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5338 W Montrose Avenue, Chicago
$1,195,000
9 Beds ⋅ 6 Baths ⋅ 12775394 MLS ⋅ ACTIVE Status
Old Irving/Portage Park! Fully Remodeled three unit! This ideal Owner-Occupier is offering three spacious 3-bedroom, 2-bathroom apartments! The stylish kitchens feature sleek quartz countertops, a full-height backsplash, and a stainless steel appliance package including a dishwasher and microwave. Spacious bedrooms comfortably accommodate queen- or king-size furniture, while two beautifully updated bathrooms feature modern finishes and spa-inspired walk-in showers. Bonus updates include recessed lighting, New windows, new water heaters, new boiler, modern light fixtures, and numerous additional updates throughout the building. Residents have access to free laundry in the basement, a shared patio, and plenty of space to make themself at home. Ideally located near Portage Park's beautiful parks, neighborhood shops, restaurants, cafes, and public transportation, this apartment offers the perfect blend of modern updates, space, and convenience. Two car garage.

5338 W Montrose Avenue, Chicago
5759 N Elston Avenue, Chicago
$769,000
8 Beds ⋅ 5 Baths ⋅ 12777301 MLS ⋅ ACTIVE Status
Updated legal 2-flat in Jefferson Park with a finished English Garden Unit. Both legal units feature 3 bedrooms, 1.5 baths, spacious layouts with separate dining areas and additional kitchen dining space, recessed lighting, and updated kitchens with quartz countertops, stainless steel appliances, and ample cabinetry. Unit 1 is leased for $2,650/month and Unit 2 for $2,400/month, generating $5,050/month or $60,600 annually. Unit 1 rent includes electricity, gas/heat, water, trash, landscaping, and one garage parking space. Unit 2 rent includes electricity and water. The finished basement is currently vacant and offers 2 bedrooms and 1 full bath, with estimated rental potential of approximately $2,300/month, subject to applicable laws, zoning, approvals, and permitted use. If legally approved for rental use, potential gross income could reach approximately $7,250/month or $87,000 annually. 2024-2025 improvements include a new roof and windows, updated kitchens and bathrooms, tuckpointing, and improvements to the garage-top deck. Additional features include rear decks, shared outdoor space, and coin-operated laundry. Conveniently located near shopping, dining, transportation, parks, and neighborhood amenities. Excellent opportunity for an investor, owner-occupant, or multi-generational household.

5759 N Elston Avenue, Chicago
5236 W Montrose Avenue, Chicago
$740,000
6 Beds ⋅ 3 Baths ⋅ 12776241 MLS ⋅ ACTIVE Status
LARGE 2 FLAT BRICK WITH 3 BEDROOM APARTMENTS, SEMI FINISHED BASEMENT WITH FRONT ENTRANCE. HARDWOOD FLOORS THROUGHOUT, GREAT INVESTMENT OR OWNER-OCCUPIED HOME.

5236 W Montrose Avenue, Chicago
5626 N Central Avenue, Chicago
$739,000
5 Beds ⋅ 3 Baths ⋅ 12783248 MLS ⋅ ACTIVE Status

5626 N Central Avenue, Chicago
5600 N Mango Avenue, Chicago
$734,900
5 Beds ⋅ 3 Baths ⋅ 12503023 MLS ⋅ ACTIVE Status

5600 N Mango Avenue, Chicago
5122 N Lotus Avenue, Chicago
$670,000
6 Beds ⋅ 3 Baths ⋅ 12787200 MLS ⋅ ACTIVE Status
Wonderful Opportunity in the Heart of Jefferson Park! Discover the possibilities with this charming 2-flat situated on an oversized lot along a beautiful, tree-lined street in one of Chicago's sought-after Northwest Side neighborhoods. Whether you're an investor looking to expand your portfolio or an owner-occupant hoping to live in one unit while generating rental income from the other, this property offers flexibility and exciting potential. The generous lot provides additional outdoor space and opportunities to create your own backyard retreat. Enjoy the charm of an established neighborhood while being just moments away from everything you need. The location is truly a highlight! Conveniently situated near neighborhood parks, shopping, restaurants, Jewel-Osco, the CTA Blue Line, Metra, and I-90, with easy access to O'Hare International Airport. With its desirable location, oversized lot, and investment potential, this property is a wonderful opportunity to bring your vision to life and make it your own. Schedule your showings today!

