OFF MARKET

Off market nov 2021 for $420K

$430,494

Est. refi paymentEst. refi $2,831/mo

•

2,273

sq ft

442 Woodside Rd, Millsboro, DE 19966

About this home

Conveniently located In Winding Creek Village, a boat-oriented community, this charming home is ready for you! Lovingly cared for, this home has a beautiful wrap-around porch, gorgeous views of the sunset, a large corner lot, and plenty of space for family and friends. On the first floor, you will find three bedrooms and 2 full baths, a large family room with a propane fireplace, a beautiful back sunroom that can be used as a flex room, a nicely sized kitchen with a breakfast nook, and a formal dining room area. Need additional space? Ascend the spiral staircase to the large loft area to be used as you see fit! There is also an easily accessible large storage room. Nestled behind Baywood, this community and location are hard to beat. Shopping, marinas, golf, medical facilities, etc are all located within a few miles. Come enjoy the boating life, or sit back, relax and enjoy the space inside and outside of this home.

Single-familyProperty Type

1997Year Built

0.45 acresLot Size

$189Est. Price/Sq.Ft.

2 garage spacesParking

Listed by Christine MCCOY • Coldwell Banker Realty

•302-539-1777 (broker)

Bought with Jim Stromberg • Coldwell Banker Realty

•302-539-1777 (broker)

Redfin checked: 3 minutes ago

•Source:BRIGHT MLS #DESU2008350

Redfin Estimate

$430,494

$10K since sold in November 2021$2,000 since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 41.9% higher than the average sale price ($303K) of 6 comparable homes.

SOLD JUN 12, 2026
$525,000
A
3 beds2 baths2,016 sq ft
458 Woodside Rd, Millsboro, DE 19966
SOLD SEP 30, 2026
$340,000
B
3 beds2 baths2,084 sq ft
32595 Long Iron #3217, Millsboro, DE 19966
SOLD SEP 8, 2026
$313,000
C
3 beds2 baths1,890 sq ft
32589 Long Iron Way #3216, Millsboro, DE 19966
SOLD OCT 1, 2026
$327,500
D
4 beds2 baths2,048 sq ft
24349 Canal Dr, Millsboro, DE 19966
SOLD SEP 28, 2026
$165,000
E
3 beds2 baths1,920 sq ft
33288 Arrowood Cv #2726, Long Neck, DE 19966
SOLD SEP 18, 2026
$150,000
F
3 beds2 baths2,173 sq ft
25306 Crab Aly W #1506, Millsboro, DE 19966

Claim this home to receive a free report every month with insights on the changing estimate.

Earn from this home

Sell

$99,699

Est. take-home

List your home with Redfin and save $4,305

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$2,576/mo

Redfin rental estimate

List your home for rent

Market trends in 19966, DE

Last updated October 2026

Buyer's Market

Seller's Market

Buyer's market

Sale-to-list price

97.6%

0.3% MoM

Median sale price

$327K

$3K MoM

Avg. days on market

89d

0 days MoM

Recently sold homes

300

0 MoM

New listings for sale

NEW 10 HRS AGO
$325,000
4 beds2 baths2,356 sq ft
1 John B Dr, Millsboro, DE 19966
(302) 601-4171
COMING SOON
27011 Sand Shrimp Ln #9987, Millsboro, DE 19966
$130,000
3 beds1 bath840 sq ft
27011 Sand Shrimp Ln #9987, Millsboro, DE 19966
(302) 644-2121
NEW
$425,000
3 beds2 baths1,854 sq ft
32253 Bayshore Dr, Millsboro, DE 19966
(302) 273-4998
NEW
$94,999
2 beds2 baths1,298 sq ft
25448 Crab Aly Aly W #1393, Millsboro, DE 19966
(302) 934-3970
$129,900
2 beds2 baths1,224 sq ft
29512 Salt Marsh Loop #48056, Millsboro, DE 19966
(302) 644-2121
$185,900
2 beds2 baths1,680 sq ft
35694 E Harbor Dr, Millsboro, DE 19966
(302) 644-2121
SHORT SALE
$340,000
3 beds1 bath1,170 sq ft
22 Comanche Cir, Millsboro, DE 19966
(888) 543-4829
$335,000
3 beds3.5 baths2,371 sq ft
35144 Wright Way, Millsboro, DE 19966
(302) 273-4998
3D WALKTHROUGH
$70,000
3 beds2 baths938 sq ft
21994 County Ave, Millsboro, DE 19966
(302) 273-4998
OPEN SAT, 11AM TO 1PM
$178,000
3 beds2 baths1,369 sq ft
26876 Diver Duck Dr, Millsboro, DE 19966
(410) 453-0500
See all

