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The listings below include active single-family homes, condos, townhomes and multifamily properties across Cook, DuPage, Will, Lake, Kane and McHenry counties. No preset price ceiling. Availability and prices can change; confirm auction and placeholder pricing. This is not a price-reduction-only feed.

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86 Prospect Avenue, Highland Park
$5,495,000
8 Beds ⋅ 12 Baths ⋅ 12781411 MLS ⋅ ACTIVE Status
Stop dreaming, start living. Rarely does a residence of this magnitude and pedigree become available. Nestled just steps from the whispering shores of Lake Michigan, 86 Prospect Avenue is more than a home-it is a masterpiece of architectural significance. Originally commissioned in 2006 by a prominent local builder as his personal sanctuary, this estate has recently emerged from a multi-year, multi-million dollar transformation, championed by Red Rock Custom Homes and Earth Developments, as well as design carefully curated by Kara Mann Interiors, resulting in a seamless fusion of timeless North Shore grandeur and 2026's most sophisticated modern luxuries. Thoughtfully situated on three hand-selected well-located parcels, the land now totals .87 acres of meticulously manicured grounds. Your approach to the home is cinematic, featuring a brand new circular paver drive, adorned by timeless gas lamps and lush potted plants, which leads to a majestic porte-cochere, a private gated motor court, and a heated five-car garage. The rear grounds are anchored by a 45-foot heated pool recently totally redone and resurfaced, complemented by a stone fire pit and sprawling covered patios. The heart of the home is a bespoke Chef's Atelier featuring a striking marble and walnut island, Viking and Wolf ranges, Traulsen refrigeration with a dedicated commercial walk-in refrigerator, and Sub-Zero integrated drawers. This culinary suite transitions effortlessly from a sun-drenched breakfast room complete with a custom eating area with built-in benches to an expansive formal dining room anchored by a stately wood-burning fireplace. With over 14,000 square feet of finished living space, the home offers a versatile floor plan of eight to ten bedrooms, including a primary suite that serves as a bastion of tranquility with a private balcony, seasonal lake views, dual spa-inspired bathrooms, and two expansive custom dressing rooms. Four additional ensuite bedrooms and a hidden play area grace the second floor, while the third floor is dedicated to wellness with a professional gym, massage/yoga room, and recreation room. The walk-out lower level provides a sophisticated retreat with a second kitchen, three guest suites, three full bathrooms, and a large recreation room with a dedicated cabana bath. Built with a "forever" mindset, the estate includes a full-service elevator, two laundry suites, an executive library, a whole-house generator, and an advanced irrigation system. This is not merely an acquisition of real estate, but the acquisition of a lifestyle without compromise. Step into the perfect blend of timeless architecture and luxury north shore living. Welcome home! A few final touches being completed as we speak. Nearly $2.5m was invested in this home since in the last two years, a full list of improvements available upon request.

86 Prospect Avenue, Highland Park
Palos Park
$5,400,000
5 Beds ⋅ 8 Baths ⋅ 12752214 MLS ⋅ ACTIVE Status
Welcome to what may be the most extraordinary private estate ever offered in the Southwest Suburbs. Set on approximately 2 acres surrounded by mature forest, this magnificent estate delivers a combination of architectural grandeur, resort-style living, unparalleled amenities and exceptional infrastructure. Every element has been thoughtfully designed and built using only the finest materials. From the moment you arrive through the gated entrance, an expansive, artistically designed brick drive unfolds through dramatic lighting and intricate custom inlays, culminating in a spectacular circle drive. The residence offers approximately 11,000 square feet, 7 1/2 bathrooms and 6 bedrooms with an additional 3 flex rooms. Car enthusiast's dream with a porte-cochere and an extraordinary 8-car garage, including a garage bay equipped with lifts. Inside, grandeur begins in the impressive foyer, where soaring architecture and meticulous craftsmanship immediately establish the caliber of this remarkable home. DaVinci Roof, copper gutters, 8-foot interior doors, five fireplaces, custom architectural details, radiant heat and extraordinary finishes continue throughout. The formal dining room features a dramatic decorative ceiling, while the gourmet kitchen is complemented by a private butler's pantry and designed for both grand-scale entertaining and intimate everyday living. A beautifully appointed mudroom offers individual closets, while the dedicated office features custom built-ins and its own balcony. Upper level bedrooms all complete with their own built-in furniture and ensuites. Elevated primary with gorgeous decorative ceiling that includes 2 chandeliers and adjoining balconies. Spa inspired bath unlike any you've seen or even imagined. Dual under-lit vanities. Private commode tiled floor to ceiling, and spectacular bubble tub! The home's expansive living spaces flow effortlessly between sophisticated interiors and spectacular outdoor environments. The backyard rivals the finest private resorts. At its centerpiece is an extraordinary 25' x 60' saltwater swimming pool, complete with an electric pool cover, artistic fire features, dramatic water elements and two distinctive fire-art installations. The pool is surrounded by expansive paver terraces designed for effortless unforgettable summer evenings. The spectacular pool house elevates outdoor living to an entirely different level, featuring: full bathroom, dedicated laundry room, fireplace, and locker/changing area. Expansive sliding glass doors offer direct access to the concrete pool surround. Nearby, a covered outdoor bar and kitchen create the perfect setting for entertaining on any scale. Built-in grill, dishwasher and extensive storage, allowing the entire backyard to function as a sophisticated extension of the home. An additional outdoor fireplace anchors the paver patio, while dramatic lighting, fire baskets and artistic water features transform the property after sunset into an unforgettable private retreat. And then there is the view from the above primary suite balcony. It is a fully realized private estate, meticulously crafted over two years with an extraordinary level of investment, attention to detail and uncompromising standards. From the gated entrance and spectacular illuminated paver drive to the eight-car garage, from the grand foyer to the private theater, from the primary suite balcony to the magnificent resort-style pool and pool house, every element has been designed to make an impression. Priced far below the seller's cost, this is an exceptional opportunity to acquire a truly one-of-a-kind luxury estate at a level of quality, scale and amenity rarely found anywhere in the Chicago area. Mechanicals include 600-amp electrical service, whole-house generator, public sewer and water with a private well dedicated to irrigation/sprinkler use. For the buyer who refuses to settle for ordinary, this is the property that defines extraordinary. It's a must see!!

