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, Chicago IL Market Snapshot

Inventory here shifts week to week. The listings on this page pull straight from the MLS, so what you see is what's actually for sale right now.

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Homes for Sale in Kenwood, Chicago IL

$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
$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
$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
$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
$249,000
3 Beds ⋅ 1 Baths ⋅ 12699647 MLS ⋅ CONTINGENT Status
Spacious 3-bedroom condo in the heart of Hyde Park/Kenwood! Set within a charming 1905 vintage brick building, this sun-filled second-floor home offers timeless character, generous living space, and exceptional value in one of Chicago's most vibrant neighborhoods. Inside, you'll find hardwood floors throughout, abundant natural light, generously sized rooms, an eat-in kitchen, and a private back deck perfect for grilling, relaxing, or enjoying your morning coffee. The functional floor plan provides flexibility for everyday living, working from home, or entertaining guests. Move right in or bring your ideas-this home offers a fantastic opportunity to personalize and build equity over time. The building features private storage and shared laundry, with the possibility of adding in-unit laundry for added convenience. Easy street parking makes city living even more manageable. With no rental restrictions, this investor-friendly building offers excellent flexibility, whether you're searching for a primary residence, University of Chicago housing, or an income-producing property. Enjoy an unbeatable location just steps from Whole Foods, Trader Joe's, Target, neighborhood restaurants, coffee shops, parks, and public transportation. You're also minutes from the University of Chicago, the Museum of Science and Industry, Jackson Park, the lakefront, and the shopping and dining along 53rd Street. Combining vintage Hyde Park charm, generous living space, and an outstanding location, this home presents an exceptional opportunity to own in one of Chicago's most sought-after neighborhoods.

5052 S Blackstone Avenue Unit #2, Chicago
$645,000
4 Beds ⋅ 3 Baths ⋅ 12684895 MLS ⋅ CLOSED Status
This very special 8-flat building, located in highly desirable, private Madison Park was completely renovated 15 years ago with all new plumbing, electrical, and HVAC systems throughout. The resulting condominium apartments are beautifully laid out and offer an unbeatable combination of move-in condition, modern style, and one-of-a-kind location. Outstanding features include an open floor plan with amazing park views, bamboo flooring throughout, individually controlled heat and a/c systems, granite counter tops, Grohe faucets, Jenn Air duel fuel stove, in-unit laundry, and exquisite finishes. Strong, well-run homeowners association association with low monthly fees and taxes. Assigned storage locker on the ground level. Sticker parking for Madison Park is $440 annually.

1215 E Madison Park Avenue Unit #3, Chicago
$780,000
5 Beds ⋅ 3 Baths ⋅ 12682285 MLS ⋅ CLOSED Status
Fully Renovated, Sun-Filled Madison Park Condo! Spacious 3rd-floor residence featuring 45 oversized new windows, solid oak floors, elegant moldings, and two bright sunrooms. Expansive living spaces blend historic charm with modern updates throughout. The chef's kitchen offers a large island, quartz countertops, abundant cabinetry, and a walk-in pantry. The luxurious primary suite includes a spa-like bath with marble tile, double vanity, soaking tub, oversized shower, and private water closet. Enjoy radiant heat, central air, supplemental GFA heating, a large private storage room, and two Madison Park parking permits. Prime location near parks, the lakefront, public transportation, University of Chicago, Hyde Park, and downtown Chicago. A rare opportunity to own a beautifully updated home in historic Madison Park. **Owner finance potential with good downpayment and decent credit!!***

1201 E Madison Park Drive Unit #3, Chicago
$399,500
4 Beds ⋅ 2 Baths ⋅ 12675404 MLS ⋅ PRICE CHANGE Status
For the first time in 47 years, a rare value-add opportunity in the heart of the historic Kenwood Mansion District. This 4-bedroom, 1.1-bath townhome offers a functional three-level layout, including a partially finished basement, a private fenced yard, and access to a shared private community park-providing exceptional outdoor space in the city. Solid brick and concrete construction provides a strong foundation for renovation, with potential for owner-occupants looking to build equity. All four bedrooms are conveniently located on one level, however, some owners have reimagined the space and combined two bedrooms to make a large primary suite. Ideally located near Kenwood Community Park, Metra, Lake Michigan, Lake Shore Drive, Jackson Park, the University of Chicago, and the Obama Presidential Center. Surrounded by some of Chicago's most distinguished homes, this is a unique opportunity to renovate and create a home of your own in one of the Chicago's most sought-after neighborhoods.

