Pricing

Every price, in plain sight.

Two products, two audiences. Property owners and managers run the suite; contractors and their crews run SquareKeeper Works. A 30-day trial, no credit card, and no quote gate — the number on this page is the number you pay.

Property owners & managers Service providers

30-day trial No credit card No setup fee Cancel anytime
For property owners & managers

The SquareKeeper suite

Seven modules for running a commercial property. Take the bundle or pick only what you need.

Most popular

SquareKeeper Complete

$499 / month $429 / month

Save $1,128 a year vs. the seven modules à la carte Save $1,968 a year vs. paying for all seven modules monthly

All seven separately run $593/mo — bundled down to $499. Tenant and vendor logins are always free. $429/mo billed annually — $5,148 for the year. Tenant and vendor logins are always free.

  • Parking Manager
  • Maintenance Manager
  • Employee Manager
  • Operations Manager
  • Security Manager
  • Tenant Portal
  • Vendor Portal
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À la carte

Or pick only the modules you need.

Add or remove modules anytime. Annual billing saves 10% on every standalone module.

A property manager presenting to her team in a conference room
Operations Manager

Cross-module orchestration · Google Calendar sync · daily wrap · compliance tracker

$109/mo $98/mo billed monthly $1,177 billed once a year
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Maintenance Manager

Work orders · subtasks · before/after photos · bilingual QR restroom reports

$99/mo $89/mo billed monthly $1,069 billed once a year
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Employee Manager

GPS-verified time clock · activity tracking · timesheets · payroll exports

$49/mo $44/mo billed monthly $529 billed once a year
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Tenant Portal

Tenant self-service: vehicle registration · maintenance requests · announcements

$99/mo $89/mo billed monthly $1,069 billed once a year
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Vendor Portal

Vendor check-in · work-order acceptance · invoice submission · on-site geofence

$79/mo $71/mo billed monthly $853 billed once a year
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Parking Manager

License plate enforcement · vehicle registry · tenant tracking · violation workflow

$99/mo $89/mo billed monthly $1,069 billed once a year
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Security Manager

Incident reports · QR patrols · guard licensing · audit-ready exports

$59/mo $53/mo billed monthly $637 billed once a year
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Included with every plan
Checklists

The built-in to-do app for your whole team — My Day, reminders, and one tap that turns a to-do into a tracked work order or project. Web & native Android. Comes with any module you pick; not sold separately.

Included No extra charge
See Checklists
Add-ons

No annual discount — add-ons cost the same on monthly and annual billing.

Tenant text messaging

Announcements by text to tenants who opt in · up to 2,000 texts a month, then it keeps going by email · requires the Tenant Portal. Add it from your billing settings once you're on a paid Tenant Portal plan.

$49/mo $49/mo
Office Assistant Plus

Your AI office assistant across every module — 1,500 messages and 15 AI file builds a month, with the AI File Builder in Operations Manager included · every plan already includes the assistant free at 15 messages a day · requires Operations Manager. Add it from your billing settings.

$69/mo $69/mo
Office Assistant Max

The high-volume Office Assistant tier — 6,000 messages and 60 AI file builds a month (four times Plus) · requires Operations Manager. Add it from your billing settings.

$150/mo $150/mo

Busy month? One-time packs from your billing settings: +500 messages for $10, +20 AI file builds for $10. A pack balance is used after your monthly allowance and stays available while you keep an Office Assistant plan.

How Office Assistant messages are counted

A message you send is one message. Tapping one of the assistant's buttons counts the same as typing. Its greeting is free, confirming or cancelling something it prepared is free, and a message that fails never counts. The assistant shows your running count as you approach the limit.

AI file builds are counted separately — the AI File Builder in Operations Manager is included in both tiers, so you will see "3 of 15 builds" rather than any conversion between the two.

Every SquareKeeper plan includes the assistant for 15 messages a day at no charge. These tiers raise that ceiling; nothing about what the assistant can do changes.

Switch to annual billing anytime and save 10% on every standalone module. Annual prices shown as the monthly equivalent, billed once a year.

Cost comparison

What the same capability costs elsewhere.

Here's what it would cost to get the same capability from other companies. Typical small commercial property (30 tenants, 5 staff). All competitor numbers reflect what you'd actually pay, including setup fees amortized over year 1. Competitor prices verified May 2026.

