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$625,000
3 Beds 3 Baths 12716773 MLS
LOCATION! LOCATION! LOCATION! INVESTOR & FLIPPER SPECIAL! Rare opportunity to own a historic English Tudor Revival home in one of Highland Park's most desirable neighborhoods. This partially renovated property offers exceptional upside for investors, flippers, rehabbers, or buyers looking to customize a truly one-of-a-kind home while preserving its architectural heritage. This 3-bedroom, 2.5-bath English Tudor Revival home is a rare Krenn-Dato model, showcasing timeless architectural details and rich history. Backed by Edith Rockefeller McCormick, Krenn-Dato homes are celebrated for their distinctive craftsmanship, including decorative half-timbering, a classic brick and stucco facade, steep gables, prominent chimneys, and charming multi-paned windows. Beautifully refinished hardwood floors and fresh paint throughout blend seamlessly with preserved original features, including vintage light fixtures, original windows, doors, hardware, staircase woodwork, and other decorative details that highlight the home's historic charm. The main level features a functional kitchen ready for your personal updates, a spacious living room centered around the original wood-burning fireplace, a formal dining room, a cozy den, a pantry, and a convenient half bath. Upstairs, you'll find three generously sized bedrooms and two full bathrooms. The unfinished basement includes a laundry area and offers outstanding potential for additional living space, a recreation room, home office, fitness area, or ample storage-making it an excellent opportunity for investors, flippers, or buyers looking to add value and customize the home to their vision. Outside, enjoy a large, fully fenced backyard with mature trees, along with a private front yard that enhances the home's curb appeal and serene setting. Ideally located in a top-rated school district, this true showstopper is surrounded by parks and forest preserves and is within walking distance to the Metra station for an easy downtown commute. It is also just minutes from the beach, Fort Sheridan Forest Preserve, restaurants, shopping, and neighborhood playgrounds. This home is proudly featured as part of the Highland Park Historic Homes Bike Tour. The owner, a professional builder, offers a unique opportunity to complete additional renovations-including new windows, bathrooms, a custom kitchen, and a finished basement-for an additional $75,000-$150,000, based on the buyer's preferences. Buyers may also choose to complete the renovations themselves, making this an outstanding value-add opportunity with significant upside. Some images may be virtually enhanced. The home is also available for lease. Property is being sold AS-IS.

3107 Dato Avenue, Highland Park

$1,900,000
6 Beds 5 Baths 12716063 MLS
This exceptional Highland Park residence offers nearly 5,300 square feet of impeccably designed living space, including a beautifully finished lower level, on an expansive lot just shy of an acre. Featuring 6 bedrooms and 4.5 baths across three finished levels, the home blends timeless elegance with modern sophistication. Sun-drenched interiors showcase wide-plank hardwood flooring, designer finishes, and seamless living and entertaining spaces. The chef's kitchen is outfitted with premium Bosch and Fisher & Paykel appliances, custom cabinetry, Taj Mahal quartzite countertops, and an expansive built-out pantry, flowing effortlessly into gracious gathering areas. A rare and highly desirable feature, the home offers two luxurious primary suites-one on the main level and one on the second floor-providing incredible flexibility for multigenerational living or the convenience of ranch-style living with a first-floor primary retreat. Designed for both everyday comfort and entertaining, the home also features a beautiful sunroom overlooking the backyard and an impressive 600-square-foot deck, creating the perfect setting for indoor-outdoor living and large-scale gatherings. Generously sized secondary bedrooms, spa-inspired baths, and a cozy lower level complete the home. With nearly every element thoughtfully updated-including the roof, windows, deck, balcony, mechanicals, landscaping, and more-this residence offers the feel of new construction in an exceptional Highland Park location within the sought-after Sherwood, Edgewood, and Highland Park High School districts.

1848 Balsam Road, Highland Park

$650,000
3 Beds 2 Baths 12715083 MLS
**East Highland Park Craftsman with 3 bedrooms and 2 full baths. Well-maintained with many major updates, but needs cleaning and some cosmetic freshening. Features hardwood floors, enclosed front porch, spacious living and dining rooms, eat-in kitchen with cherry cabinets, and a first-floor full bath with walk-in shower next to the family room-ideal for guests. Three upstairs bedrooms with walk-in closets. Dry basement with spray foam insulation, newer hot water heater, copper plumbing, sump pump, and additional crawl space storage. Large landscaped yard and 2.5-car garage. Excellent location near Rosewood Beach, downtown Highland Park, Ravinia, Metra, trails, schools, and more. Solid home with great potential in a prime location. Photos from previous listing

