OFF MARKET

Off market aug 2024 for $689K

$623,667

Est. refi paymentEst. refi $3,106/mo

•

3,284

sq ft

448 Woodside Rd, Millsboro, DE 19966

About this home

Employment relocation. Bring all offers. CUSTOM-BUILT LUXURY in the established water access community of Winding Creek Village, providing convenient access to Rehoboth Bay. This home is the ultimate retreat featuring a private in-ground pool with new liner & pump, an expansive side deck with hot tub, outdoor shower, stunning pergola, and a gas line hookup for grilling, an outdoor firepit, plus a one-of-a-kind entertainment room complete with built-in wet bar with a 6-tap kegerator, and a built-in lounge that is perfect for hosting game and movie nights or accommodating the overflow of friends and family visiting from out of town. The highlights continue with 4 bedrooms, including a first-floor primary suite with spa-like bath and two large walk-in closets. Custom cabinetry, stainless steel appliances, and walk-in pantry in the kitchen, vaulted ceilings, and gas fireplace in the living room, and so much more that needs to be seen in person to truly appreciate. Along with the home’s long list of amenities, this community offers water access, boat ramp with direct access to the Rehoboth Bay, five minutes to the Ocean, several community ponds, walking paths, benches, and abundant wildlife. A short drive to local fine dining, recreational options, golfing, and gorgeous beaches. Everything you've always dreamed about in a house - call today to schedule your private showing!

Single-familyProperty Type

1999Year Built

0.57 acresLot Size

$190Est. Price/Sq.Ft.

6 spacesParking

Listed by Lee Ann Wilkinson • Berkshire Hathaway HomeServices PenFed Realty

•302-645-6661 (broker)

Bought with Cary Boczon • Iron Valley Real Estate at The Beach

•302-541-8787 (broker)

•sherricustodio@gmail.com (broker)

Redfin checked: 2 minutes ago

•Source:BRIGHT MLS #DESU2057526

Redfin Estimate

$623,667

$65K since sold in August 2024$8,000 since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 1.1% lower than the average sale price ($631K) of 6 comparable homes.

SOLD OCT 26, 2026
$700,000
A
4 beds3 baths3,442 sq ft
88 Creek Dr, Millsboro, DE 19966
SOLD JUN 26, 2026
$828,750
B
4 beds4 baths3,116 sq ft
304 Island Rd, Millsboro, DE 19966
SOLD JUN 12, 2026
$525,000
C
3 beds2 baths2,016 sq ft
458 Woodside Rd, Millsboro, DE 19966
SOLD SEP 1, 2026
$535,000
D
4 beds2.5 baths2,590 sq ft
33810 N Heron Dr, Lewes, DE 19958
SOLD MAR 30, 2026
$590,000
E
4 beds3 baths3,020 sq ft
292 Pond Rd, Millsboro, DE 19966
SOLD AUG 14, 2026
$605,000
F
4 beds2 baths2,600 sq ft
108 Teal Dr, Millsboro, DE 19966

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Earn from this home

Sell

$56,784

Est. take-home

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Refinance

Est. cash available

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Rent

$3,263/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 448 Woodside Rd

Date

Event

Price

BRIGHT MLS #DESU2057526

Aug 19, 2024

Sold

$689,000

$210/sq ft

Aug 5, 2024

Pending

—

Jun 14, 2024

Contingent

—

May 20, 2024

Price Changed

$699,000

$213/sq ft

May 2, 2024

Price Changed

$719,000

$219/sq ft

Mar 26, 2024

Price Changed

$759,900

$231/sq ft

Mar 8, 2024

Listed

$799,000

$243/sq ft

Mar 7, 2024

Coming Soon

$799,000

$243/sq ft

Public Records

Jun 7, 2019

Sold

$400,000

$122/sq ft

BRIGHT MLS #DESU133446

Jun 7, 2019

Listing Removed

—

May 31, 2019

Sold

$400,000

$122/sq ft

May 6, 2019

Pending

—

Mar 22, 2019

Contingent

—

Mar 15, 2019

Pending

—

Mar 7, 2019

Listed

$424,900

$129/sq ft

+49

Located on a spacious half-acre lot in the desirable community of Winding Creek Village, this four bedroom, three bathroom home boasts several amenities including stainless steel kitchen appliances, a great room with a fireplace, and a private suite on the second floor. Spend your summers lounging poolside, relaxing in the hot tub, and entertaining on your spacious back deck - complete with a stunning pergola, fire pit, and a direct gas line perfect for firing up the grill and hosting barbeques. Enjoy exclusive boating and fishing just minutes away at the community boat launch, and a short drive to local fine dining, recreational options, and gorgeous beaches. Custom-built and impeccably maintained, this home is one of a kind and truly inspires the entertainer in us all. Don't wait for everything you've always dreamt of - call us today to schedule your private showing!

