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Massachusetts - Portrait Paintings

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Item Ships From: Massachusetts
"Self Portrait Painting", contemporary, portrait, collage, blue, mixed media
By John Baker
Located in Natick, MA
John Baker’s “Self Portrait Painting” is an acrylic on canvas with collage 32 x 27.5 inches in russets and greys with bursts and dispersions of prismatic highlights, chiefly blues, yellows and reds. The artist, with loaded palette and brush, is simultaneously his actual self and the image of himself...
Category

2010s Contemporary Massachusetts - Portrait Paintings

Materials

Canvas, Mixed Media, Acrylic

"Self Portrait Painting", contemporary, portrait, collage, blue, mixed media
"Self Portrait Painting", contemporary, portrait, collage, blue, mixed media

John Baker
"Self Portrait Painting", contemporary, portrait, collage, blue, mixed media, 2011

$2,400
Boy Reading, Original Painting
By Jessica JH Roller
Located in San Francisco, CA

Artist Comments
An eight-year-old boy, thoughtfully engaged in reading one early autumn morning. This painting depicts the artist Jessica JH Roller's son, Fox, calmly immerse...

Category

21st Century and Contemporary Outsider Art Massachusetts - Portrait Paintings

Materials

Acrylic

Boy Reading, Original Painting
Boy Reading, Original Painting

Jessica JH Roller
Boy Reading, Original Painting, 2023

$650
Resting, Oil Painting
By Mary Pratt
Located in San Francisco, CA

Artist Comments
In a serene setting, a female figure clad in a white gown gracefully balances herself while holding onto a branch. Her steady, down-turned gaze suggests a mom...

Category

21st Century and Contemporary Contemporary Massachusetts - Portrait Paintings

Materials

Oil

Resting, Oil Painting
Resting, Oil Painting

Mary Pratt
Resting, Oil Painting, 2024

$1,975
Only Red, Oil Painting
By Mary Pratt
Located in San Francisco, CA

Artist Comments
A geisha, adorned in a red dress with a floral pattern, moves gracefully. The composition places her off-center, shifting the oversized parasol to the right f...

Category

21st Century and Contemporary Contemporary Massachusetts - Portrait Paintings

Materials

Oil

Only Red, Oil Painting
Only Red, Oil Painting

Mary Pratt
Only Red, Oil Painting, 2024

$1,050
"Best of Both Worlds II", collage, portrait, tan, grey, green, acrylic painting
By John Baker
Located in Natick, MA
John Baker’s “Best of Both Worlds II”, an acrylic painting on canvas with collage 25 x 22 x 1.5 inches (frame 4 inches wide), is a self-portrait in...
Category

2010s Contemporary Massachusetts - Portrait Paintings

Materials

Canvas, Mixed Media, Acrylic

"Best of Both Worlds II", collage, portrait, tan, grey, green, acrylic painting
"Best of Both Worlds II", collage, portrait, tan, grey, green, acrylic painting

John Baker
"Best of Both Worlds II", collage, portrait, tan, grey, green, acrylic painting, 2012

$2,500
"Eating and Drinking I", Surrealist, Red, Green, Yellow, Acrylic Painting, 2022
By John Baker
Located in Natick, MA
John Baker’s “Eating and Drinking I” is an acrylic painting on canvas with collage 24 x 30 inches in reds, greens and yellows against a neutral background. What at first glance appea...
Category

2010s Surrealist Massachusetts - Portrait Paintings

Materials

Canvas, Acrylic, Mixed Media

"Eating and Drinking I", Surrealist, Red, Green, Yellow, Acrylic Painting, 2022
"Eating and Drinking I", Surrealist, Red, Green, Yellow, Acrylic Painting, 2022

John Baker
"Eating and Drinking I", Surrealist, Red, Green, Yellow, Acrylic Painting, 2022, 2022

$2,100
The Happiness of Each Flower, Oil Painting
Located in San Francisco, CA

Artist Comments
A girl carries freshly picked daisies as she walks through a meadow. The beauty of the flowers, the clear sky, and her presence convey peace and a deep connec...

Category

21st Century and Contemporary Realist Massachusetts - Portrait Paintings

Materials

Oil

The Happiness of Each Flower, Oil Painting
The Happiness of Each Flower, Oil Painting

Jose Luis Bermudez
The Happiness of Each Flower, Oil Painting, 2023

$3,800
August 19, 1998 (98-99 Series), Original Painting
By Mark Cudd
Located in San Francisco, CA

Artist Comments
Artist Mark Cudd reflects on his experiences from 1998–1999 through his ongoing series of expressive portraits and symbolic imagery. This piece offers a windo...

