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1527 E 66Th Place, Chicago
$885,000
9 Beds ⋅ 7 Baths ⋅ 12723988 MLS ⋅ ACTIVE Status
Prime Woodlawn Investment Opportunity! Invest in the growth of Chicago's historic Woodlawn neighborhood with this meticulously maintained, condo-quality 3-unit building. Perfectly positioned just blocks from the Obama Presidential Center, this turn-key property is an exceptional opportunity to owner occupy or invest, offering high-end rental income and significant long-term appreciation potential. Property Highlights: Optimal Unit Mix: Three highly desirable, spacious units, each featuring a 3-bedroom, 2-bathroom layout. Premium Floor Plans: The first-floor unit is a sprawling duplex-down, providing massive living space that lives like a single-family home. Condo-Quality Finishes: Beautiful interior details, including exposed brick walls, add character and charm to attract premium tenants while minimizing upkeep. Turn-Key Mechanicals: All major systems-including plumbing, electrical, HVAC have been modernized, and recent tuckpointing, ensuring low maintenance and peace of mind for the next owner. Unmatched Location & Upside: Situated at the epicenter of a multi-billion dollar neighborhood transformation, this building sits directly across the street from a brand-new 8-unit development, signaling strong and continuous local investment. Residents enjoy an incredible quality of life with seamless access to DuSable Lake Shore Drive, the lakefront recreation trail, the renowned Jackson Park Golf Course, the beach, and the harbor. Plus, the vibrant shopping, dining, and entertainment of nearby Hyde Park are just minutes away. Don't miss this rare chance to own a strategic, cash-flowing piece of Woodlawn's exciting future!

1527 E 66Th Place, Chicago

6140 S Eberhart Avenue, Chicago
$850,000
12634033 MLS ⋅ ACTIVE Status
This fully renovated 6-unit building in Woodlawn has been strategically repositioned to maximize income and provide long-term stability for its next owner. With strong in-place cash flow and major updates already completed, this is a true turnkey investment. Each unit is exceptionally spacious, offering 3 generously sized bedrooms along with a formal living room, separate dining room, and full kitchen-an increasingly rare layout that supports premium rents. Four of the six units feature front balconies, and all units include rear decks, adding valuable outdoor space for tenants. The property is designed for efficiency, with individual heating systems that shift a significant portion of expenses to tenants, helping to reduce owner overhead. Additional features include a full-building camera system for security and on-site laundry in the basement for tenant convenience. Located in rapidly growing West Woodlawn-one of the South Side's most promising investment corridors-the building is just minutes from the lakefront and a short bike ride to University of Chicago. Hyde Park is also just minutes away, offering tenants convenient access to dining, shopping, entertainment, and everyday essentials. Downtown Chicago is accessible in under 15 minutes by car, making this an ideal location for renters seeking space, value, and connectivity. With large 3-bedroom units driving strong rental demand, this property offers an excellent opportunity to step into immediate cash flow, continued appreciation, and long-term upside-all without the burden of renovation.

6140 S Eberhart Avenue, Chicago

6852 S Langley Avenue, Chicago
$589,000
3 Beds ⋅ 3 Baths ⋅ 12717920 MLS ⋅ ACTIVE Status
Your home should work harder for you. This brand-new construction Two Flat is perfect for first-time buyers and those seeking low-maintenance ownership with income, accessibility, affordability, or multigenerational living. Built by award-winning Greenline Homes, this high-performance, all-electric, two-unit building combines elegant design with cutting-edge building science. Every detail, from the premium Hardie Board exterior to the EV-ready garage and gated intercom security, is crafted for effortless, low-maintenance living. The primary duplex unit offers a condo-quality 2 Bedroom + 2 Bath layout upstairs with a versatile duplex to the main-level bonus room, ideal for a high-end home office, a third bedroom, or home gym. The unit also features a chef's kitchen with custom cabinetry, quartz countertops, and a premium Induction range. The stunning grade-level accessible first-floor interfaces well with the private rear yard and extra-wide garage. Both the garage and main-level unit are ADA accessible. This unit provides a spacious retreat, perfect for multi-generational living or generating high-value rental income to enhance affordability. Each Greenline Home is appointed by a designer with tastemaker-grade finishes. Embrace custom cabinetry, designer quartz, and induction cooking in a home designed for the next 100 years, not the last. With triple-pane windows for ultimate thermal comfort and a fully paid-for solar PV system, enjoy near-zero utility costs without compromising on style. Your comfort and investment in this home will last for generations. Experience a healthier, wealthier, and more comfortable lifestyle-your best life begins here. Schedule your showing today to explore Chicago's best-priced new construction.

