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$575,000

  • For Sale
  • Under Contract
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 2,073 Sq. Ft.
  • 2 Car Garage
  • Updated 5 days ago
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This beautifully maintained contemporary home offers three bedrooms and two baths in a well-established neighborhood where the lots are spacious, the neighbors are set back for privacy, and the pace feels a little more relaxed. In the summer months, you'll even be treated to the charm of an ice cream truck making its Thursday rounds. The large three-quarter-acre lot is a retreat in itself, with no homes directly behind and year- round beauty from seasonal blooms, mature Crepe Myrtle trees in the backyard, and fresh landscaping accented with new mulch. The yard is kept lush and vibrant with an underground irrigation system, and from the front yard, you can enjoy a tranquil view of the neighborhood pond. Step inside to an open-concept layout filled with natural light. The bright dining room greets you with a soaring vaulted ceiling and stunning atrium windows framing the greenery outside. The living room features brand-new carpeting, vaulted ceilings, a ceiling fan, and a double-sided gas fireplace that adds warmth and charm to both the living room and the sunroom. The sunroom offers abundant windows, up/down shades for versatile light control, a vaulted ceiling, ceiling fan, and a sliding glass door leading to the screened porch, perfect for breezy afternoons without bugs. The kitchen is a chef's delight, with all-new stainless-steel appliances, granite countertops, recessed lighting, LVP flooring, and a cozy breakfast nook. On one side of the home are two comfortable bedrooms and a full bath, with one bedroom offering serene backyard views. Upstairs, a large, floored attic space awaits your personal touch, offering endless possibilities for expansion. On the opposite side of the home is a sitting room, ideal for an office, den, or media room. The primary suite is a private retreat, featuring a walk-in closet and a spa-like en suite bath with a walk-in shower, dual vanity, and a soaking tub set beneath a large glass block window for natural light and privacy. Enjoy outdoors on the screened porch or step down to the paved patio where you can grill, dine al fresco, and take in the beauty of the surrounding gardens. While this home feels worlds away from the hustle and bustle, it's just minutes from downtown Milton and the beaches, offering the perfect blend of peaceful living and convenient access to coastal attractions.

Full Property Details for 16422 Winding River Dr

General

  • Price: $575,000
  • HOA FEE: $49/month
  • HOA FEE FREQ.: Annually
  • Taxes: $1,006 (2025)
  • Status: Under Contract
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: DESU2092676
  • Updated: 12/17/2025
  • Added to Site: 157 day(s) ago

Interior

  • Rooms/Areas: Dining Room, Primary Bedroom, Sitting Room, Bedroom 2, Bedroom 3, Kitchen, Foyer
  • Interior Features: Attic, Breakfast Area, Carpet, Ceiling Fan(s), Dining Area, Entry Level Bedroom, Family Room Off Kitchen, Kitchen - Gourmet, Primary Bath(s), Pantry, Bathroom - Soaking Tub, Bathroom - Stall Shower, Bathroom - Tub Shower, Window Treatments, Walk-in Closet(s), Upgraded Countertops
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Fireplace(s): Double Sided, Fireplace - Glass Doors, Gas/Propane, Mantel(s)
  • Appliances: Built-In Microwave, Built-In Range, Dishwasher, Dryer, Freezer, Icemaker, Oven/Range - Electric, Exhaust Fan, Stainless Steel Appliances, Refrigerator, Washer, Water Dispenser, Water Heater
  • Flooring: Ceramic Tile, Luxury Vinyl Plank, Partially Carpeted

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2
  • Main Floor Baths: 2
  • Main - Full Baths: 2

Bedrooms

  • Total Bedrooms: 3
  • Bedrooms Main & Up: 3

Other Rooms

  • Laundry: Dryer In Unit, Main Floor, Washer In Unit

Additional Information

  • Security/Safety: Carbon Monoxide Detector(s)

Exterior

  • Exterior Features: Underground Lawn Sprinkler

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 8
  • Parking Features: Asphalt Driveway, Paved Parking
  • Parking Type: Attached Garage, Driveway
  • Garage Description: Garage - Side Entry

