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Start your backyard upgrade with dependable service built for Hudson Valley homes.

Premier Outdoor & Pool Services in Chester, NY, and the Hudson Valley

Professional backyard and pool services in Chester, NY, designed for cold-climate durability. We build, repair, and maintain pools that last through every season.

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Elevate Your Outdoor Living Experience

At The Backyard Bosses, we provide top-tier backyard and pool services in Chester, NY, Orange County, and the Hudson Valley area, including installation, repairs, remodeling, hardscaping, and seasonal pool maintenance. With decades of industry experience and deep local expertise, we build and maintain pools designed to withstand harsh winters and heavy seasonal use.

Chester, NY
(914) 639-4055

Local Builders Who Show Up And Deliver

Name: The Backyard Bosses
Address: Chester, NY, US
Telephone: (914) 639-4055

We started The Backyard Bosses to fill a gap in the Hudson Valley for durable, custom backyard transformations. Our small, hands-on team focuses on quality craftsmanship tailored to local soil, terrain, and weather. From pool openings and closings to full backyard redesigns, we treat every project like it’s our own home.

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Local Expertise: Deep knowledge of Hudson Valley climate, soil conditions, and pool systems.
Certified Professionals: CBP, CPO, CST, and CHTT credentials ensure technical precision.
Full Backyard Solutions: Pools, patios, lighting, and hardscaping handled by one team.
Free Estimates: Clear project planning with no surprises and no initial obligation.
Hands-On Craftsmanship: Personalized builds, never cookie-cutter designs.
Financing Available: We offer flexible financing options through trusted providers.

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Build A Backyard That Lasts

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Create Your Own Backyard Oasis With Us

We provide high-quality pool services in Chester, NY, tailored to established Hudson Valley homeowners. Our work includes custom pool installations, ongoing pool maintenance and seasonal care, pool renovations and upgrades, vinyl liner replacements, equipment and plumbing repairs, and hardscaping services.

We handle:

Pool openings and closings
Seasonal chemical balancing
Cold-climate pool installations
Equipment repair and automation upgrades
Patios, pavers, retaining walls, and pool deck construction

Our process is straightforward. We evaluate your property, design around local conditions, install with precision, and maintain your system for long-term performance.

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Who Best Benefits From Our Work

Our work is best suited for established Hudson Valley homeowners who value long-term quality over quick fixes. If you are investing in your property and want results built for durability, performance, and clean design, you are exactly who we serve.

Homeowners Planning Full Backyard Transformations: If you are ready to invest in high-quality pool construction, renovations, and integrated hardscaping, we build outdoor spaces designed for lasting value and everyday enjoyment.
Existing Pool Owners Needing Repairs or Upgrades: If your pool is aging, leaking, inefficient, or outdated, we provide dependable solutions, including leak detection, resurfacing, equipment replacement, and automation improvements that restore performance and reliability.
Pool Owners Who Want Ongoing Professional Care: If you prefer routine pool care handled correctly the first time, we provide structured maintenance programs, seasonal openings, and closings to keep your system running efficiently year after year.

We build long-term relationships with homeowners who want dependable service they can count on, not temporary fixes.

Upgrade Your Outdoor Living With Confidence

If you need dependable pool services in Chester, NY, and Orange County, we are ready to deliver. Whether you’re installing a new pool, replacing a liner, upgrading equipment, or scheduling seasonal maintenance, our team focuses on reliability and long-term results.

We build backyards that handle Hudson Valley winters, heavy rainfall, and years of family use. From full transformations to routine service, we provide dependable solutions built around your vision.

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Custom Pool And Backyard Solutions

From pool installation to hardscaping and seasonal maintenance, we deliver durable outdoor spaces built for Hudson Valley conditions. Explore each service to see how we transform backyards into lasting investments.

Pool Maintenance

Keep your pool clean, balanced, and ready for every season with reliable maintenance and seasonal services built for Hudson Valley weather.

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Pool Installation

Custom pool builds designed for cold climates with durable materials and precise installation.

Pool Remodeling

Upgrade aging pools with resurfacing, lighting, coping, and structural improvements.

Hardscaping

Patios, retaining walls, and outdoor features that complement your pool and withstand the seasons.

Vinyl Liner

Professional vinyl liner replacement and repair for improved performance and appearance.

Pool Repair

Fast equipment repair and system upgrades to keep your pool running efficiently.

Frequently Asked Questions

We answer common questions about pool installation, maintenance, remodeling, and repairs in Chester, NY. As a trusted pool maintenance company and pool builder, we help homeowners understand timelines, costs, and long-term care.

How often should my pool be professionally maintained?

Most residential pools benefit from weekly or biweekly pool maintenance service, including water testing, filter cleaning, and chemical balancing to prevent costly issues.
Are pools in the Hudson Valley built differently?

Yes. Cold-climate pool installation requires winterization planning, freeze protection, proper drainage, and durable materials designed for seasonal temperature swings.
Do you handle both installation and maintenance?

Yes. We are a full-service pool installer and pool maintenance company, managing construction, remodeling, repairs, and seasonal service.
Can you upgrade older pool equipment?

Absolutely. We provide pool repair service, including pump replacement, heater repair, automation upgrades, and system modernization.
Do you offer Free Estimates?

Yes. We provide Free Estimates for pool services, remodeling, installation, and backyard transformations in Chester, NY, and the surrounding areas.