6852 S Langley Avenue, Chicago

638 E 65Th Street, Chicago
$575,000
4 Beds ⋅ 4 Baths ⋅ 12710393 MLS ⋅ ACTIVE Status
Welcome to WOODLAWN "SAME AS" NEW CONSTRUCTION 3-STORY, 5 BEDROOM 3.5 BATH SINGLE FAMILY HOME. WITH OVER 2,000 OF ADDITIONAL NEWLY BUILT SQUARE FOOTAGE, FOR A TOTAL OF 3,808 SQFT - THIS IS A BRAND NEW HOME! This exquisite modern-style home has been completed with over 350k in expansion, redesign, renovation and is ready for the discerning Buyer seeking luxury, comfort and convenience. This is a well curated floor plan with an expansive main level, featuring new hardwood flooring throughout, 10ft ceilings, plenty of natural sunlight, separate living/dining room combo, Butler's pantry with wine cooler, walk-in kitchen pantry, half bath and storage room! However, that's not it! Keep walking and you'll notice a beautiful chef kitchen with custom-built soft close cabinetry, over-sized 11ft waterfall island with breakfast bar overhangs, Calacatta white quartz countertops with ceramic tile backsplash, professional series stainless steel appliances with double oven, eat-in breakfast nook large enough for 6-chair table, and a spacious family room! The entire second floor is a family oasis that includes primary bedroom with walk-in closet, spa-like master suite with separate soaker tub, massive shower and double vanity sinks. 3 additional bedrooms and another full bath with double vanity sinks for all the kids, laundry has been added to the 2nd floor for your convenience, dual controlled heating and cooling, and hardwood floors throughout. Can't wait to see your face drop with all the space in the basement! Drain-tile zero flooding system, vinyl flooring, an additional bedroom, full bath with more storage and utility room. The wrought iron fence and wood fenced yard provides privacy and professional landscaping brings urban oasis to life. New cement patio and sidewalk and new 2.5 car garage. This home is surrounded by new construction, The Obama Library, University of Chicago, Jackson Park Golf Course, Children's Hospital, Museum of Science & Industry and Lake Shore Beaches ALL are within a few miles away! Come take a tour and fall in love!!

638 E 65Th Street, Chicago

1009 E 61St Street, Chicago
$469,000
3 Beds ⋅ 2 Baths ⋅ 12706715 MLS ⋅ ACTIVE Status
Stunning townhome located right next to the University of Chicago campus, directly across the street from the dorms. This tri-level home features an open-concept main level with fresh paint throughout. The kitchen boasts newer stainless steel appliances and opens to a private deck-perfect for entertaining. The home includes 3 bedrooms, 2 updated bathrooms, and a 1-car attached garage. Enjoy an incredibly convenient location within walking distance of university buildings, the medical center, local restaurants, and the lakefront. Parking is a breeze with corner lot resident parking, street parking, and permit parking available. NO HOA, NO HOA, NO HOA. Close to the Metra and CTA. The roof was newly replaced. Harwood flooring was recently installed. the windows were newer. A new range hood with vent out was installed last year. Whole house repainted last year. Come check it out for yourself-you don't want to miss this one!

1009 E 61St Street, Chicago

541 E 60Th Street Unit #1A, Chicago
$99,900
2 Beds ⋅ 1 Baths ⋅ 12705485 MLS ⋅ ACTIVE Status
Great investor/buyer opportunity with this condo which is 4 blocks walking to the University of Chicago. Located in West Woodlawn. First floor with 2 bedrooms 1 bathroom. Newly painted, new laminate flooring throughout except 2 bedrooms which have new carpeting. Bathroom has new vanity and tub is re-glazed. Jewel Food Store is nearby. Conveniently located near public transportation on Cottage Grove and King Drive. Great location next door to Hyde Park. Across the street from Washington Park. Plenty of street parking. , 1 miles from the new Obama Presidential Library, short drive to the Museum of Science and Industry. This bright and inviting unit features abundant natural light, hardwood floors, in-unit laundry, separate living and dining rooms. Ideal for students, healthcare professionals, or investors, with no rental cap offering excellent income potential. Hard money lender, cash or DSCR loan! Quick closing! No FHA or conventional.

