From Lawn Mower to Outdoor Living Mogul: The Story of David Stockwell

by Kim Faines

When you think of someone building a business from the ground up, the story of David Stockwell stands out. At just 12 years old, he was taking a lawn‑cutting business he inherited from his brother and turning it into something much bigger—and over the years, it grew into a full design‑build firm that transforms backyard spaces across Long Island. Now, as CEO of the Deck & Patio Company, he brings that same spirit to every project: creativity, quality, and a clear focus on value.
In this article, we’ll explore David’s journey, how he views outdoor living spaces, the lessons he’s picked up along the way, and what he’s doing now to stay ahead of the curve. Whether you’re a homeowner, a real estate agent, or an investor, there are lessons here you can apply to your own property, your listings, or your business.

The Early Days: Getting a Start at Age 12

David didn’t start with big budgets. He started with neighborhood lawns and a mower. At age 12, he began helping his brother cut grass and then soon took over the business. By the time he was 17, he had two lawn‑cutting crews working for him—before even finishing high school.
That early experience taught him more than how to cut grass. It taught him responsibility, customer service, business basics, and the value of hard work. When you begin small and local, you learn fast.
He then went to college for business while still running his lawn business at night—so he was combining education with action. That set the foundation for what he would do next.

Moving into Construction and Outdoor Design

Soon after, with his landscaping business humming along, David began getting questions from clients: “Can you fix my patio?” “Can you make a new water feature?” The landscaping morphed into landscape construction: decks, patios, water features, outdoor rooms.
As he tells it, he started with the things he already knew: yards, stones, plants—and then moved into the design‑build end of the business. Instead of just mowing or planting, he was building outdoor spaces people would use. He became a licensed general contractor, and his company evolved into a full‑service design‑build firm: design, material selection, build, finish.
What’s key here is his view of transformation: He doesn’t just build a patio. He builds an outdoor living room. He doesn’t just put in a deck. He designs an experience: fire‑pit, TV wall, water feature, seating areas. He asks: What will people do here? What will they feel when they walk into this space?

Real Estate + Construction: A Smart Combo

One of the big differentiators in David’s story is that he isn’t just a contractor; he’s also a real‑estate investor. That means when he looks at a home improvement, he doesn’t just think “Will it look good?” He thinks: “Will this add value?”
When you merge construction understanding with investment strategy, you get a powerful lens. You start measuring improvements not just by cost and aesthetics, but by return on investment (ROI) and buyer experience.
For homeowners preparing to sell, David can tell you what upgrades will pay off and which won’t. For agents, he can help you understand how outdoor upgrades impact a home’s appeal and timeline. For investors, he knows how to budget, how to avoid huge losses, and how to aim for steady gains (singles and doubles rather than home‑run flips).

Why Outdoor Living Spaces Matter Today

We live in a time when the backyard is no longer a “nice to have”. It’s a lifestyle space. Why? A few key reasons:

People are staying at home more, working at home, relaxing at home. The outdoor space becomes an extension of the living room.
Buyers now expect functional outdoor areas: comfortable, usable, and well‑designed.
A great yard can differentiate a property in a crowded market; a weak yard can turn buyers away.
David points out that good outdoor design isn’t about expensive features alone—it’s about creating zones: a patio, a seating wall, a fire pit, maybe a water feature. It’s about what people do there, not just where they sit.
When preparing a home for sale, fixing up the yard can be a smart move—but doing the wrong thing can cost you. For example: installing an expensive pool might feel luxurious, but the payoff in resale might not be as high as you expect; whereas repairing a crack in the walkway, upgrading the deck, or improving the front stoop might bring stronger ROI.

