View All Oak Park IL Oversized Lot Homes Listings

$1,360,000
4 Beds 5 Baths 12637815 MLS CLOSED Status
*SOLD IN THE PRIVATE LISTING NETWORK BEFORE PROCESSING* Welcome to one of Oak Park's most extraordinary homes which features a stunning, unique, and spacious residence nestled among the tree lined streets of the legendary Frank Lloyd Wright Historic District, where architectural history frames every view and every moment feels elevated. Built in the 1990s with solid newer construction and modern-day conveniences, this exceptional home offers over 4,700 square feet of beautifully designed, light filled living space plus a full finished basement, all set on a spectacular private 0.1974 acre fenced lot in a premium location. From the oversized paver driveway and rare attached 2 car garage to the gorgeous brick patio and breathtaking backyard oasis, every inch of this home has been thoughtfully designed for both grand entertaining and everyday living. Strategically placed custom built-ins throughout the home add an exceptional level of luxury and elegance, elevating every room with purposeful beauty and refined craftsmanship. The spectacular chef's kitchen features a grand center island and sunlit eating area that flows seamlessly into an enormous family room complete with a wood burning fireplace which opens directly onto the paver patio and sweeping private backyard. The home boasts three wood burning fireplaces, including one in the stunning private library that is part of the incredible owner's suite which also features a 30-foot balcony overlooking the lush backyard below. All 4 bedrooms on the second level are exceptionally spacious with shockingly large walk-in closets, and the versatile third floor offers additional living space that can easily be enclosed as a 5th bedroom, with a half bath that is fully plumbed and ready for a conversion to a full bathroom. The full basement extends your living further with a dedicated exercise room and ample storage space. With easy access to downtown Oak Park, top rated schools, shopping, restaurants, and parks, and just 20 minutes from Downtown Chicago, this is truly a once in a lifetime opportunity to set a new standard of living in one of the most architecturally celebrated neighborhoods.

632 Fair Oaks Avenue, Oak Park

$855,000
5 Beds 4 Baths 12608182 MLS CLOSED Status
Get ready to be wowed by this surprisingly spacious, sundrenched, mid-century stunner in the perfect, heart-of-Oak Park location! This must-see, unique, tri-level home built in 1971 offers loads of space and options for the best of modern living on a tranquil, picturesque street with grand homes. Through the side entrance, be welcomed into the foyer and appreciate the gleaming hardwood floors, tall ceilings, and large, bright windows that flood the home with light. Gather with loved ones in the vast living room, spacious enough for multiple conversation areas for entertaining, or perfect for cozy nights in. And easily host your largest holiday gatherings in the adjacent dining room with two walls of windows for year-round sunlight! Cooking your gourmet meals or everyday snacks is a delight in the bright, clean, kitchen with all new stainless steel appliances ('26), including an induction stove; miles of new countertops ('26); new floors ('26); new heating ('26); quality, spruced-up cabinetry, with plenty of space to add an eat-in table or island for extra prep space. A convenient powder room and coat closet complete this level. Head up a short flight of stairs to find three fantastic, bright bedrooms, all with great closets and an oversized hallway bath with a stylish new double vanity and updated fixtures. And we're only getting started with the space! A few stairs down from the first floor, you'll find an absolutely gigantic sunken family room with bright, tall windows and tons of space - perfect for a play area, hosting family game nights, movie nights or for watching the big game with friends. Through this room and up a few stairs at the back of the home is an incredibly spacious private primary wing! It showcases an enormous great room with large windows and a stylish full bath, with a large sitting room and bedroom. The sitting room boasts huge, south-facing windows, and leads to the bedroom, which easily fits a king-sized bed and overlooks the serene backyard - your perfect oasis wing. But wait, there's more! From the lower level sunken family room, a private side hallway leads to a bedroom with a convenient full bath, and a few more stairs down from this level is yet another massive rec room with new luxury vinyl plank ('25) that leads to a spacious laundry room/kitchenette with new laundry ('26); new kitchenette with new cabinets ('26) for even more space and options. Al-fresco, the generous space continues with a backyard boasting a lovely brick-paver patio for your warm-weather entertaining and dining and a two-car garage with adjacent additional parking for two cars. This 4,500 plus sq feet home, with three private entrances, has plenty of intergenerational living and income-generating options (and with the rear wing sitting room already plumbed, easily add a kitchenette, laundry, or even a wet bar to this wing) to effortlessly make it work for your needs - a business, in-laws, nanny, teen, guests or Airbnb - and house hack your way into being a Real Estate Mogul! So much has been done in this home in 2025-2026 - fresh paint throughout; new appliances throughout; most light fixtures updated; updated floorplan; new flooring, new heating and new plumbing in some parts of the home; and so much more. This almost-ground-level, deceptively large, move-in ready home can easily adapt as your needs evolve and is in a premium location in Oak Park with friendly neighbors - just moments from all this lovely village offers - schools, cafes, shopping, dining, library, movies, pool, parks, dog park, the farmers' market, public transportation, and so much more - all at your fingertips. This updated gem with options galore is the one you've been waiting for--welcome home!

