23761 Winding Way
Closed 5/4/26
Closed 5/4/26
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...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!
- Listed by Lee Ann Wilkinson • Berkshire Hathaway HomeServices PenFed RealtyP: (302)-645-6664 leeann@leeanngroup.com
Property Details for 23761 Winding Way
Tax ID Number
235-25.00-68.00
OwnershipFee Simple
Condo Coop AssociationNo
HOANo
Structure TypeDetached
StyleContemporary
Levels/Stories3.5
WaterfrontNo
LISTING UPDATED: 05/21/2026 03:39 PM
Property Details for 23761 Winding Way
| Status | Closed |
|---|---|
| MLS # | DESU2106276 |
| Days on Market | 22 |
| Taxes | $2,479 / year |
| HOA Fees | - |
| Condo/Co-op Fees | - |
| Property Type | Single Family |
| MLS Type | Residential / Fee Simple |
| Year Built | 2006 |
| Lot Size | 7.47 AC / 325,393 SF |
| County | Sussex County |
Location
Listing Courtesy of Berkshire Hathaway HomeServices PenFed Realty
Sold By Monument Sotheby's International Realty
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Building Information for 23761 Winding Way
Stories-Year Built2006Building Size-Lot Size7.47 AC / 325,393 SF
Payment Calculator
$5,065 per month
30 year fixed, 6.36% Interest
Principal and Interest
$4,859
Property Taxes
$207
HOA Dues
$0
The Payment Calculator is for illustrative purposes only.
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1Property Information for 23761 Winding Way
Location
Location
- In City Limits: No
- School District Name: CAPE HENLOPEN
- School District County ID: 300200396895
- SchoolDistrictSource: Listing Agent
- County: SUSSEX
- MLS Area: Broadkill Hundred (31003)
Waterfront / Water Access
Waterfront / Water Access
- Water View: No
- Water Access: No
- Water Oriented: No
- Navigable Water: No
- Tidal Water: No
- Riparian Rights Y/N: No
Association / Community Info
Association / Community Info
- Senior Community: No
Taxes and Assessment
Taxes and Assessment
- Tax Year: 2025
- Year Assessed: 2025
- County Tax: $251
- Clean Green Assessed: No
- Land Use Code: 1 1
- Zoning: AR-1
- Tax Lot: 85
- School Tax: $2,228
- School Tax Payment Frequency: Annually
- Automatically Update Tax Values Y/N: Yes
Rooms
Main
- # Bedrooms Count Main Level: 1
- # Bathrooms Count Main Level: 1
- # Bathrooms Full Main Level: 1
All Upper Levels
- # Bedrooms Count All Upper Levels: 3
- # Bathrooms Count All Upper Levels: 3
- # Bathrooms Full All Upper Levels: 3
Upper Level 1
- # Bedrooms Count Upper Level: 1
- # Bathrooms Count Upper Level: 2
- # Bathrooms Full Upper Level: 2
Upper Level 2
- # Bedrooms Count Upper Level: 2
- # Bathrooms Count Upper Level: 1
- # Bathrooms Full Upper Level: 1
All Lower Levels
- # Bathrooms All Lower Levels: 1
- # Bathrooms Full All Lower Levels: 1
Lower Level 1
- # Bathrooms Lower Level: 1
- # Bathrooms Full Lower Level: 1
Rooms
- Room List: Dining Room, Primary Bedroom, Bedroom 3, Bedroom 4, Kitchen, Foyer, Bedroom 1, Great Room, Laundry, Loft, Other, Solarium, Storage Room, Utility Room, Bonus Room, Primary Bathroom, Full Bath
- Stories: Lower 1, Main, Upper 1, Upper 2
Rooms Information
Room 1
- Room Type: Other
- Room Level: Lower 1
- Room Exists: Yes
- Room Features: Attached Bathroom, Flooring - Concrete, Ceiling Fan(s), Walk-In Closet(s)
Room 2
- Room Type: Bedroom 1
- Room Level: Main
- Room Exists: Yes
- Room Features: Ceiling Fan(s), Flooring - Engineered Wood
Room 3
- Room Type: Full Bath
- Room Level: Main
- Room Exists: Yes
- Room Features: Flooring - Engineered Wood
Room 4
- Room Type: Great Room
- Room Level: Main
- Room Exists: Yes
- Room Features: Balcony Access, Ceiling Fan(s), Flooring - Engineered Wood
Room 5
- Room Type: Kitchen
- Room Level: Upper 1
- Room Exists: Yes
