View All Oakland Chicago IL Greystone Homes Listings

$2,150,000
12673900 MLS NEW Status
Once in a Generation, The Crown Jewel of Oakland set on a botanical campus spanning 70 feet of frontage. If you seek the best, if you have exquisite taste, if you want a one of a kind with an elevator that opens directly into most apartments with grand terraces, you have arrived. Located in an exclusive community alongside million dollar homes & within 1/4 block of Mandrake Park, 5 minute walk to the lakefront at the very north end of Drexel Blvd, with its idyllic fountain & cul-de-sac is a magical whimsical storybook setting offering 5 Massive full-floor units ultra-luxurious 3-4 Bed/2-3 Bath residences set in a made for TV boutique, elegant, Gothic Greystone. Be inspired by the grand, formal lobby with inlaid stone floors, intricate woodwork, stunning modern art, a crystal cut chandelier & super "mod" LED wall sconces. The elevator opens directly into most residences' private foyer, which leads to a massive great room, with soaring ceilings & 7' tall window bays that capture phenomenal sun soaked south & west vistas up & down lush & forested Drexel Boulevard. Gorgeous plank hardwood floors, which contrast with sleek 7" crown & baseboard moldings, 8' tall solid core doors, polished chrome door handles & accessories, a custom designed & built fireplace with glass, stone & quartz mantel + gorgeous lighting with Decora switches & dimmers. Adjacent to the great room, cook, entertain & eat in a true & REAL gourmet kitchen with 1 1/4" thick quartz countertops, a massive work island with bar stool seating, state-of-the-art stainless appliances, a multi burner stove, tunnel exhaust hood, dishwasher, 36" refrigerator with ice & water dispensers, built-in microwave drawer & brilliant porcelain full height backsplashes. Other features include strategically placed cable & electric for flat screen televisions, Hi Efficiency HVAC, high tech LED lighting & many other features. Gracious jaw dropping primary bedroom suite with an infusion of natural light from tall south facing windows, enormous walk-in closet is ready to house a large wardrobe, with custom double hanging SS organizers some which include 20 lineal feet of hanging & 55 lineal feet of shelves. Resort Luxury spa bathroom with heated porcelain tile heated floors, steam shower, quartz bench, a custom designed floor to ceiling glass wall & door system, a rain shower, handheld shower & separate body washes, 6' air bath, a wall mounted floating double bowl vanity & two large mirrored medicine cabinets. Numerous oversized rear terraces offer respite to enjoy cocktails, read a book or have breakfast through dinner, private & spacious with sweeping downtown views. Full Laundry Center complete with full size washer & dryer, countertops & cabinetry cabinets. Enjoy fully curated exotic botanical gardens fully with specimen trees & bushes, many grafted, from around the world, including Japan, various countries in Eastern Europe, Canada & the USA ( all irrigated controlled by app) topped off with 9 car garage (2 of 9 Tandem). Fully stabilized with exceptional longer term tenants, this stunning, unique, trophy property offers a rare hybrid opportunity pairing investment with legacy. Full financials, floorplans, survey, and extensive pictures available. Actual Annual Income $213,045/NOI $141,525 / 6.5CAP Pre Approved buyers only. 48-72 hours' notice to show M-F (no weekend showings)

3967 S Drexel Boulevard, Chicago

$435,000
3 Beds 3 Baths 12574056 MLS CLOSED Status
Beautiful Bronzeville newer build, solid brick construction, with features you will not find anywhere else on the market!! Top floor Penthouse. Supreme Location conveniently right off Oakwood Blvd and Lakeshore Drive, almost a corner, surrounded by city parks and land, guaranteeing your views will always be magical! Ellis is a street flooded with period brick homes, greystone builds, & architecture they just don't re create these days. If you're looking for a combination of Chicago Classic architecture, with a modern design & layout, & Chicago City Skyline views from every window & terraces, here it is! Stunning Views on the top floor with East, West and North Exposures! Sunrise and sunset with a backdrop that feels surreal. This unit shows 11+ feet high ceilings, light filled with oversized windows, and sliding window doors at both the front and back terraces of the home. The Expansive great room, has a brick feature wall and a fireplace to set the tone for cozy nights at home. Private front brick terrace overlooks Mandrake Park athletic field+ beautiful Ellis Ave @14'x7'. East terrace is located just off the primary suite and is 11'x14'. There's a separate patio gate access from the back door in addition to the primary suite access! As you enter the condo you're greeted with a large foyer, open concept living, dining and kitchen with a stately hallway, perfect to use as a gallery and display all of your artwork + photographs. Stacked newer Laundry located just off the hall. First owners of this unit! Pride of ownership & it shows! This unique condo has just been repainted and had a full unit natural Hardwood floors refinished to perfection. 3 generous sized bedrooms with soaring ceilings and fan lights. Primary suite shows a walk in closet with custom organizers & drawers, marble tiled bathroom, with a double sink, soaking tub & separate shower. Wake up with your coffee and enjoy Every room has a city skyline view!! Plus current Seasonal Lake Views of Lake Michigan. Shows you just how near that run or bike ride you are. Landmarks nearby include Oakwood beach, 41st street bridge, Burnham Harbor & Park, 31st street Beach, Blackstone Chicago Public Library, and nearby Bronzeville dog park! Easy access to i90 and nearby Northwestern Medical. Ellis court includes a Gated parking space, gated front call system with security surveillance accessible to residents, a storage in the lower basement with a large private bike storage for residents. One year transferable home warranty included. Local nearby favorites just a few minutes drive include Mariano's, Norman's Bistro, Chicago's Chicken and Waffles, Little Sandwich House, LA Fitness, and Shawn Michelle's homemade ice cream to name a few! LOW HOA fees will remain for the foreseeable future as the HOA rents the roof to T mobile and this lease was just resigned! Cutting your fees in half! Exterior of the building past improvements include Roof tear off in 2018, rear stairs and front deck have been redone with paint and new deck boards in the past years.

