Search Kenwood Homes for Sale

Homes for Sale in Kenwood, Chicago

Kenwood, located on the South Side of Chicago, is a neighborhood with a rich history and architectural elegance. Known for its grand mansions, historic homes, and proximity to Lake Michigan, Kenwood offers a diverse range of real estate options for buyers seeking both vintage charm and modern amenities. The neighborhood has long been a favorite for those looking for a quieter, more residential feel while still being just minutes from downtown Chicago.

Real Estate Overview in Kenwood

Kenwood’s real estate market is known for its expansive single-family homes, many of which are historic mansions dating back to the early 20th century. These homes often feature unique architectural details such as large porches, elegant woodwork, and expansive gardens. For buyers seeking a more modern lifestyle, Kenwood also offers a variety of condos and townhomes, many of which are located in well-preserved vintage buildings or newly developed properties with contemporary features.

Additionally, Kenwood is home to several 2-4 flats, which provide excellent opportunities for buyers looking to invest in multi-unit properties. These buildings are ideal for those looking to generate rental income while living in one of Chicago’s most prestigious and historic neighborhoods.

Why Choose Kenwood?

Living in Kenwood means enjoying a perfect balance of history, culture, and convenience. The neighborhood is home to a number of landmarks, including the Robie House, designed by Frank Lloyd Wright, and President Barack Obama’s Chicago residence. Residents can also enjoy easy access to Lake Michigan’s lakefront parks and trails, offering plenty of opportunities for outdoor recreation. Kenwood’s proximity to Hyde Park means that residents can take advantage of the vibrant dining, shopping, and cultural scenes found in the neighboring community.

Kenwood is well-connected by public transportation, with the Metra Electric Line providing quick commutes to downtown Chicago. The neighborhood is also a short drive from major highways, making it easy for residents to access other parts of the city.

Explore Nearby Neighborhoods

Kenwood is surrounded by some of Chicago’s most vibrant communities. To the south lies Hyde Park, home to the University of Chicago and a lively cultural scene. To the west, Bronzeville offers a rich history and growing arts community. The South Loop, located to the north, provides a more modern urban living experience with high-rise condos and a wealth of dining and entertainment options.

Start Your Home Search in Kenwood

Whether you're searching for a grand historic single-family home, a modern condo, or an income-generating 2-4 flat, Kenwood offers a unique blend of history, architecture, and convenience. Explore the latest homes for sale in Kenwood Chicago and discover why this neighborhood is one of Chicago’s most desirable places to live.

Latest Kenwood Homes for Sale

$40,000
2 Beds ⋅ 1 Baths ⋅ 12741378 MLS ⋅ NEW Status
A well-maintained residence offering excellent value and strong long-term potential. Located on the 7th floor, this unit provides bright natural light and pleasant open views. The building features a fully renovated marble lobby, 24hour reception, and onsite security, creating a secure and welcoming environment for residents and guests. The home includes 2 bedrooms, 1 bathroom, and a functional combined living/dining/kitchen layout that offers flexibility for updates or customization. Ideal for buyers seeking an affordable entry into the Hyde Park/Kenwood market or investors looking for a value-add opportunity. Close to the lakefront, parks, public transit, and neighborhood amenities. Cash only!

4850 S Lake Park Avenue Unit #709, Chicago
$2,729,000
12755416 MLS ⋅ NEW Status
1209 E. Madison Park and 1210 E. Hyde Park Blvd. are two back-to-back 4-unit buildings with 8 units, 37 bedrooms, and 19 bathrooms on the border of Hyde Park and Kenwood. Unit sizes are exceptional for the submarket: four and five-bedroom layouts averaging 1,800 square feet with in-unit laundry, renovated kitchens and baths, and original vintage detail throughout. The property is fully occupied, with every lease running through late 2026 and 2027. Five units are supported by Housing Choice Voucher contracts, pairing a government-backed rent component with a deep private renter pool. At $317,064 in annual scheduled rent, the offering combines immediate cash flow with clear near-term upside as a utility reimbursement program already in place on recent leases rolls out building-wide, one remaining original unit awaits renovation, and below-market units convert to market rent on turnover. This property is ideally suited for investors seeking a core Kenwood / Hyde Park position with strong in-place income and durable long-term value growth. The location drives consistently high demand, making this an outstanding opportunity in one of the most resilient and historically stable multifamily submarkets in Chicago.

