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Massachusetts - Portrait Paintings

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Item Ships From: Massachusetts
Across the Universe, Original Painting
By Nava Lundy
Located in San Francisco, CA

Artist Comments
A young woman closes her eyes in serene reflection, holding a delicate pink flower against her face. The background, filled with flowing handwritten lyrics from...

Category

21st Century and Contemporary Contemporary Massachusetts - Portrait Paintings

Materials

Acrylic

It's Gonna Be a Long Night (98-99 Series), Original Painting
By Mark Cudd
Located in San Francisco, CA

Artist Comments
A young woman glances over her shoulder, her eyes radiating a mysterious gaze. She is out for the night, standing at an overlook of her town, taking in the view...

Category

21st Century and Contemporary Contemporary Massachusetts - Portrait Paintings

Materials

Acrylic

"African Diaspora" mixed media portrait of woman, gold headdress and graphic top
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 Massachusetts - Portrait Paintings

Materials

Resin, Mixed Media, Acrylic, Magazine Paper

"Wisdom" Contemporary portrait of black woman with white hair and floral crown.
Located in Edgartown, MA
Lily Sol’s current work “Flower Goddess” is a symbol of blooming into her true self and honoring the divine femine energy within all of us. Through her paintings she is able to celebrate the fierce women in her life and shine light on the diverse and unique beauty of cultures around the world. She loves exploring different mediums in her art journal, playing with collage, acrylic paints, watercolors, and pressed blooms. While painting she tries to stay in an intuitive mindset and allow her works to transform naturally—always seeking the harmony between staying loose yet in control, yin & yang of life. Bright colors, a playlist she can dance...
Category

2010s Massachusetts - Portrait Paintings

Materials

Canvas, Oil

"Maternal Love", Surrealist, Portrait, Pink, Blue, Collage, Acrylic Painting
By John Baker
Located in Natick, MA
John Baker’s “Maternal Love” is a 18 x 13 ¾ x 2 ¼ inch acrylic on canvas with collage in pinks, greens and blues. The nurturing mother gently kisses her near adolescent daughter; inn...
Category

2010s Surrealist Massachusetts - Portrait Paintings

Materials

Canvas, Acrylic

Fiona #1
Located in Denver, CO
Dave Seeley's "Fiona #1" is an original, handmade oil painting that depicts a female model holding purple velvet fabric tightly around her form to reveal the curves of her figure. ...
Category

21st Century and Contemporary Realist Massachusetts - Portrait Paintings

Materials

Canvas, Oil, Board

Fiona #1
Fiona #1
$4,780 Sale Price
20% Off
The Color of Music, Original Painting
By Robin Okun
Located in San Francisco, CA

Artist Comments
Bold shapes and vibrant colors depict a bass player in a lively, home-like setting. The interplay of shape, color, and line creates a sense of playful rhythm, e...

Category

21st Century and Contemporary Contemporary Massachusetts - Portrait Paintings

Materials

Acrylic

"Regression and Development", Surrealist, Portrait, Collage, Acrylic Painting
By John Baker
Located in Natick, MA
John Baker’s “Regression and Development” is an acrylic painting on canvas with collage in tans and browns with red and yellow accents. Although the painting depicts a smiling young ...
Category

2010s Surrealist Massachusetts - Portrait Paintings

Materials

Canvas, Mixed Media, Acrylic

"wRapt" by Dave Seeley, Oil Painting
Located in Denver, CO
Dave Seeley's (US based) "wRapt" is an original, handmade oil painting that depicts a female model, in a white dress, reclining. Dave Seeley is a figure painter living in Boston, M...
Category

2010s Contemporary Massachusetts - Portrait Paintings

Materials

Canvas, Oil, Board

Donna Isham Gold Portrait Face Female Bright Colors Abstract Figurative Blue
Located in Nantucket, MA
Pheobe is part of a series of abstract portraits Donna Isham created in 2022. Bold brush strokes and the use of brilliant colors form into confident and strong female images.
Category

2010s Abstract Massachusetts - Portrait Paintings

Materials

Acrylic

She's Got Your Number, Mister (98-99 Series), Original Painting
By Mark Cudd
Located in San Francisco, CA

Artist Comments
A man stands still, his eyes hidden in the shadow of his hat. The lack of a visible gaze adds mystery to the scene. He is a visualization of someone whose voice...

