Chicagorealestatesource.com Search Results

$900,000

Location, location, location! Situated in the desirable Roscoe Village neighborhood within the Clybourn Corridor, this RT-4 zoned area is ideally located approximately half a block north of the Damen Ave, Clybourn Ave and Diversey Ave intersection. Enjoy close proximity to the vibrant, tree-lined Roscoe Street shopping and dining district, along with convenient access to the Kennedy Expressway (I-90/94) and multiple CTA bus routes, including Damen Ave and Diversey Ave. The property features hardwood floors, granite countertops. A great opportunity in a highly convenient Chicago location close to shopping, dining, transportation and neighborhood amenities. 1st floor is vacant and in need of updated. Total of 6 bedrooms and 3 full bathrooms. 2 car garage. Fenced Yard. Laundry hook up in utility room. No owner nor broker warranty legality of number of units in building.

6 Beds ⋅ 3 Baths ⋅ 12753582 MLS ⋅ ACTIVE Status

Location, location, location! Situated in the desirable Roscoe Village neighborhood within the Clybourn Corridor, this RT-4 zoned area is ideally located approximately half a block north of the Damen Ave, Clybourn Ave and Diversey Ave intersection. Enjoy close proximity to the vibrant, tree-lined Roscoe Street shopping and dining district, along with convenient access to the Kennedy Expressway (I-90/94) and multiple CTA bus routes, including Damen Ave and Diversey Ave. The property features hardwood floors, granite countertops. A great opportunity in a highly convenient Chicago location close to shopping, dining, transportation and neighborhood amenities. 1st floor is vacant and in need of updated. Total of 6 bedrooms and 3 full bathrooms. 2 car garage. Fenced Yard. Laundry hook up in utility room. No owner nor broker warranty legality of number of units in building.

2844 N Damen Avenue, Chicago

$1,499,000

Prime Wrigleyville/East Lakeview Investment Opportunity! This meticulously maintained and updated 3-unit building offers an exceptional opportunity for investors or owner-occupants looking to capitalize on strong rental demand in one of Chicago's most desirable neighborhoods. Situated on an oversized 35' x 125' lot and zoned RM-5, the property offers excellent current income with additional potential for future development-buyers are encouraged to explore the possibilities offered by the zoning. Each unit has been well cared for, with numerous updates throughout. The spacious garden unit has living, dining room, kitchen with newer appliances, renovated bathroom, one bedroom and a den. The first-floor unit has 2 bedrooms, separate living and dining room, kitchen with new stainless steel appliances(2024), unit painted (2024), hardwood floors throughout (refinished 2024), bathroom remodel(2021), and new A/C (2025). The 2nd floor owner's unit is a 3 bed, 2 bath, duplex up with hardwood floors throughout. The main level features a large living room and dining room with cathedral ceiling and sliding glass doors leading to front deck, an updated kitchen with a large island and stainless steel appliances along with one bedroom. The upper level provides a spacious primary bedroom with balcony and walk in closet, family room, third bedroom, updated bathroom with double sink, separate shower, jacuzzi tub and in unit laundry. Second floor unit has a new furnace (2025). The property boasts a large backyard and expansive side yard, providing a rare amount of outdoor space. Back deck on each level. Additional income from two-car brick garage and additional parking slab. Great location, walk to Wrigley field, Wrigleyville restaurants, bars, entertainment and Red Line, Brown Line and Purple Line trains.

6 Beds ⋅ 4 Baths ⋅ 12739752 MLS ⋅ ACTIVE Status

Prime Wrigleyville/East Lakeview Investment Opportunity! This meticulously maintained and updated 3-unit building offers an exceptional opportunity for investors or owner-occupants looking to capitalize on strong rental demand in one of Chicago's most desirable neighborhoods. Situated on an oversized 35' x 125' lot and zoned RM-5, the property offers excellent current income with additional potential for future development-buyers are encouraged to explore the possibilities offered by the zoning. Each unit has been well cared for, with numerous updates throughout. The spacious garden unit has living, dining room, kitchen with newer appliances, renovated bathroom, one bedroom and a den. The first-floor unit has 2 bedrooms, separate living and dining room, kitchen with new stainless steel appliances(2024), unit painted (2024), hardwood floors throughout (refinished 2024), bathroom remodel(2021), and new A/C (2025). The 2nd floor owner's unit is a 3 bed, 2 bath, duplex up with hardwood floors throughout. The main level features a large living room and dining room with cathedral ceiling and sliding glass doors leading to front deck, an updated kitchen with a large island and stainless steel appliances along with one bedroom. The upper level provides a spacious primary bedroom with balcony and walk in closet, family room, third bedroom, updated bathroom with double sink, separate shower, jacuzzi tub and in unit laundry. Second floor unit has a new furnace (2025). The property boasts a large backyard and expansive side yard, providing a rare amount of outdoor space. Back deck on each level. Additional income from two-car brick garage and additional parking slab. Great location, walk to Wrigley field, Wrigleyville restaurants, bars, entertainment and Red Line, Brown Line and Purple Line trains.

3405 N Seminary Avenue, Chicago

$635,000

Endless possibilities await at this classic two-unit property in the highly desirable location. Featuring a spacious duplex-up and duplex-down configuration, this building offers an outstanding opportunity for investors, rehabbers, or owner-occupants looking to build equity in one of Chicago's most sought-after neighborhoods. Both units offer generous living space and the convenience of in-unit laundry, providing an excellent foundation for a renovation or value-add project. With strong bones and an ideal layout, this property is ready for your vision. Renovate and maximize rental income, create stunning owner-occupied living with additional rental revenue, or update both units for long-term investment potential. Located in an unbeatable location, you'll enjoy easy access to restaurants, coffee shops, grocery stores, parks, entertainment, public transportation, and major expressways. Just minutes from Roscoe Village, Lakeview, Bucktown, and the Southport Corridor, the neighborhood continues to attract homeowners and renters alike, making this an exceptional investment opportunity.

6 Beds ⋅ 4 Baths ⋅ 12739841 MLS ⋅ CONTINGENT Status

Endless possibilities await at this classic two-unit property in the highly desirable location. Featuring a spacious duplex-up and duplex-down configuration, this building offers an outstanding opportunity for investors, rehabbers, or owner-occupants looking to build equity in one of Chicago's most sought-after neighborhoods. Both units offer generous living space and the convenience of in-unit laundry, providing an excellent foundation for a renovation or value-add project. With strong bones and an ideal layout, this property is ready for your vision. Renovate and maximize rental income, create stunning owner-occupied living with additional rental revenue, or update both units for long-term investment potential. Located in an unbeatable location, you'll enjoy easy access to restaurants, coffee shops, grocery stores, parks, entertainment, public transportation, and major expressways. Just minutes from Roscoe Village, Lakeview, Bucktown, and the Southport Corridor, the neighborhood continues to attract homeowners and renters alike, making this an exceptional investment opportunity.

3008 N Clybourn Avenue, Chicago

$1,400,000

Stunning and well-maintained two-flat in the heart of the Southport Corridor/ Blaine School. The owner's duplex-up spans the second and third floors with four bedrooms, two updated baths, and two bedrooms on each level. The bright main floor features a generous living room with high ceilings and a sunny kitchen with an island, gas cooking, and newer appliances. Two private decks and exclusive use of the beautifully landscaped backyard with paver patio provide exceptional outdoor space. The first-floor two-bedroom, one-bath apartment offers central heat and air, a private rear deck, basement storage, and free laundry. Two-car garage. Set on a tree-lined, community-focused block just steps from Southport Avenue, the Brown Line, shops, restaurants, Blaine, and an easy walk to Wrigley Field.