Category

21st Century and Contemporary Pop Art Massachusetts - Portrait Paintings

Materials

Acrylic

August 19, 1998 (98-99 Series), Original Painting
August 19, 1998 (98-99 Series), Original Painting

Mark Cudd
August 19, 1998 (98-99 Series), Original Painting, 2025

$375
Elegant, Original Painting
By Sharon Sieben
Located in San Francisco, CA

Artist Comments
"She emanates an aura of quiet strength while maintaining a delicate presence at the same time," says artist Sharon Sieben. She captures a woman mid-stride, w...

Category

21st Century and Contemporary Outsider Art Massachusetts - Portrait Paintings

Materials

Acrylic

Elegant, Original Painting
Elegant, Original Painting

Sharon Sieben
Elegant, Original Painting, 2023

$1,575
Denim and Red Boots, Original Painting
Located in San Francisco, CA

Artist Comments
A fashionable young woman sporting sunglasses, favorite denim pants, and vibrant red boots steps out into a windy early spring day for a brisk walk with her c...

Category

21st Century and Contemporary Outsider Art Massachusetts - Portrait Paintings

Materials

Acrylic

Denim and Red Boots, Original Painting
Denim and Red Boots, Original Painting

Lee Smith
Denim and Red Boots, Original Painting, 2023

$500
Spring Forward, Original Painting
By Robin Okun
Located in San Francisco, CA

Artist Comments
Vivid colors and dynamic brushstrokes come together in this garden scene. Part of artist Robin Okun's series that explores lighter and more illuminative color...

Category

21st Century and Contemporary Contemporary Massachusetts - Portrait Paintings

Materials

Acrylic

Spring Forward, Original Painting
Spring Forward, Original Painting

Robin Okun
Spring Forward, Original Painting, 2023

$2,300
Leaning into the Light, Original Painting
By Robin Okun
Located in San Francisco, CA

Artist Comments
Blocks of vibrant pinks and blues, highlighted with yellow, radiate an uplifting sense of energy. While the figure appears firmly planted in the foreground, t...

Category

21st Century and Contemporary Contemporary Massachusetts - Portrait Paintings

Materials

Acrylic

Leaning into the Light, Original Painting
Leaning into the Light, Original Painting

Robin Okun
Leaning into the Light, Original Painting, 2023

$1,100
Here I Am, Original Painting
By Nava Lundy
Located in San Francisco, CA

Artist Comments
This portrait shows a young woman wearing a flower crown. Her presence radiates the strength, power, and beauty reminiscent of a goddess. Her fixed gaze expre...

Category

21st Century and Contemporary Contemporary Massachusetts - Portrait Paintings

Materials

Acrylic

Here I Am, Original Painting
Here I Am, Original Painting

Nava Lundy
Here I Am, Original Painting, 2023

$5,000
"Down he Goes V", contemporary, portrait, male, grey, acrylic, collage, painting
By John Baker
Located in Natick, MA
John Baker’s “Down he Goes V,” an acrylic painting on collage with collage 20 x 16 inches in yellow and red ochres with black and greys, is from the artist’s new “Fall of the White M...
Category

2010s Contemporary Massachusetts - Portrait Paintings

Materials

Canvas, Mixed Media, Acrylic

"Down he Goes V", contemporary, portrait, male, grey, acrylic, collage, painting
"Down he Goes V", contemporary, portrait, male, grey, acrylic, collage, painting

John Baker
"Down he Goes V", contemporary, portrait, male, grey, acrylic, collage, painting, 2021

$1,300
Tale of Two Moons, Oil Painting
By Mary Pratt
Located in San Francisco, CA

Artist Comments
Three graceful geishas walk toward the distant temple. Their elegant presence matches their beautifully adorned parasols and kimonos. Two crescent moons and t...

Category

21st Century and Contemporary Contemporary Massachusetts - Portrait Paintings

Materials

Oil

Tale of Two Moons, Oil Painting
Tale of Two Moons, Oil Painting

Mary Pratt
Tale of Two Moons, Oil Painting, 2023

$3,800
Daydreaming, Oil Painting
By Kristen Brown
Located in San Francisco, CA

Artist Comments
Artist Kristen Brown depicts an ambiguous figure of a woman with long hair. The speckled blurs create dynamism and charisma in the dreamy portrait. Overlappin...

Category

21st Century and Contemporary Contemporary Massachusetts - Portrait Paintings

Materials

Oil

Daydreaming, Oil Painting
Daydreaming, Oil Painting

Kristen Brown
Daydreaming, Oil Painting, 2023

$425
Portrait in Wildflowers, Original Painting
By Jessica JH Roller
Located in San Francisco, CA

Artist Comments
Artist Jessica JH Roller paints a woman sitting on the ground with her legs crossed. Vibrant wildflowers in pink and red thrive all around her. "Summer is in ...