141 Wesley Avenue, Oak Park

$1,280,000
5 Beds 4 Baths 12429781 MLS CLOSED Status
Welcome home to this stately brick home on Kenilworth in NW Oak Park's coveted boulevard neighborhood. Situated among Oak Park's classic and architecturally lovely homes, 1118 N Kenilworth is spacious and stunning while also warm, sprawling, and inviting. The wonderful flow is conducive to comfortable living and gracious entertaining. Enter the home via the magnificent rounded front door and enjoy the fabulous foyer and gorgeous original staircase. You are greeted by the first floor's oversized formal living room and dining room spaces, and its massive bright, kitchen open to the light-filled family room with huge windows overlooking the back yard flowing out into the extra-wide deck and mature, professionally maintained gardens and yard complete with in-ground sprinkler system. Private home office/playroom, 3 season room, mudroom, and powder room complete the fantastic first-floor plan. Upstairs are five huge bedrooms (one being used as an office) and two full bathrooms surrounding the home's original staircase, all with a blend of original features and attractive updates. Finished basement offers a large recreation room with fireplace, full bathroom, separate laundry and crafts room, another home office or workout room, and generous storage. Beautiful hardwood floors through the home, newer windows and skylights, custom kitchen cabinetry w/island, Bosch and KitchenAid stainless steel appliances, extensive silestone countertop space, pantry, and banquette for casual dining. Maintenance-free exterior deck and tile roofing on home. Newer boiler and AC plus sewer back-up installed in the yard. Large brick garage w/floor drain has insulated overhead door and additional parking pad next to garage. Huge attic space could easily be converted to so much extra living space! This glorious home is a "must see"!

1118 N Kenilworth Avenue, Oak Park

$735,000
3 Beds 3 Baths 12345039 MLS CLOSED Status
Oak Park Frank Lloyd Wright Historic Neighborhood! Are you ready to fall in love? From the stucco & stone exterior to the throwback character, this 1917 charmer exudes class throughout. How many homes can take you back in time while simultaneously feeling right now? Rambling hardwood rolls almost everywhere you walk. Old school woodwork frames your living spaces like you're living in art. A lovely mix of chrome and gold-brushed finishes and a pristine palate of color heightens the experience. Enjoy working in the upgraded kitchen, with built-in peninsula eating area, high-end stove, hardtops & 42-inch cabinets. Snuggle up in the living room in front of your wood-burning fireplace as you gaze out on timeless homes through your bay window. Tuck away in the back den, overlooking your 6-foot cedar fence-wrapped backyard. Entertain like never before with your oversized dining room, tying all rooms of the first floor together. Head upstairs to three generous bedrooms with plenty of closet space. The primary bedroom with en suite boasts extended room that can be converted into an office or changing area. You have options. Light reverberates throughout. Built-ins pop out of nowhere for all the trappings. A rec room in the basement is ready for work or play. Find the extra storage room in back. Outside, the deck stairs carry you down to the rounded paver patio. Plenty of room to run on green space that connects to the fenced-in, raised-bed garden -- what would you like? Perennial asparagus, grapes and berries should be peaking through soon, you know. Quick access to the 2-car garage which backs to the alley. Enjoy beautiful Oak Park with schools and parks just down the street and around the corner. Short commute to Chicago & public transport in all directions, make this amazing property your home today!

