OFF MARKET

Off market jun 2023 for $535K

$482,135

Est. refi paymentEst. refi $3,477/mo

•

2,000

sq ft

419 Circle Rd, Millsboro, DE 19966

About this home

Exceptionally maintained and lovingly cared for home located in the WATERFRONT community of Winding Creek Village! Bring your boat, jet ski or kayak and take advantage of your navigable WATER ACCESS! Community boat ramp/real water access! From this prime location you are only minutes to Baywood public golf course, area beaches, local waterways, shopping & restaurants! You can own (NO lot rent) the best of everything with this Beautiful maturely landscaped 1/2 acre property! Inside you will find 3 spacious bedrooms, an additional 4th bedroom/office, a generous sun room, and 2.5 baths! Kitchen is nicely appointed w/ SS appliances, Large farmhouse sink, Brand new refrigerator & Microwave, granite counters, custom cabinetry, center island & spacious dining area! Cozy up in your living area next to your wood burning fireplace! Your main living space opens up to the backyard which has a beautiful patio, perfect for BBQ's and entertaining! Hardwood floors flow throughout the main living areas! Main bedroom is located on the 1st floor & has a walk in closet complete with custom closet system! Main bathroom features a walk in tile shower and granite counters on a nice antique style cabinet. Laundry closet is conveniently located on the 1st floor with Brand new stackable washer/dryer. Other important features to note: most windows have been replaced over the last 10 years, crawl space has a concrete floor, dehumidifier and sump pump, this home has a Geothermal 2 loop system, a large shed fitted with water and electric! Easy to show! See it today! 72 hour kick out!

Single-familyProperty Type

1992Year Built

0.57 acresLot Size

$241Est. Price/Sq.Ft.

2 garage spacesParking

Listed by Debbie Reed • RE/MAX Realty Group Rehoboth

•302-227-4800 (broker)

•dolores@rehobothre.com (broker)

Listed by CARRIE HELLENS • RE/MAX Realty Group Rehoboth

•302-227-4800 (broker)

•dolores@rehobothre.com (broker)

Bought with Lee Ann Wilkinson • Berkshire Hathaway HomeServices PenFed Realty

•302-645-6661 (broker)

Redfin checked: 2 minutes ago

•Source:BRIGHT MLS #DESU2038956

Redfin Estimate

$482,135

$53K since sold in June 2023$6,000 since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 40.4% higher than the average sale price ($343K) of 6 comparable homes.

SOLD JUN 12, 2026
$525,000
A
3 beds2 baths2,016 sq ft
458 Woodside Rd, Millsboro, DE 19966
SOLD FEB 13, 2026
$505,000
B
3 beds2.5 baths2,142 sq ft
285 Pond Rd, Millsboro, DE 19966
SOLD SEP 18, 2026
$150,000
C
3 beds2 baths2,173 sq ft
25306 Crab Aly W #1506, Millsboro, DE 19966
SOLD SEP 28, 2026
$165,000
D
3 beds2 baths1,920 sq ft
33288 Arrowood Cv #2726, Long Neck, DE 19966
SOLD SEP 8, 2026
$313,000
E
3 beds2 baths1,890 sq ft
32589 Long Iron Way #3216, Millsboro, DE 19966
SOLD SEP 25, 2026
$402,500
F
3 beds2.5 baths1,769 sq ft
32393 Mariners Way, Millsboro, DE 19966