1223 Ridgewood Drive, Highland Park

$2,550,000
4 Beds 6 Baths 12714956 MLS
IMPRESSIVE PRICE IMPROVEMENT!!!The epitome of luxurious one-level living. Set on a magnificent 3+ acre parcel in an exclusive private enclave, this extraordinary property is surrounded on three sides by the Heller Nature Preserve, offering 97 acres of protected land, serene privacy, and breathtaking natural beauty. Enjoy miles of scenic trails ideal for hiking, cross-country skiing, and horseback riding-an unmatched setting with endless possibilities. This remarkable 5,000 sq. ft. modern masterpiece showcases custom architectural features, high-end designer finishes, and a versatile floor plan perfectly suited for both everyday luxury living and grand-scale entertaining. The open-concept design seamlessly connects the great room, dining area, and gourmet chef's kitchen, while soaring ceilings and walls of glass flood the home with natural light and frame stunning views of the expansive grounds. The home offers the best of both worlds-an impressive open layout complemented by serene private spaces, including two primary suites, two additional bedrooms, 5.1 baths, a stunning office, and a delightful private den. The main primary suite is a true retreat, offering complete privacy, a spa-like bath with steam shower, custom walk-in closets, infrared sauna and built-in custom cabinetry. The finished lower level includes a family room, exercise room, bedroom, and full bath. Additional highlights include a heated 3+ car attached garage and professionally landscaped and hardscaped grounds featuring a tennis court and a heated in-ground spool (small pool with hot tub jets and fountains). While the property is not subdividable, it presents a rare opportunity to create an estate compound with additional structures such as a guest house, pool house, secondary residence, auto court, pickleball court, or horse stables. Direct access to the Heller Nature Preserve trails further enhances this exceptional offering. Truly a rare opportunity-offering a lifestyle that is difficult to replicate.

1551 Mill Trail, Highland Park

$2,500,000
5 Beds 7 Baths 12703691 MLS
Introducing The Lincoln Collection - an exclusive offering of nine new construction residences on the former Lincoln School site. Currently under construction and available September 1, 2026. Perfectly positioned on a professionally landscaped .31-acre homesite, this exceptional 6-bedroom, 6.1-bath home offers approximately 5,500 square feet of curated living space across three impeccably finished levels. A light filled foyer with statement herringbone hardwood floor sets the tone, flowing into a sophisticated dining room. The home's centerpiece is a sun-drenched, open-concept kitchen and great room designed for effortless living. High ceilings create a dramatic backdrop, along with fireplace flanked by built-ins. The chef's kitchen is outfitted with premium Monogram appliances, sleek quartz counters and backsplash, walk-in pantry, custom rift-cut white oak cabinetry and warm bronze accents-blending timeless elegance with modern sophistication. The main level also features a highly desirable first-floor bedroom suite with en-suite bath, ideal for guests or a private office. A designer powder room and a beautifully appointed mudroom with custom built-ins offering both function and style leads to a 2 car heated garage. Upstairs, the serene primary suite is a true retreat, bathed in natural light, tray ceiling and complemented by dual organized walk-in closets. The spa-inspired bath featuring quartz countertops, bespoke white oak cabinetry, a deep soaking tub, an oversized shower and private commode closet. Three additional bedrooms are generously sized and each include their own private en-suite bath. Large second floor laundry room with built-in cabinetry. The fully finished lower level delivers an elevated lifestyle experience with a sprawling recreation room, dedicated fitness studio, private sauna, additional bedroom, full bath and abundant storage - designed for both relaxation and entertaining. Professionally landscaped fenced yard with patio and large side yard creates the ideal outdoor entertaining spaces. This residence offers a rare combination of new construction, architectural detail and walkable lifestyle, just moments from vibrant downtown Highland Park, the Green Bay Trail and Lake Michigan.

701 Lincoln Avenue, Highland Park

$1,249,000
12713953 MLS
This prime East Highland Park location being only 4 lots from the lake is most magical divine landscaped setting on 0.72 of an acre. Complete with breathtaking ravine views, this mid century modern property is ready to be reimagined or even reinvented with a new home. From the moment you arrive, a very secluded driveway leads you down to impeccably manicured grounds layered with colorful flowers & perennials outlined by a mature canopy of trees creating a natural fence of privacy. This environment creates a sense of serenity, transforming the grounds into a private, Zen-inspired retreat. Inside this light-filled artistic home that embraces its spectacular natural setting, you are welcomed with an entire wall of panoramic windows allowing the outdoors to come inside creating a modern vibe that is waiting for your creative touches. An open floor plan ideal is for entertaining with the chef's kitchen that opens to dining & living with north facing ravine vistas. Private office leads to the sanctuary first-floor primary suite with direct access to private patio & completed with a spa-inspired bath and huge walk thru closet. Follow the floating stairs to the second floor with an additional bedroom and full bath with ample opportunity to reconfigure the home's footprint to accommodate even more bedrooms. With the lake breezes, sit back and entertain on the expansive wrapped patio and enjoy nature and relaxation. Whether you choose to enjoy this sophisticated home as it is, thoughtfully reimagine it, or create a remarkable new estate, this is a truly rare opportunity in one of the North Shore's most coveted east locations. Get ready to explore the options this special property offers! Estate sale, AS IS.

