Would people walk alone at night in Cape Charles, VA?

As of early 2026, 95% of users say people would walk alone at night

Are yards well-kept in Cape Charles, VA?

As of early 2026, 93% of users say yards are well-kept

Is Cape Charles, VA walkable to restaurants?

As of early 2026, 92% of users say it's walkable to restaurants

Is parking easy in Cape Charles, VA?

As of early 2026, 89% of users say parking is easy

Does Cape Charles, VA have sidewalks?

As of early 2026, 88% of users say there are sidewalks

Does Cape Charles, VA show holiday spirit?

As of early 2026, 88% of users say there's holiday spirit

Is Cape Charles, VA dog-friendly?

As of early 2026, 85% of users say it's dog friendly

Do kids play outside in Cape Charles, VA?

As of early 2026, 84% of users say kids play outside

Do residents of Cape Charles, VA plan to stay at least 5 years?

As of early 2026, 80% of users say they plan to stay for at least 5 years

Is Cape Charles, VA quiet?

As of early 2026, 74% of users say it's quiet

Are there community events in Cape Charles, VA?

As of early 2026, 68% of users say there are community events

Are neighbors friendly in Cape Charles, VA?

As of early 2026, 65% of users say neighbors are friendly

Are the streets well-lit in Cape Charles, VA?

As of early 2026, 62% of users say streets are well-lit

Is a car needed in Cape Charles, VA?

As of early 2026, 54% of users say car is needed

Is there wildlife in Cape Charles, VA?

As of early 2026, 44% of users say there's wildlife

Is Cape Charles, VA walkable to grocery stores?

As of early 2026, 13% of users say it's walkable to grocery stores

What is 5259 Simpkins Dr estimated to be worth?

Trulia's estimated value for 5259 Simpkins Dr in Cape Charles, VA is $170,500 .

Is Cape Charles a buyer's or seller's market?

Cape Charles is currently a balanced market, based on recent for-sale activity.

What do residents say about Cape Charles?

Residents describe Cape Charles, VA as well-kept, walkable to restaurants, and easy to park in. See recently sold homes in Cape Charles, VA .

What are the closest schools to 5259 Simpkins Dr?

The closest schools to 5259 Simpkins Dr in Cape Charles, VA are Kiptopeke Elementary School (Pre-K, rated 4/10), Northampton High School (rated 2/10), Northampton Middle (rated 3/10).

How big is the lot at 5259 Simpkins Dr?

The lot at 5259 Simpkins Dr in Cape Charles, VA is about 0.50 acres (21,780 sq ft).

Does 5259 Simpkins Dr have a garage?

Yes, 5259 Simpkins Dr in Cape Charles, VA has a garage.

5259 Simpkins Dr, Cape Charles, VA 23310

OFF MARKET

$170,500

Trulia Estimate

5 Beds
2 Baths

5259 Simpkins Dr, Cape Charles, VA 23310

Est. Refi. Payment $1,033/mo*

Refinance Your Home

Home Value

Trulia Estimate

$171K

Since last month

$1K (-0.7%)

Since last year

$3K (+1.8%)