3945 S Ellis Avenue Unit #3N, Chicago

$947,000
6 Beds 5 Baths 12471948 MLS CLOSED Status
Where timeless architecture meets modern ease, this exquisitely renovated greystone offers room to live, entertain, and unwind in style. With six bedrooms, four-and-a-half baths, and a thoughtful three-level layout, every corner invites you to stay a little longer. On the main floor, natural light flows through gracious living and dining spaces, anchored by a designer kitchen and a dining room crowned with a striking fluted light fixture-an art piece in its own right. Wide doorways lead to a rear deck that's perfect for summer dinners or a quiet morning coffee. The second floor is a sanctuary. The primary suite features customized closets and a charming step-up window niche that begs for a built-in seat or meditation perch. An additional ensuite bedroom shares the level, while a private balcony off another bedroom offers a quiet retreat in the treetops. Up on the third floor, the home takes a playful turn: a dedicated Snack Lounge-complete with mini fridge, microwave, and cabinetry-sits among three more bedrooms, ideal for late-night treats or weekend movie marathons. A fully finished lower level provides a guest bedroom, flexible exercise or hobby space, and a convenient exterior entrance. Three separate furnaces deliver zoned heating and cooling for comfort on every floor. Outside, a classic one-car brick garage completes the picture. Set on a serene, short street just blocks from the lake and the pedestrian bridge, this home blends elegance and everyday function. From the statement lighting to the inviting outdoor spaces, 922 E 42nd Place is designed for the way you live-and the way you love to entertain.

922 E 42Nd Place, Chicago

$725,000
4 Beds 4 Baths 12222630 MLS CLOSED Status
Stately Vintage 3 story Greystone. Current owner a long time Chicago architect has loving restored the home maintaining much of the original charm and character. The home features a sprawling open floor plan full of character at every turn. Patterned mahogany wainscoting wrap 3 stunning levels of stairs, intricate ornamental plaster ceiling inlays, turret rooms, 7 fireplaces, and a turn of the century entry & foyer that will transport you to the golden age of the Chicago Greystone. What a beautiful home! Main level features large updated kitchen adjacent to dining room and set at the rear of the home so perfect for outdoor entertaining. An open parlor connects the dining room to the enormous living room and eventually to the formal entry. The second floor features a large primary suite complete with turret room, enormous walk in closet, and separate water closet/shower & makeup station/sink. Two additional bedrooms with large walk-in closets, a full hall bath, and gracious open space atop the stairs complete the floor. The third floor contains a large open recreation room with lake views! Also additional bedroom and multiple storage/walk-in closets that would be ideal for work from home space. Lower level is partially finished with large open room, kitchenette, potential bedroom, and storage abound but does need some attention for proper use. Substantial work has been done to the home over the past 10 years including but not limited to... entirely new roof including structural elements; newer electrical & plumbing; various windows replaced or repaired; new sewer and water supplies; addition of zoned HVAC systems & new hot water heater; refinished wood, doors, and trim; various tuck pointing & chimney work; and the list goes on. Massive 20 x 40 garage with an open lofted room above. Above grade square footage estimated at 3300sf but total square footage is over 5000sf including basement & garage loft. Superb Bronzeville/Oakland location with new construction in every direction. Close to IIT, UIC, University of Chicago, lake front & trail, 15 minutes to the loop, 8 minutes to Hyde Park, and close to so much more. A rare find in a city of extraordinary homes! Any questions regarding this listing please contact Norbert Mika - Text or email preferred.

3982 S Lake Park Avenue, Chicago

$550,000
7 Beds 4 Baths 11993102 MLS CLOSED Status
In the heart of the storied Oakland community, nestled proudly overlooking the Boulevard, stands a majestic relic of the past, awaiting its renaissance. The ME Team brings you an exclusive insight into the magnificent Greystone at 4123 S Drexel Avenue, an architectural masterpiece waiting to be reborn. This three-unit Greystone, a testament to the grandeur of yesteryears, beckons investors, dreamers, and visionaries alike. With its stately gray stone facade casting an imposing silhouette against the skyline, this property is a timeless symbol of elegance and potential. What sets this property apart is not just its historical significance, but the myriad of opportunities it presents. In need of total rehabilitation, this blank canvas offers the chance to transform and revitalize, breathing new life into its 5260 square feet of living space. With four majestic fireplaces lending an air of opulence, and the possibility to duplex down, the potential for grandeur is limitless. Imagine the opportunity to offset your mortgage with the rental income from the other two units, or to craft a singular haven, a sprawling single-family mansion befitting of royalty. The choice is yours, limited only by the bounds of your imagination. Venturing below, discover an additional unit awaiting transformation in the lower level, offering even more potential for expansion or rental income. And with the property boasting both forced air and a boiler system, modern amenities can seamlessly meld with the historic charm, ensuring comfort and efficiency for generations to come. But perhaps the most compelling aspect of this property lies not just in its bricks and mortar, but in its enviable location. Oakland, a community steeped in history and culture, offers more than just a place to live - it offers the promise of generational wealth. In the equation of Location + Land, the sum is far greater than its parts, promising a legacy that transcends time.

4123 S Drexel Boulevard, Chicago

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Oakland, Chicago IL · Curated MLS Search

Greystone Homes in Oakland, Chicago IL

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

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