Palos Park
6413 S County Line Road, Burr Ridge
$5,295,000
6 Beds ⋅ 9 Baths ⋅ 12776405 MLS ⋅ ACTIVE Status
Welcome to 6413 County Line Road-an extraordinary new construction estate set on a full acre along Burr Ridge's prestigious Millionaires Row feeding into Hinsdale Central High School. Masterfully designed with timeless architecture and best-in-class finishes, this home offers a rare blend of luxury, comfort, and craftsmanship. The exterior makes an immediate statement, wrapped entirely in natural stone and limestone with a terracotta clay tile roof and Marvin windows throughout. Natural cobblestone pavers lead to a grand entrance framed by bluestone steps and manicured landscaping. Inside, you're welcomed by radiant-heated white Thassos marble floors with black inlays, soaring ceilings, and exquisite millwork throughout. The chef's kitchen is outfitted with Sub-Zero, Wolf, Thermador, and Bosch appliances, marble countertops with full slab backsplash, and custom cabinetry in a mix of painted, glazed, and stained finishes. A second full kitchen on the lower level adds exceptional functionality. Each bedroom is a private suite with its own balcony, while the primary bathrooms are outfitted in floor-to-ceiling marble with digital Kohler and Grohe fixtures and radiant heat. Throughout the home, 5" white oak flooring adds warmth, and four custom staircases with hand-forged wrought iron offer both elegance and flow. The lower level is designed for entertaining and wellness, featuring a full bar, state-of-the-art theater, sauna, steam room, and a custom three-level elevator. Located near top-rated schools, country clubs, Hinsdale Hospital, and just minutes from downtown Hinsdale and Burr Ridge, this home delivers unmatched quality in one of Chicagoland's most coveted locations.

6413 S County Line Road, Burr Ridge
275 Sussex Lane, Lake Forest
$5,275,000
8 Beds ⋅ 11 Baths ⋅ 12720778 MLS ⋅ ACTIVE Status
Ralph Lauren print campaigns, features in Architectural Digest, film productions, and even the latest Crate & Barrel holiday catalog all point to one thing: great architecture never goes out of style. And more than a century later, David Adler's "Innisfail I" is every bit as extraordinary today. Set on over two breathtaking acres, this landmark estate is ready now to be experienced through a new 2026 lens. The pool, spa, tennis court, and sauna all are just the side features that bring this magnificent lifestyle home to life, as David Adler designed is country luxury estate with one thing in mind...a destination for all to enjoy. His one primary focus with his interiors was "proportions"- always wanting his rooms to have volume with soaring ceilings but still feel intimate. He finished these spaces with endless sets of French doors bringing the gardens inside, and exquisite original details from intricate millwork to Versailles and herringbone parquet floors. The oversized reception hall immediately sets the tone, opening through 10-foot doorways to the spectacular great room where walls of French doors, handcrafted millwork & grand chandeliers frame the endless terraces & gardens beyond. Sun-drenched entertaining spaces flow effortlessly from the living to the dining room, richly paneled library and sunroom, while the Chef's kitchen, oversized butler's pantry and sunny breakfast room make the house equally suited for everyday living. Upstairs, a beautiful hotel-level wrapped wrought-iron staircase leads to eight bedrooms, including the expansive primary suite with fireplace and private dressing room. The third floor changes the mood completely with a speakeasy-style bar, bedroom and full bath-proof that a house this important can still have a little fun. And then there are the grounds which alone today to duplicate would be over $2m in just design and install. Originally designed by legendary landscape architect Jens Jensen, the estate unfolds across formal gardens, sweeping lawns and mature trees, with a pool, spa and tennis court creating the ultimate private country retreat. Innisfail I has been photographed, published and filmed for generations for a reason. Today estates can be built, not doubt about that, but there is nothing like architecture that can always withstand the test of time. NOW it's time to re-imagine this space with a hue of transitional colors, clean-lined furniture and a revamp from gold to simply white. This is a designer's dream palate as this estate is just waiting to be the next showpiece estate in the North Shore as the pedigree is already in place!

275 Sussex Lane, Lake Forest
594 N Plum Tree Road, Barrington
$5,250,000
6 Beds ⋅ 12 Baths ⋅ 12718774 MLS ⋅ ACTIVE Status
A rare opportunity to own an impressive European-inspired estate in prestigious Barrington Hills. Blending the romantic elegance of French Chateau architecture with the timeless character of an English Tudor country manor, offering just under 14,000 square feet of exceptional living space on 31 private acres. Designed for both grand entertaining and everyday luxury, this remarkable residence features six private en-suite bedroom retreats, six fireplaces, and four levels connected by a private elevator. Expansive living and dining spaces, a gourmet chef's kitchen, richly appointed library, private office, main level bedroom with full bath and impressive primary retreat are just a few of the home's many offerings. The finished lower level is designed for recreation and entertaining, featuring a private home theatre, kitchenette, wine cellar, fitness room, billiards area, spacious family room, and guest bedroom with full bath. Enjoy the beauty of mature grounds, creating a peaceful country setting with endless potential just minutes from shopping, dining, UP-NW Metra, and award-winning Dist 220 Barrington schools. An exceptional estate combining timeless craftsmanship, impressive scale, and an unmatched Barrington lifestyle.

