23761 WINDING WAY, Milton, DE 19968

• 4 beds |
• 5 baths |
• 8,057 sqft

Property Description

THE ULTIMATE COASTAL SANCTUARY! Experience this tranquil forest estate on this lovingly maintained 7.47-acre estate bordering the majestic Redden Forest. This one-of-a-kind architectural masterpiece offers a rare blend of total privacy and prime location, creating a park-like atmosphere that remains a cool summer oasis and a sun-drenched winter retreat. The expansive 8,057-square-foot custom-built main residence defines grand-scale living across four meticulously planned levels, all easily accessible via a private residential elevator. At the heart of the home, a breathtaking two-story great room features walls of glass that frame panoramic forest views and fill the open-concept floor plan with dappled sunlight. The chef’s kitchen is a model of functional elegance, boasting soft-close cabinetry and abundant storage, while a signature spiral staircase leads to a third-floor study nestled high within the tree canopy for the ultimate peaceful escape. Luxury amenities abound, including a spectacular indoor spa wing with vaulted ceilings - maintained by a premium Desert Aire climate system - and an adjoining greenhouse for the botanical enthusiast. Outdoor living is equally refined, featuring a stone path that leads to a custom fire pit with circular stone seating, perfect for starlit gatherings. For the hobbyist or traveler, the oversized three-vehicle garage includes a specialized bay with a 20-foot door to accommodate a large RV or boat. Adding to the estate's versatility is a charming 532-square-foot detached guest cottage, complete with a kitchenette, full bath, and sunroom; ideal for a studio, home office, or extended family. Perfectly positioned just 30 minutes from the Rehoboth Beach boardwalk and Cape Henlopen State Park, this estate offers the best of both worlds: nature’s tranquility and vibrant coastal convenience. Bring your vision to this incredible property and create your personal legacy retreat. Schedule your private tour today!

Listing Status:

Pending

Data Last Updated:

May 20, 2026 at 9:20PM

Listing Office:

Berkshire Hathaway HomeServices PenFed Realty : 3026456661

Listing Agent:

Lee Ann Wilkinson : 3026456664

MLS ID:

DESU2106276

Interior

• General: Bathroom - Stall ShowerBathroom - Walk-In ShowerCarpetCeiling Fan(s)Dining AreaElevatorKitchen - IslandPrimary Bath(s)Recessed LightingWalk-in Closet(s)OtherWater Treat System
• Rooms: Dining RoomPrimary BedroomBedroom 3Bedroom 4KitchenFoyerBedroom 1Great RoomLaundryLoftOtherSolariumStorage RoomUtility RoomBonus RoomPrimary BathroomFull Bath
• Appliances: CooktopDishwasherMicrowaveOven - WallOven/Range - ElectricOven - DoubleRefrigeratorExtra Refrigerator/FreezerWasherDryer
• Laundry: Upper Floor
• Basement: Partial
• Flooring: Engineered woodConcreteCarpet
• A/C: Central A/C
• Heating: Heat Pump - Gas BackUpWall UnitZonedElectricPropane - Owned
• Fireplace: FireplaceFireplaces: 1
• Disability Feature: ElevatorGrab Bars Mod

Exterior

• General: Extensive HardscapeOutbuilding(s)Play AreaSecure StorageUnderground Lawn SprinklerAbove GradeBelow Grade
• Style: Contemporary
• Other Structures: Balconies- MultiplePatio
• Pool: IndoorPool spa combo
• Parking: Asphalt Driveway

Construction

• Roofing: Shingle
• General: FrameStick Built3.5Slab

Location

• Originating MLS: BRIGHT_MAIN
• School District: CAPE HENLOPEN
• County: SUSSEX-DE

Lot

• Zoning: AR-1235-25.00-68.00
• View: Garden/LawnTrees/Woods

Utilities

• Water: Well
• Sewer: Capping FillLow Pressure Pipe (LPP)

Financial

• Source: BRIGHT_MAIN