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$999,000
3 Beds 4 Baths 12706221 MLS ACTIVE Status
Move-in ready new construction at The Kenwood Reserve, an exclusive collection of just three boutique luxury residences nestled on a quiet, tree-lined cul-de-sac in historic Kenwood. Thoughtfully designed as a full masonry build, each three-level residence delivers the scale and privacy of a single-family home with the ease of modern new construction, offering expansive living spaces, refined designer finishes, private outdoor living, and a 2-car garage. Sun-filled interiors are complemented by clean architectural lines and timeless finishes throughout. The beautifully appointed kitchen is designed for both everyday living and effortless entertaining, featuring custom dark wood Studio 41 cabinetry, an oversized quartz island, and a spacious pantry offering exceptional storage. Limited opportunity remains for buyer customization and select finish selections. The open-concept main living spaces flow seamlessly into a rare private outdoor retreat, ideal for entertaining, relaxing, and indoor-outdoor living rarely found in the neighborhood. With no monthly HOA assessment, The Kenwood Reserve delivers a rare combination of privacy, autonomy, and boutique luxury living. The lower level offers a warm and versatile secondary living space perfect for a media room, lounge, playroom, or fitness area, alongside a private fourth bedroom ideal for guests or a home office. A unique additional 230 SF unfinished space presents endless possibilities for customization, including a wine cellar, creative studio, wellness room, or additional storage. Dual HVAC systems with two furnaces and two central air-conditioning units for efficient, zoned comfort throughout.Located moments from Hyde Park, the University of Chicago, lakefront parks, dining, and cultural institutions, The Kenwood Reserve offers a rare opportunity to own full masonry new construction with private outdoor space, garage parking, and boutique luxury living in one of Chicago's most historic neighborhoods.

4721 S Ingleside Avenue, Chicago

$75,000
3 Beds 2 Baths 12705188 MLS ACTIVE Status
Beautifully maintained and thoughtfully designed, this spacious three-bedroom residence offers an ideal blend of comfort, style, and functionality. Expansive wall-to-wall windows flood the home with natural light while showcasing stunning city and treetop views. The open floor plan is anchored by a contemporary fireplace with custom built-in shelving, while a separate dining area provides the perfect setting for everyday living and entertaining. The kitchen features stainless steel appliances, marble countertops with beveled edges, abundant cabinetry, a large island, and generous storage space. Rigid-core flooring extends throughout the home, creating a seamless and sophisticated aesthetic. The spacious bedrooms offer exceptional closet space, beautiful views, and the flexibility to accommodate a dedicated home office, guest room, or creative workspace, including thoughtfully designed built-in organization with storage for more than 80 pairs of shoes. Harper Square amenities include door staff, on-site management, a hospitality room, fitness center, laundry facilities, commissary services, and available garage parking for a nominal monthly fee. Ideally situated in the heart of Hyde Park and Kenwood, this exceptional location offers convenient access to the lakefront, shopping, dining, museums, public transportation, and major expressways. Cash purchase only. Board approval required. Proof of funds required before showings.

4850 S Lake Park Avenue Unit #1201, Chicago

$185,000
1 Beds 1 Baths 12703440 MLS ACTIVE Status
Investor Special!!! Turnkey income-producing opportunity in the highly sought-after historic Drexel Boulevard corridor. This spacious 1-bedroom, 1-bath condominium offers wood-finish flooring throughout, a cozy fireplace, a large bathroom with dual vanities, and an efficient layout that appeals to long-term tenants. The well-maintained building features secure fob entry, an assigned exterior parking space, and low HOA dues. The unit is currently leased to an excellent long-term tenant paying $1,750 per month through March 1, 2027, providing immediate, stable cash flow from day one with no vacancy concerns. Seller is also offering a $2,500 appliance credit, allowing the new owner or future occupant to update the appliances to their personal preference while adding value to the property. A professionally managed, investor-friendly building that allows rentals, making this a rare opportunity to acquire a turnkey asset with immediate income and future upside.