6 Beds ⋅ 3 Baths ⋅ 12731167 MLS ⋅ CONTINGENT Status

Stunning and well-maintained two-flat in the heart of the Southport Corridor/ Blaine School. The owner's duplex-up spans the second and third floors with four bedrooms, two updated baths, and two bedrooms on each level. The bright main floor features a generous living room with high ceilings and a sunny kitchen with an island, gas cooking, and newer appliances. Two private decks and exclusive use of the beautifully landscaped backyard with paver patio provide exceptional outdoor space. The first-floor two-bedroom, one-bath apartment offers central heat and air, a private rear deck, basement storage, and free laundry. Two-car garage. Set on a tree-lined, community-focused block just steps from Southport Avenue, the Brown Line, shops, restaurants, Blaine, and an easy walk to Wrigley Field.

3719 N Janssen Avenue, Chicago

$1,500,000

Situated on a premier, tree-lined street in the highly coveted Blaine School District. Exceptionally rare Lakeview multi-family investment asset presenting an unrivaled turn-key opportunity for either a yield-focused portfolio investor or a live-in owner looking to substantially subsidize their mortgage. Brick 2 flat with a non-conforming basement apartment and a 2-unit coach house in the rear. All kitchens and baths have been updated. All separate gas forced air furnaces. Currently generating $125,580. gross income. With expenses at $38607. that's a net cash flow of $86973. or about a 5.7% cap rate. Rents as follows: Front building 1st floor $1910 6/27, 2nd floor $3000 Vac. Garden $1450. 6/27, Coach house 1st $1705. 6/27, Coach house 2 3 BR 2 bath $2850. 7/27. Multi million dollar homes up and down the block in this highly sought after location.

10 Beds ⋅ 5 Baths ⋅ 12728198 MLS ⋅ CONTINGENT Status

Situated on a premier, tree-lined street in the highly coveted Blaine School District. Exceptionally rare Lakeview multi-family investment asset presenting an unrivaled turn-key opportunity for either a yield-focused portfolio investor or a live-in owner looking to substantially subsidize their mortgage. Brick 2 flat with a non-conforming basement apartment and a 2-unit coach house in the rear. All kitchens and baths have been updated. All separate gas forced air furnaces. Currently generating $125,580. gross income. With expenses at $38607. that's a net cash flow of $86973. or about a 5.7% cap rate. Rents as follows: Front building 1st floor $1910 6/27, 2nd floor $3000 Vac. Garden $1450. 6/27, Coach house 1st $1705. 6/27, Coach house 2 3 BR 2 bath $2850. 7/27. Multi million dollar homes up and down the block in this highly sought after location.

3709 N Bosworth Avenue, Chicago

$1,600,000

Beautifully maintained and thoughtfully updated, this classic Chicago three-flat is located in the heart of Lakeview. Ideal for investors or owner-occupants, the property offers a great "house hacking" setup-live in the spacious owner's duplex-down while generating rental income from the two generously sized upper units. Throughout the building, vintage character is paired with modern improvements. Each unit features tall ceilings, oversized windows, hardwood floors, original woodwork, decorative fireplaces, and separate living and dining areas. Updated kitchens include stainless steel appliances, dishwashers, ample cabinetry, and modern finishes. Each residence also has its own HVAC system and in-unit washer and dryer, providing the conveniences today's renters expect. Spanning two levels, the owner's duplex-down offers generous living space and plenty of flexibility. The expansive kitchen features warm wood cabinetry, stone countertops, upgraded appliances, a large island, and abundant storage. Updated bathrooms, flexible office or workout space, multiple living areas, and direct access to the rear outdoor space make it an ideal owner's residence. A brand-new roof, private rear decks, a patio and courtyard area, and three off-street parking spaces add to the property's appeal. Impeccably cared for and updated throughout, this is a turnkey multifamily property near dining, shopping, nightlife, public transportation, and everything Lakeview has to offer. Move in, rent out, or add a strong asset to your investment portfolio.

9 Beds ⋅ 4 Baths ⋅ 12723283 MLS ⋅ CLOSED Status

Beautifully maintained and thoughtfully updated, this classic Chicago three-flat is located in the heart of Lakeview. Ideal for investors or owner-occupants, the property offers a great "house hacking" setup-live in the spacious owner's duplex-down while generating rental income from the two generously sized upper units. Throughout the building, vintage character is paired with modern improvements. Each unit features tall ceilings, oversized windows, hardwood floors, original woodwork, decorative fireplaces, and separate living and dining areas. Updated kitchens include stainless steel appliances, dishwashers, ample cabinetry, and modern finishes. Each residence also has its own HVAC system and in-unit washer and dryer, providing the conveniences today's renters expect. Spanning two levels, the owner's duplex-down offers generous living space and plenty of flexibility. The expansive kitchen features warm wood cabinetry, stone countertops, upgraded appliances, a large island, and abundant storage. Updated bathrooms, flexible office or workout space, multiple living areas, and direct access to the rear outdoor space make it an ideal owner's residence. A brand-new roof, private rear decks, a patio and courtyard area, and three off-street parking spaces add to the property's appeal. Impeccably cared for and updated throughout, this is a turnkey multifamily property near dining, shopping, nightlife, public transportation, and everything Lakeview has to offer. Move in, rent out, or add a strong asset to your investment portfolio.

2838 N Sheffield Street, Chicago

$1,425,000

Hot West Lakeview/ Roscoe Village neighborhoods this large 2 flat on a tree lined street perfect for investment / or live in one unit and get rental income from other unit. The top duplex up unit has 3 bedroom/2 bath with many updates - newly renovated chef's kitchen with new SS appliances and built-in breakfast banquette. Large cathedral ceilings with skylights and built-ins in the living room. Wood floors throughout. Loft space ideal for home office or entertainment. Large primary ensuite bathroom with freestanding soaking tub and separate dual shower heads remodeled in the last two years. Unit 1 has two bedrooms/ 1.5 baths and has been renovated in 2023 with an updated kitchen, bathroom with plenty of storage. Separate dining area, bonus room off kitchen great for home office. Great closet space and one bedroom with a connecting powder room. The basement is perfect for storage, common fitness, laundry or future duplex down option with tall ceilings. Fenced in yard with turf in rear with detached, 2 car garage Each unit has its own deck completely rebuilt in 2023. Great location! Steps to Paulina Brown line- walk to Restaurants, grocery, coffee, shops, night life and more. Walking distance to a Cubs game and Southport corridor with Hamilton Elementary school up the block. Don't miss this great investment opportunity in a wonderful area. Unit 1 first floor is currently Rented $3100 until 9/30/27.Proposed basement floorplan in additional information. Offers due Sunday 8/2 by 5pm.

5 Beds ⋅ 4 Baths ⋅ 12716023 MLS ⋅ PENDING Status

Hot West Lakeview/ Roscoe Village neighborhoods this large 2 flat on a tree lined street perfect for investment / or live in one unit and get rental income from other unit. The top duplex up unit has 3 bedroom/2 bath with many updates - newly renovated chef's kitchen with new SS appliances and built-in breakfast banquette. Large cathedral ceilings with skylights and built-ins in the living room. Wood floors throughout. Loft space ideal for home office or entertainment. Large primary ensuite bathroom with freestanding soaking tub and separate dual shower heads remodeled in the last two years. Unit 1 has two bedrooms/ 1.5 baths and has been renovated in 2023 with an updated kitchen, bathroom with plenty of storage. Separate dining area, bonus room off kitchen great for home office. Great closet space and one bedroom with a connecting powder room. The basement is perfect for storage, common fitness, laundry or future duplex down option with tall ceilings. Fenced in yard with turf in rear with detached, 2 car garage Each unit has its own deck completely rebuilt in 2023. Great location! Steps to Paulina Brown line- walk to Restaurants, grocery, coffee, shops, night life and more. Walking distance to a Cubs game and Southport corridor with Hamilton Elementary school up the block. Don't miss this great investment opportunity in a wonderful area. Unit 1 first floor is currently Rented $3100 until 9/30/27.Proposed basement floorplan in additional information. Offers due Sunday 8/2 by 5pm.

