Top-rated exterior painters.

Get matched with top exterior painters in Chestertown, NY

Enter your ZIP and get matched with up to 5 pros

Need a pro for your exterior painting project in Chestertown, NY?

Select your specific project to find the pro for you.

Find Exterior painters in Chestertown

Avatar for BUYUKCERCI

BUYUKCERCI

New on AngiNew on Angi
Approved Pro

BUYUKCERCI

New on AngiNew on Angi
Approved Pro

Hi, I m a skilled handyman serving the Albany area. I handle furniture assembly, mounting, minor plumbing & electrical repairs, drywall repair, painting, and general home maintenance. I provide fast, reliable, and professional service with honest pricing. No job is too small — I make your home projects stress-free and done right the first time. Contact me today to get your project started!

Hi, I m a skilled handyman serving the Albany area. I handle furniture assembly, mounting, minor plumbing & electrical repairs, drywall repair, painting, and general home maintenance. I provide fast, reliable, and professional service with honest pricing. No job is too small — I make your home projects stress-free and done right the first time. Contact me today to get your project started!


A Plus Painters of Saratoga

4.43(
7
)
Approved Pro

A Plus Painters of Saratoga

4.43(
7
)
Approved Pro
Customers say: Quick response
37 local quotes requested
20 years of experience

A Plus Painters of Saratoga proudly serves its customers with pride, integrity and attention to the details that matter most to you. This is one of the many things that sets us apart from the rest. We are locally owned and operated. Exterior Painting, Residential and Commercial. Trim, Walls, Deck, Porches, Garages & More! Give us a call today!

"They did a fabulous job, had great ideas that worked well , they were fast, and price was awesome. hard working . Crew was back to check and made sure it was exactly what I wanted.. I highly recommend them. Will definitely use them again.."

Karen P on October 2025

A Plus Painters of Saratoga proudly serves its customers with pride, integrity and attention to the details that matter most to you. This is one of the many things that sets us apart from the rest. We are locally owned and operated. Exterior Painting, Residential and Commercial. Trim, Walls, Deck, Porches, Garages & More! Give us a call today!

"They did a fabulous job, had great ideas that worked well , they were fast, and price was awesome. hard working . Crew was back to check and made sure it was exactly what I wanted.. I highly recommend them. Will definitely use them again.."

Karen P on October 2025


Avatar for Sentri Homes

Sentri Homes

No reviews yet

Sentri Homes

No reviews yet
357 local quotes requested

Sentri Homes is a full-service contractor delivering high-end home additions, whole-home remodels, new custom builds, luxury kitchens, structural framing, roof replacements, and every major renovation. We assign a dedicated project manager to every job, deliver meticulous craftsmanship with clear communication, and back our work with an industry-leading warranty to ensure complete peace of mind on your largest investments. Our in-house team of licensed builders and master craftsmen consistently earns 5-star reviews by turning big visions into stunning, high-value homes—when you need one trusted partner who truly does it all, we’re the proven choice.

Sentri Homes is a full-service contractor delivering high-end home additions, whole-home remodels, new custom builds, luxury kitchens, structural framing, roof replacements, and every major renovation. We assign a dedicated project manager to every job, deliver meticulous craftsmanship with clear communication, and back our work with an industry-leading warranty to ensure complete peace of mind on your largest investments. Our in-house team of licensed builders and master craftsmen consistently earns 5-star reviews by turning big visions into stunning, high-value homes—when you need one trusted partner who truly does it all, we’re the proven choice.


Avatar for Armstrong & Sons Enterprises

Armstrong & Sons Enterprises

No reviews yet

Armstrong & Sons Enterprises

No reviews yet
33 years of experience

Exterior Painting - all Line striping commercial/ industrial Parking lot/asphalt cleaning Sports courts / basketball pickleball Professional and maticulant Great follow up and satisfaction guaranteed

Exterior Painting - all Line striping commercial/ industrial Parking lot/asphalt cleaning Sports courts / basketball pickleball Professional and maticulant Great follow up and satisfaction guaranteed


Avatar for Apex Pro Siding and Repair

Apex Pro Siding and Repair

5.00(
7
)

Apex Pro Siding and Repair

5.00(
7
)
Customers say: Quick response
Recommended by 100% of Angi customers
Recommended by 100% of HomeAdvisor customers

Apex Pro Siding and Repair is a locally owned and operated business specializing in siding and chimney repair. We believe our success relies entirely on your satisfaction. Our highly skilled and experienced professionals are dedicated to getting the job done right at a fair price. Whether you need siding installation, replacement, or chimney repair, we use the best resources and materials available while applying years of hands-on experience to every residential or commercial project. Trust Apex Pro Siding and Repair for quality service in the Capital Region of New York. Your satisfaction is our priority, ensuring your home or business is protected and looking its best.

"Very timely, responsive, reasonable and good results. Don’t look elsewhere. Found Sergie by chance online. I passed his info off to a bunch of friends. A great find. Don’t overpay elsewhere."