- Room Features: Breakfast Bar, Island, Flooring - Engineered Wood, Built-Ins, Breakfast Nook, Ceiling Fan(s), Kitchen - Electric Cooking, Balcony Access
Room 6
- Room Type: Primary Bedroom
- Room Level: Upper 1
- Room Exists: Yes
- Room Features: Attached Bathroom, Ceiling Fan(s), Flooring - Engineered Wood, Balcony Access
Room 7
- Room Type: Foyer
- Room Level: Lower 1
- Room Exists: Yes
- Room Features: Flooring - Engineered Wood
Room 8
- Room Type: Storage Room
- Room Level: Lower 1
- Room Exists: Yes
Room 9
- Room Type: Utility Room
- Room Level: Lower 1
- Room Exists: Yes
Room 10
- Room Type: Solarium
- Room Level: Lower 1
- Room Exists: Yes
- Room Features: Ceiling Fan(s), Skylight(s)
Room 11
- Room Type: Primary Bathroom
- Room Level: Upper 1
- Room Exists: Yes
- Room Features: Bathroom - Walk-In Shower, Flooring - Engineered Wood
Room 12
- Room Type: Laundry
- Room Level: Upper 1
- Room Exists: Yes
- Room Features: Ceiling Fan(s), Flooring - Engineered Wood
Room 13
- Room Type: Bonus Room
- Room Level: Upper 1
- Room Exists: Yes
- Room Features: Flooring - Carpet
Room 14
- Room Type: Full Bath
- Room Level: Upper 1
- Room Exists: Yes
- Room Features: Flooring - Engineered Wood, Walk-In Closet(s), Bathroom - Walk-In Shower
Room 15
- Room Type: Dining Room
- Room Level: Upper 1
- Room Exists: Yes
- Room Features: Ceiling Fan(s), Flooring - Engineered Wood
Room 16
- Room Type: Loft
- Room Level: Upper 2
- Room Exists: Yes
- Room Features: Balcony Access, Ceiling Fan(s), Flooring - Engineered Wood
Room 17
- Room Type: Bedroom 3
- Room Level: Upper 2
- Room Exists: Yes
- Room Features: Ceiling Fan(s), Flooring - Carpet, Walk-In Closet(s)
Room 18
- Room Type: Bedroom 4
- Room Level: Upper 2
- Room Exists: Yes
- Room Features: Attached Bathroom, Ceiling Fan(s), Flooring - Carpet, Walk-In Closet(s)
Room 19
- Room Type: Full Bath
- Room Level: Upper 2
- Room Exists: Yes
- Room Features: Flooring - Carpet
Room 20
- Room Type: Storage Room
- Room Level: Main
- Room Exists: Yes
Room 21
- Room Type: Full Bath
- Room Level: Lower 1
- Room Exists: Yes
- Room Features: Flooring - Concrete, Bathroom - Walk-In Shower
Building Info
Building Info
- Total Finished SQFT: 8,057.00
- Total Finished SQFT Source: Estimated
- Tax Total Finished SQFT: 2,610.00
- Total SQFT: 8,057.00
- Total SQFT Source: Estimated
- Construction Materials: Frame, Stick Built
- Roof: Shingle
- Wall and Ceiling Types: 2 Story Ceilings, 9'+ Ceilings
- Flooring Type: Engineered Wood, Concrete, Carpet
- Basement Type: Partial
- Foundation Details: Slab
- Room and Floor: Bedrooms-Main Level-1, Bathrooms Full-Main Level-1, Bedrooms-Upper Level 1-1, Bathrooms Full-Upper Level 1-1, Bathrooms Full-Upper Level 1-2, Bathrooms Full-Lower Level 1-1, Bedrooms-Upper Level 2-1, Bedrooms-Upper Level 2-2, Bathrooms Full-Upper Level 2-1
- # Bathrooms Full: 5
- Other Structure: Guest House, Shed, Wood/Metal Shed
Lot / Land Information
Lot / Land Information
- Lot Size Source: Assessor
- Lot Size Dimensions: 225.00 x 1074.90 x 399.23 x 1035.44
- Lot Dimensions Source: Estimated
- Lot Features: Trees/Wooded, Private
- Parcel ID: 5175742
Parking
Parking
- Type Of Parking: Attached Garage, Driveway, Detached Garage
- Num of Attached Garage Spaces: 4
- Num of Detached Garage Spaces: 2
- Driveway - # of Spaces: 10
- Total Garage Spaces: 6
- Parking Features: Asphalt Driveway
- Garage Features: Garage - Front Entry, Inside Access, Oversized, Additional Storage Area
Interior Features
Interior Features
- Interior Features: Bathroom - Stall Shower, Bathroom - Walk-In Shower, Carpet, Ceiling Fan(s), Dining Area, Elevator, Kitchen - Island, Primary Bath(s), Recessed Lighting, Walk-in Closet(s), Other, Water Treat System
- Fireplace: Yes
- Fireplaces Count: 1