3431 N Paulina Street, Chicago

$914,900

This fixer upper is a classic brick two-flat and is nestled in one of the city's most vibrant and desirable areas and has two bedrooms and 1 bath per unit. From the moment you enter the building you will appreciate the character and craftsmanship. The units have beautiful hardwood floors and rich woodwork, original built-ins and great details that reflect a home that is no easy to find today. The kitchens feature generous pantries and the rear porch is great for extra space. The full unfinished basement provides lots of space for storage, utilities and laundry. The backyard comes complete with a newer concrete parking pad that adds valuable parking for your convenience after a long day. Full renovation is needed, but it presents an incredible opportunity for the right buyer or investor. These opportunities don't come along often so bring your imagination and your plans for the future and call to schedule a tour. Sold As-Is ONLY.

4 Beds ⋅ 2 Baths ⋅ 12718054 MLS ⋅ CONTINGENT Status

This fixer upper is a classic brick two-flat and is nestled in one of the city's most vibrant and desirable areas and has two bedrooms and 1 bath per unit. From the moment you enter the building you will appreciate the character and craftsmanship. The units have beautiful hardwood floors and rich woodwork, original built-ins and great details that reflect a home that is no easy to find today. The kitchens feature generous pantries and the rear porch is great for extra space. The full unfinished basement provides lots of space for storage, utilities and laundry. The backyard comes complete with a newer concrete parking pad that adds valuable parking for your convenience after a long day. Full renovation is needed, but it presents an incredible opportunity for the right buyer or investor. These opportunities don't come along often so bring your imagination and your plans for the future and call to schedule a tour. Sold As-Is ONLY.

1738 W Byron Street, Chicago

$1,389,375

Located in the vibrant heart of Lakeview, 3423 N. Seminary is a well-maintained legal 3unit building featuring two spacious three-bedroom apartments and a four-bedroom duplex up. This property includes a two-car brick garage and offers excellent rental income, with all units leased through May and July 2027, generating a net operating income of $75,806.47 after expenses and property taxes. Pride of ownership shines through updates and care over the years. Each unit boasts a private balcony and access to a fenced backyard with a charming brick patio. Additional conveniences include a washer, dryer, and extra storage in the basement. Photos reflect the current condition, and the property is ready for new ownership with tenant leases in place. The building has been thoughtfully updated and offers a low-maintenance, turnkey investment in one of Chicago's most desirable neighborhoods. Rarely does an opportunity combine location, condition, and income potential with this level of flexibility.

10 Beds ⋅ 4 Baths ⋅ 12717972 MLS ⋅ CLOSED Status

Located in the vibrant heart of Lakeview, 3423 N. Seminary is a well-maintained legal 3unit building featuring two spacious three-bedroom apartments and a four-bedroom duplex up. This property includes a two-car brick garage and offers excellent rental income, with all units leased through May and July 2027, generating a net operating income of $75,806.47 after expenses and property taxes. Pride of ownership shines through updates and care over the years. Each unit boasts a private balcony and access to a fenced backyard with a charming brick patio. Additional conveniences include a washer, dryer, and extra storage in the basement. Photos reflect the current condition, and the property is ready for new ownership with tenant leases in place. The building has been thoughtfully updated and offers a low-maintenance, turnkey investment in one of Chicago's most desirable neighborhoods. Rarely does an opportunity combine location, condition, and income potential with this level of flexibility.

3423 N Seminary Street, Chicago

$960,000

Handsome Lakeview Brick Chicago two flat awaiting your rehab and/or single-family home conversion ideas. Current owner has maintained the home and has installed a completely new roof (2026), new water heater (2024), Furnace and CAC (2016). Lot is 25'X125' and has RS-3 Zoning. Full basement is partially finished and is dry with center beam height of 6'4". Windows were done in 2000 and are in good shape. Kitchens and baths are dated. Location, Location, Location. Perfect distance from the train, Wrigley Field, Lake Michigan, and all the restaurants, schools, entertainment and shopping.

5 Beds ⋅ 2 Baths ⋅ 12711898 MLS ⋅ CLOSED Status

Handsome Lakeview Brick Chicago two flat awaiting your rehab and/or single-family home conversion ideas. Current owner has maintained the home and has installed a completely new roof (2026), new water heater (2024), Furnace and CAC (2016). Lot is 25'X125' and has RS-3 Zoning. Full basement is partially finished and is dry with center beam height of 6'4". Windows were done in 2000 and are in good shape. Kitchens and baths are dated. Location, Location, Location. Perfect distance from the train, Wrigley Field, Lake Michigan, and all the restaurants, schools, entertainment and shopping.

3714 N Hermitage Avenue, Chicago

$1,265,000

Incredible Lakeview investment opportunity with RT-3.5 zoning, allowing for two-flats, townhouses, low-density apartment buildings, and single-family homes. Currently generating below market value $7,000/month in rental income with substantial upside through aesthetic renovations and rental increases, this property is being offered as a portfolio of three individual condo PINs, with the potential to convert to a single tax PIN. Constructed in 1994, the 4-story BRICK & BLOCK building features three units totaling 7 bedrooms and 4 bathrooms. Unit #3 is a spacious 3 bed/2 bath duplex-up with vaulted ceilings and streaming natural light - 1,862sqft, Unit #2 is a 2 bed/1 bath - 919sqft, and Unit #1 is a 2 bed/1 bath garden-level unit - 907sqft. ALL units feature private rear balconies and are individually metered and include in-unit washer and dryer, central HVAC, and individual water heaters. The property also offers a private fenced backyard and three rear parking spaces on a parking pad. Good long-term tenants who pay on time: Unit #3 rents for $3,300/month through 5/31/27, Unit #2 rents for $1,900/month through 4/30/27, and Unit #1 rents for $1,800/month through 8/31/26. Walk to Jewel Osco, Diversey Train and Buses. Rarely does a cash-flowing, value-add asset with flexible zoning, multiple exit strategies, and long-term redevelopment potential become available in one of Chicago's most sought-after neighborhoods!

7 Beds ⋅ 5 Baths ⋅ 12705120 MLS ⋅ CLOSED Status

Incredible Lakeview investment opportunity with RT-3.5 zoning, allowing for two-flats, townhouses, low-density apartment buildings, and single-family homes. Currently generating below market value $7,000/month in rental income with substantial upside through aesthetic renovations and rental increases, this property is being offered as a portfolio of three individual condo PINs, with the potential to convert to a single tax PIN. Constructed in 1994, the 4-story BRICK & BLOCK building features three units totaling 7 bedrooms and 4 bathrooms. Unit #3 is a spacious 3 bed/2 bath duplex-up with vaulted ceilings and streaming natural light - 1,862sqft, Unit #2 is a 2 bed/1 bath - 919sqft, and Unit #1 is a 2 bed/1 bath garden-level unit - 907sqft. ALL units feature private rear balconies and are individually metered and include in-unit washer and dryer, central HVAC, and individual water heaters. The property also offers a private fenced backyard and three rear parking spaces on a parking pad. Good long-term tenants who pay on time: Unit #3 rents for $3,300/month through 5/31/27, Unit #2 rents for $1,900/month through 4/30/27, and Unit #1 rents for $1,800/month through 8/31/26. Walk to Jewel Osco, Diversey Train and Buses. Rarely does a cash-flowing, value-add asset with flexible zoning, multiple exit strategies, and long-term redevelopment potential become available in one of Chicago's most sought-after neighborhoods!

1507 W George Street, Chicago

$1,249,900

3141 N Oakley - gut-renovated 3-flat in the heart of Roscoe A rare opportunity to own a fully updated multifamily asset in one of Chicago's most consistently in-demand neighborhoods, just steps from Hamlin Park. This handsome brick 3-flat features two 3BD/1BA units and one 2BD/1BA unit - every unit gut-renovated top to bottom with new kitchens, quartz countertops, modern baths, and central A/C. Nothing to do but collect rent. The full unfinished basement offers clear value-add potential (storage, laundry expansion, or future buildout), and the brick 2-car garage is a premium amenity rarely found in the area. Strong in-place rental income with long-term upside as Roscoe Village continues to appreciate. Turnkey condition, proven rents, and a compelling basis - ideal for investors and house-hackers alike.

