Kenwood, Chicago IL · Curated MLS Search

Homes for Sale in Kenwood, Chicago IL

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

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About Homes for Sale in Kenwood, Chicago IL

Kenwood sits on Chicago's South Side, just north of Hyde Park, and it doesn't hide what it is. Mansions and greystones run block after block here, some of the grandest housing stock in the city. Old trees throw shade across the sidewalks. And it's quiet, which throws people who assume every city street has to roar.

You're a short hop from the lake, from the University of Chicago, from the museums that hold down this stretch of town. North Kenwood reads differently than the blocks near the water. Each has its own rhythm. People who move here don't leave. That tells you most of what you need to know.

Why Buy Homes for Sale in Kenwood, Chicago IL?

Buy here if you want room, real architecture, and neighbors who care about where they live. The lakefront, the university, downtown by train: all close. And you skip North Side prices to get there. Homes at this scale, with this kind of craftsmanship, are drying up across Chicago. Kenwood still has them. Worth every dollar.

Ready to find your ideal homes for sale in Kenwood? Contact Chicago Real Estate Source today at (312) 788-7079 to schedule a showing or start your personalized home search.

Kenwood Market Snapshot

Live MLS data — Kenwood

Kenwood
inventory
Active Listings
29
Sold (Past 6 Mo.)
33
Under Contract
4
pricing
Avg. List Price
$1,048,934
Cost / Sq. Ft.
$239
typical home
Living Area
2,863 ft²
Avg. Beds
3.7
Avg. Baths
3.1
Days on Market
76

Homes for Sale in Kenwood, Chicago IL: Housing Market Data

Data as of (MLS snapshot; listings below update live)

Chicago Real Estate Source's review of MLS data as of October 20, 2026 shows 21 Kenwood homes for sale priced at $100,000 or more, out of 29 active listings across every property type. Asking prices had a median of $925,000, about $306 per square foot, for a median of 2,800 square feet. The middle half of these listings was priced between $390,000 and $1,850,000. A typical listing had been on the market 42 days.

Kenwood, Chicago IL homes for sale, October 20, 2026
MeasureValue
Active listings21
All active listings in Kenwood, every property type29
Median list price$925,000
Middle half of list prices$390,000 to $1,850,000
Median price per square foot$306
Median square feet2,800
Median days on market42

Homes for Sale in other neighborhoods

Market questions

How many Kenwood homes are listed for sale?

As of October 20, 2026, there were 21 Kenwood homes for sale priced at $100,000 or more, out of 29 active listings across every property type, based on Chicago Real Estate Source's review of MLS data.

What is the median price of Kenwood homes?

The median list price of Kenwood homes was $925,000 as of October 20, 2026.

Where do most asking prices for Kenwood homes fall?

The middle half of active listings for Kenwood homes was priced between $390,000 and $1,850,000.

What is the typical price per square foot for Kenwood homes?

The median price per square foot for Kenwood homes was $306, for a median of 2,800 square feet.

What is the typical time on market for Kenwood homes?

The median listing for Kenwood homes had been on the market 42 days as of October 20, 2026.

How do Kenwood homes compare with other neighborhoods?

As of October 20, 2026, there were 21 Kenwood homes for sale priced at $100,000 or more. In the same search, Chicago had 5,362 homes for sale at a median list price of $414,900, Naperville had 343 homes for sale at a median list price of $634,000 and Aurora had 328 homes for sale at a median list price of $399,875.

Listing data courtesy of Midwest Real Estate Data LLC.

Next Steps in Kenwood, Chicago IL

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Reply from Chicago Real Estate Source

Homes for Sale in Kenwood, Chicago IL

4717 S Ingleside Avenue, Chicago
$999,000
4 Beds ⋅ 4 Baths ⋅ 12792798 MLS ⋅ NEW 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. 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.