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Earn from this home

Sell

$50,376

Est. take-home

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Refinance

Est. cash available

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Rent

$3,217/mo

Redfin rental estimate

List your home for rent

Market trends in 19966, DE

Last updated September 2026

Buyer's Market

Seller's Market

Buyer's market

Sale-to-List Price

98.1%

0.5% MoM

Median sale price

$341K

$4K MoM

Avg. days on market

77d

7 days MoM

Recently sold homes

293

22 MoM

New listings for sale

COMING SOON
$429,900
3 beds2 baths1,732 sq ft
28943 Henry Pl E, Millsboro, DE 19966
(302) 644-2121
$353,000
3 beds2.5 baths1,890 sq ft
32581 Long Spoon Way #3281, Millsboro, DE 19966
(302) 945-6280
3D WALKTHROUGH
$275,000
3 beds2 baths1,488 sq ft
3306 Caitlins Way #3306, Millsboro, DE 19966
(302) 741-4545
144 Hudson Aly, Millsboro, DE 19966
$310,000
2 beds1.5 baths992 sq ft
144 Hudson Aly, Millsboro, DE 19966
(302) 644-2121
OPEN OCT 10, 10AM TO 11:30AM
$269,000
3 beds2 baths792 sq ft
27054 Trinity Rd, Millsboro, DE 19966
(302) 360-0300
$799,999
4 beds4 baths4,592 sq ft
32039 Ivory Gull Way, Millsboro, DE 19966
(302) 360-0300
$264,900
2 beds2.5 baths1,260 sq ft
20548 Asheville Dr, Millsboro, DE 19966
(302) 934-8818
OPEN OCT 10, 10AM TO 12PM
$419,000
5 beds3 baths2,128 sq ft
Millsboro, DE 19966
(302) 945-3820
$649,900
3 beds2 baths2,760 sq ft
28592 Dupont Blvd, Millsboro, DE 19966
(410) 677-0909
$865,000
3 beds3 baths2,756 sq ft
27063 Firefly Blvd #132, Millsboro, DE 19966
(302) 360-0300
See all

Provided by Redfin

Sale history for 419 Circle Rd

Date

Event

Price

BRIGHT MLS #DESU2038956

Jun 13, 2023

Sold

$535,000

$268/sq ft

Apr 19, 2023

Contingent

—

Apr 6, 2023

Listed

$525,000

$263/sq ft

Apr 5, 2023

Coming Soon

$525,000

$263/sq ft

BRIGHT MLS #DESU2024848

Sep 28, 2022

Sold

$500,000

$250/sq ft

Aug 16, 2022

Pending

—

Aug 16, 2022

Price Changed

$500,000

$250/sq ft

Jul 16, 2022

Contingent

—

Jul 3, 2022

Listed

$489,000

$245/sq ft

+47

Welcome to Winding Creek a beautiful waterfront community. Bring your boat, jet ski, canoe or paddle board and easily access the community boat ramp of which will take you out to enjoy all the various waterways for a fun filled day. This 4 bedroom - 2.5 baths offers you an easy lifestyle that has a beautiful first floor master bedroom with updated bath with walk in shower. Custom closet in the master bedroom. Kitchen was renovated with beautiful cabinetry and quartz countertops along with newer stainless steel appliances. The Dining area that looks out to the living room with a wood burning fireplace and also looks out to the sunroom addition that has a mini split system offering air conditioning and heat so that your always comfortable. From the sunroom you can head to the backyard to enjoy the outdoor entertaining area. You will also find a shed with water & electric already there. This home has a geothermal 2 loop system. Most windows in the home have been replaced within the last 10 years and new roof was installed in 2012. Crawlspace with finished cement floor with dehumidifier and sump pump for ac condenser. Public sewers are due to be installed in the near future (specific timing to be determined). Call your agent today to see this beautiful home before it's gone!

Public Records

Sep 29, 2008

Sold

$335,000

$168/sq ft

BRIGHT MLS #1000937352

Aug 26, 2008

Listing Removed

—

Apr 24, 2007

Listed

$360,000

$180/sq ft

Join or sign in to view all info

Year

Property tax

Land + Additions

Assessment*

2026

$1,057 (−0.4%)

$58,450 + $184,300

$242,750

2025

$1,061 (−5.9%)

$58,450 + $184,300

$242,750

2024

$1,128 (+2.3%)

$58,450 + $184,300

$242,750

2023

$1,103 (+64.4%)

$4,000 + $22,700

$26,700

2022

$671 (−0.9%)