594 N Plum Tree Road, Barrington
3026 N Lake Shore Drive, Chicago
$5,250,000
6 Beds ⋅ 9 Baths ⋅ 12737336 MLS ⋅ ACTIVE Status
Rare opportunity to own an impeccably maintained single-family residence on Lake Shore Drive, situated on an expansive 34' x 134' lot with approximately 9,000 square feet under roof. This exceptional home offers 7 bedrooms and 7.5 baths and features multiple outdoor living spaces, with 30' x 20' garage rooftop terrace with a custom outdoor kitchen-ideal for entertaining. A dramatic foyer welcomes you into the main level, which features a gourmet kitchen, great room, and a striking living area with soaring 20+ foot ceilings, a gas fireplace, and a dining space overlooking Lake Shore Drive. The kitchen is appointed with custom white cabinetry, natural stone countertops, professional-grade appliances, a dedicated coffee and beverage nook, and a built-in breakfast banquette. A striking custom double staircase connects the upper levels. The second-floor features three light-filled ensuite bedrooms with custom-built-in storage. The third floor is home to a refined primary suite with custom millwork, a fireplace, and a tucked-away sitting area. The spa-inspired primary bath features an oversized rain and steam shower, a soaking tub, dual vanities with Calacatta marble countertops, and heated marble floors. A spacious dressing room features a center island. An additional ensuite bedroom and a laundry room complete this level. The top floor showcases exceptional custom woodwork and offers a large bar and entertainment lounge, a half bath, a workout room, and two rooftop decks with open views. The lower level includes a family/media room, wet bar, full bath, an ensuite bedroom, ample storage, oversized refrigerator and freezer capacity, and a mudroom with direct access to the 3-car garage. Additional highlights include a Control4 audio system, an elevator, individual HVAC zones, a security system, an irrigation system, and outdoor snow-melt. You have secure private alley access to a 3-car attached garage.

3026 N Lake Shore Drive, Chicago
451 W Deming Place, Chicago
$5,200,000
6 Beds ⋅ 6 Baths ⋅ 12760503 MLS ⋅ ACTIVE Status
A rare opportunity to own a 5,245-square-foot single-family home with direct interior access to the exceptional amenities of 2550 N. Lakeview. Set on coveted Deming Place, this extra-wide, six-bedroom residence combines the privacy, space and outdoor living of a single-family home with the services, security and amenities of a premier full-service building, all accessible without ever stepping outside. One of the home's most distinctive features is its exceptional connection to outdoor space. The kitchen and great room open directly to the home's own private terrace, which in turn leads to 2550 Lakeview's expansive 1.25-acre private park, an extraordinary extension of the home's backyard. Residents also enjoy the children's playground and dog park, along with the full complement of 2550 Lakeview amenities, including an indoor pool and hot tub, fitness center, sauna and steam rooms, Pilates studio, sun deck, recreation room, library, private party room, receiving room, dry cleaning services, daily garbage pickup, 24-hour security and professional building staff. The residence is exceptionally well designed across four levels, all served by a private passenger elevator. The entry level offers a gracious foyer with extensive built-in storage, an at-grade guest suite or home office with full bath, and a fully outfitted mudroom with direct access to the home's private attached two-car garage. Two additional deeded garage spaces provide an extraordinary total of four indoor parking spaces. The main living level is bright and generously proportioned, with large windows overlooking Deming Place. Spacious living and dining areas connect to the kitchen and great room through an oversized butler's pantry complete with walk-in pantry, coffee bar, wine center and desk area. The eat-in kitchen features custom cabinetry, commercial-grade appliances, two dishwashers and quartzite countertops and opens to a family room with fireplace and custom built-ins. Just beyond is a large private terrace with direct access to the park. The bedroom level is anchored by a substantial primary suite with a separate dressing room, two walk-in closets and spa bath featuring heated floors, freestanding tub and oversized steam shower. Two additional bedrooms, a full bath and a walk-in laundry room complete this level. The upper floor offers two additional bedrooms, a full bath, powder room and large recreation room with wet bar opening to a second private terrace. Soaring ceiling heights, extensive custom millwork and built-ins, Control4 integrated audio, lighting and security complete the residence. An exceptional combination of single-family living, multiple private outdoor spaces, four-car indoor parking and seamless access to 2550 Lakeview's 1.25-acre park, amenities and services in one of East Lincoln Park's most desirable locations.

451 W Deming Place, Chicago
441 W Deming Place, Chicago
$5,200,000
5 Beds ⋅ 5 Baths ⋅ 12740927 MLS ⋅ PRICE CHANGE Status
An exceptional East Lincoln Park residence offering sophisticated design, generous proportions, and an extraordinary connection to the outdoors. Ideally positioned on the block to capture beautiful natural light, this meticulously designed home enjoys views of the private park and Chicago skyline from the spectacular rooftop deck. The expansive, thoughtfully conceived floor plan is ideal for both gracious entertaining and everyday living. The main level features an impressive open living space anchored by a chef's kitchen with high-end finishes and appliances, flowing seamlessly into the living and dining areas. Floor-to-ceiling doors open to a park-facing terrace, creating a wonderful indoor-outdoor experience in the heart of the city. Upstairs, the luxurious primary suite offers a private retreat with a beautifully appointed bath and abundant closet space. An additional room can be used as an office, additional closet, or den. Three additional bedrooms are conveniently located on one level, while the flexible floor plan provides the opportunity for a fifth and optional sixth bedroom, ideal for guests, a home office, fitness room, or additional family space: wide floor plan with generous room sizes, first-floor ensuite bedroom/den, open living floor featuring a chef's kitchen and impeccable design, living space seamless to park-facing terrace, entire-floor primary suite with optional 6th bedroom, ideal for guests, a home office, or fitness room. Throughout the residence, timeless transitional finishes, custom millwork, exceptional craftsmanship, and carefully considered architectural details create a home. Generous room sizes and multiple living spaces provide remarkable flexibility. Three bedrooms on one floor, complemented by gorgeous timeless transitional finishes throughout. A secure two-car underground garage provides direct access and additional storage, with a rare opportunity to purchase a third garage space with the residence. You are welcome to use 2550 Lakeview amenities, which include a 1.25-acre private park, indoor pool, fitness center, whirlpool, sauna & steam rooms, sun deck, yoga/pilates room, dog run, valet guest parking, and receiving room. Located in one of East Lincoln Park's most desirable residential settings, this is a beautifully executed city home combining the scale and privacy of a single-family residence with exceptional outdoor space and the convenience of one of Chicago's most sought-after neighborhoods. This beautiful home can be shown with 24 hours notice. Nothing quite like it on the Market.