5122 N Lotus Avenue, Chicago
5426 N Lovejoy Avenue, Chicago
$670,000
4 Beds ⋅ 2 Baths ⋅ 12600798 MLS ⋅ ACTIVE Status
Welcome to this Lovingly Maintained Gladstone Park Gem! Owned and cherished by the same owner-occupant for over 20 years, this two-flat at 5426 N Lovejoy shines with true pride of ownership and consistent, thoughtful updates throughout. Featuring two units with 2 bedrooms and 1 bathroom, and an additional 1 bedroom, 1 bathroom unit (non conforming) in the basement, it's the perfect opportunity for an investor or an owner-occupant seeking a move-in-ready home with built-in income. You'll be greeted by a gorgeous front porch, the perfect spot for your morning coffee. Both the first and second floors offer 2 bedrooms and 1 bathroom with bright, functional layouts. The first-floor unit includes a versatile bonus space, ideal as an office, sitting room, or additional sleeping area, along with a charming wood-burning fireplace. The finished basement features a 1-bedroom, 1-bathroom in-law suite (non-conforming), offering excellent flexibility for extended family. Enjoy immediate cash flow, with the first floor recently renting for $2,160/month (currently owner-occupied) and the second floor at $1,975/month. This building has been lovingly maintained with numerous mechanical updates over the years, including new electric and copper plumbing throughout all three units. Units 1 and 2 feature updated can lighting in the kitchens, with Unit 2 also updated in the dining area. The first- and second-floor hardwood floors have both been recently refinished. Additional conveniences include shared basement laundry for all occupants and a sump pump/flood control system for added peace of mind during rainy months. Located in a quiet, tree-lined section of the neighborhood, you're just minutes from the Blue Line, Metra, and I-90/94 - a true commuter's dream. Don't miss this rare find, where long-term pride of ownership meets modern rental demand!

5426 N Lovejoy Avenue, Chicago
5631 N Parkside Avenue, 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
5475 N Monitor Avenue, Chicago
$625,900
5 Beds ⋅ 3 Baths ⋅ 12762304 MLS ⋅ ACTIVE Status
NICE JEFFERSON PARK 2 FLAT WITH FINISHED BASEMENT! 2 OVERSIZE UNITS WITH CENTRAL AIR, THREE SEPARATE FURNACES AND HOT WATER TANKS, COPPER PLUMBING. BOTH UNITS HAVE FORMAL DINING ROOM, DEN AND SLIDING DOOR TO THE DECK! NEWER WIDOWS, NEWER 1ST FLOOR AC UNIT,TWO FURNACES AND WATER TANKS ARE NEWER TOO. 2 CAR GARAGE AND ADDITIONAL PARKING SPOT. COIN LAUNDRY. GREAT RES BLOCK! THE PROPERTY IS IN A GREAT SHAPE BUT SELLER WANTS TO SELL IT AS IS.

