HMO management in Medway.
Rooms full, costs down. No rent rise needed.
The Renters’ Rights Act, Article 4, and new licensing from January. Medway’s moving fast and most landlords we speak to are worried. Keeping you compliant is the bit we take most seriously. We’re in every HMO we manage every week, so problems get spotted and fixed long before they turn into a fine.
- Better off in 6 months or we work free
- Room empty over 21 days? No tenant find fee
- Live landlord dashboard
- 100% compliant, or next year’s certs are on us
It used to be simpler than this
Find a tenant, sign the tenancy, protect the deposit, get the gas safety done once a year.
That was most of it.
Now Section 21’s gone. Every tenancy rolls on month to month. Fines have gone up to £40,000.
Medway’s brought in Article 4, and from January a lot of the towns need a licence for single lets as well as HMOs.
Every landlord we’ve spoken to this year has asked us the same thing, one way or another.
“Am I actually compliant?”
If you’re managed by us, you don’t have to wonder. You can look.
Five dates every Medway landlord should know
- Jan 2026
Article 4 came in
In seven Medway wards you now need planning permission to turn a family home into an HMO, whatever the size. HMOs already running lawfully aren’t affected.
- 1st May 2026
The Renters’ Rights Act went live
Section 21 ended. Tenancies became periodic. Rent can go up once a year, with two months’ notice. Possession only on the grounds in the Act.
- Late 2026
The landlord database starts
Every landlord will need to register themselves and their properties, with an annual fee. The government’s rolling it out from late 2026.
- 4th Jan 2027
Medway licensing starts
Selective licensing for single lets in seven wards, and additional licensing for smaller HMOs in six. It runs for five years, to 3rd January 2032.
- 2028
The landlord Ombudsman
Membership’s expected to become mandatory, so tenants can take complaints about landlords straight to an independent Ombudsman.
What people say
★★★★★Rated 4.6 out of 5 on Trustpilot. Read all reviewsIf you’re a HMO owner in Kent, use these guys. They are the best managing agent in the County… Since moving to Pineapple, the phone has stopped ringing with problems, and our tenants are happy.
I was looking to speak to a HMO managing agent in Kent and was advised to speak to Pineapple group… Thank you Greg for being generous with your time and for the amazing insights you shared with me about the HMO market in Kent.
I had the opportunity to have a 30 minute call with Greg regarding setting up an HMO in Kent… Our conversation was incredibly helpful and gave me valuable guidance as I continue my HMO journey.
I brought my first property sourced by Pineapple which was great because the property was perfect for what I wanted… Using Pineapple gave me the confidence to invest and I couldn't recommend them enough.
Dealing with Pineapple Living has been a pleasure… The property is excellent and maintained to a high standard. The whole process from application to moving in went very smoothly.
Greg and Stuart has been an invaluable sourcing agent for me in completing a UK property purchase in a short time frame.
I was a tenant with Pineapple for over a year, and it was one of the best properties I’ve stayed in… Any issues that came up in the property were resolved very quickly.
Great people to work with. The team at Pineapple do exactly what they say they are going to do, exactly when they say they are going to do it! How Refreshing!
Very helpful professional advice.
A great agent who truly know the market and simultaneously care about both the landlord’s property and the tenants needs!
I was initially expecting a short call, but Greg went above and beyond giving me advice and pointing out things which I hadn’t considered.
I had a recent telephone meeting with Greg where he gave me excellent advice, helping me navigate the HMO market. His knowledge surrounding all things HMO is incredible.
He went past the call of duty to explain the ins and outs of UK property investment and advise me on a project I was already considering. His help was invaluable in my decision making.
I met with Greg at Pineapple Investment Group who thoroughly guided me through the whole process. The team were fantastic from start to finish.
They were able to guide me through the process with professionalism and quick responses… They even saved me a huge sum of money on sales tax by picking up on something that others missed!
Good sound advice and a clear sensible approach along the whole value chain.
