View All Kenwood Chicago IL Homes with Main Floor Primary Listings

$299,900
2 Beds 3 Baths 12723335 MLS ACTIVE Status
Welcome to this beautifully appointed 2-bedroom, 2.5-bath duplex that lives like a townhome, offering an exceptional combination of space, comfort, and modern convenience. Designed with both comfort and functionality in mind, this expansive home features hardwood flooring throughout the upper level, abundant natural light, and an open, inviting floor plan. The contemporary kitchen is appointed with granite countertops, rich cherry cabinetry, stainless steel appliances, and generous cabinet and prep space, making it ideal for everyday living and entertaining alike. The lower level has been enhanced with new flooring and new windows, adding both style and energy efficiency to the home's living space. The upper level offers two spacious bedroom suites, each with direct access to its own full bathroom. The primary suite features a private ensuite bath, while the second bedroom enjoys direct access to the hall bath, creating an ideal layout for guests, family, or a home office. A versatile loft-style flex space provides endless possibilities as a home office, reading nook, workout area, or creative space. Additional highlights include an in-unit washer and dryer, a convenient main-level powder room, a large private storage locker, an assigned parking space, and a private rear balcony-the perfect place to enjoy your morning coffee or unwind at the end of the day. Ideally situated on a quiet, tree-lined cul-de-sac, this home is just moments from neighborhood cafes, local dining, shopping, the lakefront, the University of Chicago, public transportation, Whole Foods, Trader Joe's, and the vibrant 53rd Street shopping corridor. With easy access to Lake Shore Drive, downtown Chicago is just minutes away. Whether you're looking for your first home, a place to entertain, or simply more room to live, this move-in-ready duplex offers the perfect blend of location, lifestyle, and value. Don't miss this exceptional opportunity!

4731 S Ingleside Avenue Unit #D1, Chicago

$910,000
4 Beds 5 Baths 12639055 MLS CLOSED Status
This stately all-brick 4-bedroom, 3.2 bath, two-story residence is ideally situated among historic mansions in prestigious Kenwood on iconic Professor's Row. Kenwood offers a rare suburban feel in the heart of the city and boasts an impressive roster of past and present residents, including Muddy Waters, Muhammad Ali, and the Obamas. Offering over 3,600 square feet of living space, this grand home presents a remarkable opportunity to bring your vision to life and restore it to its former glory. The main level welcomes you with a classical semicircular portico entrance leading into a grand foyer. A massive living room with fireplace flows into an adjacent parlor featuring floor-to-ceiling windows, creating an ideal setting for entertaining. The main floor also includes a sizable kitchen with large breakfast nook, formal dining room, and powder room. The second level features a generous primary bedroom with ensuite full bath and walk-in closet, two additional sizeable bedrooms, and a second full bath. A private landing leads to a second primary suite complete with its own ensuite full bath. The fully finished lower level provides additional living space with a cavernous rec room with bar area, second powder room, laundry area, and ample storage. An attached garage completes this exceptional offering. A rare opportunity to own a distinguished home in one of Chicago's most storied neighborhoods.

4959 S Greenwood Avenue, Chicago

$870,000
4 Beds 4 Baths 12618467 MLS CLOSED Status
6 of 13 units already sold! The Dorchester Collection is an exclusive, newly constructed gated townhome community in the prestigious Hyde Park/Kenwood neighborhood. This boutique development of just 13 residences is thoughtfully designed around a landscaped courtyard, communal garden, and welcoming front grounds. This expansive 4-bedroom, 3.5-bath townhome offers the perfect blend of modern luxury and historic character. The striking facade is a meticulous restoration of a 1904 church designed by nationally renowned architect Solo Spencer Beman, creating a truly one-of-a-kind architectural presence. The main level showcases an open-concept layout anchored by a chef's kitchen featuring custom two-tone cabinetry, quartz countertops with a full-height backsplash, and a premium Bosch appliance package-ideal for both everyday living and entertaining. The top-floor primary suite serves as a private retreat, complete with two walk-in closets and a spa-inspired en-suite bath featuring a white marble shower and separate soaking tub. The second level offers three generously sized bedrooms and two full bathrooms, providing flexible space for family, guests, or a home office. All bathrooms are finished with porcelain tile, custom cabinetry, quartz countertops, and Hansgrohe plumbing fixtures for a clean, modern aesthetic. Additional highlights include an attached, heated, above-grade oversized garage for one car, plus an exterior parking space. Ideally located in the vibrant University of Chicago community, this home is just 10 minutes from downtown and moments from shopping, dining, nightlife, and cafes along 53rd Street. Enjoy close proximity 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 #4, 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

