Raymond Caldwell

Raymond Caldwell obituary

Raymond Caldwell

Raymond Caldwell Obituary

Obituary published on Legacy.com by Davis Funeral Home - Roxbury on Feb. 4, 2026.
Raymond was born in Pittsburgh, Pennsylvania on February 3rd, 1944, to Alverna Yvonne Avery and John Henry Caldwell. He had 9 siblings: John Caldwell, Jimmy Caldwell, Joyce Quinerly, Joe Woodson, Melvin Woodson, Alvin Caldwell, Warren Caldwell, Lenard Woodson, and Rebecca Woodson.

Ray attended and graduated from Glad Stone High School.

Ray was a soft spoken, wise, understanding, kind- and open-hearted man. He would take the shirt off his back if you didn't have one, that was for everyone. He enjoyed singing, baking, grilling, dancing, and cleaning. He was very mechanical and always was prepared to help.

He was a giving person, always helping who he can at any given moment. Especially if he knew you. He was an amazing painter, he painted various places as he grew up, such as Harvard University and a few housing developments and apartments.

As he got older, in 2002, he started his daycare services. From that point he helped raise generations of children. "Don't make me get that soon" as "hard head makes a soft behind" were his sayings, that's how you knew you went to far.

He leaves behind his children: Mary Williams, Raezena Caldwell, Darnella Caldwell, Chante Hall, Ebony Clark, Nicole Hall, Raymond Caldwell Jr., and Nathalie Caldwell (daughter-in-law_ who will miss his dearly. He also leaves a host of grandchildren and great grandchildren who he loved dearly.

The family would like to extend a special thanks to Susie, Ronnie, and Mya for the compassion love and care they showed during his final days.

To send flowers to the family or plant a tree in memory of Raymond Caldwell, please visit our floral store.

To plant trees in memory, please visit the Sympathy Store.

Sign Raymond Caldwell's Guest Book

Not sure what to say?

February 16, 2026

Corey Allen posted to the memorial.

February 16, 2026

Benita Taylor posted to the memorial.

February 13, 2026

Stevia Brown posted to the memorial.

6 Entries

Corey Allen

February 16, 2026

Rest well Mr. Caldwell.

- Corey J. Allen

Benita Taylor

February 16, 2026

Peace and Blessings to the Caldwell Family. Ray will truly be missed. He was kind and open hearted to everyone. Humans and fur-babies. I remember when he helped me temporarily house my cats for me when I was in between places. In a secret place on Stanwood. May he rest in peace in the heavens with our Lord.

Stevia Brown

February 13, 2026

Rest in peace uncle ray

Tracy Grant

February 13, 2026

Raymond Caldwell - aka Raymo, Ray, and Uncle Ray

My God, this is such a tough loss.

You were never my father by blood, but you were my father in every way that truly mattered. Your guidance, kindness, and unwavering support helped shape the person I am today. I will carry your wisdom and your love with me for the rest of my life.

Thank you for being my mentor, my protector, and my friend. You will always hold a special place in my heart, and I will miss you more than words can express.

Raymo, as I called you, I´m going to miss our talks - especially on our birthdays and during the holidays.

May your legacy live on. Rest in peace

Much love,
Tracy Grant

David Williams

February 12, 2026

Uncle Ray was a great Man he will truly be miss

Susie Hall

February 11, 2026

Uncle Ray loved to get dress and make those icy for the kids and cook for the world! Uncle Ray loved the kids! I'm going to miss you Uncle Ray my grilling, daycare down home blues and oldies partner! At the end you was strong and stubborn ole man. You went out your way Ray"s way. We are going to miss you old man. But now your up there with the best get you rest. Love you Uncle Ray

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Davis Funeral Home - Roxbury

89 Walnut Avenue, Roxbury, MA 02119

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Sign Raymond Caldwell's Guest Book

Not sure what to say?

February 16, 2026

Corey Allen posted to the memorial.

February 16, 2026

Benita Taylor posted to the memorial.

February 13, 2026

Stevia Brown posted to the memorial.