Chesapeake, Virginia · Compassionate real estate guidance
A home transition?Let’s find your way forward.
Helping a loved one move, managing an inherited home, or simply unsure what comes next? Kristin helps Chesapeake families explore their options—with clarity, patience, and care.
No pressure. No obligation. A conversation is a place to start.
(757) 500-0264Support for families
A path shaped around your situation.What do you need?
Let’s find a way forward.
A move, an inherited home, or an estate can bring a lot to manage. We’ll compare the options around your family, the property, and your priorities.
Property decisions. Human considerations.Senior transitions
When a move involves downsizing, relocation, belongings, vendors, timelines, and family coordination.
Probate & estates
When the property is part of an estate and practical next steps need to follow the legal process.
Inherited properties
When heirs need room to compare keeping, preparing, renting, or selling the home.
Sell as-is
When speed, simplicity, or property condition makes a traditional listing less practical.
Cleanout & relocation
When belongings, vendors, timelines, and the move itself need thoughtful coordination.
Explore the area
Everything you need,
close to home.
From medical care and schools to libraries and everyday essentials, explore useful places around Chesapeake as you plan your next chapter.
A supportive community.
Every step of the way.
Map results, routes, hours, and availability may change. Open a location for current details.
Your guide through the moving pieces
A conversation
with Kristin Allen.
Kristin begins by listening: what is changing, what matters to your family, and what feels hardest to manage.
Through Driven2 Solutions and her affiliation with Next Chapter Services, she helps coordinate property decisions, cleanouts, relocation needs, and trusted professional connections.
You work directly with Kristin: a conversation, a property review, a comparison of options, then help coordinating your chosen next steps.
- 35+
- Families helped
- 8+
- Years of experience
- 100+
- Trusted professionals
Our community
Events this season.
Stay connected to Chesapeake. A creative afternoon, an evening of live music—a little something to look forward to.
Pumpkin Patch and Fall Festival at Hickory Ridge Farm
Pumpkin season at Hickory Ridge Farm, open every day, with hayrides, a barrel train, and weather-permitting pony rides. See the organizer’s page for hours.
Event details & registration Image courtesy of the linked event organizer.
Chesapeake Virginia Wine Festival
The 16th annual Chesapeake Wine Festival, an open-air afternoon of tastings at City Park. See the organizer’s page for tickets.
Event details & registration Image courtesy of the linked event organizer.
Halloween at The Museum
A family Halloween day at the museum, with costumes welcome. Activities are included with museum admission, and children five and under are free.
Event details & registration Image courtesy of the linked event organizer.
History Speaks: Bill Rose as General Cornwallis
The History Speaks lecture series continues with Bill Rose interpreting General Charles Cornwallis. See the museum’s page for the time and seating.
Event details & registration Image courtesy of the linked event organizer.
Chesapeake Jubilee Fall Craft Market
More than 100 crafters and direct sellers at City Park, with food and drink on site. See the organizer’s page for details.
Event details & registration Image courtesy of the linked event organizer.
Veterans Day Ceremony
The City of Chesapeake’s annual ceremony honoring veterans and showing appreciation for all who serve and have served.
Event details & registration Image courtesy of the linked event organizer.Selected events checked September 26, 2026. Past events disappear automatically. Events are hosted by independent organizers; follow their links for tickets and schedule updates.
Home & property in Chesapeake
The Chesapeake picture.
Where to start.
Chesapeake has the highest homeownership rate of the seven cities we serve: 74.4% of occupied homes are owner-occupied. With 255,332 residents it is the second-largest of the seven, and its median home value is $378,400.
When most families own, a transition often starts with a whole house to sort through. We plan the cleanout and the move alongside the sale decision, so the timeline works for whoever is doing the sorting.
- 255,332
- Residents
- 14.6%
- Aged 65 and over
- 74.4%
- Homes owner-occupied
- $378,400
- Median home value
Official pages for Chesapeake property
The city and court offices that handle probate, assessments, bulk pickup and flood zones. Check each for current hours and requirements.
Chesapeake Circuit Court Clerk · Probate
Call for an appointment with a probate clerk before going in, and complete the Application for Probate Appointment first.
Real Estate Assessor’s Office · Assessments
Find a Chesapeake home’s current assessment on the city’s Property Information Website, along with historic assessments and tax rates.
Chesapeake Waste Management · Bulk trash
Request a bulk pickup online by 11:59 p.m. the day before your collection day, or by phone by 5 p.m. the workday before. Construction and demolition debris is not collected.
City of Chesapeake · Floodplain management
Chesapeake’s flood map shades each property: blue for zone AE, the Special Flood Hazard Area (the 100-year storm), and yellow for the 500-year area.
Helpful resources
A place to
start.
Local support in Chesapeake
Independent public resources. Check with each organization for availability and eligibility.
Questions, answered
A little clarity.
Before we talk.
Do we have to sell the property to work with you?
No. Start with your situation. You may need help planning a move, coordinating a cleanout, or comparing options before deciding whether to sell.
Where is probate handled if the owner lived in Chesapeake?
At the Chesapeake Circuit Court Clerk’s Office, by appointment. With a will, the clerk lists the original will, a certified death certificate or a copy of the obituary, the approximate value of assets the deceased owned alone, and the names and addresses of the heirs. We can help with the house in the meantime. A qualified attorney should advise on probate requirements and who has authority to make decisions. Driven2 Solutions is not a law firm.
Does it matter if the Chesapeake home is in a flood zone?
Chesapeake’s flood map shows each property’s zone, and a home in zone AE could be required to carry flood insurance, which buyers will factor in. If a survey suggests the house sits higher than the map implies, a Letter of Map Amendment from FEMA formally establishes where it stands. Separately, Virginia law requires a seller who knows the home is a repetitive-risk-loss structure, meaning the National Flood Insurance Program has paid two or more claims of more than $1,000 on it within any rolling 10-year period, to disclose that to the buyer (Va. Code § 55.1-708.2).
Will Chesapeake pick up furniture during a cleanout?
Yes, on request, and bulk can go to the curb up to three workdays before your collection day. Branches can be no longer than six feet or thicker than six inches. Renovation debris such as roofing, siding, fencing or pallets is excluded, so plan for that separately. City pickup suits a handful of large items. For a whole house, we can coordinate cleanout, donation and hauling vendors around it.
What if family members have different ideas?
Kristin can explain practical options and help identify questions the family needs to resolve. Ownership, consent, and legal authority should be discussed with a qualified attorney.
Does the home need repairs or a cleanout before we call?
No. Begin with the home in its current condition. We can discuss whether cleanout, repairs, or an as-is option may fit your situation.
Can you help if we live outside Chesapeake?
Yes. We can discuss which tasks need local coordination, who should be involved, and how you prefer to communicate. The scope of support is agreed before work begins.
What will the support cost?
Costs depend on the solution and providers selected. Applicable costs are explained clearly before you decide how to proceed. The initial consultation is free.
Your next step can be a conversation
You don’t need all the answers.
Just a place to start.
Not sure what to do with the property? Start with a conversation. We'll listen to what's happening, understand your goals and help identify the best next step.
- What's happening with the property
- What matters most to you
- Which next steps are worth considering