4753 S Woodlawn Avenue, Chicago
$652,000
4 Beds ⋅ 3 Baths ⋅ 12663757 MLS ⋅ CLOSED Status
This renovated 4-bedroom 2.5-bath home in the desirable Kennicott Place enclave offers immediate, effortless living in one of Hyde Park-South Kenwood's most established and convenient pockets. No deferred maintenance, no to-do list, Unit F is just a beautifully updated single-family residence ready for its next chapter. The heart of the home is an expansive, suburban-inspired kitchen with quartz countertops, ample cabinetry, and stainless steel appliances installed in 2020. Thoughtful, recent enhancements elevate every level: the primary and secondary full and half bathrooms have been completely refreshed (2025 and 2026), complemented by a new fireplace surround and sophisticated second-floor entry tile (both 2026). The exterior was fully painted in 2025. A dedicated new laundry center with integrated folding counter, storage and washer and dryer with extended warranties to 2029 were added in 2025. Mechanical peace of mind includes a roof replacement (2019), upgraded R-49 attic insulation (2021), water heater (2020), and modern heat pump/furnace (2023). New full view storm doors and mailbox (2026 - installed post pics). The property extends outdoors to professionally landscaped front and rear yards, fully refreshed in 2025, providing rare private green space. Parking remains exceptionally convenient with a private driveway and dedicated front space accommodating up to three vehicles. Positioned 1 mile from the University of Chicago campus, you're immersed in the best of Hyde Park and Kenwood: the intellectual vibrancy of the University, proximity to the Metra and lakefront, Washington Park, the boutique shops and acclaimed restaurants of 53rd Street, and the cultural depth that defines this historic South Side neighborhood.

4701 S Woodlawn Avenue Unit #F, Chicago
$330,000
3 Beds ⋅ 2 Baths ⋅ 12653031 MLS ⋅ CLOSED Status ⋅ City Haven Condominiums BLDG.
Get ready to fall in love with this luxurious penthouse condo in the opulent Kenwood Landmark District!!! This spacious and sun-drenched condo offers 1800 sqft of living that makes you feel like you're on the cover from a magazine. Let's start with location, location, location; you're located in a cul-de-sac and surrounded by some of the most beautiful estates that Chicago has to offer. Walking in this neighborhood gives you the feeling like you're in a scene from the Great Gatsby! The condo itself feels fun and full of splendor. You're greeted by a long hallway that leads to a semi-open floor plan the offers a dining room, living room, kitchen, and solarium that brings in plenty of light and fresh air. The kitchen has an island with seating for a couple of chairs or can be used as a pass-thru when entertaining (which you'll want to do plenty of when living here). Kitchen is equipped with stainless steel appliances and ample cabinetry. The entire condo has hardwood oak floors and in the hallway you have a very modern full bath, full sized stackable washer & dryer, and mechanical closet. This brings us to the primary bedroom and bath... The bedroom is spacious, offers a walk-in closet, and an on-suite that provides that perfect place to relax and feel pampered. Dual sinks, rain shower, and full soaker tub round out this spacious bathroom. There are two more good size bedrooms and the home also offers tandem parking for 2. That's right, parking for 2 cars. The home has too many smart home features to mention here but I should mention there is also a storage locker included in the basement. This is an excellent opportunity at this price point!

4740 S Ingleside Avenue Unit #3S, Chicago
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