5475 N Monitor Avenue, Chicago
4542 N Long Avenue, Chicago
$599,000
5 Beds ⋅ 3 Baths ⋅ 12772229 MLS ⋅ ACTIVE Status

4542 N Long Avenue, Chicago
4855 N Mcvicker Avenue, Chicago
$584,999
4 Beds ⋅ 2 Baths ⋅ 12751624 MLS ⋅ PRICE CHANGE 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
5334 N Lovejoy Avenue, Chicago
$583,000
4 Beds ⋅ 2 Baths ⋅ 12779923 MLS ⋅ ACTIVE Status
Classic Chicago two-flat offering a great combination of vintage character, spacious floor plans, and income potential. Each unit features 2 bedrooms, 1 full bath, a separate living room and dining room, kitchen, and enclosed sunroom, providing generous living space and flexible room configurations. The property retains attractive original details, including hardwood floors, substantial wood trim and doors, and a distinctive stained-glass window. Large windows provide excellent natural light throughout both units. The kitchens offer ample cabinet and counter space, while the bathrooms are functional and well maintained. The full unfinished basement provides extensive storage, laundry facilities, mechanicals, and additional possibilities for the new owner. A detached two-car garage is another significant benefit-especially for a Chicago two-flat. This property provides flexibility for an owner-occupant, extended-family arrangement, or investor. Live in one unit while generating rental income from the other, or maintain both apartments as rental units. With two well-proportioned apartments, separate living and dining spaces, sunrooms, a full basement, and a two-car garage, this is a versatile property with plenty of potential. Outstanding Jefferson Park location! Enjoy the convenience of a highly walkable neighborhood with shopping, restaurants, parks and everyday amenities nearby. Excellent transportation options include nearby CTA bus service plus convenient access to the Jefferson Park Transportation Center offering CTA Blue Line, Metra and Pace service, providing easy connections to downtown Chicago, O'Hare and the northwest suburbs. Commuters will also appreciate convenient access to the Kennedy and Edens Expressways. Outdoor recreation is plentiful, with neighborhood parks, Caldwell Woods, LaBagh Woods and other forest-preserve areas nearby. This location offers an appealing combination of a residential neighborhood setting with outstanding access to transportation and city amenities. Property Highlights: Two units * 2 bedrooms/1 bath per unit * Separate living and dining rooms * Kitchen in each unit * Enclosed sunroom in each unit * Hardwood floors and vintage woodwork * Full unfinished basement * Laundry area * Detached 2-car garage * Excellent natural light. SOLD AS IS.

5334 N Lovejoy Avenue, Chicago
4923 N Mason Avenue, Chicago
$579,000
4 Beds ⋅ 3 Baths ⋅ 12793590 MLS ⋅ NEW Status
Beautiful, Legal Brick 2 Flat in the heart of Jefferson Park. Excellent building includes top floor unit 2 Bed 1 Bath. First floor unit 2 Bed 1 Bath. Bright open units each equipped with private rear porches. Pictures only reflect second floor unit but first floor is even bigger and more updated. Long time owner, solid and well maintained building. In-law arrangement with additional Bed and Bath. Excellent locations, located on a quiet street close to restaurants, shopping, parks, schools, train and highway! This home has it all! Don't miss out! HURRY!!

4923 N Mason Avenue, Chicago
5839 W Eastwood Avenue, Chicago
$579,000
4 Beds ⋅ 3 Baths ⋅ 12791975 MLS ⋅ PRICE CHANGE Status
Excellent opportunity to own this well-maintained brick 2-flat with a non-conforming 3rd unit in the basement. All units have 2 bedrooms & 1 bath! This property offers spacious layouts, good floor plans, quality updates, & excellent income potential! Special unit feature on 1sr floor include: Hardwood floors, pantry, central air & a spacious deck overlooking the yard; 2nd floor has hardwood floors, central air, spacious pantry, and a lovely enclosed porch. Additionally there are thermopane windows throughout the bldg, a nice fully fenced yard, and a large 2 & 1/2-car garage with room for lawn equipment & a workbench. Front hallway freshly painted! Entire 1st floor and basement apartments painted last summer. Major improvements include a roof in 2019 and most mechanicals recently replaced. Both hot water heaters in 2022 & 2025; 1st-floor furnace in 2022; & 1st-floor A/C in 2018. All this situated on an oversized 37' x 125' lot! Prussing School K-8 at the corner! Lovely Neighborhood Location!

5839 W Eastwood Avenue, Chicago
5484 W Gettysburg Street, Chicago
$570,000
5 Beds ⋅ 3 Baths ⋅ 12769997 MLS ⋅ ACTIVE Status
3 Total Dwelling Units Multi-Family building (legal 3 Flat with zoning RS-3 on recently issued Zoning Certificate attached in Add'l Info) on an oversized double Lot (6,250 Sq Feet) right in the heart of Jefferson Park. Attention: Rehabbers, Developers (for Value in the Land). Also, for Homeowners/Owner Occupied to live in one apartment and rent out two other units. 3 units comprise: Two smaller 2bed/1 bath apartments in divided 1st Floor. And on the 2nd Floor, one 2 bedrm/ 1 bath apartment with Living Rm/Family Rm and Dining Room. Full unfinished basement is just an open space with mechanicals and laundry room. Newer roof was installed in 2022. 2 car garage. Plus an additional rent from 3 parking spaces.