441 W Deming Place, Chicago
1515 N North Park Avenue, Chicago
$5,200,000
7 Beds ⋅ 6 Baths ⋅ 11755660 MLS ⋅ ACTIVE Status
Nestled on the prestigious North Park Avenue, Significant Mansion stands as a remarkable architectural gem in the vibrant Old Town/Gold Coast neighborhood. This custom-built residence, constructed from exquisite masonry brick and limestone, spans an impressive 8,000 square feet and occupies a generous double lot measuring 50 feet in width. The property boasts an expansive side yard and entrance, multiple balconies, and a covered rooftop deck, crowned by a magnificent turret tower that presents breathtaking panoramic views of the city skyline and the lush, tree-lined surroundings. Featuring seven bedrooms and five and a half bathrooms, this home is a testament to meticulous design and thoughtful attention to detail. Inside, the residence showcases soaring 12-foot ceilings, rich hardwood flooring, a coffered ceiling in the living room, elaborate crown moldings, and stately 8-foot doors. The ambiance is further enhanced by three elegant wood-burning fireplaces, a five-stop elevator, and a well-appointed gym on the top floor that overlooks an impressive professional indoor basketball court. The spacious chef's kitchen is a culinary enthusiast's dream, equipped with a Wolf range cooktop and custom copper hood, built-in Wolf convection ovens, a commercial Thermador refrigerator, and luxurious granite countertops. Custom cabinetry, a large center island with counter seating, and a separate dining area create a seamless flow into the grand family room, which features yet another wood-burning fireplace. The spectacular three-season room invites relaxation with its own wood-burning fireplace and provides access to an outdoor grilling patio complete with a built-in DCS chef's grill. The home also includes a convenient mudroom with laundry facilities and direct access to the stunning side yard. The expansive primary suite is a private retreat, featuring a walk-out balcony, a dedicated staircase leading to a unique turret office, and two generous walk-in closets. The en suite bathroom is a luxurious haven, offering a double vanity, a spacious steam shower, and a jetted bathtub. Additional bedrooms are equally generous, each equipped with walk-in closets, en suite baths, and walk-out balconies. The lower level is designed for entertainment, featuring a cozy fireplace and a potential wine storage room, alongside two sizable bedrooms with walk-in closets and a full bath. Additional highlights of this extraordinary residence include a spacious attached 2.5-car garage, an automated privacy gate, a snowmelt driveway, a central vacuum system, geothermal radiant heating, Marvin windows, multiple laundry rooms, and a Sonos multi-room sound system throughout the home. Perfectly suited for entertaining large families, this unique property is ideally located near a wealth of entertainment options, exquisite dining, top-tier schools (including Latin and Parker), parks, and the picturesque lakefront. This is truly a one-of-a-kind home that promises an unparalleled living experience.

1515 N North Park Avenue, Chicago
920 W Monroe Street Unit #1801, Chicago
$5,000,000
3 Beds ⋅ 4 Baths ⋅ 12777622 MLS ⋅ ACTIVE Status
Marielle on the Park. Luxury condominiums in the West Loop. A boutique collection of generously scaled residences and penthouses at the edge of Mary Bartelme Park, moments from Fulton Market, and designed for the rare buyer who seeks more than luxury. Expansive two-, three-, four-, and five-bedroom floor plans; private terraces on select residences, park-facing and skyline views, custom finishes available for early buyers. Every detail has been thoughtfully considered, creating a home for buyers with a clear point of view who have experienced quality and know precisely how they want to live. Marielle sits at one of Chicago's most coveted locations: the West Loop's only convergence of sprawling green space and urban energy. Just outside the front door, Mary Bartelme Park unfolds before you, offering morning light across greenery, farmers markets, neighbors connecting, and a pause in a rare, lush, natural destination. The Sales Gallery is welcoming appointments just one block north of Mary Bartelme Park at 14 North Sangamon St. Prices start at $1.425 million.

920 W Monroe Street Unit #1801, Chicago
Palos Park
$5,000,000
5 Beds ⋅ 5 Baths ⋅ 12704119 MLS ⋅ ACTIVE Status

Palos Park
1752 Midwest Club Parkway, Oak Brook
$4,999,000
6 Beds ⋅ 8 Baths ⋅ 12725913 MLS ⋅ ACTIVE Status
The visionary team behind 303 Midwest Club Parkway brings to market a most spectacular offering. 1752 is more than a home; it is a statement of refined living that prioritizes light-filled spaces and premium finishes. With architecture by Moment Design and a floorplan offering flexible private suites, 1752 is an effortless fit for multi-generational living. At this early stage, meaningful customizations remain available, allowing you to enhance the home to precisely suit your personal lifestyle. Secure your future in one of the most desirable addresses where true 24 hour security allows residents to enjoy complete peace of mind, controlled access and a private, protected environment. Beyond the gates, the community provides a resort-like way of life with an impressive array of amenities designed for relaxation, recreation and connection. Court 17 is included in the area's top-rated school district consistently recognized for academic excellence (Butler - 53/Hinsdale Central 86) and is a great option for year round living or seasonal residents who value the freedom to lock and leave with total confidence. Exciting collaboration between the masterful MBC Design and Aspen Construction, a local custom builder who has been creating some of the areas most impressive homes for over 30 years. Contact LA to review preliminary plans, discuss options and reserve your opportunity before this exclusive residence is spoken for.

