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Top-Rated Exterior home or structure paint or stainers in Middletown - Updated Nov 2026

Avatar for Tolbert & Sons Custom Painting LLC
Tolbert & Sons Custom Painting LLC
4.7(
27
)
Exterior Home or Structure - Paint or Stain

Serving Middletown, DE and surrounding areas

Approved

In business since 1992

Free estimates

Emergency services offered

"The garage turned out well. There were a few things done that was not perfect. They painted over some light bulbs and covers. The basement turned out great as well. There were several guys that came out and completed the project (including a ridiculous amount of nail pops) in just 3 days. This was the quaility of work I expected for the main 2 floors. The interior was another story. I was told when I received the bid that it would be a project that was squeezed in since they were very booked. Price was lower than the competitors so we hired. The company sent out 1 man to conduct the job. He was all over the place, missed spots and I was getting very stressed out. He fixed some nail pops but didn’t complete all of them. Additionally we would come home and see furniture and new carpet had not been covered up. Brush lines are still visable in spots along with paint runs. The home was empty and without furniture for 1 month. They were unable to complete the job while it was empty. The company had to come out after the pervious sub contractor was complete to try and fix and better the quality of the final product. Additionally, not everything was as it should be when final payment was made. There are stilll definite brush marks and color differences along all the corners and seems. Due to furniture being delivered that was too heavy to move, I will have to ask them to come out when we move again to see if they can finish some spots. The crew that came out to fix the job did well but there was so much space to cover they didn’t get everything. We are still noticing spots along the home that weren’t caught."
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+83

Response time4 days
2 neighbors recently requested a quote
Recommended by92%of homeowners
Avatar for David Docherty Contracting
David Docherty Contracting
4.9(
27
)
Exterior Home or Structure - Paint or Stain

Serving Middletown, DE and surrounding areas

Approved

Super Service Award Winner

In business since 1990

Free estimates

Emergency services offered

"David Docherty & Son team completed a phenomenal exterior paint job on my home. They transformed a dated Brown house to this Updated Black & White Clean look. Besides a few days of weather restrictions, they worked quickly and efficiently. I am really pleased with the outcome. They are friendly and professional."
Deck Maintenance Project
Deck Maintenance Project
Additional Photos
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+12

10 neighbors recently requested a quote
Recommended by61%of homeowners
Avatar for Day Painter
Day Painter
4.4(
15
)
Exterior Home or Structure - Paint or Stain

Serving Middletown, DE and surrounding areas

Approved

In business since 2014

Free estimates

Warranties offered

"Very responsive, estimate within a day from contact. Readily adjusted estimate with added services. Power washed within 2 days of excepting estimate on Saturday. Sanded, painted and finished on Monday trim, shutters, soffits, gutters, bay window with wall boxes and front door of townhouse. Corrected missed caulking immediately without hesitation. Excellent work overall, would use again!"
paint
paint
Siding
Siding
interior

+9

Response time1 day
1 neighbors recently requested a quote
Recommended by90%of homeowners
Benny Bennett Contracting
4.4(
112
)
Exterior Home or Structure - Paint or Stain

Serving Middletown, DE and surrounding areas

Approved

In business since 2013

Free estimates

Credit card accepted

"I use Benny Bennett Contracting for a gutter repair project that I needed to complete and was very please with both the suggestions and cost. Additionally I was happy with the expediency that was put on this project and the speed and professionalism that was demonstrated by this contracting pro. I give my highest recommendation to Benny Bennett Contracting for all of your exterior housing needs."
Response time1 day
Response rate91%
33 neighbors recently requested a quote
Avatar for MAX Painting, LLC
MAX Painting, LLC
4.9(
11
)
Exterior Home or Structure - Paint or Stain

Serving Middletown, DE and surrounding areas

Approved

In business since 2022

Free estimates

Emergency services offered

"I’m so happy that I chose Max Painting!! My project was done within the time frame we discussed and it looks so great! He was attentive to my request and the outcome of the project! I will definitely use their services again!"
Nursery
Nursey
Interior
Interior
Interior

+5

Response time3 hrs
Response rate100%
Recommended by100%of homeowners
Avatar for Paddy's LLC
Paddy's LLC
4.3(
218
)
Exterior Home or Structure - Paint or Stain

Serving Middletown, DE and surrounding areas

Approved

In business since 2023

Free estimates

Warranties offered

"They did a great job on the roof at a reasonable price in comparison to the other quotes I received from other big name companies. Roof was a 20 year old and need an update. Appreciate, the straight to the point sales pitch. Constant communication throughout the process. Happy with the job thus far. Will continue to monitor for any issues."
Before
After
After
Before
During

+111

Response time1 day
Response rate94%
25 neighbors recently requested a quote
Avatar for Fine Painters Inc
Fine Painters Inc
4.4(
281
)
Exterior Home or Structure - Paint or Stain

Serving Middletown, DE and surrounding areas

In business since 1996

Free estimates

Emergency services offered

"They really are not that good because the work they did started to deteriorate quickly after they did it. They came back and resolved the problem but they also did additional work; they really are not the best painters. The price was very reasonable and they also did some exterior painting for me as well. The interior painting was not as professional as I thought it could have been but they were quick to respond to my needs. They were punctual."
Recommended by89%of homeowners
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FAQs for exterior home or structure paint or stain projects in Middletown, DE

For aluminum siding, go with a high-quality 100% acrylic exterior paint. Start with an oil-based primer to ensure the finish adheres and shields the metal from oxidation and moisture. The primer seals the surface and provides the acrylic with a surface to grip. Skip latex primers or paints—their reaction with aluminum can trap bubbles and cause early peeling.

How long will painted aluminum siding last?

A well-done paint job on aluminum siding can last around 15 years, making the upfront effort worthwhile. Longevity hinges on solid prep: thoroughly cleaning the surface to remove chalky residue, dirt, and mildew so the new paint can adhere properly. It’s also important to paint when temperatures are between 50°F and 80°F, as extreme heat or cold can affect drying and adhesion. Steer clear of rainy days—moisture under the paint weakens adhesion and speeds up peeling or fading, which can significantly shorten the lifespan of your fresh coat.

Plan on repainting when the finish starts fading or leaves a chalky, white residue on your hand. Check the siding each year; if there’s a powdery residue on your palm, it indicates oxidation is underway on your siding. A fresh coat of paint stops peeling before it starts, boosts curb appeal, and keeps the metal protected.

Spray painting aluminum siding offers significant benefits compared to other application styles. Spray painting delivers even coverage, rapid application, and enhanced adhesion compared to traditional painting methods. This technique ensures every surface is evenly coated, minimizes labor time, and provides a sleek, professional finish that withstands weather and oxidation for lasting results.

The return on investment for aluminum siding is 70%. For example, a $10,000 aluminum siding installation will add $7,000 to your home’s resale value. Regional housing markets, the quality of siding materials, and ongoing upkeep—including repainting and repairs—influence final ROI. Investing in professional installation and regular maintenance ensures you recoup a significant portion of your siding costs when it’s time to sell.

Several materials can replace aluminum siding, each offering unique trade-offs. Vinyl siding requires minimal upkeep and resists fading, lasting up to 30 years. Wood siding provides classic warmth but demands regular painting or sealing. Fiber cement and composite siding offer exceptional durability and design flexibility, requiring minimal maintenance. Brick veneer and stucco create premium, long-lasting exteriors, but they come with higher upfront costs and increased installation complexity.

The Middletown, DE homeowners’ guide to exterior home or structure paint or stains

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