-term value. Commuters will appreciate the excellent transportation options, including nearby CTA bus routes, Metra service, and quick access to Interstate 90/94, providing convenient travel to downtown Chicago, O'Hare International Airport, and surrounding suburbs. The home is also close to the Six Corners shopping district, forest preserves, golf courses, entertainment venues, restaurants, and a wide variety of retail destinations that make daily living both convenient and enjoyable. Whether you're looking for the flexibility of owner-occupied living with additional rental potential, space for extended family, or the opportunity to create a beautiful single-family home, 5160 W Sunnyside Ave offers the layout, location, and potential to bring your vision to life. With its solid brick construction, 4 bedrooms, 3 full bathrooms, full basement, and highly desirable Northwest Side location, this property is ready for its next chapter and presents an outstanding opportunity to create a home tailored to your lifestyle while building lasting value.

5160 W Sunnyside Avenue, Chicago

$815,000

3 Beds ⋅ 4 Baths ⋅ 12589271 MLS ⋅ CLOSED Status

Multiple offers received. Stunning 4 bedroom 3.5 bath home in sought after Edgebrook Glen offering beautiful park views and a thoughtfully designed semi-open floor plan that blends traditional living with modern comfort. The main level features elegant formal living and dining rooms, perfect for entertaining, along with a bright, updated kitchen equipped with all new appliances and a charming breakfast nook overlooking the outdoors. Upstairs, the spacious primary suite serves as a private retreat with a luxurious soaking tub, double vanity, and sleek European shower. Two additional generously sized bedrooms each offer walk-in closets and share a well-appointed full bathroom. The fully finished basement expands the living space with a large family room, a private fourth bedroom, and an additional full bath, ideal for guests, in-laws, or a home office setup. With scenic park views and access to bike/walking trails this is truly a nature lovers dream. Convenient highway access, close to public transit and quick commute to O'hare.

5658 N Latrobe Avenue, Chicago

$551,508

3 Beds ⋅ 2 Baths ⋅ 12584927 MLS ⋅ CLOSED Status

Beautifully rehabbed 5-bedroom, 2-bath ranch in Jefferson Park offering the perfect blend of space, style, and convenience. This thoughtfully updated home features a spacious, functional layout with five bedrooms and two full modern bathrooms. The main floor showcases a stunning, bright kitchen with custom cabinetry, stainless steel appliances, and elegant quartz countertops with a matching backsplash. A beautifully designed bathroom with a double vanity and a shower-tub combination adds both comfort and style. The main level also includes three bedrooms and a welcoming living and dining room combination, ideal for everyday living and entertaining. The fully finished lower level offers a large family room, two additional bedrooms, a full bathroom, and a dedicated laundry room, providing plenty of flexible space for guests, extended family, or a home office. Quality finishes are found throughout the home. Step outside to enjoy a spacious deck and a fenced backyard-perfect for entertaining, gardening, or simply relaxing. A two-car garage adds extra convenience. Located close to Austin-Foster Park, shopping, dining, everyday amenities, and public transportation. Quick and easy access to the Kennedy Expressway makes commuting a breeze. Don't miss this move-in-ready gem! Property is for sale only.

5423 N Moody Avenue, Chicago

$405,000

2 Beds ⋅ 2 Baths ⋅ 12474905 MLS ⋅ CLOSED Status

Location, space, and convenience are a few of the highlights of this 3 bed / 2 bath home bordering Indian Woods in Jefferson Park. Open the door to your spacious living room / dining room combo - giving you the space you need for your day to day living. Walk through to the expansive kitchen which has plenty of counter space, table space for casual dining (overlooking your huge back yard), and a pantry. The main floor also has two good-sized bedrooms, closet space, and a main bath with a shower / jet tub. Head downstairs to the large recreation room anchored by the decorative fireplace and you will also find the third bedroom with glass block, a full bath, laundry room, and mechanical room. Head out back to your one car detached garage and marvel in the depth of your back yard. Enjoy the Forest Glen Woods, hop onto the bike trails, play nine at Caldwell Golf Course, and take advantage of your transportation options between the Metra, bus, and quick access to the Edens Expressway. Mariano's, shopping, and restaurants are close by for your convenience. All appliances have been updated since 2015, the roof was replaced in 2022, and be comforted with a flood control check-valve system that has kept this home dry throughout. With a few personal touches, you can make this home your own!