4717 S Ingleside Avenue, Chicago
4840 S Dorchester Avenue Unit #11, Chicago
$1,150,000
4 Beds ⋅ 4 Baths ⋅ 12790678 MLS ⋅ NEW 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. 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 1.5 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 #11, Chicago
4716 S Ingleside Avenue Unit #2N, Chicago
$324,900
2 Beds ⋅ 2 Baths ⋅ 12786114 MLS ⋅ ACTIVE Status
Welcome to 4716 S. Ingleside Avenue Unit 2N, where generous proportions, sophisticated updates, and abundant natural light come together in an exceptionally spacious 1,800-square-foot, 2-bedroom, 2-bath condominium. Featuring a kitchen and baths renovated in 2023, gleaming hardwood floors throughout, in-unit laundry, and remarkably generous living spaces, this residence offers the scale and comfort of a single-family home with the ease of condominium living. The expansive living and dining room combination is the home's centerpiece, an impressive, light-filled space that offers tremendous flexibility for everyday living and entertaining. Generous windows welcome abundant natural light, while a handsome fireplace anchors the room, creating an inviting focal point and adding character to the home's gracious proportions. The kitchen, renovated in 2023, combines contemporary style with everyday functionality. Stainless steel appliances, updated finishes, and a dedicated eating area create an inviting setting for casual dining, while ample workspace makes everyday cooking and entertaining effortless. The oversized primary suite offers exceptional space and privacy, a true retreat within the residence. A generous walk-in closet plus a secondary closet provide abundant storage, while the beautifully renovated primary bath adds modern comfort. The suite is completed by a private balcony, offering a personal outdoor escape for fresh air, relaxation, or unwinding at the end of the day. The generously proportioned second bedroom provides flexibility for family, overnight guests, or an executive home office. A second renovated full bathroom adds convenience while maintaining the home's cohesive, updated presentation. In addition to generous in-unit closet space and the convenience of an in-unit washer and dryer, the condominium includes assigned storage for seasonal belongings and everyday essentials. Perfectly positioned in South Kenwood, just minutes from Hyde Park and the University of Chicago, this residence places shopping, dining, education, culture, recreation, and the lakefront within easy reach. Enjoy convenient access to Whole Foods Market, Trader Joe's, and Hyde Park's vibrant 53rd Street shopping and dining district. Nearby lakefront and cultural destinations include Promontory Point, Lake Michigan, the Lakefront Trail, Jackson Park, Jackson Park Golf Course, the Obama Presidential Center, the Griffin Museum of Science and Industry, Washington Park, and the Midway Plaisance. The surrounding South Kenwood and Hyde Park community offers convenient access to a variety of educational institutions, including the University of Chicago Laboratory Schools, Kenwood Academy, Ariel Community Academy, and Shoesmith Elementary School, along with additional public and private educational options throughout the area. The University of Chicago and UChicago Medicine are also just minutes away. DuSable Lake Shore Drive is just moments away, providing convenient access to downtown Chicago and the lakefront. Nearby Metra Electric service, CTA bus routes, and CTA rail connections provide additional transportation options throughout the city. This is more than a condominium; it is gracious city living on a scale rarely found today, combining exceptional space, beautifully updated interiors, a private outdoor retreat, and an enviable South Kenwood location.

