Jarrett Caldwell Real Estate Agent

Jarrett Caldwell Real Estate Agent If You Are Looking to Buy or Sell...Don't Forget to Call Jarrett Caldwell🏠 His experience includes personalized digital marketing and advertising.

Jarrett Caldwell began his real estate career in 2008 as a real estate investor with JMD Elite Services, LLC. As a military spouse with over 20 years of active duty service, Jarrett has been able to tap into the real estate market in multiple states. By 2017, Jarrett decided to start a career representing both buyers and sellers with the acquisition of homes, buildings, and commercial and residential land. With a B.A Degree in Marketing from Tiffin University, his background in real estate investment was an added bonus. He strives in keeping up with the newest technology and abreast of the changes in the real estate market. Jarrett Caldwell is a great realtor and I would highly recommend him to someone who is looking for a realtor. He is always willing to help and is on top of everything. You can call or text him at any time during the day or night and he will get back to you very quickly so he is very reliable. He did a very good job in helping my wife and I find our lovely home and we truly appreciate everything he has done for us during our process of house hunting. - David

From the start of his career and in the past few years, Jarrett has been specializing in military moves, First Time Home Buyer's and the programs available to First Time Home Buyers for new Airmen, Soldiers, Sailors, and Marines. Jarrett created guidelines to assist military members in the structured timeline of buying and selling within the confines of the rigorous permanent change of duty station for military families as smoothly as possible. Jarrett and his military wife, Kerrin, are world travelers, raising two active little boys, Mateo and Dominic. He believes in leaving a legacy for his children, as they are the leaders of tomorrow. In his spare time, Jarrett is an avid poker player and vocal musician, who sings as a Praise and Worship Leader for his church and as a part-time, background vocalist to professional artists.

09/12/2026

You’re the realtor today. Walk this one with me and lock in your number before I reveal it. 🏠

While you’re checking out the countertops and bedrooms, I’m looking at condition, layout, what needs inspecting, and what comparable homes are actually selling for, because liking a house and liking the deal are two very different things. There’s also one bonus space toward the back that’s going to split opinions hard, some will see a cozy home office, others will see nothing but renovation cost.

Lock in your number before you get to the reveal, then drop it in the comments, no cheating after you find out. 👇

💾 Save this and send it to the friend who thinks they’re a realtor from six months on Zillow.
📤 Share with someone house hunting right now.
📞 Buying or selling in Hampton Roads? Call Jarrett Caldwell.

09/11/2026

Chalk another one up for the good guys!! Serving another Military Veteran with their Dream Home

09/10/2026

🚕 $30K: Tesla or Real Estate? 🏠

Same money. Two completely different investments.

Which one are YOU choosing—and why? 👇🏾

09/09/2026

🥩 Apparently y’all enjoyed arguing with me about brunch…so let’s do it again. 😂

My Top 5 places to get a steak in Hampton Roads. And yes…I’ve been training for this list. 😂

Think I got it wrong? Tell me what I missed AND what steak I need to order. 👇🏾

💾 Save this for your next date night.
📤 Share it with your steak partner.
➕ Follow for more Hampton Roads content.

And if you’re looking to buy or sell in Hampton Roads, don’t forget to call Jarrett Caldwell.

#757

09/08/2026

Hampton isn’t just repaving North Armistead Avenue, they’re literally raising it. 🚧

Roughly half a mile between Convention Center Drive and New Market Creek Bridge is being lifted over 5 feet to fight chronic flooding, plus new sidewalks and a shared use path connecting into the Water Walk trail. It’s a two year project, and traffic is already down to one lane each way, but fixing infrastructure that floods every storm, that’s the elite move.

If you drive Armistead regularly, is the finished result worth two years of construction? 👇

💾 Save this for future reference.
📤 Share with someone who drives Armistead.
📞 Buying or selling in Hampton Roads? Call Jarrett Caldwell.

Happy Labor Day to everyone who's put in the work, whatever that work looks like. 🇺🇸Hampton Roads runs on people who sho...
09/07/2026

Happy Labor Day to everyone who's put in the work, whatever that work looks like. 🇺🇸

Hampton Roads runs on people who show up, from military families to skilled trades to small business owners keeping this region moving. Today's about taking a breath and enjoying it with the people who matter most.

09/06/2026

An appraisal coming back lower than your offer isn’t the end of the deal, but it does start a whole new conversation. 🏠

Lenders want an independent valuation before financing anything, and when that number lands below the agreed price, buyers, sellers, and lenders all have to figure out who covers the gap, whether that’s a price adjustment, a shared middle ground, or the buyer bringing extra cash. And don’t confuse it with an inspection either, one looks at condition, the other is strictly about value for the lender, knowing the difference before it happens is the elite move.

If your dream house appraised $15,000 under your offer, would you pay the difference, renegotiate, or walk away? 👇

💾 Save this for when you start buying.
📤 Share with someone house hunting right now.
📞 Buying or selling? Call Jarrett Caldwell.

09/04/2026

New data shows just how easy it is to become house poor right now, and it’s not even about the mortgage. 🏠

A recent affordability report puts mortgage costs at 36% of a typical household’s income, and that’s before groceries, kids, daycare, or a car payment enter the picture. The real question isn’t the max you’re approved for, it’s the monthly payment that still lets you actually live your life, that’s the elite move ⭐.

Buyers, would you rather buy less house and keep more lifestyle, or stretch the budget for the house you really want? 👇

💾 Save this before you start house hunting.
📤 Share with someone thinking about buying.
📞 Wondering what you can actually afford? Message Jarrett Caldwell before you start looking.

09/03/2026

Chesapeake has a new development coming, but the homes aren’t even the part that caught my attention. 🏗️

Beyond the new housing mix planned off South Battlefield Boulevard, there’s a separate section built around food trucks, gathering spots, trails, and a pool, basically an attempt at an actual walkable community instead of just another subdivision. Sounds great until you’re the one living there every time a food truck line backs up your street on a Friday night.

Chesapeake folks, would something like this make you more interested in the neighborhood, or would you rather keep the activity somewhere else? 👇

💾 Save this, I’m tracking this project as it develops.
📤 Send it to someone who lives in Chesapeake.
📞 Buying or selling? Call Jarrett Caldwell.

Alright elites, before you start packing everything into boxes, you need to see these. 📦👀These are 5 simple moving hacks...
09/02/2026

Alright elites, before you start packing everything into boxes, you need to see these. 📦👀

These are 5 simple moving hacks that can make the whole process a little easier, from color-coding your rooms and protecting your dishes to moving your clothes without taking them off the hangers.

Some of these are so simple you’ll probably wonder why you never thought of them. 😂

Which hack are you trying on your next move? And what moving tip would you add to the list? 👇

💾 Save this for your next move.
📤 Send this to someone who's getting ready to pack.
🏡 Buying or selling in Hampton Roads? Call Jarrett Caldwell.

Address

3207 Churchland Boulevard
Chesapeake, VA
23321

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