BRIGHT MLS #DESU129282

Feb 2, 2019

Listed

$424,900

$129/sq ft

Feb 2, 2019

Listing Removed

—

Year

Property tax

Land + Additions

Assessment*

2026

$1,499 (+1.2%)

$58,450 + $288,050

$346,500

2025

$1,480 (+1.6%)

$58,450 + $288,050

$346,500

2024

$1,457 (+0.1%)

$58,450 + $288,050

$346,500

2023

$1,455 (+1.6%)

$4,000 + $30,650

$34,650

2022

$1,432 (+3.0%)

$4,000 + $30,650

$34,650

2021

$1,390 (+4.7%)

$4,000 + $30,650

$34,650

2020

$1,327 (+0.4%)

$4,000 + $30,650

$34,650

2019

$1,322 (−0.9%)

$4,000 + $30,650

$34,650

2018

$1,334 (−0.8%)

$4,000 + $30,650

$34,650

2017

$1,345 (+13.2%)

$4,000 + $30,650

$34,650

2016

$1,188 (−1.4%)

$4,000 + $30,650

$34,650

2014

$1,205

$4,000 + $30,650

$34,650

Tax history for 448 Woodside Rd

Year

Property tax

Land + Additions

Assessment*

2026

$1,499 (+1.2%)

$58,450 + $288,050

$346,500

2025

$1,480 (+1.6%)

$58,450 + $288,050

$346,500

2024

$1,457 (+0.1%)

$58,450 + $288,050

$346,500

2023

$1,455 (+1.6%)

$4,000 + $30,650

$34,650

2022

$1,432 (+3.0%)

$4,000 + $30,650

$34,650

2021

$1,390 (+4.7%)

$4,000 + $30,650

$34,650

2020

$1,327 (+0.4%)

$4,000 + $30,650

$34,650

2019

$1,322 (−0.9%)

$4,000 + $30,650

$34,650

2018

$1,334 (−0.8%)

$4,000 + $30,650

$34,650

2017

$1,345 (+13.2%)

$4,000 + $30,650

$34,650

2016

$1,188 (−1.4%)

$4,000 + $30,650

$34,650

2014

$1,205

$4,000 + $30,650

$34,650

*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

1.5

Lot width

125 ft.

Lot depth

200 ft.

Lot size

0.57 Acres

Year renovated

—

Sq. Ft.

2,067

Year built

1999

Style

Single Family Residential

County

Sussex County

APN

234-24.00-273.00

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 Total Garage and Parking Spaces: 6
Driveway - # of Spaces: 6
Asphalt Driveway
Driveway

Interior

Bedroom Information
# of Bedrooms On 1st Upper Level: 1
# of Bedrooms On Main Level: 3

Bathroom Information
# of Bathrooms (Full) On 1st Upper Level: 1
# of Bathrooms (Full) On Main Level: 3
# of Bathrooms (Full) On All Upper Levels: 1
# of Bathrooms (Full): 4

Interior Information
Appliances: Cooktop, Compactor, Dishwasher, Disposal, Extra Refrigerator/Freezer, Icemaker, Intercom, Oven - Wall, Water Heater, Microwave, Refrigerator, Stainless Steel Appliances, Washer/Dryer Stacked
Flooring Type: Carpet, Ceramic Tile, Hardwood, Luxury Vinyl Plank
Interior Features: Attic, Breakfast Area, Carpet, CeilngFan(s), Entry Level Bedroom, Family Room Off Kitchen, Formal/Separate Dining Room, Kitchen - Eat-In, Master Bath(s), Recessed Lighting, Stall Shower, Walk-in Closet(s), Window Treatments, Wood Floors, Bar, Built-Ins, Dining Area, Pantry, Wet/Dry Bar
Living Area Sq.Ft. Source: Estimated
Wall & Ceiling Types: Vaulted Ceilings, Cathedral Ceilings

Room Information
Dining Room, Master Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Kitchen, Game Room, Great Room, Laundry, Recreation Room, Master Bathroom, Full Bath
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
Ownership Interest: Fee Simple
Year Built Source: Assessor
Year Major Reno/Remodel: 2021