$4,000 + $22,700

$26,700

2021

$676 (+7.7%)

$4,000 + $22,700

$26,700

2020

$628 (+0.7%)

$4,000 + $22,700

$26,700

2019

$624 (−1.5%)

$4,000 + $22,700

$26,700

2018

$634 (−1.3%)

$4,000 + $22,700

$26,700

2017

$642 (+13.8%)

$4,000 + $22,700

$26,700

2016

$564 (−38.5%)

$4,000 + $22,700

$26,700

2014

$917

$4,000 + $22,200

$26,200

Tax history for 419 Circle Rd

Year

Property tax

Land + Additions

Assessment*

2026

$1,057 (−0.4%)

$58,450 + $184,300

$242,750

2025

$1,061 (−5.9%)

$58,450 + $184,300

$242,750

2024

$1,128 (+2.3%)

$58,450 + $184,300

$242,750

2023

$1,103 (+64.4%)

$4,000 + $22,700

$26,700

2022

$671 (−0.9%)

$4,000 + $22,700

$26,700

2021

$676 (+7.7%)

$4,000 + $22,700

$26,700

2020

$628 (+0.7%)

$4,000 + $22,700

$26,700

2019

$624 (−1.5%)

$4,000 + $22,700

$26,700

2018

$634 (−1.3%)

$4,000 + $22,700

$26,700

2017

$642 (+13.8%)

$4,000 + $22,700

$26,700

2016

$564 (−38.5%)

$4,000 + $22,700

$26,700

2014

$917

$4,000 + $22,200

$26,200

*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

125 ft.

Lot depth

200 ft.

Lot size

0.57 Acres

Year renovated

—

Sq. Ft.

1,404

Year built

1992

Style

Single Family Residential

County

Sussex County

APN

234-24.00-242.00

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 - Side Entry, Garage Door Opener
# of Total Garage and Parking Spaces: 8
Has Garage
# of Garage Spaces: 2
Driveway - # of Spaces: 6
Attached Garage, Driveway

Interior

Virtual Tour

Bedroom Information
# of Bedrooms On 1st Upper Level: 2
# of Bedrooms On Main Level: 2

Bathroom Information
# of Bathrooms (Full) On 1st Upper Level: 1
# of Bathrooms (Half) On Main Level: 1
# of Bathrooms (Full) On Main Level: 1
# of Bathrooms (Full) On All Upper Levels: 1
# of Bathrooms (Half): 1
# of Bathrooms (Full): 2

Interior Information
Appliances: Built-In Microwave, Built-In Range, Dishwasher, Disposal, Dryer - Front Loading, Oven - Single, Washer - Front Loading, Water Heater, Oven/Range - Electric, Stainless Steel Appliances, Washer/Dryer Stacked, Refrigerator
Flooring Type: Ceramic Tile, Carpet, Hardwood, Engineered Wood
Interior Features: Attic, CeilngFan(s), Combination Kitchen/Dining, Entry Level Bedroom, Floor Plan - Traditional, Kitchen - Island, Tub Shower, Upgraded Countertops, Walk-in Closet(s), Window Treatments, Wood Floors
Living Area Sq.Ft. Source: Estimated

Fireplace Information
Has Fireplace
# of Fireplaces: 1
Heatilator, Wood

Basement Information
Basement: No

Exterior

Property Information
Not Federal Flood Zone
Total Below Grade Sq. Ft.: 0
Improvement Assessed Value: $22,700
Ownership Interest: Fee Simple
Property Condition: Very Good
Year Built Source: Estimated
Year Major Reno/Remodel: 2012

Building Information
Building Name: NONE AVAILABLE
Construction Materials: Frame, Brick, Stucco
Foundation Details: Block, Crawl Space
Other Structures: Above Grade, Below Grade
Pets Allowed: Yes
Pet Restrictions: Dogs OK, Cats OK
Roof: Architectural Shingle
Structure Type: Detached

