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$500,000
4 Beds 2 Baths 12466703 MLS CLOSED Status
Historic Greystone just steps from the University of Chicago! This beautifully updated and spacious 4-bedroom, 2-bath condominium seamlessly blends vintage charm with modern comfort. Perfectly positioned just steps from the University of Chicago and The Laboratory Schools, this residence occupies the entire third floor of a classic greystone. Inside, abundant natural light fills every room, highlighting original hardwood floors, gleaming period woodwork, and a stylish fireplace surrounded by built in bookshelves. The enlarged kitchen and tastefully renovated bathrooms provide contemporary convenience, while the home's freshly painted interiors preserve its timeless elegance. Enjoy tree-top views, outdoor living on the large private deck overlooking a landscaped yard, plus a skylit entry, a full size washer/dryer in the basement, generous basement storage, and a lush communal yard and garden. This self-managed, well-maintained building boasts a strong, stable association and sits within one of Chicago's most historic and picturesque neighborhoods - the perfect combination of space, charm, and unbeatable location. Welcome home!

5741 S Kenwood Avenue Unit #3, Chicago

$2,750,000
6 Beds 9 Baths 12446282 MLS CLOSED Status
5638 South Woodlawn Avenue represents a unique opportunity to own a piece of Chicago's architectural heritage. Designed in 1911 by celebrated architect Howard Van Doren Shaw for publishing executive Henry Hoyt Hilton and his wife Charlotte, this three-story Federal-style residence embodies timeless elegance and thoughtful design. Shaw, later honored with the American Institute of Architects' Gold Medal, was renowned for his refined use of symmetry, proportion, and classical detail-hallmarks clearly evident here. Meticulously restored and updated, the massive 8,000-square-foot home blends original grandeur with modern luxury. Historic details - majestic fireplaces, gleaming hardwood detailing, and an elegant main staircase-are complemented by a new chef's kitchen, renovated baths, a reimagined third-floor great room, as well as the practical including a spacious laundry. The lower level adds a workout room, media room, and abundant storage. With six bedrooms, five full ensuite baths, and three half baths, this residence offers both scale and versatility for modern living. Set in the heart of the University of Chicago community, this historic property is as livable as it is significant - a piece of architectural history, seamlessly blending Shaw's timeless vision with contemporary elegance in one of Chicago's most celebrated neighborhoods.

5638 S Woodlawn Avenue, Chicago

$267,000
3 Beds 2 Baths 12452808 MLS CLOSED Status Ingleside Comdominiums BLDG.
Beautifully designed living and dining rooms sit side by side, opening into a bright sunroom overlooking a leafy street lined with mature trees. The entire condo-including closets-has been freshly painted, and genuine hardwood floors shine throughout. The original fireplace with vintage tile surround now features a gas log insert, perfect for cozy evenings as the weather cools, while four air conditioning units provide comfort in warmer months. Two of the AC units were new in 2021 and the portable unit was new in 2022. The kitchen and butler's pantry have been updated with white cabinetry, stainless steel appliances, and a garbage disposal and reverse osmosis water filter from 2020. The dishwasher was replaced in 2023. Bedrooms and the dining room feature updated ceiling fans and light fixtures, and sparkling clean windows flood the home with natural light. The shared primary bath offers a new vanity and mirror along with a reglazed vintage tub. The laundry machines located in their own hall closet were new in 2020 and there is even a laundry sink (which is hard to find these days). Move-in ready, this pet-friendly association allows two pets per unit (up to 85 lbs. each) and requires contracts be submitted 30 days prior to closing. A recently replaced boiler was covered by a special assessment, which the sellers will settle in full at closing. Ideally located just blocks from the University of Chicago, 53rd Street's dining scene, Whole Foods, Trader Joe's and the lakefront, the home earns high Walk Score ratings for walkability, bikeability, and transit. Buses run along East Hyde Park Boulevard with connections to express routes, Metra, and the Red and Green Lines, plus an express bus to the Loop is just a couple of blocks away. Residents also share a rear parking space for deliveries and moving. Sunny back porch too!