541 E 60Th Street Unit #1A, Chicago

6435 S Kenwood Avenue Unit #3S, Chicago
$290,999
3 Beds ⋅ 2 Baths ⋅ 12681156 MLS ⋅ ACTIVE Status
INVESTOR SPECIAL, TURNKEY & FULLY FURNISHED 3BR/2BA CONDO | HYDE PARK / WOODLAWN Exceptional opportunity to own a fully furnished, turnkey 3-bedroom, 2-bath condominium in one of Chicago's most dynamic and rapidly growing neighborhoods. Offering approximately 1,250 square feet of living space, this move-in-ready residence is ideally positioned for investors seeking immediate rental income or owner-occupants looking for a spacious home in a prime location. Thoughtfully furnished and ready for occupancy, the unit is well-suited for a variety of rental strategies, including mid-term housing, traveling professionals, visiting scholars, corporate housing, faculty rentals, and student housing. The spacious layout, modern conveniences, and desirable location create broad appeal for today's rental market. Located just minutes from the University of Chicago, the Obama Presidential Center, Jackson Park, the Museum of Science and Industry, Lake Michigan's lakefront, beaches, and bike trails, residents enjoy easy access to some of Chicago's most sought-after destinations. Convenient access to Lake Shore Drive, public transportation, shopping, dining, and neighborhood amenities further enhances the property's appeal. The surrounding area continues to benefit from significant public and private investment, including ongoing development related to the Obama Presidential Center and continued growth associated with the University of Chicago, making this an attractive opportunity for both immediate cash flow potential and long-term appreciation. Whether you're expanding your investment portfolio, seeking a furnished rental property, or searching for a spacious city residence in a thriving community, this turnkey Hyde Park/Woodlawn condo is an opportunity not to be missed.

6435 S Kenwood Avenue Unit #3S, Chicago

1221 E Marquette Road, Chicago
$659,000
5 Beds ⋅ 4 Baths ⋅ 12673209 MLS ⋅ ACTIVE Status
Attainable, comfortable, healthy, and cool! Award-winning, Greenline Homes Two Flat in Southeast Woodlawn! Greenline Homes has made Woodlawn the destination for high-performance homes in Chicago. We're thrilled to offer a resale of a groundbreaking two-unit building that showcases cutting-edge construction and high-performance materials and design throughout. Unit 1 is a bright, modern garden unit with two bedrooms. Unit 2 is a spacious and modern 3-bedroom/2.5-bath duplex. Sustainable without compromise. Both units boast beautiful and durable quartz countertops, custom cabinetry, and energy-efficient appliances. Own your energy. The building includes a solar photovoltaic system on the roof, which produces much of the building's energy needs and reduces the building's carbon footprint with clean, free renewable energy. Efficiency by design. Engineer-designed and sized zoned Mitsubishi heating and cooling provide extreme comfort and efficiency to both units. Comfort is built right in. Incredible engineered insulation, triple-pane glass, and an air-sealed building envelope make this building quieter and more comfortable than any standard building on the market. Healthy air is standard. Energy return ventilators and Panasonic whisper-quiet exhaust fans ensure consistent, high-quality indoor air while maintaining peak efficiency. The low-maintenance lifestyle. Well-designed exteriors with high-quality materials like James Hardie siding and commercial-grade roofing reduce maintenance, allowing your home to work harder for you, instead of you working hard for it. Greenline Homes is making sustainable, green homes more accessible, and now you can own a sustainable green home with income! Plus, a 2-car garage is included. The home is currently leased, and access for showing is limited. Located steps to Metra Electric Trains, Jackson Park, and the Obama Presidential Center.

1221 E Marquette Road, Chicago

6401 S Vernon Avenue, Chicago
$109,900
12669116 MLS ⋅ ACTIVE Status
Exceptional development opportunity in the rapidly growing Woodlawn neighborhood. This offering includes two buildable lots with separate PIN numbers, providing the potential to construct up to six residential units-three units per lot under current RT-4 zoning regulations (1,000 SF of land area required per allowable unit). Surrounded by numerous newly constructed homes and ongoing development, this property is ideally positioned for investors, developers, or builders seeking strong growth potential. Conveniently located just few blocks south of the University of Chicago, less than 1.5 miles from Jackson Park, Lake Michigan, the Obama Presidential Center site, Hyde Park, museums, shopping, dining, and public transportation. Take advantage of this rare opportunity to develop in one of Chicago's most sought-after and transforming neighborhoods.