235 Moraine Road, Highland Park

$1,249,000
2 Beds 3 Baths 12710115 MLS
This prime East Highland Park location being only 4 lots from the lake is most magical divine landscaped setting on 0.72 of an acre. Complete with breathtaking ravine views, this mid century modern property is ready to be reimagined or even reinvented with a new home. From the moment you arrive, a very secluded driveway leads you down to impeccably manicured grounds layered with colorful flowers & perennials outlined by a mature canopy of trees creating a natural fence of privacy. This environment creates a sense of serenity, transforming the grounds into a private, Zen-inspired retreat. Inside this light-filled artistic home that embraces its spectacular natural setting, you are welcomed with an entire wall of panoramic windows allowing the outdoors to come inside creating a modern vibe that is waiting for your creative touches. An open floor plan ideal is for entertaining with the chef's kitchen that opens to dining & living with north facing ravine vistas. Private office leads to the sanctuary first-floor primary suite with direct access to private patio & completed with a spa-inspired bath and huge walk thru closet. Follow the floating stairs to the second floor with an additional bedroom and full bath with ample opportunity to reconfigure the home's footprint to accommodate even more bedrooms. With the lake breezes, sit back and entertain on the expansive wrapped patio and enjoy nature and relaxation. Whether you choose to enjoy this sophisticated home as it is, thoughtfully reimagine it, or create a remarkable new estate, this is a truly rare opportunity in one of the North Shore's most coveted east locations. Get ready to explore the options this special property offers! Estate sale, AS IS.

235 Moraine Road, Highland Park

$495,000
2 Beds 2 Baths 12710002 MLS
Beautifully renovated, designer's own corner penthouse with balcony and southwest treetop views in a pet-friendly, boutique 12-unit elevator building, near vibrant downtown Highland Park and Sunset Valley Golf Club. Two bedrooms plus Den, 2 baths, 2 car heated garage parking. Bright & open concept condo is a rare find at over 1,900 sf, with a spacious covered balcony. Originally designed as a 3-bedroom unit, the current den could be converted back to a third bedroom. Rentals are not allowed. Features & designer updates include: * Two indoor parking spaces, convenient to both the elevator and the exit. * Laundry in unit. * All new electric: outlets, switches, LED can lights, new efficient / quiet exhaust fans in bathrooms. * Kitchen remodel: new Stainless Steel appliances, new Stainless Steel sink, tile backsplash, faucet & disposal, new quartz countertops, refinished cabinets, new hardware * Bathrooms: New Kohler comfort height toilets, updated plumbing * All walls & ceilings, and trim thru entire condo painted * New sound insulated flooring, new carpet in bedrooms * New glass panels on some interior doors to improve light flow * New window treatments and woven shades throughout * New balcony Note: Most furnishings can be sold with the unit, if desired, selected and scaled for the room sizes. With its abundance of natural light, generous room proportions and flow out to the covered balcony, the expansive living room, dining room and family room will be the heart of the home, ideal for hosting guests around the built-in bar or simply relaxing at the end of the day. A crisp color palette and large windows enhance the space and views. The well-equipped eat-in kitchen is a cook's delight. You will enjoy 1000 Deerfield Road's secluded yet central location, with town, train, park, pool, shopping, restaurants, and even golf at nearby Sunset Valley Golf Club, all at your fingertips. Floor plan is under "Additional Information"