5202 S Ingleside Avenue Unit #2, Chicago

$299,000
1 Beds 1 Baths 12435234 MLS CLOSED Status
Welcome to all the beauty of a bygone era in this 1920's, with the luxury of 2025. This large one bedroom unit features a decorative fireplace and architectural detail throughout! This Hyde Park gem designed by Prairie architect Robert Spencer, combines space and elegance. Enjoy a combined living -dining area for entertaining or just having room to spread out! Leisurely sip coffee or wine on the balcony just off living room. This is "The Mews" which is an iconic building in Hyde Park and well placed for the University of Chicago. Recent renovation of the unit includes in-unit laundry, walk in shower, refinished floors, central air conditioning, rehabbed windows and a fabulous new kitchen. It is one block from restaurants (including famous Medici bakery and restaurant), book stores, and various other businesses in Hyde Park. Also buses, trains and expressways are not far to use when needed. Walk to Laboratory School or other University of Chicago buildings. You will be in the best place in Hyde Park!

1368 E 57Th Street Unit #3, Chicago

$1,312,500
4 Beds 4 Baths 12409365 MLS CLOSED Status
A special home on Harper in move-in condition with garage parking! This thoughtfully redesigned Victorian home is perfectly situated on one of Hyde Park's most popular and charming blocks. Highly upgraded by the current owners, the resulting 5-bedroom, 3.5-bath home retains an abundance of historic vintage detail (high ceilings, hardwood floors), plus numerous modern upgrades, including central a/c, new baths and kitchen, and a wonderfully finished basement. The newly-redesigned open kitchen comes with hardwood cabinets, stone counters, a professional grade stove and hood, and a separate breakfast area. The basement has been recently completely renovated to include a TV/gaming area, an additional bedroom (perfect for guests and/or teens), and a modern full bath. Spacious deck off the dining room overlooks the deep, grassy backyard. Easy walking distance to downtown transportation, the shops on 57th Street, the University of Chicago campus, and both Lab School locations.

5729 S Harper Avenue, Chicago

$454,000
3 Beds 2 Baths 12417270 MLS CLOSED Status
Fully renovated apartment on a quiet tree lined street in the heart of Hyde Park. Nestled in a classic brick and limestone building on an oversized lot, this home was completely reimagined with a focus on flow, light, and luxury. This gorgeous 3BR 2BTH unit has 8 ft ceilings throughout & huge private outdoor patio! A private entrance leads to a spectacular living space with a stunning gas fireplace. The living spaces open to the chef's kitchen which features white shaker cabinetry with crown molding, waterfall quartz counters, chef-grade stainless steel appliances: exhaust, French door refrigerator, range, dishwasher, and microwave - ideal for entertaining or everyday elegance. The adjacent dining room doubles perfectly as a formal space or additional multipurpose living space. The primary suite offers a custom walk-in closet and a spa-inspired bath, complete with a multi-jet walk-in shower and rainfall showerhead. In addition, there is one garage parking spot, in-unit laundry, pet-friendly building, and a recently renovated shared backyard round out this delightful home. Close to locations from all that we love in Hyde Park, 53rd St Commercial Corridor, Butternut Park, University of Chicago, the Lab School, Whole Foods, Trader Joe's, Metra and CTA. This is modern Hyde Park living-elevated.