8 Beds ⋅ 3 Baths ⋅ 12697754 MLS ⋅ CLOSED Status

3141 N Oakley - gut-renovated 3-flat in the heart of Roscoe A rare opportunity to own a fully updated multifamily asset in one of Chicago's most consistently in-demand neighborhoods, just steps from Hamlin Park. This handsome brick 3-flat features two 3BD/1BA units and one 2BD/1BA unit - every unit gut-renovated top to bottom with new kitchens, quartz countertops, modern baths, and central A/C. Nothing to do but collect rent. The full unfinished basement offers clear value-add potential (storage, laundry expansion, or future buildout), and the brick 2-car garage is a premium amenity rarely found in the area. Strong in-place rental income with long-term upside as Roscoe Village continues to appreciate. Turnkey condition, proven rents, and a compelling basis - ideal for investors and house-hackers alike.

3141 N Oakley Avenue, Chicago

$1,212,235

This 3-story multi-unit building features a fantastic 2BR, 2BTH Duplex Up apartment with a modern open floor plan, living room fireplace, skylights, spacious dining area, large kitchen with ample counter space, granite counters, new stainless appliances and new flooring both in 2025, in-unit laundry room and two private outdoor spaces! Perfect for the live-in owner or as a high-end rental. The remainder of the building is comprised of a 2BR, 1BTH apartment with updated bathroom, in-unit laundry, private back deck on the first floor and a garden level 1BR plus den apartment (den could easily be converted into a 2nd bedroom) with newer flooring, recently remodeled kitchen and bath and its own front and back entrances. This building has been incredibly well cared for by its long-term, live-in owner with a long list of improvements including: a new 2-car garage (2024), a new roof (2022), new garden apartment furnace (2023), Hardee Board siding on the front of building (2020) and new windows in 2020. Each apartment has their own HVAC systems with individual controls. This property represents a tremendous opportunity with so much potential for high rental income, all in an unbeatable and very easy-to-rent Lakeview location close to restaurants, coffee houses, grocery stores, shopping, nightlife and public transportation, including the Brown Line Wellington "L" Stop which is just a 7-minute walk away. Zoning Certificate for this property has been ordered but isn't back yet. It should be assumed that this is a legal 2-unit building with a non-confirming garden apartment unless the certification shows differently.

5 Beds ⋅ 4 Baths ⋅ 12688705 MLS ⋅ CLOSED Status

This 3-story multi-unit building features a fantastic 2BR, 2BTH Duplex Up apartment with a modern open floor plan, living room fireplace, skylights, spacious dining area, large kitchen with ample counter space, granite counters, new stainless appliances and new flooring both in 2025, in-unit laundry room and two private outdoor spaces! Perfect for the live-in owner or as a high-end rental. The remainder of the building is comprised of a 2BR, 1BTH apartment with updated bathroom, in-unit laundry, private back deck on the first floor and a garden level 1BR plus den apartment (den could easily be converted into a 2nd bedroom) with newer flooring, recently remodeled kitchen and bath and its own front and back entrances. This building has been incredibly well cared for by its long-term, live-in owner with a long list of improvements including: a new 2-car garage (2024), a new roof (2022), new garden apartment furnace (2023), Hardee Board siding on the front of building (2020) and new windows in 2020. Each apartment has their own HVAC systems with individual controls. This property represents a tremendous opportunity with so much potential for high rental income, all in an unbeatable and very easy-to-rent Lakeview location close to restaurants, coffee houses, grocery stores, shopping, nightlife and public transportation, including the Brown Line Wellington "L" Stop which is just a 7-minute walk away. Zoning Certificate for this property has been ordered but isn't back yet. It should be assumed that this is a legal 2-unit building with a non-confirming garden apartment unless the certification shows differently.

3013 N Racine Avenue, Chicago

$800,000

Discover the potential of this classic Chicago brick multi-unit building located on a quiet residential street in the highly desirable Lakeview neighborhood. This property offers timeless character and endless possibilities for its next owner. Whether you're looking to live in one unit while renting the others, create a multi-generational living space, or reimagine the property to suit your vision, this property offers the space and foundation to make it happen. The property also includes a detached garage and full basement. Large windows, hardwood floors, and classic Chicago architecture give the building charm that can be restored and enhanced over time. Located just moments from Wrigley Field, restaurants, shops, parks, and public transportation, you'll enjoy the convenience of city living while being tucked into a charming residential block. Bring your ideas and make this historic property your own. Property is being sold AS-IS and subject to Short sale lender approval.

8 Beds ⋅ 5 Baths ⋅ 12683604 MLS ⋅ CONTINGENT Status

Discover the potential of this classic Chicago brick multi-unit building located on a quiet residential street in the highly desirable Lakeview neighborhood. This property offers timeless character and endless possibilities for its next owner. Whether you're looking to live in one unit while renting the others, create a multi-generational living space, or reimagine the property to suit your vision, this property offers the space and foundation to make it happen. The property also includes a detached garage and full basement. Large windows, hardwood floors, and classic Chicago architecture give the building charm that can be restored and enhanced over time. Located just moments from Wrigley Field, restaurants, shops, parks, and public transportation, you'll enjoy the convenience of city living while being tucked into a charming residential block. Bring your ideas and make this historic property your own. Property is being sold AS-IS and subject to Short sale lender approval.

3639 N Greenview Avenue, Chicago

$1,340,000

Exceptional opportunity in the heart of the Southport Corridor and highly sought-after Blaine Elementary School District. This well-maintained 2-flat features a spacious owner's duplex-up with 3 bedrooms and 3 baths plus a separate 2 bed, 1 bath rental unit for additional income. The owner's residence offers tall ceilings, hardwood floors, expansive living and dining spaces, and an updated kitchen with white cabinetry, quartz countertops, and stainless steel appliances. The rear of the home opens to a sunny west-facing deck and flexible family room or dining area. A dramatic open staircase leads to the bedroom level featuring newer carpeting, a generous primary suite with attached bath and ample closet space, two additional bedrooms, and a full hallway bath. Central heat and air conditioning throughout. Additional features include a backyard, 2-car garage, unfinished basement with laundry for the rental unit, and an unbeatable location near restaurants, shopping, parks, transportation, and all that Lakeview has to offer.

5 Beds ⋅ 4 Baths ⋅ 12674025 MLS ⋅ CLOSED Status

Exceptional opportunity in the heart of the Southport Corridor and highly sought-after Blaine Elementary School District. This well-maintained 2-flat features a spacious owner's duplex-up with 3 bedrooms and 3 baths plus a separate 2 bed, 1 bath rental unit for additional income. The owner's residence offers tall ceilings, hardwood floors, expansive living and dining spaces, and an updated kitchen with white cabinetry, quartz countertops, and stainless steel appliances. The rear of the home opens to a sunny west-facing deck and flexible family room or dining area. A dramatic open staircase leads to the bedroom level featuring newer carpeting, a generous primary suite with attached bath and ample closet space, two additional bedrooms, and a full hallway bath. Central heat and air conditioning throughout. Additional features include a backyard, 2-car garage, unfinished basement with laundry for the rental unit, and an unbeatable location near restaurants, shopping, parks, transportation, and all that Lakeview has to offer.

3714 N Bosworth Avenue, Chicago

$1,865,000

Turnkey investment opportunity in fantastic Lakeview location! This is a well maintained 3 unit building with a non-conforming garden unit. Well maintained building features recently updated units with central air/heat, newer kitchens and baths, dishwashers, hardwood floors and outdoor decks. Cathedral ceilings on the 3rd floor. Each unit has its own laundry allowing for premium rents. Tenants responsible for their own utilities and the property has exterior parking available for 6 cars. Opportunity to duplex 1st floor unit down to garden level to create an awesome owner's unit. Please note neither the owner nor broker make any representation of the legality of the garden unit.