Greg gave me some amazing advice and guidance… I felt listened to and that he understood my individual needs.
10/10 on communication, always someone to talk to if you have questions.
As an overseas buyer, I’ve bought several houses in the UK. One of them is with Pineapple Investment Group. They are definitely the best! They are very responsive and helpful throughout the process.
Their customer service was exceptional—so friendly, responsive, respectful, and understanding.
A trusted partner who helped me manage the renovation project remotely on time and within budget.
From start to finish, Anne, Stuart and Greg were absolutely fantastic. They went above and beyond…
The people are extremely knowledgeable and the resources they offer are the best I’ve seen in the industry.
I was looking to speak to a HMO managing agent in Kent and was advised to speak to Pineapple group… Thank you Greg for being generous with your time and for the amazing insights you shared with me about the HMO market in Kent.
Does Medway’s new licensing cover you?
Tap your ward on the map, or pick it from the list. Not sure which ward you’re in? Put your postcode into the council’s ward finder, or just ask us on the call.
We’ll show you what applies to single lets, to HMOs, and to anyone thinking of converting.
From Medway Council’s approved schemes, starting 4th January 2027. Mandatory HMO licensing for 5 or more people sharing still applies across all of Medway. Ward boundaries: Office for National Statistics, 2024.
The hospital is a big driver of room demand
Medway Hospital in Gillingham is Kent’s largest and busiest hospital, and it’s a big driver of room demand, especially in Gillingham and the parts of Chatham closest to it. There are plenty of people looking for rooms here, but plenty of HMOs too, so your rooms need to stand out from the competition.
Medway Hospital
Medway Maritime Hospital to give it its full name. Over 3,500 staff and 588 beds. Nurses, doctors, students on placement and support staff all want a room they can walk to work from.
Shift workers
Early starts and late finishes. Living within walking distance means not relying on a bus at 6am or after a night shift.
The town centre
Shops, local businesses and Gillingham station, all a short walk from the hospital.
London commuters
Gillingham to London in about 45 minutes on the fastest trains, for a fraction of London rents.
Near the hospital, walking distance is what counts. Within 10 minutes is what most tenants want, and 15 minutes still works. Further out it’s down to the individual, and the town centres work well too. With so many HMOs to choose from, you want a room that stands out.
Medway, town by town
Medway takes in Gillingham, Chatham, Rochester, Strood and Rainham. The same council licensing and Article 4 rules cover all of them, but each one rents differently.
Gillingham
Home to Medway Hospital and a very popular spot for rooms. Walking distance to the hospital is what most tenants want. We’re also seeing more and more people moving out of London and renting rooms here.
Chatham
The town centre, Chatham station and the Universities at Medway campus at Chatham Maritime, shared by Greenwich, Kent and Canterbury Christ Church, with around 10,000 students.
Rochester
Historic town, castle and cathedral. A new £26m station opened in 2015 with direct trains to St Pancras, and around 1,400 new homes at Rochester Riverside are bringing in people moving out of London. Works well for HMOs.
Strood
Mostly residential, but the quickest into London: high speed trains to St Pancras in about 33 minutes. Medway City Estate next door has around 600 businesses and over 6,000 jobs. Near the station is the pick.
Rainham
Quieter and mostly residential, at the eastern end of Medway with its own station. Family homes more than HMOs, but we’d happily manage there.
What rooms are advertised for in Gillingham
A snapshot of rooms to rent on SpareRoom in Gillingham on 17th October 2026. It’s what tenants are comparing your room against this week.
Advertised prices, not achieved rents. En suite rooms are advertised for around £75 a month more. We refresh this every quarter.
Is your room priced for today’s market, or for three years ago?
A quick 20 minute call. We’ll tell you where your rooms sit.Book a callCan’t sleep?
Check your dashboard
It’s 3am and you’ve suddenly remembered the gas safety certificate. Or was it the EICR? Did the new tenant in Room 4 do their Right to Rent check?