1752 Midwest Club Parkway, Oak Brook
1524 N Astor Street, Chicago
$4,995,000
3 Beds ⋅ 6 Baths ⋅ 12799026 MLS ⋅ NEW Status
A rare architectural offering on one of Chicago's most coveted residential streets, this is the northernmost home on Astor, distinguished by its commanding position and oversized windows overlooking the Cardinal's Mansion and Lincoln Park. The setting provides exceptional privacy and natural light, a rarity in the city. Originally designed as a mid century modern residence by noted Chicago architect I. W. Colburn, the home was later completely reimagined with a refined Art Deco inspired interior by two of the city's most respected design firms, Marvin Herman & Associates and Suzanne Lovell Inc. In 2025, the exterior was extensively renovated, including all new stucco on the walls enclosing the home's expansive private terrace. Today, the residence offers approximately 6,500 square feet of beautifully finished living space, generous outdoor areas, and two-car garage parking. Interior finishes are of exceptional quality and include bespoke millwork and cabinetry, hand-cast plaster moldings, a dramatic curved staircase with artisan-fabricated bronze and steel balusters, three distinctive fireplaces, rift-sawn white oak floors with custom inlay, limestone and marble, Donald Kaufman paint finishes, and vellum wall coverings. An elegant foyer with a walk-in coat closet, climate-controlled wine storage, and a guest bath with a hand-carved marble sink introduces the home. One level up, the main living level includes a gracious living room with a wet bar, a separate dining room, and a sophisticated kitchen with custom cabinetry and a built-in banquette. This level also includes a private office with a white alabaster fireplace and direct access to the terrace. A standout feature of the home, the north-facing terrace offers a serene setting for outdoor dining and entertaining. The top level includes a luxurious primary suite with a spa caliber bath featuring a soaking tub carved from a single block of Noir St. Laurent marble with P. E. Guerin hardware. A second en suite bedroom and a family room with an additional full bath complete the level. Curved rear stairs lead to a private bedroom suite with its own entrance, allowing guests to enter independently. Features include knotty pine paneling, a kitchenette, generous closets, an en suite bath, and French doors opening to a tranquil koi pond. The landscaping was designed by award-winning Scott Byron & Co. Ideally located near Lincoln Park, the lakefront, and downtown, this exceptional Gold Coast residence offers architectural pedigree, remarkable privacy, and extraordinary craftsmanship.

1524 N Astor Street, Chicago
2441 Woodbridge Lane, Highland Park
$4,995,000
9 Beds ⋅ 14 Baths ⋅ 12678213 MLS ⋅ ACTIVE Status
Situated on a prestigious private lane in East Highland Park, this rare lakefront offering is a Mid-Century Modern masterpiece. Designed in 1957 by renowned architect Henry L. Newhouse II for Irving B. Harris, Chicago Philanthropist, this 10,000-square-foot contemporary residence sits on nearly two acres of lush grounds with magnificent, unobstructed views of Lake Michigan. Experience the ultimate wow factor as you enter the dramatic foyer and take in the breathtaking vista. The interior features large expanses of glass and natural light, offering a flexible floor plan that flows effortlessly for entertaining and everyday living. An exquisite foyer leads to custom beveled, imported French Limestone floors and dramatic floor-to-ceiling windows that frame the water. With minimalistic aesthetic, the Chef's Eat-In Kitchen is finished with custom black walnut cabinetry, a wall of granite, gourmet appliances, and a sleek gas fireplace. The home's expansive footprint includes a main floor Primary Bedroom Suite with a secondary Primary Suite on the 2nd level and seven additional Ensuite Bedrooms, providing unparalleled space and privacy. Despite significant renovation since construction, the home still retains the core architectural integrity and mid century character established by Newhouse. For wellness and recreation, an Indoor Pool Pavilion features a Dectron temperature-controlled system, a retractable clerestory roof, a steam room, and a dedicated second kitchen equipped with Viking appliances. Outside, the tranquility of the lakefront setting takes center stage. A sparkling Outdoor Pool overlooks the water, while a private tram and stairs lead down to 150 feet of secluded beach. This is a unique opportunity to own a significant piece of architectural history with unlimited potential on the shores of Lake Michigan!

2441 Woodbridge Lane, Highland Park
875 Country Club Road, St. Charles
$4,995,000
7 Beds ⋅ 12 Baths ⋅ 12620193 MLS ⋅ ACTIVE Status
Stone Wood Manor - a 1935 stone estate by architects Frazier & Rafter- comprehensively reimagined in 2016 by Marshall Architects and Didier Custom Homes (3 year rebuild).. Set on 9.38 heavily wooded acres in the Fox River Valley that border St. Charles Country Club, the property offers privacy at estate scale, and was designed for serious entertaining. The estate presents three distinct structures/areas: the main residence, the Pool & Pool House area, and Pickleball Court / Stone Garage (with Studio space). Start your day with a nature walk on your own quarter-mile circuit that winds through the woods & leads to a serene pond. Enjoy the expansive 13,500 sq. ft. of living space. The 2016 renovation preserved the original architecture & character: every system beneath it was rebuilt & the result reads as a fully modern estate beneath unmistakably 1935 lines. Seven en-suite bedrooms include a first-floor Primary Suite with sitting area, fireplace, dressing room, and a spa bath built around a soaking tub and oversized shower. The chef's kitchen, renovated in 2021, opens to a breakfast room and shares the main level with a formal dining room, a piano room with concert digital piano, and a wine room. The English Lower Level functions as a dedicated entertainment floor: a Ralph Lauren-inspired bar, an eight-seat theater updated in 2024, a private office, fully equipped gym, game room with snack kitchen, and a spa lounge complete with built-in pedicure tub, massage table, and salon station. Five fireplaces warm the residence. Beyond the main house, the entertaining grounds unfold across two further structures. Dual waterfalls frame the free form pool and spa tub area surrounded by the bluestone patio with outdoor kitchen, & fire pit area. The Pool House (also fully renovated) - with custom bar, fireplace, poker room, full bath, changing room, and laundry, purpose-built for entertaining - away from the main residence. The 2022 lighted Pickleball/Sport Court has easy access to the Stone 2-Car Garage (with bar & 2nd floor Studio) as well as private patio & fire pit - perfect for post game wind-down. Other amenities include: natural gas backup generator, private well support the property's systems, smart home automation, extensive sound system throughout & more. The estate is zoned for horses, available fully furnished, and includes a golf membership to the championship 18-hole St. Charles Country Club. Despite the seclusion, the property sits roughly four minutes from DuPage Airport, placing private aviation within easy reach. 89+ PG eBrochure.

