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$1,230,000
8 Beds 3 Baths 12595065 MLS CLOSED Status
*MULTIPLE OFFERS RECEIVED *A RARE chance to own a timeless piece of Chicago history in one of the city's most sought-after neighborhoods. This striking 1897 greystone 3-flat is perfectly positioned on a quiet, tree-lined block just a few minutes from the buzz of the SOUTHPORT CORRIDOR and all the dining, nightlife, and energy along Belmont & Clark. ***Fully leased and meticulously cared for by the same owner for the past 30 YEARS, this building presents FLEXIBLE OPPORTUNITIES for a variety of buyers. Owner-occupants can live in one unit while offsetting their mortgage with rental income from the others. End-users and rehabbers can bring their design vision to update units and maximize rents. Developers will appreciate the solid 1897 construction and potential for condo conversion or a single-family home transformation. Or, turn this timeless beauty into a multi-generational home for decades to come. ***The classic greystone charm is complemented by TIMELESS architectural DETAILS, generous 10ft ceiling height and original built-ins, along with modern peace of mind including a BRAND NEW ROOF (2025), well-maintained exterior, and refreshed entry & common hallways. ***The property also features a 2-car GARAGE (each leased for $175/month), back yard, basement laundry room and additional common storage space. ***This A+ location offers easy access to public transportation, grocery stores, Southport shops, walk to Wrigley, plus an endless array of bars and restaurants, along with convenient access to the lakefront. With immediate rental income and STRONG UPSIDE potential, this VINTAGE GEM delivers the perfect combination of history, location, and flexibility. Truly a rare opportunity in one of Chicago's most beloved neighborhoods. (Please see additional documents tab for lease info, apartment/parking rent roll & operating expenses. Note the property is being sold AS-IS)

1322 W Barry Avenue, Chicago

$935,000
4 Beds 3 Baths 12588842 MLS CLOSED Status
Welcome to this classic Lakeview / North Center Greystone 2 flat . Vintage charm abounds as both units boast solid hardwood floors, original woodwork, gorgeous built in hutches, a separate dining room, and bedrooms big enough to fit a queen size bed. The 2nd floor unit also offers a charming gas fireplace to cozy up to, a rear deck perfect for morning coffee, summer nights and enjoying the sunshine; a sizable walk-in closet, and a den/office area with built in cabinetry. This building is an excellent opportunity for an owner occupant with a rental unit downstairs, a conversion to a single family home, or to use strictly as an investment property. The building has central heat and air, separate utilities, newer windows, shared laundry in the basement, a full back yard, and garage. The seven foot basement height gives potential to duplex down. The first floor unit is 2 beds, 1 bath. Second floor unit is 2 beds /1.1 bath with a den/office area. The building is tucked away on a quiet street in an excellent location- a quick commute to the Addison brown line, and a short trip in any direction to the many shopping and dining options in Lakeview and North Center!

3750 N Hermitage Avenue, Chicago

$1,355,000
9 Beds 3 Baths 12584580 MLS CLOSED Status
Handsome red brick 3 flat building in the heart of Wrigleyville on extra wide 30' lot boasts 3 legal units plus unfinished basement. All three units have 3 bedrooms and one bath, hardwood floors, separate living and dining rooms, updated kitchens and baths, tall ceilings, bay windows, pantries or enclosed porch space. Blaine school district. Parking includes 2 car garage plus exterior space. New tear off roof and tuck pointing in 2016. New windows units 1 and 3 in 2016, unit 2 in 2023. Units 1 and 3 have central air. Newer water heaters (3), New HVAC unit 1 in 2022, unit 3 2016. Annual rental income 86,940. Common utilities approximately 1976 and insurance approximately 3550 annually. Basement ceiling height approximately 6'10. Leases end 5/31/2026, 6/30/2026, 7/31/2026. Please see seller representations in the FAQ in additional information tab.

3732 N Racine Avenue, Chicago

$1,520,000
7 Beds 7 Baths 12597836 MLS CLOSED Status
Exceptional investment opportunity in the heart of Lakeview! This 4-unit property offers a versatile mix ideal for both investors and owner-occupants. The front building features two units, including a stunning duplex-up that lives like a single-family home. The top unit offers 3 bedrooms and 2.5 baths, complete with in-unit laundry and individual HVAC-perfect for an owner-occupant seeking comfort and privacy. The lower-level unit is a spacious 2 bed / 1 bath, providing solid rental income. The rear coach house adds even more value with two additional units. The first-floor unit is a 1 bed / 1 bath with generous storage space below, while the upper unit is a charming loft-style 1 bed / 1 bath plus den, filled with character and natural light.

