Oil Portraits From Your Photos — Sleepy Hollow.
Start your commissionA small selection of commissions.
Every painting on this page started life as a customer’s photograph. Each was painted by hand on archival cotton canvas.
Four steps, about a fortnight.
From the photo on your camera roll to the painting on your wall.
Send the photo
Natural light works best. We’ll guide you on which photo will paint up best.
Choose & pay
Pick your size, artist tier and delivery. Pay 50% now, the rest on approval.
We paint & preview
Your assigned artist begins. You’ll see a high‑res preview before final brushstrokes.
Approve & ship
Once dry, we ship by courier. Free worldwide. Typical total: ~14 days.
What customers tell us.
Hand‑painted oil portraits, delivered to Sleepy Hollow.
Sleepy Hollow, New York – home to ~10,000 residents in the Northeast region of the United States. We deliver authentic oil paintings, hand-painted on canvas by trained artists, to every Sleepy Hollow address. Free shipping, money-back guarantee, never AI.
Local artistic heritage
New York’s portrait history is unmatched — the Met, MoMA, the Whitney, the Frick, the Met Cloisters and dozens of regional museums hold the world’s greatest collections. Our customers in Sleepy Hollow commission portraits to mark anniversaries, milestone birthdays, weddings, retirements, and to keep the memory of loved ones close.
How we paint your Sleepy Hollow portrait
- You upload your photo.
From the comfort of your Sleepy Hollow home, you upload one to five reference photos via our six-step commission flow. We accept JPG, PNG and HEIC files. Additional reference shots help with details – hair texture, jewellery, skin tone in different light.
- We assign a trained oil painter.
Within 24 hours we match your commission to one of three artist tiers – Junior, Up-and-coming, or Experienced – based on the package you have chosen. Every artist on our roster is classically trained in oil portraiture.
- Sketching, underpainting and the first colour pass.
Your artist begins with a charcoal sketch on a primed canvas, then lays down a tonal underpainting in burnt sienna or raw umber. The first colour layers establish the structure of the face and the overall composition.
- Refinement and detail work.
Subsequent layers build up the likeness – bone structure, expression in the eyes, fabric texture, hair, hands. This is the longest stage and the one that separates a competent likeness from a portrait that genuinely captures who someone is.
- Preview, varnish and delivery to Sleepy Hollow.
Before the painting is varnished and shipped, we send you a high-resolution preview by email. You can request small adjustments at no charge. Once approved, your portrait is varnished, dried, gallery-wrapped, and dispatched to your Sleepy Hollow address by tracked, fully insured courier.
Pricing & sizes for Sleepy Hollow customers
Our pricing is transparent and tier-based – the size you choose, multiplied by the artist tier, plus optional VIP express delivery. The most-ordered size in New York is the 16 inch by 20 inch canvas. Sleepy Hollow customers commissioning for formal living rooms or grand entrances often choose 24 by 30 or larger.
Venues, occasions and gifts in Sleepy Hollow
Over the past few years we have delivered portraits to Sleepy Hollow customers commissioning for an extraordinary range of occasions. Locally, anniversaries and milestone birthdays drive the bulk of our work – but we have also painted university graduates, generations of family for country club walls, posthumous tributes to grandparents, and corporate retirement gifts for executives across the wider New York area. Increasingly, we are commissioned for newborns and pets – rates of dog and cat portrait commissions in New York have more than doubled in the last two years.
Recent Sleepy Hollow commissions
“My wife wanted a painting of our wedding day for our 25th anniversary. The detail in the bouquet and the lace work alone is extraordinary.”
— Sharon D., Sleepy Hollow
“The 16 by 20 size was perfect for our hallway. Stretched canvas with no frame needed — it ships ready to hang straight out of the box.”
— Laura C., Sleepy Hollow
Photo tips for Sleepy Hollow customers
The single biggest factor in a beautiful portrait is the source photograph. Here is what we have learnt from thousands of commissions across New York and the rest of the United States:
- Use natural light. Photographs taken outdoors on an overcast day, or beside a north-facing window, give the artist the most workable detail.