6 Beds ⋅ 7 Baths ⋅ 12674163 MLS ⋅ CLOSED Status

Turnkey investment opportunity in fantastic Lakeview location! This is a well maintained 3 unit building with a non-conforming garden unit. Well maintained building features recently updated units with central air/heat, newer kitchens and baths, dishwashers, hardwood floors and outdoor decks. Cathedral ceilings on the 3rd floor. Each unit has its own laundry allowing for premium rents. Tenants responsible for their own utilities and the property has exterior parking available for 6 cars. Opportunity to duplex 1st floor unit down to garden level to create an awesome owner's unit. Please note neither the owner nor broker make any representation of the legality of the garden unit.

1442 W Melrose Street, Chicago

$1,299,000

Exceptional opportunity to own a classic Chicago Greystone in one of Lakeview's most sought-after locations. Situated just steps from Wrigley Field, the Southport Corridor, CTA transit, shopping, dining, and entertainment. This well-maintained investment property offers the perfect blend of historic charm, stable income, and long-term upside. The building consists of two spacious 3-bed / 1-bath apartments plus a non-conforming 2-bed garden unit. All the units showcase features that tenants love, including hardwood floors, good room sizes, separate living & dining rooms, Washer & Dryer in each unit. Additional features include gas-forced heat and central A/C, rear porches, and 3 tandem parking spaces accommodating up to six vehicles. Investors will appreciate the opportunity to increase rents through strategic updates, while owner-occupants may explore future renovation, duplexing, or conversion possibilities. Whether you're seeking a turnkey investment, a value-add opportunity, or a chance to own a piece of classic Chicago architecture, this Lakeview Greystone delivers location, character, and exceptional potential in one of the city's most enduring neighborhoods.

8 Beds ⋅ 3 Baths ⋅ 12666976 MLS ⋅ CONTINGENT Status

Exceptional opportunity to own a classic Chicago Greystone in one of Lakeview's most sought-after locations. Situated just steps from Wrigley Field, the Southport Corridor, CTA transit, shopping, dining, and entertainment. This well-maintained investment property offers the perfect blend of historic charm, stable income, and long-term upside. The building consists of two spacious 3-bed / 1-bath apartments plus a non-conforming 2-bed garden unit. All the units showcase features that tenants love, including hardwood floors, good room sizes, separate living & dining rooms, Washer & Dryer in each unit. Additional features include gas-forced heat and central A/C, rear porches, and 3 tandem parking spaces accommodating up to six vehicles. Investors will appreciate the opportunity to increase rents through strategic updates, while owner-occupants may explore future renovation, duplexing, or conversion possibilities. Whether you're seeking a turnkey investment, a value-add opportunity, or a chance to own a piece of classic Chicago architecture, this Lakeview Greystone delivers location, character, and exceptional potential in one of the city's most enduring neighborhoods.

1513 W Addison Street, Chicago

$1,100,000

Well-maintained 3-unit investment property in the heart of Roscoe Village/West Lakeview, ideally situated directly across from beloved Hamlin Park, home to one of the neighborhood's most beautiful parks and outdoor pools. Set on a prominent corner lot with grandfathered positioning that allows for a massive private yard, this solid multi-unit building offers incredibly spacious layouts, abundant natural light, and numerous recent improvements. The property features a duplex-down 3 bed/2 bath unit, along with two oversized 2 bed/1 bath units, each offering separate dining areas, generous room sizes, and tons of windows throughout. Exterior parking provides additional income potential, while the sprawling backyard is an exceptionally rare city find - professionally designed with turf, pavers, lush landscaping, and a brand-new wooden fence, creating the perfect outdoor retreat. Recent improvements and building updates include a brand-new ejector pump, roof replacement approximately 6 years ago, drain tile system installation, updated flooring throughout the units over the years, several replacement windows, and mechanical updates including newer furnaces and AC condensers. An outstanding opportunity for an owner-occupant or investor seeking strong rental income, additional value-add potential, and a prime location in one of Chicago's most sought-after neighborhoods.

7 Beds ⋅ 4 Baths ⋅ 12670734 MLS ⋅ CLOSED Status

Well-maintained 3-unit investment property in the heart of Roscoe Village/West Lakeview, ideally situated directly across from beloved Hamlin Park, home to one of the neighborhood's most beautiful parks and outdoor pools. Set on a prominent corner lot with grandfathered positioning that allows for a massive private yard, this solid multi-unit building offers incredibly spacious layouts, abundant natural light, and numerous recent improvements. The property features a duplex-down 3 bed/2 bath unit, along with two oversized 2 bed/1 bath units, each offering separate dining areas, generous room sizes, and tons of windows throughout. Exterior parking provides additional income potential, while the sprawling backyard is an exceptionally rare city find - professionally designed with turf, pavers, lush landscaping, and a brand-new wooden fence, creating the perfect outdoor retreat. Recent improvements and building updates include a brand-new ejector pump, roof replacement approximately 6 years ago, drain tile system installation, updated flooring throughout the units over the years, several replacement windows, and mechanical updates including newer furnaces and AC condensers. An outstanding opportunity for an owner-occupant or investor seeking strong rental income, additional value-add potential, and a prime location in one of Chicago's most sought-after neighborhoods.

2925 N Damen Avenue, Chicago

$2,349,000

11 Beds ⋅ 7 Baths ⋅ 12664568 MLS ⋅ CONTINGENT Status

Chicago

$1,175,000

Great investment opportunity in Roscoe Village on an oversized lot! All units updated with newer kitchens and baths, central A/C and washer/dryer in unit. Tenants pay their own electric and gas. All units currently leased, but easy opportunity to become an owner occupant. Second floor front unit is a spacious duplex up that makes a wonderful owner's unit. Total current annual rent income of $88,200. 3 car garage, outdoor space and fenced yard for tenants to enjoy. Very desirable location near shopping, dining, parks, transportation and nightlife.

7 Beds ⋅ 5 Baths ⋅ 12663205 MLS ⋅ ACTIVE Status

Great investment opportunity in Roscoe Village on an oversized lot! All units updated with newer kitchens and baths, central A/C and washer/dryer in unit. Tenants pay their own electric and gas. All units currently leased, but easy opportunity to become an owner occupant. Second floor front unit is a spacious duplex up that makes a wonderful owner's unit. Total current annual rent income of $88,200. 3 car garage, outdoor space and fenced yard for tenants to enjoy. Very desirable location near shopping, dining, parks, transportation and nightlife.

2115 W Wellington Avenue, Chicago

$1,346,475

Classic and beautifully maintained, this income-producing Lakeview 3-flat offers the perfect blend of vintage charm, flexible living space, and strong investment potential. The sun-filled first-floor unit features 2 bedrooms and 1 bath, highlighted by timeless woodwork, generous living space, and a private rear deck. The garden apartment offers an additional 2-bedroom, 1-bath layout, ideal for steady rental income. The standout top-floor duplex-up lives like an owner's home, featuring 4 bedrooms, 2 baths, and a private top-level deck perfect for entertaining or relaxing outdoors. Currently tenant-occupied, it presents an exceptional future owner's unit opportunity. Additional highlights include separate utilities for all units, well-maintained mechanicals, and an unbeatable Lakeview location close to restaurants, shopping, parks, nightlife, and public transportation. A rare opportunity for investors or owner-occupants seeking strong income and long-term value in one of Chicago's most desirable neighborhoods.