Building Information
Building Name: NONE AVAILABLE
Construction Materials: Frame, Stick Built, Vinyl Siding
Foundation Details: Block, Crawl Space
Main Entrance Orientation: East
Other Structures: Above Grade, Below Grade
Outdoor Living Structures: Deck(s), Patio(s), Porch(es), Roof, Wrap Around
Roof: Architectural Shingle
Structure Type: Detached
Window Features: Low-E, Screens
Other Structures: Shed

Exterior Information
Exterior Lighting, Flood Lights, Hot Tub, Outside Shower
Fencing: Rear, Vinyl, Picket

Pool Information
Personal Pool
In Ground

Lot Information
Lot Features: Landscaping, Rear Yard, Front Yard
Lot Size Dimensions: 125.00 x 200.00
Lot Dimensions Source: Assessor
Tidal Water: No

Above Grade Information
Finished Sq.Ft.: 3,284
Finished Sq.Ft. Source: Estimated

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

Financial

Tax Information
County Tax: $156
School Tax: $1,277
Tax Year: 2023
Tax Annual Amount: $1,431

Assessments Information
Year Assessed: 2023

Utilities

Utilities Information
Central Air
Cooling Type: Central A/C
Cooling Fuel: Electric
120/240V, 200+ Amp Service, Circuit Breakers, Underground
Forced Air
Heating Fuel: Propane - Leased
Hot Water: Propane
Sewer Septic: Public Sewer
Water Source: Well

Location

Homeowners Association Information
HOA/Condo/Coop Fee Includes: Common Area Maintenance, Road Maintenance
HOA/Condo/Coop Amenities: Boat Ramp
HOA Fee: $450
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: RT 24 to Banks Road. Enter Winding Creek Village, make a right onto Woodside Rd. Property will be on the right.

Public facts

Beds: 3
Baths: 3.0
Sq. Ft.: 2,067
Stories: 1.5
Lot Size: 0.57 acres
Style: Single Family Residential
Year Built: 1999
Year Renovated: —
County: Sussex County
APN: 234-24.00-273.00

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 • 1.3mi

5/10

Millsboro Middle School

Public 6-8 • Assigned • 7.4mi

4/10

Sussex Central High School

Public 9-12 • Assigned • 8.5mi

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

$593,000 – $718,000

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New listings for sale in 19966

NEW 10 HRS AGO

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1 John B Dr, Millsboro, DE 19966

Fenced-in backyard • Storage shed • Paved driveway

(302) 601-4171

COMING SOON

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NEW

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Manicured lawn • Open floor plan • Corian countertops

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NEW

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2 beds2 baths1,298 sq ft

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

Updated plumbing • Walk-in shower • Two decks

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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 448 Woodside Rd

Data from public records.

Address	Redfin Estimate
456 Woodside Road, Millsboro, DE 4 Beds \| 3.5 Baths \| 3142 Sq. Ft.	$844,626
457 Woodside Road, Millsboro, DE 3 Beds \| 3 Baths \| 2093 Sq. Ft.	$433,766
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
445 Woodside Road, Millsboro, DE 3 Beds \| 3 Baths \| 2654 Sq. Ft.	$477,438
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

Address	Redfin Estimate
452 Woodside Road, Millsboro, DE 3 Beds \| 4 Baths \| 2464 Sq. Ft.	$439,955
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
455 Woodside Road, Millsboro, DE 3 Beds \| 3 Baths \| 2013 Sq. Ft.	$452,864
446 Woodside Road, Millsboro, DE 3 Beds \| 2 Baths \| 2347 Sq. Ft.	$500,755
343 Pond Road, Millsboro, DE 4 Beds \| 5 Baths \| 1570 Sq. Ft.	$472,639
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
458 Woodside Road, Millsboro, DE 3 Beds \| 2 Baths \| 2016 Sq. Ft.	$507,517
449 Woodside Road, Millsboro, DE 3 Beds \| 2 Baths \| 2238 Sq. Ft.	$478,859
443 Woodside Road, Millsboro, DE 3 Beds \| 2 Baths \| 1474 Sq. Ft.	$356,484
442 Woodside Road, Millsboro, DE 3 Beds \| 2 Baths \| 2273 Sq. Ft.	$430,494
341 Pond Road, Millsboro, DE 3 Beds \| 2 Baths \| 1800 Sq. Ft.	$402,689
437 Grey Gull Lane, Millsboro, DE 3 Beds \| 2 Baths \| 2400 Sq. Ft.	$470,613

Property information provided by BRIGHT MLS when last listed in 2024. This data may not match . Learn more.

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About this home

Redfin Estimate

Earn from this home

Market trends in 19966, DE

Sale history for 448 Woodside Rd

Tax history for 448 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 448 Woodside Rd

More real estate resources