Exterior Information
Underground Lawn Sprinkler

Lot Information
Lot Features: Landscaping
Tidal Water: No

Land Information
Land Assessed Value: $4,000

Above Grade Information
Finished Sq.Ft.: 2,000
Finished Sq.Ft. Source: Estimated

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

Financial

Tax Information
County Tax: $119
School Tax: $934
Tax Assessed Value: $26,700
Tax Year: 2021
Tax Annual Amount: $1,052

Assessments Information
Year Assessed: 2021

Lease Information
Lease Considered: No

Utilities

Utilities Information
Central Air
Cooling Type: Central A/C
Cooling Fuel: Geothermal
Other, Heat Pump - Electric BackUp
Heating Fuel: Geo-thermal
Hot Water: Other
Sewer Septic: On Site Septic
Water Source: Well

Location

Homeowners Association Information
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: From Entrance on Winding Creek Village follow straight until you see Circle Rd on your Right. 2nd house on the left on Circle Rd. Look for sign.

Public facts

Beds: 3
Baths: 3.0
Sq. Ft.: 1,404
Stories: 1.0
Lot Size: 0.57 acres
Style: Single Family Residential
Year Built: 1992
Year Renovated: —
County: Sussex County
APN: 234-24.00-242.00

Home facts updated by county records on Aug 24, 2026

Around this home

Schools

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 • 8.6mi

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

$459,000 – $555,000

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New listings for sale in 19966

COMING SOON

$429,900

3 beds2 baths1,732 sq ft

28943 Henry Pl E, Millsboro, DE 19966

(302) 644-2121

$353,000

3 beds2.5 baths1,890 sq ft

32581 Long Spoon Way #3281, Millsboro, DE 19966

(302) 945-6280

3D WALKTHROUGH

$275,000

3 beds2 baths1,488 sq ft

3306 Caitlins Way #3306, Millsboro, DE 19966

(302) 741-4545

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2 beds1.5 baths992 sq ft

144 Hudson Aly, Millsboro, DE 19966

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OPEN OCT 10, 10AM TO 11:30AM3D WALKTHROUGH

$269,000

3 beds2 baths792 sq ft

27054 Trinity Rd, Millsboro, DE 19966

(302) 360-0300

$799,999

4 beds4 baths4,592 sq ft

32039 Ivory Gull Way, Millsboro, DE 19966

(302) 360-0300

$264,900

2 beds2.5 baths1,260 sq ft

20548 Asheville Dr, Millsboro, DE 19966

(302) 934-8818

OPEN OCT 10, 10AM TO 12PM

$419,000

5 beds3 baths2,128 sq ft

Millsboro, DE 19966

(302) 945-3820

$649,900

3 beds2 baths2,760 sq ft

28592 Dupont Blvd, Millsboro, DE 19966

(410) 677-0909

Home values near 419 Circle Rd

Data from public records.

Address	Redfin Estimate
413 Circle Road, Millsboro, DE 3 Beds \| 3 Baths \| 2000 Sq. Ft.	$402,941
401 Circle Road, Millsboro, DE 4 Beds \| 2.5 Baths \| 4200 Sq. Ft.	$699,995

Address	Redfin Estimate
402 Circle Road, Millsboro, DE 3 Beds \| 3 Baths \| 1482 Sq. Ft.	$368,011
418 Circle Road, Millsboro, DE 3 Beds \| 3 Baths \| 2275 Sq. Ft.	$444,294

Address	Redfin Estimate
420 Circle Road, Millsboro, DE 3 Beds \| 2 Baths \| 1700 Sq. Ft.	$413,515
403 Circle Road, Millsboro, DE 4 Beds \| 3 Baths \| 3000 Sq. Ft.	$525,541

Property information provided by BRIGHT MLS when last listed in 2023. This data may not match . Learn more.

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Redfin Estimate

Earn from this home

Market trends in 19966, DE

Sale history for 419 Circle Rd

Tax history for 419 Circle 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 419 Circle Rd

More real estate resources