Jefferson Park, Chicago IL · Curated MLS Search

Homes for Sale in Jefferson Park, Chicago IL

An editorially curated view of every active homes for sale listing in Jefferson Park, Chicago IL. Updated in real time from the local MLS, presented without the noise.

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About Homes for Sale in Jefferson Park, Chicago IL

Jefferson Park runs on the Blue Line and Metra, and that's no small thing. It's one of the best-connected corners of the Northwest Side. Plenty of folks who clock in downtown still park themselves here because the commute actually works. The transit hub sits at the center, and the rest of the neighborhood spreads out from it.

Most of the housing is brick bungalows and two-flats. Solid stuff. These homes have stood up for decades and it shows in the tight mortar joints and square doorframes. The side streets stay quiet under a canopy of old parkway trees. You'll find families who've been here forty years living next to people who just caught on to the value. And Milwaukee Avenue keeps its bakeries, taverns, and corner shops busy without the crowds spilling off the sidewalks.

Why Buy Homes for Sale in Jefferson Park, Chicago IL?

Buy here if you want real Chicago at a fair price and a commute that won't wear you down. You get room to breathe, character in the brick, and a block that feels like a neighborhood. The Kennedy and O'Hare are right there when you need them. This is practical living that still leaves you time to actually enjoy where you live.

Ready to find your ideal homes for sale in Jefferson Park? Contact Chicago Real Estate Source today at (312) 788-7079 to schedule a showing or start your personalized home search.

Jefferson Park, Chicago IL Market Snapshot

Inventory here shifts week to week. The listings on this page pull straight from the MLS, so what you see is what's actually for sale right now.

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Homes for Sale in Jefferson Park, Chicago IL

$679,000

4 Beds ⋅ 2 Baths ⋅ 12752583 MLS ⋅ NEW Status

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 located on the first floor. The second level offers two generously sized bedrooms and a versatile sitting area, complemented by brand-new carpeting. The full finished basement significantly expands the living space with two additional bedrooms, a recreation room with brand-new carpet, full bathroom, laundry room, and cedar closet. A flood-control system has also been installed for added peace of mind. Outdoors, enjoy a fully fenced yard with a stone patio-ideal for entertaining, relaxing, and summer gatherings. A rare extra 45 x 125 lot provides remarkable additional space for gardening, recreation, or creating a private outdoor retreat. A complete roof tear-off and replacement was completed just a few years ago. Ideally located near Caldwell Woods, the North Branch Trail, Indian Road Park, forest preserves, golf courses, Metra, shopping, dining, and everyday conveniences. A distinctive Chicago bungalow offering historic charm, beautiful original woodwork, flexible living space, and an unusually generous property.

5720 N Manton Avenue, Chicago

$649,900

4 Beds ⋅ 3 Baths ⋅ 12746405 MLS ⋅ NEW Status

**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 molding and hardwood floors. The finished basement provides an additional full bathroom and laundry area, offering excellent flexibility and storage ~Enjoy outdoor entertaining in the private, fenced yard, ~Oversized two-car garage for parking ease **Prime location easy access to bus service, the CTA, Metra, and I-90/94. Jefferson Park offers an array of restaurants, shops, parks, and neighborhood amenities ~Updates over the years include: Gutters and roof(2 yrs) with Ice melt system, Water heater (2 yrs), 1st floor kitchen, Vinyl windows on second floor, ~Electric Panels ~Tuck-pointing ~Garage door and opener ~Excellent opportunity to live in one unit and rent the other! This home has been maintained over the years but is being sold AS-IS.

4984 N Major Avenue, Chicago

$589,990

4 Beds ⋅ 3 Baths ⋅ 12756771 MLS ⋅ NEW Status

This meticulously transformed 4-bedroom, 3-bathroom home in a quiet corner of Jefferson Park features a sun-filled main floor with solid hardwood floors, a spacious family room, and a versatile bonus room perfect for an office or bedroom. Modern high-end stainless-steel appliances, dual HVAC systems for superior winter and summer comfort, luxurious bathroom vanities and fixtures, and premium porcelain tile throughout. The chef's kitchen showcases a stunning white quartz island and premium cabinetry, perfect for family gatherings and entertaining guests. Upstairs, there are three generous bedrooms and a full bath, while the finished basement adds extra living space, another full bathroom and ample storage. Outside, a privacy-fenced yard and oversized entertaining patio await. Topping it off are direct expressway access, CTA and Metra proximity, and walkable restaurants, retail, and excellent schools. There is nothing left to do but move into your new luxurious home. New garage door 2026, water heater and 2nd floor heater, and air conditioner installed 9/2026

6218 W Foster Avenue, Chicago

$399,900

3 Beds ⋅ 2 Baths ⋅ 12755813 MLS ⋅ NEW Status

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 are using it for storage, but it is heated and has replacement windows. Close to I94/90, walking distance to Metra and Blue Line, walking and biking paths.