5312 S Woodlawn Avenue Unit #1, Chicago

$345,000
3 Beds 2 Baths 12377204 MLS CLOSED Status
Step into this beautifully updated and spacious three-bedroom vintage condo, perfectly situated on a quiet, tree-lined street near the University of Chicago. This elegant home blends classic architectural charm with modern updates. Original Craftsman woodwork, French doors, hardwood floors, a decorative fireplace (might be usable), and soaring ceilings have all been lovingly preserved, offering timeless character throughout. The recently renovated eat-in kitchen features 42" cabinetry, ample counter space, and a brand-new LG washer and dryer tucked conveniently nearby. Both bathrooms have been updated. Gracious rooms are located off the central foyer, creating a flowing layout ideal for comfortable living and entertaining. A light-filled sunroom with an extra window connects to both the living area and one of the bedrooms, offering the perfect spot to relax or work from home. Just off the kitchen, a private rear deck provides additional outdoor space. There is a storage unit and secured parking is available on a first-come, first-served basis in the gated lot behind the building, with additional easy street parking in front-no permits needed. *3D Tour and floor plan will be added in shortly*

5143 S Greenwood Avenue Unit #1, Chicago

$1,630,000
3 Beds 4 Baths 12398613 MLS CLOSED Status
Stunningly renovated all-brick residence situated in the desirable Hyde Park area! This home, nestled within the University of Chicago campus neighborhood and in proximity to the esteemed Lab School, has undergone meticulous renovations featuring top-tier finishes, resulting in a modern living environment within this historic locale. The first floor showcases a welcoming open floor plan that allows for abundant sunlight to flow throughout the day. The kitchen is equipped with custom Henrybuilt cabinetry, a spacious island, soapstone countertops, and high-end appliances, including a Miele dishwasher, a SubZero refrigerator with a double drawer freezer and matching custom front cabinets, as well as a Lacanche French double range with a Miele hood. For culinary enthusiasts, the kitchen is further enhanced by a single bowl Elkay sink, a sophisticated reverse osmosis water filtration system, and a whole house filter for lead removal. A conveniently located powder room off the kitchen is perfect for guests. Large windows provide views of the covered deck and the expansive landscaped private backyard. The window treatments feature electric shades, Silhouette Hunter Douglas shades, and custom roll-up screens! Upon reaching the second floor, you are welcomed by a charming skylight at the top of the stairs. This level comprises three spacious bedrooms, two renovated full bathrooms, and conveniently situated laundry facilities near the bedrooms. The master bedroom boasts two generous walk-in closets, while the bathrooms are equipped with waterfall showers featuring custom inset floor drainage. The generous bedrooms are adorned with custom overhead fans and hardwood flooring. Additionally, there is an office/sunroom located above the deck, offering a view of the private tree-lined backyard. The renovated finished basement includes a private bedroom, a full bathroom, and a recreation room with a kitchen/bar area, along with multiple closets. There is also a space that can serve as a workshop or additional storage. Lastly, washer/dryer hookups offer future flexibility. Renovated plumbing, electrical systems, and a three-zone HVAC system guarantee comfort in every area. The backyard provides access to a spacious 2+ car brick garage that offers ample storage. The elegant newer Loewen windows and doors complete the charm of this exquisite home. Featuring high ceilings and custom recessed lighting throughout, this is a chance to acquire a remarkable property in a highly sought-after location.

5528 S Kimbark Avenue, Chicago

$220,000
3 Beds 2 Baths 12396319 MLS CLOSED Status
MULTIPLE OFFERS RECEIVED Classic Hyde Park Corner Condo - Vintage Character Meets Modern Amenity This corner unit in a vintage Hyde Park courtyard building combines character and convenience. Bathed in natural light from windows on three sides, its open-plan living area features beautiful hardwood floors and a kitchen with a stylish snack bar, granite countertops, and stainless-steel appliances. InUnit Laundry, with washer and dryer included, means no common-area hassle. Other features include individual furnace and central air, thermal windows, and fresh paint throughout. Prime Location is just a 10minute walk to the University of Chicago-ideal for students, faculty, and professionals. This building is Investor-Friendly with reasonable association fees, low taxes, and the cash-flow-friendly building make this a savvy investment.