$2,050,000
5 Beds 6 Baths 12541443 MLS CLOSED Status
A true rarity in historic Kenwood, this move-in-ready urban estate was meticulously restored during a multi-year renovation, reemerging as a masterful blend of early 20th-century elegance and modern luxury. Set on an expansive 50 x 300-foot lot within the historic district, the 1904 J.B. Cole residence was once praised by The Economist as "a picturesque structure in old English style of architecture"-a distinction it proudly maintains today. Regal stone lions still guard the original ornamental iron doors, opening to a dramatic foyer with a paneled fireplace and built-in seating. A sweeping circular staircase, illuminated by a period chandelier, sets an immediate tone of grandeur. The reimagined main level unites the home's two original parlors into elegant open-concept living and dining spaces, ideal for entertaining. Pocket doors lead to a chef's kitchen featuring stainless steel appliances, quartzite countertops, and generous banquette seating. French doors open to a sunroom and expansive deck overlooking the beautifully landscaped, fully fenced backyard. The second floor is anchored by a luxurious primary suite offering a huge custom walk-in closet, marble spa bath with steam shower, and a sun-filled, heated porch with serene backyard views. Two additional bedrooms, each with decorative fireplaces, share a thoughtfully updated bath. The third level provides two generously sized en-suite bedrooms with custom closets and steam showers. Wide-plank wood floors and custom windows are throughout, while the fully finished lower level lives like a home of its own. Heated with radiant flooring, it includes a spacious family/media room, large laundry room, fifth bedroom with walk-in closet, abundant storage, and a wine cellar tucked beneath the front porch. Completing the property is a Coach House with a four-car garage and a spacious flex space above-ideal for guests, office or gym. Ideally located near the University of Chicago, the Laboratory Schools, and Kenwood's dining, shopping, and cultural amenities, this is more than a home-it's a lifestyle. A rare opportunity to own a meticulously restored piece of Kenwood history, exquisitely reimagined for modern living.

4730 S Greenwood Avenue, Chicago

$1,089,500
5 Beds 3 Baths 12412880 MLS CLOSED Status
North Kenwood Living at Its Finest! This beautiful 5 bedroom, 2.1 bath home offers everything you're looking for, beginning with an exquisite front entry that opens into a refreshingly functional and elegant layout. The main level is ideal for both entertaining and everyday living, featuring a formal living room, a private parlor, a spacious dining room, and a gourmet chef's kitchen with a butler's pantry that leads to a gorgeous back deck and a serene, lushly landscaped private yard. A 2+ car garage completes the outdoor space. Upstairs, the second floor offers four generously sized bedrooms and a full bath. The top level is dedicated to a luxurious primary suite with space for a king-sized bed, a cozy sitting area, and a newly designed, lovely bath. The lower-level recreation room is perfect for games, movie nights, or gatherings, and includes multipurpose space ideal for a home gym, studio, or workshop. Set in one of Chicago's most architecturally rich and welcoming neighborhoods, this North Kenwood gem is moments from Lake Shore Drive, Lake Michigan's 43rd and 57th Street Beaches, the University of Chicago, the Griffin Museum of Science and Industry, and an excellent selection of grocery stores including Whole Foods, Trader Joe's, and Hyde Park Produce. You'll also enjoy easy access to Metra, CTA, and an array of dining and entertainment options. Don't miss the opportunity to call this timeless and spacious home your own. Schedule your private showing today.

