16398 Winding River Dr, Milton, DE 19968
OFF MARKET

$513,100

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,915 sqft (on 0.83 acres)

16398 Winding River Dr, Milton, DE 19968

Refinance Your Home
Currently Off Market - Sold Oct 10, 2024 for $500,000

Home Value

Trulia Estimate
$513K
Since last month
Decreased$700 (-0.1%)
Since last year
Increased$12K (+2.4%)
Since last sale
Increased$14K (+2.7%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +54% in the last 10 years
MonthEstimated value
2026
August 2026$514K
August 2026$513K
July 2026$514K
June 2026$522K
May 2026$510K
April 2026$508K
March 2026$509K
February 2026$501K
January 2026$501K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
16422 Winding River Dr, Milton, DE
0.17
Single-Family Home
$570,000
02/06/26
3
2
2,073
104 Creek Dr, Milton, DE
0.27
Single-Family Home
$525,000
06/16/26
3
2
1,958
29246 River Rock Way, Milton, DE
0.20
Single-Family Home
$680,000
10/23/25
3
2
2,160
16535 Sweetwater Dr, Milton, DE
0.12
Single-Family Home
$585,000
07/03/26
4
2.5
2,495
16244 Edgewater Dr, Milton, DE
0.42
Single-Family Home
$555,000
07/17/26
3
2
2,026
29041 Winding River Ct, Milton, DE
0.31
Single-Family Home
$540,000
12/05/25
3
2.5
2,594
29271 River Rock Way, Milton, DE
0.33
Single-Family Home
$665,950
11/25/25
4
2.5
2,521
16618 Bluestone Ter, Milton, DE
0.38
Single-Family Home
$499,000
11/05/25
3
2
1,899
29830 Sandstone Dr, Milton, DE
0.37
Single-Family Home
$482,500
09/26/25
3
2
1,860
29845 Sandstone Dr, Milton, DE
0.33
Single-Family Home
$440,000
04/02/26
3
2
1,730

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
16408 Winding River Dr, Milton, DE 19968
0.10
$657,700
3
2.5
2,500
Off Market
17012 Regal Dr, Milton, DE 19968
0.07
$292,000
-
-
-
For Sale
16531 Sweetwater Dr, Milton, DE 19968
0.10
$626,700
3
2
2,185
Off Market
16535 Sweetwater Dr, Milton, DE 19968
0.12
$585,000
4
2.5
2,495
Recently Sold
17032 Regal Dr, Milton, DE 19968
0.13
$267,000
-
-
-
For Sale
16422 Winding River Dr, Milton, DE 19968
0.17
$570,000
3
2
2,073
Recently Sold
17038 Regal Dr, Milton, DE 19968
0.14
$267,000
-
-
-
For Sale
16537 Sweetwater Dr, Milton, DE 19968
0.14
$553,900
3
2
2,115
Off Market
16132 Hudson Rd, Milton, DE 19968
0.20
$939,800
4
4.5
4,300
Recently Sold
29246 River Rock Way, Milton, DE 19968
0.20
$678,200
3
2
2,160
Off Market
29248 River Rock Way, Milton, DE 19968
0.23
$689,300
3
2.5
2,600
Off Market

Local Information

  • Map ViewExplore the area around 16398 Winding River Dr.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2008
0.83 acre lot
1,915 sqft
$268/sqft
2 Car Garage
HOA $49/mo