Provided by Redfin

Sale history for 442 Woodside Rd

Date

Event

Price

BRIGHT MLS #DESU2008350

Nov 30, 2021

Sold

$420,000

$185/sq ft

Nov 18, 2021

Pending

—

Nov 2, 2021

Contingent

—

Oct 30, 2021

Listed

$415,000

$183/sq ft

BRIGHT MLS #DESU175618

Mar 11, 2021

Sold

$379,500

$167/sq ft

Feb 9, 2021

Pending

—

Jan 18, 2021

Contingent

—

Jan 15, 2021

Listed

$379,500

$167/sq ft

+26

Whether you're seeking a part-time or full time residence, this move-in ready 3+ bedroom, 2 bath home is sure to please. On appox. a half acre of land, nestled in the private community of Winding Creek Village across from Baywood Country Club you can enjoy a stocked pond and a community boat ramp. Enter the foyer and you are greeted with an open living area with a fireplace as well as high ceilings opening up to a large 2nd floor bonus room, . The kitchen is open with lots of light, an eat-in area and peninsula bar. Nice relaxing 4-seasons room great for reading and taking in the sunset. The 2 car (heated) garage is pristine and a nice size shed in backyard helps keep the garden tools and mowing equipment stored away for the off-season. This home is an all around gem.

BRIGHT MLS #1001166814

Aug 1, 2016

Listing Removed

—

Feb 19, 2016

Listed

$299,900

$132/sq ft

BRIGHT MLS #1001126998

Oct 4, 2012

Listing Removed

—

Apr 3, 2012

Listed

$339,900

$150/sq ft

BRIGHT MLS #1001121130

Sep 13, 2011

Listing Removed

—

Jan 31, 2011

Listed

$339,900

$150/sq ft

BRIGHT MLS #1001115488

Aug 25, 2010

Listing Removed

—

Feb 15, 2010

Listed

$349,900

$154/sq ft

BRIGHT MLS #1001108994

Oct 22, 2009

Listing Removed

—

Jan 21, 2009

Listed

$359,900

$158/sq ft

BRIGHT MLS #1001709244

Jul 22, 2009

Listing Removed

—

Jan 23, 2009

Listed

$369,900

$163/sq ft

BRIGHT MLS #1001092502

Mar 4, 2007

Listing Removed

—

Nov 15, 2006

Listed

$425,000

$187/sq ft

Public Records

Jun 11, 1996

Sold

$27,700

$12/sq ft

Year

Property tax

Land + Additions

Assessment*

2026

$926 (−0.4%)

$58,250 + $156,550

$214,800

2025

$930 (−1.1%)

$58,250 + $156,550

$214,800

2024

$940 (+0.1%)

$58,250 + $156,550

$214,800

2023

$939 (+1.6%)

$4,000 + $18,450

$22,450

2022

$924 (+3.0%)

$4,000 + $18,450

$22,450

2021

$897 (+70.6%)

$4,000 + $18,450

$22,450

2020

$526 (+0.3%)

$4,000 + $18,450

$22,450

2019

$524 (+1.4%)

$4,000 + $18,450

$22,450

2018

$517 (−0.7%)

$4,000 + $18,450

$22,450

2017

$520 (−33.1%)

$4,000 + $18,450

$22,450

2016

$778 (−1.4%)

$4,000 + $18,450

$22,450

2014

$789

$4,000 + $18,450

$22,450

Tax history for 442 Woodside Rd

Year

Property tax

Land + Additions

Assessment*

2026

$926 (−0.4%)

$58,250 + $156,550

$214,800

2025

$930 (−1.1%)

$58,250 + $156,550

$214,800

2024

$940 (+0.1%)

$58,250 + $156,550

$214,800

2023

$939 (+1.6%)

$4,000 + $18,450

$22,450

2022

$924 (+3.0%)

$4,000 + $18,450

$22,450

2021

$897 (+70.6%)

$4,000 + $18,450

$22,450

2020

$526 (+0.3%)

$4,000 + $18,450

$22,450

2019

$524 (+1.4%)

$4,000 + $18,450

$22,450

2018

$517 (−0.7%)

$4,000 + $18,450

$22,450

2017

$520 (−33.1%)

$4,000 + $18,450

$22,450

2016

$778 (−1.4%)

$4,000 + $18,450

$22,450

2014

$789

$4,000 + $18,450

$22,450

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Public record
Zoning

Beds

Baths

Stories

Lot width

100 ft.