1209 E Madison Park Boulevard, Chicago
$229,999
2 Beds ⋅ 2 Baths ⋅ 12755276 MLS ⋅ NEW Status
BEAUTIFUL TOP-FLOOR 2-BEDROOM, 2-BATH CONDO IN KENWOOD! This bright and spacious home features a desirable open-concept living and dining area with soaring ceilings and rich cherry hardwood floors throughout. The primary suite offers a private bath and a generous walk-in closet, creating the perfect retreat. The updated kitchen is equipped with stainless steel appliances, ample cabinetry, and an in-unit washer and dryer for added convenience. Low HOA assessments make this home an exceptional value. Ideally located in the heart of Kenwood, you'll enjoy easy access to the University of Chicago, shopping, restaurants, public transportation, Lake Shore Drive, and the expressway. Just minutes from downtown Chicago, this home offers the perfect combination of comfort, convenience, and location. Don't miss the opportunity to make this exceptional condo your new home!

4731 S Ingleside Avenue Unit #A3, Chicago
$2,175,000
8 Beds ⋅ 5 Baths ⋅ 12752094 MLS ⋅ NEW Status
Situated on one of the most desirable blocks in the heart of the Kenwood Historic District, this remarkable residence is distinguished by its striking crow-stepped gable and extraordinary architectural detail. Built in 1896, at the height of Chicago's fascination with revival architecture, the home was designed by noted architect William Otis, a graduate of Paris's prestigious Ecole des Beaux-Arts. His design captures the elegance and craftsmanship of 17th-century Dutch architecture, adding to the neighborhood's character. Exceptionally preserved, the house offers a rare combination of architectural authenticity, gracious scale, and thoughtful modern updates. Beyond its richly detailed brick facade, the interior unfolds with abundant natural light and an extraordinary collection of original craftsmanship, including finely carved woodwork, art glass, and decorative tile. Expansive formal living and dining rooms provide an elegant setting for entertaining, while the warm, inviting kitchen flows naturally into a sun-filled family room and out to a spacious deck - creating an effortless connection between formal and everyday living. With eight bedrooms, multiple fireplaces, and a dramatic third-floor family room featuring soaring 15-foot ceilings, the home offers remarkable scale and versatility. Every floor reveals another layer of the house's architectural character and thoughtful design. The beautifully landscaped, tree-lined lot is further enhanced by a charming coach house with a two-bedroom apartment, offering exceptional flexibility for guests, extended family, a private office, or supplemental income. Timeless in character and sophisticated in its proportions, this extraordinary residence represents a rare opportunity to become the steward of one of Kenwood's treasured pieces of architectural heritage-a home where history, craftsmanship, and modern living come together with grace.

4923 S Greenwood Avenue, Chicago
$445,000
4 Beds ⋅ 2 Baths ⋅ 12754001 MLS ⋅ NEW Status
Beautifully updated 4-bedroom home in the heart of Hyde Park featuring timeless hardwood floors, soaring ceilings, and an impressive vaulted foyer upon entry. The home has a dramatic 36 ft gallery hallway creating an elegant flow to spacious bedrooms. Sun-filled south-facing exposure pours natural light throughout the home, charming sunrooms at both the front and rear of the property offering the perfect spaces to relax, work, or entertain. Thoughtfully updated while maintaining character and warmth, this home combines classic architecture details and modern comfort in one of Hyde Park's most desirable areas. Enjoy easy access to local coffee shops, restaurants, whole foods, and neighborhood favorites along 53rd Street. Convenient transportation options include Metra, CTA, and easy access to Lake Shore Drive. Garage Parking and large storage space included. This home will not disappoint!

