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$300,000
6 Beds 4 Baths 12738426 MLS CONTINGENT Status
Endless possibilities await at this unique Chicago property featuring a classic brick 2-unit with a detached coach house, offering exceptional flexibility for investors, owner-occupants, or multi-generational living. The front building features a new roof (2026), two spacious 2-bedroom, 1-bath residences filled with natural light and vintage charm, while the separate coach house provides a private 1-bedroom, 1-bath living space with its own entrance. Set on a generously sized lot, the property also offers a 2-car garage, private patio, and a fenced yard, creating rare outdoor space that's hard to find in the city. Whether you're looking to generate multiple income streams, live in one unit while renting the others, or add value over time, this property delivers incredible potential. Conveniently located near schools, parks, shopping, restaurants, public transportation, and expressways, it offers easy access to everything the city has to offer.

2639 S Trumbull Avenue, Chicago

$524,900
6 Beds 3 Baths 12738231 MLS ACTIVE Status
CLASSIC CHICAGO BRICK 2-FLAT WITH GARDEN UNIT - EXCELLENT INVESTMENT OR OWNER-OCCUPANT OPPORTUNITY! This well-maintained brick building in desirable West Humboldt Park features 3 spacious 2-bedroom, 1-bath apartments with large formal dining rooms, generous-sized bedrooms, beautiful hardwood floors, and separate utilities. The finished garden unit offers 2 bedrooms, 1 bathroom, (legality of the garden unit is not warranted), making it ideal for extended family or additional rental income. The property has been carefully maintained with three gas meters, and three separate electrical panels. Conveniently located near CTA transportation, shopping, schools, and neighborhood amenities. The building could benefit from some TLC, but it offers tremendous value, solid cash-flow potential, and long-term appreciation. Taxes do not reflect any exemptions. Don't miss this outstanding investment opportunity!

1543 N Avers Avenue, Chicago

$435,000
6 Beds 3 Baths 12736217 MLS ACTIVE Status
Solid brick duplex-down in Humboldt Park positioned for measurable value appreciation. Delivered vacant at closing with 3BD/2BA duplex-down and 2BD/1BA upper. Recent kitchen updates featuring new cabinets and appliances (2 years installed). Generous floor plans and strong structural bones create flexibility for cosmetic upgrades that will meaningfully enhance appeal and income potential. This is a straightforward value-add opportunity in a market with demonstrated momentum. Humboldt Park rents and property values continue to climb alongside active neighborhood investment and Chicago Avenue retail expansion. Transit access and proximity to parks strengthen tenant appeal and long-term appreciation trajectory. Whether positioned for immediate income or staged renovation for rental premium, the fundamentals are solid: strong structure, proven market demand, and clear upside capture in an expanding corridor. Perfect for seasoned portfolio builders seeking below-market entry with near-term equity gain, or discerning first-time investors ready to execute a disciplined value-add strategy. Close to transit and emerging commercial anchors. As-is sale, NOTE PROPERTY NEEDS WORK. What matters is execution, and this asset delivers flexibility to do it your way.

845 N Avers Avenue, Chicago

$559,000
6 Beds 2 Baths 12737214 MLS PRICE CHANGE Status
Nestled on a beautiful tree lined street, this charming home has 6-bedrooms and 2 Full baths. With 3,256 square feet of living space, this home is move in ready! Incredibly spacious with flexibility to fit a variety of living needs. With room for everyone, the possibilities are endless. There's an open Kitchen with Eating area. 2nd floor has numerous bedrooms, a den and office space, along with a walk-in attic storage area and a whole house fan. The inviting backyard offers a 12x32 ft wood deck with a retractable canopy...a great place to entertain, BBQ, have your morning coffee or relax at the end of the day. Bring your ideas for a 30 x 23 unfinished Basement which also has a 15x20 laundry area and a 15 x13 workshop area. Dual furnace/AC units were installed in 2025. Seller will leave the TV in the kitchen, treadmill, table saw, desk in the basement, china cabinet in the dining room and the day bed on the second floor.