1337 W Barry Avenue, Chicago

$900,000
4 Beds 2 Baths 12589686 MLS CLOSED Status
Charming and well-maintained 2-unit frame building with non-conforming garden apartment in a prime Roscoe Village location offering strong income potential with a projected annual income of $67,740. The property features three 2-bedroom, 1-bath units, including two above-grade units and a garden apartment. The first and second floor units offer 2 bedrooms plus a den, hardwood floors, updated kitchens, and gas forced-air heating. The garden apartment provides a spacious 2-bedroom layout with baseboard boiler heat and includes one garage parking space. Current rents are $1,895/month for Unit 1, $2,300/month for Unit 2, and $1,450/month for the garden apartment, with tenants paying their own gas and electric utilities. An additional garage parking space offers the opportunity for approximately $100/month in extra income. Recent improvements include a new tear-off roof completed in 2023 and a new water service line installed in 2026. Each unit has its own hot water tank (2020-2021), and air conditioning is tenant-provided via window units. This property offers onsite laundry, additional attic space, front and back patios and excellent long-term investment potential. Ideally located near Hamlin Park, Roscoe Village shops and restaurants, and convenient CTA access, making it attractive to both tenants and investors alike.

2118 W Fletcher Street, Chicago

$1,520,000
9 Beds 4 Baths 12587310 MLS CLOSED Status
A true Chicago beauty with incredible curb appeal and potential is on the market for the first time in over 40 years. Lovingly maintained, this 3 unit building with incredible vintage details is not to be missed. Situated on one of Lake View's most coveted blocks, this building offers an amazing opportunity for renovation or to assume a robust investment property. The top floor of the building (seen in the listing photos) is an enormous 4 bedroom / 2 bath with central heating / air and in-unit laundry. Lovingly restored millwork throughout this space, high ceilings and an abundance of light make it an ideal owner's unit. The middle floor is a 2 bedroom / 1 bath that also has in-unit laundry. Finally, the first floor unit is a 3 bedroom / 1 bath that uses coin laundry in the basement. A 2 car garage situated in the back brings in additional income. Located in the Newport Avenue District, this R5 zoned building is on a one-way street lined with other historic greystones. Situated on one of Lake View's most coveted streets the building is in the heart of it all with easy access to public transit, the bars and restaurants of both Wrigleyville and North Halsted and the Lake. Please note, this property is being conveyed "as-is." Don't miss the opportunity to own this jaw dropping property.

849 W Newport Avenue, Chicago

$1,425,000
4 Beds 4 Baths 12595235 MLS CLOSED Status
Great investment opportunity to own this money making 3-flat on a corner lot in highly desired Lakeview! Gorgeous 1st floor 2 bed/ 2 bath + den, duplex-down has lovely owners finishes with, crown molding, beautiful hardwood floors, stylish exposed brick with tons of natural light throughout, custom chef's kitchen with 42" white shaker cabinets, stainless steel appliances, mother-of-pearl backsplash, under-mount LED lighting and granite countertops with an expansive breakfast bar and nook - perfect for entertaining! The Lower-Level features high ceilings, thoughtfully designed primary suite with tons of natural light, custom windows and updated en-suite bathroom and walk-in closet. Unit 2 (1 bed/ 1 bath + den) and Unit 3 (1 bed/ 1 bath) both have great long-term tenants and updated and show very well. Major exterior renovation 2016 (new cedar siding and stonework, full landscape and hardscape, 2 car garage). Building offers additional storage, and coin laundry in the lower level (whirlpool commercial grade) plus a lovely common landscaped yard. This property is seconds from coffee shops, restaurants, grocery stores, public transit, and Southport Corridor! Unit 1- $4000 including 1 garage space. Unit 2- $2300. Unit 3- $1925. Extra Garage available for $150 per month. Coin Laundry brings in $100 per month. TOTAL RENT ROLL is $8500 per month. Broker Owned.