5883 N Central Avenue, Chicago

$405,000

4 Beds ⋅ 3 Baths ⋅ 12454378 MLS ⋅ CLOSED Status

Built in 1949, this charming and well-maintained brick home in Jefferson Park is looking for its 2nd owner. You read that correctly - this home was built and maintained for over 75 years now by the same family! Featuring 4 bedrooms and 2.1 baths, this home offers a finished basement and endless potential. A perfect canvas for your design ideas! Recent updates include a full roof tear-off (2024), new tuckpointing, a new patio and sidewalk, soffit, facia, new front and back stairs, front and back railings, new steel side door, plus new gutters and downspouts. Located in the desirable Prussing and Taft school districts, just one block from Dunham Park. Enjoy close proximity to Jewel-Osco, Hagen's Fish Market, Jefferson Park Blue Line and Metra stations, and quick access to the expressway.

4583 N Mcvicker Avenue, Chicago

$439,999

3 Beds ⋅ 3 Baths ⋅ 12443215 MLS ⋅ CLOSED Status

All-Brick Jefferson Park Condo Duplex with 1,800 Sq Ft of living space! Less than a 5 min walk to CTA Blue Line & quick I-90 access-perfect for commuters, flight attendants & airline staff. Just 10 min drive to O'Hare! Features 3 large bedrooms, 2.5 baths, 10-ft ceilings, bright open living areas, and a cozy fireplace. Main-level living room features privacy daytime window tints and motorized blinds. Includes 2 parking spaces. Updates: furnace & A/C (2024), sump pump w/backup battery (2024), GE appliances (2023), patio door (2023), 94" x 70" front window (2022), fresh paint throughout! Close to shopping, dining, parks & transit.

4946 N Lockwood Avenue Unit #1N, Chicago

$227,000

2 Beds ⋅ 1 Baths ⋅ 12424525 MLS ⋅ CLOSED Status

-- Back on the Market! The previous buyer made it all the way to closing day - inspection was smooth, appraisal came in right on value, loan was fully approved, and the HOA gave the green light. Unfortunately, their divorce and related legal matters forced them to back out at the last minute. Their situation has absolutely nothing to do with the home, which means this beautiful condo is now ready for the next lucky buyer! -- ***Welcome to this beautifully updated two-bedroom, one-bath condo located in the heart of Jefferson Park-one of Chicago's most vibrant and desirable neighborhoods. Situated on the first floor and perfectly positioned at the intersection of I-90 and I-94, this 1,000-square-foot gem offers an unbeatable combination of urban convenience and neighborhood charm, providing quick access to downtown Chicago while maintaining a cozy, community feel. Inside, you'll find a modern, inviting space featuring a brand new kitchen and bath, complemented by pristine, brand new hardwood flooring throughout. A wall-mounted, brand new AC unit ensures your comfort year-round. Additional conveniences include two assigned parking spots and on-site laundry facilities, all while keeping HOA fees at an affordable rate. Jefferson Park is known for its rich local culture, eclectic mix of dining and shopping options, and excellent public transportation links-making it a sought-after destination for those who want to experience the best of Chicago living. Whether you're heading downtown for work or leisure, this location offers the perfect balance of accessibility and a close-knit community vibe. Don't miss your chance to own a slice of this dynamic neighborhood-schedule your viewing today!

4976 N Milwaukee Avenue Unit #101, Chicago

$265,000

2 Beds ⋅ 2 Baths ⋅ 12343632 MLS ⋅ CLOSED Status

Are you looking for a move in ready, 2 bedroom 2 bath condo in a newer (2001) small (6 units) building? This is it!! This freshly painted unit is located on the desirable first floor for easy access and convenience. A perfect floorplan - a bright and open layout with spacious living and dining areas. The kitchen offers ample cabinet space and flows seamlessly into the main living area. The primary suite has new carpet, and includes a private bathroom and generous closet space, while the second bedroom and full bath provide flexibility for guests, a home office, or a roommate setup. Relax in front of your gas fireplace or on your private patio. Additional highlights include in-unit laundry, central heating and air, and dedicated parking. Ideally located close to shopping, dining, public transit, and major highways. Roof redone in 2017 with a 25 year warranty. No smoking units. No pets. No rentals. Whether you're a first-time buyer, or downsizing, this freshly painted, move-in ready condo is a must-see. Quick close possible.