About this House

Back on the market. Disappointed buyers did not yet sell their home creating this fresh opportunity for you to love where you live! Interest rates are down and this single level River Rock Run home with fountain fed pond view in the front and paver patio with evergreen privacy in the rear is back, even better than before and ready for you. The owners bathroom was just painted with a warm and soothing Greek Villa color. Water, radon, septic and termite inspections have already passed. The one window sash needing replacement is done and both outdoor hose bibs have been replaced with new frost free fixtures. If you appreciate nature and love that open, outdoor feeling vs being tightly packed between your neighbors, this lush lawn on 3/4+ acre of well groomed property has plenty of space to spread out and a view that few get to enjoy. There's loads of curb appeal around this coastal home with classy stone front and foundation trim, welcoming porch where you can sit to enjoy sunsets over the pond. Great room with vaulted ceiling, gas fireplace, warm wood floors and a large ceiling fan is the hub for convenient and comfortable one floor living. The two bedroom wing with full bath between can be closed off for privacy with the chic barn door. A short angled hall to a bright rear room can be a formal dining room or a great office space right off the kitchen with a natural view to reduce your stress throughout your workday. The upgraded kitchen with finely detailed maple cabinets has granite tops, a wide breakfast bar, ceramic backsplash and stainless steel appliances ( the microwave and refrigerator were new in 2023.) and well lit with recessed fixtures. The adjoining dining area with new brushed nickel chandelier opens into the sunroom with lots of glass that bathes in the morning light with sliders to the paver patio and a great outdoor entertaining space. The oversized owners suite has a deep tray ceiling, a room sized walk-in closet and the freshly painted bath with large, frosted, glass block window that faces south, custom ceramic and glass shower, space for a make-up table and a linen closet. Laundry room off the kitchen includes the washer and dryer and has inside access to the 2 car garage that has a convenient door to the driveway. Tankless water heater serves your hot water on demand The matching 10x16 shed provides extra storage and trees in the back provide shade and privacy. And let's not overlook what a great location this is. The beaches, restaurants and bike paths are close by yet just above the traffic with many ways to get around making this a place to enjoy that laid back, seaside lifestyle. Make an appointment to see ASAP and come see why folks love living in River Rock Run. PS: Some of the room pictures have the owners furniture, some pictures are virtually staged and are labeled as such for planning ideas.
16398 Winding River Dr, Milton, DE 19968 is a 3 bedroom, 2 bathroom, 1,915 sqft single-family home built in 2008. It last sold for $500,000 on Oct 10, 2024 (4% below the $519,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $513,100, with a rent estimate of $2,520/month.
Last check for updates: about 23 hours ago
Listed by Leo Schwarz, (302) 212-0855
Tesla Realty Group, LLC
Bought with: Leo Schwarz, (302) 212-0855, Tesla Realty Group, LLC
Source: Bright MLS, MLS#DESU2060910

Home Details for 16398 Winding River Dr

Interior Features

Interior Details
Number of Rooms: 8Types of Rooms: Basement
Beds & Baths
Number of Bedrooms: 3Main Level Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 2Number of Bathrooms (main level): 2
Dimensions and Layout
Living Area: 1915 Square Feet
Appliances & Utilities
Utilities: Underground Utilities, CableAppliances: Dishwasher, Ice Maker, Refrigerator, Instant Hot Water, Microwave, Oven/Range - Gas, Tankless Water Heater, Water HeaterDishwasherLaundry: Washer/Dryer Hookups Only,Laundry RoomMicrowaveRefrigerator
Heating & Cooling
Heating: Forced Air,PropaneHas CoolingAir Conditioning: Central Air,ElectricHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 1Fireplace: Gas/PropaneHas a Fireplace
Gas & Electric
Electric: 200+ Amp Service, 120/240V
Windows, Doors, Floors & Walls
Window: Insulated Windows, Window TreatmentsDoor: Insulated, Storm Door(s)
Levels, Entrance, & Accessibility
Stories: 1Levels: OneAccessibility: 2+ Access Exits, Accessible Doors, Accessible Hallway(s), Doors - Lever Handle(s)
View
Has a ViewView: Pond, Trees/Woods

Exterior Features

Exterior Home Features
Roof: Architectural ShinglePatio / Porch: PatioOther Structures: Above Grade, Below GradeExterior: Lawn SprinklerFoundation: Block, Crawl SpaceNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2Open Parking Spaces: 8No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 10Parking: Garage Door Opener,Driveway,Off Street,Attached
Pool
Pool: None
Frontage
Not on Waterfront
Water & Sewer
Sewer: Low Pressure Pipe (LPP)
Finished Area
Finished Area (above surface): 1915 Square Feet

Property Information

Year Built
Year Built: 2008
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Coastal,Ranch/Rambler
Building
Building Name: None AvailableConstruction Materials: Stick Built, Stone, Vinyl SidingNot a New Construction
Property Information
Included in Sale: ShedParcel Number: 23522.00661.00

Price & Status

Price
List Price: $519,000
Status Change & Dates
Off Market Date: Thu Oct 10 2024Possession Timing: Negotiable

Active Status

MLS Status: CLOSED

Location

Direction & Address
City: MILTONCommunity: River Rock Run
School Information
Elementary School District: Cape HenlopenJr High / Middle School District: Cape HenlopenHigh School District: Cape Henlopen

Building

Building Details
Builder Model: Springfield IBuilder Name: Country Life Homes
Building Area
Building Area: 1915 Square Feet

Community

Not Senior Community

HOA

HOA Fee Includes: Common Area Maintenance, Management, Reserve Funds, Road MaintenanceHOA Name: RIVER ROCK HOAHas an HOAHOA Fee: $590/Annually

Lot Information

Lot Area: 0.83 acres

Listing Info

Special Conditions: Standard

Offer

Contingencies: Home InspectionListing Agreement Type: Exclusive Right To SellListing Terms: Cash, Conventional

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: DESU2060910Water ViewWater View: PondAbove Grade Unfinished Area: 1915

Price and Tax history

DateEventPrice
Oct 10, 2024
Source: Bright MLS #DESU2060910
Sold
$500,000
Sep 13, 2024
Source: Bright MLS #DESU2060910
Pending
$519,000
Sep 4, 2024
Source: Bright MLS #DESU2060910
PendingToActive
$519,000
Jul 3, 2024
Source: Bright MLS #DESU2060910
Contingent
$519,000
Jun 25, 2024
Source: Bright MLS #DESU2060910
PriceChange
$519,000
Price decreased by 4%

Market trends in Milton

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$472K
$23.33KMoM
Sale-to-List Price
98.3%
0.1%MoM
Price per sq ft
$240
$4MoM
Available listings
126
1MoM

Around this home

What Locals Say about Milton

At least 58 Trulia users voted on each feature.