6118 W Grace Street, Chicago

$1,275,000
8 Beds 3 Baths 12737803 MLS CONTINGENT Status
Set on one of Roscoe Village's beautiful tree-lined streets, this extraordinary and rarely available greystone is anything but typical. With a distinctive layout, oversized lot, detached greystone garage, finished studio space, and an abundance of original architectural character, this property offers a level of flexibility that is incredibly hard to find. Located in the highly sought-after Audubon School District, it is an exceptional opportunity for a single family home, owner-occupant investor, or multi-generational household. Owned and lovingly maintained by the same owner for more than 20 years, the main residence encompasses the first and second floors. Each floor features 3 bedrooms, 1 bathroom, a formal living room, formal dining room, and a beautiful custom wood-burning fireplace. Original details throughout the home include rich oak millwork, hardwood flooring, stained-glass accents, oversized windows, and spacious rooms that showcase the scale and craftsmanship of a bygone era. The kitchen was thoughtfully renovated in 2016 and features custom cabinetry, stone countertops, stainless steel appliances, and a large center island that creates an inviting gathering space. The bathroom was updated in 2021, providing a fresh complement to the home's classic architectural details. The garden apartment adds another layer of flexibility and potential. Currently configured as a 2-bedroom, 1-bath residence, it includes a full kitchen, comfortable living space, and excellent storage. The apartment was previously used as a 3-bedroom layout, offering additional possibilities for future use. One of the property's most unusual features is the detached greystone garage. Above the garage, a finished loft currently serves as a fitness studio and is already plumbed for a bathroom. Whether envisioned as a private office, art or creative studio, gym, workshop, guest space, or future finished living area, this bonus space provides tremendous potential. The property also includes a separate carport and an oversized yard with plenty of room for outdoor entertaining, gardening, recreation, or simply enjoying the space. The home's substantial construction is further highlighted by approximately 12-inch-thick limestone walls, reflecting the quality, permanence, and craftsmanship characteristic of Chicago's historic architecture. And the location is hard to beat! Just two blocks south of the popular Roscoe Street corridor, you'll be close to neighborhood restaurants, cafes, parks, boutique shopping, and everyday conveniences, while still enjoying the peaceful residential atmosphere of this sought-after pocket of Roscoe Village. Properties with this combination of architectural character, scale, outdoor space, additional living space, and flexibility rarely come to market. A truly special opportunity to own a distinctive piece of Roscoe Village with the potential to adapt to a variety of lifestyles and investment strategies.

3248 N Oakley Avenue, Chicago

$600,000
9 Beds 3 Baths 12737828 MLS ACTIVE Status
This condo-like gated 3-unit brick building in desirable South Shore is perfect for the right homebuyer or investor. All 3 spacious apartments feature 3 large bedrooms, formal dining rooms, and beautifully restored hardwood floors. Recent updates include separate heating systems and water heaters, new roof on both the apartment building and garage, rebuilt back porch, new copper and waste plumbing lines, updated electrical, and new flooring and windows. Updated kitchens feature quartz countertops and stainless steel appliances, while all bathrooms have been refreshed with new fixtures and tile, including jetted tubs. Each unit now also has its own washer/dryer hookups and central A/C. The full basement offers excellent value-add potential. The property is located within an approved zoning area to add a legal 4th unit in the basement, which already has the required ceiling height as well as both front and rear entrances. The basement also offers additional storage and income potential. There is 1 garage space per unit. Conveniently located near Rainbow Beach, the Obama Library, public transportation, places of worship, schools, restaurants, and shopping. A great opportunity for an investor or owner looking to maximize rental income and future potential. Schedule your appointment today!

7641 S Phillips Avenue, Chicago

$415,000
6 Beds 3 Baths 12737523 MLS ACTIVE Status
Stunning, fully renovated brick 2-flat offering the perfect blend of timeless Chicago character and modern luxury! Whether you're an owner-occupant looking to help out your mortgage or an investor seeking a turnkey income-producing property, this beautifully updated building checks every box. Each spacious unit has been thoughtfully renovated with gleaming hardwood floors, recessed lighting, and an open, light-filled layout. The modern kitchens feature espresso shaker cabinetry, granite countertops, stainless steel appliances, subway tile backsplashes, and abundant cabinet space, creating an ideal setting for everyday living and entertaining. The expansive living rooms showcase beautiful bay windows that flood the space with natural light, while the generously sized bedrooms and updated bathrooms provide both comfort and style. Major improvements throughout offer peace of mind, making this a truly move-in-ready investment. Situated on a quiet, tree-lined street, the property offers easy access to public transportation, major expressways, parks, schools, shopping, and dining. Conveniently located near the University of Chicago, the future Obama Presidential Center, and several ongoing neighborhood revitalization projects, this is an exceptional opportunity to own in one of Chicago's rapidly appreciating South Side communities.

