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$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
$295,000
2 Beds ⋅ 2 Baths ⋅ 12754394 MLS ⋅ ACTIVE 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
$230,000
3 Beds ⋅ 2 Baths ⋅ 12754215 MLS ⋅ CONTINGENT 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
$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
$535,000
4 Beds ⋅ 2 Baths ⋅ 12733038 MLS ⋅ CONTINGENT Status
Welcome to 5302 N Luna Ave, a well-maintained two-flat located on a quiet, tree-lined street in highly desirable Jefferson Park. This versatile property is an excellent opportunity for an owner occupant looking to offset their mortgage with rental income or an investor seeking a solid multifamily addition to their portfolio. Both units offer comfortable layouts with beautiful hardwood floors, stainless-steel appliances, spacious kitchens, and updated bathrooms. Each unit features its own furnace and central air system, providing separate mechanicals and added convenience. The property also features separate water heaters, upgraded electrical panels, newer windows, roof, and multiple exterior decks. The full basement provides additional storage and utility space and includes separate laundry areas with two washers and two dryers, along with dedicated storage for each unit. Outside, enjoy a fenced-in yard and an oversized detached 2+ car garage-an excellent feature for additional parking, storage, or workspace. Situated on a 30 x 125 lot, the property offers plenty of outdoor space while maintaining a convenient urban location. Ideal location for city workers. Located near schools, shopping, dining, public transportation, major roadways, and the expressway, this property combines neighborhood charm with everyday convenience. Whether you're looking to live in one unit and rent the other or add a turnkey multifamily property to your investment portfolio, 5302 N Luna Ave is an opportunity you won't want to miss.

5302 N Luna Avenue, Chicago
$650,000
6 Beds ⋅ 3 Baths ⋅ 12565108 MLS ⋅ CONTINGENT Status
Pride of Ownership. Well-maintained multi-unit property located on a quiet tree-lined street within Chicago's Portage Park/Jefferson Park corridor. This multifamily building sits on an oversized 35' x 125' lot. Each unit features a three-bedroom, one-bath layout. Hardwood floors throughout the first floor living, dining, and bedrooms. 2nd Flr features original hardwood floors beneath wall-to-wall carpeting.2nd Flr Kitchen Linoleum Tiles. Enclosed porches provide additional space suited for an office or a variety of additional uses. Plenty of closet capacity and storage options. Building amenities include coin-operated laundry in the basement, Three Separate Storage RoomsThe oversized lot affords a rear yard for gardening and recreation. Property includes a full two-car garage with a side drive for a third vehicle. Prime location provides excellent access to transportation, including the Jefferson Park and Montrose Blue Line stations and Metra stops, and the Jefferson Park CTA Depot. Easy access to I-90/94 for easy travel to O'Hare or downtown. Located near parks, shopping, and neighborhood amenities. Two leases are month-to-month. First floor is vacant. Current rents are well below market, and the area supports significantly higher rental rates. ROOF 9YRS FURNACES 2 YEARS NEW.

5048 W Agatite Avenue, Chicago
$249,999
2 Beds ⋅ 1 Baths ⋅ 12745325 MLS ⋅ ACTIVE Status
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, while the generously sized primary bedroom features two double-door closets for excellent storage. Additional conveniences include an interior storage unit, separate bike storage shed, and laundry within the building. An amazing park located just behind the building provides even more outdoor space to enjoy. Situated on a quiet residential street with convenient access to Wilson Park, Jefferson Park, Portage Park, the Jefferson Park Library, Metra, CTA Blue Line, shopping, dining, and major transportation routes. If you're looking for a place to call home, this well-located, investor-friendly condo is ready for its next owner!

