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Find Deck staining or painters in Winchester

Avatar for Crystal General Contracting

Crystal General Contracting

123 Lynn Fells Pkwy
4.91(
100
)
Approved Pro

Crystal General Contracting

123 Lynn Fells Pkwy
4.91(
100
)
Approved Pro
Customers say: Quality work
Recommended by 97% of Angi customers
Recommended by 97% of HomeAdvisor customers
163 local quotes requested

**SPRING IS HERE AND WE'RE EXCITED TO CONNECT WITH YOU ABOUT YOUR EXTERIOR PAINTING PROJECT!!**We have been serving clients since 2008 with a full range of high-quality exterior and interior painting services with our team of highly trained and dedicated house painters. Our goal is to deliver top-notch quality and a unique customer service experience in business and home owners. Crystal Painting will offer you a free, personalized quote tailored to the individual needs of your project. We provide a broad range of commercial and residential painting services as well as plastering, carpentry, and wallpaper removal.

"Crystal Painting crew was professional, polite and efficient. They took great care in preparing and painting out home. Did great job, reliable! We are very pleased with the job they did. Highly recommend!"

Gail M on October 2025

**SPRING IS HERE AND WE'RE EXCITED TO CONNECT WITH YOU ABOUT YOUR EXTERIOR PAINTING PROJECT!!**We have been serving clients since 2008 with a full range of high-quality exterior and interior painting services with our team of highly trained and dedicated house painters. Our goal is to deliver top-notch quality and a unique customer service experience in business and home owners. Crystal Painting will offer you a free, personalized quote tailored to the individual needs of your project. We provide a broad range of commercial and residential painting services as well as plastering, carpentry, and wallpaper removal.

"Crystal Painting crew was professional, polite and efficient. They took great care in preparing and painting out home. Did great job, reliable! We are very pleased with the job they did. Highly recommend!"

Gail M on October 2025


JK Painting Service Corp.

12 Tudor St
5.00(
16
)
Approved Pro

JK Painting Service Corp.

12 Tudor St
5.00(
16
)
Approved Pro
Customers say: Quick response
93 local quotes requested
14 years of experience

JK Painting is a residential contracting company providing quality home painting in Waltham, MA and surrounding areas. We would love to help make your home painting project a reality. Our knowledge, professionalism and experience allow us to meet our clients needs on every project. We pride ourselves on the quality of our workmanship and our prompt professionalism -- our customers come back to us time and time again! We provide unparalleled service.

"JK Painting was prompt, timely, and professional. Well done repair, and painting."

hamilton G on August 2020

JK Painting is a residential contracting company providing quality home painting in Waltham, MA and surrounding areas. We would love to help make your home painting project a reality. Our knowledge, professionalism and experience allow us to meet our clients needs on every project. We pride ourselves on the quality of our workmanship and our prompt professionalism -- our customers come back to us time and time again! We provide unparalleled service.

"JK Painting was prompt, timely, and professional. Well done repair, and painting."

hamilton G on August 2020


Avatar for Suetam Painting and Finishes

Suetam Painting and Finishes

54 May Street
5.00(
7
)
Approved Pro

Suetam Painting and Finishes

54 May Street
5.00(
7
)
Approved Pro
Customers say: Quick response
Recommended by 100% of Angi customers
Recommended by 100% of HomeAdvisor customers
964 local quotes requested

“With nearly 100 five-star Google reviews, we’ve been proudly serving homeowners since 2018. Specializing in premium interior painting and cabinet refinishing, we deliver exceptional quality and craftsmanship you can trust.”

"Fabulous! The entire job was done in 1 day. I would recommend Suetam very highly."

Dan C on January 2025

“With nearly 100 five-star Google reviews, we’ve been proudly serving homeowners since 2018. Specializing in premium interior painting and cabinet refinishing, we deliver exceptional quality and craftsmanship you can trust.”

"Fabulous! The entire job was done in 1 day. I would recommend Suetam very highly."

Dan C on January 2025


Avatar for Affordable Painting

Affordable Painting

15 Passaconaway Dr
4.46(
78
)
Approved Pro

Affordable Painting

15 Passaconaway Dr
4.46(
78
)
Approved Pro
Customers say: Terrific value
172 local quotes requested
26 years of experience

Affordable Painting has over 40 years of experience painting and servicing Massachusetts and New Hampshire. e service many of the towns & cities located in the Greater Boston and Central New Hampshire area.

"Mark did an exceptional job on our interior project. He is a hard worker, is there when he said he would be there, very professional, and reasonably priced. We would absolutely hire him again."

Robert D on March 2024

Affordable Painting has over 40 years of experience painting and servicing Massachusetts and New Hampshire. e service many of the towns & cities located in the Greater Boston and Central New Hampshire area.