1140 E Hyde Park Boulevard Unit #3D, Chicago
$1,775,000
6 Beds ⋅ 5 Baths ⋅ 12753755 MLS ⋅ NEW Status

4801 S Kimbark Avenue, Chicago
$40,000
2 Beds ⋅ 1 Baths ⋅ 12747823 MLS ⋅ ACTIVE Status
Welcome home to an abundance of natural light in this renovated south-facing 2 bed, 1 bath co-op, offering approximately 1,000 square feet of comfortable living space with sunny south-facing views that take in the lake from this upper-floor vantage point. This unit has been thoughtfully updated with a new kitchen, new flooring throughout, and a new vanity in the bathroom. Located just minutes from everything that sought-after Hyde Park has to offer, including easy access to the University of Chicago, Metra, lakefront trail, Museum of Science and Industry, shopping, and award-winning restaurants. Assessments at this fully owner-occupied co-op include heat, AC, water, cable, real estate taxes, 24-hour door staff, party room, laundry room, fitness center, and interior and exterior maintenance. Covered parking is available for $80 per month. Please note that in addition to the purchase price, $4,640 in transfer shares are required to be deposited with Harper Square Cooperative prior to move in. This transaction is cash only, and rentals are not permitted.

4850 S Lake Park Avenue Unit #2109B, Chicago
$399,900
3 Beds ⋅ 2 Baths ⋅ 12685740 MLS ⋅ ACTIVE Status
Nestled in the heart of the historic South Kenwood Landmark District, this beautifully maintained 3-bedroom, 2-bath home offers the perfect blend of timeless neighborhood charm and modern comfort. Overlooking the green spaces of Madison Park, this second floor home enjoys peaceful treetop views. 5041 S Dorchester is a boutique building of just five residences. The property was completely renovated and modernized in 2001, including all new building systems. Inside, you'll find a thoughtfully designed open-concept layout featuring hardwood floors throughout, a contemporary kitchen with stainless steel appliances, granite countertops, and the perfect amount of space for both everyday living and entertaining. The spacious floor plan includes three generous bedrooms, two outdoor spaces, elegant marble tile baths, and the convenience of in-unit laundry along with central heat & air conditioning. The primary bedroom leads to its own private balcony for relaxing or morning coffee. The primary bath has dual entry access to the primary and second bedrooms. The third bedroom opens to a second outdoor space and leads down to the parking area. Rare for the neighborhood, the home includes two deeded parking spaces (one of the spaces is covered) in a secure gated lot. Enjoy an unparalleled Hyde Park lifestyle just steps from Whole Foods, Madison Park, neighborhood dining and shopping, the lakefront, and the vibrant cultural and academic amenities of the University of Chicago. Nearby Metra and CTA transportation provide quick access to downtown Chicago. A happy and spacious home in one of Chicago's most architecturally significant and sought-after neighborhoods.

5041 S Dorchester Avenue Unit #2N, Chicago
$899,000
4 Beds ⋅ 4 Baths ⋅ 12743333 MLS ⋅ ACTIVE Status
APPRAISED AT $999,000-NOW OFFERED AT $899,000, A FULL $100,000 BELOW APPRAISED VALUE, WITH A PRIVATE TWO-CAR GARAGE INCLUDED. An exceptional new-construction opportunity at The Kenwood Reserve, an exclusive collection of just three boutique luxury residences tucked along a quiet, tree-lined cul-de-sac in historic Kenwood. This full-masonry, three-level, 4-bedroom, 3.5-bath residence delivers the space and privacy of a single-family home with the convenience, efficiency, and refined finishes of modern construction. Sun-filled interiors feature clean architectural lines, generous room proportions, and thoughtfully selected finishes throughout. The beautifully appointed kitchen is designed for both everyday living and effortless entertaining, with custom dark-wood Studio 41 cabinetry, stainless steel appliances, an oversized quartz island, and abundant storage. Select opportunities for buyer customization may still remain. Sliding glass doors extend the open-concept living space directly into a private backyard retreat-an exceptional feature ideal for dining outdoors, entertaining, relaxing, or creating a garden oasis. Combined with the included two-car garage and no monthly HOA assessment, the home offers a rare level of privacy, autonomy, and long-term value. The versatile lower level provides a warm secondary living space suited for a media room, lounge, playroom, fitness area, or home office, along with a private fourth bedroom ideal for guests or extended living. Moments from Hyde Park, the University of Chicago, lakefront parks, dining, and major cultural destinations, including the Obama Presidential Center in nearby Jackson Park, The Kenwood Reserve presents a compelling opportunity to own full-masonry new construction in one of Chicago's most architecturally distinguished neighborhoods. Preferred lender program available. Private tours now offered.