4537 S Drexel Boulevard Unit #203, Chicago

$505,000
4 Beds 3 Baths 12703019 MLS ACTIVE Status
Set along the iconic boulevard of historic Kenwood, this expansive and character-filled residence at 5036 S. Drexel Blvd. #3N blends timeless architectural detail with thoughtful modern updates. Located in a distinguished 1910 building designed by renowned architect Frank B. Jobson, this beautifully preserved home offers exceptional scale, rich craftsmanship, and a layout that lives comfortably for both everyday living and entertaining. With ~2,600 square feet, this space truly lives like a single family home. Inside, original details take center stage: from quarter-sawn oak wall paneling and pocket doors to coffered ceilings, leaded glass built-ins, Honduras mahogany paneling, original sconces and French doors. Hardwood flooring runs throughout featuring maple in the kitchen and oak throughout the remaining living spaces, while original wood doors and hardware further preserve the home's historic charm. The spacious living and dining areas offer elegant entertaining space filled with warmth and character. The dining room showcases stunning original built-ins, quarter-sawn oak detailing, coffered ceilings and lush park views, while the living and family rooms feature striking Honduran mahogany paneling, stunning gas fireplaces with original mantels and tile work. Completed in 2026, the updated kitchen combines functionality and design with granite countertops, full wall marble tile backsplash, Bosch appliances, LG dishwasher, outside venting Bosch hood, abundant cabinetry, and a custom movable island with extensive storage. The charming butler's pantry provides additional storage and workspace and a separate lovely beverage center are an extension to your kitchen. The home offers four spacious bedrooms, including a newly updated fourth bedroom and half bath completed in 2026. The hallway bathroom was renovated in 2021 with marble finishes, Kohler and Grohe fixtures, custom vanity inserts and a custom medicine cabinet. This unit provides two private outdoor spaces: an enchanting front balcony off of the family room, accented with stone arches and overlooking the boulevard and the rear deck off of the kitchen complete with original glass French doors. Additional highlights include generous closet space, in-unit laundry, replacement windows throughout most of the home, beautifully restored radiators and new energy-efficient, quiet window AC units. The building has a parking lot with five spaces which are available on a first arrival basis. Street parking is very accommodating, as Drexel Boulevard is not designated as either a snow or bus route. Residents enjoy close proximity to the University of Chicago, University of Chicago Medicine, the new Northwestern outpatient facility, Hyde Park stores and restaurants, lakefront access, and multiple transportation options nearby.

5036 S Drexel Boulevard Unit #3N, Chicago

$149,900
1 Beds 1 Baths 12701256 MLS ACTIVE Status
Updated one bedroom condo in an investor-friendly building across the street from the green oasis of Kenwood Community Park. This top floor condo features hardwood floors, combined living/dining space, spacious bedroom, and updated kitchen with stainless steel appliances and granite counters. The low monthly assessment of $301 includes heat and cooking gas. Access to the CTA #6 bus, University of Chicago UGo shuttle and #172 bus, and Metra Electric train station is within a short walking distance. Dog-friendly Kenwood Community Park, spanning 7 expansive acres, features tennis courts, baseball fields and athletic field for soccer or football. There is a wait list for onsite parking and ample street parking along Dorchester Ave.

4939 S Dorchester Avenue Unit #5F, Chicago

$650,000
5 Beds 4 Baths 12685639 MLS ACTIVE Status
Value & Location: "Stunning Duplex with Dedicated Property Easement next to Kennicott Park!" Discover an incredible investment or house-hacking opportunity in Chicago's Historic Kenwood neighborhood. Priced to sell, this unique, townhouse-style two-unit building spans multi-level living space. Situated directly across from the scenic Kennicott Park and minutes from DuSable Lake Shore Drive, this property is perfectly configured for an owner-occupant looking to live comfortably while collecting premium rent, or for an investor seeking a high-demand multi-family asset. Additionally, the parcel features a legal property easement, providing guaranteed side yard buffer, private access, and flexibly usable outdoor space adding long-term functional value to the house. The Owner's Suite A massive, sun-drenched multi-level layout designed for comfortable everyday living. Main Level Entertaining: Open-concept living and dining areas feature high ceilings. Upper-Level Bedrooms: Two spacious, private bedrooms are tucked away upstairs, one bedroom on the ground level, including with its own bathroom in brand new rehabbed part. Garden level: living room, laundry room, utility room, bathroom, bedroom and office, with separate egress through public room from garden level. Park Views: Enjoy beautiful tree-lined views in directly north to local green park space, and rapid access to close-by Burnham Park via 43rd street bridge over LSD, just steps away. The Income Suite Smart Multi-Level Layout: Perfectly proportioned and maximizing space, making it highly attractive to premium renters. Flexible 1.5-Bedroom Design. Features a spacious primary bedroom with mantle piece plus a versatile half-bedroom, ideal for a home office, nursery, or creative studio. Hallway closet. Turnkey Rental: Equipped with a funcitonal kitchen, bright living area, and independent private entry to ensure total resident privacy. Unbeatable Kenwood Location: Next to Kennicott Park: Step right outside to enjoy the Kennicott Park Fieldhouse, community programs, fitness facilities, sports fields. Commuter's Dream: Enjoy rapid access to Downtown Chicago via DuSable Lake Shore Drive 39th or 47th street ramps, or use nearby 43rd street Dan Ryan expressway ramp. Public Transit Friendly: Located steps from convenient CTA bus routes and Metra Electric District 47th street station ensures a seamless daily commute. Building & Exterior Features Property Easement: Benefit from a built-in property easement that ensures easy accessibility and use for outdoor activities. This easement is a source of natural light on the west side of the house. Separate metered electric utilities ensures stress-free management, shared radiator system and gas ensures efficiency. Townhouse Structure: Vertical layout ensures no neighbors are living above or below your primary living areas.