5312 W Windsor Avenue Unit #2W, Chicago
$579,999
4 Beds ⋅ 3 Baths ⋅ 12744009 MLS ⋅ ACTIVE Status
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 bedrooms and 1 bathroom with hardwood floors throughout, a bright and spacious living room that flows into a separate dining room, and a well-appointed kitchen with an eat-in breakfast area. This unit also includes central heating and air conditioning, providing year-round comfort. The second-floor unit features 1 bedroom and 1 bathroom with 9-foot ceilings. All wood floors throughout the first/Second floor. The layout includes a large living room, separate dining room, and a spacious kitchen with a walk-in pantry, along with a generous bedroom featuring a large walk-in closet. The finished basement offers additional living, recreation, or storage space and includes shared laundry and mechanicals, including the furnace, A/C, and water heater. Basement features full bedroom and bathroom. Significant exterior improvements include a newer roof, windows, siding, 2 car garage, concrete patio, and privacy fence, creating a low-maintenance investment with appealing outdoor space. Located in the heart of Jefferson Park, the property offers exceptional access to transportation and neighborhood amenities, including nearby **CTA Blue Line stations and multiple Metra lines for easy commuting to downtown Chicago. Residents are also within walking distance to everyday conveniences such as Mariano's, Target, and Starbucks, with quick access to Interstate 90 and Interstate 94. Jefferson Park is known for its strong rental demand, neighborhood charm, and unmatched transit connectivity, making this property an excellent choice for investors seeking steady income or buyers looking to live in one unit while generating rental income from the other. Home has a 2 car garage and parking pad next to garage. Fully fenced in yard. Click on 3d tour to walk though unit. 1st floor unit availabe for owner occupancy now. Do not miss this chance to live and have others pay your mortage!

5037 W Winona Street, Chicago
$245,900
2 Beds ⋅ 2 Baths ⋅ 12740997 MLS ⋅ ACTIVE Status
This gorgeous 2bedroom, 1.5bathroom condominium features a private balcony in the heart of Chicago's highly sought-after Jefferson Park neighborhood. Located on the second floor, the home offers a versatile layout with plenty of space to relax and entertain. Both bedrooms include generous closet space; the primary bedroom has its own .5 bathroom, while the second bedroom is ideal for a home office or guest room. Large windows throughout the unit bring in abundant natural light. The kitchen comfortably fits a dining table and includes convenient in unit laundry. parking spot #17 HOA Fee includes one assigned parking space, heating, cooking gas, trash pickup, snow removal, storage, and water. Situated in one of Chicago's most prized neighborhoods, this lovely home offers easy commuting throughout the city and beyond, along with access to Jefferson Park's vibrant activities

4835 N Central Avenue Unit #212, Chicago
$197,000
1 Beds ⋅ 1 Baths ⋅ 12718374 MLS ⋅ CLOSED Status
Spacious, sun-filled 1-bedroom corner unit on the third floor of an elevator building. This freshly painted home features a recently updated kitchen with white shaker cabinets, newer countertops and appliances, plus a brand-new Pella kitchen window. New carpeting has been installed throughout the living room and bedroom. The building offers ample parking, with convenient laundry and storage rooms located on the first floor. The low HOA fee includes heat, air conditioning, cooking gas, and water-you are responsible for electricity only. Ideally located with easy access to bus routes, the Blue Line, Metra, and I-90. Truly move-in ready! Pleasure to show! Rentals are allowed, but there is a rental cap and it has been reached. There is a waiting list.

5915 W Gunnison Street Unit #3E, Chicago
$199,900
1 Beds ⋅ 1 Baths ⋅ 12719391 MLS ⋅ ACTIVE Status
Charming, freshly painted 1 bedroom, 1 bath condominium in the heart of Jefferson Park. This well maintained unit features a private balcony overlooking the courtyard and is situated toward the back of the courtyard for added privacy. This unit offers storage throughout, an additional private storage space in the basement, one assigned parking space, and convenient on site laundry facilities. Ideally located with easy access to I-90, I-94, public transportation, and a variety of dining and everyday amenities. A wonderful opportunity to own a move in ready unit in a convenient location.

