Movoto Real Estate
Sold on 05/04/2026
  • Exterior
  • Entry Way
  • Living
  • Other
  • Kitchen
  • Bedroom
  • Bath
  • View/Area
  • Floorplan

23761 Winding Way, Milton, DE 19968

$975,000

Last sold 05/04/2026 after 59 Days

  • 4

    bed

  • 5

    bath

  • 8,057

    Sqft ($121/Sqft)

House not for sale

About 23761 Winding Way

Property type House
Year built 2006
HOA fee $0/month
Lot size 7.47 Acre
Movoto estimate
Parking 6 garage spaces
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!
Listed by
Listing Agent - Lee Ann Wilkinson
Listing Office - Berkshire Hathaway HomeServices PenFed Realty
Source: Bright MLS mls logo
MLS#DESU2106276 • last updated 4 weeks ago
Movoto checked Bright MLS for data 4 minutes ago
Overview
Cooling/AC Central A/C, Electric
Heating Electric, Propane - Owned
Levels/Style Contemporary
Type Residential
Status Closed
SqFt 8057
Lot Size (SqFt) 325393
Lot Size (Acres) 7.47
County Tax 251, Annually
School Tax Annually, 2228
Annual Property Tax 2479
Year Built 2006
New Construction (Y/N) N
Foreclosure (Y/N) N
Interior
Total # of Bathrooms 5
# Full Baths 5
Total # of Bedrooms 4
Basement Partial
Other Room(s) 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
Laundry Upper Floor
Appliances Cooktop, Dishwasher, Microwave, Oven - Wall, Oven/Range - Electric, Oven - Double, Refrigerator, Extra Refrigerator/Freezer, Washer, Dryer
Walls/ Ceilings 2 Story Ceilings, 9'+ Ceilings
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
Exterior
Roof Shingle
Foundation Slab
Garage Desc Garage - Front Entry, Inside Access, Oversized, Additional Storage Area
Parking Desc Asphalt Driveway, Attached Garage, Driveway, Detached Garage
# Garage Spaces 6
# Parking Spaces 16
# Attached Garage Spaces 4
# Detached Garage Spaces 2
# Driveway Spaces 10
Exterior Features Extensive Hardscape, Outbuilding(s), Play Area, Secure Storage, Underground Lawn Sprinkler
Existing Structures Above Grade, Below Grade, Guest House, Shed, Wood/Metal Shed
Amenities / Utilities
Pool Yes - Personal
Location
Subdivision NONE AVAILABLE
Water Source Well
Senior Community (Y/N) N
School District CAPE HENLOPEN
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.
Zoning AR-1
$1.02M
Range: $880K-$1.16M
Last 30 days 
  • May 2026
    mls logo MLS # DESU2106276
  • May 21, 2026 Sold
    $975,000 (-11.3%)
  • Apr 17, 2026 Pending
  • Mar 27, 2026 Active
  • Mar 6, 2026 Listed
    $1,099,500 (-8.3%)
  • Nov 2025
    mls logo MLS # DESU2091770
  • Nov 3, 2025 Price Change
    $1,199,500 (-4.0%)
  • Sep 27, 2025 Price Change
    $1,249,500 (-3.8%)
  • Sep 9, 2025 Price Change
    $1,299,500 (-3.7%)
  • Aug 26, 2025 Price Change
    $1,349,500 (-3.3%)
  • Aug 8, 2025 Listed
    $1,395,000
  • Year Property taxes Tax assessment
  • 2023
    $4,317 +3.9%
    $92,650
  • 2022
    $4,154 +4.8%
    $92,650
  • 2021
    $3,963 +0.3%
    $92,650
  • 2020
    $3,950 -0.2%
    $92,650
  • 2019
    $3,956
    $92,650
  • 23761 Winding Way
    $975K
  • 19968
    $549K -2% y/y
  • Milton
    $549K -2% y/y
No chart available
Statistics calculated by Movoto
Est. value Bed/bath Sqft mi
16718 Gravel Hill Rd, Milton, DE 19968 $361,000 3/2 1,232 0.06
23223 Neptune Rd, Milton, DE 19968 $550,000 3/— 2,043 0.06
16700 Gravel Hill Rd, Milton, DE 19968 $332,000 3/— 1,288 0.07
16684 Gravel Hill Rd, Milton, DE 19968 $457,000 3/— 1,888 0.07
16670 Gravel Hill Rd, Milton, DE 19968 $496,000 4/2 2,157 0.09
23277 Neptune Rd, Milton, DE 19968 $399,000 3/2 1,344 0.09
23185 Neptune Rd, Milton, DE 19968 $532,000 3/2 2,232 0.1
17439 Bramblewood Ln, Milton, DE 19968 $587,000 2/— 1,512 0.12

Estimated values are based on public record data and automated valuation models. Values are not guaranteed and may not reflect current market conditions.

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Source: GreatSchools.org © 2026. All rights reserved.

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