The North Shore has some of the most exquisite and unique upper bracket homes in the Chicago area, with price tags to match. This year's top ten most expensive homes for sale range in price from $7,950,000 to $14,855,000, with a median price of $9,600,000.

Seven of them are lakefront homes and one is new construction. Four are located in Winnetka, three in Highland Park, two in Lake Forest and one in Wilmette.

All but one of these properties were on the market this time last year. Most have had significant price reductions, so if you are looking for "bargain" luxury real estate, there are some great opportunities available.

Search all upper bracket homes for sale on Chicago's North Shore

 Here's our 2017 top ten list, from lowest to highest price:

#10. 1869 Crescent Court, Highland Park  -   $7,950,000

1869 Crescent Ct., Highland Park

This contemporary home designed by Tony Grunfeld sits on 3.8 acres overlooking Lake Michigan. The 16 room house goes on forever, with room after room of huge windows and spectacular views. Even if you don't like modern architecture, you can't deny that the grounds are incredible. The expansive tableland allows for a large lawn, a pool, lighted tennis/sports court and gardens, with 408 feet of private beach at the bottom of the bluff. You can see more photos and info here.

The price has been reduced almost $5,000,000 since it first came on the market last year, so it does represent a bargain, especially since the lot is sub-dividable into at least two parcels. You can defray some of your acquisition costs (and the hefty property tax bill) by selling part of the property and still keeping the house and a nice chunk of beachfront.

Foyer 1869 Crescent Ct. Highland Park

 

#9. 1601 Conway Road, Lake Forest       -     $8,000,000

If a country estate is what you're after, this property fills the bill. The lovely Topsfield Farm was built in 1930 and sits on 27.5 acres of pasture and conserved land on the edge of the Conway Farms Country Club. It has only had four owners (hence the incredibly low property taxes of $37K) and each has updated and expanded the home, as well as adding amenities like a 4-stall barn, indoor and outdoor pool, tennis court and caretaker's cottage.

1601 Conway Rd., Lake Forest

 fields at 1601 Conway Rd.

1601 Conway Rd. stable

See more photos and information about Topsfield Farm here.

 #8. 15 Linden Avenue, Wilmette      -     $8,499,000

15 Linden Avenue Wilmette IL 60091

Craving the lakefront lifestyle but want to be close to the city? Located in the southeastern part of Wilmette, this home is just a quick (ok, 30 minutes) drive straight down Sheridan Road to the city. Imagine being able to leave work and be out on your boat in less than an hour!

The 15 room home sits on a secluded .93 acre lot and has all the amenities you'd expect from an upper bracket property: chef's kitchen, luxurious master suite, lower level theater and exercise room, 3rd floor retreat with office, elevator, sauna and separate in-law suite. Virtually every room has a sweeping view of Lake Michigan. But what makes this home special is the property. The expansive tableland, lush landscaping, patios and stone paths leading down the the lake and the boat dock make this an idyllic setting.

This property started at $10,900,000 a year ago and has been reduced $2.4M (22%).

15 Linden Ave. from lake side

master bedroom 15 Linden Ave., Wilmette

Imagine waking up to this view!

See more photos and information about 15 Linden Avenue here.

#7. 2445 Woodbridge Lane, Highland Park   -   $8,900,000

2445 Woodbridge Lane, Highland Park, IL

Built in 1928, this home has the steep slate roof, half timber facade and turret characteristic of French Normandy architecture. Perched on a bluff, the house is designed to take full advantage of its location, and almost every room has a view of the lake. The wide lawn features a pool, and the private beach at the foot of the bluff is spectacular.

2445 Woodbridge view of Lake Michigan

This property has been reduced $900K from the original list price of $9,800,000. One of the positives of this home is its relatively low (for a lakefront home) taxes of $76,663/year.

See more photos and information about 2445 Woodbridge Lane here.

 #6. 405 N. Mayflower Road, Lake Forest  -  $9,450,000

405 N. Mayflower Rd., Lake Forest, IL

The historic Schweppe Estate is one of the most architecturally significant homes on the North Shore. Built in 1917, it has 28 rooms and 12 bedrooms, all crafted with incredible finishes and attention to detail: plaster-relief ceilings, carved wood paneling, beveled mirrors, leaded arched windows and 11 marble and limestone fireplaces. Upon entering the home you feel as if you've been transported to one of the Royals' country estates in Great Britain.  In fact, the Duke and Duchess of Windsor were once guests here.

The house has an interesting history. After sitting vacant for over forty years it was extensively restored during the 1980's by over 70 European craftsmen.

If the house is magnificent, the property is more magnificent still. Five and a half wooded acres and 450 feet of lake frontage with a private sandy beach make this one of the most sublime pieces of real estate in the area.