5024 N Austin Avenue Unit #2E, Chicago
$575,000
5 Beds ⋅ 3 Baths ⋅ 12711245 MLS ⋅ CLOSED Status
Longtime owner offers this classic checkerboard two flat in super desirable Jefferson Park! Main floor unit features 3 beds and 1 full bath with large living room with crown molding, formal dining room with original woodwork and coved moldings throughout with nearly 9 ft ceilings (hardwood flooring under carpet)! Lots of windows (all 4 sides) and natural sunlight! 3 nicely sized beds, 1 full bath plus kitchen with large walk in pantry! 2nd floor unit features 2 beds and 1 full bath with with large living room, formal dining room plus large oversized kitchen with all appliances and pantry! Large back porch too! Full basement with 1/2 bath plus laundry room! Exterior features large patio overlooking well maintaned pine tree and garden area! 2 car detached garage! Great location...just steps to the blue line, minutes to the expressway and 10 minutes to the airport! Immediate possession if needed. Roof @ 10 yrs old and refurbished front stoop. Priced under recent appraisal...sold in as is condition! Opportunity is knocking!!

4933 W Ainslie Street, Chicago
$234,000
2 Beds ⋅ 1 Baths ⋅ 12708502 MLS ⋅ CONTINGENT Status
HUGE PRICE REDUCTION - - - 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 atmosphere throughout. Step outside to your generously sized private balcony overlooking a serene, landscaped green space. Enjoy abundant closet and storage space, thoughtfully designed for practical living. Additional highlights include heated floors throughout, assigned parking, a dedicated storage locker, and convenient coin-operated laundry in the building. Situated on a quiet, tree-lined street, this prime location provides exceptional access to transportation, including the Jefferson Park Blue Line, CTA hub, and Metra, along with quick connectivity to I-90/94, offering effortless travel to O'Hare and downtown Chicago. Short distance to 3 city parks, shopping, and neighborhood amenities, this is a rare opportunity to own a character-filled home Jefferson Park. A perfect blend of vintage charm, natural light, and unbeatable location.

5440 W Windsor Avenue Unit #3A, Chicago
$225,000
2 Beds ⋅ 1 Baths ⋅ 12691707 MLS ⋅ CONTINGENT Status
Well-maintained 2-bedroom, 1-bath condo in the heart of Jefferson Park, one of Chicago's fastest-growing and most desirable neighborhoods. This move-in-ready home features hardwood floors in the living room, hallway, and both bedrooms, new windows, a remodeled bathroom, a newer furnace, and a new rear entry door. A standout feature is central air conditioning-this is the only unit in the building with central A/C. The building offers common laundry along with a private storage unit in the basement. The association covers water, lawn maintenance, snow removal, garbage, recycling, and common insurance. Located with easy access to the Kennedy Expressway, public transportation, parks, restaurants, and shopping, this home offers the perfect combination of modern updates and everyday convenience.

5148 N Monitor Avenue Unit #303, Chicago
$399,900
4 Beds ⋅ 3 Baths ⋅ 12693972 MLS ⋅ RE-ACTIVATED Status
"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 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
$262,000
2 Beds ⋅ 2 Baths ⋅ 12669766 MLS ⋅ CLOSED Status
**MULTIPLE OFFERS RECEIVED, HIGHEST AND BEST OFFERS DUE BY THURSDAY, JULY 2nd at 12PM CST** Spacious, well-maintained, and full of everyday convenience, this 2-bedroom, 2-bath condo in Jefferson Park offers the kind of living space, storage, and parking that can be hard to find in the city! This second-floor home features beautiful hardwood floors, generous room sizes, a private balcony, garage parking, extra storage, and plenty of natural light throughout. Whether you are hosting friends, working from home, or enjoying a quiet night in, the layout feels comfortable, functional, and easy to live in. The oversized kitchen is a major highlight, offering abundant cabinet and counter space, plenty of room to gather, and an easy flow which opens up into the living and dining areas. The primary bedroom suite features an en-suite full bath with a walk-in shower and a large closet, while the second bedroom and additional full hall bath offer excellent flexibility. Use the extra bedroom as a guest room, home office, workout space, media room, or whatever best fits your lifestyle. Looking to relax and enjoy the outdoors after a long day at work? Step out on your private balcony just off the living room and read your favorite book or sip on a drink to unwind. Love to entertain and have company? Parking will never be a concern in this unit! With one designated parking space in the attached garage, an additional exterior parking space, and plenty of guest parking located behind in the lot the building, parking is always a breeze. Storage is another major perk of living in the building. With a full basement shared by residents, and an additional dedicated storage room for the unit, this unit offers the kind of extra space you rarely find living in a condo! Recent updates include HVAC, dishwasher, oven, fire alarm, and smart thermostat, giving buyers added peace of mind. Additional highlights include in-unit laundry, ceiling fans, and all major appliances that stay. With affordable HOA fees, a prime Jefferson Park location, a great layout, plenty of parking and storage, and so many everyday conveniences, this condo is a wonderful opportunity for anyone seeking comfortable, low-maintenance city living. Close to great shopping, dining, public transportation, Jefferson Park pool and Memorial Park, expressways, and O'Hare Airport, this home offers the accessibility and ease you've been looking for. Don't miss out on this incredible opportunity to own a beautiful home in a coveted location!