8019 S Eberhart Avenue, Chicago

$499,999
8 Beds 5 Baths 12737544 MLS ACTIVE Status
Welcome to this exceptional Garfield Ridge home offering the perfect blend of space, comfort, accessibility, and convenience! Ideally located in one of Chicago's most sought-after neighborhoods, this impressive residence is just minutes from Chicago Midway International Airport, I-55, shopping, restaurants, parks, schools, and so much more. Designed with space in mind, this remarkable home features **9 bedrooms - 8 above grade and 1 on the lower level-along with 5 full bathrooms, making it an outstanding opportunity for large or multi-generational households. Thoughtfully designed to accommodate a variety of lifestyle needs, this handicap-accessible home offers enhanced accessibility and ease of mobility throughout, providing comfort and convenience for residents and guests alike. Inside, you'll find generous living spaces, including a welcoming family room that's perfect for relaxing or gathering with family and friends. The dedicated bar and entertainment area creates the perfect setting for hosting game nights, holidays, and special occasions. Step outside to your own backyard retreat featuring a spacious **outdoor deck overlooking an above-ground pool, offering the ideal space to enjoy summer days, entertain guests, or simply unwind after a long day. Combining exceptional living space, accessibility, and an unbeatable Garfield Ridge location near Midway Airport, I-55, shopping, dining, and other local amenities, this one-of-a-kind home offers endless possibilities. Whether you're searching for room to grow, accommodations for multi-generational living, or a home designed with accessibility in mind, this property is ready to welcome you home. Don't miss this rare opportunity-schedule your private showing today! Property sold as is.

5728 S Parkside Avenue, Chicago

$975,000
6 Beds 4 Baths 12735799 MLS CONTINGENT Status
Rich with original architectural detail and impeccably maintained, this truly special Buena Park brick multi-unit offers an incredible opportunity to own a piece of Chicago history. Nestled on an oversized 35 x 150 lot, this building boasts beautiful millwork, original stained glass and timeless vintage details that are complemented by incredible natural light throughout. Each of the two spacious units offers three bedrooms and 1.5 bathrooms with a gracious and highly functional layout. Either would make a fabulous owner's unit or rent easily! A true foyer opens into a large front living room where oversized windows bathe the space in natural light. The stunning formal dining room showcases beautiful original millwork, stained glass and a built-in china hutch, then flows into a gorgeous sunroom, creating the perfect home office, reading room or peaceful additional living space. Three generously sized bedrooms offer wonderful closet space while the rear kitchen features a large pantry and access to an enclosed back staircase providing even more storage. Outside, lush landscaping and mature trees create a truly beautiful backyard oasis. A brick one-car garage plus a two-car parking pad offers parking for up to three cars and excellent additional rental income potential. The lower level provides even more possibilities and could potentially be duplexed into the first-floor residence or renovated as a separate non-conforming living space. It currently includes a small kitchen, large living area, bedroom and full bathroom, along with substantial rear storage, a cedar closet and laundry. All of this in coveted Buena Park, moments from neighborhood restaurants, shopping and the lakefront with convenient access to the Wilson Red and Purple Line station, Sheridan Red Line station and Lake Shore Drive. A rare opportunity to own an exceptionally maintained vintage property filled with character, flexibility and true Chicago charm.