Function What you'd use Monthly Logins
Parking enforcement ParkingPass + revenue share $100 – $300 1
Work orders / CMMS MaintainX Premium (5 users) $245 – $295 1
Employee time / GPS Homebase Plus (1 location) $60 1
Security / incident Silvertrac (10 devices) $349 1
Tenant portal Buildium Essential $62 1
Vendor portal TrustLayer + email $50 1
Operations coordination Asana (5 users) $55 1
All 7 tools combined 7 separate companies, 7 separate bills, none of them share info $921 – $1,171/mo 7
SquareKeeper Complete One company. One bill. Unlimited free logins for tenants & vendors. $499/mo 1

Most commercial property managers don't currently buy all of these tools separately — they absorb the gaps as labor cost or skipped work. SquareKeeper covers the gaps that paper, spreadsheets, and group texts are currently filling. Even properties already running MaintainX or Homebase typically lack parking enforcement, tenant and vendor portals, security incident tracking, and operations coordination. This comparison shows what equivalent capability actually costs.

For service providers

SquareKeeper Works

For contractors and their crews — turn jobsite photos into branded reports that win the next job. Your whole crew is included on every plan; you never pay per person.

Use Works completely on its own — you never need another SquareKeeper module. And when a client runs their property on SquareKeeper, every report you send files right into their records, automatically. Great on its own, better together.

A contractor in a hard hat documenting a job on a commercial rooftop
Free
$0/mo
  • 5 reports per month
  • Up to 5 crew members
  • 100 photos per month
  • English & Spanish
  • Your whole crew included, no per-person charge
  • Photos from the whole crew, even with no signal
  • Branded PDF reports
  • Live client link that stays active with your account
  • AI-drafted report narrative
  • Office Assistant — AI helper, 15 messages a day
  • Sync reports to a SquareKeeper client
  • Referral rewards
  • Higher report and photo caps
  • Quotes clients accept online
  • Invoices + QuickBooks push
  • Invoice payment terms
  • Recurring service plans & scheduling
  • Time cards
Start free
Pro
$79/mo
  • 100 reports per month
  • Up to 50 crew members
  • 5,000 photos per month
  • English & Spanish
  • Your whole crew included, no per-person charge
  • Photos from the whole crew, even with no signal
  • Branded PDF reports
  • Live client link that stays active with your account
  • AI-drafted report narrative
  • Office Assistant — AI helper, 15 messages a day
  • Sync reports to a SquareKeeper client
  • Referral rewards
  • Higher report and photo caps
  • Quotes clients accept online
  • Invoices + QuickBooks push
  • Invoice payment terms
  • Recurring service plans & scheduling
  • Time cards
Choose Pro
Coming soon
Business
$129/mo
  • 500 reports per month
  • Up to 250 crew members
  • 25,000 photos per month
  • English & Spanish
  • Your whole crew included, no per-person charge
  • Photos from the whole crew, even with no signal
  • Branded PDF reports
  • Live client link that stays active with your account
  • AI-drafted report narrative
  • Office Assistant — AI helper, 15 messages a day
  • Sync reports to a SquareKeeper client
  • Referral rewards
  • Higher report and photo caps
  • Quotes clients accept online
  • Invoices + QuickBooks pushSoon
  • Invoice payment termsSoon
  • Recurring service plans & schedulingSoon
  • Time cardsSoon
Not available yet
Add-ons

Every plan includes the Office Assistant free at 15 messages a day — these upgrades raise that ceiling. Added from your settings in the app on any paid plan.

Office Assistant Plus

Your AI assistant in Works — 1,500 messages a month. Requires a paid plan; add it from your settings in the app.

$69/mo $69/mo
Office Assistant Max

The high-volume tier — 6,000 messages a month (four times Plus). Requires a paid plan; add it from your settings in the app.

$150/mo $150/mo

Busy month? A one-time pack from your settings in the app: +500 messages for $10. A pack balance is used after your monthly allowance and stays available while you keep an Office Assistant plan.

Works is billed month to month and priced the same either way — the annual toggle above applies to the suite, not to Works. See the full SquareKeeper Works page →

Try SquareKeeper free for 30 days.

No credit card, no setup fee, no call with a salesperson.

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After your 30 days there's a short grace period before anything locks — and we never auto-charge a card you didn't give us.