Category

21st Century and Contemporary Outsider Art Massachusetts - Portrait Paintings

Materials

Acrylic

Portrait in Wildflowers, Original Painting
Portrait in Wildflowers, Original Painting

Jessica JH Roller
Portrait in Wildflowers, Original Painting, 2023

$500
That Guy Mike, Original Painting
Located in San Francisco, CA

Artist Comments
"That guy Mike looks nothing like him," says artist John McCabe. "His hair isn't quite so aqua. Maybe they are the same height." He...

Category

21st Century and Contemporary Pop Art Massachusetts - Portrait Paintings

Materials

Acrylic

That Guy Mike, Original Painting
That Guy Mike, Original Painting

John McCabe
That Guy Mike, Original Painting, 2022

$325
"Being and Time: An Imaginary Portrait of Martin Heidegger", Acrylic Painting
By John Baker
Located in Natick, MA
John Baker’s “Being and Time: an Imaginary Portrait of Martin Heidegger” is an acrylic painting on canvas with collage 28 x 22 inches in green, greys and silver, with maroon highligh...
Category

2010s Surrealist Massachusetts - Portrait Paintings

Materials

Canvas, Acrylic

"Being and Time: An Imaginary Portrait of Martin Heidegger", Acrylic Painting
"Being and Time: An Imaginary Portrait of Martin Heidegger", Acrylic Painting

John Baker
"Being and Time: An Imaginary Portrait of Martin Heidegger", Acrylic Painting, 2025

$1,600
Grapeshot, Oil Painting
By David Shepherd
Located in San Francisco, CA

Artist Comments
Artist David Shepherd paints a hyperrealistic portrait of a woman adorned with white flowers. "The eye is like a fingerprint, it uniquely identifies us," says...

Category

21st Century and Contemporary Realist Massachusetts - Portrait Paintings

Materials

Oil

Grapeshot, Oil Painting
Grapeshot, Oil Painting

David Shepherd
Grapeshot, Oil Painting, 2022

$4,725
"The Lonely Crowd", surrealist, portrait, mixed media, acrylic painting
By John Baker
Located in Natick, MA
John Baker’s “The Lonely Crowd” is a multi-colored acrylic painting on canvas with collage 40 x 60 inches. Blues, yellows and greens predominate while reds provide color accents. The...
Category

2010s Surrealist Massachusetts - Portrait Paintings

Materials

Canvas, Mixed Media, Acrylic

"The Lonely Crowd", surrealist, portrait, mixed media, acrylic painting
"The Lonely Crowd", surrealist, portrait, mixed media, acrylic painting

John Baker
"The Lonely Crowd", surrealist, portrait, mixed media, acrylic painting, 2022

$4,000
Maternidad
By Ramon Pichot i Soler
Located in Sheffield, MA
Ramon Pichot Soler Spanish, 1924-1996 Maternidad Oil on canvas 15 by 18 in, w/ frame 22 by 24 ¾ in Signed lower left
Category

Late 20th Century Contemporary Massachusetts - Portrait Paintings

Materials

Oil

Maternidad
Maternidad

Ramon Pichot i Soler
Maternidad

$3,000
"Oni Fila Gogoro lll" proud side profile of woman with colorful accessories
By Affen Segun
Located in Edgartown, MA
The newest from Affen Segun's studio: Affen Segun was born in 1993 in Lagos, Nigeria. A native of Bayelsa State, he discovered his love for art at a young age, and later got enrolled...
Category

2010s Contemporary Massachusetts - Portrait Paintings

Materials

Fabric, Canvas, Acrylic, Mixed Media

"Oni Fila Gogoro lll" proud side profile of woman with colorful accessories

Affen Segun
"Oni Fila Gogoro lll" proud side profile of woman with colorful accessories, 2025

$3,800
"Old Madman 4", Contemporary, Portrait, Brown, Collage, Acrylic Painting, 2020
By John Baker
Located in Natick, MA
John Baker’s “Old Madman #4”, an imaginary portrait 14 x 18 x .75 inches in flesh tones, greys, browns and whites, is from the artist’s important “Madman Series”. As Yeats wrote: “An...
Category

2010s Contemporary Massachusetts - Portrait Paintings

Materials

Canvas, Mixed Media, Acrylic

"Old Madman 4", Contemporary, Portrait, Brown, Collage, Acrylic Painting, 2020
"Old Madman 4", Contemporary, Portrait, Brown, Collage, Acrylic Painting, 2020

John Baker
"Old Madman 4", Contemporary, Portrait, Brown, Collage, Acrylic Painting, 2020, 2020

$800
Portrait 25-6, Original Painting
Located in San Francisco, CA

Artist Comments
Green, blue, and metallic gold dots form a woman's portrait against a black background. Artist Hyoungseok Kim painted this piece using pointillism. He emphasi...

