View All Kenwood Chicago IL Homes with Wine Cellar Listings

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

$2,050,000

5 Beds ⋅ 6 Baths ⋅ 12541443 MLS ⋅ CLOSED Status

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

4730 S Greenwood Avenue, Chicago

$1,600,000

9 Beds ⋅ 6 Baths ⋅ 12100303 MLS ⋅ CLOSED Status

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

4832 S Ellis Avenue, Chicago

$2,280,000

7 Beds ⋅ 7 Baths ⋅ 12005667 MLS ⋅ CLOSED Status

Welcome to 4857 S Kimbark - a spacious stone and red slate house in a desirable South Kenwood location. This home has completely updated mechanicals and wiring, and offers all the modern amenities you expect, yet it retains a wealth of original details such as a stately wrap around porch, inviting wood paneled foyer, carved mantel pieces, built in cabinets and pocket doors in Birdseye maple, cherry and quartersawn oak. Step through the front door into a grand entry foyer with original staircase, wainscoting, fireplace and inlaid floors. Perfect for entertaining and large gatherings, this level offers several rooms and open spaces that can accommodate more or less formal living. New eat-in kitchen with white custom cabinets, quartz counter tops and Miele, Bosch and Thermidor appliances. There is also a sizeable pantry and a powder room on this level. Ascend the stairs to the second floor where you will find 4 very spacious bedrooms with custom built in closet interiors and high-end blinds and shades. There are three bathrooms on this level, two are ensuite. Primary bath has separate steam shower and a laundry room conveniently adjacent. There is a balcony which has just been completely rebuilt. On the third floor there are three additional bedrooms, two bathrooms, large storage closets and a family room with built in entertainment center, speakers, gas fireplace and wet bar with beverage fridge. The basement is finished and features an additional bedroom/ workout or office space, a full bathroom, storage, family/ entertainment room and a wine cellar with cork walls and built in wine racks and wine fridge. The house has 400 amp electric service, all new wiring, smart home wiring, three zone heating and two zone cooling systems, all new copper plumbing, new gas lines, new water service and drains. The inlaid gutters have been rebuilt and the house was fitted with insulation and new red slates in 2007. All 6 bathrooms have been recently remodeled and most feature designer tile, heated floors and Toto, Grohe, Kohler and Kallista fixtures. The gardens are custom designed and are automatically irrigated. The outdoor kitchen with piped gas grill and wood burning pizza oven sits in a peaceful corner of the garden. Thousands of bulbs await spring. There is a wrought iron electric side gate that allows two cars to park on the property. A car port could likely be fitted under the back porch to create more parking, however there is ample street parking. South Kenwood is a historic landmark neighborhood, and the home is designated under the preservation easement with landmarks. Welcome!

4857 S Kimbark Avenue, Chicago

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Homes with Wine Cellar in Kenwood, Chicago IL

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