8 Beds ⋅ 4 Baths ⋅ 12659654 MLS ⋅ CLOSED Status

Classic and beautifully maintained, this income-producing Lakeview 3-flat offers the perfect blend of vintage charm, flexible living space, and strong investment potential. The sun-filled first-floor unit features 2 bedrooms and 1 bath, highlighted by timeless woodwork, generous living space, and a private rear deck. The garden apartment offers an additional 2-bedroom, 1-bath layout, ideal for steady rental income. The standout top-floor duplex-up lives like an owner's home, featuring 4 bedrooms, 2 baths, and a private top-level deck perfect for entertaining or relaxing outdoors. Currently tenant-occupied, it presents an exceptional future owner's unit opportunity. Additional highlights include separate utilities for all units, well-maintained mechanicals, and an unbeatable Lakeview location close to restaurants, shopping, parks, nightlife, and public transportation. A rare opportunity for investors or owner-occupants seeking strong income and long-term value in one of Chicago's most desirable neighborhoods.

1448 W George Street, Chicago

$1,685,000

Situated on a premier, tree-lined street in the highly coveted Blaine School District, this exceptionally rare Lakeview multi-family investment asset underwent a comprehensive, high-end rehabilitation in 2025, generating a powerhouse monthly rental income of $11,200 ($134,400 gross annually) anchored by a secure duplex lease extending into March 2028. Presenting an unrivaled turn-key opportunity for either a yield-focused portfolio investor or a live-in owner looking to substantially subsidize their mortgage, the impressive 4,264-square-foot footprint features three renovated two-bedroom residences and an owner-caliber three-bedroom, two-and-a-half-bath penthouse duplex up. The stunning, sun-drenched penthouse showcases soaring cathedral and beamed ceilings illuminated by bright skylights, a gracious living room with architectural bay windows and a gas fireplace, and a professional-grade gourmet kitchen boasting rich granite countertops, a massive prep island, and a premier Viking refrigerator alongside high-end stainless steel appliances. This crown jewel unit is completed by an expansive private roof deck perfect for entertaining, second-floor in-unit laundry, and a tranquil primary suite featuring a spa-like master bathroom with a double-bowl vanity, separate soaking tub, and a custom shower. Complementing the duplex are the three turn-key two-bedroom residences showing high-value finishes such as updated kitchens with stainless steel appliances, new individual thermostats, and pristine hardwood flooring, with the rear unit featuring a large, versatile three-season sunroom. Mechanical and structural integrity is built directly into this passive income producer, highlighted by comprehensively updated electrical wiring, an optimized heating system with freshly insulated lines, and fully flushed radiators for effortless seasonal climate control. Finished with a dry, spacious basement providing dedicated resident storage lockers, new common laundry, and a detached two-car garage with a newly replaced door, this magnificent building sits just steps from the boutique shopping and dining of the Southport Corridor, public transit, and the vibrant local energy of Wrigleyville.

9 Beds ⋅ 6 Baths ⋅ 12632607 MLS ⋅ CLOSED Status

Situated on a premier, tree-lined street in the highly coveted Blaine School District, this exceptionally rare Lakeview multi-family investment asset underwent a comprehensive, high-end rehabilitation in 2025, generating a powerhouse monthly rental income of $11,200 ($134,400 gross annually) anchored by a secure duplex lease extending into March 2028. Presenting an unrivaled turn-key opportunity for either a yield-focused portfolio investor or a live-in owner looking to substantially subsidize their mortgage, the impressive 4,264-square-foot footprint features three renovated two-bedroom residences and an owner-caliber three-bedroom, two-and-a-half-bath penthouse duplex up. The stunning, sun-drenched penthouse showcases soaring cathedral and beamed ceilings illuminated by bright skylights, a gracious living room with architectural bay windows and a gas fireplace, and a professional-grade gourmet kitchen boasting rich granite countertops, a massive prep island, and a premier Viking refrigerator alongside high-end stainless steel appliances. This crown jewel unit is completed by an expansive private roof deck perfect for entertaining, second-floor in-unit laundry, and a tranquil primary suite featuring a spa-like master bathroom with a double-bowl vanity, separate soaking tub, and a custom shower. Complementing the duplex are the three turn-key two-bedroom residences showing high-value finishes such as updated kitchens with stainless steel appliances, new individual thermostats, and pristine hardwood flooring, with the rear unit featuring a large, versatile three-season sunroom. Mechanical and structural integrity is built directly into this passive income producer, highlighted by comprehensively updated electrical wiring, an optimized heating system with freshly insulated lines, and fully flushed radiators for effortless seasonal climate control. Finished with a dry, spacious basement providing dedicated resident storage lockers, new common laundry, and a detached two-car garage with a newly replaced door, this magnificent building sits just steps from the boutique shopping and dining of the Southport Corridor, public transit, and the vibrant local energy of Wrigleyville.

3722 N Bosworth Avenue, Chicago

$1,575,000

Welcome to 1341 W. Eddy, a stunning all brick 3-flat in the heart of Wrigleyville, ideally located just steps from the Brown Line and all of the shops, restaurants, and nightlife along the vibrant Southport Corridor. This turnkey investment property features three charming and sun-filled units: Unit 1 offers 2 bedrooms and 1 bathroom, while Units 2 and 3 each feature 3 bedrooms and 1 bathroom. All units boast great natural light, spacious layouts, and access to large outdoor decks. Recent improvements include a new roof installed in 2022 with transferable warranties, updated windows, and new copper piping installed on the first floor. Additional features include basement laundry and a 2-car garage that was rebuilt within the last five years. The garage is not currently leased to tenants and provides additional income potential through rentals during Cubs games and concerts. All units are tenant-occupied with leases in place through 2027, making this a true armchair investment in an unbeatable A+ location with consistent rental demand. Explore the property in 3D by clicking the virtual tour button and walk through every detail from the comfort of your home.

8 Beds ⋅ 3 Baths ⋅ 12659463 MLS ⋅ CLOSED Status

Welcome to 1341 W. Eddy, a stunning all brick 3-flat in the heart of Wrigleyville, ideally located just steps from the Brown Line and all of the shops, restaurants, and nightlife along the vibrant Southport Corridor. This turnkey investment property features three charming and sun-filled units: Unit 1 offers 2 bedrooms and 1 bathroom, while Units 2 and 3 each feature 3 bedrooms and 1 bathroom. All units boast great natural light, spacious layouts, and access to large outdoor decks. Recent improvements include a new roof installed in 2022 with transferable warranties, updated windows, and new copper piping installed on the first floor. Additional features include basement laundry and a 2-car garage that was rebuilt within the last five years. The garage is not currently leased to tenants and provides additional income potential through rentals during Cubs games and concerts. All units are tenant-occupied with leases in place through 2027, making this a true armchair investment in an unbeatable A+ location with consistent rental demand. Explore the property in 3D by clicking the virtual tour button and walk through every detail from the comfort of your home.

1341 W Eddy Street, Chicago

$1,400,000

Rare opportunity to house hack in prime Lakeview with this well-maintained 4-unit building consisting of all two-bedroom, one-bathroom apartments. The owner's unit has been completely rehabbed and is ready for its next occupant, featuring high-end, condo-quality finishes, a brand-new kitchen and bathroom, a king-size bedroom, in-unit laundry, new high-end soft-close cabinetry, quartz countertops, and an elevated tile backsplash - creating the ideal setup for an owner-occupant looking to offset their mortgage. For investors, the owner's unit offers strong rental potential on its own, with projected rents of $3,200+ per month, leading to a projected cap rate of 7%. All units feature central heating and air conditioning. Three units have private outdoor space. Two units feature in-unit laundry with free common laundry in the basement for the others. The building sits on a south-facing corner lot, which provides an abundance of natural light as well as a wide building footprint that is evident in the large bedroom sizes. Additional features include a two-car garage and dedicated storage space for each unit, all located just steps from CTA transit, the Lakefront Trail, parks, restaurants, and everything Lakeview has to offer.