4327 N Kenmore Avenue, Chicago

$5,450,000
6 Beds 9 Baths 12737336 MLS ACTIVE Status
Rare opportunity to own an impeccably maintained single-family residence on Lake Shore Drive, situated on an expansive 34' x 134' lot with approximately 9,000 square feet under roof. This exceptional home offers 7 bedrooms and 7.5 baths and features multiple outdoor living spaces, with 30' x 20' garage rooftop terrace with a custom outdoor kitchen-ideal for entertaining. A dramatic foyer welcomes you into the main level, which features a gourmet kitchen, great room, and a striking living area with soaring 20+ foot ceilings, a gas fireplace, and a dining space overlooking Lake Shore Drive. The kitchen is appointed with custom white cabinetry, natural stone countertops, professional-grade appliances, a dedicated coffee and beverage nook, and a built-in breakfast banquette. A striking custom double staircase connects the upper levels. The second-floor features three light-filled ensuite bedrooms with custom-built-in storage. The third floor is home to a refined primary suite with custom millwork, a fireplace, and a tucked-away sitting area. The spa-inspired primary bath features an oversized rain and steam shower, a soaking tub, dual vanities with Calacatta marble countertops, and heated marble floors. A spacious dressing room features a center island. An additional ensuite bedroom and a laundry room complete this level. The top floor showcases exceptional custom woodwork and offers a large bar and entertainment lounge, a half bath, a workout room, and two rooftop decks with open views. The lower level includes a family/media room, wet bar, full bath, an ensuite bedroom, ample storage, oversized refrigerator and freezer capacity, and a mudroom with direct access to the 3-car garage. Additional highlights include a Control4 audio system, an elevator, individual HVAC zones, a security system, an irrigation system, and outdoor snow-melt. You have secure private alley access to a 3-car attached garage.

3026 N Lake Shore Drive, Chicago

$7,495,000
6 Beds 9 Baths 12737250 MLS ACTIVE Status
Rare opportunity to own an impeccably maintained single-family residence on Lake Shore Drive, situated on an expansive 64' x 200' lot with approximately 9,000 square feet under roof. This exceptional home offers 7 bedrooms and 7.5 baths and features multiple outdoor living spaces, including a Sport Court, a 30' x 25' terrace, and a 30' x 20' garage rooftop terrace with a custom outdoor kitchen-ideal for entertaining. A dramatic foyer welcomes you into the main level, which features a gourmet kitchen, great room, and a striking living area with soaring 20+ foot ceilings, a gas fireplace, and a dining space overlooking Lake Shore Drive. The kitchen is appointed with custom white cabinetry, natural stone countertops, professional-grade appliances, a dedicated coffee and beverage nook, and a built-in breakfast banquette. The seamless indoor-outdoor layout opens to a pergola-covered entertainment terrace with lounge seating and a fire pit, offering direct access to the backyard and an integrated sports court. A striking custom double staircase connects the upper levels. The second-floor features three light-filled ensuite bedrooms with custom-builtin storage. The third floor is home to a refined primary suite with custom millwork, a fireplace, and a tucked-away sitting area. The spa-inspired primary bath features an oversized rain and steam shower, a soaking tub, dual vanities with Calacatta marble countertops, and heated marble floors. A spacious dressing room features a center island. An additional ensuite bedroom and a laundry room complete this level. The top floor showcases exceptional custom woodwork and offers a large bar and entertainment lounge, a half bath, a workout room, and two rooftop decks with open views. The lower level includes a family/media room, wet bar, full bath, an ensuite bedroom, ample storage, oversized refrigerator and freezer capacity, and a mudroom with direct access to the 3-car garage. Additional highlights include a Control4 audio system, an elevator, individual HVAC zones, a security system, an irrigation system, and outdoor snow-melt. In addition to the 3-car garage, the property offers two outdoor parking spaces with gated, secure alley access

3024 N Lake Shore Drive, Chicago

$449,000
6 Beds 3 Baths 12734070 MLS CONTINGENT Status
Beautifully updated two-unit building in Chicago's desirable Woodlawn neighborhood, offering an excellent opportunity for both investors and owner-occupants. This well-maintained property features spacious units, modern updates, and flexible living arrangements. The duplexed-down main-level unit offers 4 large bedrooms and 2 full baths, while the upper-level unit features 3 bedrooms and an updated full bath. Both units offer bright, inviting living spaces, generous bedrooms, ample storage and renovated finishes throughout. The refreshed eat-in kitchens feature breakfast nooks, newer cabinetry, modern quartz countertops, stainless-steel appliances, and custom tiled backsplashes creating a clean, contemporary feel. Large windows fill the units with natural light, while updated flooring throughout adds to their move-in appeal. Classic Chicago architecture blends seamlessly with modern updates, creating a property that is both charming and practical. Ideally located near public transportation, parks, shopping, restaurants, and major roadways, this property provides convenient access to surrounding neighborhoods and downtown Chicago. Its proximity to the University of Chicago, Jackson Park, and the Obama Presidential Center further enhances its appeal. Whether you're looking to expand your investment portfolio or live in one unit while generating rental income from the other, this versatile property is an opportunity worth exploring.