5425 N Linder Avenue, Chicago

$599,900

5 Beds ⋅ 3 Baths ⋅ 12755079 MLS ⋅ NEW Status

JEFFERSON PARK GEM WITH A BACKYARD RETREAT LIKE NO OTHER! Meticulously maintained and exceptionally inviting, this charming 2 flat, within walking distance to Jefferson Park station, offers spacious living and dining rooms, beautiful hardwood floors, a newer kitchen, a 2nd floor rental unit and a fully finished basement ideal for extended family, guests, recreation, or additional living space. But the true heart of this home is the extraordinary two-level rear deck. Directly connected to the house and accessible from both the first and second levels, this expansive outdoor living space is an entertainer's dream. A covered gazebo, mature grapevines, warm wood decking, and a built-in hot tub create a private backyard oasis that feels more like a destination than an ordinary city backyard. It's the perfect setting for summer gatherings, quiet evenings, morning coffee, or relaxing in the hot tub surrounded by greenery. The oversized, fully fenced yard provides exceptional privacy and additional space for entertaining, gardening, or enjoying the outdoors. This is more than a very nice Jefferson Park home-it is a home with a truly special outdoor lifestyle.

5128 W Ainslie Street, Chicago

$499,000

12755075 MLS ⋅ NEW Status

Highly visible 3,125 SF office/warehouse building with 25' of frontage along Elston. Located in a bustling mixed-use neighborhood on Chicago's Northwest Side. The versatile layout includes private offices, an open office area, two washrooms, a break room, and a rear 20' x 30' warehouse with 10.5' ceiling height and a drive-in door. The property offers excellent flexibility for a variety of users, including office, retail, warehouse, service, and other commercial uses. B3-1 zoning provides additional flexibility for future use. Conveniently located approximately one mile from I-90, two miles from I-94, and near CTA transportation.

5962 N Elston Avenue, Chicago

$575,000

4 Beds ⋅ 2 Baths ⋅ 12754787 MLS ⋅ NEW Status

City-certified two-flat in the heart of Gladstone Park offering exceptional flexibility for investors, owner-occupants, or multi-generational living. Thoughtfully updated over the years, this well-maintained property features remodeled kitchens and bathrooms on both the first and second floors, along with an updated first-floor primary bedroom. Each unit offers comfortable living space, while the second-floor apartment features two private entrances and an expanded rear deck overlooking the beautifully landscaped yard. A partially finished basement includes an in-law suite, with 1 bedroom and 1 full bath providing additional flexible living space. Outside, you'll find a true urban oasis with raised garden beds, fruit trees, a patio, and mature landscaping that creates a private retreat. The insulated 2.5-car garage was fully rehabbed in 2023 and offers excellent storage or workshop potential. Additional improvements include newer windows, hardwood floors, and numerous updates throughout. Interior stairs connecting the first and second floors remain behind the dining room wall, offering the potential for a future single-family conversion if desired. This versatile property combines income potential, beautifully maintained outdoor space, and a prime Gladstone Park location. Property is being sold As-Is.

5942 W Thorndale Avenue, Chicago

$579,900

5 Beds ⋅ 3 Baths ⋅ 12754676 MLS ⋅ NEW Status

What a yard! Gorgeous frame 2 unit spanning 2 lots in Jefferson Park side of Portage Park Chicago. Fully enclosed, this double lot has mature landscaping, an oversized garage, raised patio and additional storage shed. It doesn't lack hang out space nor growing space! This 2 unit has a partially finished basement with a bedroom/bar setup and full bath. The attic is unfinished with further expansion potential. The second floor has central heat and air with a brand new condenser and updated fridge. It features all hardwood, original hutch and high ceilings. Most of the windows have been updated in the last 15 - 20 yrs. Roof estimated 10-15yrs old. The 1st floor is boiler heated with 2 large bedrooms and a big kitchen with back sunroom. This unit is in need of some TLC. Unit 1 and garden are vacant and ready while 2nd floor's lease ends in Feb. 28th 2027. Great location by greenspace, walk to the Metra, bus and Jeff Park Blue line transit center and just 2 blocks from Jewel, great dive bars, Starbucks, Prussing Elementary, great Pilipino and Polish restaurants.. ALL within a 5 minute walk...