6401 S Vernon Avenue, Chicago

6418 S Champlain Avenue, Chicago
$779,000
9 Beds ⋅ 6 Baths ⋅ 12650101 MLS ⋅ ACTIVE Status
Stunning 2022 construction three-flat in the heart of West Woodlawn - one of Chicago's most exciting South Side neighborhoods experiencing rapid growth and new development. Built on all sides with durable Hardie board fiber cement siding for enhanced curb appeal and long-term exterior protection. Each of the three units features 3 beds/2 baths with a true master suite layout, walk-in shower, custom closets, and generously sized bedrooms. Laminate flooring throughout. Kitchens feature 42-inch shaker cabinetry, Calacatta quartz countertops, 36-inch undermount stainless steel sink, and full stainless steel appliance package including refrigerator, dishwasher, stove & microwave. Spa-inspired bathrooms with sleek vanities and glass-enclosed showers. In-unit washer/dryer in every unit. Top-floor unit boasts soaring volume ceilings in the living room and master bedroom. Building features 600-amp electrical service, high-efficiency 50-gallon water heater, sump pump, and ejector pump. Three-car parking pad in rear. Located on a block surrounded by multiple new construction projects. Ideal for owner-occupant or investor. A must see!

6418 S Champlain Avenue, Chicago

6451 S Vernon Avenue, Chicago
$250,000
4 Beds ⋅ 2 Baths ⋅ 12646322 MLS ⋅ ACTIVE Status
Beautifully-maintained 2-story brick building located in a rapidly-developing area of Chicago, conveniently situated near I-94 and just west of the future Obama Presidential Center. This well-kept investment property features two spacious 2-bedroom units, each offering generous living and dining areas with functional layouts. Both kitchens are in good condition and include newer stoves and refrigerators replaced within the past year. The property also offers rear patios and a detached 2-car garage. The building is currently occupied by long-term tenants who have resided in the property for over 4 years, consistently pay rent on time, and take pride in maintaining their units. A solid investment opportunity in an area experiencing continued growth and redevelopment.

6451 S Vernon Avenue, Chicago

6636 S Marquette Drive, Chicago
$447,000
4 Beds ⋅ 3 Baths ⋅ 12599892 MLS ⋅ ACTIVE Status
5k CLOSING CREDIT AVAILABLE. Recently remodeled 2-unit building with a finished basement and two car garage. Sits on a 1.5 sized lot. Ideally located just two blocks from the new Robert R. McCormick Leadership & Economic Opportunity Center. Both units feature 2 bedrooms, updated kitchens , and bathrooms (2024), along with new windows (2024). Finished basement provides ample storage space and an additional full bath. Property improvements include an aluminum-coated roof (serviced in 2025), solar-powered security cameras (2024), and a well-maintained two-car garage with new plywood, newer siding, and a newer roof (2024). New Water heater (2025) and newer boiler (2024) Coin-operated laundry is located in the basement and will remain with the property. Current tenant is on month-to-month leases.

6636 S Marquette Drive, Chicago

6325 S Langley Avenue, Chicago
$799,000
9 Beds ⋅ 6 Baths ⋅ 12578786 MLS ⋅ ACTIVE Status
Located in the heart of Woodlawn, this newly constructed three-unit building presents a rare generational investment opportunity. Built in 2025, the property offers approximately 3,300 square feet of thoughtfully designed living space, featuring a total of nine bedrooms and six bathrooms. Each unit showcases contemporary finishes, including gleaming hardwood floors, stainless steel appliances, and highly efficient tankless water heating systems. Designed with luxury condo-level quality, the open-concept floor plans create bright, versatile living areas that seamlessly connect kitchens and living spaces-ideal for both everyday living and entertaining. All primary bedrooms include private en-suite bathrooms, enhancing comfort and privacy for residents. Units 1 & 3 are already rented for you. Strategically positioned near public transportation and major anchors such as the University of Chicago, the forthcoming Obama Presidential Center, and Jackson Park Golf Course, this property offers exceptional urban accessibility paired with neighborhood vibrancy. Residents also enjoy close proximity to Hyde Park, known for its celebrated dining scene, cultural attractions, and seasonal festivals. Looking ahead, the community is poised to benefit from an innovative geothermal energy initiative expected to deliver sustainable, energy-efficient power while significantly reducing long-term utility costs. This is a turnkey investment in one of Chicago's most rapidly evolving and opportunity-rich neighborhoods.