837 E 52Nd Street Unit #3, Chicago

$435,000
4 Beds 2 Baths 12364955 MLS CLOSED Status
***Multiple offers received. Highest and Best Requested by Monday 5/19 at 3pm.*** Hyde Park vintage move-in perfection! Gorgeous, meticulously restored 4bed/2bath home in an A+ location in the heart of the neighborhood! This condo was lovingly restored over the last 25 years with INCREDIBLE ATTENTION TO DETAIL!!! All the beautiful vintage charm was kept while seamlessly integrating modern updates: 4 mini splits for AC, in-unit laundry, gut rehabbed kitchen and baths + new windows on ALL FOUR SIDES. A beautiful foyer with cute built-in boot closet and grand living room space welcome you into the home. High ceilings, refinished hardwood floors and carefully restored millwork throughout. An elegant decorative fireplace with built-in bookcases and bay windows overlooks pretty Dorchester Ave in the living room. Huge separate dining room with box beam ceiling, bay windows, and arched details accommodates a large table. Both baths tastefully renovated in 2020; master bathroom with subway tile, Pottery Barn lighting, shelves, hooks and Kohler fixtures. Truly 4 bedrooms with great closet space in all rooms. The primary bedroom has a walk-in closet. Excellent split-bedroom layout for lots of privacy with a zigzag hallway with large closet. Bedrooms two and three are spacious as well with good light and storage. The small fourth bedroom has its own en-suite bath making it a perfect guest room or home office. Modern white kitchen with new stainless-steel appliances, granite countertops and lots of storage plus a cute two-seat breakfast bar overlooking sunny east-facing deck. Original butler's pantry between kitchen and dining room makes a great bar. Big back deck off kitchen overlooks the fully fenced large backyard and garden. Walking distance to CTA, Metra, U of C and lake! Just around the corner from Philz Coffee, Mesler, Virtue and all the great shops and dining on 53rd Street! Monthly rental parking available nearby!

5225 S Dorchester Avenue Unit #2, Chicago

$239,000
2 Beds 1 Baths 12358265 MLS CLOSED Status
Prepare to fall in love with this top floor vintage 1898 condo, beautifully located just North of the U of C campus and near wonderful shopping and restaurants, parks, the lakefront trail, 57th Street beach, and Metra access. You will love the vintage charms of this unit, including 10 ft tall barrel ceilings, original wood moldings, decorative wood fireplace and a front bay window. The unit has hardwood floors and replacement thermopane windows throughout + updated lighting, ceiling fans, and can lights in just the right combination. The front living area has a living room open to a flex space currently used as a home office, with custom wall-mounted bookshelves. You will find some smart, custom closet systems and a lovely updated kitchen with dark wood cabinetry and granite countertops, stainless appliances, and a coffee bar corner near the back entry. The dining area is open to the kitchen with a breakfast bar, and ample room for two seating areas (very flexible space!) You'll appreciate the stylish and serene bedrooms, the light and bright top floor vibe, amazing storage in the basement, and a huge covered back deck with good views of the fenced shared backyard area. Get ready to enjoy a great Summer in this vibrant Hyde Park neighborhood!