The Process: How a Backyard Project Unfolds

If you decide to work with David (or a firm like his), here’s roughly how the process goes:

Initial contact: home‑owner, agent, or investor reaches out via website, Instagram, Facebook, etc.
Qualified call / questionnaire: office manager asks the right questions to determine size, scope, timeline, budget.
Walk‑through: David or a salesperson visits the property, talks with the homeowner about wish lists: What do you want? What do you already have? How do you want to live outdoors?
Design phase: He uses 2D and 3D design, so the homeowner can “walk” the backyard before build begins. That means you see where the pool would be, what the patio material looks like, water features, seating walls, TVs mounted outdoors, etc.
Material selection and value engineering: Not just what looks good—but what is durable, what adds value, what will hold up in your climate.
Permitting and planning: Because on Long Island (and in general) the building codes, townships, portals, and permit process matter a lot. Doing it early avoids surprises.
Construction and quality oversight: David emphasizes that quality matters; it isn’t just about price. The lowest bidder may not deliver the best value.
Final walkthrough and homeowner handover: The outdoor space is ready, and you’ve got your built‑for‑living backyard.

Because of his investor mindset, he builds not just for today but with resale in mind: homeowner enjoyment now and home value later.

Mistakes Homeowners (and Investors) Make

Over years of building outdoor spaces and flipping homes, David has seen common mistakes:

Choosing only based on price: “Let’s go with the cheapest bidder” can backfire if quality, materials or workmanship suffer.
Ignoring experience: Contractors who don’t understand value or resale might recommend flashy but low‑value upgrades.
Skipping early planning: Waiting to apply for permits or failing to do 3D design can lead to delays, surprises, cost overruns.
Misunderstanding ROI: Some upgrades feel luxurious but don’t add proportional value when you sell. Example: a full pool vs. patio and seating wall upgrades.
Forgetting usability: The yard must be used. A nice-looking space that no one enjoys is a missed opportunity.
David emphasizes: “There’s a cost. But there’s also a value. It’s about what you are going to experience.”

Working with Real‑Estate Agents: A Win‑Win

David has clear advice for real‑estate agents: bring someone like him in early. Why?

Because by the time you’re listing a home, you want to know what’s been done, what needs to be done, and how it will affect sale.
If you collaborate early, you can walk through the property with a contractor, identify improvements, create a plan, and avoid surprises.
Agents who understand the build/improve/sell process bring extra value to their clients. They don’t just list a house—they advise on what will make it sell and for more.
On Long‑Island especially, where each township has quirks, codes and permit differences matter. Agents who are informed help their clients avoid delays or issues.
In short: Early collaboration = faster sale, less hassle, stronger appeal.

Long Island: Challenges and Trends

Building outdoor living spaces on Long Island isn’t the same as other markets. David discusses some local challenges:

Town codes and permitting are changing fast (from 2020 to 2025 the shift is “night and day” says David).
Each township may have the same code in writing but operate differently—so experience matters.
Portals and digital applications for permits are being rolled out—but not all towns are on board. Some still prefer paper. That can create confusion.
Outdoor living trends: Because of the pandemic, people stayed home more, travel changed, lifestyles shifted. The demand for outdoor living spaces soared. David’s company added about 15 employees just to keep up with the demand.
For sellers or owners, outdoor space is no longer “nice if” but “need if”. Buyers expect usable yards. Agents and owners must adjust their expectations.
Also, resale value calculations need to reflect local market: what buyers in Suffolk, Nassau counties actually pay for outdoor living upgrades. Not all luxury features pay off equally.

What’s Next for Deck & Patio Company

David keeps thinking ahead. Here’s what’s on the horizon:

A new website that is live now, and integration of AI in client intake and project management. Soon, clients may not know if they’re talking to a human or a sophisticated chatbot/ AI‑assistant.
Streamlined workflows: the idea is to make the design‑build process faster, smoother, less error‑prone. The outdoor living company of the future isn’t just about stone and steel, but about tech and service.
Expansion of outdoor living options: more complex water features, outdoor kitchens, entertainment zones, multi‑purpose yards that move beyond the basic deck or patio.
Continued emphasis on value and quality, not just flashy upgrades. David emphasizes he doesn’t chase home‑runs on flips; he likes singles and doubles—steady wins. That same mindset applies in his business: reliable quality, repeat customers, referrals.
Training and building a team: as the company grows, he’s focused on building people, process, and culture that supports high‑end outdoor living, while remaining accessible in Long Island market.