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 +82% in the last 10 years

Month	Estimated value
2026
August 2026	$172K
August 2026	$171K
July 2026	$173K
June 2026	$180K
May 2026	$167K
April 2026	$167K
March 2026	$165K
February 2026	$160K
January 2026	$146K
2025
December 2025	$157K
November 2025	$171K
October 2025	$169K
September 2025	$176K
August 2025	$169K
July 2025	$169K
June 2025	$161K
May 2025	$161K
April 2025	$149K
March 2025	$152K
February 2025	$153K
January 2025	$121K
2024
December 2024	$134K
November 2024	$139K
June 2024	$153K
May 2024	$131K
April 2024	$137K
2023
December 2023	$117K
October 2023	$120K
July 2023	$129K
May 2023	$112K
2022
September 2022	$122K
August 2022	$124K
July 2022	$130K
June 2022	$132K
May 2022	$130K
April 2022	$126K
February 2022	$72K
January 2022	$74K
2021
October 2021	$75K
September 2021	$74K
August 2021	$76K
June 2021	$80K
May 2021	$67K
April 2021	$70K
March 2021	$66K
2019
September 2019	$72K
August 2019	$90K
July 2019	$95K
June 2019	$81K
May 2019	$87K
April 2019	$82K
March 2019	$81K
February 2019	$83K
January 2019	$85K
2018
December 2018	$87K
November 2018	$93K
October 2018	$87K
September 2018	$79K
August 2018	$80K
July 2018	$82K
June 2018	$97K
May 2018	$103K
April 2018	$98K
March 2018	$92K
February 2018	$85K
January 2018	$107K
2017
December 2017	$106K
November 2017	$106K
October 2017	$102K
September 2017	$102K
August 2017	$102K
July 2017	$105K
June 2017	$106K
May 2017	$101K
April 2017	$101K
March 2017	$105K
February 2017	$103K
January 2017	$104K
2016
December 2016	$99K
November 2016	$98K
October 2016	$95K
September 2016	$95K

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
5332 Ramshorn Rd, Cape Charles, VA	0.22	Single-Family Home	$295,000	07/16/26		2	1,536
5065 Cobbs Station Rd, Cape Charles, VA	1.23	Single-Family Home	$255,000	10/03/25	3	2	1,273
5138 Cobbs Station Rd, Cape Charles, VA	1.28	Single-Family Home	$145,000	02/06/26	2	2	2,892
17063 Station Ln, Cape Charles, VA	1.80	Single-Family Home	$220,000	08/21/26	4	1.5	1,924
5349 Willow Oak Rd, Cape Charles, VA	1.88	Single-Family Home	$389,429	08/14/26	4	2	3,338
5317 Tyson Cir, Eastville, VA	1.97	Single-Family Home	$275,000	09/11/25	4	1.5	1,448
5317 Tyson Cir, Cape Charles, VA	1.98	Single-Family Home	$275,000	09/11/25	4	1.5	1,400
5337 Willow Oak Rd, Cape Charles, VA	1.91	Single-Family Home	$450,659	04/02/26	3	3	2,531
5376 Willow Oak Rd, Cape Charles, VA	1.81	Single-Family Home	$125,000	06/24/26	2	1	805
16349 Courthouse Rd, Cape Charles, VA	2.00	Single-Family Home	$269,000	07/02/26	3	2	3,381

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
5304 Ramshorn Rd, Cape Charles, VA 23310	0.21	$298,760	3	2	1,780	Recently Sold
5332 Ramshorn Ln, Eastville, VA 23347	0.22	$295,000	3	3	1,536	Recently Sold
19073 Lankford Highway, Cape Charles, VA 23310	0.51	$176,200	3	2	1,512	Off Market
18167 Meadows Dr, Cape Charles, VA 23310	0.47	$128,700	3	1	1,012	Off Market
LOTA Captain Howe Ln, Eastville, VA 23347	0.81	$249,900	-	-	-	For Sale
17492 Mc Cotter Lane Cpe, Cape Charles, VA 23310	0.83	$483,500	3	2.5	2,368	Off Market
Lot 10 The Landings Cpe, Charles, VA 23310	0.84	$464,990	3	2	2,185	For Sale
17501 McCotter Lane Cpe, Charles, VA 23310	0.94	$399,990	3	2	1,729	For Sale
17503 McCotter Lane Cpe, Charles, VA 23310	0.94	$444,990	3	3	2,107	For Sale
17500 McCotter Lane Cpe, Charles, VA 23310	0.97	$389,990	3	2	1,729	For Sale
Silverleaf, Cape Charles, VA 23310	0.98	$444,990+	3	3	2,107	-
Bramante Ranch, Cape Charles, VA 23310	0.98	$399,990+	3	2	1,729	-

Local Information

Map ViewExplore the area around 5259 Simpkins Dr.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Single-Family Home

0.5 acre lot

Garage

About this House

This single-family home is located at 5259 Simpkins Dr, Cape Charles, VA. 5259 Simpkins Dr is in Cape Charles, VA and in ZIP code 23310. This property has 5 bedrooms and 2 bathrooms. This property has a lot size of 0.50 acres.