4923 S Blackstone Avenue, Chicago

$2,085,000
5 Beds 4 Baths 12415335 MLS CLOSED Status
Luxury Living in the Kenwood Historic District - Award-Winning Design, Massive Yard! Nestled in the heart of the prestigious Kenwood Historic District, this luxurious residence is a true architectural gem, boasting a massive, beautifully landscaped yard that spans nearly half the length of a football field. Designed by award-winning architect, Anthony Akindele in 1999, this home blends timeless elegance with modern comfort, highlighted by a striking turret staircase, soaring ceilings, and walls of windows that bathe the interiors in natural light. Step inside to a formal foyer adorned with custom stonework that sets the tone for the craftsmanship throughout. The main level features an expansive living room with a wall of windows and a cozy double-sided fireplace that opens to the formal dining room-perfect for entertaining guests, holiday dinners, and family gatherings. A stylish powder room adds convenience, while the gourmet kitchen is a chef's dream with top-tier appliances, granite countertops, abundant cabinetry, double ovens, a cooktop with a vented hood, and an oversized refrigerator. The kitchen's serene view of the backyard makes it a tranquil space to cook, gather, and unwind. Ascend the gracefully curved turret staircase to the second floor, where you'll find three spacious bedrooms, two full bathrooms, and a utility room. The highlight of this level is the sprawling primary suite, featuring custom closets and a spa-like bathroom complete with granite floors and walls, a dual-sink vanity, an walk-in shower with body sprays, and an oversized luxurious elevated whirlpool tub-your personal sanctuary. The grand lower level offers high ceilings and a large family room with a fireplace and wet bar, two additional bedrooms, a full bathroom, and an impressive laundry room with tons of storage space. Whether you're hosting game nights or housing extended guests, there's room for everyone. The lower level does have an exterior door. But the crown jewel is the yard-truly breathtaking. From the elevated deck to the custom stone patio and the expansive grassy field lined with privacy trees, lush plants, and vibrant flowers, this outdoor oasis is ideal for everything from backyard parties to family sports tournaments. It's rare to find this kind of outdoor space in such a coveted urban setting. Additional features include a 3-car garage and a prime location within walking distance of Hyde Park's shops and restaurants, the lakefront, and the University of Chicago. Meticulously maintained and in pristine condition, this home is a one-of-a-kind masterpiece in one of Chicago's most storied neighborhoods. Welcome home!

925 E 49Th Street, Chicago

$1,125,000
4 Beds 4 Baths 12390654 MLS CLOSED Status
Welcome to this spectacular and fully renovated luxury residence nestled among the historic mansions of Kenwood, located on the picturesque and iconic Drexel Boulevard. One of the few completely upgraded homes in the neighborhood, this stately property blends timeless architecture with modern elegance, offering over 4,200 square feet of refined living space. Renovated just five years ago, the home features FIVE spacious bedrooms, three and a half bathrooms, a full finished basement, and an oversized three-car garage-all behind a secure gated entrance. The main floor offers a perfect layout for both formal entertaining and comfortable everyday living, featuring a sophisticated sitting room with a fireplace and a formal dining area that easily accommodates a table for eight. The stunning gourmet kitchen is equipped with top-of-the-line Monogram appliances, quartz countertops, under cabinet lighting, a custom butler's pantry, striking custom wood ceiling beams and an adjacent family room with a fireplace. The second floor houses four full bedrooms and a full sized laundry room on one floor! Featuring the huge primary suite with a walk-out balcony, customized walk-in closet, and a gorgeous bathroom that looks like it is in a 5 star hotel! Both bathrooms on the second floor have heated floors. The fully finished basement with high ceilings offers even more space to enjoy, including a full bathroom, wet bar, and large recreation room and a fifth bedroom, ideal for guests, a home gym, or a private office. Additional highlights include custom window treatments through-out, a spacious fenced backyard, a dual-zoned HVAC system, modern designer light fixtures, RING alarm system and an advanced camera surveillance system for added peace of mind. A rare luxury in the city, this home offers a 3-car garage with ample space for vehicles and storage. All of this within walking distance to the lake front, the shops/restaurants in Hyde Park, and the University of Chicago. Combining luxury, comfort, and historic charm in one of Chicago's most coveted neighborhoods, this home is truly a rare find. It's more than a home-it's a legacy. Welcome to Drexel Boulevard.