8 Beds ⋅ 4 Baths ⋅ 12649632 MLS ⋅ CLOSED Status

Rare opportunity to house hack in prime Lakeview with this well-maintained 4-unit building consisting of all two-bedroom, one-bathroom apartments. The owner's unit has been completely rehabbed and is ready for its next occupant, featuring high-end, condo-quality finishes, a brand-new kitchen and bathroom, a king-size bedroom, in-unit laundry, new high-end soft-close cabinetry, quartz countertops, and an elevated tile backsplash - creating the ideal setup for an owner-occupant looking to offset their mortgage. For investors, the owner's unit offers strong rental potential on its own, with projected rents of $3,200+ per month, leading to a projected cap rate of 7%. All units feature central heating and air conditioning. Three units have private outdoor space. Two units feature in-unit laundry with free common laundry in the basement for the others. The building sits on a south-facing corner lot, which provides an abundance of natural light as well as a wide building footprint that is evident in the large bedroom sizes. Additional features include a two-car garage and dedicated storage space for each unit, all located just steps from CTA transit, the Lakefront Trail, parks, restaurants, and everything Lakeview has to offer.

1900 W Oakdale Avenue, Chicago

$799,000

Exceptional investment opportunity in the heart of the highly sought-after Wrigleyville area! Located within the Wrigley zone, this property is currently mid-renovation and offers incredible upside for investors, developers, or owner-occupants looking to finish a project to their vision. The property is framed and ready for completion as a 4-bedroom, 2 full bath layout with flexibility to configure as a two-unit building or mixed-use residential/commercial property. Major work has been started, allowing the next owner to step in and complete the design and finishes. Additional highlights include a 2-car garage with a rooftop deck above, offering valuable outdoor living space rarely found in the area. Situated on bustling Ashland Avenue, the location provides excellent visibility and proximity to dining, shopping, transit, and all the energy of the Wrigleyville neighborhood. Whether you choose to finish and hold as an income-producing property, create a multi-unit investment, or design a unique live/work space, the possibilities here are substantial. Bring your contractor and ideas-this is a prime value-add opportunity in one of Chicago's most vibrant neighborhoods. New framing throughout. Architectural drawings available upon request. Check with alderman office for all zoning inquires.

4 Beds ⋅ 2 Baths ⋅ 12640628 MLS ⋅ CONTINGENT Status

Exceptional investment opportunity in the heart of the highly sought-after Wrigleyville area! Located within the Wrigley zone, this property is currently mid-renovation and offers incredible upside for investors, developers, or owner-occupants looking to finish a project to their vision. The property is framed and ready for completion as a 4-bedroom, 2 full bath layout with flexibility to configure as a two-unit building or mixed-use residential/commercial property. Major work has been started, allowing the next owner to step in and complete the design and finishes. Additional highlights include a 2-car garage with a rooftop deck above, offering valuable outdoor living space rarely found in the area. Situated on bustling Ashland Avenue, the location provides excellent visibility and proximity to dining, shopping, transit, and all the energy of the Wrigleyville neighborhood. Whether you choose to finish and hold as an income-producing property, create a multi-unit investment, or design a unique live/work space, the possibilities here are substantial. Bring your contractor and ideas-this is a prime value-add opportunity in one of Chicago's most vibrant neighborhoods. New framing throughout. Architectural drawings available upon request. Check with alderman office for all zoning inquires.

3636 N Ashland Avenue, Chicago

$1,610,000

GREAT OPPORTUNITY FOR THE ADD-VALUE INVESTOR, LIVE-IN OWNER, OR SINGLE-FAMILY CONVERSION. RARE EXTRA-WIDE 37.5 x 124 LOT (ZONED R3). CERTIFIED / LEGAL 3-FLAT. This professionally managed building offers strong potential throughout including duplex-up or duplex-down configurations or expansion from the rear to create a larger single-family home making this an exceptional redevelopment opportunity on an oversized lot. Significant value-add potential includes updates to increase rental income and overall property value. Two-car garage with possible room to add a third parking space provides additional flexibility for future use. Central air and heat on the first and second floors along with high ceilings create a bright and comfortable living experience. Buyers should verify local ordinances regarding ADU possibilities and development options. The first floor will be vacant June 1st. Tenant 2 has been in place since 2020 and Tenant 3 since 2023 both long-term occupants. Lincoln Park High School. Prime Lakeview location walk to the Red Line and Illinois Masonic Medical Center and just moments from everything the neighborhood has to offer. Please note this property is being conveyed "as-is."

7 Beds ⋅ 3 Baths ⋅ 12627838 MLS ⋅ CLOSED Status

GREAT OPPORTUNITY FOR THE ADD-VALUE INVESTOR, LIVE-IN OWNER, OR SINGLE-FAMILY CONVERSION. RARE EXTRA-WIDE 37.5 x 124 LOT (ZONED R3). CERTIFIED / LEGAL 3-FLAT. This professionally managed building offers strong potential throughout including duplex-up or duplex-down configurations or expansion from the rear to create a larger single-family home making this an exceptional redevelopment opportunity on an oversized lot. Significant value-add potential includes updates to increase rental income and overall property value. Two-car garage with possible room to add a third parking space provides additional flexibility for future use. Central air and heat on the first and second floors along with high ceilings create a bright and comfortable living experience. Buyers should verify local ordinances regarding ADU possibilities and development options. The first floor will be vacant June 1st. Tenant 2 has been in place since 2020 and Tenant 3 since 2023 both long-term occupants. Lincoln Park High School. Prime Lakeview location walk to the Red Line and Illinois Masonic Medical Center and just moments from everything the neighborhood has to offer. Please note this property is being conveyed "as-is."

1033 W Wellington Avenue, Chicago

$1,400,000

Stunning Three-Unit Investment Opportunity in the Heart of Roscoe Village. Experience the perfect blend of vintage character and modern reliability with this solidly built, professionally managed three-unit building. Situated in the highly sought-after Roscoe Village neighborhood, this property offers a rare "turn-key" opportunity for savvy investors or owner-occupants looking for a high-yield primary residence. The building features two spacious simplex units and one expansive top-floor duplex-up. Each floor is defined by a sense of scale and craftsmanship. Architectural Grandeur: Impressive very high ceilings create an airy, loft-like atmosphere throughout the building. Premium Finishes: Gleaming hardwood flooring runs through the living spaces, complementing the sturdy, traditional construction. Modern Conveniences: Every unit is equipped with NEW in-unit laundry, and most of the kitchen appliances and HVAC systems are new. Recent Capital Improvements! Rest easy knowing the heavy lifting has been done. Recent updates include brand new roof (2022) for long-term peace of mind. Complete rebuild of rear decks, featuring new wood-constructed outdoor decks and integrated fire escapes. Two-car garage parking providing essential storage and convenience. Investment & Owner-Occupant Potential. Currently generating 9,000/month in total rent, this building is a proven performer. With leases expiring in May 2026, July 2026, and March 2027, you have the flexibility to: House Hack - Move into one of the stunning units as an owner-occupant while the other two units cover a portion of your mortgage. Or, Passive Income: Maintain the current professional management and enjoy a stable, high-performing asset. Don't miss out on this impeccably maintained piece of Chicago real estate!

9 Beds ⋅ 4 Baths ⋅ 12627345 MLS ⋅ CLOSED Status

Stunning Three-Unit Investment Opportunity in the Heart of Roscoe Village. Experience the perfect blend of vintage character and modern reliability with this solidly built, professionally managed three-unit building. Situated in the highly sought-after Roscoe Village neighborhood, this property offers a rare "turn-key" opportunity for savvy investors or owner-occupants looking for a high-yield primary residence. The building features two spacious simplex units and one expansive top-floor duplex-up. Each floor is defined by a sense of scale and craftsmanship. Architectural Grandeur: Impressive very high ceilings create an airy, loft-like atmosphere throughout the building. Premium Finishes: Gleaming hardwood flooring runs through the living spaces, complementing the sturdy, traditional construction. Modern Conveniences: Every unit is equipped with NEW in-unit laundry, and most of the kitchen appliances and HVAC systems are new. Recent Capital Improvements! Rest easy knowing the heavy lifting has been done. Recent updates include brand new roof (2022) for long-term peace of mind. Complete rebuild of rear decks, featuring new wood-constructed outdoor decks and integrated fire escapes. Two-car garage parking providing essential storage and convenience. Investment & Owner-Occupant Potential. Currently generating 9,000/month in total rent, this building is a proven performer. With leases expiring in May 2026, July 2026, and March 2027, you have the flexibility to: House Hack - Move into one of the stunning units as an owner-occupant while the other two units cover a portion of your mortgage. Or, Passive Income: Maintain the current professional management and enjoy a stable, high-performing asset. Don't miss out on this impeccably maintained piece of Chicago real estate!