1132 E 44Th Street, Chicago

$399,500
4 Beds 2 Baths 12675404 MLS PRICE CHANGE Status
For the first time in 47 years, a rare value-add opportunity in the heart of the historic Kenwood Mansion District. This 4-bedroom, 1.1-bath townhome offers a functional three-level layout, including a partially finished basement, a private fenced yard, and access to a shared private community park-providing exceptional outdoor space in the city. Solid brick and concrete construction provides a strong foundation for renovation, with potential for owner-occupants looking to build equity. All four bedrooms are conveniently located on one level, however, some owners have reimagined the space and combined two bedrooms to make a large primary suite. Ideally located near Kenwood Community Park, Metra, Lake Michigan, Lake Shore Drive, Jackson Park, the University of Chicago, and the Obama Presidential Center. Surrounded by some of Chicago's most distinguished homes, this is a unique opportunity to renovate and create a home of your own in one of the Chicago's most sought-after neighborhoods.

4753 S Woodlawn Avenue, Chicago

$105,000
1 Baths 12664473 MLS ACTIVE Status Newport Condominiums BLDG.
Located on the high 23rd floor in the south tower of the sought-after Newport Towers complex, this quaint, charming studio unit provides great space with amazing views of the lakefront and should not be overlooked! The unit offers a generous living space with southern and eastern exposure, sunrise views will brighten the space and make the unit feel larger and brighter day in day out! The galley kitchen can be opened to really open the space up and there is ample closet space not often found in studio units! The building is a full amenity building, garage rental space is available, on-site management, pool, gym, this building has it all. Also add walk to Lake, walk to museums and so much more it is hard to beat this unit at this value! Get inside today to appreciate all this unit has to offer!