4741 S Drexel Boulevard, Chicago

$1,750,000
5 Beds 4 Baths 12296067 MLS CLOSED Status
This beautifully renovated Classical Revival residence is set on spacious grounds in the historic Kenwood neighborhood. In the late nineteenth century architect Solon Beman enjoyed significant success in Chicago and was widely regarded for his residential designs. His work was heavily influenced by the remarkable display of the classical architecture at the 1893 World's Columbian Exposition, reflected in this magnificent residence set well back from 49th Street. This iconic home, dominated by imposing columns and a striking two-story pedimented entrance, was the home of the famed architect. The house itself is an early structure of Kenwood and predates the neoclassical porch that is attributed to Beman. The current owners undertook an extensive renovation of the main structure and addition. While the screened porch still offers genteel views of the landmark neighborhood, the interior of the home is designed for modern living. The light-filled chef's kitchen overlooks the back yard, is adjacent to the formal dining room and has easy access to a deck to enjoy on warm summer days. Also on this level is the bright and spacious living room centered on a wood burning fireplace and accented by a charming reading nook. French doors lead to the screened porch, perfect for relaxing and enjoying views of the front yard. The Primary Bedroom has been thoughtfully enlarged and offers a luxurious new bath and custom storage. Down a new staircase are three bedrooms, centered on a family/play space with access to a private, enclosed yard. Also on this level are an additional bedroom and full bath. Refinished floors, new lighting, reconfigured stairway, new baths, mud room and breakfast area - see the full list of improvements provided. A beautiful blend of history and modernity - and in move-in condition. Welcome home!

1030 E 49Th Street, Chicago

$3,645,000
6 Beds 7 Baths 12216908 MLS CLOSED Status
This magnificent residence is located on a verdant tree-lined street in the heart of the Kenwood Historic District. While constructed after the turn of the last century, the house has been elegantly and thoroughly updated for life in the current one. Horatio R. Wilson was a well-respected architect of his time, and his work is known for structural integrity and quality of materials - each of which are apparent decades after he first conceived of the design. Sited on a ridge that once ran across the Kenwood landscape, the impressive house had been meticulously maintained by former owners, and that stewardship continues. Behind the handsome facade of the nearly 8,000 square foot house is a wide array of aesthetic and mechanical improvements recently completed. The latest renovation (following an earlier gut rehab) included extensive masonry work, new windows, floors sanded and refinished, fireplaces relined and chimneys tuckpointed, new lighting, new bathrooms; all combine to make this a home that is a rarity in the neighborhood - truly move in ready. The quality of the residence is apparent the moment one enters the foyer, with an elegant carved stairway that rises the full three levels, capped by a dramatic skylight. The refined layout of the main level offers a formal living and dining rooms, a library (each with a fireplace) and a kitchen that was transformed by John Vinci, a living legend of Chicago architecture. The stunning space offers Bulthaup cabinetry, with vistas that extend to the lush exterior through a glass wall to covered porch framed by commercial grade railings and staircase, accented by recessed lighting in the warmth of a wood slat ceiling. The second and third levels of the house each feature three bedrooms and multiple baths, of which the Primary Bath is truly a room with a view. Large welcoming landings, hardwood floors, walk-in closets, vintage woodwork, crown moldings, leaded glass - the amenities are too numerous to list! And they continue on the lower level, with a mud room complete with dog spa, exercise room, additional full laundry, game room, family room and storage. The coach house was fully renovated and accommodates two cars (with EV charger) below the contemporary one-bedroom apartment. Kenwood is a short 8-minute drive from the Loop, near the University of Chicago, Laboratory Schools and all the Hyde Park community has to offer. A stunning property where you can with the next chapter of its extraordinary history.

4943 S Woodlawn Avenue, Chicago

$1,600,000
9 Beds 6 Baths 12100303 MLS CLOSED Status
Welcome to a rare gem on one of historic Kenwood's most desirable tree-lined streets. The Alonzo Fuller House and Coach House, built in 1890, offer approximately 9,550 sq. ft., 8250 sq. ft. in the main house, and 1,300 sq. ft. in the coach house, all situated on a generous half-acre lot. This extraordinary property features three stories, an unfinished basement, and a four-car garage with a coach house. Step inside to discover a wealth of historic charm and character, including oak and parquet flooring, original trim and millwork, arched windows, turret rooms, coiffured ceilings, and magnificent original fireplaces. Designed by architect Federick W. Perkins, this expansive Queen Anne-style home welcomes you with a grand foyer and an exquisite staircase adorned with oak spindles and banisters. Entertain in style with a parlor, formal living room, and dining room featuring a bay window and a butler's pantry. The light-filled kitchen, with original maple floors and large windows, offers serene views of the picturesque backyard and coach house. The second floor features five spacious bedrooms with generous closets and two full bathrooms. The third floor offers the primary bedroom with an ensuite bath and walk-in closet, a versatile study/family room/ballroom with a fireplace, two additional bedrooms, a full bathroom, and the remnants of a convenient kitchenette, ideal for formal entertaining or everyday enjoyment.The unfinished basement presents endless possibilities, whether you envision a wine cellar with a tasting room, a hidden speakeasy, recreation room, full in-home gym, or game room. Outside, the property boasts a striking exterior of limestone and red brick, a driveway, a slate roof, and a heated four-car garage with storage, a workroom, and a coach house. The coach house includes two bedrooms, a bath, living and dining areas, and a sitting room, perfect for accommodating guests or multi-generational living. Experience Kenwood living in this exceptional residence. This magnificent home awaits your vision to carry it through the next several decades.