1000 Deerfield Road Unit #303, Highland Park

$1,199,000
5 Beds 4 Baths 12702603 MLS
Escape to your own private nature retreat! Nestled on a beautifully large wooded 1/3-acre corner lot in coveted Sherwood Forest. This exceptional 4092 sq ft home offers the perfect blend of space, comfort, and versatility to fit today's lifestyle, including 2 potential home offices, an upscale Primary Bathroom, and lots of storage space. The home welcomes you with warmth and charm. Natural light floods its big picture windows from its desirable south and west exposures. The spacious living room features a cozy wood-burning fireplace, while the elegant dining room, with French Doors, provides the ideal setting for memorable gatherings. A comfortable family room offers an inviting space to relax, and the updated kitchen is thoughtfully designed with everything a home chef could want. Enjoy the beauty of every season from the fabulous screened porch, where you can unwind while overlooking the tranquil surroundings. Also on the main level is a flexible bedroom or home office, conveniently located adjacent to a full bath. A New mudroom is right off the 2 1/2 car attached garage. Upstairs, the expansive primary suite serves as a true private retreat. This luxurious space includes a recently renovated spa-inspired bathroom, a separate dressing area with abundant closet space, and a versatile bonus room perfect for a sitting room, nursery, home office, or fitness space. Three additional generously sized bedrooms and an updated hall bath complete the second floor. The newly refinished basement expands your living space with a recreation room, utility room, and ample storage. Ideally located in a sought-after neighborhood with the choice of attending either Highland Park or Deerfield High Schools, this one-of-a-kind home combines peaceful natural surroundings with outstanding convenience. Don't miss this rare opportunity to make this exceptional property your own! See Home Improvement List under Additional Information.

1557 Cavell Avenue, Highland Park

$1,795,000
5 Beds 9 Baths 12709731 MLS
Surrounded by the peaceful, natural beauty of the Hybernia Preserve, this luxurious home offers water views and privacy seldom experienced. ***New Roof, Gutters, and Patio - 2020***New Exterior Paint - 2023***Kitchen Renovation - 2018***New Dishwasher - 2021***New Disposal - 2025***New Marble and Hardwood Flooring***Closets Professionally Organized - 2021***Whole House Generator - 2018***New Basement Egress Windows - 2023***A dramatic 2 story, marble floored foyer welcomes you and flows effortlessly to an open floor plan with a gorgeous volume ceiling great room with floor to ceiling windows that flood the residence with loads of natural light! Recently updated, this home offers 6 Bedrooms (including a first floor primary suite AND a first floor guest suite that includes a dedicated guest bath) 6 full and 3 half baths, and a full basement which treats you to a spa room that rivals your most favored paid luxury spa experience. The attached garage offers parking for 3 cars (plus a lift to accommodate an additional 4th vehicle) and incredible additional storage. Additional updates include ***2018 whole house generator, ***new within 3 years HVAC, new water heaters, ***2018 flooring and new interior paint, 2021 professionally organized closets, 2018 incredible chef's kitchen with sub-zero fridge, wolf range, wine/bev cooler, and much more...while invaluable upgrades include wine cellar, theatre room, professional fitness room, 4 zone heating and cooling, security, irrigation, professional car lift in the garage...simply A+++. Step out to your gorgeous patio outdoor space which includes a gazebo complete with grilling station for your outdoor entertainment. You will feel like you are miles away from everything...and yet be only minutes away from everything that downtown Highland Park has to offer. Award winning schools and easy access to attractions like Lake Michigan beaches, Ravinia Park, Chicago Botanical Gardens, and so much more! This home is an absolute MUST SEE!

1745 Sundrop Circle, Highland Park

$4,995,000
9 Beds 14 Baths 12678213 MLS
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

$873,500
4 Beds 2 Baths 12699488 MLS
A welcoming front porch sets the tone for the warmth and charm you'll find inside this home. This beautifully maintained brick home combines timeless character with modern updates, all situated on an expansive 50' x 220' professionally landscaped, fenced lot and a two-car, recently structurally redone detached garage. The interior features hardwood floors, solid oak doors, and elegant crown molding throughout. The thoughtfully designed main level offers an inviting flow, beginning with a spacious living room featuring a cozy fireplace. A dedicated first-floor office provides the perfect work-from-home space, while the separate dining room serves as the heart of the home for gatherings and entertaining. The large eat-in kitchen offers abundant cabinetry, a breakfast bar with seating for 3-4, and additional table space. It opens seamlessly to the bright first-floor family room, which has a large window facing the gorgeous yard, creating an ideal layout for everyday living. A full bath is located on the main level. The second floor includes three generously sized bedrooms and a second full bathroom with a walk-in closet. The third floor provides a private fourth bedroom with an adjoining sitting area, making it an excellent retreat for guests, extended family, or a live-in arrangement. The basement is divided into two functional spaces. One side is finished, perfect for a play area, craft room, or a second office, the laundry area, and a convenient toilet-only bathroom. The unfinished portion offers a utility room and excellent storage space. With over $100,000 in improvements, classic architectural details, generous living areas, and a convenient location close to shopping, dining, downtown amenities, and commuter rail service, this home is ready to welcome its next owners to add their own personal touch. Floor plans provided under "Additional Info".

