23761 Winding Way, Milton, DE 19968-4501 $1,395,000

Beds/Baths: 4/5
Interior Sq. Ft: 8,057
Acreage: 7.47
Age:19 years
Style:
Contemporary
MLS#: DESU2091770
Subdivision: None Available
Design/Type:
Detached

Description

TRANQUIL FOREST RETREAT! Discover the perfect blend of privacy & location from this lovingly maintained 7.47-acre property near Redden Forest. This serene retreat offers a park-like atmosphere that’s cool in summer and cozy in winter. Featuring a magnificent 8,057 square foot custom-built main house and a charming 532 square foot guest cottage will an additional full bath, kitchenette & sunroom, there is plenty of space for guests, friends, or extended family. Just a 30-minute drive from The Rehoboth Beach boardwalk and Cape Henlopen State Park, it provides an ideal balance of privacy and convenience, allowing you to enjoy nature's tranquility while being close to vibrant coastal attractions. The main house offer 4 levels of spacious living, complete with an oversized three-vehicle garage, including a bay with a 20-foot door that can house your RV or boat. Inside, an elevator ensures accessibility across most levels. Luxurious amenities abound, such as an indoor spa with a vaulted ceiling, maintained by a premium Desert Aire system, and an adjoining greenhouse. The great room features a two-story ceiling and expansive forest views, while large windows fill the home with dappled sunlight. The open-concept kitchen is perfect for entertaining, featuring soft-close cabinetry and ample storage. A spiral staircase leads to a third-floor study offering a peaceful retreat with views of the tree canopy. Enjoy cozy gatherings under the stars from the outdoor fire pit with circular stone seating. A short stone path leads to a separate guest cottage, ideal for visitors or creative projects. This one-of-a-kind designed estate blends natural beauty with practical comfort. The possibilities abound for you to add your own personal touch on making this incredible property your personal retreat! Call and schedule a showing today!

Full Bath: Lower 1

Taxes: $4,567
Home Assoc: No
Condo Assoc: No
Garage: Y
Basement: N
Pool: Yes - Personal
School Dist: Cape Henlopen

Features

Utilities
Heat Pump - Gas BackUp, Wall Unit Heating, Zoned Heating, Electric, Propane - Owned, Central A/C, Zoned Cooling, Ductless/Mini-Split, Electric, Hot Water - Propane, Well Water, Sewer/Septic - Capping Fill, Sewer/Septic - Low Pressure Pipe (LPP), Upper Floor Laundry

Garage/Parking
Attached Garage, Detached Garage, Driveway, Additional Storage Area, Garage - Front Entry, Inside Access, Oversized, Attached Garage Spaces #: 4; Detached Garage Spaces #: 2;

Interior
Carpet, Ceiling Fan(s), Dining Area, Elevator, Carpet Flooring, Concrete Flooring, Engineered Wood Flooring, 2 Story Ceilings, 9'+ Ceilings, Accessibility - Elevator, Accessibility - Grab Bars Mod

Exterior
Slab Foundation, Shingle Roof, Frame Exterior, Stick Built Exterior, Balconies- Multiple, Patio(s), Extensive Hardscape, Outbuilding(s), Play Area, Secure Storage, Underground Lawn Sprinkler, Indoor Pool, Pool/Spa Combo

Lot
Trees/Wooded, Private Lot, Garden/Lawn View, Trees/Woods View

Select a school from the following list. Schools are grouped by school type.
The schools on this list are selected by their proximity of up to 5 miles to the property address. Proximity does not guarantee enrollment eligibility. Please contact the school directly for more information on enrollment requirements.
* If there are more than 5 schools of any type within a close proximity, click on the button to see additional schools of that type near the search address.

Public Elementary (4 schools)

School District Grades Place Distance
Milton Elementary School Cape Henlopen School District K–5 Milton 1.98 mi
H. O. Brittingham Elementary School Cape Henlopen School District K–5 Milton 2.37 mi
Sussex Academy Sussex Academy K–12 Georgetown 3.98 mi
North Georgetown Elementary School Indian River School District Preschool–5 Georgetown 4.51 mi

Public Middle (2 schools)

School District Grades Place Distance
Mariner Middle School Cape Henlopen School District 6–8 Milton 1.73 mi
Sussex Academy Sussex Academy K–12 Georgetown 3.98 mi

Public High (1 schools)

School District Grades Place Distance
Sussex Academy Sussex Academy K–12 Georgetown 3.98 mi

Private (2 schools)

School Grades Place Distance
The Jefferson School Nonsectarian Preschool–8 Georgetown 2.07 mi
Delmarva Christian Schools Milton Campus Christian (no specific denomination) Preschool–8 Milton 4.95 mi

© 2025 LiveBy. All Rights Reserved.

This report is a detailed community overview for Milton (19968), Delaware.

Community Quick Facts

  • Average travel time to work for people in this community: 26
  • Average salary of people in this community: $48,413

Community Summary

  • Population Density (ppl / mile): 184
  • Household Size (ppl): 2.36
  • Households w/ Children: 44%

Housing Inventory

  • Owned: 4,103 (68.1%)
  • Rented: 824 (13.7%)
  • Vacant: 1,099 (18.2%)
  • Total: 6,026

Population Demographics

The population of the community broken down by age group. The numbers at the top of each bar indicate the number of people in the age bracket below.

Total: 11,659
Households: 4,927
Median Age: 49.60

Climate and Weather

The Temperature chart displays average high and low values for January and July, and is designed to provide an indication of both seasonal and daily temperature variability. The Weather Risk Index indicates the calculated risk of each type of weather event occurring in the future. This risk is based on historical localized storm events and weather patterns. The national average for each type of weather event equals a score of 100, so a score of 200 would represent twice the risk as the national average, and a score of 50 would represent half the risk of the national average.

Temperature

Education

Highest Level of Education Attained

  • Less than 9th Grade: 1.9%
  • Some High School: 5.6%
  • High School Graduate: 27.1%
  • Some College: 20.3%
  • Associate Degree: 9.0%
  • Bachelor's Degree: 21.8%
  • Graduate Degree: 14.3%

Income by dollar range

Median Income: $66,631

Fair Market Rents

The Fair Market Rents show average gross rent estimates based on figures provided by the U.S. Department of Housing and Urban Development (HUD).

  • One Bedroom: $591
  • Two Bedroom: $1,001
  • Three Bedroom: $1,420
  • Four Bedroom: $1,208

© 2025 LiveBy. All Rights Reserved.

Contact Information

Listing Courtesy of: Berkshire Hathaway HomeServices PenFed Realty , (302) 645-6661

The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Patterson-Schwartz Real Estate participates, and is provided by BRIGHT through a licensing agreement. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Information Deemed Reliable But Not Guaranteed.
Copyright BRIGHT, All Rights Reserved
Listing data as of 8/10/2025.

23761 Winding Way, Milton, DE 19968-4501

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Broker Compensation

An offer of broker compensation or seller concession is not a guarantee. All compensation offers and concessions are negotiable and subject to written agreement between the parties. Please consult with your real estate agent for more information.