4716 S Ingleside Avenue Unit #2N, Chicago
4941 S Kimbark Avenue, Chicago
$1,595,000
5 Beds ⋅ 4 Baths ⋅ 12786855 MLS ⋅ ACTIVE Status
Beautifully updated and move-in ready, this exceptional 3-story brick home on a coveted Kenwood block offers over 4,700 square feet of living space, 5+ bedrooms, 3 1/2 baths, and a fully finished and thoughtfully designed basement. A spacious, covered front porch welcomes you home, offering multiple seating areas and a ceiling fan for comfortable outdoor enjoyment even on the warmest days. Inside, the inviting entry hall opens seamlessly into the gracious living room, featuring a beautiful gas fireplace and built ins. The elegant separate dining room, with its handsome built-in cabinetry, is perfectly positioned between the living room and kitchen, connecting to the kitchen through an open butler's pantry. The spacious eat in kitchen is outfitted with a 2025 premium appliance package, including a Sub-Zero refrigerator, Viking cooktop, Wolf double oven and microwave, and Bosch dishwasher. Just off the kitchen, a large newly refinished deck overlooks the beautiful professionally landscaped yard and leads down to a full-size sport court -- an incredible amenity for recreation and entertaining. A conveniently tucked-away powder room is located beneath the staircase on the main floor. Up the grand staircase, the 2nd floor features a beautifully renovated custom office (with a discreetly integrated full-size washer and dryer), 2 generously sized bedrooms, a cozy family room, and a newly updated full bath. The 3rd floor offers a private primary suite with a newly renovated spa-like bath including radiant heated floors and a large walk in closet. Also on this level are another large bedroom, a fully renovated hall bath, and a versatile 2nd office or 5th bedroom. The fully finished lower level provides an expansive recreation room with endless possibilities-as a family room, play area, craft space, home gym, or whatever best suits your needs. A separate laundry area with sink, large walk-in pantry, second refrigerator and abundant additional storage add to the functionality of this level, which also offers convenient walk-out access to the backyard. Newer mechanicals include heat pump and space pack and 2 water heaters. The flat roof lining was replaced around 2017. This exceptional home combines beautiful original character with thoughtful updates, generous living space, and an impressive array of indoor and outdoor amenities. Truly move-in ready, it offers everything you have been looking for in a beautiful Kenwood home. Easy access to Lake Michigan, downtown transportation, and the University of Chicago campus.

4941 S Kimbark Avenue, Chicago
5041 S Dorchester Avenue Unit #2N, Chicago
$394,900
3 Beds ⋅ 2 Baths ⋅ 12786353 MLS ⋅ ACTIVE Status
Located in the historic South Kenwood Landmark District, this beautifully maintained 3-bedroom, 2-bath residence at 5041 S. Dorchester offers a blend of historic charm and modern comfort. Situated on the second floor of a boutique five-unit building, the home overlooks Madison Park with peaceful treetop views and includes TWO deeded parking spaces in a secure gated lot. The building 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. 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
1140 E Hyde Park Boulevard Unit #3D, Chicago
$439,900
4 Beds ⋅ 2 Baths ⋅ 12774491 MLS ⋅ CONTINGENT 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
1354 E 48Th Street Unit #2E, Chicago
$385,000
3 Beds ⋅ 2 Baths ⋅ 12774294 MLS ⋅ ACTIVE Status
Over 2,000 SQ FT | KENWOOD LEGACY ASSET | Experience the power of scale and heritage in this sprawling 2,000 sq. ft. second-floor condo, perfectly positioned in Chicago's Kenwood neighborhood. This is more than a home. Boasting soaring 12-foot ceilings and intricate architectural details, this 3-bedroom, 2-bath offers the volume and character that modern construction cannot replicate. The expansive floor plan features a grand foyer, a living room anchored by a classic fireplace, and custom-built bookshelves by Arthur Levin. The primary bedroom features a unique vanity transition and shutter-door privacy. With an entertainer's floor plan, you will enjoy a grand foyer, massive formal dining room with bay windows and a large private rear porch overlooking the backyard. In-unit laundry included. Steps from the lakefront and elite dining like Virtue and 14 Parish. Seize this rare opportunity for wealth arbitrage in Chicago's most culturally significant corridor. Position yourself in the heart of Kenwood, schedule your private tour today. Monthly HOA includes:Heat, Water, Common Insurance, Security, Lawn Care, Scavenger, Snow Removal

1354 E 48Th Street Unit #2E, Chicago
4710 S Ellis Avenue Unit #3N, Chicago
$314,000
3 Beds ⋅ 2 Baths ⋅ 12771807 MLS ⋅ ACTIVE Status

4710 S Ellis Avenue Unit #3N, Chicago
4939 S Dorchester Avenue Unit #5F, Chicago
$147,000
1 Beds ⋅ 1 Baths ⋅ 12767252 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
4711 S Greenwood Avenue, Chicago
$1,925,000
12758275 MLS ⋅ ACTIVE Status
Finally available! Where the Hot Bronzeville/Woodlawn/Kenwood/Hyde Park Neighborhoods intersect sits this "Value-Add" 7 Unit investment opportunity. 4 Units, now vacant, have been Occupied by family members for several decades with the 3 remaining units on MTM/ below market rentals. Many of the original features are still intact: Pocket Doors, Paneled Walls, Butlers Pantry, Built in China Cabinets and Bookcases, French Doors, Cofferred Ceilings, Decorative Fireplaces, Tile floor staircases, Sunrooms, Jack and Jill Baths, Crown Molding! With a newer roof, central stairwell skylight and updated circuit breakers, the Building has 'Great Bones', making it a fabulous candidate for Value Add updates and cosmetic work, optimizing rentals to current market rates. Easy Access to Public Transportation, University of Chicago and the University of Chicago Medical Center, the Obama Library and the Lakefront.