7026 S Eberhart Avenue, Chicago

$4,995,000
6 Beds 8 Baths 12737324 MLS ACTIVE Status
The Lincoln Street Bath House is one of Chicago's most extraordinary and versatile residential offerings. This historical masterpiece seamlessly blends modern luxury with iconic neoclassical architecture. Spanning approximately 10,000 square feet across two-and-a-half city lots, this one-of-a-kind, highly adaptable property presents a rare opportunity for multi-generational living, live/work functionality, event hosting, and income-producing potential - all within an exceptionally private setting. Originally transformed from a historic bath house into a spectacular private residence, the home offers dramatic scale and unforgettable design at every turn. A soaring, light-filled great room with designer lighting, state-of-the-art A/V, and expansive entertaining spaces creates the perfect backdrop for both intimate daily living and large-scale gatherings. The sleek stainless-steel chef's kitchen anchors the home with modern functionality. The luxurious primary suite serves as a peaceful private retreat with a freshly updated en-suite bathroom- offering a serene escape from the energy of city living. Thoughtfully designed for flexibility, the lower-level features two beautifully appointed furnished units ideal for extended family, guests, au pair quarters, home office suites, or income-producing rentals. Whether accommodating multiple generations under one roof or offsetting ownership costs with rental income, the property offers an incredibly rare level of adaptability for today's evolving lifestyles. The home's sprawling layout and private compound-like feel also make it uniquely suited for creatives, entrepreneurs, collectors, entertainers, or anyone seeking substantial live/work capabilities without sacrificing luxury or discretion. Outside, the professionally landscaped grounds offer extraordinary entertaining potential with custom pavers, integrated lighting, outdoor kitchen, full bar, and expansive green space perfect for hosting unforgettable events or enjoying quiet moments surrounded by nature. Beyond its architectural pedigree and exceptional versatility, the property embraces sustainable luxury with environmentally conscious geothermal systems delivering energy-efficient living rarely found at this scale. Convenient attached garage parking plus additional exterior spaces complete this truly singular offering. The Lincoln Street Bath House is far more than a home - it is a private urban sanctuary, an investment opportunity, and a living work of art unlike anything else in Chicago.

1019 N Wolcott Avenue, Chicago

$899,000
9 Beds 6 Baths 12736649 MLS ACTIVE Status
Discover timeless Chicago architecture in this stately three-unit greystone located in the heart of Bronzeville. Showcasing the distinctive Romanesque style-one of Chicago's most recognized architectural traditions-this classic building blends historic character with modern convenience. Each spacious residence features 3 bedrooms, 2 full bathrooms, and a separate formal dining room offering generous living space ideal for both everyday living and entertaining. The thoughtfully designed interiors include hardwood floors, soaring ceilings, in-unit laundry, and abundant natural light. Spacious kitchens are appointed with granite countertops, ample cabinetry, and room for a breakfast table or casual dining. Each unit is separately metered and equipped with its own furnace and water heater, providing convenience, efficiency, and simplified property management. The first and second-floor units are occupied by long-term tenants, providing immediate, stable rental income. The third-floor unit is currently vacant, presenting an ideal opportunity for an owner-occupant to move right in while benefiting from rental income, or for an investor to lease the unit and maximize the property's income potential. Step outside to enjoy brand-new rear porches, providing each unit with a private outdoor deck. The property also features gated parking with one dedicated parking space for each unit, offering added convenience for residents. The full basement provides additional value with the potential to create an additional dwelling unit or expand the property's existing living space. Situated on a picturesque tree-lined street, this exceptional investment or owner-occupant opportunity is just minutes from public transportation, neighborhood parks and green spaces, and the vibrant dining, shopping, and cultural attractions of nearby Hyde Park and South Loop. Whether you're looking to expand your investment portfolio or own a piece of Chicago's architectural heritage, this exceptional Bronzeville greystone offers the perfect blend of historic character and modern amenities. Enjoy stable rental income or sell later as individual condos. An outstanding opportunity for both investors and owner-occupants.