818 N Euclid Avenue, Oak Park

$399,000
3 Beds 2 Baths 12093240 MLS CLOSED Status
Nicely updated 3 bedroom/1.1 bath American 4-square with all of the charm that Oak Park homes have to offer: Hardwood floors, lovely art glass, crown molding, original baseboards, and architecturally pleasing arched walls. Leave your coats, shoes, and weather in the enclosed front mudroom and enter the warmth of the light- filled living room. The generous dining room opens to both the kitchen and bonus room at the back of the home complete with oversized windows overlooking the garden/yard bringing light from both ends of the home into your living space. Once an enclosed back porch, this room is very versatile, having been used as a home office, playroom, and family room. The conveniently located kitchen has great cabinet space and stainless steel appliances. The second floor boasts 3 generous bedrooms and a full bath, as well as a tandem room which offers more flexibility depending on your needs- nice home office overlooking the back yard, play space, sitting room, or a huge walk-in closet! The basement is high and dry and recently painted to entice your creative mind with ideas. Washer and dryer and mechanicals are conveniently located in one area so that should you choose to finish the basement, you can have a large space with which to work. Newer features to make this home move-in-ready include freshly painted entire interior (2024), many new windows (various dates), updated baths (2024), new flooring in family room (2024), Exterior stucco (2018), new back steps (2024) and new sewer line (2022). Cement work in front has been scheduled for completion. Central AC. 2 car garage. All of this close to el, schools, parks, shops and restaurants.

1179 S Harvey Avenue, Oak Park

$850,000
3 Beds 3 Baths 11875980 MLS CLOSED Status
Oak Park's special and most anticipated residential offering! Built in 2018. The District House Condominium, The Ranquist Development Group's high-end, modern and upscale project is the iconic gateway to Lake Street and a new Oak Park landmark. Featuring "artful urban residences" with a striking exterior showcasing floor to ceiling glass with strong 4' wide cantilevered solar shades to provide shade for the windows recalling the Prairie School's horizontality on the expansive glass facade. A " GOLD LEED CERTIFIED" building with incredibly handsome building concept and design! An architectural jewel! This breathtaking unit in the highly sought after "02" tier is 2,056 sq. ft, making it one of the largest floorplans in the development and includes 3 bedrooms, 2.5 Baths, an Office, private outdoor space and 2 indoor heated parking places. This contemporary condo has soaring 10' ceilings ceilings and magnificent light and panoramic views through two massive exposures, of wrap around, floor-to-ceiling glass windows overlooking the green space and beautiful homes on the residential Euclid Ave., and the exciting urban vibe of Lake Street. Designer selected finishes in the unit include wide plank Oak Flooring, paint color selections, remarkable eye catching modern light fixtures, a real chef's kitchen and entertaining space incudes custom 42" Italian flat panel cabinetry by Archisesto, gleaming quartz counters, an exceptionally wide island counter, and a beautiful backsplash tile. A large and sumptuous Primary suite with an elegant master bath including a sleek and attractive double sink vanity and beautiful walk-in shower and finally and an oversized walk-in closet with custom shelving and organization. The District House is a walkers paradise with a rating of 99/100, in the center of the Hemingway Historic District, residents can walk just steps outside their door to some of Oak Park's best restaurants, such as Maya del Sol, Il Vicolo, Rustico, The Amerikas, Starbuck's, The Courageous Bakery, Cucina Paradisio, Hemingway's Bistro and Citrine, as well as the neighborhood parks, library and schools. Fairgrounds Cafe and The Pilates Studio are located on the 1st Floor of The District House. Residents of The District House also share an expansive roof-top deck with plenty of space to relax and enjoy the Chicago Skyline and sunsets. A community gas grill and community room including refrigerator, microwave, cabinets and counter with sink make dining and entertaining a breeze. The outdoor deck and Eco Green Roof System include lovely wild flowers, native plants and prairie grasses. An easy commute, only a block away from the CTA's Green Line for easy access to and from downtown Chicago. This particular unit enjoys some of the best views available in the building. The exciting contemporary design of The District House and this unit is truly exceptional.

147 N Euclid Avenue Unit #202, Oak Park

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Oak Park, IL · Curated MLS Search

Oversized Lot Homes in Oak Park, IL

An editorially curated view of every active oversized lot homes listing in Oak Park, IL. Updated in real time from the local MLS, presented without the noise.

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