"Mark did an exceptional job on our interior project. He is a hard worker, is there when he said he would be there, very professional, and reasonably priced. We would absolutely hire him again."

Robert D on March 2024


Lighthouse Painting

300 BRICKSTONE SQ
4.79(
14
)
Approved Pro

Lighthouse Painting

300 BRICKSTONE SQ
4.79(
14
)
Approved Pro
Customers say: Quick response
Recommended by 92% of Angi customers
Recommended by 92% of HomeAdvisor customers
1300 local quotes requested

With over 40+ years of combined experience throughout our team, Lighthouse Painting is ready to paint your vision! With over 1500+ completed projects, we strive towards providing unparalleled customer service - and it starts with communication. Our staff is prompt, courteous, and are ready to provide you with quality results on your painting project every step of the way. Call or message us today to schedule your complimentary estimate!

"Very professional. job completed per contract specifications. Workers completed tasks with a pleasant “can do”attitude. Maintained a clean work area during the work. Would hire again"

Paul G on June 2025

With over 40+ years of combined experience throughout our team, Lighthouse Painting is ready to paint your vision! With over 1500+ completed projects, we strive towards providing unparalleled customer service - and it starts with communication. Our staff is prompt, courteous, and are ready to provide you with quality results on your painting project every step of the way. Call or message us today to schedule your complimentary estimate!

"Very professional. job completed per contract specifications. Workers completed tasks with a pleasant “can do”attitude. Maintained a clean work area during the work. Would hire again"

Paul G on June 2025


Avatar for Chilins Painting & Remodeling

Chilins Painting & Remodeling

604 Bay Dr
4.85(
27
)
Approved Pro

Chilins Painting & Remodeling

604 Bay Dr
4.85(
27
)
Approved Pro
Customers say: Quality work
Recommended by 96% of Angi customers
Recommended by 96% of HomeAdvisor customers
701 local quotes requested

Family run business who are ready to start helping owners create the home they have always wanted! We have over 25 years of experience! We get our jobs done as quickly and as efficiently as possible at a reasonable price! Perfection is what we strive for at all times! Our clients satisfaction is what keeps us going throughout our profession. We use the best of the best painting materials along with the best painting brand " Benjamin Moore". Our company is based out of Northborough & Marlborough Massachusetts but we service all of Massachusetts.

"Chillins Painting & Remodeling – A Total Disaster of a Company If I could give zero stars, I would. Hiring Chillins Painting & Remodeling was an absolute nightmare from start to finish. This company has no business calling themselves professionals. The paint job they rushed through started peeling within days — not months, not weeks, days. Their siding work was just as bad: they dumped the old siding all over our lawn, killed most of our grass, and then acted like it wasn’t their responsibility. We had to beg them to come back just to clean up their own mess. When it came time to actually finish the job, they offered one ridiculous excuse after another — locked keys, injuries, “other jobs” they chose to prioritize instead of ours. Finally, when the owner begrudgingly returned, he tried to shake us down for more money before doing the work we already paid for. That second attempt was just as careless and pathetic as the first, with peeling paint, visible damage to our siding, and yet another pile of unused materials they dumped on our property for us to pay to remove. Chillins Painting & Remodeling is everything you hope to avoid when hiring a contractor: sloppy, dishonest, condescending, and utterly incompetent. They cut corners at every step, treat their customers with disdain, and leave your property in worse condition than when they started. This company is a scam dressed up as a contractor. If you care about your home, your money, or your sanity, stay far, far away from Chillins Painting & Remodeling. They are a complete embarrassment to their trade."

Robert M on October 2025

Family run business who are ready to start helping owners create the home they have always wanted! We have over 25 years of experience! We get our jobs done as quickly and as efficiently as possible at a reasonable price! Perfection is what we strive for at all times! Our clients satisfaction is what keeps us going throughout our profession. We use the best of the best painting materials along with the best painting brand " Benjamin Moore". Our company is based out of Northborough & Marlborough Massachusetts but we service all of Massachusetts.

"Chillins Painting & Remodeling – A Total Disaster of a Company If I could give zero stars, I would. Hiring Chillins Painting & Remodeling was an absolute nightmare from start to finish. This company has no business calling themselves professionals. The paint job they rushed through started peeling within days — not months, not weeks, days. Their siding work was just as bad: they dumped the old siding all over our lawn, killed most of our grass, and then acted like it wasn’t their responsibility. We had to beg them to come back just to clean up their own mess. When it came time to actually finish the job, they offered one ridiculous excuse after another — locked keys, injuries, “other jobs” they chose to prioritize instead of ours. Finally, when the owner begrudgingly returned, he tried to shake us down for more money before doing the work we already paid for. That second attempt was just as careless and pathetic as the first, with peeling paint, visible damage to our siding, and yet another pile of unused materials they dumped on our property for us to pay to remove. Chillins Painting & Remodeling is everything you hope to avoid when hiring a contractor: sloppy, dishonest, condescending, and utterly incompetent. They cut corners at every step, treat their customers with disdain, and leave your property in worse condition than when they started. This company is a scam dressed up as a contractor. If you care about your home, your money, or your sanity, stay far, far away from Chillins Painting & Remodeling. They are a complete embarrassment to their trade."

