Highland Park, IL Homes for Sale with Pool

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

Brett Larson Redfin Corporation

Experience effortless living at 1250 Park Avenue West, a beautifully renovated corner-unit condominium in highly desirable Brooke Estates. Thoughtfully designed for both everyday living and entertaining, the open floor plan features rich wood engineered flooring and a beautifully updated kitchen with stainless steel appliances, granite countertops, a decorative tile backsplash, and an island for

Julie Mangione Coldwell Banker Realty

Welcome to 1871 Elmwood Dr! This charming solid brick and stone Ranch is set on a beautifully landscaped corner lot in the heart of coveted Sunset Park. This 2 Bedroom, 2 Bath, updated and meticulously maintained home offers both comfort and style. The lovely Living Room features crown moldings, a woodburning fireplace, custom built ins and an expansive bay window outfitted with plantation

Ellen Chukerman Compass

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

Honore Frumentino @properties Christie's International Real Estate

Move right into this extremely well maintained Chantily home. Located in the center of the sought after Chantily complex. Large eat-in-kitchen flows right into family room. Large combo living room and dining room are perfect for entertaining. Primary suite includes tons of closet space including a cedar closet and new carpeting. Two additional generous size bedrooms and hall bath. Upstairs

Ted Pickus @properties Christie's International Real Estate

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

Daniel Straus Baird & Warner

Elegant and sophisticated custom built 6 bedroom, 7 full and 4 half bath home located on 1 acre that is reminiscent of a luxury hotel complete with patio, pool and spa. This limestone clad home boasts unsurpassed quality construction and is accompanied with high-end interior designer appointed finishes throughout. Some of the home's highlights include: hand scraped, hand beveled hardwood floors,

Beth Wexler @properties Christie's International Real Estate

Situated on a prime half-acre lot in sought-after East Highland Park, this one-of-a-kind custom residence, completed in 2022, offers a rare combination of timeless architecture, warm contemporary design, and purposeful functionality, all executed with an uncompromising commitment to quality. While striking curb appeal sets the tone from the moment you arrive, the grand circular driveway,

Joshua Lipton Compass

This Beautifully Updated Mid Century Highlands Home Sits on a Large Wooded Lot and has a High End Kitchen with White Cabinets, Granite Countertops, Stone Subway Tile Backsplash, Stainless Appliances, Double Oven, and More. An Addition with a Spacious Mudroom and an Extra Half Bath Expands the Main Floor. There are 4 bedrooms and 2 Baths on the 2nd Floor. Other Features Include Hardwood and Stone

Janet Borden Compass

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,

Karen Biazar North Clybourn Group, Inc.

Exceptional custom-built residence completed in 2013, where timeless architecture, impeccable craftsmanship, and sophisticated design come together in one extraordinary home. A true standout feature is the sought-after first-floor primary suite, offering the comfort and convenience of main-level living, while a private elevator provides effortless access to all three levels-an exceptional amenity

Jacqueline Lotzof Compass

Dramatic Architecture in a Prime East Location! This Stunning Contemporary with a Main Floor Primary Suite sits on a Gorgeous, Professionally Landscaped Parcel of Close to an Acre with Sweeping Ravine Views. Set Far back from the Street, Offering Privacy, yet a Short Walk to Town this Exudes the Best of Everything. It Lives like a Ranch with All You Need on the Main Level, and 3 Bedrooms on the

Janet Borden Compass

Come see this bright and light 3 bdrm 2.5 bath end-unit home in Chantilly! This favorite and larger floor plan faces an interior courtyard (no road in front of your windows) with serene and lovely garden views.The entry leads to the living room, dining room and powder room. The spacious family room with wet bar, adjoins the living room, dining room and kitchen offering flexibilty and great flow.

Susan Zeller Jennings Realty,Inc.

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

Rebecca Gilberg Compass

Move right into this quality updated, solid built brick ranch. A fabulous one story alternative to condo/townhouse living set on a third of an acre, located in a private subdivision near Sunset Valley golf course and Highland Park's Hidden Creek Aqua Park. Two bedrooms and two newer bathrooms offer private spaces to the wide-open floor plan which is wonderful for entertaining. Front entrance

Susan Ringel Segal @properties Christie's International Real Estate

Welcome home to this beautifully updated 2-bedroom condominium featuring one of the most desirable views in the building. Enjoy peaceful views overlooking the expansive rear grounds with mature trees and lush green space, all backing directly to a City of Highland Park public park, creating a serene and private setting.The spacious living room and dining room flow seamlessly together, offering an

Ted Pickus @properties Christie's International Real Estate

Historic lakefront Queen Anne mansion on Lake Michigan! Set on a private 3/4 acre, surrounded on three sides by park, ravine, and Lake, adding "borrowed landscape". Premier location within the "Fort Sheridan" neighborhood of Highland Park, with parks, nearby restaurants, walking trails, beach, and many cultural activities. NuHaus kitchen overlooks Lake. Gorgeous views everywhere. Master Bedroom

Eileen Campbell Jameson Sotheby's International Realty

Sophisticated new custom built 5 bedroom, 6 full bath & 2 half bath home with guest house, patio, pool & spa located on over 3 acres. This limestone & stucco clad home w/composite terra cotta Spanish roof tiles boasts unsurpassed quality construction by Red Rock Homes & is accompanied w/high-end interior designer finishes by Ilene Chase. Some of the home's highlights include: soaring ceilings,

Beth Wexler @properties Christie's International Real Estate

Welcome to this one-of-a-kind, renovated end-unit townhome in sought-after Chantilly. Perfectly positioned overlooking Chantilly's beautifully landscaped pool, this coveted location offers a resort-like lifestyle just steps from your front door within East Highland Park Ravinia Neighborhood. Completely reimagined by its owner, a professional interior designer, the home showcases exceptional

Debbie Croft @properties Christie's International Real Estate

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

Janet Borden Compass

Get ready for resort style living with this luxurious, updated, penthouse suite in highly sought-after Northbrook Country! This stunning, 2 bedroom, 2 full bath, top floor condo has SO many features and updates for the lucky buyer to enjoy. From gleaming hardwood flooring to updated kitchen/baths to newer HVAC, this condo has been carefully designed to be both beautiful and practical. As you

Leslie Silverman @properties Christie's International Real Estate