4719 S Ingleside Avenue, Chicago
$585,000
4 Beds ⋅ 3 Baths ⋅ 12741279 MLS ⋅ ACTIVE Status
Welcome to Woodlawn Manor. Stay in the Chicago that shaped history. The Obama Presidential Center opens this summer. We're handing you the keys to the neighborhood that started it all. Steps away from the Obama Presidential Center, this four-bedroom "penthouse" sits in the heart of historic Kenwood, minutes from the brand-new Obama Presidential Center and steps from the University of Chicago. It's a 1908 residence with the kind of grandeur you can't rebuild: mahogany walls and beams restored to a glow, original leaded glass framing the treetops, and rooms big enough for the whole crew to spread out and still find a quiet corner. The kitchen is a cook's dream with Sub-Zero and Wolf appliances, granite surfaces and two walk-in pantries. Whether you bring in a chef or prefer DIY meals, this space is built for long dinners, slow mornings, and the feeling of waking up where history is being made. Formal dining room designed for the ultimate host; it comfortably accommodates a table for 12 or more, making it the perfect stage for holiday gatherings and elegant dinner parties. Sleeps your family or your group in comfort. An added perk: in-unit laundry. Walk to everything. Beyond your front door, you are steps away from the University of Chicago, lush parks, and the vibrant dining and shopping scene of Hyde Park. Come for the opening. Stay for the neighborhood.

5054 S Woodlawn Avenue Unit #3C, Chicago
$36,900
1 Beds ⋅ 1 Baths ⋅ 12728372 MLS ⋅ ACTIVE Status
Find yourself at home in an abundance of natural light in this south facing 1 bed 1 bath co-op minutes from everything that sought-after Hyde Park has to offer. Easy access to University of Chicago, Metra, lakefront trail, Museum of Science and Industry, shopping, and award-winning restaurants. Assessments at this fully owner-occupied co-op include heat, AC, water, cable, real estate taxes, 24 hr. door staff, party room, laundry room, fitness center, interior and exterior maintenance. Parking available for additional per month cost. Rentals are not allowed.

4850 S Lake Park Avenue Unit #903, Chicago
$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
$5,100,000
12685129 MLS ⋅ ACTIVE Status
Exceptional opportunity to acquire a large multifamily asset featuring approximately 38 beds and positioned for shared housing, student housing, workforce housing, co-living, or short-term rental strategies. Located within close proximity to the University of Chicago and other major educational, healthcare, and employment centers, this asset presents a unique opportunity for investors seeking to capitalize on the growing demand for housing in one of Chicago's most active and rapidly evolving markets. The property's layout and scale make it particularly attractive for operators focused on shared housing initiatives, student accommodations, workforce housing, or alternative residential investment models. Its location near a world-renowned Ivy League-caliber institution and major neighborhood redevelopment activity creates multiple pathways for revenue generation and long-term value creation. This offering is being marketed confidentially. Financial information, property details, and exact location will be provided to qualified buyers upon request. Please contact the listing agent for additional information, financials, and access to the offering package.

Chicago
$1,695,000
6 Beds ⋅ 6 Baths ⋅ 12705893 MLS ⋅ ACTIVE Status
An extraordinary Kenwood greystone where historic craftsmanship takes center stage. Designed by celebrated Chicago builder Horatio Wilson, this remarkable 7-bedroom, 6-bath residence showcases more than 5,000 square feet of gracious living space, blending the grandeur of Chicago's architectural past with the comforts of modern living. Rich hardwood floors, extraordinary original millwork, handcrafted built-in cabinetry, decorative columns, pocket doors, and intricate wood detailing reflect a level of craftsmanship rarely found today. Formal living and dining rooms provide elegant spaces for entertaining and everyday living. Just beyond the dining room, a cozy lounge invites morning coffee or evening cocktails, while the adjoining butler's pantry offers a timeless transition into the kitchen. Tucked discreetly behind the kitchen, the original servant's staircase provides a charming connection between the home's first and second floors. Throughout the residence, seven fireplaces further celebrate its architectural heritage. The spacious primary suite serves as a private retreat with abundant closet space and a spa-inspired ensuite featuring a steam shower, soaking tub, dual vanities, and a walk-in closet. A finished lower level lives like a residence of its own with a second full kitchen, dining area, expansive family room, additional bedroom, and full bath-ideal for extended family, guests, or flexible living. Outside, a lush private garden offers a peaceful escape with mature landscaping and seasonal blooms. Ideally situated on a picturesque, tree-lined block in Kenwood near Hyde Park and the University of Chicago, this exceptional residence places you among one of Chicago's most architecturally significant neighborhoods, surrounded by historic homes, cultural institutions, acclaimed dining, and everyday conveniences. Homes of this caliber rarely become available, offering the opportunity to own not simply a remarkable residence, but an enduring chapter in Chicago's architectural story.