Robert M on October 2025


Avatar for North Shore Painting

North Shore Painting

PO Box 663
4.86(
57
)
Approved Pro

North Shore Painting

PO Box 663
4.86(
57
)
Approved Pro
Customers say: True professional
Recommended by 94% of Angi customers
Recommended by 94% of HomeAdvisor customers
1086 local quotes requested

When you need the best painting the area has to offer, turn to us and our 25+ years of experience, as well as our high retention rate with many satisfied customers. Whether you want to build your dream home or you need home improvements, we've got you covered!

"My crew from NSP was amazing. Professional, courteous, kind and on point to get the task done. Large 2 story colonial with addition and ovs garage. I believe it took total of 5 days because of early weather in October 22. No paint chips on ground, very conscious of my shrubs and gardens, you would not even know they were painting. I HIGHLY RECOMMEND this outstanding company and would not hesitate to have them paint my home again. The price was very fair, the warranty good but most of all they always stayed in touch to let me know what was going to happen etc. My team, Frank, Benjamin and Valerio were amazing. Peter the owner and coordinator did a great job. Thank you again. My neighbors stopped to tell me how great my home looks and asked for the name of the painters for them in springtime. Thats says much about Northshore Painting. Great job, great professionalism, great job. VCM Billerica Ma"

Virginia c M on December 2022

When you need the best painting the area has to offer, turn to us and our 25+ years of experience, as well as our high retention rate with many satisfied customers. Whether you want to build your dream home or you need home improvements, we've got you covered!

"My crew from NSP was amazing. Professional, courteous, kind and on point to get the task done. Large 2 story colonial with addition and ovs garage. I believe it took total of 5 days because of early weather in October 22. No paint chips on ground, very conscious of my shrubs and gardens, you would not even know they were painting. I HIGHLY RECOMMEND this outstanding company and would not hesitate to have them paint my home again. The price was very fair, the warranty good but most of all they always stayed in touch to let me know what was going to happen etc. My team, Frank, Benjamin and Valerio were amazing. Peter the owner and coordinator did a great job. Thank you again. My neighbors stopped to tell me how great my home looks and asked for the name of the painters for them in springtime. Thats says much about Northshore Painting. Great job, great professionalism, great job. VCM Billerica Ma"

Virginia c M on December 2022


Avatar for Northeast Maintenance Services

Northeast Maintenance Services

4 Sherwood Dr
4.77(
182
)
Approved Pro

Northeast Maintenance Services

4 Sherwood Dr
4.77(
182
)
Approved Pro
Customers say: Quality work
Recommended by 94% of Angi customers
Recommended by 94% of HomeAdvisor customers
986 local quotes requested

Owner operated. 7 years ANGI Super Service Award Winner! We cater to Commercial and Residential Services. Call us for all your needs of interior & Exterior painting, Pressure Washing your Home and Miscellaneous fixtures. We provide Gutter Repair and Installation, Deck Maintenance & Refinishing, Chimney Repointing & Maintenance, Water & Mold Remediation, and Carper Cleaning. We'd prefer you please call or email for more information.

"Terrible. Chris did minimal work. Refused to return to the property. Ignored repeated phone calls. After 2 years he filed a small claims for the "work" After no proper invoicing or follow up. 0/10. Do not recommend. Legal headaches are worse than poorly cleaned gutters."

DB H on January 2025

Owner operated. 7 years ANGI Super Service Award Winner! We cater to Commercial and Residential Services. Call us for all your needs of interior & Exterior painting, Pressure Washing your Home and Miscellaneous fixtures. We provide Gutter Repair and Installation, Deck Maintenance & Refinishing, Chimney Repointing & Maintenance, Water & Mold Remediation, and Carper Cleaning. We'd prefer you please call or email for more information.

"Terrible. Chris did minimal work. Refused to return to the property. Ignored repeated phone calls. After 2 years he filed a small claims for the "work" After no proper invoicing or follow up. 0/10. Do not recommend. Legal headaches are worse than poorly cleaned gutters."

