View All Oak Park IL Estate Homes Listings

$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

$2,325,000
7 Beds 6 Baths 12631834 MLS CLOSED Status
A meticulously restored 1912 Tudor designed by renowned architect Charles White, this Oak Park estate is a masterpiece of historic charm and modern luxury. Nestled on an oversized lot in the prestigious estate section, the home boasts exquisite craftsmanship and thoughtful updates throughout. The grand entryway features custom millwork and wood-paneled walls, leading to a stunning foyer and staircase. The main level offers a living room adorned with diamond-pane windows and a limestone fireplace, a formal dining room, and a sunroom with updated heating and air conditioning. The newly remodeled kitchen features radiant-heated floors, an induction cooktop, two dishwashers, and sleek soft-close cabinetry. The breakfast room with wood paneling and an original bookcase, as well as a mudroom and a butler's pantry, add to the home's charm and convenience. The second level houses three bedrooms, including a reimagined primary suite with a spa-like bath, dressing room, and laundry. There is a cozy den with custom shelving, a mini refrigerator, and French doors. The home offers multiple sunrooms and laundry facilities on all three levels, ensuring ample space and comfort for modern living. The outdoor space is equally impressive, featuring a sprawling lawn, a patio with a pergola and grilling area, a sport/pickleball court, and new manicured landscaping enclosed by new wrought-iron fencing. A three-car garage with an additional lift and a circular driveway provides convenience and style. Additional highlights include a generator, surveillance system, sump pump, audio system, sprinkler system, three-zone central A/C, regularly maintained roofing, and a newly painted treated wood exterior. This impeccably maintained home offers an unparalleled lifestyle in the heart of Oak Park.

420 N Euclid Avenue, Oak Park

$1,725,000
4 Beds 5 Baths 12375199 MLS CLOSED Status
Featured in the 2023 Frank Lloyd Wright Plus Housewalk, this much admired 5-bedroom, 3.5-bath residence is a rare opportunity to own a piece of Oak Park's rich architectural history. Designed by noted architect James Cady in 1909 for prominent banker and bond financier Edward Cornelius Cronwall, this stately home sits on a beautifully landscaped half-acre lot in Oak Park's prestigious estate section. Set behind wrought iron fencing and surrounded by an English-style garden, the home's curb appeal is as striking as its interior elegance. A grand marble- floored foyer welcomes you into an expansive, light-filled living and dining area designed for entertaining-featuring a coffered ceiling, recessed lighting, marble fireplace, and a charming window seat with garden views. This impressive space can comfortably accommodate a large gathering. The chef's kitchen is a true showstopper, boasting a 10-foot quartz island, top-tier appliances, and thoughtfully designed eating and office areas-ideal for both daily living and hosting gatherings. A richly paneled mahogany library offers floor-to-ceiling bookcases, a marble fireplace, and stunning beveled-glass pocket doors. French doors from the sunroom open onto a serene side terrace. Throughout the home, you'll find exquisite details-from hand-painted wallpaper along the extra-wide staircase to original architectural elements that reflect the craftsmanship of a bygone era. The luxurious primary suite includes a marble gas fireplace, walk-in closet, and ensuite bath. The third floor adds versatility with a full bath, second kitchen, laundry, and a spacious recreation or family room. Outdoors, the red brick patio, clay tile roof, and copper gutters blend seamlessly with the home's historic charm. The heated and air-conditioned two-car garage includes a fully outfitted coach house apartment, perfect for guests, extended family, or potential rental income. A sprinkler system and lush plantings ensure the grounds remain a private oasis. This is a rare chance to own an architecturally significant home, meticulously maintained and thoughtfully updated for modern living, in one of Oak Park's most di

539 N East Avenue, Oak Park

$1,060,000
5 Beds 5 Baths 12326487 MLS CLOSED Status
*** Highest & Best Offers Due by 7pm 4/13/2025*** This stunning red-brick Colonial Revival is right in the heart of Oak Park's estate section. You'll love the pristine oak floors, unique architectural details, and those big, bright windows that let in tons of light. As you step in, the grand entry foyer welcomes you and flows seamlessly into the spacious formal living room. There's plenty of room for conversation areas, plus a stately fireplace and built-in surround that really adds character. Oh, and don't forget to check out the lovely solarium! When it's time to entertain, the formal dining room is perfect for hosting holiday gatherings. The kitchen can handle your finest cuisine, with loads of counter space, custom lighting, and stainless appliances. There's even a small mudroom that leads to the two-car attached garage, which is a rare find in Oak Park! Head up a half flight of stairs to discover the home's office, featuring three walls of windows that let in plenty of natural light. On the second floor, you'll find four large bedrooms and three full baths, including a spacious primary bedroom with an en suite bath, a cozy guest bedroom with its own bath, and a newer, large main bath. The charming fifth bedroom is tucked away on the third floor. After a long day, unwind in the beautifully finished lower-level family/rec area. This space comes with a built-in wet bar, custom cabinetry, and a beverage fridge, plus another large full bath and a room that would make a fantastic second office. Step outside to enjoy the park-like lush backyard, which features a built-in sport court and a patio area ideal for entertaining. You can easily walk to everything great about Oak Park-excellent schools, the Farmer's Market, all forms of transportation, delicious dining, quaint shops, and so much more!