1538 Oakwood Avenue, Highland Park

$1,250,000
5 Beds 6 Baths 12693363 MLS
Nestled on a private property this residence stands as a testament to sophisticated design and timeless elegance. This custom-built residence is poised on a lush, wooded lot, offering a serene backdrop that feels worlds away while remaining moments from the very best of North Shore living. Spanning three finished levels of meticulously curated space, the home features five expansive bedrooms and four full and-two-half baths. The interior architecture is defined by a sense of scale and grace, perfectly suited for both grand-scale entertaining and quiet, private moments. The flow is perfect on the 1st level with a private office and a flexible bedroom/ 2nd office with half baths nearby. A bright Kitchen overlooks the yard and patio and features an island with a large eat-in area. At the heart of the home, the primary suite serves as a true sanctuary, offering generous proportions and a refined atmosphere for relaxation. The lower level is a destination unto itself. Fully finished and designed for wellness and recreation, it boasts a private sauna and steam room-an effortless way to incorporate a spa-like lifestyle into your daily routine. Beyond the property lines, the lifestyle afforded by this location is unmatched. Residents enjoy close proximity to the world-class performances at Ravinia Festival and the pristine sands of Rosewood Beach. This address also offers convenient access to highly regarded local educational institutions, including Braeside Elementary, Edgewood Middle School and Highland Park High School.

201 Aspen Lane, Highland Park

$525,000
4 Beds 3 Baths 12703113 MLS
Commuter's dream meets turnkey luxury! Tucked away in a highly convenient Highland Park location with effortless highway access, this spacious 4 bedroom, 3 bathroom end unit townhome offers the ultimate low maintenance lifestyle. Boasting over 2,500 sq. ft. of bright, open living space, the main level features gleaming hardwood floors, a generous living room, and a separate dining room ideal for entertaining. The beautifully updated eat in kitchen shines with granite countertops, stainless steel appliances, and premium cabinetry, opening directly to your own private patio. Retreat upstairs to the massive primary suite complete with a cedar walk in closet and updated private bath. Enjoy the ultimate convenience of second floor laundry, a 2 car attached garage, a first floor bedroom with on-suite bath, and association amenities including an outdoor pool. Just minutes from downtown Highland Park shopping, dining, and the expressway, welcome home!

739 Concorde Drive, Highland Park

$169,000
2 Beds 2 Baths 12697341 MLS
Wonderful, light-filled 2-bedroom, 2-bath condominium featuring an open floor plan in the highly desirable Sunset Woods Condominiums, a 62+ senior community. Wood floors in kitchen and foyer. Convenient in-unit laundry completes the home's thoughtful layout. Enjoy an exceptional array of community amenities, including a party room, game/card room, library/TV room, exercise room, rooftop terrace, and a beautifully landscaped paver patio with BBQ grills overlooking the park. One garage parking space is available on a rotating basis. Ideally located near shopping, restaurants, a movie theater, the Metra train, and more. Residents also enjoy access to the free Senior Connector bus, providing transportation to destinations throughout Highland Park. Sunset Woods is an affordable housing development. All prospective buyers must submit an application to determine eligibility. Please contact your Realtor for qualification requirements and additional details. No rentals permitted. Units must be owner-occupied.

891 Central Avenue Unit #336, Highland Park

$599,000
4 Beds 2 Baths 12706025 MLS
Welcome to 552 Burton Avenue, a beautifully maintained all-brick mid-century split-level ideally situated in one of Highland Park's most sought-after neighborhoods. Located just steps from the Ravinia Festival, the Metra station, local shops, and restaurants, and directly across from Brown Park with its tennis courts and green space, this home offers an exceptional combination of charm, convenience, and lifestyle. Built in 1956, this sun-filled residence features hardwood floors, crown molding, and abundant natural light that creates a warm and inviting atmosphere throughout, highlighted by new bedroom ceiling fans and updated dining and living area light fixtures (2025). The updated kitchen is beautifully appointed with rich cherry cabinetry, stainless steel appliances (2022), and granite countertops, flowing seamlessly into the main living spaces for effortless entertaining. The upper level offers three spacious bedrooms and a refreshed bathroom with a new toilet (2025), while the finished lower level provides a versatile fourth bedroom or office, an upgraded full bathroom (2026), and flexible space for recreation. Outside, the property boasts excellent curb appeal with a completely replaced driveway (2021) and a private backyard oasis featuring a new custom fence with a privacy cover (2025) and fresh landscaping (2025). The home features a long list of recent capital improvements, including a new water heater with an overflow protector (2026), a new garbage disposal (2026), a sealed, capped, and tuck-pointed chimney (2025), a new furnace (2024), custom living room blinds (2024), a wired 24/7 outdoor security video camera (2024), a new A/C system (2020), a newer roof (2016), and upgraded electrical service (2015). **Per Highland Park City Planner, a garage is possible!** Just minutes from Rosewood Beach, the Chicago Botanic Garden, and downtown Highland Park, this exceptional home offers the best of North Shore living in an unbeatable Ravinia location.