Lot depth

200 ft.

Lot size

0.57 Acres

Year renovated

—

Sq. Ft.

1,673

Year built

1997

Style

Single Family Residential

County

Sussex County

APN

234-24.00-270.00

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Aug 24, 2026.

AR-1

Agricultural Residential District

The purpose of these districts is to provide for a full range of agricultural activities and to protect agricultural lands, as one of the county's most valuable natural resources, from the depreciating effect of objectional, hazardous and unsightly uses. They should also protect established agricultural operations and activities. These districts are also intended for protection of watersheds, water resources, forest areas and scenic values and, at the same time, to provide for low-density single-family residential development, together with such churches, recreational facilities and accessory uses as may be necessary or are normally compatible with residential surroundings. The AR regulations seek to prevent untimely scattering of more-dense urban uses, which should be confined to areas planned for efficient extension of public services.

Permitted uses

Include but are not limited to:

Greenhouse / nursery
Religious facility
Housing-Single unit
Golf related
Recreation-Other
Veterinary clinic
Agriculture
Park & open space

Property details

Parking

Parking Information
# of Attached Garage Spaces: 2
Garage Features: Garage - Front Entry
# of Total Garage and Parking Spaces: 6
Has Garage
# of Garage Spaces: 2
Driveway - # of Spaces: 4
Paved Driveway
Driveway, Attached Garage

Interior

Virtual Tour

Bedroom Information
# of Bedrooms On Main Level: 3

Bathroom Information
# of Bathrooms (Full) On Main Level: 2
# of Bathrooms (Full): 2

Interior Information
Appliances: Refrigerator, Microwave, Stove, Oven/Range - Gas
Interior Features: Breakfast Area, Dining Area, Entry Level Bedroom, Floor Plan - Traditional, Kitchen - Eat-In, Tub Shower
Living Area Sq.Ft. Source: Estimated

Room Information
Dining Room, Master Bedroom, Kitchen, Family Room, Den, Breakfast Room, Loft, Storage Room, Master Bathroom, Full Bath, Additional Bedroom
Laundry Type: Main Floor

Fireplace Information
Has Fireplace
# of Fireplaces: 1
Gas/Propane

Basement Information
Basement: No

Exterior

Property Information
Not Federal Flood Zone
Total Below Grade Sq. Ft.: 0
Accessibility Features: 2+ Access Exits
Ownership Interest: Fee Simple
Property Condition: Very Good
Year Built Source: Assessor

Building Information
Building Name: NONE AVAILABLE
Construction Materials: Frame, Vinyl Siding
Foundation Details: Concrete Perimeter, Crawl Space
Other Structures: Above Grade, Below Grade
Outdoor Living Structures: Porch(es), Wrap Around
Structure Type: Detached
Other Structures: Shed

Lot Information
Lot Size Dimensions: 100.00 x 200.00
Lot Dimensions Source: Assessor
Navigable Water
Tidal Water: No

Above Grade Information
Finished Sq.Ft.: 2,273
Finished Sq.Ft. Source: Estimated

Below Grade Information
Unfinished Sq.Ft. Source: Assessor
Finished Sq.Ft. Source: Assessor

Financial

Tax Information
County Tax: $100
School Tax: $797
Tax Year: 2021
Tax Annual Amount: $885

Assessments Information
Year Assessed: 2021

Utilities

Utilities Information
Central Air
Cooling Type: Central A/C
Cooling Fuel: Electric
Forced Air
Heating Fuel: Propane - Owned
Hot Water: Electric
Sewer Septic: Septic Exists, Gravity Sept Fld
Water Source: Well, Well Permit on File
Municipal Trash: No

Location

Homeowners Association Information
HOA/Condo/Coop Fee Includes: Common Area Maintenance
HOA/Condo/Coop Amenities: Boat Ramp
HOA Fee: $350
HOA Fee Frequency: Annually

School Information
School District Name: INDIAN RIVER
School District Source: Listing Agent

Location Information
Outside City Limits
Sussex DE Quadrants: Between Rt 1 & 113
Directions: Take DE-26 W and DE-24 E to Bay Farm Road, Head west on Atlantic Ave, continue onto Main ST, turn right onto US-113 N/E Dupont Blvd. Turn right onto Washington St, continue onto Main St, take rd 298 to Woodside Rd, turn right onto Bay Farm rd, turn left onto School Ln, turn right onto Pond rd, turn left onto Quail rd, Quail Rd turns right and becomes Woodside rd.