5753 W Giddings Street, Chicago

$929,000

4 Beds ⋅ 4 Baths ⋅ 12754500 MLS ⋅ NEW Status

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 main level is filled with natural light from all angles and features a stunning kitchen with custom cabinetry, quartz countertops, stainless steel appliances, and a large island overlooking the seating and dining areas anchored by a cozy electric fireplace, with a bonus room attached, perfect for a sunny office space! Plus an ample living area also on the main level leading right out to your own private oasis. Step outside to a beautifully landscaped backyard with a paver patio, creating the perfect setting for summer gatherings or quiet evenings at home. On the top floor, start your mornings with coffee on your private balcony right off the spacious primary suite facing South, flooding the space with more natural sunlight. Enjoy the convenience of second-floor laundry where all 4 bedrooms live. Downstairs, the finished lower level expands your living space featuring a full wet bar, full bath, and a versatile bonus room perfect for a guest suite, home office, gym, or 5th bedroom. Designer lighting, custom window treatments and dual HVAC systems, add comfort and peace of mind. PLUS 2.5 car garage with EV parking! Ideally located in the top-rated public school district - Beaubien Elementary just one block over and Taft High School nearby. Plus surrounded by plenty of parks & hiking trails, the CTA Blue Line, Metra stations and I-90/94, this home offers the perfect blend of city convenience, and neighborhood charm. *Also available for rent at $7,900/month.

5047 W Winnemac Avenue, Chicago

$295,000

2 Beds ⋅ 2 Baths ⋅ 12754394 MLS ⋅ NEW Status

Beautiful, freshly remodeled second floor 2 bedrooms 2 full bathrooms condo for sale in prime Chicago location. This condo features specious room sizes, good closet space, storage, separate dining area, eat in kitchen with the large island and a balcony right off the living room. Entire unit was freshly remodeled with modern touches! New flooring, heated bathroom's floors, new kitchen with under the cabinet's lights, newer appliances etc. This unit has a one off street assigned parking space. This unit has it's own laundry in the unit! Also additional storage unit and a coin laundry in the basement. Walking distance to Metro, grocery stores, banks, restaurants and gym. Do not miss it, will not last long! Rentals allowed, so investors welcome!

5322 W Windsor Avenue Unit #2C, Chicago

$340,000

3 Beds ⋅ 2 Baths ⋅ 12754165 MLS ⋅ NEW Status

Corner brick raised ranch single family home in NW Jefferson Park. Spacious 3 bed, 2 bath with over 1400 sf plus a tall, semi-finished basement. Hardwood floors under carpet, large bedrooms with generous closet space and an eat in kitchen. Primary bedroom has exposed oak floors, partially gutted en-suite bath and a large walk in closet. Gas forced heat and central air, roof approx 15 yrs old. 27'X124'corner lot zoned RS-2 with a detached 2 car brick garage. Property needs updating and TLC, this is an Estate Sale and being sold AS-IS. Great location near the Kennedy, blue line, shopping, dining, parks and forest preserves. Great opportunity to become a part of this awesome neighborhood!

5400 N Mulligan Avenue, Chicago

$230,000

3 Beds ⋅ 2 Baths ⋅ 12754215 MLS ⋅ NEW Status

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 furnace (2021) and the building has coin-op laundry on the first floor, storage and comes with 1 assigned parking spot. Plenty of natural sunlight. Block away from the Metra, Blue line and CTA buses. Walking distance to plenty of restaurants, grocery store, Jefferson Park and Starbucks! Close to the 90/94 expressways. Investor friendly. H&B due Monday, 9-14 @ 9am.