5338 S Greenwood Avenue Unit #3, Chicago

$3,850,000
5 Beds 5 Baths 12355933 MLS CLOSED Status
Welcome to 5626 South Woodlawn Avenue - a gracious and architecturally significant residence nested within the University of Chicago campus in Hyde Park, one of Chicago's most historic and vibrant communities. One of two houses designed in 1911 by the esteemed firm of Riddle & Riddle - this was personal home of architect Herbert Riddle. Crafted with a distinctly French elegance, the remarkable entrance canopy evokes Hector Guimard's iconic Paris Metro stations. Gracefully arched windows and Art Nouveau railings further enrich the home's refined facade. Offering over 6,000 square feet of living space, the layout reflects the influence of European sensibilities on Riddle's work. The Living Room overlooks the garden and provides a tranquil retreat in the French tradition, while the formal Dining Room is positioned at the front of the home in the practice of 18th-century English custom. Now thoroughly renovated, the home seamlessly blends its architectural heritage with modern sophistication. In 2019 the current owners undertook a project that was comprehensive: it included a structural renovation for a new kitchen, new spa-inspired baths, updated lighting, new and refinished hardwood floors, and modern essentials like updated electrical, waterproofed basement, a new boiler, and water filtration system. At the heart of the floor plan, the dramatic, high-end kitchen anchors the home and features top-of-the-line appliances and sophisticated finishes, offering both style and functionality. The kitchen connects seamlessly to the adjacent bar, dining, and entertaining areas - complemented by a gallery, den, and private office. On the upper levels are a lavish Primary Suite that spans the width of the house, four additional bedrooms, a stunning two-story sitting room and a spacious Great Room designed with flexible options for living, working, or recreation. The partially finished lower level allows ample space for a gym, game room, laundry, mechanicals and storage. Set on an oversized lot, 5626 South Woodlawn is a rare opportunity to own an architecturally significant home that unites historic charm with modern sophistication - in the heart of one of Chicago's most beloved neighborhoods.

5626 S Woodlawn Avenue, Chicago

$650,000
4 Beds 2 Baths 12303717 MLS CLOSED Status
5429 Drexel is a handsome, Victorian 4 bedroom, 2 bath SFH located the heart of Hyde Park. It is a classic Chicago Greystone with beautiful original architectural features including oak trim, pocket doors, built-ins, and excellent plaster moldings throughout. The spacious primary bedroom has west facing bay windows, a comfortable seating area and one of two decorative fireplaces. The sunny roof deck (20'x20') above the 2-car garage is private and quiet. The large walk-out basement has the potential to be incorporated into the home or developed into a separate living space with its own front entrance. Great location, a short walk to The University of Chicago and the U of C hospital complex, just steps from Bessie Coleman Park and close to all the amenities that Hyde Park has to offer. Being sold "As Is".

5429 S Drexel Avenue, Chicago

$699,000
4 Beds 2 Baths 12346829 MLS CLOSED Status
Hyde Park 4Bedroom SFH with yard and two car garage parking! Located on a lovely tree lined street, the beautiful greystone residence was built in the Neoclassical design and has many original architectural features alongside updated neutral finishes creating a unique, warm and inviting interior. The living, family and dining room are bright spaces- all with hardwood flooring and 10 foot ceilings. In the dining room, the focal points are the beautifully tiled decorative fireplace and coffered ceiling. The space can easily accommodates a table of 12. Kitchen, mud room plus a half bath complete the floor plan on the main level. Kitchen has custom cabinetry with soft close drawers, all stainless steel appliances, butcher block counter tops and a pot filler plus sufficient space for a sitting area for meals or work. Along the side of the kitchen: a convenient and generous mud room- making arrivals and departures easy and effortless. All of the bedrooms are located on the second floor. The primary faces East and has a lovely bay area. The open concept partially finished basement is spacious with a separate laundry room. Outdoor spaces include a custom deck off the kitchen-with retractable flooring to assist with the delivery of items into the basement, two car garage, yard with areas for plants and a side yard. Recent updates and upgrades to note: freshly painted throughout, tankless water heater, whole house Aquasana water filtration system, R30 insulation in the 2nd floor and a new garage roof. Excellent location within easy walking distance of the University of Chicago and its Hospitals, green spaces, shopping District on 53rd street and 55th. A true Hyde Park gem!