Category

21st Century and Contemporary Realist Massachusetts - Portrait Paintings

Materials

Acrylic

"Circles of Life" African woman wearing blue circle earrings and black robe
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 these self discoveries take us in surprising directions. We must gain strength from what we learn from each other as well as listen to that persistent, ever present, intuitive self. The connection of one’s own rich heritage and person growth will travel into the inevitable and critical connection between African Americans and Africa. These connections are rich and very important. They Exist! My work, I hope, will serve as a creative connection between the African diaspora and western culture. It is this connection that cause my creative forces to react." Janice Frame...
Category

2010s Massachusetts - Portrait Paintings

Materials

Mixed Media, Resin, Acrylic, Magazine Paper

Anne Hathaway and Brooklyn Fish
By William Nelson
Located in Greenwich, CT
The intention of this work is to generate conversations about values and identity by assembling unlikely pairs, Hollywood film icons and nostalgic comic book environments. Each entit...
Category

2010s Contemporary Massachusetts - Portrait Paintings

Materials

Canvas, Oil

Stand Out
By Clarence James
Located in Boston, MA
Artist: James, Clarence Title: Stand Out 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

Tea Time, Original Painting
Located in San Francisco, CA

Artist Comments
Inspired by Carey Park's photos from her visits to France, this painting captures two people savoring tea in a sunlit room. Seated comfortably, they appear ab...

Category

21st Century and Contemporary Contemporary Massachusetts - Portrait Paintings

Materials

Acrylic

"Sisi Black and Shine II" Acrylic portrait of Black woman with blue background
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 Massachusetts - Portrait Paintings

Materials

Fabric, Canvas, Acrylic

"Terrace Over Nice" figurative painting of a woman by the ocean, France
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

"Bubblegum Girl", Contemporary Portrait, Pink, Nude, Collage, Acrylic Painting
By John Baker
Located in Natick, MA
John Baker’s “Bubblegum Girl” is an acrylic painting on canvas with collage 72 x 42 x 1.5 inches in pinks, greens and flesh tones. The bright pink of th...
Category

2010s Contemporary Massachusetts - Portrait Paintings

Materials

Canvas, Mixed Media, Acrylic

"AI Takes Over", Surrealist, Portrait, Brown, Black, Collage, Acrylic Painting
By John Baker
Located in Natick, MA
John Baker’s “AI Takes Over” is a 20 x 16 x 1.5 inch acrylic painting on canvas with collage in greys, blacks, browns and pinks. The impending excessive reliance on AI (for informati...
Category

2010s Surrealist Massachusetts - Portrait Paintings

Materials

Canvas, Acrylic, Mixed Media

January 2, 1998 (98-99 Series), Original Painting
By Mark Cudd
Located in San Francisco, CA

Artist Comments
1998–1999 marked a particularly tumultuous chapter for artist Mark Cudd. In this first installment of a 50-image series, he attempts to construct an honest ac...

Category

21st Century and Contemporary Contemporary Massachusetts - Portrait Paintings

Materials

Acrylic

March 9, 1998 (98-99 Series), Original Painting
By Mark Cudd
Located in San Francisco, CA

Artist Comments
A woman glances sharply to her right, her expression poised between curiosity and caution. Rendered in stark black and white, the piece gives a timeless and cin...

Category

21st Century and Contemporary Realist Massachusetts - Portrait Paintings

Materials

Acrylic

Lazarus, Oil Painting
By David Shepherd
Located in San Francisco, CA

Artist Comments
Bright pink petals frame a close-up portrait. For artist David Shepherd, the eye—like a fingerprint—uniquely identifies a person, yet their identity, orig...

Category

21st Century and Contemporary Realist Massachusetts - Portrait Paintings

Materials

Oil

Transcending Boundaries, Oil Painting
By Gary Leonard
Located in San Francisco, CA

Artist Comments
Artist Gary Leonard presents a portrait of a woman that celebrates existence. "The painting crosses and extends the boundaries of life into an emotionally exc...

