Dedicated Property Caretaking for Discerning Homeowners

Your Trusted Private Estate Caretaker & Property Management Service

HomeSquare Pro’s Private Estate Caretaker program gives you all the benefits of a dedicated property caretaker — without the payroll, HR headaches, or hiring hassle. Starting at $800/month, experience seamless, personalized estate management from a team you can trust. Request a consultation today.

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45+

Years in Business

5,000

Clients Served
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Professional but approachable handyman services for your home

  • HomeSquare Pro's Private Estate Caretaker program delivers bespoke, full-service property management for homeowners in Fairfield, Westchester, and Putnam Counties — a dedicated caretaker team that knows your property, your preferences, and your standards.

  • Get all the benefits of a private estate caretaker without the cost and complexity of hiring your own employee. Our licensed, insured professionals manage everything from routine maintenance and vendor coordination to 24/7 emergency response.

All-in-One Private Estate Caretaking & Property Management

Our estate caretaker program is fully customized to your property’s unique needs — covering every detail, every season, so you never have to worry about a thing.

Dedicated Personal Caretaker

You’ll be paired with a dedicated caretaker who knows your property inside and out. From routine walkthroughs to special requests, your caretaker is your single point of contact — always responsive, always professional, always discreet.

Customized Property Care Plan

No two estates are the same. We build a fully customized property care plan around your home’s specific needs, your schedule, and your personal preferences — then execute it consistently, month after month.

Vendor Management

Stop coordinating with a dozen different contractors. HomeSquare Pro manages all of your trusted vendors on your behalf — scheduling, overseeing, and quality-checking every job so you don’t have to lift a finger.

Seasonal Home Maintenance

From spring prep to winterization, our team handles all seasonal maintenance tasks to keep your property protected and pristine year-round. We proactively schedule and execute every service so nothing gets missed.

Second Home & Vacation Property Management

Own a second home or vacation property? Our estate caretaker service is the perfect solution for absentee homeowners who want their property maintained, secured, and ready for arrival — without having to manage it from afar.

Process

How It Works

Dedicated caretaker assigned to your property
Customized care plan
Scheduled visits and inspections
Vendor coordination when needed
After-hours phone support
How it works Featured Image
How it works Featured Image

Why Choose us

Why Choose

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All the Benefits, None of the Hassle

Get everything you’d expect from a full-time private caretaker — without the employment costs, payroll taxes, or HR responsibilities. HomeSquare Pro is the smarter, more cost-effective solution for estate property management.

Licensed, Insured & Highly Trained

Every member of our caretaker team is fully licensed, insured, and held to rigorous hiring and training standards. Your estate is managed by true professionals with the expertise to handle anything that comes up.

24/7 Support, Always On

Peace of mind doesn’t have a business-hours schedule. Our team is available around the clock to respond to any issue, emergency, or request — so your property is always in trusted hands, even when you’re not there.

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Your visit, explained step by step

What Happens During A Visit

Full interior and exterior inspection
Power washing
Changing divghtbulbs
Changing filters
Adjusting locks and hardware
Adjusting doors
Touch-up painting
Cleaning grills
Explore Our Full Line of Services

Expert Services Tailored to Your Needs

At HomeSquare Pro, we specialize in four core service areas, ensuring that every project is handled with expertise and care. Whether it's a renovation, electrical work, general handyman tasks, or estate management, our team is equipped to deliver outstanding results. Explore our main service verticals below:

Design & Build

Specialists in renovations, additions, and new construction. Large or small projects, our benchmark is top quality and service.

Handyman & Maintenance

From Gutter Cleaning and Repairs, to Painting and Power Washing, We Have the Team to Help Complete Projects Around Your Home.

Electrical & Generator

Licensed electrical and generator specialists providing safe, code-compliant installations, upgrades, and backup power solutions.

Private Estate Caretaker

Feel Good about Putting the Care and Maintenance of your Property into the Hands of Trusted Professionals.

areas we serve

Area We Serve

Areas We Proudly Serve

Fairfield County Westchester County Putnam County

Testimonials

Check Out What Our Clients Say

Anthony B. did the annual service on our generator. He arrived on time and was very competent and professional in performing the work.

Pierre G

Had power outage and generator didn’t kick in. Called and Anthony came out quickly. Fixed the problem in no time. Anthony is competent and a nice guy.

Ronnie Wippo Meckler

They responded to a semi emergency, prompt and complete. We were very pleased, and they are trustworthy.

Marshall Posner

Service was good, but scheduling could be improved.

Alex R

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