5316 S Drexel Avenue, Chicago

$725,000
4 Beds 3 Baths 12342078 MLS CLOSED Status
5/25 open cancelled, offer accepted. Welcome to 1311 East 55th Street, a Mid-Century "E" Townhouse designed in the 1960s by renowned architects I. M. Pei and Harry Weese. Nestled in the vibrant heart of Hyde Park, this 4-bedroom, 3-bath residence seamlessly blends architectural heritage with sophisticated, modern updates-all within easy walking distance to the lakefront, shopping, transportation, and the University of Chicago. The home was completely gutted and meticulously renovated in 2015, with upgrades including new plumbing stacks, new electric, European-style bathrooms with quartz walls and Grohe fixtures, new stairways, new windows throughout, and essential systems like a new roof, water heater, furnace, and AC. The high-end kitchen features sleek finishes, ample drawer and storage space, an induction range, and top-tier appliances (Liebherr refrigerator, Fisher Paykal oven). Additional highlights include a renovated family room and office, a new utility room with washer and dryer, and refinished hardwood floors throughout. The current owner has carefully restored the home's original mid-century character, honoring the trademark light, efficiency, and comfort of I. M. Pei's design. Buyers will enjoy tree-lined views of Nichols Park and the fountain just across the street, a large, sunny, peaceful patio paved with bluestone, generous storage, and one dedicated parking space. This is a rare opportunity to own an architecturally significant home that offers both modern convenience and timeless design in one of Chicago's most beloved neighborhoods.

1311 E 55Th Street, Chicago

$650,000
3 Beds 3 Baths 12343563 MLS CLOSED Status
Looking for a wonderful move-in ready townhouse? Then look no further, this is it! Entering the main floor the mudroom with closet is roomy enough to welcome your guests and remove unneeded layers. You are greeted by gleaming hardwood floors in rooms flooded with natural light from the huge windows both east and west. The living room space flows into the dining area with access to the delightful kitchen that would inspire anyone to want to cook. There is a powder room conveniently nestled in the corner of the floor with heaps of closet storage as well. Upstairs are 3 nice-sized bedrooms with ample storage that are drenched in natural light from newer windows and a stairwell skylight. There are also 2 full baths, one a primary. The partially finished basement has a large room for any purpose you desire and a large separate laundry then the utilities in another space. This house is a must see.

5205 S Kimbark Avenue, Chicago

$277,000
2 Beds 1 Baths 12336030 MLS CLOSED Status
Welcome to your Hyde Park haven-tucked on a tree-lined street in a timeless brick mid-rise, where classic architecture meets modern luxury just steps from the University of Chicago and the Lab schools. This beautifully renovated 2-bedroom, 1-bath co-op offers high-end finishes, everyday comfort, and an unbeatable location in one of Chicago's most beloved neighborhoods. Enter through a gracious formal foyer that leads to a generous living room, seamlessly connected to an elegant dining room with hardwood floors, custom built-ins, and crown molding throughout. The chef's kitchen is thoughtfully updated with a Sub-Zero refrigerator, professional-grade Frigidaire range and hood, Bosch dishwasher, quartz countertops, and a spacious pantry. Both bedrooms are privately situated on the opposite side of the home, offering a peaceful retreat. Additional features include central SpacePak air conditioning, an in-unit ASKO washer/dryer, an updated bathroom, and a large dedicated storage room in the basement. Enjoy the best of Hyde Park living-just moments from the University of Chicago campus, the vibrant 53rd Street corridor, parks, and the lakefront.

1421 E 58Th Street Unit #2E, Chicago

$355,000
4 Beds 2 Baths 12338565 MLS CLOSED Status
This gracious four-bedroom condominium was originally crafted for discerning Kenwood residents seeking the grandeur of a single-family home, without the cares of home maintenance. Perfectly situated overlooking picturesque Drexel Square and the oldest public fountain in the city, this spacious, light-filled unit is awaiting the care of its next owner. While priced to reflect the need for thoughtful upgrading, the home retains historic details - barrel vaulted ceiling, custom built-ins, rich hardwood floors and decorative pilasters - it's a stunning canvas for your personal vision. This unit also offers an over-sized workspace for your hobbies along with ample storage. An amazing opportunity to create a bespoke residence, just moments from the facilities of the University of Chicago, the lakefront and all the amenities of Hyde Park.

843 E Drexel Square Unit #1, Chicago



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