552 Burton Avenue, Highland Park

$4,399,000
5 Beds 6 Baths 12501567 MLS
NEW CONSTRUCTION luxury single-family home coming soon to Highland Park within sought after Ravinia Elementary School boundaries. Designed for both everyday living and elevated entertaining, the main level features a private home office with striking glass and iron doors, a formal dining room framed by oversized windows, two powder rooms, and an expansive living room that seamlessly opens to the kitchen. A vaulted sunroom overlooks the backyard, filling the home with natural light and creating the perfect indoor-outdoor connection with a COVERED PATIO off the kitchen, sunroom and living room. The true centerpiece is the show-stopping chef's kitchen, complete with a full scullery for additional prep, storage, and seamless hosting. Upstairs, you'll find four spacious en-suite bedrooms, a versatile loft/den space, and a thoughtfully designed laundry room equipped with dual washers and dryers for ultimate convenience. The finished lower level is built for lifestyle and wellness, featuring a fully outfitted exercise room with private spa amenities (sauna and steam), an expansive recreation room, an additional bedroom and full bath, and a flexible bonus space ideal for a playroom, card room, or media lounge with heated radiant floors throughout the entire basement. Offering 6 bedrooms, 6 full bathrooms, and 2 half baths. This exceptional home also includes an attached HEATED 3-car garage and sits on nearly half an acre of flat, usable land. A rare opportunity to own new construction in one of Highland Park's most desirable neighborhoods. PHOTOS ARE RENDERINGS AND OF PREVIOUS PROJECT. DELIVERY END OF SEPTEMBER 2026 *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.

966 Wade Street, Highland Park

$4,400,000
4 Beds 6 Baths 12705843 MLS
Experience unparalleled luxury on the lakefront. This 5,500 SF NEW CONSTRUCTION home tucked away at the end of a quiet cul-de-sac has been meticulously curated for modern living with impeccable design. The expansive floor plan features four generous bedrooms, each with its own en-suite bathroom, including a refined primary retreat complete with 12 foot ceiling, a private balcony overlooking iconic Lake Michigan and 2 lavish walk-in closets. Culinary artistry is redefined in the exceptional chef's kitchen, outfitted with professional-grade appliances and a discreet scullery-perfect for both upscale entertaining and daily life. Exceptional amenities include a finished basement with a full bath, second-floor laundry , a first-floor office, a powder room, and expansive living spaces that are bathed in natural light. Perfect indoor-outdoor harmony is achieved through a serene three-season room, and a stone terrace, all providing ideal vantage points to enjoy the tranquil lakefront setting. Enjoy an unbeatable Highland Park location on a commanding .63-acre lot with panoramic Lake Michigan views. Stairs down to the beach are adjacent to back yard, shared with residence on the street.

22 Lakeview Terrace, Highland Park

$539,000
3 Beds 2 Baths 12702605 MLS
New roof and freshly painted inside and out! Opportunity knocks on coveted Castlewood Road! This 3-bedroom, 2-bathroom home features a private office/den ideal for remote work, a study, traditional living space and sits on a generous 1/3-acre lot in one of Highland Park's most established neighborhoods. Built in 1956 with the solid bones of mid-century construction, this 2,751 sq ft property offers the kind of square footage and lot size that buyers simply can't find at this price point in 60035. There is also a 654+ sq ft basement converted from a crawl space, featuring a lifetime transferable waterproofing warranty. The basement has passed inspection by the City of Highland Park and would only require the addition of a staircase to complete. Whether you're an investor, a DIY enthusiast, or a buyer looking to build instant equity, this is the canvas you've been waiting for. The spacious lot offers plenty of room to grow - think expanded outdoor living, lush landscaping, or simply the breathing room that's increasingly rare in today's market. Add in a 1 car detached garage, and you've got serious flexibility right from day one. Priced to reflect its as-is condition, this is your chance to get into Highland Park at a compelling entry point - and create exactly the home you've always wanted, down to every last detail. Properties with this combination of lot, location, and upside don't come around often. Bring your contractor, bring your creativity, and bring your best offer.