Don’t lie there wondering.
When we manage your property, you see what we see. Open your landlord dashboard and every live tenancy, every certificate and every inspection is there.
And it’s not just a green tick. Tap any line and see what was actually done. The certificate itself. The inspection report and the photos. Who did it, and when.
See the proof, not just the promise. Go back to sleep.
Full transparency on every property we manage, on your phone, any time. No emailing us and waiting for someone to dig it out.
Your Chatham HMO
- Gas safety certificateDue 12th Mar 2027✓ In dateAnnual gas safety checkDone 12th March 2026 · Due 12th March 2027Carried out by a Gas Safe engineer
Certificate on file to open and download
Renewal tracked, alert set earlyOpen certificate › - EICRDue 4th Jun 2029✓ In dateElectrical installation condition reportDone 4th June 2024 · Due 4th June 2029Satisfactory result, five year certificate
Any remedial work logged with the invoiceOpen report › - EPCExpires 18th Jan 2032✓ Rating CEnergy performance certificateIssued 18th January 2022 · Expires 18th January 2032Rating and certificate on file
Expiry date trackedOpen certificate › - Fire risk assessmentReview 2nd Sep 2027✓ In dateFire risk assessmentReviewed 2nd September 2026 · Next review 2nd September 2027Written assessment for the building
Every action logged and signed offOpen assessment › - Fire alarm testTested 14th Oct 2026✓ PassedWeekly fire alarm testTested 14th October 2026 · Next due 21st October 2026Alarm and emergency lighting tested
Photo of the signed log book
Every week, every result keptSee the log › - HMO licenceExpires 31st Jan 2029✓ In dateHMO licenceIssued 1st February 2024 · Expires 31st January 2029Licence and conditions on file
Occupancy checked against the licenceOpen licence › - Right to Rent, all tenantsLast check 22nd Aug 2026✓ CheckedRight to RentLast check 22nd August 2026Checked for every adult before move in
Evidence kept on fileSee checks › - Last inspection3rd Oct 2026✓ RecordedQuarterly inspectionDone 3rd October 2026 · Next due January 2027Full report with photos of every room
Communal areas and fire doors checked
Notes, actions and who carried it outOpen report ›
Tap any line to see what was done
Right to Rent
Checked for every adult before they move in, with the evidence kept on file.
Referencing
Identity, income, credit and previous landlord, before anyone gets keys.
Tenancy agreements
Written for the Renters’ Rights Act, signed, and stored against each tenancy.
Deposits
Protected with DPS and the certificate issued to the tenant within 30 days.
Mandatory certificates
Gas safety, EICR, EPC and fire risk assessment, with alerts set well before each one expires.
Weekly fire alarm tests
Done every week in our HMOs and logged. Included in our management, not an extra.
In every HMO, every week
Someone from our team is in every HMO we manage every week, so small problems get spotted and sorted early, before they turn into big ones.
Online maintenance reporting
Tenants report issues through our online system, any time, with photos. Every report is logged and tracked, and issues get resolved quickly.
Quarterly inspections
Every property, every three months, written up with photos. Exactly what Medway’s new HMO licence asks for.
Communal area inspections
Kitchens, hallways, fire doors and escape routes checked and recorded, so small things don’t become enforcement notices.
Licences
Copies on file and expiry alerts set. We can do the application for you, or send you everything you need to do it yourself.
Check in and check out reports
A photo inventory of every room when a tenant moves in and when they leave, so any deposit deduction stands up if it’s disputed.
What changed, and what we do about it
Most of the Act isn’t scary once someone’s handling it properly. The landlords who get caught out are the ones whose agent assumes, or doesn’t tell them.
No more Section 21
Possession now has to be on a legal ground, on a section 8 notice. So the tenant you choose matters more than ever, which is why our referencing comes first.
Periodic tenancies
Every tenancy rolls month to month. Tenants can leave on two months’ notice, so we keep rooms and homes in a state people want to stay in.