Category

21st Century and Contemporary Contemporary Massachusetts - Portrait Paintings

Materials

Oil

"Pedestal" by Dave Seeley, Nude Female
Located in Denver, CO
Dave Seeley's "Pedestal" (2023) is a striking original oil on canvas painting. The nude female figure sits atop a rock formation, her contemplative pose and the warm, ethereal light ...
Category

21st Century and Contemporary Massachusetts - Portrait Paintings

Materials

Canvas, Oil, Board

"Masquerade" Oil Painting
Located in Denver, CO
Dave Seeley's (US based) "Dawn #5 Masquerade" is an original, handmade oil painting that depicts a female model looking over her shoulder as her dark hair curtains her face.
Category

2010s Contemporary Massachusetts - Portrait Paintings

Materials

Canvas, Oil, Board

Room for Dessert, Original Painting
By Nava Lundy
Located in San Francisco, CA

Artist Comments
A woman savors a moment of sweetness alongside a delectable strawberry cake. The rich textures, warm tones, and striking composition create a sense of bold el...

Category

21st Century and Contemporary Contemporary Massachusetts - Portrait Paintings

Materials

Acrylic

"Southern Belle: An Imaginary Portrait", woman, pastel, pink, acrylic painting
By John Baker
Located in Natick, MA
John Baker’s “Southern Belle: An Imaginary Portrait”, a 43 x 32 x 1.5 inch acrylic painting with collage on canvas is from the artist’s Socialite series...
Category

2010s Contemporary Massachusetts - Portrait Paintings

Materials

Canvas, Mixed Media, Acrylic

Portrait 25-10, Original Painting
Located in San Francisco, CA

Artist Comments
Blue, green, and metallic gold dots form a woman's face, wearing a solemn expression and intense gaze. Artist Hyoungseok Kim painted this piece using pointill...

Category

21st Century and Contemporary Contemporary Massachusetts - Portrait Paintings

Materials

Acrylic

White Chair, Original Painting
Located in San Francisco, CA

Artist Comments
A woman sits on a white wooden chair, gazing into the distance. Her posture and expression exude a calm, peaceful feeling. The minimalist composition and bold b...

Category

21st Century and Contemporary Contemporary Massachusetts - Portrait Paintings

Materials

Acrylic

Doll Hut, Original Painting
Located in San Francisco, CA

Artist Comments
Artist John McCabe paints three punk rockers standing near a hot pink house-shaped signage that offers free beer. The World Famous Doll Hut dates back to the ...

Category

21st Century and Contemporary Pop Art Massachusetts - Portrait Paintings

Materials

Acrylic

One Must Shimmer, Oil Painting
By Mary Pratt
Located in San Francisco, CA

Artist Comments
Artist Mary Pratt paints an ethereal figure with a billowing gossamer white skirt. The woman gazes through a sea of floating lights, framing her and spilling ...

Category

21st Century and Contemporary Contemporary Massachusetts - Portrait Paintings

Materials

Oil

"Surprise in the Garden", Surrealist, Collage, Acrylic Painting, 2008
By John Baker
Located in Natick, MA
John Baker’s “Surprise in the Garden” is an acrylic painting on canvas with collage 31 ½ x 28 ¼ inches brightly colored in greens, blues, oranges, rose and russet, and cream. Little ...
Category

Early 2000s Surrealist Massachusetts - Portrait Paintings

Materials

Canvas, Mixed Media, Acrylic

Portrait 25-3, Original Painting
Located in San Francisco, CA

Artist Comments
A woman lifts her hand to her head, her fingers gracefully weaving through her hair. Artist Hyoungseok Kim painted this piece using pointillism. He emphasizes...

Category

21st Century and Contemporary Contemporary Massachusetts - Portrait Paintings

Materials

Acrylic

Portrait 25-1, Original Painting
Located in San Francisco, CA

Artist Comments
A woman places her hand on her head. Different-colored and metallic green dots form her face, hair, and clothing. The smooth, untextured background enhances h...

Category

21st Century and Contemporary Contemporary Massachusetts - Portrait Paintings

Materials

Acrylic

Portrait 25-8, Original Painting
Located in San Francisco, CA

Artist Comments
Tiny, multicolored dots form the portrait of a woman, her features subtly emerging from a dark background. Green, blue, and metallic gold define her face. Art...

Category

21st Century and Contemporary Contemporary Massachusetts - Portrait Paintings

Materials

Acrylic

Portrait 25-9, Original Painting
Located in San Francisco, CA

Artist Comments
Multicolored and metallic dots shape a woman's face, her features appearing subtly against a dark background. Her expression carries a quiet intensity. Artist...