5624 W Higgins Avenue Unit #2S, Chicago
$365,000
3 Beds ⋅ 2 Baths ⋅ 12685578 MLS ⋅ CLOSED Status
Welcome Home! Experience pristine top-floor living in this exceptionally well-maintained, investor-friendly building right in the heart of Jefferson Park. Flooded with natural light from expansive windows and stunning skylights, this rare three-bedroom, two-full-bathroom home boasts a cozy gas fireplace and a seamless open-concept kitchen complete with stainless steel appliances and abundant cabinet space. The massive, spa-like primary bathroom serves as your private retreat, featuring a long dual-vanity sink, a walk-in shower, and a luxurious Jacuzzi tub. Step directly from the primary bedroom out onto your own private top deck-a highly coveted outdoor perk that is perfect for entertaining, grilling, or just relaxing. Combining low HOA fees with all your must-have amenities, including in unit laundry, and an extra storage closet in the basement, this turnkey property truly has it all with a healthy association to match. This rare gem is not going to last long, so come by and see this incredible space in person before it is gone.

5617 W Lawrence Avenue Unit #3, Chicago
$240,500
2 Beds ⋅ 2 Baths ⋅ 12679411 MLS ⋅ CLOSED Status
NICE 1ST FLOOR UNIT, OPEN FLOOR PLAN, EAT IN KITCHEN, LIVING & DINING ROOM COMBO WITH SLIDING DOORS TO BALCONY, MASTER BEDROOM HAS BATH W/SHOWER, BASEMENT WITH LAUNDRY & STORAGE, ONE ASSIGNED PARKING SPOT, CLOSE TO JEFFERSON PARK BLUE LINE. BRAND NEW REFRIGERATOR AND STOVE. FURNACE AND A/C INSTALLED NEW 11/2025. VACANT AND EASY TO SHOW

5819 W Higgins Avenue Unit #1D, Chicago
$325,000
2 Beds ⋅ 2 Baths ⋅ 12682591 MLS ⋅ CLOSED Status
Solid 2 bedroom, 2 bathroom condominium in an elevator building offers all the bells and whistles you've been looking for including desirable in-unit laundry closet and spacious private balcony. In 2025 the home underwent a renovation with both the bathrooms fully remodeled from the studs, new molding and trim was put in throughout the home, the electrical outlets, switches and chandeliers were put in, new bedroom and closet doors, freshly painted and new balcony tiles. 2021 kitchen appliances. In 2016 new windows were put in the entire building. Assessment fees include water, gas, heat, garage parking (#19), storage unit (#19), common area insurance, exterior maintenance, lawn care, scavenger, and snow removal. This beautifully updated condo is move in ready. Enjoy Chicago's historic Portage Park neighborhood with its 36-acre Portage Park at its center, revitalizing Six Corners commercial district, restaurants and so much more! Per Condominium Association Rules and Regulations no pets are allowed.