5259 Simpkins Dr, Cape Charles, VA 23310 is a 5 bedroom, 2 bathroom single-family home. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $170,500, with a rent estimate of $2,370/month.

Home Details for 5259 Simpkins Dr

Interior Features
Levels, Entrance, & Accessibility Stories: 1

Property Information
Property Type / Style Property Type: Single Family Home

Exterior Features
Parking & Garage GarageParking: Carport, Garage Attached

Lot Information
Lot Area: 0.50 acres

Price and Tax history

Year	Property tax	Tax assessment
2024	$899	$131,200

Home facts updated by county records

Additional Cost

Market trends in Cape Charles

Last updated July 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

1MoM

Around this home

Kiptopeke Elementary School
PK-6
Public
300 Students
Northampton County Public Schools
4/10
GreatSchools Rating
Parent Rating Average
This school is a warm and wonderful place for children. My visit was fantastic - the students were engaged, the teachers were happy, and everyone was very welcoming. Test scores might be slightly lower than state average, but test scores are not the true measure of student learning. What I saw was student learning and growth!
Other Review
7y ago
4 Reviews

View nearby schools on GreatSchools

The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Cape Charles

At least 19 Trulia users voted on each feature.

95 % Say people would walk alone at night
93 % Say yards are well-kept
92 % Say it's walkable to restaurants
89 % Say parking is easy
88 % Say there are sidewalks
88 % Say there's holiday spirit
85 % Say it's dog friendly
84 % Say kids play outside
80 % Say they plan to stay for at least 5 years
74 % Say it's quiet
68 % Say there are community events
65 % Say neighbors are friendly
62 % Say streets are well-lit
54 % Say car is needed
44 % Say there's wildlife
13 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.

Amy Sabo
Resident
1y ago
"Great playground, great beach. Super safe neighborhood. My kids say they wish they had grown up here. "
0
Flag
Kelly
Visitor
2y ago
"Live music in Central Park on Sat nights in the summer, very friendly porch-sitters throughout the bayside town and 25 mph roadway that is golf-cart friendly making a more intimate community."
0
Flag
Shputzbulk
Resident
7y ago
"Parades, Concerts in the Park, Grand Illumination of Central Park, Guppie Challenge, New Roots Youth Garden, Epiphany Party, Dropping of the Crab Pot, Crabby Blues Festival"
4
Flag
JRJ
Resident
7y ago
"We have a weekend home in Cape Charles, and love the fact that we can walk to church, restaurants, drugstore, Palace Theatre, library, the beach, the park, etc! Plus there are fun events planned by the town during the year, such as the Fourth of July parade, Festive Fridays, and Dropping of the Crab Pot for New Year's Eve."
6
Flag
Jack F.
14y ago
"This is a great town for those looking for a quiet "Turn of the Century" Chesapeake Bay experience."
8
Flag

LGBTQ Local Legal Protections

Frequently asked questions about 5259 Simpkins Dr

What is 5259 Simpkins Dr estimated to be worth?
Trulia's estimated value for 5259 Simpkins Dr in Cape Charles, VA is $170,500.
Is Cape Charles a buyer's or seller's market?
Cape Charles is currently a balanced market, based on recent for-sale activity.
What do residents say about Cape Charles?
Residents describe Cape Charles, VA as well-kept, walkable to restaurants, and easy to park in. See recently sold homes in Cape Charles, VA.
What are the closest schools to 5259 Simpkins Dr?
The closest schools to 5259 Simpkins Dr in Cape Charles, VA are Kiptopeke Elementary School (Pre-K, rated 4/10), Northampton High School (rated 2/10), Northampton Middle (rated 3/10).
How big is the lot at 5259 Simpkins Dr?
The lot at 5259 Simpkins Dr in Cape Charles, VA is about 0.50 acres (21,780 sq ft).
Does 5259 Simpkins Dr have a garage?
Yes, 5259 Simpkins Dr in Cape Charles, VA has a garage.