1958 Castlewood Road, Highland Park

$1,399,000
4 Beds 5 Baths 12696254 MLS
Welcome to effortless luxurious living in Highland Park. This stunning custom contemporary 6-year-young home offers 5 spacious bedrooms, 4 half baths, and an open floor plan bathed in natural sunlight from every angle. The flexible floor plan blends style, comfort and functionality. Sunny foyer, soaring ceilings, designer finishes, and fixtures throughout. Sun-filled great room flows into chef`s kitchen with stainless steel appliances, pantry, quartz countertop, and storage. A separate dining room sits just off the kitchen and family room, creating the perfect layout. Ideal for family living and entertaining, plus much more. Beautiful hardwood floors throughout the home with all high-end finishes. A custom staircase leads to the second floor. The primary suite includes remote control window treatments, walk in closet, plus a private deck with Trex flooring. The master bath has heated floors, a large shower, and twin sinks. Three additional spacious bedrooms, 2 with jack and jill bath, plus a hall bath with whirlpool tub. The finished basement adds incredible living space with a full bath, bedroom, and large entertainment room, along with a separate professionally soundproofed area ideal for podcasting, recording, or a quiet home office. The garage features epoxy flooring and slat board walls. The home is recently painted and in impeccably maintained. There is also a shared outside area with a play area, fire pit, and walking path. Truly a fabulous home with more features. Taxes do not reflect any exemptions and may be lower for a qualified buyer.

2009 Skyelar Court, Highland Park

$440,000
3 Beds 2 Baths 12697929 MLS
Rarely available three-bedroom, two-bath condominium offering an exceptional combination of space, natural light, and value. Enjoying a desirable southern exposure, this inviting residence features a thoughtfully designed split-bedroom floor plan, generous room sizes, and an oversized private balcony. A welcoming foyer leads to spacious living and dining areas, creating an ideal setting for everyday living and entertaining. The kitchen features maple cabinetry, a comfortable eating area, abundant storage, and direct access to the oversized south-facing balcony. Privately situated, the primary suite features hardwood flooring, exceptional closet space, plantation shutters, and an en-suite bath with dual sinks, a soaking tub, and a separate shower. Two additional generously sized bedrooms, both with hardwood flooring, share a spacious hall bath. Plantation shutters enhance one of the secondary bedrooms, while the other offers direct access to the balcony, providing flexibility as a guest room, home office, or den. Additional highlights include in-unit laundry, excellent storage throughout, a one-car attached garage, and a convenient main-level storage locker. Ideally located just moments from downtown Highland Park, Metra, restaurants, shopping, and Lake Michigan. Property conveyed in as-is condition.

1534 Mcdaniels Avenue Unit #3E, Highland Park

$369,900
2 Beds 3 Baths 12699757 MLS
Welcome to this absolutely charming 2-bedroom, 2.1-bath townhome in a highly sought-after Highland Park location w/ beautiful pond views. The living room features a gas-log fireplace, overlooks the pond, and has direct access to a private patio, perfect for relaxing or enjoying your morning coffee. The kitchen offers ample cabinet space, a casual eating area, and a large window overlooking the courtyard. A detached garage is conveniently located just off the kitchen.Upstairs, the spacious primary suite enjoys peaceful pond views. The second bedroom is generously sized, and the loft provides flexible space for a home office, reading area, or den. Additional features include abundant guest parking and a location close to downtown Highland Park, the Metra, parks, pools, shopping, dining, and expressway access. This home offers a great opportunity to update and make it your own while enjoying low-maintenance living in a scenic setting.

1071 Deerfield Place, Highland Park

$1,099,000
5 Beds 4 Baths 12699551 MLS
Nestled on a quiet, tree-lined street in Highland Park's coveted Braeside neighborhood, this spacious 4-bedroom, 3.1-bath residence presents a rare opportunity to create your dream home in one of the North Shore's most desirable communities. Freshly painted throughout in June 2026, the home offers an exceptional floor plan, generous room sizes, and the perfect canvas for buyers looking to add their own style and cosmetic updates over time. Designed for both everyday living and entertaining, the home features multiple gathering spaces, a private backyard retreat with an in-ground pool, and a two-car attached garage with additional parking for a third vehicle on the exterior pad. Whether hosting summer barbecues, celebrating special occasions, or simply unwinding after a long day, the outdoor space offers the kind of lifestyle many buyers seek but rarely find. Beyond the property itself, the location is truly exceptional. Residents enjoy close proximity to the world-renowned Ravinia Festival, where summer evenings are filled with concerts beneath the stars and picnics on the lawn. The stunning Chicago Botanic Garden is just moments away, offering year-round beauty, walking paths, seasonal events, and educational programming. Commuters appreciate convenient access to the nearby Metra stations for an easy trip into downtown Chicago, while Highland Park's vibrant downtown provides an outstanding collection of boutiques, restaurants, coffee shops, and community events. Outdoor enthusiasts will love Highland Park's beautiful Lake Michigan beaches, extensive trail systems, neighborhood parks, and recreational amenities that make it easy to enjoy an active lifestyle. Located within highly regarded Highland Park schools, this home combines space, location, and lifestyle in a way that is increasingly difficult to find. Offered in AS-IS condition, 35 Barnard Lane represents an outstanding opportunity for buyers with vision to personalize a well-located home with solid fundamentals, desirable amenities, and access to everything that makes Highland Park one of the North Shore's most sought-after communities.