Rent reviews once a year
One increase a year, at market rent, with two months’ notice on the right form. We review against what comparable rooms are actually advertised at, so you’re not left behind.
No bidding wars, no big upfront rent
Advertised rent is the rent, and rent in advance is capped at a month. Our adverts and our process work to those rules.
Pets and fair lettings
Pet requests have to be answered within 28 days, and you can’t turn people away for having children or being on benefits. We handle the requests and keep the paper trail.
What’s coming next
The landlord database, the Ombudsman, the Decent Homes Standard. We track the dates and tell you what you need to do before each one lands.
You hear it from us first, not from a letter from the council.
Successful deals
Block of flatsTonbridge RoadMaidstone · off market
6 bed HMOHolland RoadMaidstone · off market
8 bed HMOUpper Fant RoadMaidstone · off market
8 bed HMOCharles StreetMaidstone
7 bed HMOFisher StreetMaidstone
9 bed HMOHayle RoadMaidstone
Existing 11 bed HMOHayle RoadMaidstone
8 bed HMOCollege AvenueGillingham
6 bed HMOBoundary RoadChatham
Block of flatsBerkley RoadGravesend
10 bed HMOBerkley RoadGravesend
Block of flatsParrock StreetGravesend
8 bed HMOHeathfield RoadCroydon · off market
6 bed HMOClive WayCrawley
Block of flatsBower TerraceMaidstone
BeforeAfterBlock of flatsSaltdean Park RoadSaltdean
Block of flatsClaremont GardensSurbitonMore money from your property. Without needing to put the rent up.
Most landlords think the only way to earn more is to put the rent up. It isn't. The money usually leaks out somewhere else.
Empty weeks
A room or a whole house, every week it sits empty is rent you never get back. We aim for 97% occupancy across everything we manage.
Tenants leaving
We match the right tenants to the right home, then we keep them happy. Regular contact, the property kept in good order, and everyone sticking to their tenancy. In shared houses we call it house harmony.
If a tenant hands their notice in, we ask why. Nicely. One told us recently he loved the house but felt people on the road could see into his room. We offered privacy screens. He stayed.
No more guessing
£400 one month, £560 the next, £380 after that. That's what a lot of landlords get from their agent, and it's why property starts to feel like it doesn't pay. With us the swings flatten out, and you see exactly why on your dashboard.
The right tradesperson
Not an electrician for a hob on child lock. Not a bench joiner to hang a shelf. Good people we trust, matched to the job, at cost.
We'd rather wait a week for someone who stays two years than fill it tomorrow with someone who leaves in seven months.
We still check your rent against the market. It's just the last lever we pull, not the first.
We put our fee where our mouth is.
The better off guarantee is for landlords switching from another agent. Every guarantee has simple terms, and we'll go through them on your call.
Your letting agent is a letting agent. We're property investors.
Most agents get paid whether your property performs or not. We know it has to perform, because ours need to too. That changes how we look after every room, every tenant, every repair and every bill.
The hob that wasn't broken
A tenant told us the hob was broken. Plenty of agents would've sent an electrician out, paid the call out and added their margin on top.
We went round, had a look, and it was on child lock. Two seconds to fix. No call out, nothing on the landlord's bill.
That's the stuff we won't tolerate. It's one of the reasons we exist.
Want to know what your property should be doing?
Book a callWe’re landlords here too
We’ve been buying and converting HMOs in Medway since 2018, and we run houses here today. We’re growing in Medway now, which means you’d be one of a small number of landlords we look after here, not one of hundreds. When the rules change, they change for our own houses first.
HMO specialists
Shared houses are the hard end of lettings. It’s where we started, and it’s what most agents would rather not touch.
Your money’s protected
Rent goes through PayProp into a ring fenced client account. We hold Client Money Protection and we’re members of the Property Redress Scheme.
Statements that make sense
Itemised per tenant every month, paid out on the 5th, and an annual statement at your year end if you want one.