Category

21st Century and Contemporary Contemporary Massachusetts - Portrait Paintings

Materials

Acrylic

Portrait 25-2, Original Painting
Located in San Francisco, CA

Artist Comments
Different-colored and metallic blue dots define a woman's portrait, the solid background emphasizing her textured form. Artist Hyoungseok Kim painted this pie...

Category

21st Century and Contemporary Contemporary Massachusetts - Portrait Paintings

Materials

Acrylic

"The Art Critic" portrait of a man in the suit in front of the cactuses
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

"The Muse in Nice" figurative painting of a woman in France by the water, ocean
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

"Ethnic Meld #3", Surrealist, Portrait, Pink, Collage, Acrylic Painting, 2008
By John Baker
Located in Natick, MA
John Baker’s “Ethnic Meld #3” is an acrylic painting on canvas with collage 17.75 x 15.75 inches in pinks, reds and ochers. The noted American painter George Tooker (1920-2011), hims...
Category

Early 2000s Surrealist Massachusetts - Portrait Paintings

Materials

Canvas, Acrylic

Love Language, Original Painting
By Nava Lundy
Located in San Francisco, CA

Artist Comments
A chic woman wears an alluring expression. Surrounded by roses and gold accents, she echoes the bold yet delicate energy of the flowers. The painting employs ...

Category

21st Century and Contemporary Contemporary Massachusetts - Portrait Paintings

Materials

Acrylic

"Lighthouse Maiden" redheaded mermaid blows a kiss to the cliffs on the coast
By Fred Calleri
Located in Edgartown, MA
Fred Calleri was born in Maryland and has slowly moved westward towards his current home in Santa Barbara, California. On his way, he earned an Illustration and Graphic Design degree...
Category

2010s Contemporary Massachusetts - Portrait Paintings

Materials

Canvas, Oil

Autumn Evening Reverie, Original Painting
By Libby Ramage
Located in San Francisco, CA

Artist Comments
Artist Libby Ramage presents an autumnal scene marked by large leaves falling from the sky. "As the sun fades, a young boy becomes the man," says Libby. Showi...

Category

21st Century and Contemporary Outsider Art Massachusetts - Portrait Paintings

Materials

Acrylic

"Poetry and Painting", Surrealist, Reds, Blues, Collage, Acrylic Painting, 2018
By John Baker
Located in Natick, MA
John Baker’s “Poetry and Painting” is an acrylic painting on canvas with collage 21 x 18.75 inches in reds, blues, greys and pinks. In this image the sister arts of poetry and painti...
Category

2010s Surrealist Massachusetts - Portrait Paintings

Materials

Canvas, Acrylic

14th Street Station - Oakland, Original Painting
Located in San Francisco, CA

Artist Comments
Artist John McCabe presents a diverse set of people crowding in a terminal. He pictures them in his signature graphic style of pop ...

Category

21st Century and Contemporary Pop Art Massachusetts - Portrait Paintings

Materials

Acrylic

"Dressing the Sewing Dummy", Surrealist, Collage, Acrylic Painting, 2018
By John Baker
Located in Natick, MA
John Baker’s “Dressing the Sewing Dummy” is an acrylic painting on canvas with collage 38 x 20 inches by .75 inch in reds, yellows, blues and purples. A young seamstress is elated by...
Category

2010s Surrealist Massachusetts - Portrait Paintings

Materials

Canvas, Acrylic

Flamingo Chair, Original Painting
By Diana Rosa
Located in San Francisco, CA

Artist Comments
A woman in a red dress lounges on a green chair adorned with two stylized flamingos. Large, bold leaves surround her as she gazes forward. Her red sunglasses ...

Category

21st Century and Contemporary Surrealist Massachusetts - Portrait Paintings

Materials

Acrylic

Rehearsal Dinner, Original Painting
Located in San Francisco, CA

Artist Comments
Three figures wearing matching suits, ties, and shirts evoke the vision of what artist John McCabe imagines a 1973 rehearsal dinner might have looked like. Su...