Category

21st Century and Contemporary Contemporary Massachusetts - Portrait Paintings

Materials

Acrylic

Portrait 25-6, Original Painting
Portrait 25-6, Original Painting

Hyoungseok Kim
Portrait 25-6, Original Painting, 2025

$900
"Multiple Personality Disorder", portrait, collage, black, mixed media painting
By John Baker
Located in Natick, MA
John Baker’s “Multiple Personality Disorder” is an acrylic painting on canvas with collage and custom frame 28 x 26.5 x 4 inches in greys, blacks, whites and flesh tones. Outer and i...
Category

2010s Contemporary Massachusetts - Portrait Paintings

Materials

Canvas, Mixed Media, Acrylic

"Multiple Personality Disorder", portrait, collage, black, mixed media painting
"Multiple Personality Disorder", portrait, collage, black, mixed media painting

John Baker
"Multiple Personality Disorder", portrait, collage, black, mixed media painting, 2019

$3,600
"He Stayed Behind in Katmandu II", Contemporary, Portrait, Collage, Mixed Media
By John Baker
Located in Natick, MA
John Baker’s “He Stayed Behind in Katmandu II” is an acrylic portrait painting on canvas with collage 20.25 x 17.75 x 1.5 inches in blues, tans, pinks and flesh tones. The western “s...
Category

2010s Contemporary Massachusetts - Portrait Paintings

Materials

Acrylic, Mixed Media, Canvas

"He Stayed Behind in Katmandu II", Contemporary, Portrait, Collage, Mixed Media
"He Stayed Behind in Katmandu II", Contemporary, Portrait, Collage, Mixed Media

John Baker
"He Stayed Behind in Katmandu II", Contemporary, Portrait, Collage, Mixed Media, 2012

$800 Sale Price
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Portrait 25-4, Original Painting
Located in San Francisco, CA

Artist Comments
A portrait emerges from different-colored and metallic golden dots, forming a serene yet enigmatic face against a black background. Subtle shifts in color bri...

Category

21st Century and Contemporary Contemporary Massachusetts - Portrait Paintings

Materials

Acrylic

Portrait 25-4, Original Painting
Portrait 25-4, Original Painting

Hyoungseok Kim
Portrait 25-4, Original Painting, 2025

$900
"The Ego and the Id", Contemporary Portrait, Red, Collage, Acrylic Painting
By John Baker
Located in Natick, MA
John Baker’s “The Ego and the Id” is an imaginary portrait, acrylic on canvas with collage 15 x 10 x 1.5 inches in flesh tones, greys and tans with red highlights. The painting’s tit...
Category

2010s Contemporary Massachusetts - Portrait Paintings

Materials

Canvas, Mixed Media, Acrylic

"The Ego and the Id", Contemporary Portrait, Red, Collage, Acrylic Painting
"The Ego and the Id", Contemporary Portrait, Red, Collage, Acrylic Painting

John Baker
"The Ego and the Id", Contemporary Portrait, Red, Collage, Acrylic Painting, 2011

$1,900
“Under a Summer Sky” blonde woman with purple bathing suit relaxes in the pool
Located in Edgartown, MA
James Wolanin’s paintings transport the viewer to an effervescent, candy coated world inspired by vintage advertisements, photographs, and the artist’s own personal history. The Russ...
Category

2010s Massachusetts - Portrait Paintings

Materials

Acrylic, Wood Panel

“Under a Summer Sky” blonde woman with purple bathing suit relaxes in the pool

“Under a Summer Sky” blonde woman with purple bathing suit relaxes in the pool, 2025

$7,500
"Down he Goes III", contemporary, portrait, male, collage, acrylic painting
By John Baker
Located in Natick, MA
John Baker’s “Down he Goes III,” an acrylic painting on canvas with collage 20 x 16 inches in silver greys and yellows, is from the artist’s new “Fall of the White Male Series.” The ...
Category

2010s Contemporary Massachusetts - Portrait Paintings

Materials

Canvas, Mixed Media, Acrylic

"Down he Goes III", contemporary, portrait, male, collage, acrylic painting
"Down he Goes III", contemporary, portrait, male, collage, acrylic painting

John Baker
"Down he Goes III", contemporary, portrait, male, collage, acrylic painting, 2021

$1,400
"Down he Goes IV", contemporary, portrait, male, grey, collage, acrylic painting
By John Baker
Located in Natick, MA
John Baker’s “Down he Goes IV,” an acrylic painting on canvas with collage 20 x 16 inches in yellow and red ochres with blacks and greys, is from the artist’s “Fall of the White Male...
Category

2010s Contemporary Massachusetts - Portrait Paintings

Materials

Canvas, Mixed Media, Acrylic

"Down he Goes IV", contemporary, portrait, male, grey, collage, acrylic painting
"Down he Goes IV", contemporary, portrait, male, grey, collage, acrylic painting

John Baker
"Down he Goes IV", contemporary, portrait, male, grey, collage, acrylic painting, 2021

