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  • Average homeowner rating star icon4.6
    Average homeowner rating
  • Verified reviews icon455
    Verified deck repair services reviews

Top-Rated Deck repair pros in Winchester - Updated Nov 2026

Avatar for Dseventy3 Construction, LLC
Dseventy3 Construction, LLC
5.0(
29
)
Deck or Porch - Repair

Serving Winchester, MA and surrounding areas

Approved

Super Service Award Winner

In business since 1993

Free estimates

Warranties offered

"Jorge ad crew did an amazing job. I had an older deck that needed a lot of repairs. They did all the work and -painted it within a very reasonable time! Looks like a brand-new deck for Half for the money! I would recommend for sure! Thank you!"
Response time6 hrs
Response rate100%
Recommended by85%of homeowners
Avatar for DC Carpenter, LLC
DC Carpenter, LLC
4.7(
161
)
Deck or Porch - RepairDeck or Porch - Repair - For Business

Serving Winchester, MA and surrounding areas

Approved

Super Service Award Winner

In business since 2002

Free estimates

Emergency services offered

"Cosme and his crew did excellent work at a reasonable price, and did it quickly. When an unexpected rainstorm messed up the stain he had just put on the deck, he happily returned within a couple days to redo the work. Responsible, and easy to work with."
New Construction
Framing
House Wrap
Siding and Trim
Framing

+20

Response time1 day
8 neighbors recently requested a quote
Recommended by92%of homeowners
Rudy's Carpentry & Painting
4.9(
41
)
Deck or Porch - RepairDeck or Porch - Repair - For Business

Serving Winchester, MA and surrounding areas

Approved

Super Service Award Winner

In business since 2017

Free estimates

Customers say: Terrific value

"At the outset, I obtained four quotes for the work which included replacing one staircase, all railings and a few support beams and a few deck planks that were rotted. Of the four contractors that came out to visually inspect the deck, Rudy was the only one to recommend replacing all three staircases as he explained to me why they weren’t built correctly and he also recommended replacing all 16 of the support beams as the existing ones weren’t to code. The deck is 35 years old. Not only did he provide his expertise on what work was required, his quote was more than fair for the work he performed. His work is exceptional, clean and professionally managed. I recommend him highly. I’m"
Our Work
Our Work
Our Work
Our Work
Our Work

+3

Response time3 hrs
Response rate99%
43 neighbors recently requested a quote
Daniel J. O'Leary III
4.6(
62
)
Deck or Porch - Repair

Serving Winchester, MA and surrounding areas

Approved

In business since 2002

Free estimates

Small jobs welcome

"Dan did a great job doing an entire re-build of our front porch. He framed, decked (PVC) and built the railings. We are very pleased with the quality of his work. This is the second project Dan has done for us and we would highly recommend him."
Response time3 hrs
3 neighbors recently requested a quote
Recommended by96%of homeowners
Avatar for Alicandro's Painting
Alicandro's Painting
5.0(
50
)
Deck or Porch - RepairDeck or Porch - Repair - For Business

Serving Winchester, MA and surrounding areas

Approved

In business since 1999

Free estimates

Warranties offered

"Anthony and Tony did an outstanding job in restoring my front deck. They were able to remove damaged wood and replace it with new wood. The carpentry work was perfect; The entire deck was then painted, making the deck look brand new. I was impressed with the attention to detail and their meticulous approach to their work. I very much appreciate their efforts."
Response time6 hrs
Response rate96%
6 neighbors recently requested a quote
Avatar for B&D Construction and Painting, Inc.
B&D Construction and Painting, Inc.
4.7(
159
)
Deck or Porch - Repair

Serving Winchester, MA and surrounding areas

Approved

Super Service Award Winner

In business since 2017

Free estimates

Small jobs welcome

"I would recommend him and crewmen to even Kings and Queens . Benicio is a very honest, hard working and patient man. We hired the company to paint our deck. Gave him the deposit check. Two days later we started another project in the house. We called him and postponed the work for mid or late July. He didnâ t cash the check until he reached out to us in mid July to confirm that we will go forward as previously scheduled. Last weekend he came with his crew and painted the deck. We were amazed to see the care and respect they show. Although the yard is not cleaned as it is being worked on, they placed drop cloths all around the deck. They did a great job repairing the steps and painting the deck. They showed great respect to the property. They cleaned up very well before leaving. He is very honest hearted man. I We appreciated the fact that he is not money hungry. He sees people before profit. Something thatâ s very hard to find nowadays. Great Hob !!! We are very pleased."
Window before
Window install after
Response time7 hrs
Response rate90%
16 neighbors recently requested a quote
Robert Pino
4.9(
92
)
Deck or Porch - Repair

Serving Winchester, MA and surrounding areas

Approved

Super Service Award Winner

In business since 1985

Free estimates

Warranties offered

"Bob Pino did an excellent job on multiple handyman tasks in my home. He responded quickly, was very knowledgeable, thorough, professional and skilled in the work done. He completed smaller tasks and efficiently repaired an entryway ceiling, with a second person assisting to get it done quickly. His workmanship was skilled and he did a great job with numerous small repairs, installed an under cabinet TV and patiently explained pros and cons of different repair options. I recommend him highly."
Response time4 hrs
18 neighbors recently requested a quote
Recommended by58%of homeowners
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Deck Repair FAQs, answered by experts

Before installing a deck, you must build a base for the deck to rest upon, often made of compacted soil or gravel. While gravel is an optional material, it helps with drainage. Some contractors also recommend installing a weed control membrane, which helps provide a solid foundation for the frame. In the case of an elevated deck, a pro will often lay down a concrete slab as a foundation. 

In most cases, sanding an old deck before staining it is necessary to achieve a decent finish. If your old deck has a relatively new stain finish on it and you're only doing touch-ups, you can generally skip the sanding part. However, if your goal is to make the deck look and function better, sanding first is a must. 

Deck skirting shouldn’t touch the ground, especially if you have a wood deck, which is vulnerable to moisture. Ideally, you should leave at least 3/4 of an inch of space between the deck skirting and the ground for more ventilation. Pros also recommend that you incorporate about 1 square foot of space for ventilation for the underside of the deck to every 150 square feet of decking. Proper ventilation prevents mold growth and rot that can damage your deck.

A ground-level deck is a great idea for an outdoor space because it’s easy to access and doesn't require stairs or railings. You can install a ground-level deck near your home or farther away on your property. You can place a ground-level deck around a pool, fire pit, or near a view such as a lake, pond, or area of trees.

To flatten a cupped deck board, start by ensuring it’s dry. Then, try flipping the board over so the cupped side faces down and reattach it. If that’s not possible, you can use screws to pull it tighter to the joists or plane the edges slightly to reduce the cup. It’s best to replace severely cupped boards.

The Winchester, MA homeowners’ guide to deck repair services

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