4942 S Ellis Avenue, Chicago
$2,371,500
5 Beds ⋅ 6 Baths ⋅ 12711888 MLS ⋅ ACTIVE Status
An exceptional expression of architectural elegance and refined living, this distinguished 6-bedoom, 5.5-bath Kenwood residence offers the rare combination of grandeur, scale, and gracious comfort. Set on one of the neighborhood's most beautiful, tree-lined streets, this magnificent early 20th-century home is distinguished by its handsome brick facade, generous proportions and timeless craftsmanship, along with many significant modern upgrades. Spanning approximately 6,700 square feet, the residence unfolds across an impressive and thoughtfully designed floor plan, with soaring ceilings, exquisite hardwood floors, elegant millwork, and a wealth of original architectural character. The gracious entry leads to beautifully proportioned formal rooms, including an expansive living room anchored by a fireplace and an elegant dining room designed for memorable entertaining. The sophisticated yet inviting kitchen features top-quality stainless-steel appliances, a substantial center island, farmhouse sink, and abundant cabinetry, creating a refined setting for both intimate meals and large-scale gatherings. A private den offers an ideal retreat for work or relaxation. The sumptuous primary suite is a true sanctuary, featuring generous proportions, two large walk-in closets, and a luxurious marble bath with dual vanities, a deep soaking tub, and separate shower. Additional bedrooms are also generously sized and complemented by beautifully appointed baths, offering exceptional comfort and privacy. The lower level further enhances the home's remarkable livability, with an expansive finished recreation room featuring built-in shelving, and recessed lighting -- an ideal setting for casual entertaining, recreation. A separate guest room with private full bath completes this level. Outside, meticulously landscaped grounds create a private and serene urban oasis, complemented by a spacious backyard and a concrete drive from the street leading to a detached two-car garage. Perfectly positioned near the lakefront, parks, premier schools, downtown transportation, and the cultural and academic institutions of the greater Hyde Park community, 4900 S. Kimbark Avenue represents a rare opportunity to experience the grandeur of a classic Chicago residence with the comfort and sophistication of modern living. The home is truly in move-in condition, having undergone extensive mechanical & structural renovations from sub-foundation to roof, including multi-zone radiant heat and air conditioning, continuous hot water, 400 AMP electrical service, and replaced water, gas and sewer lines.

4900 S Kimbark Avenue, Chicago
$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
$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
$425,000
4 Beds ⋅ 2 Baths ⋅ 12675404 MLS ⋅ ACTIVE Status
For the first time in 47 years, a rare value-add opportunity in the heart of historic Kenwood Mansion District. This spacious 4-bedroom, 1.1-bath townhome offers three levels of living space, including a partially finished basement and a large private fenced yard. Solid brick and concrete construction provides the perfect foundation for renovation, with tremendous upside for investors or owner-occupants looking to build equity. Featuring 4 bedrooms on one level, this home offers a functional layout that can easily be reimagined for modern living. Ideally located just blocks from the neighborhood gem, Kenwood Community Park, and close proximity to Metra, Lake Michigan, Lake Shore Drive, Jackson Park, the University of Chicago, and the recently finalized Obama Presidential Center. Surrounded by some of Chicago's most distinguished homes, this property presents a unique chance to renovate and live in one of the South Side's most sought-after neighborhoods.

4753 S Woodlawn Avenue, 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
$385,000
3 Beds ⋅ 2 Baths ⋅ 12581893 MLS ⋅ ACTIVE Status

1354 E 48Th Street Unit #2E, Chicago
$57,500
3 Beds ⋅ 2 Baths ⋅ 12488616 MLS ⋅ ACTIVE Status

4850 S Lake Park Avenue Unit #702B, Chicago
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