6325 S Langley Avenue, Chicago

6535 S King Drive, Chicago
$3,100,000
12571609 MLS ⋅ ACTIVE Status
Best Motel by OYO Chicago, 53-rooms, 2-Story California-style exterior corridor motel built in 1971, totaling approximately 20,200 building Sq ft. and about 18,000 Sq ft. of land with main-level on-site parking. Located in Chicago's Woodlawn neighborhood on the South Side, near Hyde Park and Englewood. The property is within 2-miles from Barak Obama Presidential Library, close to the University of Chicago, Jackson Park, the Museum of Science and Industry, neighborhood retails and transit, including the CTA King Drive Station. Approximately 1-mile east of the Dan Ryan Expressway and within several miles from and to downtown Chicago, the area is experiencing ongoing redevelopment, including the nearby Barack Obama Presidential Library (opening Spring 2026). Zoned C1-2 Commercial, permitting a wide range of uses including retail, auto services, warehouse, mixed-use, and residential above ground floor.

6535 S King Drive, Chicago

965 E 62Nd Street Unit #1, Chicago
$599,000
3 Beds ⋅ 3 Baths ⋅ 12367021 MLS ⋅ ACTIVE Status
Introducing Collection No.9 MOD - Where design, function, and lifestyle meet. Experience the best of city living in these four stunning duplex-up residences that blend modern design, thoughtful functionality, and exceptional quality. Each home spans two light-filled floors, offering spacious bedrooms, generous storage, and multiple outdoor spaces-including a private balcony and a show-stopping rooftop deck (per plan), fully equipped with water, gas, and electric hookups. The open-concept main level is designed for both style and comfort. At the heart is a chef-inspired kitchen featuring custom cabinetry, quartz counters with ample seating, and premium Samsung stainless-steel appliances. The seamless flow from the dining area to the expansive, extra-wide living room is perfect for entertaining, with a beautiful 20-foot-wide balcony just off the main living space. Up the stairs, the primary suite is a true retreat, roomy enough for a king-sized bed, with a spacious walk-in closet and a spa-quality bathroom that includes a curbless walk-in shower, a freestanding soaking tub, and a dual-bowl vanity. Two additional bedrooms, a second full bath, and a full laundry room with side-by-side washer/dryer, counterspace, and cabinetry complete the upper level. Set in the vibrant Woodlawn neighborhood, Collection No.9 offers unparalleled access to Washington Park, Jackson Park, the Midway Plaisance, and the University of Chicago's south campus, and CTA bus and train transportation. Enjoy proximity to the future Obama Presidential Center, the lakefront, harbor, beaches, and a growing array of local shops, cafes, restaurants, and a Jewel grocery store-all just minutes away via bike, car, or CTA. Don't miss your chance to own one of these exclusive homes. Schedule your private tour today and experience the space, style, and sophistication of Collection No.9 Mod.

965 E 62Nd Street Unit #1, Chicago

6209 S Dorchester Avenue Unit #1, Chicago
$225,000
3 Beds ⋅ 3 Baths ⋅ 12182193 MLS ⋅ ACTIVE Status
Winsome Woodlawn, 1,789 sq. ft., 3 BD/3 BA duplex down. Easy access to the University of Chicago, Jackson Park, 63rd St Beach, the Obama Presidential Center, and Lake Michigan. Entertain in the sun-filled living room with bay windows and crown molding overlooking Beehive Park and the 62nd & Dorchester Community Garden. There is an upgraded kitchen featuring solid surface countertops, ample kitchen cabinetry, a walk-in pantry, and stainless steel kitchen appliances. The primary bedroom features a walk-in closet and a spacious en-suite bathroom with a separate jetted tub and a full shower. No ongoing or upcoming special assessments. 0.2 miles from 63rd St Metra Station. 0.9 miles from CTA Cottage Grove Green Line Station. No rental cap - no short-term rentals - no Airbnb. HOA has a 30-day First Right of Refusal. Pets are allowed. No specific restrictions on weight or pet count. All pets must be vaccinated, supervised in common areas, and cleaned up after immediately. Samsung Electric Dryer (2017). Samsung Front Load Washer (2017). Whirlpool 4-Door French Door Refrigerator with External Refrigerated Drawer (2017). GE Dishwasher (2014). GE 4-Burner Gas Range (2014). Goodman A/C Condenser (2003). Heil Furnace (2024). Roof repairs & maintenance (2024). Reserves: $6,207.67 (as of August 31st, 2026). Chicago Public Schools: Carnegie Elementary School (PK-8) & Hyde Park Academy High School (9-12) - both are International Baccalaureate (IB) schools. Owner Occupancy: 13 out 21 units are currently rented. Tenant occupied for $1,925/monthly until 06/30/2027.

6209 S Dorchester Avenue Unit #1, Chicago



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