3034 N Greenview Avenue, Chicago

$1,251,000
8 Beds 4 Baths 12569927 MLS CLOSED Status
Fantastic investment property in prime Wrigleyville location! This 3 unit building with a non conforming basement unit. All brick building in a highly sought after Lakeview location with historically steady rents and low vacancy. Building features updated units with central air, gas forced heat, newer kitchens and baths, dishwashers, original oak trim/doors and hardwood floors. Each unit has their own laundry allowing for premium rents. Tenants pay their own utilities and the property has exterior parking available for 3 cars. Well maintained property with newer mechanicals makes this the perfect turnkey property for any investor or owner looking for the perfect house hack! Convenient Wrigleyville location puts you in walking distance to restaurants, bars & nightlife, CTA, and the lakefront. Please note neither the owner or broker make any representation of the legality of the garden unit. Sold as-is. Multiple offers - Highest and best due by 5pm 03/10/26

3343 N Sheffield Avenue, Chicago

$915,000
5 Beds 3 Baths 12583671 MLS CLOSED Status
Located on a quiet, tree-lined street in Chicago's highly desirable North Center neighborhood, 1922 W Wolfram St presents a rare opportunity to acquire a legal three-unit building blending vintage character with modern upgrades. The property features an attractive unit mix consisting of two spacious 2 bed / 1 bath units and one 1 bed / 1 bath garden unit, making it well-suited for both investors and owner-occupants. The building showcases a beautiful stone exterior that delivers timeless curb appeal, while extensive renovations completed in 2018-2019 have modernized the interiors for today's renters. Each unit offers updated kitchens with stone countertops and stainless steel appliances, complemented by hardwood floors throughout and the convenience of in-unit laundry. Major mechanical improvements include a tankless water heater, newer boiler, and mini-split HVAC systems serving each unit, providing efficient, customizable climate control. Additional features include a 1-car brick garage and well-maintained building systems, rounding out a turnkey investment in one of Chicago's most sought-after rental markets.

1922 W Wolfram Street, Chicago

$1,400,000
7 Beds 7 Baths 12581788 MLS CLOSED Status
Incredible house hack/investment opportunity in Lakeview. This beautiful legal 3 unit property boasts 3 duplexed units in 2 separate buildings. The front building containing two duplex units (both 3 Bed / 2.1 baths and 2 full baths) and one coach house also featuring a 1 bedroom duplex unit with an additional large room/den/office/studio space. All units are updated to include central heat/air as well as washer/dryer in unit, beautiful hardwood floors and renovated kitchens and bathrooms. Unique floor plans are ideal for rental potential with open concept spaces that seem closer to condo quality than the traditional multi unit. The buildings are south facing creating ample sunlight. Incredible location right off Lincoln Avenue and a few streets from Southport Corridor with numerous restaurants, coffee shops, bars and nightlife. The Paulina Brown Line just a few blocks away!

1450 W Barry Avenue, Chicago

$725,000
4 Beds 4 Baths 12551028 MLS CLOSED Status
Great Income on this Updated 2-Flat in Awesome Hamlin Park/Roscoe Village Location. Updated units rent quickly, perfect for Live-In Owner or Investor. Location is walkable to Belmont Street & downtown Roscoe Village. Two Duplexed Units feature updated Kitchens & Baths, New HW floors throughout, laundry in the Bldg and 4-car tandem parking in the back. 2nd Floor Improvements include, New Furnace & A/C (~2024) New Kitchen & Appliances (~2022), New Bathrooms (~2022), HW Flooring (~2022), Updated Electric (~2022), H2O Tank (~2021), Laundry (~2019). 1st Floor improvements include New W/D (~2023), New Appliances (~2021), H2O Tank (~2021), New Furnace & A/C (~2020), Updated Kitchen & Bathrooms (~2018). Other Bldg Improvements include some updates to Electric & Plumbing as the units were renovated, plus New Roof (~2012). Lots of New Construction on the block and in the area, great destination location, perfect for AirBnb or traditional rentals. Steps to Shopping, Dining, Nightlife, CTA, Expy and all the City has to Offer. This location is HOT!!!