35 Barnard Lane, Highland Park

$1,995,000
6 Beds 8 Baths 12697109 MLS
Tucked away in one of Highland Park's most coveted east-of-Sheridan enclaves, just moments from the lakefront and jaw-dropping Rosewood Beach, this sprawling residence blends timeless architecture with refined amenities and over 10,000 square feet, offering a rare lifestyle of elegance, privacy, and ease. Situated on a lush, tree-canopied setting at nearly 3/4 of an acre, with manicured gardens, sculpted landscaping, and a grand circular drive that compliments the home's scale and serenity. Stucco-clad home with clay tile roof and a grand entry with soaring ceilings and dramatic architectural details create a deep first impression. The voluminous great room is a showstopper-anchored by a striking marble fireplace, floor-to-ceiling arched windows, and a dazzling custom chandelier, flooding the space with natural light and framing views of the verdant grounds. A light flooded kitchen awaits with walls of windows, custom cabinetry, sleek quartz counters, professional-grade appliances, and a sculptural center island-equal parts form and function. For more casual gatherings or multi-generational living, the lower-level second kitchen offers additional flexibility with a full suite of amenities. The expansive finished basement stretches out with nearly endless possibilities-all options on the table for large-scale recreation, home theater, gym, creative studio or multi-generational living. Full size multi person sauna on site as future feature of workout space. Multiple zones of heat and air, thoughtful storage throughout, full mud room with laundry center and attached three car garage. Unique configuration with six bedrooms plus library above grade and 6.2 baths with main level primary suite with dual primary baths including oversized soaking tub and multiple walk-in closets. 4 bedrooms are en-suite and there are over 12 skylights for abundant natural lighting. Tranquil and private rear yard with an oversized terrace framed by mature evergreens, flowering borders, and stone accents. Fruit trees and raised gardening beds, this secluded oasis is ideal for alfresco dining, morning meditation, or moonlit entertaining. Set just a short stroll from Lake Michigan and Highland Park's historic Ravinia District, within the Ravinia school district, 260 Beech offers a rare opportunity to own a substantial residence in one of the North Shore's most iconic neighborhoods.

260 Beech Street, Highland Park

$2,599,000
6 Beds 7 Baths 12686426 MLS
This Beautiful Home on Over an Acre in the Heart of Highland Park Boasts Soaring Barrel Ceilings over 20' High and 5 Fireplaces. Amazing Home for Entertaining with a Magnificent Great Room, a Banquet-Sized Dining Room with a Butlers Pantry, a Wonderful Screened Porch and a Balcony Overlooking the Backyard- which includes Ravines and a Huge Yard, large enough for a tennis/pickleball court, an outdoor pool and more- Accessed by a Bridge! The Double Island Chefs Kitchen has a Fireplace, Walk-in Pantry, Professional Series Appliances, Dumb-waiter and Way Too Many Features to List! The Main Floor has 3 Bedrooms and 3 1/2 Baths and the Entire 2nd Floor is a Romantic Hideaway Primary Suite with its Own Family Room, Fireplace, Huge Walk-in Closet and Spa-like Bath. There is potential to create a 1st Floor Primary if desired. This Home offers over 8000 Sq Ft plus 2330 Sq Ft in the Finished Walkout Basement featuring a 40' Indoor Pool with a Wall of Glass that Open to the Outdoors! 2 Additional Bedrooms and Full Baths, a Massive Workout Room, an Amazing Home Theater, and a Summer Kitchen in the Walkout Basement. 5 Zones of Heat and Air, and a 3+ Car Garage. Located just moments from the Vibrant Shops, Dining, and Cultural Landmarks of Downtown Highland Park, the Metra Train and the Lakefront, this Home offers a Lifestyle of Convenience and Sophisticated Comfort. It's not just a place to live-It's a Place to Thrive. Truly a Must See!

493 Hazel Avenue, Highland Park



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