875 Country Club Road, St. Charles
435 Thorne Lane, Lake Forest
$4,950,000
5 Beds ⋅ 8 Baths ⋅ 12718757 MLS ⋅ ACTIVE Status
Set on 1.28 acres at the end of a quiet East Lake Forest cul-de-sac, this exceptional contemporary home offers 8,078 square feet above grade plus finished lower level. Walls of glass, a dramatic floating staircase and open living spaces frame views of the pool, terraces and wooded ravine. The kitchen features custom ebony cabinetry, high-end appliances and a large island and opens directly to the family room and outdoor living areas. Substantial recent improvements include new HVAC systems, a new heated driveway, extensive landscaping and drainage work, custom interior upgrades, a whole-house generator and a Crestron lighting and shade-control system. The lower level includes a media room, workout room, bar, guest accommodations and indoor sport court, while the renovated in-law suite has its own kitchen and den. Additional highlights include six bedrooms, 7.1 baths, an elevator, heated pool and spa, screened porch with retractable screens and fireplace, and a heated garage that can accommodate up to 6 cars.

435 Thorne Lane, Lake Forest
24w141 Hobson Road, Naperville
$4,950,000
7 Beds ⋅ 9 Baths ⋅ 12753503 MLS ⋅ ACTIVE Status
Nestled on 3 breathtaking acres of lush grounds and whimsical gardens, this impeccable Grand English Tudor Estate offers over 12,000 square feet of masterfully crafted living space. Conceived by engineer Ted Reitenbach and designed by the talented Barbara Grzelczyk, this magnificent home took three years for skilled craftsmen and artisans to create - built like no other here every detail bears witness to that devotion. A private gated entry leads to a stunning paver brick driveway with adjoining walkways and manicured gardens professionally designed, setting a grand tone before you even step inside. Step through grand 8 foot cherry wood cathedral doors into an opulent limestone foyer crowned by a breathtaking 250-pound antique chandelier with a built-in elevator mechanism for effortless elegance. Antique leaded glass windows with built-in blinds grace every first-floor window, while Pella windows with interior shades adorn the upper levels. Every hardware piece was handmade in Lithuania, and Perure hinges were selected for their unmatched Old World craftsmanship. The remaining chandeliers throughout are irreplaceable one-of-a-kind antique pieces that cannot be found or replicated, each adding timeless distinction to every space they illuminate. The formal dining room stuns with a hand-carved plaster ceiling and artisan-crafted leaded windows bathing the space in natural light. The distinguished library features soaring cathedral ceilings, custom-crafted light fixtures, and built-in cabinetry with grand mesh doors. The family room soars with 20-foot ceilings, 14 expansive windows, irreplaceable antique chandeliers, a majestic Chicago fire brick fireplace, and a dramatic second-story balcony overlook. Antique solid wide white oak floors flow beautifully throughout. Five magnificent fireplaces, every one crafted with authentic Chicago fire bricks, grace this extraordinary estate. This estate proudly features two full chef-caliber kitchens - seamlessly connected by a dumbwaiter elevator - making large-scale entertaining and multi-generational living truly effortless. The primary gourmet kitchen showcases French hand-glazed cabinetry, granite countertops, a professional Viking range with grill, griddle, convection oven and warming drawer, dual Sub-Zero refrigerators behind extraordinary handcrafted panels, and a charming limestone fireplace breakfast area. A true butler's pantry with an additional Sub-Zero walk-in refrigerator behind cherry paneling bridges the kitchen and formal dining room. Two expansive first-floor primary suites provide ideal accommodations for multi-generational living, in-law quarters, or distinguished guests. The walkout lower level is an entertainer's paradise: home theater, fitness room with sauna, wine cellar-ready room, billiards area, secret passageways, a second full chef-caliber kitchen, and generous storage. Outside, extensive patios, meandering garden paths, and enchanting landscaping create a storybook backdrop for grand entertaining, anchored by a beautifully crafted exterior storage building designed to match the manor architecture. The entire grounds are enclosed by a 6-foot wrought iron fence ensuring total privacy. Mechanical excellence includes three zoned HVAC systems a dedicated radiant heat boiler serving the basement, garage and front entrance steps, a state-of-the-art private water system, natural slate roof with copper gutters, and a smart home system. A once-in-a-generation opportunity for the discerning buyer who demands timeless elegance, unparalleled provenance, and the absolute finest in luxury living - nestled within one of the most coveted and sought-after communities in all of Chicagoland.

