Windsor, Ontario · Southwestern Ontario · Paralegal Support Available

Windsor Property Management for Landlords

Legal-first systems. Clear documentation. Reliable follow-through. If you own a rental property in Windsor or anywhere in Southwestern Ontario, OLH handles rent collection, tenant communication, maintenance coordination, and owner reporting — with a process designed to reduce stress and protect your file under Ontario's Residential Tenancies Act.

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★★★★★ 4.9 on Google · Trusted by 31,000+ Ontario landlords · Licensed Realtors® & Paralegals

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Screening

Equifax credit · ID · income · LTB history

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Rent Collection

Tracking · arrears follow-up · direct deposit

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Maintenance

Vetted Windsor vendors · work logs

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File Readiness

Docs · evidence · notice-ready records

Why Windsor Landlords Choose OLH

Windsor is our home base — OLH is headquartered at 794 Ouellette Ave, and our team manages properties across Windsor–Essex every day, from student rentals near the University of Windsor to multi-unit buildings downtown. With cross-border demand, a growing hospital and battery-plant workforce, and some of Ontario's strongest rental yields, Windsor landlords need local, legal-first management.

Common Windsor Landlord Problems We Solve

Late rent and constant follow-ups
High-volume tenant messaging and disputes
Maintenance delays and unreliable vendors
Weak documentation and legal risk exposure
Files that escalate to the LTB without warning

What Full Management Includes

Tenant communication, mediation & notice-ready records
Automated rent tracking, arrears follow-up & owner payouts
Work-order intake, vendor scheduling & service history
Equifax rent reporting on every tenancy
Licensed paralegal escalation the moment a file turns legal

Windsor Areas We Cover

Local coverage across Windsor and the surrounding Southwestern Ontario market:

Walkerville South Windsor Riverside East Windsor Sandwich Town Fontainebleau Devonshire Forest Glade

Don't see your exact neighbourhood? We operate province-wide — Ontario property management details →

Nearby: London · Chatham-Kent · Sarnia · Leamington & Kingsville · Brantford · Woodstock

Transparent Monthly Plans

Windsor Property Management Pricing

The same flat monthly rates in Windsor as everywhere in Ontario — no percentage of rent, no hidden fees.

Essential Property Management

$34.99/mo

Automated rent collection & monthly deposits
Online landlord & tenant portals
Tenant message relay (office hours)
DIY legal templates for N4, N1 & reminders

Full Details

Full-Service Property Management

$139/mo

24/7 tenant communication (emergency response available)
Maintenance coordination & contractor management
Emergency & routine repair oversight
On-demand inspections (virtual or in-person)

Full Details

Property Management Legal Guarantee

$199/mo

Everything in Full-Service Property Management
All legal notices, applications & filings managed
Licensed paralegal representation at all LTB hearings
Full case management & enforcement

Full Details

Legal Protection & Rent Guarantees for Windsor Landlords

⚖️ Legal Guarantee — LTB Support When It Matters

All LTB notices prepared, served & filed by licensed paralegals
Representation at every hearing — zero legal fees
Documented arrears & communication logs
Eviction-ready file management from day one

Learn About the Legal Guarantee

💳 Rent Guarantee — Protect Your Cash Flow

Up to 3 months of rent coverage — $1,250/year
Immediate N4 + L1 enforcement on any default
Strong tenant screening requirements
Ideal for higher-value Windsor rentals

View Rent Guarantee Details

Facing a tenant issue right now? Paralegal eviction help · Tenant placement & MLS® leasing · Free landlord self-help centre

Windsor Property Management — Frequently Asked Questions

Do you manage rental properties in Windsor?

Yes — OLH provides full-service property management across Windsor and Southwestern Ontario, including Walkerville, South Windsor, Riverside, East Windsor and surrounding areas. Onboarding and consultations are handled virtually, with local showings and inspections on the ground.

What does property management cost in Windsor?

Flat monthly rates: Essential $34.99/mo, Full-Service $139/mo, or the Legal Guarantee plan at $199/mo with unlimited LTB representation. Multi-unit buildings are priced per unit on a sliding scale. See full pricing.

Can you find tenants for my Windsor rental?

Yes. As a licensed brokerage we list your rental on the MLS® and REALTOR.ca — from a $549 flat fee (DIY) to full-service placement for one month's rent, every package with complete Equifax screening and a legal guarantee. Tenant placement details.

What happens if my tenant stops paying rent?

We serve the N4 immediately, file the L1 at the LTB, and our licensed paralegals handle the hearing and enforcement. Most non-payment cases resolve in roughly 60–90 days depending on LTB scheduling. With the Rent Guarantee, up to 3 months of rent is covered while we enforce.

Do you handle evictions and LTB hearings in Windsor?

Yes — our property managers are licensed paralegals authorized to represent you at the Landlord and Tenant Board, including virtual hearings for Southwestern Ontario matters. Eviction help details.

Do you report rent to Equifax?

Yes — every OLH-managed tenancy includes monthly Equifax rent reporting through LandlordEzy.ca. On-time payers build credit; late payers face real consequences. How rent reporting works.

How do I get started?

Book a free 15-minute strategy call below or call/text (519) 258-3966. Tell us your property type, location, unit count, and tenant situation — we'll recommend the right plan at no cost.

Book a Free 15-Minute Strategy Call — Windsor Landlords

Tell us your property type, location, unit count, and tenant situation. We'll recommend next steps — placement, full management, or legal-first help — at no cost.