A TIMELESS LEGACY AWAITS.
Step back to an era of craftsmanship and enduring style. Built in 1937, this magnificent brick Georgian home is a rare gem on the Eastern Shore, offering a living experience that no new construction can replicate. With its impressive scale and architectural details, this isn't just a house; it's a legacy property waiting for a new steward to write its next chapter. The home welcomes you through its original, oversized wood front door, framed by sidelights and a graceful fanlight. Inside, a grand entryway with a sweeping staircase and a long hallway sets a tone of classic elegance. The first floor boasts soaring 10-foot ceilings, enhancing the sense of space and light. Entertain family and friends in the formal dining room. Relax by the large fireplace in the living room, perfect for gathering on cool evenings. Historic details abound, including a slate roof, keystones over the windows, and working wood shutters. The original glass windows feature custom architectural grids in the top panes, a testament to the home's heritage. A butler's pantry off the kitchen, a Georgian hyphen connecting to the back entrance, and an enclosed back porch add to the home's conveniences.
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The home offers 4 bedrooms, a bonus room, and two and a half baths, providing ample space for family and guests. Three bedrooms are located on the second floor, along with a unique trunk room. Additional rooms are on the third floor, including 1-2 bedrooms, a storage room, and a bathroom with a claw foot bathtub.
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Enjoy the peaceful neighborhood from the expansive covered front porch. A second-floor balcony overlooks the backyard, offering the perfect spot for morning coffee, birdwatching, or a quiet moment to watch the sunset. A small covered porte cochere provides easy access to the basement. A new HVAC system provides efficient heating and AC. The original radiators have been thoughtfully left in place for those who appreciate their historic charm, offering the option to restore a classic heating system.
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Outside the home, the property offers immense potential. The almost two acres of land are a blank canvas for your dreams. This generous plot allows you to create a grand estate garden, build additional structures, or simply enjoy the open space and privacy. This is a rare opportunity to design an outdoor sanctuary that complements the home's timeless elegance.
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This unique home is located in the charming town of Cheriton, just outside the popular beach town of Cape Charles, with easy access to both the seaside for the Atlantic Ocean and bayside for the Chesapeake Bay. This home is a true gem, offering a perfect blend of historic charm and comfortable living in a beautiful and convenient location. This is a property for a discerning buyer who values history, space, and the opportunity to create a truly one-of-a-kind homestead.
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Serious inquiries only. Showings are available by appointment only. All showing requests must be accompanied by a pre-approval letter from a lender or a proof of funds statement.
For sale by owner
$490,000
21158 N Bayside Rd, Cape Charles, VA 23310
4beds
2,900sqft
Est.:
SingleFamily
Built in 1937
1 Acres Lot
$-- Zestimate®
$169/sqft
$-- HOA
What's special
Bonus roomUnique trunk roomSlate roofMagnificent brick georgian homeKeystones over the windowsEnclosed back porchExpansive covered front porch
What the owner loves about this home
The timeless classic style, the solid strong home, and the incredible surrounding land.
- 24 days |
- 1,596 |
- 81 |
Listed by:
Property Owner (757) 695-8245
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 3
- Full bathrooms: 2
- 1/2 bathrooms: 1
Heating
- Forced air, Electric
Cooling
- Central
Appliances
- Included: Dryer, Microwave, Range / Oven, Refrigerator, Washer
Features
- Flooring: Hardwood
- Basement: Unfinished
- Has fireplace: Yes
Interior area
- Total interior livable area: 2,900 sqft
Property
Parking
- Parking features: Carport, Garage - Attached
Features
- Exterior features: Brick
Lot
- Size: 1 Acres
Details
- Parcel number: 084C203000000003
Construction
Type & style
- Home type: SingleFamily
Materials
- Roof: Slate
Condition
- New construction: No
- Year built: 1937
Community & HOA
Location
- Region: Cape Charles
Financial & listing details
- Price per square foot: $169/sqft
- Tax assessed value: $369,100
- Annual tax amount: $2,528
- Date on market: 1/28/2026
Estimated market value
Not available
Estimated sales range
Not available
$2,546/mo
Price history
Price history
| Date | Event | Price |
|---|---|---|
| 1/28/2026 | Listed for sale | $490,000$169/sqft |
Source: Owner Report a problem | ||
| 12/23/2025 | Listing removed | -- |
Source: Owner Report a problem | ||
| 8/29/2025 | Listed for sale | $490,000+9.4%$169/sqft |
Source: Owner Report a problem | ||
| 8/28/2025 | Listing removed | $2,700$1/sqft |
Source: Zillow Rentals Report a problem | ||
| 6/16/2025 | Price change | $2,700-12.9%$1/sqft |
Source: Zillow Rentals Report a problem | ||
| 5/11/2025 | Price change | $3,100-6.1%$1/sqft |
Source: Zillow Rentals Report a problem | ||
| 4/26/2025 | Listed for rent | $3,300$1/sqft |
Source: Zillow Rentals Report a problem | ||
| 11/5/2024 | Listing removed | $448,000$154/sqft |
Source: | ||
| 4/22/2024 | Price change | $448,000+12.3%$154/sqft |
Source: | ||
| 5/19/2022 | Pending sale | $399,000$138/sqft |
Source: | ||
| 5/18/2022 | Contingent | $399,000$138/sqft |
Source: | ||
| 11/3/2021 | Listed for sale | $399,000$138/sqft |
Source: | ||
Public tax history
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | $2,528 -2.5% | $369,100 +8.2% |
| 2023 | $2,593 | $341,200 |
| 2022 | $2,593 +59.7% | $341,200 +75.5% |
| 2021 | $1,623 | $194,400 |
| 2020 | $1,623 -1% | $194,400 -1.6% |
| 2019 | $1,639 | $197,500 |
| 2018 | $1,639 | $197,500 |
| 2017 | -- | $197,500 -1% |
| 2016 | -- | $199,500 |
| 2015 | -- | $199,500 -17.9% |
| 2011 | -- | $243,100 |
| 2010 | -- | $243,100 |
Find assessor info on the county website
BuyAbility℠ payment
Est. payment
$2,587/mo
Principal & interest
$2338
Property taxes
$249
Climate risks
Neighborhood: 23310
Nearby schools
GreatSchools rating
- 4/10Kiptopeke Elementary SchoolGrades: PK-6Distance: 2.7 mi
- 4/10Northampton MiddleGrades: 7-8Distance: 5.2 mi
- 3/10Northampton High SchoolGrades: 9-12Distance: 5.2 mi