Location

  • Area: Broadkill Hundred (31003)
  • County: SUSSEX
  • Subdivision: River Rock Run
  • Driving Directions: GPS

School Information

  • School District: Cape Henlopen

Community

  • Association: Yes

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Central A/C
  • Cooling Fuel: Electric
  • Heating Type: Forced Air
  • Heating Fuel: Propane - Leased
  • Water Heater: 60+ Gallon Tank

Utilities

  • Sewer: Septic Exists
  • Water: Well, Public

Structural Information

  • Architectural Style: Contemporary
  • Structure Type: Detached
  • Construction: Frame, Vinyl Siding
  • Foundation: Crawl Space
  • Roof: Architectural Shingle
  • Walls/Ceilings: High, Vaulted Ceilings
  • Windows: Atrium, Double Pane, Double Hung, Screens, Sliding, Transom, Vinyl Clad
  • Doors: Six Panel, Sliding Glass
  • Stories Description: Main
  • Square Feet: 2,073
  • Sq. Ft. Source: Assessor
  • Living Area: 2,073 Sq. Ft.
  • Finished Above Grnd: 2,073 Sq. Ft.
  • Year Built: 2006
  • Year Built Source: Assessor
  • Property Condition: Excellent

Lot Features

  • Property View: Garden/Lawn, Trees/Woods
  • Lot Size (Acres): 0.8
  • Lot Size (Sq. Ft.): 34,848
  • Lot Size Source: Assessor
  • Lot Dimensions: 150.00 x 219.00
  • Zoning: AR-1
  • Lot Description: Backs to Trees, Front Yard, Landscaping, Rear Yard, SideYard(s), Trees/Wooded

Financial Considerations

  • Price Per Sq. Ft.: $277.38
  • Association Fee: $590
  • Assoc Fee Freq.: Annually
  • Assessment Year: 2025
  • School Tax: $904
  • County Tax: $101
  • County Tax Freq: Annually
  • Tax Amount: $1,006
  • Tax Year: 2025
  • Tax Total Finished Sq. Ft.: 2073

Disclosures and Reports

  • Ownership: Fee Simple
  • Lot Number: 10

Listed by Northrop Realty, Vincente Michael DiPietro

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Listing agent

— 16422 Winding River Dr —

  • Vincente Michael DiPietro

    Northrop Realty

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 16422 Winding River Dr

School District:Cape Henlopen School District
NameGradesDistance
Milton Elementary School, Milton, DE
512 Federal Street, Milton, DE 19968
PK-54 mi
Beacon Middle School
19483 John J Williams Highway, Lewes, DE 19958
4-86.1 mi
Cape Henlopen High School
1250 Kings Highway, Lewes, DE 19958
8-125 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 16422 Winding River Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
10/15/2025
Price Reduced
$575,000
-1.71%
MLS
9/20/2025
Price Reduced
$585,000
-0.85%
MLS
8/14/2025
Listed
$590,000
46.44%
MLS
8/17/2006
Sold
$402,900
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 16422 Winding River Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$1,006
-23%
$36,550
—
2023
$1,300
5%
$36,550
—
2022
$1,237
-6%
$36,550
—
2021
$1,321
—
$36,550
—
2020
$1,316
9%
$36,550
—
2018
$1,205
6%
$36,550
—
2017
$1,137
18%
$36,550
—
2016
$960
7%
$36,550
—
2015
$895
-26%
$36,550
-19%
2014
$1,203
4%
$44,950
—
2013
$1,155
—
$44,950
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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NMLS#: 1598647

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Listed by Northrop Realty, Vincente Michael DiPietro

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16422 Winding River Drive, Milton, DE 19968 (MLS# DESU2092676) is a Single Family property with 3 bedrooms and 2 full bathrooms. 16422 Winding River Drive is currently listed for $575,000 and was received on August 14, 2025. Want to learn more about 16422 Winding River Drive? 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.

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