4832 S Ellis Avenue, Chicago

$999,999
4 Beds 4 Baths 11921646 MLS CLOSED Status
The Dorchester Collection is a newly-constructed elegant gated townhome development located in the prestigious Hyde Park/Kenwood neighborhood. A courtyard, a communal garden, and a landscape front yard support a total of 13 townhouses. This 5 bedroom, 3.5 bath townhome is a dream for anyone looking for something a little extra from their home. The one-of-the-kind 3-story luxury residence offers exceptional character and gorgeous architectural details with multiple components repurposed from the historic space. This stunning facade is restored, a 1904 church designed by nationally famed architect Solo Spencer Beman. The main level is an open-concept chef's kitchen featuring custom two-tone cabinetry, a quartz countertop/backsplash, and a Bosch appliance package. There is still an opportunity for the buyer to select finishes. The primary suite, located on the top floor, includes 2 walk-in closets and an en-suite bathroom highlighting a stunning white marble shower and a separate soaking tub. The second floor features 3 spacious bedrooms and two full bathrooms. All bathrooms feature porcelain tiles, custom cabinetry, quartz countertops, and Hans Grohe plumbing fixtures. The unit has an attached, heated, above-ground, oversized garage that fits 2 cars. This University of Chicago community is ideally located just 10 minutes from downtown and a short distance to grocery stores, nightlife, distinctive restaurants, and cafes on 53rd street. Access to the lake and museums, and immediately next to the tennis court, Kenwood Park, and Kenwood public library, make this townhouse development a must-see. *Photos may be of a similar unit*

4840 S Dorchester Avenue Unit #2, Chicago

$920,000
4 Beds 4 Baths 11808106 MLS CLOSED Status
The Dorchester Collection is a newly-constructed elegant gated townhome development located in the prestigious Hyde Park/Kenwood neighborhood. A courtyard, a communal garden, and a landscape front yard support a total of 13 townhouses. This 4 bedroom, 3.5 bath townhome is a dream for anyone looking for something a little extra from their home. The one-of-the-kind 3-story luxury residence offers exceptional character and gorgeous architectural details with multiple components repurposed from the historic space. This stunning facade is restored, a 1904 church designed by nationally famed architect Solo Spencer Beman. The main level is an open-concept chef's kitchen featuring custom two-tone cabinetry, a quartz countertop/backsplash, and a Bosch appliance package. There is still an opportunity for the buyer to select finishes. The primary suite, located on the top floor, includes 2 walk-in closets and an en-suite bathroom highlighting a stunning white marble shower and a separate soaking tub. The second floor features 3 spacious bedrooms and two full bathrooms. All bathrooms feature porcelain tiles, custom cabinetry, quartz countertops, and Hans Grohe plumbing fixtures. The unit has an attached, heated, above-ground, oversized garage that fits 2 cars. This University of Chicago community is ideally located just 10 minutes from downtown and a short distance to grocery stores, nightlife, distinctive restaurants, and cafes on 53rd street. Access to the lake and museums, and immediately next to the tennis court, Kenwood Park, and Kenwood public library, make this townhouse development a must-see.

4840 S Dorchester Avenue Unit #10, Chicago

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Kenwood, Chicago IL · Curated MLS Search

Homes with Main Floor Primary in Kenwood, Chicago IL

An editorially curated view of every active homes with main floor primary listing in Kenwood, Chicago IL. Updated in real time from the local MLS, presented without the noise.

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