$1,300
"Sanctuary Morning", Contemporary Portrait, Green, Collage, Mixed Media Painting
By John Baker
Located in Natick, MA
John Baker’s “Sanctuary Morning” is an acrylic painting on canvas with collage 63 x 51 x 1.5 inches pervaded by the many different greens of a New England Forest in early spring. Sha...
Category

Early 2000s Contemporary Massachusetts - Portrait Paintings

Materials

Canvas, Mixed Media, Acrylic

"Sanctuary Morning", Contemporary Portrait, Green, Collage, Mixed Media Painting
"Sanctuary Morning", Contemporary Portrait, Green, Collage, Mixed Media Painting

John Baker
"Sanctuary Morning", Contemporary Portrait, Green, Collage, Mixed Media Painting, 2004

$7,000
"Family Picnic by the Sea" children enjoying a picnic and cake with their father
Located in Edgartown, MA
Since summer 2004, I have lived in southern Italy, in the region of Puglia, the province of Bari, in a town called Altamura. A two-week restoration project of the Jesce Masseria brou...
Category

2010s Impressionist Massachusetts - Portrait Paintings

Materials

Canvas, Oil

"Family Picnic by the Sea" children enjoying a picnic and cake with their father
"Family Picnic by the Sea" children enjoying a picnic and cake with their father

Jennifer Bell
"Family Picnic by the Sea" children enjoying a picnic and cake with their father, 2025

$4,400
"Shared Visions, Beyond Today" Couple with patterned clothes look towards nature
By Janice Frame
Located in Edgartown, MA
"As an African-American artist in today’s world, I embody the vast differences found in our collective backgrounds. I view them as cultural assets. We are always self discovering and...
Category

2010s Contemporary Massachusetts - Portrait Paintings

Materials

Mixed Media, Board, Watercolor

"Shared Visions, Beyond Today" Couple with patterned clothes look towards nature
"Shared Visions, Beyond Today" Couple with patterned clothes look towards nature

Janice Frame
"Shared Visions, Beyond Today" Couple with patterned clothes look towards nature, 2025

$2,600
"A Treat for Sasha", contemporary, portrait, green, brown, red, collage, acrylic
By John Baker
Located in Natick, MA
John Baker’s “A Treat for Sasha” is an acrylic painting on canvas with collage 36 x 24 x 1.5 inches in oranges, greens, browns and reds. The twirling hands of the pet owner manipulat...
Category

2010s Contemporary Massachusetts - Portrait Paintings

Materials

Canvas, Mixed Media, Acrylic

"A Treat for Sasha", contemporary, portrait, green, brown, red, collage, acrylic
"A Treat for Sasha", contemporary, portrait, green, brown, red, collage, acrylic

John Baker
"A Treat for Sasha", contemporary, portrait, green, brown, red, collage, acrylic, 2020

$3,200
"Shotgun Wedding", portrait, bride, green, white, collage, acrylic painting
By John Baker
Located in Natick, MA
John Baker’s “Shotgun Wedding” is an acrylic painting on canvas with collage 56 x 30 x 1.5 inches in greens, whites, flesh tones and yellows. The bride is radiant on her wedding day,...
Category

2010s Contemporary Massachusetts - Portrait Paintings

Materials

Canvas, Mixed Media, Acrylic

"Shotgun Wedding", portrait, bride, green, white, collage, acrylic painting
"Shotgun Wedding", portrait, bride, green, white, collage, acrylic painting

John Baker
"Shotgun Wedding", portrait, bride, green, white, collage, acrylic painting, 2018

$4,500
"Pacific Celebration", contemporary, collage, blue, yellow, red, mixed media
By John Baker
Located in Natick, MA
John Baker’s “Pacific Celebration” is an acrylic painting with collage on canvas 66 x 50 inches in greens, blues, yellows and rose reds. As though at a fantastical wedding, the color...
Category

2010s Contemporary Massachusetts - Portrait Paintings

Materials

Canvas, Mixed Media, Acrylic

"Pacific Celebration", contemporary, collage, blue, yellow, red, mixed media
"Pacific Celebration", contemporary, collage, blue, yellow, red, mixed media

John Baker
"Pacific Celebration", contemporary, collage, blue, yellow, red, mixed media, 2011

$6,000
"Oni Fila Gogoro lX" woman in with patterned bandana and hat rests in confidence
By Affen Segun
Located in Edgartown, MA
The newest from Affen Segun's studio: Affen Segun was born in 1993 in Lagos, Nigeria. A native of Bayelsa State, he discovered his love for art at a young age, and later got enrolled...
Category

2010s Contemporary Massachusetts - Portrait Paintings

Materials

Fabric, Canvas, Mixed Media, Acrylic

"Oni Fila Gogoro lX" woman in with patterned bandana and hat rests in confidence

Affen Segun
"Oni Fila Gogoro lX" woman in with patterned bandana and hat rests in confidence, 2025

