27356 Cheapside Rd, Cape Charles, VA 23310
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Property image
OFF MARKET

27356 Cheapside Rd
Cape Charles, VA 23310

  • 4 Beds
  • 2 Baths
  • 2,280 sqft (on 1.31 acres)
4 Beds
2 Baths
2,280 sqft
(on 1.31 acres)

Local Information

  • Map ViewExplore the area around 27356 Cheapside Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1754
Lot Size
1.31 acres
Living Area
2,280 sqft

About this House

Are you looking for a property close to the Chesapeake Bay Bridge and Tunnel and Kiptopeake State Park? House is occupied. It could be a vacation property or your home away from home.
27356 Cheapside Rd, Cape Charles, VA 23310 is a 4 bedroom, 2 bathroom, 2,280 sqft single-family home built in 1754. It is currently off market. The Trulia Estimate rent is $2,050/month.
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Home Details for 27356 Cheapside Rd

Interior Features

Heating & Cooling
Heating: ElectricAir ConditioningCooling System: Wall Unit SHeating Fuel: Electric

Property Information

Year Built
Year Built: 1754
Property Type / Style
Property Type: Single Family Home

Media

See Virtual Tour: http://.exitrealty.com/listing-tour/varein:10377646

Lot Information

Lot Area: 0.00 Acres

Price History for 27356 Cheapside Rd

DatePriceEventSource
04/01/2024$100,000ListingRemovedExit Realty #10377646
06/03/2022$100,000ContingentExit Realty #10377646
06/21/2021$100,000PendingEastern Shore AOR #53813
06/21/2021$100,000ContingentREIN Inc. #10377646
05/17/2021$100,000Listed For SaleEastern Shore AOR #53813

Market trends in Cape Charles

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
82
8MoM
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Property Tax and Assessment

Year2024
Tax$806
Assessment$117,700
Home facts updated by county records

Comparable Sales for 27356 Cheapside Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
3325 Sherwood Gate Cpe, Cape Charles, VA
0.42
Single-Family Home
$435,000
08/12/25
4
2.5
2,464
3134 Sapphire Court Cpe, Cape Charles, VA
0.57
Single-Family Home
$448,000
07/31/26
4
2
1,893
3269 Sherwood Gate Cpe, Cape Charles, VA
0.54
Single-Family Home
$440,000
05/27/26
4
3
2,005
3315 Sherwood Gate Cpe, Cape Charles, VA
0.43
Single-Family Home
$374,900
01/02/26
3
2
1,550
27192 Castle Row Cpe, Cape Charles, VA
0.49
Single-Family Home
$390,000
05/18/26
3
2
1,367
3339 Sherwood Gate, Capeville, VA
0.61
Single-Family Home
$374,900
03/10/26
3
2
1,550
27212 Castle Row Cpe, Cape Charles, VA
0.60
Single-Family Home
$395,000
11/21/25
3
2
1,367
2453 Sand Hill Dr, Cape Charles, VA
1.05
Single-Family Home
$760,000
08/28/25
4
2
2,770
27151 Castle Row Cpe, Cape Charles, VA
0.49
Single-Family Home
$325,000
01/22/26
3
2
1,149
27262 Seaside Rd, Capeville, VA
1.15
Single-Family Home
$135,500
06/08/26
4
1
1,780

Nearby homes

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Assigned Schools

These are the assigned schools for 27356 Cheapside Rd.
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
    "Great playground, great beach. Super safe neighborhood. My kids say they wish they had grown up here. "
    0
    Flag
  • Kelly
    "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
    "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
    "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.
    "This is a great town for those looking for a quiet "Turn of the Century" Chesapeake Bay experience."
    8
    Flag

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Apartments for Rent

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Explore by feature - Air Conditioning

6 rentals with air conditioning in Cape Charles, VA

Homes for sale near 27356 Cheapside Rd

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Off Market Homes Near 27356 Cheapside Rd

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