6300 W Montrose Avenue Unit #305, Chicago
$522,500
5 Beds ⋅ 3 Baths ⋅ 12673635 MLS ⋅ CLOSED Status
Bright and sunny Dutch Colonial two-unit building with an in-law unit in Portage Park on an oversized lot. Each unit offers 2 large bedrooms divided by updated bathrooms with an in-law suite in the basement that includes a flexible one bedroom/studio with a seperate bathroom and living room. The property now includes modern heating and cooling systems in all three living areas including ductwork. Unit 1 had additional updates including beautiful hardwood and subfloors, a new bathroom (including tile, floor, toilet, sink and lighting), dishwasher added to the kitchen and was painted in April 2026. Excellent care has been taken over the years including exterior work on the porch and adding a new front and back gate. There are two hookups for laundry in the basement and 1 washer and dryer are included in the sale. The building has a beautiful backyard ideal for entertaining and pets. This is an ideal house hacker or any first time investor looking to live for pennies. Location has strong long term income potential in charming Portage Park close to restaurants, bars, shopping and many cute neighborhood parks.

5725 W Giddings Street, Chicago
$475,000
3 Beds ⋅ 3 Baths ⋅ 12671001 MLS ⋅ CLOSED Status
Motivated Seller!!! Will consider all offers!!! 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 dedicated laundry room adds everyday convenience for tenants. The property also includes a solid brick two-car garage, offering excellent potential for additional rental income. Unit 2 is currently leased at $1200 per month through November 2026, providing immediate and stable cash flow. This is an excellent opportunity for a flipper's dream or owner-occupants seeking a prime location with strong upside. Additionally, the garden unit offers an additional bedroom, a full bathroom, a full kitchen, and two points of entry from the side and rear of the unit.

5552 N Major Avenue, Chicago
$695,000
6 Beds ⋅ 3 Baths ⋅ 12664676 MLS ⋅ CLOSED Status
Welcome to this meticulously maintained two-unit brick building in one of Chicago's most sought-after Northwest Side neighborhoods. Located on a peaceful cul-de-sac this home offers the perfect mix of comfort, convenience, and community. Both units are freshly painted, sparkling clean, and move-in ready, featuring beautiful hardwood floors throughout the first and second levels, central HVAC, and impressive updates. The first-floor kitchen boasts all-new countertops and backsplash, while both bathrooms have been renovated with heated floors. A brand-new roof was installed in the spring of 2024, hot water heaters were replaced in 2020, and the building is equipped with two Generac generators for reliable backup power. Additional highlights include a convenient enclosed back porch and custom built-ins for extra storage, a dedicated laundry room, ample storage space throughout the building, and a detached 2-car garage with extra cabinetry. The lower level offers excellent potential for an in-law suite or additional living space. Ideally situated for both owner-occupants and investors, this property is just minutes from the Jefferson Park Blue Line and Metra stations, easy access to the 90/94 expressway, HIP shopping center, Ridgemoor Country Club, and Wilbur Wright College. Excellent schools, parks, and neighborhood amenities are all right at your doorstep just a half-block from Dunham Park with its tennis courts, playgrounds, and recreation. This is a rare opportunity to own a well-cared-for, updated two-flat in a highly desirable Jefferson Park location. Don't miss out - schedule your showing today!

6122 W Leland Avenue, Chicago
$239,900
2 Beds ⋅ 1 Baths ⋅ 12658378 MLS ⋅ CLOSED Status ⋅ Jefferson Court Townhomes BLDG.
*INVESTOR FRIENDLY*. Beautifully maintained 2-bedroom condo with a versatile bonus tandem room in the highly sought-after **Jefferson Park neighborhood**! This well-designed unit offers an efficient layout with great natural light, a cozy fireplace, and flexible living space perfect for a home office, nursery, or workout area. The kitchen features 42" cabinets along with newer stainless steel stove and refrigerator (2024). Additional updates include a new water heater (2026), and in-unit laundry. Enjoy the convenience of 1-car garage parking plus a spacious full-size storage unit. Located just minutes from the Jefferson Park Metra and CTA transit hub, this home is a commuter's dream with quick access to I-90/94, downtown Chicago, O'Hare, restaurants, shopping, parks, and neighborhood favorites. A fantastic opportunity to own in one of Chicago's most connected and desirable neighborhoods. Schedule your private showing today!