24w141 Hobson Road, Naperville
787 E Deerpath Road, Lake Forest
$4,900,000
4 Beds ⋅ 7 Baths ⋅ 12749263 MLS ⋅ ACTIVE Status
A rare Lake Forest offering. Ideally situated just steps from Lake Michigan and the heart of town, this exceptional custom-built all-brick residence offers a remarkable blend of architectural integrity, refined craftsmanship and effortless livability. Set on a beautifully scaled one acre site, the 6,952 square foot home was designed and built in 2002 with an appreciation for enduring quality and timeless style. From the slate roof and handsome copper gutters to the rich wide-plank walnut floors, every detail reflects a level of craftsmanship rarely found in newer construction. The elegant interiors are complemented by an exceptional kitchen featuring custom cabinetry imported from England, creating a sophisticated yet inviting setting for everyday living and entertaining. A private handsome wood paneled library with fireplace provides a very private office space. The home offers five bedrooms, five full and two half baths, with generously proportioned living spaces that flow beautifully for both intimate gatherings and grand-scale entertaining. The finished Lower Level adds an additional 1,351 square feet of exceptional living space, complete with second family room with cozy fireplace, Bar area, 5th bedroom, exercise room and dedicated home theater. Beyond the exceptional architecture and craftsmanship, the location is truly special. Enjoy the rare convenience of walking to the Lake Forest Beach, downtown Lake Forest, Metra train, shopping, dining and the many amenities that make Lake Forest such a wonderful place to call home. Interior photos coming October 14th.

787 E Deerpath Road, Lake Forest
1447 N Dearborn Street Unit #1N, Chicago
$4,900,000
4 Beds ⋅ 5 Baths ⋅ 12733434 MLS ⋅ ACTIVE Status
Eight new construction, exclusive, full-floor residences offer a refined lifestyle that blends eclectic interiors with unparalleled luxury and an estimated delivery date of December 2026. Discover an extraordinary opportunity to live boldly at 1447 N. Dearborn, an enduring Gold Coast icon. Nestled on a quiet street, these residences overlook treelined and courtyard views, offering a sense of peace in the heart of the city. Each residence at 1447 N. Dearborn boasts direct elevator access and expansive private outdoor spaces. Residence 1N is a 4 bedroom, 4.1 bath, duplex-down residence with 10 ft ceilings on both levels and exquisite selections for all finishes. With 5215 SQFT of living space, this sprawling condominium lives more like a single-family home. Common areas include a beautifully landscaped courtyard with a graceful fountain that offers a moment of stillness, a wellness room for yoga, meditation, and light exercise, and tandem, attached, heated garage parking for 2-cars. Estimated delivery is late December 2026.

1447 N Dearborn Street Unit #1N, Chicago
488 Park Avenue, Glencoe
$4,895,000
4 Beds ⋅ 7 Baths ⋅ 12795539 MLS ⋅ ACTIVE Status
Designed to make daily living in Glencoe a walk in the Park, this exceptional new construction home blends crisp, transitional design with an ideal open layout for today's busy lifestyle. The main level features a fully equipped state of the art chef's kitchen, expansive family room with double-sided fireplace open to living room, custom-built library with fireplace and bright mudroom. The second level includes four en-suite bedrooms, highlighted by a private primary suite with dual walk-in closets and a luxurious marble bath, along with a conveniently located laundry room. The spectacular lower level provides another level of recreation and relaxation for the whole family with a sport court, exercise room, basement bar, infrared sauna, and a fully equipped media room. Additional highlights include a garage for four cars (two attached and two detached) and a beautifully landscaped, fenced yard featuring a pergola, outdoor fireplace, and bluestone patios. Ready Winter 2027! Don't miss the opportunity to collaborate with the Newgard team to tailor this home to your family's unique lifestyle.

488 Park Avenue, Glencoe
453 W Briar Place Unit #PH-WEST, Chicago
$4,795,000
5 Beds ⋅ 6 Baths ⋅ 12594762 MLS ⋅ ACTIVE Status
Welcome to 453 West Briar Place in Chicago's East Lakeview neighborhood, just steps from the lakefront. From the award-winning builder of 647 West Melrose street and numerous custom single family homes, this boutique, six-unit building covers nearly three city lots, features 30-foot wide living spaces and has attached garage parking with direct elevator access to the residences. The units are finished like a custom home with wide plank flooring, professional appliances, and Kalista plumbing fixtures. This tri-plex Penthouse has 5 bedrooms and 5.5 baths-- perfectly laid out over nearly 5000 square feet of indoor and 1300 square feet of outdoor spaces. A separate dining room, rec-room, two wet bars, and an outdoor kitchen are just a few of the rare amenities included. A private roof top deck with elevator service is also included. 2 deeded parking spaces come standard with time still to customize your dream home! *Renderings and plans, etc. are for marketing purposes only; finishes/plans may change at the discretion of Seller. Buyer(s) and their representation to confirm all finishes prior to purchase. Buyer's Broker must attend all showings/appointments.