4928 N Lester Avenue Unit #2B, Chicago

$1,264,900

6 Beds ⋅ 4 Baths ⋅ 12754087 MLS ⋅ NEW Status

Rare historic and expansive 4 bed/2.5 bath + 2 bed/1 bath residence set on a raised elevation and oversized 9,125 SF corner lot in the Beaubien/Taft school district. Designed by noted Chicago architect Albert A. Schwartz, known for several landmark Chicago buildings, this architecturally significant "triple-thick/all-face" brick home offers a rare combination of historic craftsmanship, structural quality, and thoughtful modern updates. Soaring 9'7" ceilings, original custom oak woodwork, oversized 84" solid oak interior doors, a substantial custom oak entry door, custom wood storm door, original glass chandeliers, stained-glass windows, and a dramatic 96" balcony door showcase a level of detail rarely found today. Custom solid oak Pella front picture windows with authentic grids further complement the home's original character. Extensive recent improvements include a new large AZEK deck with built-in lighting atop a purpose-built concrete balcony, a reimagined kitchen with island, under-cabinet lighting and breakfast area, updated bathrooms, double-sided illuminated gas fireplace, new rear and basement stairs, Unico A/C, additional new windows, new balcony door, tuckpointing, gutters, soffits, tiled portico roof, extensive concrete work, and more. A radiant heat system provides quiet exceptional comfort, even warmth throughout the home without drafts or temperature fluctuations, offering efficient, consistent heating while preserving the integrity of the home. The extra family room is surrounded on three sides by architectural windows and features a fireplace, built-in shelving, and beautiful natural light. The private fenced and landscaped lot offers exceptional flexibility with an oversized full-brick 2-car garage, 2-car driveway, additional 2-car side parking pad for up to 6 total parking spaces, and a charming approximately 200 SF original accessory outbuilding, recently updated with new siding, windows, and doors, offering flexible use as additional storage, a studio, entertaining space, workshop, or seasonal. The purpose-built concrete balcony overlooks mature landscaping and offers seasonal skyline views. Compliments of the home's raised elevation and superior site grading, the bright 2 bed/1 bath garden-level unit with large above-grade windows and abundant natural light that create an inviting, highly-functional living environment. The flexible garden-level arrangement has existed for more than 100 years and offers excellent potential for multi-generational living, guest accommodations, home office use, or additional income with a private entrance. Ideally located near the Jefferson Park transportation hub with convenient access to the Metra and Blue Line, nearby Forest Glen Metra, and I-90/94. A rare opportunity to own a truly-distinctive Northwest Side residence where architectural pedigree, oversized scale, historic craftsmanship, abundant parking, and modern functionality come together in one extraordinary home.

5100 N Long Avenue, Chicago

$250,000

2 Beds ⋅ 1 Baths ⋅ 12752443 MLS ⋅ ACTIVE Status

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. Fortunately, the rear of the property includes a paved outdoor lot with designated, assigned parking spaces for building residents. The roof and windows have been recently renovated as well. When entering one of the two secured entrances on either side of the building, you will find SMART LOCKS already installed on 2S for those of us who don't wish to scramble for our keys. Speaking of, the majority of this unit has been thoughtfully designed to make everything SMART-from the thermostat to the recessed lighting (with a "movie-theatre" dimmer feature.) Upon entering, you will be greeted with oak hardwood flooring throughout the living room, hallway, and bedrooms. The spacious front room includes a pass-through to the kitchen with a custom walnut eat-in counter providing a semi-open concept layout. The white and black kitchen, which includes a back entry, has been carefully crafted with sleekness in mind. Constructed by hand in the last few months, the unique countertop and backsplash showcases handmade, white shaker cabinets (soft-close), new crisp black hardware and appliances by Whirlpool and GE. The bedrooms receive plenty of light as well as layout flexibly. The bathroom features Carrera marble tiles and a dimmable, illuminated medicine cabinet with an internal outlet for charging devices. A Grohe faucet and pedestal sink are also present. A bidet attachment with warm and cold water control adds extra appeal. Need more storage? The basement includes two storage closets, an additional storage area plus the a personal GE washer and dryer. Schedule a tour today!

5865 N Elston Avenue Unit #2S, Chicago

$655,000

4 Beds ⋅ 2 Baths ⋅ 12751659 MLS ⋅ ACTIVE Status

EXCEPTIONAL 2-FLAT | UPDATED UNITS | FLEXIBLE LIVING | INCOME POTENTIAL Beautifully maintained and thoughtfully updated, this versatile 2-flat offers an excellent opportunity for an owner-occupant, multi-generational household, or investor. Situated on a quiet residential street, the property features two, 2-bedroom, 1-bathroom units, each with updated kitchens, modern fixtures, comfortable living spaces, and the convenience of in-unit laundry. The enclosed rear stairwell leads to a well-maintained backyard, providing an outdoor space for entertaining, relaxing, gardening, or enjoying the outdoors. The basement offers additional flexibility with an in-law-style living area that can be used for extended family, guests, a home office, or potentially additional rental use, subject to applicable zoning and municipal requirements. Conveniently located near bus transportation with connections toward the Blue Line and close to a forest preserve offering walking trails, green space, and outdoor recreation. Whether you're looking to live in one unit and rent the other, accommodate extended family, or add a versatile property to your investment portfolio, this 2-flat offers updated living spaces, separate laundry, outdoor space, and multiple possibilities. A well-maintained multi-unit property with the flexibility today's buyers are looking for. Schedule your showing today!