3020 N Clybourn Avenue, Chicago

$1,600,000
7 Beds 3 Baths 12569466 MLS CLOSED Status
Incredible Opportunity to acquire an updated brick Legal 3-Flat Multi-Family investment property on an Oversized Lot in coveted Top Performing CPS Blaine School District!!!! This property is ideal for the Live in Owner and is Zoned RT-4 which also provides for upper bracket multi-family new development. The current apartment configuration is as follows: 2nd Floor Apartment Three Bedroom One Bathroom, 1st Floor Apartment Two Bedroom One Bathroom and Ground Level Apartment 2 Bedroom One Bathroom. Very bright and open apartment floor plans containing hardwood/tiled floors with updated finishes including stainless steel appliances, granite counters, updated cabinetry in excellent condition. Large exterior rear decks overlook an oversized rear backyard ideal for play and comfort. On site common area coin laundry and separate owner's storage shed is located in detached two car garage. Existing rents are well below market and ready for a price reset. This property is situated within walking distance to the Southport entertainment and shopping district as well as Wrigley Field. Recent Improvements include: Windows 2010, New Roof 2010-Silver Coat 2022, Boiler 2010-Updated Thermostat-2025, H2O Tank 2017, Garage Floor and Door-2019, 2nd Floor Updates 2014, 1st Floor Updates, 2016 and Ground Unit updates 2017.

1411 W Byron Street, Chicago

$1,358,000
7 Beds 4 Baths 12541721 MLS CLOSED Status
TWO CITY APPROVED UNITS WITH THE POSSIBILITY OF ADDING ONE OR TWO ADDITIONAL APPROVED UNITS. Prime Investment Opportunity! Nestled in the heart of Lakeview/Wrigleyville, this high-income, multi-unit property offers a unbeatable location just steps from Wrigley Field. Whether you're an investor looking for a lucrative rental property or a homeowner eager to live in one of Chicago's most vibrant neighborhoods, this classic Chicago apartment building is a rare find. Possible four rentable units, currently generating an impressive annual income over $140,000. This building consistently outperforms similar properties in the area thanks to its low operating expenses and highly desirable unit mix. Unit breakdown: Unit 1: 3 bed / 1 bath Unit 2: 2 bed / 1 bath Garden (G): 2 bed / 1 bath, currently renting for $2,300 per month and Attic Loft Space: a 1,000 sq ft. open-concept studio, currently renting for $2,600 per month. The apartments rent quickly and are always in demand. Additional rental income can be generated by renting out garage spaces. Individual GFA heating and AC systems. Hardwood floors, volume ceilings, custom wood molding and charming built-ins. Additional features include a rear private brick patio, 2-car garage, and on-site coin operated laundry in the basement. Nestled on tree-lined Kenmore Avenue, this property enjoys a prime location next to Wrigley Field but tucked away from the hustle and bustle. Walk to everything Wrigleyville has to offer: CTA Red Line, shops, dining, bars, and year-round entertainment.

3809 N Kenmore Avenue, Chicago

$950,000
5 Beds 4 Baths 12532955 MLS CLOSED Status
Opportunity to own a corner 3-unit building in the heart of Lakeview, ideally situated on a serene, tree-lined block. Owned and lovingly cared for by the same owner since 1984, this charming Victorian-style property offers timeless character, income potential, and versatile living options. The spacious owner's duplex-up home offering 4 bedrooms, 2 full baths, an updated kitchen, formal dining room, fireplace, enclosed sunroom, private deck, and in-unit laundry. The added kitchenette provides flexible use, including potential Airbnb income. The front first floor unit is a bright studio with hardwood floors featuring GFA heat. The rear first-floor unit features 2 bedrooms, 1 bath, updated kitchen and spacious living space. All units separately metered for electric. Duplex unit and Unit 1R are on gas boiler heat, (replaced in 2013). Enjoy a beautifully landscaped backyard, large communal deck, 2 1/2 -car garage with ample storage. Located on a quiet residential street just steps from public transit, shops, restaurants, and all that Lakeview has to offer. Whether you're an owner-occupant or an investor looking to expand your portfolio in one of Chicago's most desirable neighborhoods, this property checks every box.