4800 S Chicago Beach Drive Unit #2308S, Chicago

$120,933
1 Beds 1 Baths 12519785 MLS ACTIVE Status
***I-N-V-E-S-T-O-R-S---S-P-E-C-I-A-L---A-L-E-R-T-!-!-!***R-E-N-T-E-R-S---S-P-E-C-I-A-L---A-L-E-R-T-!-!-!*** B-U-Y-E-R-S---S-P-E-C-I-A-L---A-L-E-R-T-!-!-!*** HYDE PARK/KENWOOD CONDO WITH A LAKE VIEW ***LET'S MAKE A DEAL!!! F-O-R---I-N-V-E-S-T-O-R-S---THAT IS BUILDING THEIR PORTFOLIO --- DON'T MISS YOUR OPPORTUNITY TO OWN THIS 1 BEDROOM 1 BATHROOM CONDO IN THE HEART OF CHICAGO, WITH BREATHTAKING VIEWS OF LAKE MICHIGAN... IF YOU ARE AN INVESTOR THAT IS BUILDING YOUR REAL ESTATE PORTFOLIO AND WANT TO RENT OUT A CONDO TO PAY THE MORTAGE, THIS DEAL IS FOR YOU!!! NEWPORT IS INVESTOR FRIENDLY WITH NO RENTAL CAP... YOU WOULD LOVE TO OWN THIS CONDO... ***RENTERS, IF YOU ARE TIRED OF PAYING YOUR LANDLORD MORTGAGE, IT IS TIME FOR YOU TO OWN AND PAY YOUR OWN MORTGAGE... YOU WOULD LOVE TO OWN THIS CONDO... IF YOU LOVE NATURAL LIGHT AND WATCHING THE BEAUTIFUL MORNING SUNRISES INCLUDING THE SOUTHERN VIEW OF LAKE MICHIGAN, YOU WILL LOVE TO OWN THIS SPACIOUS SOUTH TOWER ONE BEDROOM CONDOMINIUM ON THE 19TH FLOOR IN THE HISTORIC KENWOOD/HYDE PARK NEIGHBORHOOD...THIS UNIT HAS CARPET THROUGHOUT IN THE LIVING ROOM DINING ROOM, HALLWAYS AND BEDROOM, WITH FANTASTIC CLOSET SPACE... THE KITCHEN HAS A NEW FLOOR, NEW STOVE, STOVE TOP, REFRIGERATOR, AND DISHWASER. THERE IS HEATED INDOOR VALET PARKING - NOT INCLUDED IN THE PRICE, BUT PARKING IS AVAILABLE TO RENT AND PARKING SPACES ARE OCCASIONALY FOR SALE... THE NEWPORT CONDOMINIUM BUILDING PROVIDES 24-HOUR DOORMAN, ON-SITE MANAGMENT/ENGINEER, RECEIVING ROOM, FREE BASIC CABLE,FREE INTERNET, COMMON LAUNDRY ON THE LOWER LEVEL, ACCESS TO THE BIKE ROOM AND ASSIGNED STORAGE/IF APPLICABLE, A GO-GROCER GROCERY STORE, AS WELL AS A ROOF TOP VIEW ON THE 28TH FLOOR IN THIS BUILDING... THE NEWPORT HEALTH CLUB INCLUDES AN INDOOR POOL, JACUZZI, SAUNA, AND EXERCISE ROOM (FOR AN ADDITIONAL FEE FOR: SINCLE $16.67, FAMILY $25.00 PER MONTH)... ADDITIONALLY, YOU WILL ENJOY THE CONVENIENCE OF THE FREE SHUTTLE BUS SERVICE TO LOCAL TRANSPORTATION HUBS, NEIGHBORHOOD GROCERY STORES, AND SHOPPING AREAS. THIS SECURE, WELL MANAGED BUILDING ALSO HAS ON-SITE HEATED INDOOR VALET PARKING...L-O-C-A-T-I-O-N-!---L-O-C-A-T-I-O-N-!---L-O-C-A-T-I-O-N-!---LOCATED IN THE HISTORIC KENWOOD/HYDE PARK COMMUNITY... WALKING DISTANCE TO CHICAGO'S BEAUTIFUL LAKEFRONT TO ENJOY WALKING AND BIKING PATH, ETC., CLOSE TO SHOPPING ON 53RD STREET, CAFES, RESTAURANTS, NEIGHBORHOOD PARK, METRO STATION, MUSEUMS, THE UNIVERSITY OF CHICAGO, AND SELECTION OF GREAT SCHOOLS. ALSO CLOSE TO WHOLE FOODS, TRADER'S JOE'S TARGET AND MUCH MORE!... WITHIN 7-10 MINUTES TO DOWNTOWN HYDE PARK, 15-20 MINUTES TO DOWNTOWN CHICAGO, MINUTES AWAY FROM PUBLIC TRANSPORTATION: CTA #2, #6, #28, AND CTA #55 THAT RUNS 24 HOURS A DAY.... AND MINUTES TO THE SOUTH SHORE OUTER DRIVE EXPRESS WAY, AND 15 MINUTES AWAY FROM INTERSTATE 57 EXPRESSWAY. ***INVESTORS***RENTERS***BUYERS*** MAY RECOGNIZE THE OPPORTUNITY THIS BUILDING HAS TO OFFER! OPPORTUNITY IS KNOCKING. WILL YOU ANSWER? *** M-A-K-E---Y-O-U-R---A-P-P-O-I-N-T-M-E-N-T---T-O-D-A-Y-!-!-!---D-O-N-'-T---D-E-L-A-Y!!! THANK YOU FOR YOUR INTEREST!