$4,600
"The Two Dummies", surrealist, brown, tan, grey, mixed media, acrylic painting
By John Baker
Located in Natick, MA
John Baker’s “The Two Dummies” is an acrylic painting on canvas with collage 32 x 24 x 1.5 inches wide in browns, tans and greys with red and yellow accents. The wooden neck lever of the ventriloquist suggests that he is in reality the dummy of the young boy; and yet, impossibly, both seem to be the dummies of one another! Regardless, the brightness of the props on the prop table...
Category

2010s Surrealist Massachusetts - Portrait Paintings

Materials

Canvas, Mixed Media, Acrylic

"The Two Dummies", surrealist, brown, tan, grey, mixed media, acrylic painting
"The Two Dummies", surrealist, brown, tan, grey, mixed media, acrylic painting

John Baker
"The Two Dummies", surrealist, brown, tan, grey, mixed media, acrylic painting, 2023

$2,900
"Young Man with a Bouquet of his own Thoughts", Collage, Acrylic Painting, 2005
By John Baker
Located in Natick, MA
John Baker’s “Young Man with a Bouquet” is an acrylic painting on canvas with collage 48 x 36 inches in strong yellows, reds, blues and greens. The painting depicts a youth sadly co...
Category

Early 2000s Contemporary Massachusetts - Portrait Paintings

Materials

Canvas, Mixed Media, Acrylic

"Young Man with a Bouquet of his own Thoughts", Collage, Acrylic Painting, 2005
"Young Man with a Bouquet of his own Thoughts", Collage, Acrylic Painting, 2005

John Baker
"Young Man with a Bouquet of his own Thoughts", Collage, Acrylic Painting, 2005, 2005

$2,900
"Amy" side profile of a woman with white bathing suit floating up for air
By Carol Bennett
Located in Edgartown, MA
"I throw myself into the water almost every day- it grounds me, the body floats and the mind drifts. The "Swimmer series" has followed me over the years, resurfacing and evolving. Pr...
Category

2010s Contemporary Massachusetts - Portrait Paintings

Materials

Canvas, Oil

"Amy" side profile of a woman with white bathing suit floating up for air
"Amy" side profile of a woman with white bathing suit floating up for air

Carol Bennett
"Amy" side profile of a woman with white bathing suit floating up for air, 2024

$3,200
"Harmony" pop art paining of a woman in pink bathing suit relaxing in the pool
By James Wolanin
Located in Edgartown, MA
James Wolanin’s paintings transport the viewer to an effervescent, candy coated world inspired by vintage advertisements, photographs, and the artist’s own personal history. The Russ...
Category

2010s Contemporary Massachusetts - Portrait Paintings

Materials

Acrylic, Wood Panel

"Harmony" pop art paining of a woman in pink bathing suit relaxing in the pool

James Wolanin
"Harmony" pop art paining of a woman in pink bathing suit relaxing in the pool, 2025

$6,500
"Picasso, St Christopher and the Philosopher", men by the ocean fishing, boats
Located in Edgartown, MA
Since summer 2004, I have lived in southern Italy, in the region of Puglia, the province of Bari, in a town called Altamura. A two-week restoration project of the Jesce Masseria brou...
Category

2010s Impressionist Massachusetts - Portrait Paintings

Materials

Oil, Canvas

"Picasso, St Christopher and the Philosopher", men by the ocean fishing, boats
"Picasso, St Christopher and the Philosopher", men by the ocean fishing, boats

Jennifer Bell
"Picasso, St Christopher and the Philosopher", men by the ocean fishing, boats, 2025

$4,400
"Old Madman 3", portrait, greys, browns, whites, collage, acrylic painting
By John Baker
Located in Natick, MA
John Baker’s “Old Madman #3”, an imaginary portrait 24 x 18 x 1.5 inches in flesh tones, greys, browns and whites, is from the artist’s important “Madman Series”. As Yeats wrote: “An...
Category

2010s Contemporary Massachusetts - Portrait Paintings

Materials

Canvas, Mixed Media, Acrylic

"Old Madman 3", portrait, greys, browns, whites, collage, acrylic painting
"Old Madman 3", portrait, greys, browns, whites, collage, acrylic painting

John Baker
"Old Madman 3", portrait, greys, browns, whites, collage, acrylic painting, 2020

$1,000
"The Ego and the Mechanisms of Defense", Contemporary, Portrait, Mixed Media
By John Baker
Located in Natick, MA
John Baker’s “The Ego and the Mechanism’s of Defense” is an acrylic painting on canvas with collage 20 x 16 inches in beige, blues, greens and ochres. The painting borrows its title from Anna Freud...
Category

2010s Contemporary Massachusetts - Portrait Paintings

Materials

Canvas, Mixed Media, Acrylic

"The Ego and the Mechanisms of Defense", Contemporary, Portrait, Mixed Media
"The Ego and the Mechanisms of Defense", Contemporary, Portrait, Mixed Media

