Chesapeake Properties

05/29/2026

If you've been eyeing a second home or a full relocation to Cape Charles, you're in good company (a lot of our buyers come from out of state). 🌊

But buying property in Virginia when you're not familiar with how the state handles real estate can feel like showing up to a game without knowing the rules. Contract structures, closing processes, disclosure laws ... they're all a little different here than what you might be used to.

We wrote a straightforward guide that breaks down exactly what's different so you can go into the process informed, not caught off guard.

Whether you're buying a weekend escape on the Eastern Shore or planning a full move, this is worth a read before you start making offers.

🔗 https://chesapeakeproperties.com/buying-a-home-in-virginia-as-an-out-of-state-buyer-whats-different/

Buying a home in Virginia as an out-of-state buyer? Learn what’s different about contracts, disclosures, taxes, and closing.

05/29/2026

Some properties you have to see to believe. 5302 Kendall Grove Point is one of them.

Set on 4.2 acres at the tip of a private point in Eastville, this 4,800 sq. ft. waterfront estate has been a fixture of Eastern Shore life since the 1950s, featured twice on the Garden Club of Virginia's annual tour and included in a book of Eastern Shore architecture. Built by legendary craftsman Hiawatha Wyatt, the craftsmanship alone is worth the visit.

Five bedrooms, five and a half baths, a 25×50 pool, deep-water dock on Mattawoman Creek, and water visible from every single window. Sunsets facing west over the Chesapeake Bay. Blue herons, striped bass, and blue crabs practically in your backyard.

See for yourself ... then reach out to Kim Starr at 757-635-0711 to schedule a showing. Offered at $2,200,000.

📍 Eastville, VA | Northampton County | Just 10 minutes from Cape Charles

https://chesapeakeproperties.idxbroker.com/idx/details/listing/b611/71528/5302-Kendall-Grove-Point-Ln-C1-Eastville-VA-23347?widgetReferer=true

05/28/2026

Want to build your own home in Cape Charles from the ground up? You're not alone — and it's absolutely doable. But the process is more involved than most buyers expect going in. 🏡

A few things worth knowing before you purchase a lot:

✔️ Zoning is set by the town, not the county (and some districts have design requirements down to rooflines and porch depth)
✔️ Utility access depends on where the lot sits; not every parcel has water and sewer nearby
✔️ Coastal location means floodplain and wetlands checks are part of the picture
✔️ Land prep, impact fees, and pre-construction costs add up quickly on top of build costs

If you've been eyeing a vacant lot on the Eastern Shore, this guide is a solid starting point.

🔗 https://chesapeakeproperties.com/build-on-land-in-cape-charles-zoning-utilities-and-costs/

Can you build on vacant land in Cape Charles? Learn how zoning, utilities, and construction costs affect whether a lot is truly buildable.

05/27/2026

Thinking about buying in Cape Charles but wondering how the market holds up when things get uncertain? 📉➡️📈

A few things work in this town's favor that most markets don't have: limited land, no room for large-scale new development, and buyers who buy to stay—not to flip.

We wrote about what historically protects Cape Charles home values during downturns, which property types tend to hold up best, and how to think about a purchase here with a long-term lens.
Worth a read if you're doing your homework before buying.

🔗 https://chesapeakeproperties.com/cape-charles-home-values-during-market-downturns/

Do Cape Charles home values hold up during market downturns? See what helps protect pricing stability on the Eastern Shore.

05/27/2026

🏡 PRICE IMPROVEMENT | 5445 Milford Rd, Cape Charles

This one just got even more compelling. 5445 Milford Road, a one-of-a-kind waterfront retreat on Mockhorn Bay, is now $725,000.

That's 5+ acres, panoramic barrier island views, a private boathouse, and a 2,035 sq. ft. lodge built in 1923 with the kind of bones and character you simply can't replicate. Three bedrooms, three baths, multiple fireplaces, and the sort of sunrises that make you forget you own a phone.

Whether you're dreaming of a private escape, an adventurer's base camp, or a waterfront property with serious presence, this is your moment.

📍 Cape Charles, VA | 3 BD | 3 BA | 2,035 sqft | 5.36 Acres | Waterfront on Mockhorn Bay

🔗 https://www.zillow.com/homedetails/5445-Milford-Rd-Cape-Charles-VA-23310/447901559_zpid/?utm_campaign=zillowwebmessage&utm_medium=referral&utm_source=txtshare

📞 Penney Holland Realtor | 757-641-9753

This 2035 square feet Single Family home has 3 bedrooms and 3 bathrooms. It is located at 5445 Milford Rd, Cape Charles, VA.