646 N Euclid Avenue, Oak Park

$1,520,000
5 Beds 4 Baths 12301620 MLS CLOSED Status
Nestled in the heart of Oak Park's prestigious Frank Lloyd Wright Historic District, this extraordinary residence offers a rare blend of architectural elegance, modern luxury, and an estate-sized lot that is truly one of a kind. Boasting 5 bedrooms and 4 baths, this meticulously maintained home is designed for both grand entertaining and comfortable living. A first-floor dual office provides versatility, while the chef's kitchen, outfitted with top-of-the-line Thermador appliances, is a dream for culinary enthusiasts. No detail has been overlooked in this exceptional reimagined home, featuring custom cabinetry, coffered ceilings, Brussel block driveway, a 50-year architectural shingle roof, updated windows, and a state-of-the-art Control4 audio system. The third-floor theatre room provides the ultimate cinematic experience, while a music room/office above the garage offers a peaceful retreat. Step outside to your private resort-like backyard, where a custom pool, spa, fire pit, and expansive deck create the perfect setting for relaxation and entertaining. Designed by Hulen Landscaping, the grounds are a masterpiece, complete with professional landscaping, exterior lighting, and a full irrigation system. This is more than just a home, it's a statement of timeless elegance and modern sophistication in one of Oak Park's most sought-after locations. A short walk to both the Metra and the Green Line, across the street from the park, and steps from restaurants and the Lake Theater. Don't miss the opportunity to own a piece of history with all the luxuries of today.

216 Forest Avenue, Oak Park

$1,100,000
5 Beds 4 Baths 12271766 MLS CLOSED Status
Check out this amazing Craftsman masterpiece right in the heart of central Oak Park's estate section. It's solid brick construction with beautiful quarter-sawn oak floors, tons of natural light, and lovely architectural details throughout grace this space. Built in 1923 by architect Roy J. Hotchkiss (who was the chief designer for E.E. Roberts), the Jacob Ecker House is truly spectacular and unique. As you walk in, the large double-doored entry foyer and receiving room welcome you, leading straight into the grand living room. It features a stunning original tiled fireplace and plenty of space for multiple conversation areas. The spacious dining room is just waiting for your favorite celebrations, and don't forget about the large screened front porch-perfect for entertaining on those lovely fair-weather days. The chef's kitchen is a dream, equipped for your finest meals with custom maple cabinetry, stainless appliances, soft cork floors, and even room for a breakfast table! One standout feature of this home is the first-floor primary suite, which includes a spacious bedroom, a newer heated sunporch, a cozy sitting room or office, custom closets, and a gorgeous primary suite bathroom. You'll also find another bedroom or office on this level, along with a newer full hall bath. Head up to the second floor to discover three large bedrooms adorned with beautiful trim work and oak floors, plus a nice foyer area for reading and another exquisite full bath. The lower level (more than 2900 sq.ft. in itself!) offers a huge soundproofed movie room, a game room complete with a pool table, a large laundry room, and plenty of storage. You'll appreciate the one-car attached garage and the space for up to three additional parking spots. The 70'x165' lot provides a lush, expansive yard and garden. The location couldn't be better-step out your front door and within minutes find fantastic dining, charming shops, great schools, the Farmer's Market, all forms of transportation and so much more!