Lessons You Can Apply Today

Whether you’re thinking of selling your home, upgrading your yard, or helping a client, here are actionable takeaways from David’s story:

Start with what people will use: A yard may look pretty, but will people want to spend time there? Design for living.
Quality matters more than lowest cost: The lowest bid sometimes hides compromises. Ask about materials, warranty, timeline, references.
Think about resale value: Some upgrades look amazing but won’t bring the same return when you sell. Balance lifestyle now with value later.
Get design and walkthroughs: 3D renderings, design plans help reduce surprises. You’ll know what you’re building ahead of time.
Bring in professionals early: Realtors, contractors, designers—all should talk early so the project aligns with listing, market and permits.
Understand your local rules: On Long Island (and many places) each township operates differently. Know the permit process, delays, codes.
Set realistic expectations: Outdoor living is an investment—not just in money, but in time, lifestyle, and maintenance.
Use tech to your benefit: Whether for client management, design review, communication—automation and innovation matter.
Focus on zones, not just features: Rather than “I want a pool”, think “I want an outdoor living area where we’ll hang out after dinner”. The difference matters.
Team mindset matters: Whether you’re an investor, agent, homeowner or contractor—working together yields better results than going it alone.

Why David’s Story Resonates

There’s something universally relatable about the story of someone starting small, staying consistent, and building something meaningful. David’s story—from a 12‑year‑old mowing lawns to a CEO leading a design‑build firm—shows the power of resilience, vision and hard work.
Moreover, his dual lens of investment and construction gives him perspective that many contractors don’t have. He doesn’t just build patios; he builds value. He doesn’t just design backyards; he designs lifestyle and resale potential.
And his commitment to quality, process, and client experience means that the people using his outdoor spaces aren’t just “getting a patio”—they’re getting a place where memories happen, where families gather, where homes feel bigger because the outdoors counts too.
In today’s real‑estate landscape, the outdoor component is no longer optional—it’s essential. And professionals who understand that, like David, are helping shape what “home” truly means in modern American living.

Final Thoughts

If you’re a homeowner thinking: “Should I invest in my backyard?”, ask yourself these questions:

What do I want to do out there?
Will a new patio, deck, or water‑feature bring me joy and make sense in resale?
Is the contractor I’m considering someone who cares about quality and value—or just offering the cheapest price?
Have I considered the permit process, the local township rules, and the timeline to build?
Can I picture the finished space? Have I seen a 3D model or designed walkthrough?

If you’re an agent, ask:

Have I brought a contractor in yet to walk the property?
Do I understand which outdoor upgrades will move the listing faster?
Am I advising my clients (sellers or buyers) about the outdoor experience and value—not just the bedrooms and bathrooms?

And if you’re an investor:

Does the outdoor component make sense for the budget, timeline and exit strategy?
Are upgrades focusing on functionality and appeal rather than just “flash”?
Is our team aligned—contractor, designer, real estate agent, financier?

David Stockwell’s journey and philosophy give us a blueprint: start simple, build smart, focus on quality, live for now and value for later. When done right, outdoor living spaces don’t just add beauty—they create lifestyle, engagement and measurable value.
If you’re ready to upgrade your outdoor space or strategize your next real‑estate move, remember: the backyard isn’t just grass anymore—it’s your next big room.
And for that kind of transformation, the right partner, process and mindset make all the difference.

Visit www.dreamselectrealty.com or contact us at 631‑623‑7117. Follow us on Instagram and TikTok @dreamselectrealty, Twitter @dreamselecthome, or email hometeam@dreamselectrealty.com for the latest updates on homes for sale on Long Island in New York.