On and off the market for several years the price of this estate has been reduced dramatically, down 47% from the original price of $18,000,000.

living room 405 N. Mayflower

Schweppe Estate dining room

See more photos and information about the Schweppe Estate here.

 #5. 1215 Whitebridge Hill Road, Winnetka   -  $9,750,0001215 Whitebridge Hill Rd., Winnetka, IL

One of the newer homes in our top ten, this 15,000 square foot brick and limestone villa was built in 2001. While perhaps not as timelessly elegant as some of the others, it does offer the total menu of luxury amenities: 12-seat theater, spa with steam and massage room, indoor pool, six fireplaces, grand foyer with double floating staircase and wood-carved bar.

One of the smaller properties (.89 acre), it nevertheless has 150 feet of private beach.

It's been on the market since February of 2016 and has not had a price reduction.

Bridal staircase 1215 Whitebridge Hill Rd Winnetka

See more photos and information about 1215 Whitebridge Hill Road here.

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#4. 68 Locust Road, Winnetka      -      $11,900,000

68 Locust Rd., Winnetka, IL

If Donald Trump lived on the North Shore, this is where he would live. Every room of this 26,500 square foot house is a study in over-the-top opulence. It cost $36,000,000 and took four years to build. Just three years after its completion, it was listed for sale.

Designed by Richard Landry ("architect of the stars", including Eddie Murphy, Rod Stewart, Wayne Gretzky and Tom Brady), this 2.25 acre estate has every conceivable bell and whistle, and then some: wine cellar with tasting room, a hotel-style spa and salon, De Giulio kitchen, theater, state of the art security system, 10-car heated garage, elevator, pool, covered loggia, two-story rotunda, 11 fireplaces and even a gift-wrapping room!

Master bedroom 68 Locust Rd Winnetka

wine cellar 68 Locust Rd Winnetka

It has been on the market for seven years and is now on its fifth real estate agent. Originally priced at $28,000,000, it has been reduced a whopping 57% ($16.1M). Why hasn't it sold before now? For one thing, it's not on Lake Michigan, but it's taxed as though it were. At a jaw-dropping $207,733 per year it wins the award for highest property taxes among our top ten priciest properties.

See more photos and information about 68 Locust Road here.

 #3. 735 Sheridan Road, Winnetka     -    $12,900,000

735 Sheridan aerial view

The oldest of our top ten, this neoclassical style beauty dates back to 1905. Set on almost three acres between Sheridan Road and Lake Michigan, the home has 17 rooms and 7 bedrooms, as well as a matching coach house. Beautiful terraces lead to the pool with its four cabanas and then down to the sandy beach.

This is the latest of the top ten to hit the market (in February 2017), and one of two listings that has not had a price reduction.

 

735 Sheridan Rd., Winnetka, IL 60093

735 Sheridan great room

pool 735 Sheridan Rd Winnetka IL 60093

See more photos and information about 735 Sheridan Road here.

 #2. 1035 Sheridan Road, Winnetka    -    $13,700,000

1035 Sheridan Rd., Winnetka IL 60093

Built by Heritage Luxury Homes, this new construction home has a total of 19,000 square feet of living space (including the lower level) and sits on 1.3 acres of lakefront property with 130 feet of private beachfront. True to the Heritage "formula" the 17 room home offers everything a luxury buyer is looking for: lavish entertaining space, gourmet kitchen, elevator, oversized pool, fire pit, media room, wine cellar, exercise room, sport court, two wet bars and even a golf simulator.

See more photos and information about 1035 Sheridan Road here.

#1. 2700 Point Road, Highland Park    -    $14,855,000

 Are you looking for a private estate of 7+ acres with a 9 bedroom contemporary home, regulation-sized basketball court, circular infinity pool, putting green, tennis court, cigar room and every other conceivable amenity? Then this might be for you.Michael Jordan's house 2700 Point Ln Highland Park IL

This is Michael Jordan's home, custom-built by Jordan during his Chicago Bulls heyday. It is one-of-a-kind, designed specifically for its owner, which probably explains (along with the price tag) why it has been on the market for over five years. It was originally listed for $29,000,000 back in 2012 and has been slashed by almost 50% since then, so some would consider it an incredible bargain at this point.

Micahel Jordan's house at 2700 Point Lane
See more photos and information about Michael Jordan's house here.

Are you looking for a special home on Chicago's North Shore? I can help! Give me a call at 847-687-595 or Contact Us . We can discuss your needs and priorities and I will help you find that perfect property. I am familiar with all of the luxury listings in the area, including those that are "exempt" (not on the MLS).

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