4800 S Chicago Beach Drive Unit #1910S, Chicago

$40,000
2 Beds 1 Baths 12603738 MLS ACTIVE Status
Seller is highly motivated and seeking a serious buyer ready to move in soon for this well-maintained 15th-floor, 2-bedroom, 1-bathroom unit offering comfort, convenience, and elevated city living near downtown Chicago. Located in the heart of Hyde Park, this home features brand-new appliances, including a gas stove covered in the monthly fee, along with the added benefit of higher-floor privacy and views. Property Details *Monthly Carrying Charges: $1,340 *Shares / Refundable Deposit: $5,460 *Garage Parking: Starting at $75/month Monthly Fee Includes *Heat, water, and cable (HBO, Showtime, and STARZ included) *Gas and appliance coverage (including stove) *All unit maintenance *Common area amenities Additional Highlights *24/7 building and garage security *Only electricity is excluded from the monthly fee *Owner-occupancy required for at least one year before resale All renovations or changes require board approval This 15th-floor unit offers a rare combination of affordability, security, and modern updates, making it an ideal opportunity for a buyer ready to act quickly and move right in in one of Chicago's most desirable neighborhoods. CASH DEAL ONLY

4850 S Lake Park Avenue Unit #1507B, Chicago

$900,000
3 Beds 3 Baths 12618439 MLS ACTIVE Status
The Dorchester Collection is an exclusive, newly constructed gated townhome community nestled in the prestigious Hyde Park/Kenwood neighborhood. Comprising just 13 residences, the development is thoughtfully designed around a beautifully landscaped courtyard, communal garden, and lush front grounds. This exceptional 3-bedroom, 2.5-bath townhome offers a rare blend of modern luxury and historic charm. Spanning three levels, the residence showcases remarkable architectural character, with select elements thoughtfully repurposed from the original 1904 church designed by renowned architect Solo Spencer Beman. The restored facade provides a striking and timeless presence. The main level features an open-concept layout anchored by a chef's kitchen with sleek Zecchinon Italian cabinetry, Bosch appliances, and abundant concealed storage-perfect for both everyday living and entertaining. The primary suite is a true retreat, offering expansive walk-in closets and a spa-inspired en-suite bath complete with a white marble shower, separate soaking tub, and a Restoration Hardware vanity accented by brass and matte black Hansgrohe fixtures. Upstairs, two additional generously sized bedrooms provide flexible space for guests, family, or a home office. This home includes one exterior parking space along with an attached, heated, above-grade oversized garage accommodating one vehicle. Two private outdoor spaces offer additional room to relax and unwind. Ideally located in the vibrant University of Chicago community, this home is just 10 minutes from downtown and moments from the shops, dining, and nightlife along 53rd Street. Enjoy easy access to the lakefront, museums, Kenwood Park, tennis courts, and the Kenwood Public Library-making this exceptional residence a true standout.

4840 S Dorchester Avenue Unit #1, Chicago

$925,000
6 Beds 5 Baths 12605785 MLS ACTIVE Status
Looking for a Stunning 3-Flat Georgian Style Multi-Family Building or convert to your Single Family Home in the Hyde Park/Kenwood Community, where historical elegance is seamlessly integrated with contemporary living. This rare gem has been updated on the 1st level only to offer both classic charm and modern amenities perfect for short-term rentals generating great annual income. Bring your own touches for units 2. Step through the front portico (with 4 tall columns), and see how 3 units, (1,300 ft on each floor) exude cozy living space with historic charm flooded with natural light from brand new windows, featuring many vintage details including solid mahogany doors, molding throughout, as well as oak and antiqued pine flooring. The 1st floor duplex unit has 1700+sf living space with various new updates including stainless steel appliances, cortz countertops, refurbished original hardwood floors, new fixtures, freshly painted and a fully height semi-finished basement, and so much more. The 3rd floor features an updated kitchen with new cortz countertops, laminate flooring mixed with the original oak wood, and freshly painted. This property is zoned as RM5 w/two city lots (25 ft x 200 ft), offering the new owner an opportunity for growth, with a shared driveway connected to a gated luxury townhome community, a new construction project converted from the original building constructed by the architect, Solon Spencer Beman. Don't miss your chance to own a piece of history that caters to today's lifestyle needs, and steps from Chicago's Beautiful Lakefront and shuttle service to the University of Chicago. Please note, this building can be easily converted to a single family home if wanted.

4836 S Dorchester Avenue, Chicago



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