John Baker
"The Ego and the Mechanisms of Defense", Contemporary, Portrait, Mixed Media, 2021

$1,200
"Down he Goes I", contemporary, portrait, male, grey, collage, acrylic painting
By John Baker
Located in Natick, MA
John Baker’s “Down he Goes I,” an acrylic painting on canvas with collage 20 x 16 inches in greys, greens and earth tones, is from the artist’s new “Fall of the White Male Series.” T...
Category

2010s Contemporary Massachusetts - Portrait Paintings

Materials

Canvas, Mixed Media, Acrylic

"Down he Goes I", contemporary, portrait, male, grey, collage, acrylic painting
"Down he Goes I", contemporary, portrait, male, grey, collage, acrylic painting

John Baker
"Down he Goes I", contemporary, portrait, male, grey, collage, acrylic painting, 2021

$1,400
"Good Catch" oil painting of a fisherwoman in orange waders holding large fish.
By Debbie Miller
Located in Edgartown, MA
A Rhode Island native, I earned a BFA from Rhode Island School of Design. Since then I’ve worked as a freelance artist, decorative painter, teacher and master painter at a folk art c...
Category

2010s Contemporary Massachusetts - Portrait Paintings

Materials

Canvas, Oil

"Good Catch" oil painting of a fisherwoman in orange waders holding large fish.

Debbie Miller
"Good Catch" oil painting of a fisherwoman in orange waders holding large fish., 2024

$4,000
"Domestic Dispute", contemporary, collage, woman, man, blue, red, mixed media
By John Baker
Located in Natick, MA
John Baker’s “Domestic Dispute”, an acrylic painting on canvas with collage, 48 x 36 x 1.5 inches in blues and flesh tones with red and white accents, depicts a violent moment in a b...
Category

2010s Contemporary Massachusetts - Portrait Paintings

Materials

Canvas, Mixed Media, Acrylic

"Domestic Dispute", contemporary, collage, woman, man, blue, red, mixed media
"Domestic Dispute", contemporary, collage, woman, man, blue, red, mixed media

John Baker
"Domestic Dispute", contemporary, collage, woman, man, blue, red, mixed media, 2018

$1,900
"Face Your Fears" Two side profiles staring into each other, surrounded by color
By Affen Segun
Located in Edgartown, MA
Affen Segun was born in 1993 in Lagos, Nigeria. A native of Bayelsa State, he discovered his love for art at a young age, and later got enrolled in a roadside art shop to start to ho...
Category

2010s Contemporary Massachusetts - Portrait Paintings

Materials

Fabric, Canvas, Acrylic

"Face Your Fears" Two side profiles staring into each other, surrounded by color

Affen Segun
"Face Your Fears" Two side profiles staring into each other, surrounded by color, 2024

$3,300
"Siblings: An Imaginary Portrait", contemporary, collage, acrylic painting
By John Baker
Located in Natick, MA
John Baker’s “Siblings: An Imaginary Portrait” is an acrylic painting on canvas with collage 11 x 9 x 1.5 inches in pinks, blues and whites. A quintessential image of gender, the pai...
Category

2010s Contemporary Massachusetts - Portrait Paintings

Materials

Canvas, Mixed Media, Acrylic

"Siblings: An Imaginary Portrait", contemporary, collage, acrylic painting
"Siblings: An Imaginary Portrait", contemporary, collage, acrylic painting

John Baker
"Siblings: An Imaginary Portrait", contemporary, collage, acrylic painting, 2019

$800
"Thumbs Up", contemporary, portrait, brown, grey, collage, acrylic painting
By John Baker
Located in Natick, MA
John Baker’s “Thumbs Up” is an acrylic painting on canvas with collage, 20 x 16 x 1.5 inches, in greys, lavenders, browns and flesh tones. The upbeat meaning...
Category

2010s Contemporary Massachusetts - Portrait Paintings

Materials

Canvas, Mixed Media, Acrylic

"Thumbs Up", contemporary, portrait, brown, grey, collage, acrylic painting
"Thumbs Up", contemporary, portrait, brown, grey, collage, acrylic painting

John Baker
"Thumbs Up", contemporary, portrait, brown, grey, collage, acrylic painting, 2020

$1,550
Dancer in Green
By Louis Kronberg
Located in Sheffield, MA
Louis Kronberg American, 1872-1965 Dancer in Green Pastel on board 14 by 21 in, w/ frame 20 ½ by 27 ½ in Signed lower right Louis Kronberg, a popular portraitist of the early 20th ...
Category

Early 20th Century Impressionist Massachusetts - Portrait Paintings

Materials

Pastel

Dancer in Green
Dancer in Green

Louis Kronberg
Dancer in Green

$3,800
She Blooms, Original Painting
By Diana Rosa
Located in San Francisco, CA

Artist Comments
A surreal palm landscape features a stylized woman with heart-shaped sunglasses. Her form blends seamlessly with the surrounding vegetation. She extends her s...