Greg T on October 2024

Apex Pro Siding and Repair is a locally owned and operated business specializing in siding and chimney repair. We believe our success relies entirely on your satisfaction. Our highly skilled and experienced professionals are dedicated to getting the job done right at a fair price. Whether you need siding installation, replacement, or chimney repair, we use the best resources and materials available while applying years of hands-on experience to every residential or commercial project. Trust Apex Pro Siding and Repair for quality service in the Capital Region of New York. Your satisfaction is our priority, ensuring your home or business is protected and looking its best.

"Very timely, responsive, reasonable and good results. Don’t look elsewhere. Found Sergie by chance online. I passed his info off to a bunch of friends. A great find. Don’t overpay elsewhere."

Greg T on October 2024


Avatar for Papa dukes

Papa dukes

No reviews yet

Papa dukes

No reviews yet

We are a family owned and operated buisness. We prioritize in garunteeing ur satisfaction while also making sure were both happy at the end of the job , primarily we focus on tree work ,masonry, hardscaping , landscaping, painting , dump runs and cleanouts and anything in between . We lookforward to hearing from you

We are a family owned and operated buisness. We prioritize in garunteeing ur satisfaction while also making sure were both happy at the end of the job , primarily we focus on tree work ,masonry, hardscaping , landscaping, painting , dump runs and cleanouts and anything in between . We lookforward to hearing from you





First choice painting and renovations

2.00(
1
)

First choice painting and renovations

2.00(
1
)
Customers say: Terrific value

I am an interior and exterior painter. I specialize in repairing sheetrock and painting, making sure everything is perfect. In addition to that, always tailoring to my customers specific needs. I take the proper steps in setting up, making sure everything in your home is protected. I will always make sure all measures are taken to do a professional job. I make sure that the customer is happy with the entire job, every time. I have been a professional painter for 15 years. I have always worked for a large company, but started my own business last year. Go with First Choice Painting and Renovations, because First Choice is the right choice!

"Job left incomplete, preparation steps were skipped resulting in poor results. In error, Mr. Williams was paid in full and has never returned. Communication was full of excuses and false promises of follow up, which resulted in no show appointments. Now refuses to respond to any form of communication. Job still incomplete, we are pursuing small claims court as a result."

Michael M on May 2021

I am an interior and exterior painter. I specialize in repairing sheetrock and painting, making sure everything is perfect. In addition to that, always tailoring to my customers specific needs. I take the proper steps in setting up, making sure everything in your home is protected. I will always make sure all measures are taken to do a professional job. I make sure that the customer is happy with the entire job, every time. I have been a professional painter for 15 years. I have always worked for a large company, but started my own business last year. Go with First Choice Painting and Renovations, because First Choice is the right choice!

"Job left incomplete, preparation steps were skipped resulting in poor results. In error, Mr. Williams was paid in full and has never returned. Communication was full of excuses and false promises of follow up, which resulted in no show appointments. Now refuses to respond to any form of communication. Job still incomplete, we are pursuing small claims court as a result."

Michael M on May 2021

...
Showing 1-10 of 91
Exterior Painting questions, answered by experts

There is no one correct order for painting a room, as it largely depends on personal preference and skill level. However, for non-professional painters, we recommend the following order: ceiling, walls, doors, windows, trim. This is because painting trim, windows, and doors can be more time-consuming and meticulous, and it's best to save them for last when you’ve already gained some confidence from painting the larger surfaces.

Once you prep a house for exterior painting, painting with a sprayer can go quickly. Spray painting results in a thin layer of paint, likely taking multiple layers to get full coverage. You can expect the spray paint job to take at least one day, including dry time, but it can take longer depending on how large of a home it is and the weather conditions.

You can paint over water-damaged drywall as long as it’s dry and there’s no active leak. However, painting over the area will not solve deeper problems like mold or water leaks. 

If you’re 100% positive that these two issues aren’t a concern, paint over the area with a water—or oil-based primer. This type of paint will ensure that it doesn’t simply seep into the spot.

When applying the first coat of touch-up paint, it is best to use a paint roller. A roller allows you to get a thin layer of paint to the area to avoid an unsightly blend with the old coat of paint. However, if you need to touch up the area a second time after the first coat has dried, a small brush will work best to avoid applying too much paint.

You’ll want to use a sprayer to paint your garage door, especially if the door has panels and other details. A sprayer can get those hard-to-reach places much easier than cutting in with a brush or trying to roll the paint. Once you get comfortable using a sprayer, you’re more likely to get a smooth, professional-looking finish. However, a paint roller will also work if you’ve got a flat garage door or if you don’t have access to a sprayer.

The Chestertown, NY homeowners’ guide to exterior painting services

From average costs to expert advice, get all the answers you need to get your job done.

What do you need done? We’ll find top pros.
  • 🌱 "Mow a small front yard"
  • 🛠 "Fix a leaking pipe under the sink"
  • 🏠 "Repair shingles on an asphalt roof"