Date
Details
Price
Change
Source
3/06/2026
Listed
$1,099,500
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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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!
Full Property Details
Full Property Details for 23761 Winding Wy
General
- Price: $1,099,500
- Taxes: $2,479 (2025)
- Status: Active
- Type: Single Family
- Source: BrightMLSMidAtlantic
- MLS ID: DESU2106276
- Updated: 3/8/2026
- Added to Site: 3 day(s) ago
Interior
- Rooms/Areas: 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
- 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
- Number of Fireplaces: 1
- Appliances: Cooktop, Dishwasher, Microwave, Oven - Wall, Oven/Range - Electric, Oven - Double, Refrigerator, Extra Refrigerator/Freezer, Washer, Dryer
- Flooring: Engineered Wood, Concrete, Carpet
Rooms
Bathrooms
- Total Bathrooms: 5
- Full Bathrooms: 5
- Upper 2 - Full Baths: 1
- Upper Floor Baths: 3
- Upper - Full Baths: 3
- Main Floor Baths: 1
- Main - Full Baths: 1
- Lower Floor Baths: 1
- Lower - Full Baths: 1
Bedrooms
- Total Bedrooms: 4
- Bedrooms Upper: 3
- Bedrooms-Up2: 2
- Bedrooms Main & Up: 1
Other Rooms
- Laundry: Upper Floor
Additional Information
- Pool: Yes
- Private Pool: Yes
- Pool Description: Indoor, Pool/Spa Combo
Exterior
- Exterior Features: Extensive Hardscape, Outbuilding(s), Play Area, Secure Storage, Underground Lawn Sprinkler
- Porch/Patio/Deck: Balconies- Multiple, Patio(s)
Parking
- Garage: Yes
- Garage Spaces: 6
- Total Spaces: 16
- Parking Features: Asphalt Driveway
- Parking Type: Attached Garage, Driveway, Detached Garage
- Garage Description: Garage - Front Entry, Inside Access, Oversized, Additional Storage Area
Location
- Area: Broadkill Hundred (31003)
- County: SUSSEX
- Driving Directions: From Rt 9, turn onto Prettyman Rd, then right onto Gravel Hill Rd. From there, turn left onto Neptune rd, property will be on the right.
School Information
- School District: Cape Henlopen
Heating & Cooling
- Central air: Yes
- Cooling Type: Central A/C
- Cooling Fuel: Electric
- Heating Type: Heat Pump - Gas BackUp, Wall Unit, Zoned
- Heating Fuel: Electric, Propane - Owned
- Water Heater: Propane
Utilities
- Sewer: Capping Fill, Low Pressure Pipe (LPP)
- Water: Well
Structural Information
- Architectural Style: Contemporary
- Structure Type: Detached
- Construction: Frame, Stick Built
- Basement: Yes
- Basement Desc.: Partial
- Foundation: Slab
- Roof: Shingle
- Walls/Ceilings: 2 Story Ceilings, 9'+ Ceilings
- Stories Description: Lower 1, Main, Upper 1, Upper 2
- Square Feet: 8,057
- Sq. Ft. Source: Estimated
- Living Area: 8,057 Sq. Ft.
- Finished Above Grnd: 8,057 Sq. Ft.
- Year Built: 2006
- Year Built Source: Assessor
Unit Information
Unit 1
- Bathrooms-Lower: 1
Additional Structures
- Other Structures: Guest House, Shed, Wood/Metal Shed
Lot Features
- Property View: Garden/Lawn, Trees/Woods
- Lot Size (Acres): 7.47
- Lot Size (Sq. Ft.): 325,393
- Lot Size Source: Assessor
- Lot Dimensions: 225.00 x 1074.90 x 399.23 x 1035.44
- Zoning: AR-1
- Lot Description: Trees/Wooded, Private
Financial Considerations
- Price Per Sq. Ft.: $136.47
- Assessment Year: 2025
- School Tax: $2,228
- County Tax: $251
- County Tax Freq: Annually
- Tax Amount: $2,479
- Tax Year: 2025
- Tax Total Finished Sq. Ft.: 2610
Disclosures and Reports
- Ownership: Fee Simple
- Lot Number: 85
Listed by Berkshire Hathaway HomeServices PenFed Realty, Lee Ann Wilkinson
We Value Your Privacy
We Value Your Privacy
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Listing agent
— 23761 Winding Wy —
Lee Ann Wilkinson
Berkshire Hathaway HomeServices PenFed Realty
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 23761 Winding Wy
School District:Cape Henlopen School District
| Name | Grades | Distance |
|---|---|---|
H. O. Brittingham Elementary School 402 Mulberry Street, Milton, DE 19968 | PK-5 | 2.5 mi |
Mariner Middle School 16391 Harbeson Road, Milton, DE 19968 | 5-8 | 1.7 mi |
Cape Henlopen High School 1250 Kings Highway, Lewes, DE 19958 | 8-12 | 10.1 mi |
Disclaimer:
School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 23761 Winding Wy
Tax History
Tax History for 23761 Winding Wy
Year
Property Taxes
Change
Tax Assessment
Change
2025
$2,229
-48%
$92,650
—
2023
$4,313
4%
$92,650
—
2022
$4,154
5%
$92,650
—
2021
$3,963
—
$92,650
—
2020
$3,950
—
$92,650
—
2019
$3,956
8%
$92,650
—
2018
$3,669
5%
$92,650
—
2017
$3,496
9%
$92,650
—
2016
$3,201
5%
$92,650
—
2015
$3,036
1%
$92,650
—
2014
$3,010
3%
$92,650
—
2013
$2,911
—
$92,650
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 23761 Winding Wy
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23761 Winding Way, Milton, DE 19968 (MLS# DESU2106276) is a Single Family property with 4 bedrooms and 5 full bathrooms. 23761 Winding Way is currently listed for $1,099,500 and was received on March 06, 2026. Want to learn more about 23761 Winding Way? Do you have questions about finding other Single Family real estate for sale in Milton? You can browse all Milton real estate or contact a Coldwell Banker agent to request more information.