- Appliances: Cooktop, Dishwasher, Microwave, Oven - Wall, Oven/Range - Electric, Oven - Double, Refrigerator, Extra Refrigerator/Freezer, Washer, Dryer
- Accessibility Features: Elevator, Grab Bars Mod
- Laundry Type: Upper Floor
Exterior Features
Exterior Features
- Exterior Features: Extensive Hardscape, Outbuilding(s), Play Area, Secure Storage, Underground Lawn Sprinkler
- Outdoor Living Structures: Balconies- Multiple, Patio(s)
- Pool: Yes - Personal
- Personal Pool Features: Indoor, Pool/Spa Combo
Utilities
Utilities
- Heating: Yes
- Cooling Type: Central A/C
- Cooling Fuel: Electric
- Heating Type: Heat Pump - Gas BackUp, Wall Unit, Zoned
- Heating Fuel: Electric, Propane - Owned
- Hot Water: Propane
- Water Source: Well
- Sewer Septic: Capping Fill, Low Pressure Pipe (LPP)
Confidential Data
Listing Office
- List Agent AOR: Sussex County Association of REALTORS (DE)
Property History for 23761 Winding Way
| Date | Event & Source | Price | Appreciation |
|---|---|---|---|
| May 4, 2026 | Closed BRIGHT #DESU2106276 | $975,000 | — |
| Mar 25, 2026 | Pending BRIGHT #DESU2106276 | — | |
| Mar 25, 2026 | Active Under Contract BRIGHT #DESU2106276 | — | |
| Mar 6, 2026 | Listed (Active) BRIGHT #DESU2106276 | $1,099,500 | — |
| Dec 31, 2025 | Withdrawn BRIGHT #DESU2091770 | — | |
| Nov 3, 2025 | Price Change BRIGHT #DESU2091770 | $1,199,500 | — |
| Sep 27, 2025 | Price Change BRIGHT #DESU2091770 | $1,249,500 | — |
| Sep 9, 2025 | Price Change BRIGHT #DESU2091770 | $1,299,500 | — |
| Aug 26, 2025 | Price Change BRIGHT #DESU2091770 | $1,349,500 | — |
| Aug 8, 2025 | Listed (Active) BRIGHT #DESU2091770 | $1,395,000 | — |
| Date | Event & Source | Price |
|---|---|---|
| 05/04/2026 | Closed BRIGHT #DESU2106276 | $975,000 |
| 03/25/2026 | Pending BRIGHT #DESU2106276 | — |
| 03/25/2026 | Active Under Contract BRIGHT #DESU2106276 | — |
| 03/06/2026 | Listed (Active) BRIGHT #DESU2106276 | $1,099,500 |
| 12/31/2025 | Withdrawn BRIGHT #DESU2091770 | — |
| 11/03/2025 | Price Change BRIGHT #DESU2091770 | $1,199,500 |
| 09/27/2025 | Price Change BRIGHT #DESU2091770 | $1,249,500 |
| 09/09/2025 | Price Change BRIGHT #DESU2091770 | $1,299,500 |
| 08/26/2025 | Price Change BRIGHT #DESU2091770 | $1,349,500 |
| 08/08/2025 | Listed (Active) BRIGHT #DESU2091770 | $1,395,000 |
For completeness, we often displays two records for one sale: the MLS record and the public record.
Public Records for 23761 Winding Way
Taxable ValueLand$3,750Additions$88,900Total$92,650
Tax Record2025$2,229 ($186 / month)
Home Facts
Beds4Total Finished SqFt5,220 SqFtAbove Grade Finished SqFt5,220 SqFtStories2Lot Size284,621 SqFtStyleSingle Family ResidenceYear Built2006ZoningAR1CountySUSSEXAPN235-25.00-68.00Fireplace TypeHas Fireplace
Schools near 23761 Winding Way
This home is within Cape Henlopen School District.
Rating | School | Type | Grades | Distance |
|---|---|---|---|---|
| Public - | K to 5 | |||
| Public - | 6 to 8 | |||
| Public - | 9 to 12 | |||
| Public - | 6 to 8 |
Rating | School | Distance |
|---|---|---|
Milton Elementary School PublicK to 5 | ||
Beacon Middle School Public6 to 8 | ||
Cape Henlopen High School Public9 to 12 | ||
Frederick D Thomas Middle School Public6 to 8 |
School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.
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Listing Courtesy of Berkshire Hathaway HomeServices PenFed Realty
Based on information from one of the following Multiple Listing Services: BRIGHT, Greater LeHigh Valley Regional MLS, Greator Scranton Board of REALTORS® and Pocono Mountains Association of REALTORS®. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by BRIGHT, Greater LeHigh Valley Regional MLS, Greator Scranton Board of REALTORS® and Pocono Mountains Association of REALTORS® is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.