5418 W Windsor Street Unit #1N, Chicago
$662,000
6 Beds ⋅ 3 Baths ⋅ 12655153 MLS ⋅ CLOSED Status
Decades of prideful ownership, consistent upkeep, and proactive maintenance are evident in this exceptionally well-cared-for multi-unit property located on a quiet, tree-lined street. Perfectly positioned within Chicago's sought-after Mayfair/Portage Park/Jefferson Park corridor, this multifamily opportunity sits on an oversized 35' x 125' lot, offering expanded outdoor living and future flexibility. Each unit features a desirable 2-bedroom, 1-bath layout. The 1st and 2nd floor residences showcase sun-filled interiors, expansive living rooms, separate formal dining areas, and natural hardwood flooring extending throughout the living/dining spaces and bedrooms. Enclosed rear porches provide versatile flexible areas well-suited for a home office, den, storage, or a variety of additional uses. The second-floor unit also includes a front balcony, creating another private outdoor retreat. Abundant closet capacity and storage options add further functionality throughout the building. Separate HVAC systems and individual hot water tanks for each unit provide efficiency. Building amenities include coin-operated laundry in the basement along with dedicated storage areas for each residence. Major improvements include heating mechanicals and garage roof all 10 years old or newer, central air conditioning replaced in 2022 and 2024, and flood control system installed in 2024. Long-term ownership is reflected in the continued care and ongoing significant investments made throughout the years. The oversized lot further enhances the property with an expansive side/rear yard for gardening, entertaining, recreation, or future possibilities. Rounding out the exterior is a full 3-car garage.This prime location provides excellent access to transportation including the Jefferson Park and Montrose Blue Line stations & Metra stops, Jeff Park CTA depot, and convenient access to I-90/94 for easy travel to O'Hare and downtown Chicago. Located near parks, shopping, dining, and neighborhood amenities, this is a rare opportunity to own a solid, well-maintained building with decades of attentive ownership in an exceptionally convenient location. Your clients will not be disappointed. 2 leases are MTM, other expires in August.

5041 W Agatite Avenue, Chicago
$470,000
3 Beds ⋅ 2 Baths ⋅ 12649719 MLS ⋅ CLOSED Status
MULTIPLE OFFERS RECEIVED, BEST AND FINAL MONDAY 5/25 AT 5PM. Rarely available top-floor deluxe 3BR/2BA residence in the private and serene Eastwood Plaza, a boutique elevator building located in Jefferson Park. This beautifully renovated home offers over 1,800 square feet of thoughtfully designed living space and an exceptional open-concept layout. Completely renovated throughout, the unit features a spacious living, dining, and kitchen area created by removing a dividing wall for seamless flow. Boasting unique finishes and custom and high-end updates throughout the kitchen, baths, and living room, the stunning kitchen showcases stone countertops, an impressive 12-foot L-shaped island, a custom backsplash, stainless steel appliances with hood, and an impressive 4-foot skylight offering great natural light. The kitchen opens directly into the dining and living areas, highlighted by a custom built-in entertainment center, shelving, a striking fireplace feature wall, and access to an expansive 16-foot balcony with peaceful treetop views. Additional updates include all new flooring throughout, radiant floor heating, two generously sized secondary bedrooms, a beautifully renovated full bath, and a dedicated laundry room with side-by-side washer and dryer. The oversized primary suite offers a true retreat with a spa-inspired bath featuring a soaking tub, separate tiled shower with a shaving nook, and a spacious walk-in closet. Two heated garage parking spaces-a true luxury to have for cold Chicago winters-and additional storage are included. Ideally situated in a highly walkable location close to shopping, CTA transportation, and numerous restaurants. No rentals or pets permitted.