Trusted By Hudson Valley Homeowners

Kamil Mazurek

Tony was a pleasure to work with, he was quick, professional and excellent in communicating throughout the whole process. I would highly recommend Backyard Bosses to anyone.

Google Reviews

Frank Eisele

I had to have some plumbing work done on my pool, the return lines were leaking. I was worried they might have to break up the pool deck but Tony and his team were able to save the deck repair my return lines. I was out of town when they did the work and when I returned I was both amazed and impressed with the work that was done. Tony communicated regularly with both videos and calls as well as txt’s. I am so happy and can’t wait till Tony and his team replace my liner in the spring. If you need any work done use these guys … you will not be disappointed!

Google Reviews

Bobby Z

FINALLY!!! Tony is amazing! I have been through 3 different pool companies since living here and the service from all of them were horrendous. Thank God The Backyard Bosses started serving the area!! I can’t compliment Tony for his amazing communication, attention to detail and impeccable service enough! It has been such a struggle to find even just a simple season closing and opening service here; that is until Backyard Bosses!! Didn’t just put the cover on and call it a day, they cleaned out my filter, put my furniture away and made sure everything was ready for winter! Top notch service!! Thank you 🙏!!!

Google Reviews

David Rodriguez

So After four years of having our pool closed and having frogs serenade us for the past few summers 😆, it was time to get our pool repaired. We called three pool Companies and Tony from The Backyard Bosses quickly responded to my request. He took a note of everything I wanted and he delivered. It was overwhelming at first but ,Tony broke down the project piece by piece making it manageable and enjoyable watching this transformation take place from beginning to end. Tony was very responsive to every question we had and addressed any issues we had. I highly recommend The Backyard Bosses for your Pool needs and dreams. A man of his word. Hard to find these days.

Google Reviews

Sean Trent

Tony has been fantastic to work with. He is professional, knowledgeable, and made the whole process of getting our new pool heater installed smooth and stress-free. He took the time to explain *everything* and ensured the job was done right. We couldn’t be happier with the service and highly recommend Backyard Bosses!

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Abe Roth

I WILL SAY IT, THE WAY IT IS! A pleasure dealing with Tony, he’s seriously the BEST, he’s taking care of his clients [customers] very well, shows up on time, keeps calm and easy, ALWAYS WITH A SMILE! a pleasure working with him, i can only say good words about him and i strongly recommend others to give him a try… KNOWS WELL HIS WORK & KNOWS HOW TO PLEASE A CLIENT

Google Reviews

Darelle Banks

Backyard Bosses were an absolute pleasure to work with. I needed a new safety cover for the pool and they showed up next day. Communication was great and they did not try to upsell. I feel confident I received only the products I needed and did not over pay. They did such a good job that I am planning to switch to them to open the pool in the spring. Thanks for everything.

Google Reviews

Brad Smith

Built my pool 6 years ago. And have been searching for someone who not only does a great job but is extremely knowledgeable and most important actually cares. Can’t recommend enough.

Google Reviews

Jessica Baum

If you’re looking for the best pool professional in the business, look no further than Tony and The Backyard Bosses. Tony is the definition of integrity: honest, communicative, kind, and incredibly skilled at what he does. After having some truly awful experiences with other local pool services, we were honestly losing faith—until Tony came along. Tony stands by his work, never pushes unnecessary upsells, and clearly cares about building lasting relationships with his clients. He’s reliable, respectful, and a total pro. We feel so lucky to have found him and wouldn’t trust anyone else with our pool. We’ll be working with The Backyard Bosses for many years to come—and you should too!

Google Reviews

Argeny Jimenez

Wow wow wow!! Tony is the absolutely man!!! This guy is the real deal!!! So professional and knowledgeable. I reached out to Tony to open my pool after opening it a bit late since I just had a newborn. And within 3 days I had a crystal clear pool. Can’t say enough about this guy. 10 stars. Doesn’t try and upscale and is a pleasure to work with. I will use no one else but Tony for All my pool services.

Google Reviews

Matt Baecher

Tony is the exact opposite of the pushy contractor looking to upsell services on you and drive up the bill. He’s eager to share his knowledge with you, only do the things you need him to do, and then give you the tools to keep your pool running cleanly on your own. It’s so refreshing to come across someone so genuinely interested in doing right by you. Highly recommended!

Google Reviews

Alexander Compres

I had a great experience with The Backyard Bosses. From start to finish, they were attentive, responsive, and truly cared about delivering a high-quality job. Communication was always prompt, and any questions or concerns I had were addressed right away. Tony showed up on time, worked efficiently, and treated my property with care and respect. It’s clear they take pride in their work and value their customers. Highly recommend them to anyone looking for reliable and professional pool services!

Google Reviews

Certified & Qualified

CBP, CPO, CST, CHTT Credentials

Service Areas

Serving Chester, NY, and Orange County, NY with reliable pool services, installation, remodeling, and hardscaping built for Hudson Valley homes.

Chester, NY
Orange County, NY
Monroe, NY
Washingtonville, NY
Goshen, NY
Warwick, NY
Middletown, NY
Woodbury, NY

Let’s Plan Your Backyard Upgrade

Headquarters

Chester, NY

Phone

(914) 639-4055

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Fill out the form to discuss your pool installation, maintenance, or repair needs. We provide Free Estimates and dependable service built for Hudson Valley conditions.