5709 W Lawrence Avenue Unit #1W, Chicago

$415,000

3 Beds ⋅ 2 Baths ⋅ 12261536 MLS ⋅ CLOSED Status

Newly refreshed ranch home with 3 bedrooms plus additional bedroom/office in the finished basement. New kitchen with white cabinets, quartz countertops and all new LG stainless steel appliances. New LG washer/dryer. Refinished hardwood floors and freshly painted throughout. Main floor bath with new vanity and toilet. Family room and 2nd bath in basement level. Fantastic and desirable location within a few blocks of Jefferson Park Transportation Center with Blue Line CTA, commuter train and bus terminal. Many new construction homes in immediate area. Easy access to I-90. Oversize newer garage with attic storage. Fenced yard with deck. Quick close possible. A must see.

5359 W Winnemac Avenue, Chicago

$495,000

3 Beds ⋅ 2 Baths ⋅ 12199533 MLS ⋅ CLOSED Status

Spacious Tudor-Style Bungalow with Modern Upgrades and Prime Location! Discover this charming 5-bedroom, 2-bath Tudor-style bungalow that combines classic character with thoughtful updates. Step inside to a welcoming living room, where west-facing windows flood the space with natural light, and a cozy fireplace adds warmth and charm. The main level boasts two spacious bedrooms, including one with a rare walk-in closet, and a fully updated bathroom (2014). The renovated (2024) eat-in kitchen is a chef's delight, featuring stainless steel appliances, sleek quartz countertops, 42" cabinetry, and a convenient breakfast bar for quick bites. Enjoy larger meals in the adjacent formal dining room, complete with rich hardwood floors and elegant crown molding. The lower level offers fantastic versatility with additional living space, two bedrooms with one that has it's own full bath, a second kitchen, and a separate laundry area. Perfect for extended family or guests! Bring your vision to the upper level, where you'll find a bedroom plus an expansive area originally designed as the primary suite-ready to be customized to suit your needs. Outside, a large patio and lush backyard provide a wonderful space for relaxation and gatherings, with a two-car garage and room for a storage shed for added convenience. Prime Location! Less than 1 mile from Jefferson Park, with easy access to I-90, and close proximity to the Gladstone Park Metra and Jefferson Park Blue Line. Thoughtful, owner-made updates over the past 18 years. This is not a flip; it's a well-cared-for home with a warm, welcoming ambiance. Main level painted (2024), basement painted (2023), water heater (2024), carpet stairs to 2nd level + bedroom (2024).

5129 N Menard Avenue, Chicago

$390,000

3 Beds ⋅ 2 Baths ⋅ 12187682 MLS ⋅ CLOSED Status

Mint 3-Bedroom brick ranch with beautiful hardwood floors. Quality remodeled kitchen with granite countertops, vented stove hood, white cabinets, tiled backsplashes and many extras. Brand new hot water heater, spacious family room in lower level with full bathroom, utility area and large storage area. Brick 2-car garage with new polyurea floor. Extra insulation in attic and windows have been replaced. Popular Jefferson Park is located near Blue Line and Metra transportation and quick access to I-90/I-94. Close to new local shops, cafes, bars, breweries and restaurants. You will see even more highlights after you attend your showing!

5442 N Central Avenue, Chicago

$435,000

4 Beds ⋅ 2 Baths ⋅ 12166180 MLS ⋅ CLOSED Status

Welcome home to this charming recently updated checkerboard Octagon Bungalow on quiet tree-lined street! This home is truly a special place with nothing to do but move in. Located on a 30' wide lot this home brims character and warmth from every room. From the foyer entry, you will love walking into the living room with beautiful hardwood floors, its decorative fireplace surrounded by original wood built-in cabinets, crown moldings, and the stained-glass windows. An arched wall opening leads into the large dining room, while the kitchen with classic maple flooring is tastefully upgraded for modern living with newer stainless appliances and a coffee bar. Off the kitchen is your light filled sunroom overlooking the backyard.. Two large bedrooms and recently updated full bathroom with bath complete this level. The primary bedroom upstairs facing the yard with two walk-in closets shares a full bath with an equally spacious second bedroom. Large unfinished basement which includes laundry with tons of space for your finishing ideas, storage, etc... Central air and heat, brand new furnace and water heater, copper plumbing and newer electrical. No garage but can be permitted to add. Great Jefferson Park location near Blue Line and Metra Transportation & quick access to I90-94. Close to new local shops, coffee shops, bars, breweries & Restaurants.