No exit fees
No notice period and no penalty for leaving. Nobody should be stuck in a bad deal, and we’d rather you stayed because it works.
“All letting agents are the same.” Not quite.
We were investors first. We spent years learning the trade, finding the properties, negotiating, getting them through legals and planning, and raising the money to buy and refurbish them. Then we handed them to agents who put any old person in, didn’t keep an eye on things, and watched them slowly go downhill.
We got fed up, so we started managing them ourselves. That’s how Pineapple Living started, and it’s why we run every property as if it’s ours. Capped fee, no margin on maintenance, nothing hidden.
Our first job is making your property perform. Tenant experience is a big part of that, because an unhappy tenant moves out and that costs you money. So we’re proactive, firm but fair, and we want to know why anyone’s thinking of leaving.
“Switching sounds like a hassle”
We handle it. We deal with your current agent, collect the keys, contact every tenant and set the property up. It usually takes one to two weeks, and you don’t have to make the awkward call.
“I’m in a notice period”
No problem. We take on the management and you don’t pay twice. We start work from day one and line everything up, so there’s no gap when your old agent’s notice ends.
“My tenants will be unsettled”
We introduce ourselves to every tenant and set up our online maintenance reporting from day one. Tenants who feel looked after stay, and tenants who stay are what makes a property perform.
“What about the deposit?”
It stays protected the whole time. Your current agent transfers it inside the deposit scheme, DPS or TDS, straight across to our agent account, and the tenant gets the updated certificate.
“My agent’s fine, I think”
Ask them for every certificate, the last inspection report and the last fire alarm test, today. If that takes them a week, you’ve got your answer.
“What if you’re no better?”
No exit fees and no notice period. If it stops working, you leave. We’d rather you stayed because it works.
Tell us who your agent is. We’ll do the rest.
- Fill this in. 20 seconds.
- We call you, usually the same day, and check your notice terms.
- We deal with your current agent, the keys, the deposit and every tenant.
No exit fees with us, and no notice period. You’re never stuck.
Four quick questions. We’ll call you, usually the same day, and take it from there.
Start my switchNo obligation. No exit fees with us, ever.
Are you missing a room?
Six rooms each £115 under the market is £690 a month. That’s a whole room’s rent you’re not collecting, over £8,000 a year. Our HMO Health Check finds it.
We inspect every property
Every room and the communal areas, with anything that needs sorting flagged in plain English. Managing it yourself? We’ll go through your certificates, tenancies, deposits and licence too.
Every room checked
Against what’s advertised right now, and against what we’re actually achieving across the rooms we manage. Asking prices only tell half the story.
Upgrades worth doing
Where an en suite, a better layout or an extra room would lift the rent, what it would roughly add each month, and what it would cost to do.
Credited if you switch
£499 covers up to three properties. Sign up for management and the full £499 comes off your fees. The report’s yours to keep either way.
Find out if you’re missing a room.
£499, and it comes off your fees if you switch.See the Health CheckWe handle the switch
A call
30 minutes on your properties, your tenants and what’s keeping you up at night.
A compliance check
We go through what’s on file and tell you straight what’s missing, before anything else.
We take over
We deal with your current agent, collect the keys, and contact every tenant. Usually one to two weeks.
Your dashboard goes live
Every tenancy, certificate and inspection in one place. Have a look whenever you like, 3am included.
Kettle on
The right people are behind your property now. If we need you, we’ll already have the fix. You just give us the green light.
Dreading the awkward call with your current agent? We’ll make it.
Four quick questions, then it’s off your plate. Nothing goes to your agent until you’ve signed. We only take on a few new landlords each quarter.Start my switchCome and see us.
We’ve got two offices, one in Farringdon and one in Maidstone. Pop in, meet the team and see how we run things. Just book a time first so we’re there.
Maidstone
Where it all started. Home base for our HMOs and single lets across Sussex and Kent.
Maidstone, Kent
Farringdon
Our London office, in the heart of Farringdon. Home base for our London single lets.