- Higher resolution is better. Shoot at the highest quality your camera or phone allows. We can work from older photos, but more pixels gives us more detail to translate into oil.
- The subject should fill the frame. A close, well-composed photograph of a face will always paint better than a distant snapshot, however charming.
- Don’t worry about the background. Our artists routinely re-paint or replace backgrounds.
- Multiple photos help with composites. If you are commissioning a portrait of multiple people who were not photographed together, send up to five separate photos and we will build the composition.
Delivery to Sleepy Hollow
Standard delivery to Sleepy Hollow takes roughly 23 days from the moment you complete your commission. We ship via fully tracked, fully insured courier – typically FedEx or UPS – with signature required on delivery. Each painting is varnished, dried for 72 hours, then packed in a custom protective sleeve with corner guards and a rigid outer box. There is no shipping charge to New York, or anywhere in the United States. VIP express delivery – an additional $199 – typically reduces total turnaround to around nine days from order to Sleepy Hollow doorstep.
Care & display in Sleepy Hollow
New York’s mix of humid summers and cold winters calls for stable indoor humidity; modern HVAC keeps oils in excellent condition. For best results, hang your portrait away from direct sunlight, avoid kitchens and bathrooms where airborne moisture and grease can dull the surface, and dust gently with a soft, dry cloth no more than once a month. Should you ever notice an issue, our 100% money-back guarantee covers you for 60 days from delivery.
We also serve nearby
If you are commissioning for someone in Sleepy Hollow or the wider New York area, here are the nearest cities we also serve.
Frequently asked questions for Sleepy Hollow customers
How long does delivery to Sleepy Hollow take?
Standard delivery to Sleepy Hollow takes roughly 23 days from the moment you complete your commission. VIP express delivery brings that down to around nine days for an additional $199. All shipping is fully tracked and insured.
Do you ship to every Sleepy Hollow address?
Yes – we ship free of charge to every postal address in Sleepy Hollow and the surrounding New York area, including White Plains, Yonkers, New Rochelle. There is no minimum order value.
Can I commission a portrait from an old photograph?
Absolutely. Most of our Sleepy Hollow commissions come from photos taken years (sometimes decades) earlier – wedding photographs, family snaps, holiday memories, posthumous tributes. Our artists are skilled at restoring detail from imperfect originals.
What’s the most popular size in New York?
The 16 inch by 20 inch canvas is the most-ordered size across New York – substantial enough to anchor a wall, manageable enough to ship cleanly. Sleepy Hollow customers commissioning for formal living rooms often size up to 24 by 30.
Do you offer rush delivery for Sleepy Hollow weddings or anniversaries?
Yes – VIP express delivery cuts roughly two weeks off the standard turnaround for an additional $199. Standard Sleepy Hollow delivery is typically 23 days; VIP brings that closer to 9 days.
What is the full process for commissioning a portrait?
Six steps. Upload your photo, choose how many people are in the painting, pick your artist tier, choose your canvas size, choose standard or VIP delivery, and pay securely via Stripe. From there, your assigned artist starts work, and you will receive a high-resolution preview by email before final brushstrokes.
Will I see the painting before it is shipped to Sleepy Hollow?
Yes. Before any portrait is varnished and dispatched, we send a high-resolution preview by email. Sleepy Hollow customers can request small adjustments at no charge.
What if I do not love my finished portrait?
Every commission is covered by our 100% money-back guarantee. If you are not delighted with your portrait, return it within 60 days of delivery for a full refund. Our refund rate is below 0.5%.
Do you frame the portrait, or does it arrive unframed?
Every portrait arrives gallery-wrapped on stretched canvas, ready to hang directly out of the box – no frame required. Sleepy Hollow customers who prefer a traditional framed look typically use a local framer.
Is the portrait painted by a real artist, or is this AI?
Every portrait we deliver is painted by hand, in oils, on stretched canvas, by a trained human artist. We do not use AI.
A photograph,
painted in oils.
Six steps. About fifteen minutes. From $129.
Start now