Waterfrontage Information
Water Access
Water Oriented
Water Body Type: Canal

Public facts

Beds: 3
Baths: 2.0
Sq. Ft.: 1,673
Stories: 1.0
Lot Size: 0.57 acres
Style: Single Family Residential
Year Built: 1997
Year Renovated: —
County: Sussex County
APN: 234-24.00-270.00

Home facts updated by county records on Aug 24, 2026

Around this home

Schools

K - 12
Preschool & daycare

Long Neck Elementary School

Public K-5 • Assigned • 1.2mi

5/10

Millsboro Middle School

Public 6-8 • Assigned • 7.3mi

4/10

Sussex Central High School

Public 9-12 • Assigned • 8.4mi

3/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

8/10 Heat Factor

7 days above 101° expected this year, 18 days in 30 years

8/10 Wind Factor

80% chance of strong winds in next 30 years

2/10 Air Factor

1 unhealthy days expected this year, 1 days in 30 years

Provided by First Street

Historical weather

Millsboro, DE • 19966

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 9.2 hours in June and 5.3 hours in December, which is comparable to the U.S. average for solar exposure.

9.2 hrs

5.3 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$409,000 – $496,000

Reach more buyers when you sell with Redfin. Save up to $4,305 in fees. 3 minutes to get started.

Get a free, detailed breakdown of how we calculated your estimate.

Nearby similar homes

$209,000

3 beds2 baths1,568 sq ft

32840 Tern Cv #51774, Millsboro, DE 19966

Rear screened porch • Wooded lot • Front porch

(302) 285-5100

NEW CONSTRUCTION

$308,185

3 beds2.5 baths1,760 sq ft

25694 Crab Aly E #1091, Millsboro, DE 19966

New construction • Spacious kitchen • Large center island

(302) 945-3820

$574,000

5 beds3 baths3,000 sq ft

23392 Boatmans Ct, Lewes, DE 19958

Community clubhouse • Fitness center • Swimming pool

(302) 645-6661

$860,000

5 beds3.5 baths2,921 sq ft

27052 Firefly Blvd, Millsboro, DE 19966

Covered rear porch • Stone gas fireplace • Built-in gas grill

(302) 227-6767

$90,000

3 beds2 baths924 sq ft

26272 Crows Nest Ct W #48915, Millsboro, DE 19966

Quiet cul-de-sac • En-suite bath • Large flat yard

(302) 217-6692

3D WALKTHROUGH

$575,000

3 beds3.5 baths3,360 sq ft

23651 Herring Reach Ct, Lewes, DE 19958

Waterfront community • Community pool • Community dock

(302) 526-2886

New listings for sale in 19966

NEW 10 HRS AGO

$325,000

4 beds2 baths2,356 sq ft

1 John B Dr, Millsboro, DE 19966

Fenced-in backyard • Storage shed • Paved driveway

(302) 601-4171

COMING SOON

$130,000

3 beds1 bath840 sq ft

27011 Sand Shrimp Ln #9987, Millsboro, DE 19966

4.36 acre lot • Built 1995

(302) 644-2121

NEW

$425,000

3 beds2 baths1,854 sq ft

32253 Bayshore Dr, Millsboro, DE 19966

Manicured lawn • Open floor plan • Corian countertops

(302) 273-4998

NEW

$94,999

2 beds2 baths1,298 sq ft

25448 Crab Aly Aly W #1393, Millsboro, DE 19966

Updated plumbing • Walk-in shower • Two decks

(302) 934-3970

$129,900

2 beds2 baths1,224 sq ft

29512 Salt Marsh Loop #48056, Millsboro, DE 19966

Waterfront community • Community boat docks • Private beach

(302) 644-2121

$185,900

2 beds2 baths1,680 sq ft

35694 E Harbor Dr, Millsboro, DE 19966

332.36 acre lot • Built 1969

(302) 644-2121

SHORT SALE

$340,000

3 beds1 bath1,170 sq ft

22 Comanche Cir, Millsboro, DE 19966

0.36 acre lot • 2 garage spots • Built 1981

(888) 543-4829

$335,000

3 beds3.5 baths2,371 sq ft

35144 Wright Way, Millsboro, DE 19966

Golf course views • Finished rec room • Open main level

(302) 273-4998

3D WALKTHROUGH

$70,000

3 beds2 baths938 sq ft

21994 County Ave, Millsboro, DE 19966

Single level living • Corner lot • Updated bathrooms

(302) 273-4998

Home values near 442 Woodside Rd

Data from public records.