5631 N Parkside Avenue, Chicago

$585,000

4 Beds ⋅ 2 Baths ⋅ 12751624 MLS ⋅ ACTIVE Status

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.

4855 N Mcvicker Avenue, Chicago

$460,000

3 Beds ⋅ 1 Baths ⋅ 12751726 MLS ⋅ RE-ACTIVATED Status

Beautifully Updated 3-Bedroom Home in Jefferson Park. Welcome home to this beautifully rehabbed 3-bedroom home, thoughtfully renovated in 2021 with extensive updates throughout. The main living spaces feature oak hardwood floors, while the updated kitchen offers granite countertops, stainless steel appliances, and a pantry. Each bedroom has its own closet, plus additional storage throughout the home. Major improvements include a new furnace, humidifier, A/C, ductwork, plumbing, updated electrical, windows, doors, and light fixtures. Outside, enjoy new tuckpointing, soffit, siding, gutters, sidewalks, landscaping, and fencing, plus a new 2.5-car garage with an 8-foot door. So many updates have already been completed-just move in and enjoy! A must-see! Schedule your showing today!

5440 N Mobile Avenue, Chicago

$863,900

5 Beds ⋅ 4 Baths ⋅ 12749829 MLS ⋅ ACTIVE Status

Welcome home to 6100 N. Mason. This jumbo mission style bungalow located in South Edgebrook, has been meticulously maintained and updated by the current owners. Situated on an oversized corner lot and really shows pride of ownership throughout. This 5 bedroom 3 1/2 bath home is bursting with natural sunlight. The first floor features a large cooks dream updated eat-in kitchen, with 42" custom cherry cabinets, all high end stainless steel appliances, counter top TV, granite countertops, an instant hot and filtered cold water faucet, beautiful tiled backsplash and a breakfast bar. You'll also find a beautifully updated full bath, large living room, separate large dining room and 3 bedrooms. On the second floor you'll find the large primary suite with a spa-like updated full bath, another bedroom, a powder room and a 2nd laundry room with a Bosch W/D. The full walkout basement truly expands your living space with a large family room with a wet bar, a recreation room, a large laundry room, utility/storage/workshop room and a bonus hot tub room. The fully fenced backyard will give so much enjoyment with the large composite deck with a Sunsetter retractable awning, above ground pool, a shed for storage and an extra large brick paver patio. And you won't have to cut the grass in the large back yard. It's low maintenance turf. This is more than just a home. It's a rare opportunity to live in one of Chicago's most desirable communities.

6100 N Mason Avenue, Chicago

$489,900

4 Beds ⋅ 2 Baths ⋅ 12751322 MLS ⋅ PRICE CHANGE Status

Charming Jefferson Park on a quiet tree line street- 4 bedroom 2 baths brick bungalow located one block from Farnsworth elementary school. Good size living room and separate dining room, hardwood floors throughout. two bedrooms on 1st floor and two bedrooms on 2nd floor. Lower level is totally renovated with a newer contemporary kitchen with shaker style cabinets and newer appliances - fantastic space for the older chiild that move back in or out of town guest or extra fun space for yourself (exterior door that exits to yard), finish lower level with drywall, lighting , heat, modify flooring and windows (bsmt area). Lower level has a front family rm, full bath with a shower, and 5th bdrm, / office plus a laundry area (separate area from finish area, great for privacy). fence yard with a 2 car detached garage. garage exit is very close to street perfect for snowy winters to get out to street. Heating system have new copper plumbing pipes and pump, newer hot water tank , circuit breakers with new a electric main and some new wiring.. Home is near transportation ( metra ,bus, blue line train), forest preserve and stores all nearby. wonderful location to get around with Elston ave that angle back into the inner city. lovely neighborhood to take a walk , walk the dog or cat, bike ride through the neighborhood, a very comfortable neighborhood to grow your family or yourself into. 2 REFRIGATORS AND 2 STOVES, 1WASHER & 1DRYER. Wonderful opportunity to renovated 1st floor kitchen and bath to your taste while using lower level kitchen and bath during renovations.

5325 N Linder Avenue, Chicago

$549,900

4 Beds ⋅ 4 Baths ⋅ 12750123 MLS ⋅ ACTIVE Status

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 work-from-home setups. Location is the core value here: situated minutes from the I-90/Kennedy Expressway, Metra, and CTA Blue Line, commuting across the city or to O'Hare is straightforward. For recreation and dining, you are steps from Jefferson Memorial Park, Frank J. Wilson Park, and the surrounding local spots along Milwaukee and Higgins Avenues.

5137 N Menard Avenue, Chicago

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