4711 S Greenwood Avenue, Chicago
4901 S Kimbark Avenue, Chicago
$2,295,000
8 Beds ⋅ 6 Baths ⋅ 12702363 MLS ⋅ ACTIVE Status
Located in the heart of the South Kenwood historic landmark district, 4901 S Kimbark Avenue offers a rare opportunity to own a distinguished residence in one of Chicago's most architecturally significant neighborhoods. Surrounded by stately homes, mature trees, and picturesque streets, this exceptional property combines timeless character with an unbeatable location just moments from the University of Chicago campus, Jackson Park, the Museum of Science and Industry, and the lakefront. The imposing 3-story home has impressive curb appeal, including an inviting wrap-around porch and mature plantings. A private side yard provides a verdant refuge for play and outdoor dining. The new 2+ car garage is a real plus. Inside, the 8-bedroom, 5.5 bath home showcases generous living spaces, abundant natural light, and classic architectural details that reflect Kenwood's rich heritage. Spacious formal rooms are complemented by comfortable everyday living areas, creating an ideal setting for both entertaining and daily life. Among the many outstanding features is the beautifully designed modern eat-in kitchen with top-of-the-line appliances and the fully-finished lower level with a spacious recreation room, separate work-out room, and a new full bath. New water service, zoned a/c, and updated systems throughout. The location is second to none. Residents enjoy easy access to acclaimed restaurants, neighborhood cafes, shopping, cultural institutions, Metra and CTA transportation downtown, and the scenic paths and beaches along Lake Michigan. Jackson Park's ongoing improvements and the renowned Obama Presidential Center further enhance the appeal of this vibrant community. Whether you're seeking a remarkable historic residence or an elegant home in one of Chicago's most desirable neighborhoods, 4901 S Kimbark Avenue offers an exceptional blend of architectural character, urban convenience, and enduring value.

4901 S Kimbark Avenue, Chicago
1364 E 49Th Street, Chicago
$1,350,000
5 Beds ⋅ 4 Baths ⋅ 12755340 MLS ⋅ PENDING Status

1364 E 49Th Street, Chicago
1203 E 50Th Street, Chicago
$1,675,000
4 Beds ⋅ 4 Baths ⋅ 12711971 MLS ⋅ ACTIVE Status
Designed by renowned modernist architect Tony M. Grunsfeld, this mid-century gem highlights architect's love for clean lines, minimalist design and above all, natural flow from inside to the outside world. This house built in 1965, has been recently fully renovated. When entering the house one is immediately drawn to the expansive living room with its' three floor-to-ceiling double glass doors that open the space onto a lush, oversized backyard full of blooming flowers. Spacious chef's kitchen, features lots of counter space and storage, beautiful cabinets and high end appliances . This delightful space is flooded with light from a set of floor-to-ceiling glass doors and opening to the light filled living room. First level features also an office/guest bedroom and a half bath. Four spacious bedrooms are all located on the second floor. Primary bedroom has en-suite bathroom with double sink and two large walk-in closets. Additional two bedrooms and one office (originally a bedroom) share a beautiful bathroom with a bathtub. Comfortable family room and a gym are located in the basement. In addition, there is a large storage space, mechanical area and laundry as well as additional half bath on the lower level. All wooden floors are oak, while the entry hall floor is covered with stone ties. This is a unique home with simple beauty, inviting, light filed space and a very comfortable interior. Recent major updates: HVAC system 2022, new sewer line to the street, direct vent gas fireplace 2024.