  • 97 % Say parking is easy

  • 92 % Say car is needed

  • 92 % Say yards are well-kept

  • 91 % Say it's dog friendly

  • 84 % Say people would walk alone at night

  • 81 % Say there's holiday spirit

  • 70 % Say they plan to stay for at least 5 years

  • 67 % Say kids play outside

  • 64 % Say neighbors are friendly

  • 64 % Say it's quiet

  • 62 % Say streets are well-lit

  • 61 % Say there's wildlife

  • 57 % Say there are sidewalks

  • 56 % Say there are community events

  • 42 % Say it's walkable to restaurants

  • 39 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Cris2461.cm
    "Going to Wilmington is over an hour and half. Better shopping choices are approximately 45 minutes away. Long. No public transportation "
    0
    Flag
  • Ashtat09
    "My neighbors are my friends I like to be around. We play pickleball together 3 to 5 days a week. We do aerobics together and still enjoy bbq parties on the weekends together. "
    0
    Flag
  • Ashtat09
    "I have lived in this neighborhood almost 2 years. Since it is a new development, most everyone wants make new friends and enjoy their new beach home."
    1
    Flag
  • Tj L.
    "My kids live in this area and I’m here multiple times a week. It’s very quiet and has a nice homely feel to it "
    6
    Flag
  • Evritt3
    "Everyone is friendly and picks up after their dogs. No one discriminates against breeds. Anyone and everyone is welcome. "
    7
    Flag
  • Quinese W.
    "I have lived in this neighborhood for eleven years. It's a quiet well maintained street with plenty of on and off street parking, as well as public transportation and friendly neighbors. There are several Elementary, Middle and High Schools in the area. Milton is nearby to many towns/cities that offer fun-filled entertainment for the entire family! This a wonderful place to raise a family, or start out on your own. Very close to Beaches and Resort Areas."
    6
    Flag
  • Gtdonze
    "No public trans. Need a car to go to stores post office dr office just about anywhere. Country living is the trade off. I love it"
    0
    Flag
  • Jessica D.
    "I’ve lived in Milton for almost 20 years. It’s a family town with friendly neighbors and a lot of charm. "
    0
    Flag
  • Trulia User
    "Well kept sidewalks and parks. Easy walking to stores, Milton Theatre, parks, gas station and library. "
    0
    Flag
  • Joepickleball
    "It's got flare with eclectic people. There are a variety of outdoor events for a varied palate. The staples are close by. Name brand and one-of-a-kind stores share the town's boundaries."
    6
    Flag
  • jdoherty24
    "A few miles to the beach so it is quiet. Close enough to enjoy the beach, nightlife and shopping but far enough away so that it is quiet at night"
    0
    Flag
  • Johnanicosia
    "Great place to retire or as a weekend retreat. Prime Hook offers very safe, clean beaches for kids and dogs. Miles of beaches to walk, exploring for wildlife and shells. Excellent place to sail and kayak. Sand bars offer fun for kids. Community backs up to Prime Hook Wildlife refuge teaming with wildlife with nesting ospreys, eagles and other waterfowl. Quiet and peaceful and a perfect all year round destination. It is one of the closest Delaware Bay beaches to Philly, DC, MD and VA.. "
    0
    Flag

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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, and is provided by BRIGHT through a licensing agreement. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 Bright MLS, Inc. Click here for more information

Frequently asked questions about 16398 Winding River Dr

  • What is 16398 Winding River Dr estimated to be worth?
    Trulia's estimated value for 16398 Winding River Dr in Milton, DE is $513,100.
  • What is the price history for 16398 Winding River Dr?
    16398 Winding River Dr in Milton, DE last sold for $500,000 in October 2024.
  • Is Milton a buyer's or seller's market?
    Milton is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Milton?
    The median sale price in Milton is $472K. That is up $23.33K from the prior month.
  • Does 16398 Winding River Dr have air conditioning?
    Yes, 16398 Winding River Dr in Milton, DE has air conditioning.
  • Does 16398 Winding River Dr have laundry facilities?
    Yes, 16398 Winding River Dr in Milton, DE has laundry facilities.

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