8806 WHISPERING PINES Trail — Woodstock, IL 60098
Active
Woodstock, IL 60098

8806 WHISPERING PINES Trail

$2,200,000
4 beds · 7 baths · 8,803 sqft
Listed at $2,200,000 1 day on market $27,707/yr taxes
01About this home

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.

02Inside the home
03By the numbers
$2,200,000
List price
8,803
Square feet
4
Bedrooms
4 full / 3 half
Bathrooms
2007
Year built
33.00 ac
Lot size
4
Garage spaces
$27,707
Annual taxes
Other
Style
1
Days on market
04Features
Heating
Natural GasForced AirRadiantSep Heating Systems - 2+Indv ControlsZonedRadiant Floor
Cooling
Central AirZoned
Appliances
Double OvenMicrowaveDishwasherHigh End RefrigeratorBar FridgeWasherDryerDisposalIndoor GrillWine RefrigeratorCooktopRange HoodWater Softener OwnedGas OvenHumidifier
Parking
AsphaltGarage Door OpenerEV ReadyGarage OwnedAttachedGarage
Construction
CedarStone
Equipment
Water-Softener OwnedCentral VacuumTV-DishSecurity SystemCO DetectorsCeiling Fan(s)Sump PumpAir PurifierGeneratorMultiple Water HeatersSecurity Cameras
Sewer
Septic Tank
05Neighborhood
This home EElementary schoolHHigh school
E Elementary school
Olson Elementary School
Woodstock, IL
📍34 mi🚗89 min
M Middle school
Northwood Middle School
Woodstock, IL
H High school
Woodstock North High School
Woodstock, IL
📍4.5 mi🚗12 min
06History

Every event we have for this address, straight from the MLS.

Jun 10, 2026
Listed for saleThis listing
@properties Christie's International Real Estate
$2,200,000
Sourced from MRED. Older events appear here as our history backfill completes.
07Ask Dwello

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08See it for yourself

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09Similar homes
Listed by @properties Christie's International Real Estate · Troy Stukowski · 815-245-4882
MLS data provided through MLS GRID · MRED MLS · MLS# MRD12621391
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