Category

21st Century and Contemporary Pop Art Massachusetts - Portrait Paintings

Materials

Acrylic

"Wedding Party on the River" men on the river drinking, wedding, party, boat
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

"Man Adjusting his Tie", surrealist, green, red, blue, yellow, acrylic painting
By John Baker
Located in Natick, MA
John Baker’s “Man Adjusting his Tie” is an acrylic painting on canvas 24 x 18 inches in greens and reds with blue and yellow color accents. The disheveled appearance of the man impli...
Category

2010s Surrealist Massachusetts - Portrait Paintings

Materials

Canvas, Acrylic

Blue Rhapsody, Oil Painting
By Gary Leonard
Located in San Francisco, CA

Artist Comments
A woman poses with an expression of wonder and intrigue. She wears a delicate pink dress adorned with floral patterns. The big white strokes imbue the scene w...

Category

21st Century and Contemporary Contemporary Massachusetts - Portrait Paintings

Materials

Oil

"Maidenhood and Expectancy: Two Studio Sketches of Felicia", Surrealist, Acrylic
By John Baker
Located in Natick, MA
John Baker’s “Maidenhood and Expectancy: Two Studio Sketches of Felicia” is a pair of matching paintings 23.25 x 22.75 inches and 24 x 20 inches in greys, whites, pinks and blacks. B...
Category

2010s Surrealist Massachusetts - Portrait Paintings

Materials

Canvas, Acrylic

Hunt Slonem "Queen Elizabeth" Portrait
By Hunt Slonem
Located in Boston, MA
Artist: Slonem, Hunt Title: Queen Elizabeth Date: 2025 Medium: Oil on wood Unframed Dimensions: 20" x 16" Framed Dimensions: 26" x 21.5" Signature: Signed by Artist on Verso E...
Category

2010s Contemporary Massachusetts - Portrait Paintings

Materials

Oil

Hunt Slonem "Green Abe" Lincoln Portrait
By Hunt Slonem
Located in Boston, MA
Artist: Slonem, Hunt Title: Green Abe Date: 2023 Medium: Oil on wood Unframed Dimensions: 20" x 16" Framed Dimensions: 23.5" x 19.5" Signature: Signed by Artist on Verso Editi...
Category

2010s Contemporary Massachusetts - Portrait Paintings

Materials

Oil

"Music Makers", Contemporary, Figures, Brown, Collage, Acrylic Painting, 2023
By John Baker
Located in Natick, MA
John Baker’s “Music Makers” is an acrylic painting on canvas with collage 30 inches x 40 inches in blues, oranges, pinks, yellows and browns. The image is accomplished in contrasting...
Category

2010s Contemporary Massachusetts - Portrait Paintings

Materials

Canvas, Mixed Media, Acrylic

"Self Chaperone", Surrealist, Portrait, Mixed Media Acrylic Painting, 2020
By John Baker
Located in Natick, MA
John Baker’s “Self-Chaperone” is an acrylic painting on canvas with collage 28 x 22 inches in flesh tones, yellows and greys. The portrait depicts the inner conflict between uninhibi...
Category

2010s Surrealist Massachusetts - Portrait Paintings

Materials

Canvas, Mixed Media, Acrylic

The Pause, Original Painting
Located in San Francisco, CA

Artist Comments
This painting captures a moment of quiet deliberation. A stunning woman with thick, lustrous hair gazes thoughtfully toward an unseen companion, her expressio...

Category

21st Century and Contemporary Outsider Art Massachusetts - Portrait Paintings

Materials

Acrylic

The Giver
By Clarence James
Located in Boston, MA
Artist: James, Clarence Title: The Giver Date: 2025 Medium: Acrylic, Aerosol, Oil Stick on Canvas Unframed Dimensions: 20" x 20" Signature: Signed Edition: Unique
Category

2010s Contemporary Massachusetts - Portrait Paintings

Materials

Oil, Spray Paint, Acrylic

Ghost in the City - Police, Original Painting
Located in San Francisco, CA

Artist Comments
Artist Hyoungseok Kim paints three police officers on the street in New York City with his signature style of pointillism. He emphasizes the material and scie...

Category

21st Century and Contemporary Contemporary Massachusetts - Portrait Paintings

Materials

Acrylic

"Eating at the Airline Diner", surrealist, red, blue, yellow, acrylic painting
By John Baker
Located in Natick, MA
John Baker’s “Eating at the Airline Diner” is an acrylic on canvas with collage 30 x 30 inches in reds, yellows and blues with green accents. The iconic diner, in Queens, New York, i...
Category

2010s Surrealist Massachusetts - Portrait Paintings

Materials

Canvas, Acrylic, Mixed Media

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