$2,200,000
4
beds
4
baths
3
half baths
8,803
square ft

8806 Whispering Pines Trail
Woodstock, Illinois 60098

Coming Soon / MLS #12621391 / Single Family / Woodstock
Listing information updated 6/6/2026 at 11:43pm
Only once in a blue moon does a luxury property come to market that delivers both exceptional interior design and functionality along with extraordinary natural elements that together create the complete home, retreat, and investment package. Welcome to Whispering Pines, a magnificent 2007 custom-designed luxury residence offering 8,800 square feet on a breathtaking 33-acre sanctuary. This private retreat features an aerated and naturally filtered swimming pond with waterfall and beach, professionally landscaped perennial gardens, extensive wooded trails, and a towering pine forest. Located on the edge of Bull Valley just off the prestigious Valley Hill corridor and adjacent to IDNR protected lands, this expansive 1.5-story ranch-style home with walkout lower level offers tranquil natural views from nearly every room. Highlights include a main-level primary suite with fireplace and walkout terrace, luxurious primary bath, executive office, and a stunning two-story great room with beamed ceiling, oak hardwood floors, custom rail doors, stone fireplace, and dramatic floor-to-ceiling windows. The chef's kitchen is perfectly suited for entertaining with an expansive wet island, high-end appliances, walk-through pantry, and separate wet butler's pantry. Additional main-level features include a remarkable three-season room with skylights and grilling station, a study/sun room, and a spacious laundry room, all enjoying splendid natural views. The upper level offers two well-appointed bedroom suites with impressive exterior views plus unfinished attic space for future expansion. The walk-out lower level with radiant heated floors throughout features convenient dual staircases, a family room with fireplace, game room, generous guest suite, sauna, cold plunge tub, library, and much more. Additional highlights include a spacious four-car garage with new epoxy flooring and 240-volt EV connections, solar panel array, backup generator, hot tub with deck, and garden shed. Over $900,000 in thoughtful improvements have been invested over the last nine years. Nearly half of the contiguous acreage, located away from the home, is already subdivided into 3 to 3.5-acre parcels, offering profitable future divestment opportunities, while the mature pine woodlands can be retained for maximum privacy. Just 15 minutes to downtown Crystal Lake or Historic Woodstock Square and 30 minutes to Lake Geneva, this unique haven represents the total package for the most discerning luxury buyer seeking ultimate design, comfort, and privacy.

Listing Office: @PROPERTIES

Listing Office Phone: 847.957.6500

Disclaimer: The data relating to real estate for sale on this website comes courtesy of Midwest Real Estate Data, LLC as distributed by MLS GRID. Real estate listings held by brokerage firms other than @properties are marked with the Broker Reciprocity thumbnail logo and detailed information about them includes the name of the listing brokers. Properties displayed may be listed or sold by various participants in the MLS. Based on information submitted to the MLS GRID as of 6/6/2026 at 11:43pm. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Some listings have been excluded from this website.


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8806 Whispering Pines Trail, Woodstock, IL 60098 is a single family home currently listed at $2,200,000. 8806 Whispering Pines Trail features 4 Beds, 4 Baths, 3 Half Baths. This single family home has been listed on @properties Christie's International Real Estate since April 23rd, 2026. Nearby schools include Olson Elementary School, Northwood Middle School, and Woodstock North High School.