5484 W Gettysburg Street, Chicago
5102 W Sunnyside Avenue, Chicago
$550,000
6 Beds ⋅ 2 Baths ⋅ 12753893 MLS ⋅ ACTIVE Status
Great opportunity to own 2-unit property located in Chicago's Portage Park neighborhood minutes from Jefferson Park and Mayfair. Both units are currently occupied with leases in place through May 2027. Tenants pay electric and gas. Interiors feature vintage character, including woodwork and built-in hutches, with spacious kitchens and formal dining rooms. The property also includes enclosed back porch, unfinished basement with storage and laundry space, unfinished attic, and a detached two-car garage. Conveniently located less than a mile from two CTA Blue Line stations and the Jefferson Park Metra station, with easy access to I-90 and Milwaukee Avenue, shopping, dining, parks, and other neighborhood amenities.

5102 W Sunnyside Avenue, Chicago
5377 N Magnet Avenue, Chicago
$549,900
4 Beds ⋅ 2 Baths ⋅ 12785670 MLS ⋅ ACTIVE Status
Charming Gladstone Park two-flat situated on a desirable corner lot directly across from Gladstone Park! This well-maintained property features two updated units with separate utilities, refreshed kitchens, tile baths, and refinished hardwood floors. The first-floor unit offers an inviting open living space, forced-air heat, and central air conditioning, while the second-floor unit features gas hot water heat and a wall-mounted AC unit. Enjoy a spacious front porch, a lovely yard, and a two-car garage with a covered patio. Conveniently located within walking distance of the Blue Line and Metra, offering easy access to downtown Chicago. A fantastic opportunity for investors or owner-occupants in a great neighborhood! Additional income: $250/month for garage and approx $50/mo for laundry.

5377 N Magnet Avenue, Chicago
5618 N Major Avenue, Chicago
$540,000
6 Beds ⋅ 3 Baths ⋅ 12788881 MLS ⋅ ACTIVE Status
Beautifully maintained building in the desirable Jefferson Park/Gladstone Park area! Each floor features 2 bedrooms and one bathroom. The finished basement offers additional living space with an in-law arrangement, including two bedrooms and a full bathroom. The property is tenant-occupied, but easy to show. All tenants are on month-to-month leases, offering flexibility for investors or owner-occupants.

5618 N Major Avenue, Chicago
5730 W Windsor Avenue, Chicago
$475,000
5 Beds ⋅ 3 Baths ⋅ 12693558 MLS ⋅ ACTIVE Status
This legal 2-flat with a non-conforming garden unit sits on a generous 37-foot-wide lot with garage parking in one of Chicago's most in-demand Northwest Side neighborhoods. Portage Park delivers everything income-focused buyers look for: easy access to CTA bus and nearby Metra service, walkable proximity to grocery stores and everyday retail, and several neighborhood parks within blocks - the kind of location that keeps rental demand steady and turnover low. The investment case is compelling: strong in-place cash flow with a clear, well-supported path to 7% cap rate. Numbers are available upon request for serious inquiries. Whether you're expanding a multi-family portfolio or acquiring your first Chicago 2-flat, this is a rare combination of solid bones, prime location, and real upside. Schedule your showing today.

5730 W Windsor Avenue, Chicago
4825 N Meade Avenue, Chicago
$449,900
4 Beds ⋅ 2 Baths ⋅ 12791701 MLS ⋅ NEW Status
Classic brick architecture and timeless character define this Chicago two-unit property, offering an appealing opportunity for homeowners and investors alike. The spacious interiors feature generous living areas, large windows that welcome natural light, and original wood trim that adds warmth and charm throughout. Both units offer functional kitchens with ample cabinetry, comfortable bedrooms, and flexible living spaces ready for personal touches. The upper-level unit features distinctive ceiling lines and inviting rooms, while the full basement provides additional storage and possibilities for future use. A detached two-car garage adds everyday convenience. With its traditional architectural details and versatile layout, this property offers excellent potential for those looking to customize or invest. Conveniently located in the Jefferson Park area near neighborhood parks, shopping, dining, schools, public transportation, and major roadways, with access to Metra and CTA connections throughout Chicago and surrounding communities.

4825 N Meade Avenue, Chicago
5160 W Sunnyside Avenue, Chicago
$349,900
4 Beds ⋅ 3 Baths ⋅ 12693972 MLS ⋅ ACTIVE 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



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