12-18 Theobalds Road
London WC1X 8PL
Get directions ›
Medway landlords ask us
Do you do HMO management in Medway?
Yes. We’re HMO specialists, and full HMO management is what we do: tenant finding and referencing, compliance, licensing, weekly visits, quarterly inspections, maintenance and rent collection through PayProp. You can see all of it on your landlord dashboard.
How will I end up with more money without putting the rent up?
By stopping the leaks. Fewer empty weeks (we aim for 97% occupancy), tenants who stay because we ask why they’re leaving and fix it, and no call outs that didn’t need to happen. When someone is needed, it’s the right tradesperson at cost, no markup. And if you’re not better off after 6 months, we work for free until you are. We still check rents against the market, but that’s the last thing we touch, not the first.
What are your fees?
12% including VAT, capped at £200 a month per tenancy. In an HMO every room is its own tenancy. No margin on maintenance and no exit fees.
Why do you limit how many new landlords you take on?
Because the service is the whole point. We only grow at a pace where every property still gets the same standard, so we take on a limited number of new landlords each quarter. If we’re full, we’ll tell you straight and hold a space for you next quarter. And if you just want to talk something through, we’ll always make time for a call.
Where’s best for an HMO in Medway?
Within walking distance of Medway Hospital in Gillingham, Kent’s largest hospital and a big driver of room demand, especially in Gillingham and nearby Chatham. Within 10 minutes is ideal and 15 minutes still works. The town centre works well too.
Which parts of Medway do you cover?
All of it. We provide HMO management and lettings across Chatham, Gillingham, Rochester, Strood, Brompton, Luton and the rest of Medway. We already run HMOs here and we’re taking on more landlords now, alongside our houses in Maidstone, Gravesend and Crawley.
Do I need a licence from January 2027?
If you have a single let in Chatham Central and Brompton, Fort Pitt, Gillingham North, Gillingham South, Luton, Strood North and Frindsbury, or Watling, it’s likely to need a selective licence. A smaller HMO in any of those wards apart from Strood North and Frindsbury is likely to need an additional licence. Larger HMOs with 5 or more people already need a mandatory licence anywhere. Tell us the address and we’ll confirm.
How much are the Medway licences?
The council’s approved fees are £840 for a selective licence and £1,600 for an additional HMO licence, with discounts for accredited landlords and some multiple applications. We’ll tell you what applies to you.
Can you apply for the licence for me?
Yes. You can apply and pay yourself and we’ll send you every document you need, or we’ll do the whole thing for you. Applications take real time, especially if a visit’s needed, so we charge a small fee case by case.
Does Article 4 affect my existing HMO?
No. Article 4 applies to new conversions. An HMO that was running lawfully before it came in carries on. If you’re planning a new one in one of the seven wards, you’ll need planning permission first.
What does the Renters’ Rights Act mean for me?
Section 21 ended on 1st May 2026. Every tenancy is now periodic, and you can only regain possession on the grounds in the Act, on a section 8 notice. Rent can go up once a year with two months’ notice. We handle all of it and keep you told.
What is the landlord database?
A national register every landlord will have to join, with details of their properties and an annual fee. The government’s rolling it out from late 2026. We’ll let you know when registration opens and what you need to have ready.
Can I really check my compliance any time?
Yes. Your landlord dashboard shows every live tenancy, the certificates, the inspection records and the documents behind them. If you can’t sleep, have a look.
How often do you inspect?
Someone’s in every HMO we manage every week, for the fire alarm tests and communal area checks, so we catch things early. On top of that there’s a full inspection every three months, written up with photos. That lines up with what Medway’s additional licence will require.
Buying an HMO in Medway instead? See our HMO Deal Check before you make an offer.
Let’s check where you stand
Not ready to switch yet? Tell us what you’ve got and we’ll call you back, usually the same day. 20 minutes, no obligation.
Already decided? Start my switch
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