diff --git a/src/metadata/MetadataStorage.ts b/src/metadata/MetadataStorage.ts
index 286346ac90..093d2852a1 100644
--- a/src/metadata/MetadataStorage.ts
+++ b/src/metadata/MetadataStorage.ts
@@ -3,6 +3,7 @@ import { ConstraintMetadata } from './ConstraintMetadata';
 import { ValidationSchema } from '../validation-schema/ValidationSchema';
 import { ValidationSchemaToMetadataTransformer } from '../validation-schema/ValidationSchemaToMetadataTransformer';
 import { getGlobal } from '../utils';
+import { ValidationTypes } from '../validation/ValidationTypes';
 
 /**
  * Storage all metadatas.
@@ -140,7 +141,11 @@ export class MetadataStorage {
       return !originalMetadatas.find(originalMetadata => {
         return (
           originalMetadata.propertyName === inheritedMetadata.propertyName &&
-          originalMetadata.type === inheritedMetadata.type
+          originalMetadata.type === inheritedMetadata.type &&
+          (originalMetadata.type !== ValidationTypes.CUSTOM_VALIDATION ||
+            (originalMetadata.name !== undefined || inheritedMetadata.name !== undefined
+              ? originalMetadata.name === inheritedMetadata.name
+              : originalMetadata.constraintCls === inheritedMetadata.constraintCls))
         );
       });
     });
diff --git a/test/functional/inherited-validation.spec.ts b/test/functional/inherited-validation.spec.ts
index 04254a9d3b..48a97b2d85 100644
--- a/test/functional/inherited-validation.spec.ts
+++ b/test/functional/inherited-validation.spec.ts
@@ -1,9 +1,144 @@
-import { Contains, MinLength } from '../../src/decorator/decorators';
+import {
+  Contains,
+  IsNotEmpty,
+  IsString,
+  MinLength,
+  Validate,
+  ValidatorConstraint,
+} from '../../src/decorator/decorators';
 import { Validator } from '../../src/validation/Validator';
+import { ValidationArguments } from '../../src/validation/ValidationArguments';
 
 const validator = new Validator();
 
 describe('inherited validation', () => {
+  it('should retain different validators on a redeclared property across inheritance levels', async () => {
+    class Base {
+      @IsString()
+      @MinLength(3)
+      title: string;
+    }
+    class Child extends Base {
+      @Contains('hello')
+      title: string;
+    }
+    class Grandchild extends Child {
+      @IsNotEmpty()
+      title: string;
+    }
+
+    const model = new Grandchild();
+    model.title = 'a';
+    const errors = await validator.validate(model);
+    expect(errors).toHaveLength(1);
+    expect(errors[0].constraints).toEqual({
+      contains: 'title must contain a hello string',
+      minLength: 'title must be longer than or equal to 3 characters',
+    });
+    model.title = '';
+    const emptyErrors = await validator.validate(model);
+    expect(emptyErrors).toHaveLength(1);
+    expect(emptyErrors[0].constraints).toEqual({
+      isNotEmpty: 'title should not be empty',
+      contains: 'title must contain a hello string',
+      minLength: 'title must be longer than or equal to 3 characters',
+    });
+    model.title = 'hello';
+    expect(await validator.validate(model)).toEqual([]);
+  });
+
+  it('should prefer the child constraints for the same named validator', async () => {
+    class Base {
+      @MinLength(10)
+      title: string;
+    }
+    class Child extends Base {
+      @MinLength(3)
+      title: string;
+    }
+
+    const model = new Child();
+    model.title = 'hello';
+    expect(await validator.validate(model)).toEqual([]);
+    model.title = 'a';
+    const errors = await validator.validate(model);
+    expect(errors).toHaveLength(1);
+    expect(errors[0].constraints).toEqual({ minLength: 'title must be longer than or equal to 3 characters' });
+  });
+
+  it('should retain different custom constraint classes and prefer child constraints for the same class', async () => {
+    @ValidatorConstraint({ name: 'startsWith' })
+    class StartsWith {
+      validate(value: string, args: ValidationArguments): boolean {
+        return value.startsWith(args.constraints[0]);
+      }
+    }
+    @ValidatorConstraint({ name: 'endsWith' })
+    class EndsWith {
+      validate(value: string, args: ValidationArguments): boolean {
+        return value.endsWith(args.constraints[0]);
+      }
+    }
+    class Base {
+      @Validate(StartsWith, ['base'])
+      @Validate(EndsWith, ['!'])
+      title: string;
+    }
+    class Child extends Base {
+      @Validate(StartsWith, ['child'])
+      title: string;
+    }
+
+    const model = new Child();
+    model.title = 'child';
+    const errors = await validator.validate(model);
+    expect(errors).toHaveLength(1);
+    expect(errors[0].constraints).toEqual({ endsWith: '' });
+    model.title = 'child!';
+    expect(await validator.validate(model)).toEqual([]);
+  });
+
+  it('should retain inherited custom constraints when the child adds a named validator', async () => {
+    @ValidatorConstraint({ name: 'hasHello' })
+    class HasHello {
+      validate(value: string): boolean {
+        return value.includes('hello');
+      }
+    }
+    class Base {
+      @Validate(HasHello)
+      title: string;
+    }
+    class Child extends Base {
+      @IsNotEmpty()
+      title: string;
+    }
+
+    const model = new Child();
+    model.title = 'world';
+    const errors = await validator.validate(model);
+    expect(errors).toHaveLength(1);
+    expect(errors[0].constraints).toEqual({ hasHello: '' });
+  });
+
+  it('should only override inherited validators in the selected group', async () => {
+    class Base {
+      @MinLength(10, { groups: ['base'] })
+      title: string;
+    }
+    class Child extends Base {
+      @MinLength(3, { groups: ['child'] })
+      title: string;
+    }
+
+    const model = new Child();
+    model.title = 'hello';
+    const errors = await validator.validate(model, { groups: ['base'] });
+    expect(errors).toHaveLength(1);
+    expect(errors[0].constraints).toEqual({ minLength: 'title must be longer than or equal to 10 characters' });
+    expect(await validator.validate(model, { groups: ['child'] })).toEqual([]);
+  });
+
   it('should validate inherited properties', () => {
     expect.assertions(9);