3115 N Oakley Avenue, Chicago

$1,050,000

An exceptional investment opportunity in the highly sought-after Roscoe Village / West Lake View location. Situated on an oversized 38 x 124 lot along tree-lined Barry Avenue, this property offers convenient access to grocery stores, dining, shopping, and public transit. This well-maintained three-flat has undergone significant recent improvements, including a gut renovation and dormer expansion of the top floor, adding a full bathroom and two additional bedrooms. The garden unit, currently in original condition, features 2 bedrooms and 1 bathroom and is leased MTM for $1,350/month to a long-term 10+ yr tenant, with strong upside potential to $2,400+ with updates. The second-floor unit, recently renovated, offers 3 bedrooms and 1 bathroom and is rented at $2,750/month. The top-floor owner's unit is configured as a spacious 4-bedroom + den, 2-bath duplex with an estimated rental potential of $4,000/month. Additional value-add opportunities include the potential to add a kitchenette to create a separate in-law suite on the upper level. A detached three-car garage, currently owner-occupied, presents further income potential of approximately $300-$400 per month, making this a rare opportunity to acquire a high-performing asset with immediate upside in one of Chicago's most desirable neighborhoods.

9 Beds ⋅ 4 Baths ⋅ 12626232 MLS ⋅ CLOSED Status

An exceptional investment opportunity in the highly sought-after Roscoe Village / West Lake View location. Situated on an oversized 38 x 124 lot along tree-lined Barry Avenue, this property offers convenient access to grocery stores, dining, shopping, and public transit. This well-maintained three-flat has undergone significant recent improvements, including a gut renovation and dormer expansion of the top floor, adding a full bathroom and two additional bedrooms. The garden unit, currently in original condition, features 2 bedrooms and 1 bathroom and is leased MTM for $1,350/month to a long-term 10+ yr tenant, with strong upside potential to $2,400+ with updates. The second-floor unit, recently renovated, offers 3 bedrooms and 1 bathroom and is rented at $2,750/month. The top-floor owner's unit is configured as a spacious 4-bedroom + den, 2-bath duplex with an estimated rental potential of $4,000/month. Additional value-add opportunities include the potential to add a kitchenette to create a separate in-law suite on the upper level. A detached three-car garage, currently owner-occupied, presents further income potential of approximately $300-$400 per month, making this a rare opportunity to acquire a high-performing asset with immediate upside in one of Chicago's most desirable neighborhoods.

2317 W Barry Avenue, Chicago

$1,005,000

Exceptional opportunity for an investor or owner live in to acquire a legal 3-unit building in a prime Lakeview location. Owned by the same family for many years, this property offers tremendous potential with two vacant units and flexibility for a buyer to update as much or as little as desired. The garden unit is vacant and offers 2 bedrooms and 1 bath. The rear portion of the lower level includes a utility room with a furnace and hot water tank, along with a common laundry area featuring a washer and dryer, utility sink, and electrical panels. The first-floor unit is currently occupied by a long-term tenant on a month-to-month lease who is expected to vacate in the near future. This unit includes 3 bedrooms, 1 bath, a spacious kitchen, dining area, and a large pantry off the kitchen. The second-floor unit is vacant and features 3 bedrooms, 1 bath, a large living room, dining room, and kitchen. The top floor provides attic storage and an additional hot water tank. Lot size: 25' x 97.5' SELLING AS IS

8 Beds ⋅ 3 Baths ⋅ 12615095 MLS ⋅ CLOSED Status

Exceptional opportunity for an investor or owner live in to acquire a legal 3-unit building in a prime Lakeview location. Owned by the same family for many years, this property offers tremendous potential with two vacant units and flexibility for a buyer to update as much or as little as desired. The garden unit is vacant and offers 2 bedrooms and 1 bath. The rear portion of the lower level includes a utility room with a furnace and hot water tank, along with a common laundry area featuring a washer and dryer, utility sink, and electrical panels. The first-floor unit is currently occupied by a long-term tenant on a month-to-month lease who is expected to vacate in the near future. This unit includes 3 bedrooms, 1 bath, a spacious kitchen, dining area, and a large pantry off the kitchen. The second-floor unit is vacant and features 3 bedrooms, 1 bath, a large living room, dining room, and kitchen. The top floor provides attic storage and an additional hot water tank. Lot size: 25' x 97.5' SELLING AS IS

1042 W Barry Avenue, Chicago

$955,000

Exceptional two-flat in Southport Corridor that exudes pride of ownership. This Chicago classic sits on an oversized lot and features two large 3 bedroom / 1 bath units with central air and 2 car garage parking. Located within walking distance of the best of Southport Corridor and Roscoe Village, these two units offer the ability to hold the property as a rental or owner-occupy. You'll enter this all-brick building through a side entrance with a vestibule bedecked with a classic mosaic tiling floor. The first floor unit offers beautiful original built-ins surrounding a wood fireplace, wood flooring throughout and a front sun porch. This unit also features 3 large bedrooms, one offering flexibility as a den / bedroom / office, complete with ample closet space and a bath. A very large dining room is capped off by a thoughtful kitchen with a large walk in pantry and built in eating area. The top floor offers a similar floor plan with the same built-ins and wood flooring throughout. However, this former owner's unit comes with in-unit laundry, 2 closets in the primary, an air tub in the bath as well as a heated towel rack. Additionally, the top floor unit's kitchen has been opened up to create a bright, light-filled kitchen and dining space. A walk in pantry off the kitchen is where the in-unit stackable laundry resides. An unfinished basement with laundry for the first floor unit offers extensive storage and the opportunity to duplex down the first floor unit in the future. Capping off this home is a large backyard space with grass and garden beds. Both units also come with garage parking in the detached garage off of the backyard. Ideally located in the Southport Corridor, this home offers easy access to public transit, the bars and restaurants in the area as well as the best of city living.

6 Beds ⋅ 2 Baths ⋅ 12617239 MLS ⋅ CLOSED Status

Exceptional two-flat in Southport Corridor that exudes pride of ownership. This Chicago classic sits on an oversized lot and features two large 3 bedroom / 1 bath units with central air and 2 car garage parking. Located within walking distance of the best of Southport Corridor and Roscoe Village, these two units offer the ability to hold the property as a rental or owner-occupy. You'll enter this all-brick building through a side entrance with a vestibule bedecked with a classic mosaic tiling floor. The first floor unit offers beautiful original built-ins surrounding a wood fireplace, wood flooring throughout and a front sun porch. This unit also features 3 large bedrooms, one offering flexibility as a den / bedroom / office, complete with ample closet space and a bath. A very large dining room is capped off by a thoughtful kitchen with a large walk in pantry and built in eating area. The top floor offers a similar floor plan with the same built-ins and wood flooring throughout. However, this former owner's unit comes with in-unit laundry, 2 closets in the primary, an air tub in the bath as well as a heated towel rack. Additionally, the top floor unit's kitchen has been opened up to create a bright, light-filled kitchen and dining space. A walk in pantry off the kitchen is where the in-unit stackable laundry resides. An unfinished basement with laundry for the first floor unit offers extensive storage and the opportunity to duplex down the first floor unit in the future. Capping off this home is a large backyard space with grass and garden beds. Both units also come with garage parking in the detached garage off of the backyard. Ideally located in the Southport Corridor, this home offers easy access to public transit, the bars and restaurants in the area as well as the best of city living.

1539 W Addison Street, Chicago