6050 W Eastwood Avenue Unit #309, Chicago
$430,000
3 Beds ⋅ 2 Baths ⋅ 12647041 MLS ⋅ CLOSED Status
Beautifully maintained 3 bedroom, 2 bath condo in a desirable elevator building in Jefferson Park. Owned and meticulously cared for over the past 22 years, this spacious residence offers a functional open concept layout with generous room sizes, abundant natural light, and hardwood floors throughout the main living areas. The expansive living and dining space features a cozy gas fireplace and flows seamlessly to both front and rear private balconies, providing excellent indoor outdoor living and plenty of space to relax or entertain. The large kitchen offers ample cabinetry, a breakfast bar, and opens directly into the main living area for easy everyday living. The primary suite includes a private bath with double vanity, jacuzzi tub, separate shower, and access to a private balcony. Additional highlights include in-unit laundry, large storage room, and garage parking. Ideally located just steps from parks, coffee shops, grocery stores, restaurants, the Metra, Blue Line, and expressway access, this move-in ready home combines space, convenience, and pride of ownership in one exceptional package.

5362 W Lawrence Avenue Unit #2W, Chicago
$365,000
2 Beds ⋅ 2 Baths ⋅ 12648946 MLS ⋅ CLOSED Status
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 living/great room with a cozy wood-burning fireplace and access to a large private terrace make this home ideal for both relaxing and entertaining. The primary bath has been tastefully refreshed with marble finishes, and additional updates include newer in-unit laundry and a brand new HVAC system (2025). Parking and extra basement storage are included. Rarely found with condo living, enjoy a shared grassy backyard perfect for BBQs, pets, or playtime. Unbeatable location close to the Jefferson Park Terminal, Metra, Blue Line, restaurants, shopping, and expressways. Incredible value!

5691 W Higgins Avenue Unit #2W, Chicago
$525,000
3 Beds ⋅ 3 Baths ⋅ 12628249 MLS ⋅ CLOSED Status
Step into timeless elegance at 5042 W Winnemac Ave, a meticulously renovated all-brick 1929 Jefferson Park 2-flat that masterfully fuses historic charm with contemporary luxury. This property is a rare gem, offering two distinct units that cater to both multi-generational living and investment opportunities. Every detail has been thoughtfully designed to create a harmonious blend of historic character and modern convenience. First-Floor Duplex-Down (Unit 1) The main level and fully reimagined lower level of Unit 1 provide a sophisticated sanctuary with 2 bedrooms and 2 baths. The living room, featuring custom built-ins and freshly painted walls, exudes warmth and charm. Gleaming hardwood floors flow throughout the first floor, which also includes a versatile exercise room that can double as a private office. The gourmet kitchen is a chef's dream, complete with granite countertops, stainless steel appliances, and crisp white cabinetry that enhances the bright and airy feel of the space. The first-floor bathroom features a tub and shower combo, an updated vanity, and a modernized design. The fully renovated basement bathroom offers a luxurious glass-enclosed shower with subway tile and a sleek, contemporary aesthetic. The fully renovated lower level also boasts new laminate vinyl plank flooring and features a spacious family room and additional living space. Step outside to your private yard oasis, perfect for entertaining or relaxing, and enjoy the convenience of in-unit laundry. Attic Penthouse (Unit 2) Unit 2 is a light-filled 1-bedroom, 1-bath penthouse that combines charm and functionality. The eat-in kitchen features white cabinetry, butcher block countertops, and a stainless steel stove, creating a clean and modern aesthetic. While hardwood floors are found in several rooms, the hallway and kitchen feature alternate flooring for added practicality. The bathroom is a serene retreat, complete with a soaker tub, elegant millwork, and white cabinetry. The convenience of a washer/dryer combo enhances everyday living, making this unit as versatile as it is beautiful. Located in the prestigious Jefferson Park neighborhood, this property offers unparalleled convenience for commuters and city explorers alike. The home is just a short walk to the Jefferson Park Transit Center, providing access to the Blue Line train, Metra rail, and multiple bus routes, making travel to downtown Chicago and beyond a breeze. For drivers, the property is ideally situated near the Kennedy Expressway (I-90) and the Edens Expressway (I-94), offering quick and easy access to major highways. Whether you're heading to O'Hare International Airport, downtown Chicago, or the suburbs, this location ensures seamless connectivity. The 2-car garage is a standout feature, with its very tall ceilings that can easily accommodate a work van or truck, making it ideal for professionals or those with larger vehicles. The property is equipped with dual furnaces (2018/2005) and a 2015 water heater, ensuring comfort and efficiency year-round. This property is a true masterpiece, offering a unique opportunity to own a home that combines historic charm, modern updates, and exceptional functionality. Whether you're seeking a luxurious multi-generational home or a prime investment property, 5042 W Winnemac Ave delivers on every level. Don't miss your chance to experience the pinnacle of refined living, schedule your private showing today.