DB H on January 2025


Avatar for Target Painting & Contracting Inc

Target Painting & Contracting Inc

708 Boston Post Rd
4.89(
85
)
Approved Pro

Target Painting & Contracting Inc

708 Boston Post Rd
4.89(
85
)
Approved Pro
Customers say: True professional
Recommended by 95% of Angi customers
Recommended by 95% of HomeAdvisor customers
928 local quotes requested

With over 200 years of combined experience, we have the skills to deliver a quality home renovation for your needs. We do expert work and use only premium products from manufacturers such as Sherwin Williams, Benjamin Moore, California, and Cabot. Don't let just anyone perform your renovations. Our team of professionals is fully insured for your protection. Certificates of insurance are provided to clients and potential clients, upon request.

"Go with Target. I've used several painters, and I have never had the excellent level of quoting and detailed Statement of Work, customer service responsiveness, crew professionalism, quality of prep work and painting, and ability to deliver on my timeline. I am not easily impressed, but Andy, Gabriella, and team knocked it over the Green Monster!"

Rob H on June 2023

With over 200 years of combined experience, we have the skills to deliver a quality home renovation for your needs. We do expert work and use only premium products from manufacturers such as Sherwin Williams, Benjamin Moore, California, and Cabot. Don't let just anyone perform your renovations. Our team of professionals is fully insured for your protection. Certificates of insurance are provided to clients and potential clients, upon request.

"Go with Target. I've used several painters, and I have never had the excellent level of quoting and detailed Statement of Work, customer service responsiveness, crew professionalism, quality of prep work and painting, and ability to deliver on my timeline. I am not easily impressed, but Andy, Gabriella, and team knocked it over the Green Monster!"

Rob H on June 2023


Avatar for Vallen Pro Painters

Vallen Pro Painters

60 Elvino Florry Drive
5.00(
2
)
Approved Pro

Vallen Pro Painters

60 Elvino Florry Drive
5.00(
2
)
Approved Pro
Customers say: Quick response
Recommended by 100% of Angi customers
Recommended by 100% of HomeAdvisor customers
926 local quotes requested

Vallen Pro Painters brings high quality, timely delivery, and competitive rates to its clients. Having many years of experience, Vallen Pro Painters ensures high quality service using the best equipment in the market, premium products, materials and trained staff. Customers satisfaction is our top priority- and Vallen Pro Painters is sure to deliver."

"Diego and his crew did an absolutely fabulous job. He checked in regularly with us before starting the job, painted sample colors on our shingles for us to see them in place and power washed the house before starting painting. They took meticulous care, caulking, sanding weathered shingles and repairing a rotted window sill. The price was very reasonable. Diego is outstandingly gracious and personable. We couldn't be happier with the job. We've worked with many contractors over the years we've had our old house, and this was the most favorable experience yet. We highly highly recommend Vallen Pro Painters!"

Tavia M on June 2022

Vallen Pro Painters brings high quality, timely delivery, and competitive rates to its clients. Having many years of experience, Vallen Pro Painters ensures high quality service using the best equipment in the market, premium products, materials and trained staff. Customers satisfaction is our top priority- and Vallen Pro Painters is sure to deliver."

"Diego and his crew did an absolutely fabulous job. He checked in regularly with us before starting the job, painted sample colors on our shingles for us to see them in place and power washed the house before starting painting. They took meticulous care, caulking, sanding weathered shingles and repairing a rotted window sill. The price was very reasonable. Diego is outstandingly gracious and personable. We couldn't be happier with the job. We've worked with many contractors over the years we've had our old house, and this was the most favorable experience yet. We highly highly recommend Vallen Pro Painters!"

Tavia M on June 2022

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FAQs for deck staining or painting projects in Winchester, MA

Staining a standard 500-square-foot deck takes about 20 hours, including preparation and application. This timeline ensures a thorough job that enhances your deck's appearance and durability. The process will take longer if you include additional treatments like sealing or stripping. Weather conditions, drying time, and deck design will also impact the timeline.

You should stain your deck every two to three years to preserve its appearance and protect it from moisture, insects, and aging. Regular maintenance helps extend your deck’s lifespan and prevents costly repairs. In colder regions, staining in late spring–as soon as dry, warm conditions appear–ensures proper absorption and a long-lasting finish.

Staining your deck is a worthwhile investment. Staining protects the wood from mold, insect damage, and environmental deterioration. It preserves the deck's structural integrity while enhancing its natural beauty, adding charm and increasing property value. Restaining also reduces future repair costs, extending the deck’s lifespan for years of outdoor enjoyment.

The average cost to paint a deck is between $500 and $2,000. Hiring a professional deck stainer ensures an even, long-lasting finish, as they apply a protective layer that enhances durability and refreshes your deck’s appearance. The final cost depends on your deck size, paint quality, and labor rates.

You should always pressure wash your deck before staining to remove built-up dirt, dust, and other debris. Having a clean surface allows the stain to adhere properly, ensuring an even, long-lasting finish. Before staining, ensure the wood is completely dry to prevent moisture-related issues, which takes 24 and 48 hours.

The Winchester, MA homeowners’ guide to deck staining or paintings

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