Address	Redfin Estimate
452 Woodside Road, Millsboro, DE 3 Beds \| 4 Baths \| 2464 Sq. Ft.	$439,955
448 Woodside Road, Millsboro, DE 4 Beds \| 4 Baths \| 3284 Sq. Ft.	$623,667
449 Woodside Road, Millsboro, DE 3 Beds \| 2 Baths \| 2238 Sq. Ft.	$478,859
445 Woodside Road, Millsboro, DE 3 Beds \| 3 Baths \| 2654 Sq. Ft.	$477,438
4 Creek Drive, Millsboro, DE 3 Beds \| 2 Baths \| - Sq. Ft.	$457,535
341 Pond Road, Millsboro, DE 3 Beds \| 2 Baths \| 1800 Sq. Ft.	$402,689
439 Grey Gull Lane, Millsboro, DE 3 Beds \| 4 Baths \| 1827 Sq. Ft.	$472,488

Address	Redfin Estimate
450 Woodside Road, Millsboro, DE 3 Beds \| 2 Baths \| 1675 Sq. Ft.	$370,471
453 Woodside Road, Millsboro, DE 3 Beds \| 3 Baths \| 2256 Sq. Ft.	$449,986
447 Woodside Road, Millsboro, DE 4 Beds \| 3 Baths \| 1216 Sq. Ft.	$386,171
446 Woodside Road, Millsboro, DE 3 Beds \| 2 Baths \| 2347 Sq. Ft.	$500,755
339 Pond Road, Millsboro, DE 3 Beds \| 4 Baths \| 2036 Sq. Ft.	$523,920
345 Pond Road, Millsboro, DE 4 Beds \| 2.5 Baths \| 2392 Sq. Ft.	$442,818
437 Grey Gull Lane, Millsboro, DE 3 Beds \| 2 Baths \| 2400 Sq. Ft.	$470,613

Address	Redfin Estimate
444 Woodside Road, Millsboro, DE 3 Beds \| 3 Baths \| 2104 Sq. Ft.	$435,344
451 Woodside Road, Millsboro, DE 4 Beds \| 3 Baths \| 1256 Sq. Ft.	$369,263
443 Woodside Road, Millsboro, DE 3 Beds \| 2 Baths \| 1474 Sq. Ft.	$356,484
348 Pond Road, Millsboro, DE 3 Beds \| 2 Baths \| - Sq. Ft.	$477,964
343 Pond Road, Millsboro, DE 4 Beds \| 5 Baths \| 1570 Sq. Ft.	$472,639
440 Grey Gull Lane, Millsboro, DE 3 Beds \| 2 Baths \| 2084 Sq. Ft.	$560,624
438 Grey Gull Lane, Millsboro, DE 4 Beds \| 2 Baths \| 2481 Sq. Ft.	$468,462

Property information provided by BRIGHT MLS when last listed in 2021. This data may not match . Learn more.

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

Redfin Brokerage Licenses

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.

GreatSchools Ratings provided by GreatSchools.org.

The Commons at Radish Farms homes for sale
The Villages of Millwood homes for sale
Whartons Bluff homes for sale
Plantation Lakes homes for sale

19939 homes for sale
19945 homes for sale
19966 homes for sale
19947 homes for sale

Houses for rent in Millsboro	Agents near me	Bethany Beach, DE homes for sale	Millsboro Housing Market
Houses for sale near me	Wilmington, DE homes for sale	Middletown, DE homes for sale
Land for sale near me	Rehoboth Beach, DE homes for sale	Dover, DE homes for sale
Open Houses near me	Lewes, DE homes for sale	Millsboro Property Records
Condos for sale near me	Newark, DE homes for sale	DE New Listings

Lewes homes for sale
Ocean City homes for sale
Rehoboth Beach homes for sale

About this home

Redfin Estimate

Earn from this home

Market trends in 19966, DE

Sale history for 442 Woodside Rd

Tax history for 442 Woodside Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 19966

Home values near 442 Woodside Rd

More real estate resources