5042 W Winnemac Avenue, Chicago
$740,000
8 Beds ⋅ 3 Baths ⋅ 12621770 MLS ⋅ CLOSED Status
Beautifully updated 3-flat located in the highly desirable Jefferson Park neighborhood of Chicago. Each unit offers three spacious bedrooms, modern finishes including granite countertops throughout, and updated shaker cabinetry. Enjoy the convenience of in-unit laundry in every apartment, along with central heating and air. The property also features a shared rear deck with ample street parking is readily available. Ideally situated just minutes from Harlem Irving Plaza, offering easy access to shopping, dining, and everyday conveniences. Don't miss this great property before it's gone! HIGHEST AND BEST DUE 4/20/2026 AT 1PM.

6030 W Lawrence Avenue, Chicago
$210,000
1 Beds ⋅ 1 Baths ⋅ 12606675 MLS ⋅ CLOSED Status
* Check out the video & the 3D walk-through of this home * Stunning & cozy 1 bedroom, 1 bathroom top-floor condo in desirable JEFFERSON PARK location! This remodeled 2nd-floor condo overlooks the tree-lined street and has the perfect mix of vintage charm & modern updates. This one-bedroom unit is not your traditional small unit; it's the size of a two-bedroom unit. Step into this unit and enjoy the extra-wide, open living room with hardwood floors throughout & large southwest-facing windows that bring in lots of natural light. Condo living at its best, with a brand new kitchen featuring stainless steel appliances, timeless shaker-style cabinetry, backsplash with custom tilework, granite countertops, breakfast bar, and a charming private deck off the separate dining room that is perfect for grilling, relaxing, entertaining, or watching your plants grow. The remodeled bathroom features a modern look, high-quality finishes, and a large shower with custom tilework. Generously sized primary bedroom with ample closet space and gets great light. The unit has ample storage, plus an additional large private storage closet, a common laundry room, and a bike room in the basement. Completely remodeled in 2025, this impeccable home features meticulous attention to detail. Recent updates include: new kitchen cabinets, countertops, backsplash, hardware, and appliances (2025), new bathroom remodel, tile, shower glass, toilet, plumbing fixtures, vanity, and mirror (2025), new paint throughout the unit (2025), new fans and light fixtures (2025), refinished hardwood floors (2025). Please ask your agent for the full list of improvements to the unit and the building. Low HOA assessment of $285 per month includes heat, water, hot water, common insurance, exterior maintenance, lawn care, garbage, & snow removal. Easy permit street parking. Proactive association with approx. $13,786 in reserves. Converted to condos in 2001. All BRICK building. 8 total units, 6 owner-occupied, 2 rentals. Rentals allowed (Owner must occupy the unit for 12 months prior to renting. No short-term rentals). Cats & dogs allowed (No breed or weight restrictions. No pets allowed for renters). Fall in love with all Jefferson Park offers - Easy access to transit (Blue Line, Metra, & bus stops), 90/94 expressway, popular restaurants/bars/retail, coffee shops, and green space. Welcome home! MULTIPLE OFFERS RECEIVED. Please submit highest & best by Monday 04/06 @ 11 am.

4941 N Lester Avenue Unit #4, Chicago



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