453 W Briar Place Unit #PH-WEST, Chicago
1109 W Washington Boulevard Unit #PH8D, Chicago
$4,750,000
5 Beds ⋅ 5 Baths ⋅ 12676725 MLS ⋅ PRICE CHANGE Status
Welcome to the crown jewel of the iconic Hayden boutique building in the heart of the West Loop! Featured in Interiors Magazine, this extraordinary duplex-up penthouse is one of the largest floor plans in the building, spanning two breathtaking levels with over 5,000 square feet of living space, with private dual-elevator access, soaring ceilings, and walls of windows that flood every inch of the home with natural light and offer sweeping views of the city. Professionally designed by Judy Olson Dunne of Butter and Eggs, and meticulously elevated by its current owners with no detail overlooked and no expense spared, this is not just a home but a true architectural showpiece! At the heart of it all is a kitchen that redefines what luxury cooking looks like, featuring a 60-inch Wolf and Sub-Zero refrigerator-freezer, a full suite of high-end Wolf and Sub-Zero appliances, a stunning combination of leathered quartzite, butcher block, and zinc countertops, and a custom-built-in hood as a true focal point. A dedicated scullery with 2 wine fridges makes this kitchen as functional as it is beautiful, with exceptional storage throughout. Designer lighting elevates every corner of the home, and custom built-ins have been thoughtfully integrated throughout in closets, living areas, and beyond, all executed at the highest level. The expansive family room anchors the main level with a beautifully appointed built-in gas fireplace, and a gracious separate dining space completes the entertaining flow. Open your wall of windows to create indoor-outdoor living, and step outside to the professionally landscaped deck, designed by Botanical Concepts, complete with concrete pavers, custom planters, a built-in grill, and irrigation, creating an outdoor sanctuary above the city. Two additional bedrooms round out the main level, one a perfect private office or gym complete with a sauna, the other transformed into a stunning library with a custom-built-in bar with marble countertops and a beverage fridge. Escape upstairs to the bedroom level, where the primary suite is extraordinarily generous, outfitted with custom built-ins, a dream walk-in closet outfitted with custom Italian cabinets, and a spa-caliber bath featuring heated floors, a steam shower, a double vanity, and finishes that are wholly bespoke, the result of owners who spared nothing in making this home their own. Two additional spacious bedrooms are en suite, including one beautifully appointed and covered in grasscloth wallpaper, a second living space that could easily be converted into an additional bedroom, and a dedicated nook reimagined as a custom library. A generous laundry room on the upper level, with additional closets and a convenient secondary entrance, provides seamless everyday functionality. Two deeded garage parking spaces and a fully automated Crestron system controlling sound, lighting, HVAC, and Lutron throughout round out this extraordinarily considered home. Exceptional location in the heart of the West Loop, steps from the neighborhood's most celebrated dining and culture, including Girl & the Goat, Monteverde, Au Cheval, Aba, Trivoli Tavern, Bar Tutto, Trino, and ample parks for the pup, including Mary Bartleme Park. Do not miss the rare opportunity to own this one-of-a-kind penthouse that is a true masterpiece!

1109 W Washington Boulevard Unit #PH8D, Chicago
811 Judson Avenue, Highland Park
$4,700,000
5 Beds ⋅ 6 Baths ⋅ 12778380 MLS ⋅ ACTIVE Status
A distinguished custom Grunsfeld estate, privately set on nearly 2 acres of exceptional tableland and ravine, offers a singular combination of architectural pedigree, uncompromising craftsmanship, and extraordinary privacy. This remarkable 5-bedroom, 5.1-bath residence showcases timeless design, an exceptional floor plan, and the highest quality finishes throughout. Soaring ceilings, dramatic floor-to-ceiling windows, wide-plank oak floors, English sycamore cabinetry, and a striking fossil stone fireplace create interiors of understated elegance and enduring sophistication. The first floor primary suite serves as a private retreat, featuring a walkout to the grounds, an expansive dressing and closet area, and a luxurious spa-inspired bath. Three additional bedrooms and two baths are located on the second floor. Outdoor living is equally impressive, with a swimming pool and expansive bluestone terrace overlooking the beautifully landscaped grounds. Additional amenities include a wine cellar, 6 car garage, 800-amp electrical service, whole-house generator, and fenced ravine. An increasingly rare offering for the discerning buyer seeking refined luxury.

811 Judson Avenue, Highland Park
1407 N Hoyne Avenue, Chicago
$4,695,000
5 Beds ⋅ 7 Baths ⋅ 12639287 MLS ⋅ ACTIVE Status
A sophisticated presence, landmark status, architectural integrity, and an unprecedented outdoor footprint for Wicker Park, 1407 N. Hoyne Ave. is a one-of-a-kind opportunity for the homeowner who wants an expansive city estate with pedigree and a modern program. Originally built for beer baron John H. Rapp in 1886, this 8250 SqFt-square-foot, 5 bed/4.3 bath single-family home underwent a multi-year renovation and restoration by Rugo Raff Architects. Preserving elements of its Victorian charm while optimizing sightlines and integrating first-class finishes was paramount. This special home's unheard of 98' x 110' lot affords multiple green spaces, including a deep front yard with mature landscaping, a side yard with raised garden beds and a European-style pergola. Inside, an elegant entry plus an oval-shaped entry hall link to a lovely living room with an abundance of natural light, a traditional turret, and a wood-burning fireplace, and a formal dining room just beyond with hand-scraped walnut floors. The custom chef's kitchen stuns with O'Brien Harris cabinetry, white quartzite countertops, professional-grade Wolf/Sub-Zero appliances, an herb garden, a full butler's pantry, a breakfast dining space with banquette seating, and a built-in desk. The main level also features an intimate family room with built-in walnut cabinetry and a chic beverage center, and two beautiful limestone terraces accessed via French doors: a 12' x 23' west terrace for open-air entertaining and a 12' x 17' side terrace that's perfectly appointed for large-scale alfresco dining with an outdoor kitchen and a built-in grill. A striking example of this home's flawless interior architecture is the centrally located, curving suspended staircase. The second level is devoted to two secondary bedrooms (one with custom bunk beds), the first of two laundry rooms, and an impressively spacious primary suite with a sitting area, a custom dressing room, a walk-in closet, and a marble-clad ensuite bath with two vanities, a soaking tub, and a deluxe shower. The third floor presents two designer offices--a handsome den with knotty alder wood floors and a gas fireplace, a cozy den with a wet bar, an exercise room, and yet another polished guest bedroom. But there's more... This truly magnificent home also comes complete with a fully finished garden level with a massive playroom that opens onto a basement terrace, a wine room, a kitchenette, another large guest bedroom with den perfect for related living, a second laundry room, a walk-in storage room, and a custom mudroom that connects to an attached garage. Additional callout details and amenities include restored original doors and hardware, custom woodwork and trim throughout, designer lighting and wallcoverings throughout, four total fireplaces, 97 Marvin windows, a Lutron lighting system, self-irrigating planters on both terraces, and an excess of custom interior storage. Walking distance to Wicker Park proper and the world-class shopping and dining that extends from the neighborhood's famed Six Corners, 1407 N. Hoyne Ave. is a one-of-a-kind home with uncompromising design and comforts. Coach house available separately and additional garage parking can be added if acquired, please inquire.

1407 N Hoyne Avenue, Chicago
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