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!
Sold for $975,000
$975,000
23761 Winding Way, Milton, DE 19968
4beds
8,057sqft
Single Family Residence
Built in 2006
7.47 Acres Lot
$974,100 Zestimate®
$121/sqft
$3,651 Estimated rent
Home value
$974,100
$925,000 - $1.02M
$3,651/mo
Zestimate® history
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Zillow last checked:
Listing updated:
Listed by:
Lee Ann Wilkinson 302-645-6664,
Berkshire Hathaway HomeServices PenFed Realty,
Listing Team: The Lee Ann Wilkinson Group
Bought with:
PATRICIA COLUZZI, RS-0022283
Monument Sotheby's International Realty
Source: Bright MLS,MLS#: DESU2106276
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 5
- Full bathrooms: 5
- Main level bathrooms: 1
- Main level bedrooms: 1
Rooms
- Room types: 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
Primary bedroom
- Features: Attached Bathroom, Ceiling Fan(s), Flooring - Engineered Wood, Balcony Access
- Level: Upper
Bedroom 1
- Features: Ceiling Fan(s), Flooring - Engineered Wood
- Level: Main
Bedroom 3
- Features: Ceiling Fan(s), Flooring - Carpet, Walk-In Closet(s)
- Level: Upper
Bedroom 4
- Features: Attached Bathroom, Ceiling Fan(s), Flooring - Carpet, Walk-In Closet(s)
- Level: Upper
Primary bathroom
- Features: Bathroom - Walk-In Shower, Flooring - Engineered Wood
- Level: Upper
Bonus room
- Features: Flooring - Carpet
- Level: Upper
Dining room
- Features: Ceiling Fan(s), Flooring - Engineered Wood
- Level: Upper
Foyer
- Features: Flooring - Engineered Wood
- Level: Lower
Other
- Features: Flooring - Engineered Wood
- Level: Main
Other
- Features: Flooring - Engineered Wood, Walk-In Closet(s), Bathroom - Walk-In Shower
- Level: Upper
Other
- Features: Flooring - Carpet
- Level: Upper
Other
- Features: Flooring - Concrete, Bathroom - Walk-In Shower
- Level: Lower
Great room
- Features: Balcony Access, Ceiling Fan(s), Flooring - Engineered Wood
- Level: Main
Kitchen
- Features: Breakfast Bar, Kitchen Island, Flooring - Engineered Wood, Built-in Features, Breakfast Nook, Ceiling Fan(s), Kitchen - Electric Cooking, Balcony Access
- Level: Upper
Laundry
- Features: Ceiling Fan(s), Flooring - Engineered Wood
- Level: Upper
Loft
- Features: Balcony Access, Ceiling Fan(s), Flooring - Engineered Wood
- Level: Upper
Other
- Features: Attached Bathroom, Flooring - Concrete, Ceiling Fan(s), Walk-In Closet(s)
- Level: Lower
Other
- Features: Ceiling Fan(s), Skylight(s)
- Level: Lower
Storage room
- Level: Lower
Storage room
- Level: Main
Utility room
- Level: Lower
Heating
- Heat Pump, Wall Unit, Zoned, Electric, Propane
Cooling
- Central Air, Electric
Appliances
- Included: Cooktop, Dishwasher, Microwave, Oven, Oven/Range - Electric, Double Oven, Refrigerator, Extra Refrigerator/Freezer, Washer, Dryer, Water Treat System, Water Heater
- Laundry: Upper Level, Laundry Room
Features
- Bathroom - Stall Shower, Bathroom - Walk-In Shower, Ceiling Fan(s), Dining Area, Elevator, Kitchen Island, Primary Bath(s), Recessed Lighting, Walk-In Closet(s), Other, 2 Story Ceilings, 9'+ Ceilings
- Flooring: Engineered Wood, Concrete, Carpet
- Basement: Partial
- Number of fireplaces: 1
Interior area
- Total structure area: 8,057
- Total interior livable area: 8,057 sqft
- Finished area above ground: 8,057
- Finished area below ground: 0
Property
Parking
- Total spaces: 16
- Parking features: Garage Faces Front, Inside Entrance, Oversized, Storage, Asphalt, Attached, Driveway, Detached
- Attached garage spaces: 6
- Uncovered spaces: 10
Accessibility
- Accessibility features: Accessible Elevator Installed, Grip-Accessible Features
Features
- Levels: Three and One Half
- Stories: 3.5
- Patio & porch: Patio
- Exterior features: Extensive Hardscape, Play Area, Storage, Underground Lawn Sprinkler, Balcony