1203 E 50Th Street, Chicago
1209 E Madison Park Boulevard, Chicago
$2,729,000
12755416 MLS ⋅ ACTIVE 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
4731 S Ingleside Avenue Unit #A3, Chicago
$229,999
2 Beds ⋅ 2 Baths ⋅ 12755276 MLS ⋅ ACTIVE 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
4923 S Greenwood Avenue, Chicago
$2,175,000
8 Beds ⋅ 5 Baths ⋅ 12752094 MLS ⋅ ACTIVE 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
4801 S Kimbark Avenue, Chicago
$1,775,000
6 Beds ⋅ 5 Baths ⋅ 12753755 MLS ⋅ ACTIVE Status

4801 S Kimbark Avenue, Chicago
4719 S Ingleside Avenue, Chicago
$899,000
4 Beds ⋅ 4 Baths ⋅ 12743333 MLS ⋅ ACTIVE Status
APPRAISED AT $999,000 - NOW OFFERED AT $899,000! An exceptional opportunity to own move-in-ready luxury new construction for $100,000 below appraised value, with a private two-car garage included! Welcome to The Kenwood Reserve, an exclusive collection of just three full-masonry residences tucked along a quiet, tree-lined cul-de-sac in Chicago's desirable Hyde Park-Kenwood area. Offering the privacy and independence of single-family-style living, this thoughtfully designed, three-level home with private entry features 4 bedrooms, 3.5 bathrooms, a private backyard, two-car garage, and no monthly HOA assessment. Sun-filled interiors showcase clean architectural lines, refined contemporary finishes, and an inviting open-concept layout designed for both everyday comfort and entertaining. The beautifully appointed kitchen features custom dark-wood Studio 41 cabinetry, stainless steel appliances, an oversized quartz island, and abundant storage. Sliding glass doors seamlessly connect the main living space to a private backyard retreat, ideal for outdoor dining, entertaining, gardening, or simply relaxing in your own outdoor oasis. The finished lower level provides a versatile second living area perfect for a media room, lounge, playroom, fitness space, or home office, along with a private fourth bedroom ideal for guests or extended family. Full-masonry construction, modern systems, fee-simple ownership, and private outdoor living distinguish The Kenwood Reserve from traditional condominium living. Select opportunities for buyer customization may still be available. Ideally situated near Hyde Park, the University of Chicago, public transportation, lakefront parks, neighborhood dining, and cultural attractions, including the Obama Presidential Center in nearby Jackson Park. With a recent appraisal of $999,000 and an asking price of $899,000, this is a compelling opportunity to enjoy thoughtfully designed new construction with the freedom of no monthly HOA assessment. Preferred lender financing options may be available to qualified buyers. Private showings now available! INVESTOR FRIENDLY, no rental restrictions.

4719 S Ingleside Avenue, Chicago
5054 S Woodlawn Avenue Unit #3C, 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
4731 S Ingleside Avenue Unit #D1, Chicago
$299,900
2 Beds ⋅ 3 Baths ⋅ 12723335 MLS ⋅ ACTIVE Status
Spacious 2-Bedroom, 2.5-Bath Duplex with Assigned Exterior Parking! Discover the space and versatility of this beautifully maintained two-level condo, ideally situated on a quiet, tree-lined cul-de-sac in Chicago's desirable Kenwood neighborhood. This spacious duplex offers the comfort of townhome-style living, featuring hardwood floors on the upper level, a contemporary kitchen with cherry cabinetry, granite countertops, stainless steel appliances, and generous space for everyday living and entertaining. The upper level features two generously sized bedrooms, including a primary suite with a private bath. The second bedroom offers direct access to another full bathroom. A versatile flex space provides the perfect setting for a home office, reading area, or additional living space. The lower level offers additional room to relax or entertain, complemented by updated flooring and newer windows. Additional highlights include in-unit laundry, a convenient powder room, a private rear balcony, generous storage, and one assigned exterior parking space included with the unit (not deeded separately). Conveniently located near neighborhood restaurants, shopping, the University of Chicago, public transportation, and the lakefront, this home offers a wonderful combination of space, comfort, and accessibility.

4731 S Ingleside Avenue Unit #D1, Chicago
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NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

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