4408 S Michigan Avenue, Chicago

$130,000
8 Beds 3 Baths 12737206 MLS ACTIVE Status
Great opportunity to complete and customize this spacious West Garfield Park multi-unit property. Major improvements have already been started, with several rooms featuring fresh paint, updated windows, and new finishes, while additional renovations remain to unlock the property's full potential. The home offers generous living space, large bedrooms, a full basement for storage or future expansion possibilities, and a fenced yard. The upper level showcases significant progress, while the main level, kitchen, and bathrooms provide an excellent opportunity for a buyer or investor to finish to their own specifications. Whether you're looking to renovate and occupy, add to your investment portfolio, or create long-term rental income, this property presents tremendous value with much of the heavy lifting already underway. Conveniently located near parks, schools, public transportation, and expressways. Sold as-is. Bring your vision and finish this promising project.

4150 W Carroll Avenue, Chicago

$465,000
9 Beds 4 Baths 12728571 MLS PENDING Status
Spacious brick three-flat offering three 3-bedroom apartments, a partially finished basement with an additional bathroom and a 3-car detached garage. Two units are currently occupied, while the vacant third-floor apartment provides an excellent opportunity for an owner-occupant or investor seeking additional rental income. Numerous capital improvements have been completed, including replacement of the original boiler with three individual gas forced-air furnaces, upgraded electrical wiring, extensive plumbing improvements featuring copper supply lines with individual unit shutoff valves, a newer 75-gallon hot-water tank and separate gas and electric meters for each apartment. A fourth gas meter serves the building's common utilities. Additional updates include vinyl flooring throughout all three apartments, newer windows throughout much of the building, recent roof maintenance, garage repairs and a replaced main water shutoff valve. Each apartment features three bedrooms with separate living and dining rooms. The partially finished basement provides additional storage and utility space. With spacious units, separate mechanical systems and meaningful infrastructure improvements already completed, this property offers flexibility for owner-occupants and investors alike. Schedule your private tour today.

7841 S Wolcott Avenue, Chicago

$869,000
7 Beds 3 Baths 12736110 MLS CONTINGENT Status
Welcome to 2323 W. Charleston - a fantastic Bucktown opportunity with incredible potential! This spacious 2-flat offers great bones, a flexible layout, and an oversized dormered attic featuring a full bath and multiple skylights. While the property needs work, the possibilities are endless and the property is ideally suited for a single-family conversion or an investor looking to create value in one of Chicago's most desirable neighborhoods. The property also offers a unique no-setback configuration, creating the opportunity for a generous yard area between the building and garage. Located just steps from Holstein Park, with easy access to neighborhood restaurants, shopping, transportation, and all that Bucktown has to offer. Bring your architect, contractor, and vision-this is a rare opportunity to transform a property with tremendous upside into something truly special. Easy to show!

2323 W Charleston Street, Chicago

$799,999
6 Beds 3 Baths 12734609 MLS CONTINGENT Status
2826 W. Wellington Ave. is a well-maintained, brick, 3-unit, residential asset located in the heart of Chicago's desirable Avondale neighborhood. The property consists of three spacious 2-bedroom, 1-bathroom floor plans, offering investors a low-maintenance asset with immediate rental upside and no near-term capital expenditure requirements. The property features strong mechanical infrastructure, including newer individual HVAC systems and dedicated hot water heaters for each unit. Unit finishes vary, highlighted by a high-end "owner's unit" on the ground floor that provides premium finishes and immediate flexibility for an owner-occupant or top-of-market rental rates. The "owner's unit" was previously converted from 3-bedrooms to 2-bedrooms, and could easily be converted back to 3-bedrooms. All units are fully equipped with in-unit laundry. Additional value-add potential exists with the detached garage, currently owner-utilized, which can be leased to existing tenants or neighborhood residents for an estimated $250/month. Previously owner-occupied, this property represents an ideal turn-key opportunity for an investor seeking stable cash flow, low operational friction, and clear path to increase the gross income. Located steps from key transit options, residents enjoy fast access to the CTA Blue Line (Belmont and Logan Square stations) and I-90/94 (Kennedy Expressway), along with the vibrant retail and dining corridors along Milwaukee, Belmont, and California Avenues.

2826 W Wellington Avenue, Chicago



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