- Has private pool: Yes
- Pool features: Indoor, Pool/Spa Combo, Private
- Has view: Yes
- View description: Garden, Trees/Woods
Lot
- Size: 7.47 Acres
- Dimensions: 225.00 x 1074.90 x 399.23 x 1035.44
- Features: Wooded, Private
Details
- Additional structures: Above Grade, Below Grade, Outbuilding
- Parcel number: 23525.0068.00
- Zoning: AR-1
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Contemporary
- Property subtype: Single Family Residence
Materials
- Frame, Stick Built
- Foundation: Slab
- Roof: Shingle
Condition
- New construction: No
- Year built: 2006
Utilities & green energy
- Sewer: Capping Fill, Low Pressure Pipe (LPP)
- Water: Well
Community & HOA
Community
- Subdivision: None Available
HOA
- Has HOA: No
Location
- Region: Milton
Financial & listing details
- Price per square foot: $121/sqft
- Tax assessed value: $1,173,900
- Annual tax amount: $2,479
- Date on market: 3/6/2026
- Listing agreement: Exclusive Right To Sell
- Listing terms: Cash,Conventional
- Ownership: Fee Simple
Price history
| Date | Event | Price |
|---|---|---|
| 6/15/2026 | Listing removed | $1,875 |
Source: Zillow Rentals Report a problem | ||
| 6/9/2026 | Listed for rent | $1,875 |
Source: Zillow Rentals Report a problem | ||
| 5/4/2026 | Sold | $975,000-11.3%$121/sqft |
Source:  Bright MLS #DESU2106276 Report a problem | ||
| 4/17/2026 | Pending sale | $1,099,500$136/sqft |
Source: Bright MLS #DESU2106276 Report a problem | ||
| 3/27/2026 | Contingent | $1,099,500$136/sqft |
Source: Bright MLS #DESU2106276 Report a problem | ||
| 3/6/2026 | Listed for sale | $1,099,500-8.3%$136/sqft |
Source: Bright MLS #DESU2106276 Report a problem | ||
| 12/31/2025 | Listing removed | $1,199,500$149/sqft |
Source: Bright MLS #DESU2091770 Report a problem | ||
| 11/3/2025 | Price change | $1,199,500-4%$149/sqft |
Source: Bright MLS #DESU2091770 Report a problem | ||
| 9/27/2025 | Price change | $1,249,500-3.8%$155/sqft |
Source: Bright MLS #DESU2091770 Report a problem | ||
| 9/9/2025 | Price change | $1,299,500-3.7%$161/sqft |
Source: Bright MLS #DESU2091770 Report a problem | ||
| 8/26/2025 | Price change | $1,349,500-3.3%$167/sqft |
Source: Bright MLS #DESU2091770 Report a problem | ||
| 8/8/2025 | Listed for sale | $1,395,000$173/sqft |
Source: Bright MLS #DESU2091770 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $2,229 -48.4% | $586,950 +533.5% |
| 2024 | $4,317 +0.1% | $92,650 |
| 2023 | $4,313 +3.8% | $92,650 |
| 2022 | $4,154 +4.8% | $92,650 |
| 2021 | $3,963 +0.3% | $92,650 |
| 2020 | $3,950 | $92,650 |
| 2019 | $3,950 -0.2% | $92,650 |
| 2018 | $3,956 +1.5% | $92,650 |
| 2017 | $3,896 +21.7% | $92,650 |
| 2016 | $3,201 +5.4% | $92,650 |
| 2015 | $3,036 +0.9% | $92,650 |
| 2014 | $3,010 +3.4% | $92,650 |
| 2013 | $2,911 +0.4% | $92,650 |
| 2012 | $2,898 +14% | $92,650 |
| 2011 | $2,544 | $92,650 |
| 2010 | $2,544 -3.5% | $92,650 |
| 2009 | $2,636 | $92,650 |
| 2008 | -- | -- |
| 2007 | -- | -- |
| 2006 | -- | -- |
| 2005 | -- | -- |
| 2004 | -- | -- |
| 2003 | -- | -- |
| 2002 | -- | -- |
| 2001 | -- | -- |
Find assessor info on the county website
Neighborhood: 19968
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Nearby schools
GreatSchools rating
- 7/10H. O. Brittingham Elementary SchoolGrades: K-5Distance: 2.3 mi
- 6/10Mariner Middle SchoolGrades: 6-8Distance: 1.7 mi
- 8/10Cape Henlopen High SchoolGrades: 9-12Distance: 10.2 mi
Schools provided by the listing agent
- District: Cape Henlopen
Source: Bright MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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- Delaware
- Sussex County
- Milton
- 19968
- 23761 Winding Way
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