05/26/2026

Dreaming of waking up to Chesapeake Bay views every morning? 🌅 Before you decide, there's more to consider than the scenery.

Bayfront homes command a premium and often hold it well. But flood insurance, wind coverage, and salt air take a real toll on ownership costs. Inland homes tend to offer more stability, space, and breathing room in your budget.

Both can be great investments. The key is knowing which one aligns with how you plan to use it and how long you plan to own it.

We put together a no-fluff guide to help you think it through 👇

Comparing bayfront vs inland homes on the Eastern Shore? Learn how location affects value, maintenance, insurance, and resale over time.

05/23/2026

🏡 OPEN HOUSE TODAY
714 Monroe Ave, Cape Charles
10 AM – 5 PM

Gray skies? Perfect excuse to come tour one of Cape Charles’ newest and most beautiful homes! ☁️

This brand-new coastal modern beauty just hit the market at $955,000 and checks every box — 4 bedrooms, 3 full baths, 2,080 sq ft of thoughtfully designed living space, oak floors throughout, and a gourmet kitchen built to impress.

A few things to love:
✨ First-floor primary suite
🌿 Screened porch + front porch overlooking the pond
⚡ High-performance Bosch mechanical system with ERV ventilation
🏖️ 7 blocks to the beach, 4 blocks to Mason Ave
🛺 Golf cart friendly neighborhood

Built with CertainTeed’s One Precision Assembly system — all the charm of coastal living, none of the headaches of an older home. This one is truly move-in ready.

Stop by today for a Bellini, Mimosa, or sparkling wine as you tour this beauty!

📍 714 Monroe Ave, Cape Charles, VA
🕙 Open today 10 AM – 5 PM
💰 Listed at $955,000

Questions? Contact Kim Starr (757-635-0711). 🏠

05/22/2026

Happy Memorial Day! In honor of those who are no longer with us please stop by and grab a duck!
We are also congratulating our graduates! Swing by and get yourself a hat!

05/22/2026

Its official! The first ducks of the season are out and ready to be found!!🌷🐣☀️

05/20/2026

One of Cape Charles's most iconic estates has just hit the market ... and she is stunning.

This 1927 Colonial Revival grand dame on Bay Avenue offers 5,158 sq. ft. of beautifully preserved history with sweeping Chesapeake Bay views and those legendary western-exposure sunsets every single evening. 🌅

6 bedrooms | 4.5 baths | Triple brick Flemish bond construction | Attached 2-car garage | Two lots on a prime corner site

The details will stop you in your tracks—arched porticos, chippendale balcony railings, a grand entry staircase, an 18-foot formal dining room with butler's pantry, and a renovated gourmet kitchen that blends historic charm with modern convenience. The sun porch, front porch, backyard fireplace, and fully fenced hardscaped yard make this a home built for living and entertaining beautifully.

🏡 Being sold fully furnished as a turnkey vacation rental—all bookings convey.

💰 Assumable VA mortgage at 2.25%—a rare and significant financial advantage in today's market.

Walk to the white sandy beach, the promenade, the pier, restaurants, galleries, and live theater. Golf cart community. This is Cape Charles living at its absolute finest.

Listed at $2,300,000

📞 Contact Kim Starr at 757-635-0711 or view the full listing here → https://chesapeakeproperties.idxbroker.com/idx/details/listing/b611/71430/212-Bay-Ave-9A-Cape-Charles-VA-23310

05/20/2026

Bought a home in Cape Charles as a personal getaway but now you're wondering if renting it out could make sense? You're not alone, and the short answer is: it's usually possible. But there's more to it than just listing it on Airbnb. 🏡

Cape Charles has specific short-term rental regulations, and whether your property is inside town limits or in Northampton County makes a difference. On top of that, HOA restrictions, your original mortgage terms, insurance classification, and local lodging tax requirements all come into play the moment you shift from personal use to rental use.

The good news is that a lot of Cape Charles buyers move through different phases (vacation home, occasional rental, full-time rental, and eventually a permanent move) and that flexibility is part of what makes buying here appealing. The key is knowing what to plan for before you make the switch.

We put together a practical guide covering everything to think through if renting your Cape Charles property is on your radar, now or down the road.

👉 https://chesapeakeproperties.com/renting-your-home-in-cape-charles-what-happens-if-you-decide-later/

4.6

Renting your home in Cape Charles later? Learn how zoning, HOA rules, taxes, insurance, and mortgages affect converting to a rental.