219 Linden Avenue, Oak Park

$1,869,500
6 Beds 7 Baths 12008347 MLS CLOSED Status
Rare offering of an extraordinary home! The James Fletcher Skinner House, the crowning architectural design of Charles E White, has the stature of being one of the finest homes in the western suburbs. Recognized as one of the First Significant Structures in the Prairie School National Register, the home's stately corner setting is in the heart of Oak Park's Historic Estate District. A masterpiece of the prairie school era, the home is impressive in scale and offers the ultimate in livability with its timeless design that seamlessly transitions to the lifestyle trends of today. Upon entry, the grand foyer captivates with its exquisite woodwork, leaded glass doors, and an inlaid glass-tiled fireplace. An entertainers dream, the first level offers warm and inviting spaces, including an elegant dining room with quarter-sawn oak paneling and a generous living room featuring a gas fireplace that serves as a focal point with its ornately carved mantel and stained glass windows, giving a touch of elegance and timeless sophistication to the room. The chef's kitchen is a culinary delight, anchored by a custom island with generous storage and wine refrigerator, perfect for both functionality and style. High-end appliances, including 2 full-size SubZero refrigerators, Dacor double ovens, and a Miele dishwasher, ensure that every culinary need is met with luxury and efficiency. Ascend the grand staircase to find the primary bedroom suite, a supreme sanctuary of comfort, complete with a romantic fireplace, radiant heated floors in the bathroom, an attractive dressing room with two walk-in closets. The second floor also includes a bright, well-equipped laundry room with abundant cabinetry and counter space, and a gracious guest room with a hall bathroom. Rounding out this level are two large bedrooms, each with a tailor made walk-in wardrobe and dressing area connected by a spacious jack & jill bathroom with a new soaking tub, separate shower and water closet. One level up is the ultimate in flexible living with a spacious family room centered around a gas fireplace with exquisite marble surround, two additional bedrooms and a full bathroom. Designed for leisure and entertainment, the lower level is equipped with a state-of-the-art home theater. Experience cinematic brilliance with a 4K-capable projector and a massive 158-inch projector screen. Immerse yourself in audio excellence with a THX/Dolby Atmos 11.2 speaker system featuring Klipsch speakers strategically placed for optimal sound. The seating area comfortably accommodates 8-10 guests, ensuring an unforgettable viewing experience. When you're ready for more active entertainment, step outside to the custom designed, heated basketball court featuring a floating "Maple TuffShield ShockTower" floor, installed by Snap Sports Athletic Surfaces in 2016. This product is easily removable if you prefer two extra garage parking spaces. This unique amenity creates a space for recreational activities and lively gatherings for family and friends. Finally, if you're seeking private guest accommodations or income-generating potential, the 1 bedroom/1 bath coach house above the 2.5 car garage serves as a wonderful addition, offering versatile living space and an opportunity for added convenience and flexibility.With its unparalleled architectural significance and modern amenities, this home offers a rare opportunity to experience the timeless allure of the Prairie School design. Schedule a showing today to immerse yourself in the luxury and charm of the James Fletcher Skinner House.

605 Linden Avenue, Oak Park

$1,450,000
6 Beds 4 Baths 12060968 MLS CLOSED Status
Splendor! This stately and impressive home is one to be treasured! Much admired Classic Revival home is sited on a lush half acre of land in the heart of the Estate section of Oak Park. This 6 bedroom 3.1 bath home is the Crown Jewel of American architecture at its finest. With inspiration from the Columbian Exposition, architect Harvey L. Page designed an alluring home that has epitomized distinctive living for more than a century. Discover the beauty in the details and the finishes, crafted to present with harmony and symmetry. Take delight in the ambiance, space and convenience of this home! A majestically scaled full height front porch bordered with columns welcomes all! Enter through a gracious set of double doors with stunning diamond paned leaded glass. Exceptional craftsmanship is present in finishes throughout the home. Soaring 10' ceilings, gorgeous art and leaded glass windows, picturesque palladium windows, beamed and cove ceilings, ornately finished fireplaces, intricate artisan millwork, all elements combine with a spectacular presence throughout the home. Gorgeous living room with bayed windows, elegant library-office with French doors, the formal dining room showcases a stunning crystal chandelier and offers a lovely hosting alcove. The home's architectural details and finishes are without match! Incredibly spacious and updated kitchen begins with a large butlers pantry designed as a connecting service to the dining room, a walk-in pantry, quartz island with induction cook top, stainless steel appliances and an airy and bright breakfast room with walls of windows! First floor guest bedroom features a very generously sized walk-in closet. Chic updated powder room completes the first floor. Gorgeous wide wood staircase brings you to the second level. All bedrooms are of a lavish scale with large windows that capture the sunshine throughout the day. The bedrooms are generously proportioned, providing ample space for relaxation and privacy. Each room offers a sense of tranquility and comfort, ensuring a restful retreat. The primary bedroom is a grand space with it's southern bay window and ornamental fireplace. The primary bath has marble flooring and a full vanity flanked by closets. The home gym is like no other with ample space for a full workout. The second floor laundry room features generous cabinetry and counter space - a much appreciated convenience. The center hall or back staircase brings you to a private and peaceful ensuite wing with bedroom, sitting room with wet bar and full bath. It's the perfect private retreat for extended family and guests. A rare opportunity presents now to own a treasured home of unparalleled grace and timeless appeal that seamlessly combines tradition and character with modern lifestyle conveniences. Experience the epitome of refined living in this distinguished and gracious heirloom home!

637 N Euclid Avenue, Oak Park

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Oak Park, IL · Curated MLS Search

Estate Homes in Oak Park, IL

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

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