1100 W Wellington Avenue, Chicago

$1,565,000
7 Beds 6 Baths 12483245 MLS CLOSED Status
**PRIME** East Lakeview CLASSIC Greystone FOUR BLOCKS from WRIGLEY - Fully Renovated 3-Unit Investment with STRONG Cash Flow! On one of East Lakeview's most picturesque tree-lined blocks, this Greystone has been updated since its purchase with LARGE units boasting spacious floor plans, large living spaces, eat-ins, separate dining rooms, updated kitchens and bathrooms, separate HVAC systems, and more. Office / den spaces can easily be converted into third bedrooms or left as bonus rooms. With all three units leased through 2026, this is a turnkey investment with very strong cash flow in one of Chicago's most desirable rental markets. Unit 1 underwent a major renovation in 2024 with approximately $28K in improvements, including all new appliances and the addition of a private in-unit washer/dryer. The basement has plentiful tenant storage, maximizing functionality, and also has the convenience of a two-car brick garage. Ideally situated just BLOCKS from the lakefront, Wrigley, and two blocks from the Red Line 'L', the building is in a prime north side location to give tenants unbeatable access to Lakeview's restaurants, shops, and nightlife. With a proven rental history, this building is an excellent investment that provides immediate stability with long-term upside in one of Chicago's most sought-after neighborhoods.

905 W Dakin Street, Chicago

$1,465,000
8 Beds 6 Baths 12461474 MLS CLOSED Status
Discover an exceptional investment opportunity or the perfect single family conversion in this stately, rehabbed Greystone located in Chicago's sought after Wrigleyville/Lakeview community. Situated on the historic Newport Avenue District, a landmark block renowned for its beautiful, intact stone fronted three flats. This building offers a classic Chicago experience with modern amenities. The building is comprised of three well maintained units. The top floor, duplex up, owner's unit, offers the scale and comfort of a single family home. Spanning the second and third floors, it features an open concept main level with a chef's kitchen, 42" cabinets, stone countertops and hardwood floors a private rear decks and a spacious bedroom and full bath. The upper level features an open style primary bedroom with a walk in closet, a large seating area and fireplace. The primary bath features double vessel sinks, a whirlpool tub and a separate steam shower. This level includes the spacious third bedroom, a full bath and it's own private rear deck. The true highlight is the rare, private 27'x22' rooftop deck, perfect for entertaining with stunning city skyline views. The first floor unit is a bright and spacious 3-bedroom, 2-bath with soaring windows, tall ceilings, and a large open kitchen. This unit has it's own private rear deck and direct access to the expansive 20'x19' deck above the garage. The garden unit, a bright 2-bedroom, 1-bath, offers direct access to the generous brick paved backyard. This property has been cared for by the live in owner for 30 years, with significant updates including plumbing and electrical, tuck-pointing (2016), a new roof (2015), and premium windows (2020). Parking for three cars adds significant value. Currently configured as a high income three flat, the building generates a total annual income of $117,600 with a net operating income of $90,822, representing a consistent 6 percent CAP rate with room for growth. This is a remarkable opportunity for a live in owner to generate a large income stream while building equity, a long term investor seeking a strong return, or a developer looking to convert it into a magnificent single family home. Located in the desirable Nettlehorst Elementary School District, this property is just steps from Wrigley Field, shopping, dining, and a short walk to the "L" train and Lake Michigan. Don't miss this chance to own a piece of classic Chicago in an unbeatable location.

902 W Newport Avenue, Chicago

$1,425,000
7 Beds 4 Baths 12477908 MLS CLOSED Status
Exceptional Lakeview/Southport 3-Flat. Located in the heart of Lakeview's desirable Southport Corridor, this all-brick 3-unit building offers a rare investment opportunity in one of Chicago's most vibrant and walkable neighborhoods. Perfect for investors and potential owner-occupants, the property combines timeless vintage charm with thoughtful modern updates. The building features two spacious 2-bedroom/1 Bath units, and a 3-bedroom, 2-bath duplex-down-each with rear decks, in-unit laundry, and individual HVAC systems (GFA/CA). Vintage details throughout include hardwood floors, crown molding, and original millwork, complemented by ongoing updates over the years. Kitchens have been renovated with granite countertops and newer appliances. All bedrooms are generously sized, and the front dens in the upper units make ideal office or workout spaces. The duplex unit includes a large lower-level family room and third bedroom, full bath, walk-in closet, and side-by-side washer/dryer. Just steps from top-rated Blaine Elementary, boutique shopping, parks, restaurants, and public transit, this property offers unmatched location, flexibility, and long-term value. (Please note pictures are from previous sale.)

3760 N Wayne Avenue, Chicago



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