Category

21st Century and Contemporary Surrealist Massachusetts - Portrait Paintings

Materials

Acrylic

She Blooms, Original Painting
She Blooms, Original Painting

Diana Rosa
She Blooms, Original Painting, 2024

$1,175
"Man of the World", contemporary, portrait, acrylic, mixed media, painting
By John Baker
Located in Natick, MA
John Baker’s “Man of the World”, an acrylic painting on canvas with collage, an imaginary portrait 27.5 x 21 inches, in muted neutral tones highlighted by lemon and golden yellows and chalky reds, is from the artist’s “Mask” series...
Category

2010s Contemporary Massachusetts - Portrait Paintings

Materials

Canvas, Mixed Media, Acrylic

"Man of the World", contemporary, portrait, acrylic, mixed media, painting
"Man of the World", contemporary, portrait, acrylic, mixed media, painting

John Baker
"Man of the World", contemporary, portrait, acrylic, mixed media, painting, 2013

$2,400
"Flute Player", contemporary, portrait, orange, green, collage, acrylic painting
By John Baker
Located in Natick, MA
John Baker’s “Flute Player” is a contemporary acrylic painting on canvas with collage. The portrait is 20 x 16 x 1.5 inches in flesh tones, oranges, greens and browns. The detail and...
Category

2010s Contemporary Massachusetts - Portrait Paintings

Materials

Canvas, Mixed Media, Acrylic

"Flute Player", contemporary, portrait, orange, green, collage, acrylic painting
"Flute Player", contemporary, portrait, orange, green, collage, acrylic painting

John Baker
"Flute Player", contemporary, portrait, orange, green, collage, acrylic painting, 2020

$900
"Old Man Releasing a Caged Bird", acrylic, portrait, collage, blue, brown
By John Baker
Located in Natick, MA
John Baker’s “Old Man Releasing a Caged Bird” is an imaginary portrait painting, acrylic on canvas with collage, 24 x 18 x 1.5 inches in browns, blues and f...
Category

2010s Contemporary Massachusetts - Portrait Paintings

Materials

Canvas, Mixed Media, Acrylic

"Old Man Releasing a Caged Bird", acrylic, portrait, collage, blue, brown
"Old Man Releasing a Caged Bird", acrylic, portrait, collage, blue, brown

John Baker
"Old Man Releasing a Caged Bird", acrylic, portrait, collage, blue, brown, 2020

$1,900
"Shooting the Rapids", Contemporary, Portrait, Blue, Collage, Acrylic Ppainting
By John Baker
Located in Natick, MA
John Baker’s “Shooting the Rapids” is an acrylic painting on canvas with collage 48.5 x 36 inches in rich blues with auburn and red counterpoints and highlights. The young woman’s mood of contemplative reverie contrasts with the pleased and excited feelings of the helmeted crew. Obviously relieved, they float in their white water raft...
Category

2010s Contemporary Massachusetts - Portrait Paintings

Materials

Canvas, Mixed Media, Acrylic

"Shooting the Rapids", Contemporary, Portrait, Blue, Collage, Acrylic Ppainting
"Shooting the Rapids", Contemporary, Portrait, Blue, Collage, Acrylic Ppainting

John Baker
"Shooting the Rapids", Contemporary, Portrait, Blue, Collage, Acrylic Ppainting, 2019

$2,700
"Masks of a Novelist: An Imaginary Portrait of Tom Wolfe", acrylic, painting
By John Baker
Located in Natick, MA
John Baker’s “Masks of a Novelist: An Imaginary Portrait of Tom Wolfe”, a 42 x 32 x 1.5 inch acrylic painting with collage on canvas, is not so much a depiction of Tom Wolfe’s appear...
Category

2010s Contemporary Massachusetts - Portrait Paintings

Materials

Canvas, Mixed Media, Acrylic

"Masks of a Novelist: An Imaginary Portrait of Tom Wolfe", acrylic, painting
"Masks of a Novelist: An Imaginary Portrait of Tom Wolfe", acrylic, painting

John Baker
"Masks of a Novelist: An Imaginary Portrait of Tom Wolfe", acrylic, painting, 2017

$3,100
The Calm.
By Clarence James
Located in Boston, MA
Artist: James, Clarence Title: The Calm. Date: 2025 Medium: Acrylic, Aerosol, Oil Stick on Canvas Unframed Dimensions: 40" x 30" x 1.5" Signature: Signed Edition: Unique
Category

2010s Contemporary Massachusetts - Portrait Paintings

Materials

Oil, Spray Paint, Acrylic

The Calm.
The Calm.

Clarence James
The Calm., 2025

$5,400

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