4
Beds :
5
Baths :
8,057
Square feet :
7.47
Acres :
23761 Winding Way
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!
Features of 23761 Winding Way
| MLS® # | DESU2106276 |
|---|---|
| Price | $975,000 |
| Bedrooms | 4 |
| Bathrooms | 5.00 |
| Full Baths | 5 |
| Square Footage | 8,057 |
| Acres | 7.47 |
| Year Built | 2006 |
| Type | Single Family |
| Sub-Type | Detached |
| Style | Contemporary |
| Status | Closed |
Community Information
| Address | 23761 Winding Way |
|---|---|
| Area | Broadkill Hundred |
| Subdivision | NONE AVAILABLE |
| City | MILTON |
| County | SUSSEX-DE |
| State | DE |
| Zip Code | 19968 |
| Within City Limits | No |
| Sussex Delaware Quadrant | Between Rt 1 & 113 |
Amenities
| Amenities | Bathroom - Stall Shower, Bathroom - Walk-In Shower, Carpet, Ceiling Fan(s), Elevator, Primary Bath(s), Recessed Lighting, Walk-in Closet(s), Water Treat System |
|---|---|
| Parking | Asphalt Driveway |
| # of Garages | 6 |
| Garages | Garage - Front Entry, Inside Access, Oversized, Additional Storage Area |
| View | Garden/Lawn, Trees/Woods |
| Is Waterfront | No |
| Has Pool | Yes |
| Pool | Indoor, Pool/Spa Combo |
Interior
| Appliances | Cooktop, Dishwasher, Microwave, Oven - Wall, Oven/Range - Electric, Oven - Double, Refrigerator, Extra Refrigerator/Freezer, Washer, Dryer |
|---|---|
| Heating | Heat Pump - Gas BackUp, Wall Unit, Zoned |
| Cooling | Central A/C |
| Fireplace | Yes |
| # of Fireplaces | 1 |
| Stories | 3.5 |
| Has Basement | Yes |
| Basement | Partial |
Exterior
| Exterior | Frame |
|---|---|
| Exterior Features | Extensive Hardscape,Outbuilding(s),Play Area,Secure Storage,Underground Lawn Sprinkler,Balconies- Multiple,Patio(s),Indoor,Pool/Spa Combo |
| Lot Description | Trees/Wooded, Private |
| Roof | Shingle |
| Construction | Frame, Stick Built |
| Foundation | Slab |
School Information
| District | CAPE HENLOPEN |
|---|
Additional Information
| Date Listed | March 6th, 2026 |
|---|---|
| Days on Market | 22 |
| Zoning | AR-1 |
| Foreclosure | No |
| Short Sale | No |
| RE / Bank Owned | No |
Listing Details
| Office | Berkshire Hathaway HomeServices PenFed Realty |
|---|