5224 N Monitor Avenue, Chicago

$375,000

4 Beds ⋅ 3 Baths ⋅ 11979942 MLS ⋅ CLOSED Status

WELCOME HOME to the property of your dreams in beautiful Gladstone Park! This solid brick home exudes charm with its vintage features and countless updates. As you step inside, you'll be greeted with all the feels of a traditional Chicago bungalow including wood floors, high ceilings, rich trim and baseboards, custom fixtures, elegant archways, and much more! The warm and inviting atmosphere leads you through spacious rooms that are not just big; they are extra-large, providing ample space for your lifestyle. A full eat-in Kitchen, Formal Dining Room, huge Living Room, and FOUR bedrooms round out this move-in ready charmer- All you need to do is just add your personal flair and finishing touches! The yard has plenty of room for a garden, hot tub, or She Shed... The choice is yours! Back inside, the basement boasts high ceilings and the potential to easily finish this space according to your preferences. The newer boiler ensures efficient heating, while the flood control system and professionally sealed basement guarantee a secure and dry environment. Located in the quiet and beautiful Gladstone Park, this home is a haven for nature enthusiasts and families alike. Enjoy the convenience of being close to three picturesque playgrounds, golf courses, and highly sought-after Taft High School. Forest preserves nearby provide opportunities for running, biking, and refreshing walks to enjoy all of the Chicago seasons. For those who enjoy adventure and fitness, close access to the Chicago River, bike trail, and Thaddeus S. "Ted" Lechowicz Woods adds to the appeal. Commuting is also a breeze with an easy walk to the Gladstone Park Metra station and proximity to the Jefferson Park Blue Line and Metra station via the Milwaukee Ave bus. Quick access to the major 90 and 94 highways ensures a seamless journey to downtown, airports, suburbs, and beyond. Don't miss the opportunity to make this amazing Chicago bungalow yours! See it today!

5827 N Markham Avenue, Chicago

$298,700

3 Beds ⋅ 2 Baths ⋅ 11970423 MLS ⋅ CLOSED Status

PERFECTLY RENOVATED CORNER-UNIT WITH DUAL BALCONIES ! Enjoy convenient Portage Park living in this SPACIOUS 3bed/2bath home! Note the charming brick curb appeal, ample parking, security door entrance, & peaceful location! Proceed to this top floor unit and notice the tranquil building, concrete walls, & well maintained common areas! As you enter you will be greeted with a formal foyer boasting ample closet space! Entertain with ease in the expansive living room featuring hardwood floors, modern recessed lighting, and a sunny west facing balcony! Enjoy hosting holidays in the enormous FULLY RENOVATED EAT-IN-KITCHEN! This stunning kitchen boasts AMPLE STORAGE SPACE, NEW cabinetry, soft close doors/drawers, recessed lighting, GRANITE counters, STAINLESS STEEL appliances, a 5-burner stove, water connection to the fridge, & IN-UNIT LAUNDRY! The adjacent second balcony is perfect for taking in your morning coffee and offers beautiful east-facing views! Retreat to the spacious primary suite offering plenty of room for a king bedroom set, dual closets, vanity space, & PRIVATE EN-SUITE! The private primary bathroom features a modern spa-like shower with tile surround and glass enclosure, brand new vanity, modern lighting, & ample natural light! This property also includes 2 spacious guest bedrooms with a dedicated guest bathroom! Enjoy a well run HOA where the association covers your monthly Heat, Water, Gas, Parking, Common Insurance, Exterior Maintenance, Lawn Care, Scavenger, & Snow Removal! ASSIGNED PARKING, PRIVATE STORAGE UNIT, IN-UNIT WASHER & DRYER, RESPONSIBLE HOA, & INCREDIBLE LOCATION! This location has it all! Enjoy living near the Metra, public trans, and having quick access to highways! Just blocks from nearby shopping, restaurants, parks/dog parks, entertainment, & MORE! Enjoy living in the top corner unit of this immaculately updated property! This is the one you've been waiting for!

4535 N Long Avenue Unit #3A, Chicago

$297,000

3 Beds ⋅ 2 Baths ⋅ 11838657 MLS ⋅ CLOSED Status

A great opportunity to own a starter home in Jefferson Park/Gladstone neighborhood! This Chicago bungalow has plenty of living space with 3 bedrooms and a den plus a basement perfect for recreational space. The location is perfect for commuters with easy access to the commuter train, bus and highway. Quick close is possible!

5633 N Miltimore Avenue, Chicago

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