Program.cs

using Microsoft.EntityFrameworkCore;
using NetTopologySuite.Geometries;
using NetTopologySuite.IO;
using System;
using System.ComponentModel.DataAnnotations;

namespace ntsbug
{
    class Program
    {
        static void Main(string[] args)
        {
            using (var db = dbContext.Create())
            {
                var region1 = new Region();
                region1.Boundaries = (Geometry)new WKTReader().Read("POLYGON((20.381011962891 -1.8992614746094, 20.271148681641 -1.9720458984375, 20.449676513672 -2.010498046875, 20.397491455078 -1.9377136230469, 20.381011962891 -1.8992614746094))");
                db.Entry(region1).State = EntityState.Added;
                db.SaveChanges();

                var region2 = new Region();
                region2.Boundaries = (Geometry)new WKTReader().Read("POLYGON ((30.613919943000042 -30.391359940999962, 30.612469943000065 -30.390529940999954, 30.61038994300003 -30.389329940999971, 30.610309943000061 -30.389279940999984, 30.609699943000066 -30.388919940999983, 30.608319943000026 -30.388159940999969, 30.607720068000049 -30.387609940999937, 30.608249943000033 -30.386529940999935, 30.609559943000079 -30.383849940999937, 30.610149943000067 -30.382649940999954, 30.61065994300003 -30.381609940999965, 30.611987068000076 -30.37889519099997, 30.612189943000033 -30.378480065999952, 30.612269943000058 -30.378330065999933, 30.612819943000034 -30.377199940999958, 30.613505943000064 -30.375792940999929, 30.613989943000036 -30.374799940999935, 30.614940068000067 -30.372869940999976, 30.617439943000079 -30.368179940999937, 30.618999943000063 -30.365249940999945, 30.61904994300005 -30.365150065999956, 30.619459943000038 -30.364389940999956, 30.621169943000041 -30.362249940999959, 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30.61176994300007 -30.399249940999937, 30.611989943000026 -30.398339940999961, 30.613919943000042 -30.391359940999962))");
                db.Entry(region2).State = EntityState.Added;
                db.SaveChanges(); // <--- errors here

            }
        }
    }

    class dbContext: DbContext
    {
        public DbSet<Region> Regions { get; set; }

        public dbContext(DbContextOptions<dbContext> options) : base(options)
        {
            Database.EnsureCreated();
        }

        public static dbContext Create()
        {
            var builder = new DbContextOptionsBuilder<dbContext>();
            builder.UseSqlServer("Server=localhost;Database=ntsbug;Trusted_Connection=True;MultipleActiveResultSets=true;", o => o.UseNetTopologySuite());
            return new dbContext(builder.Options);
        }

        protected override void OnModelCreating(ModelBuilder modelBuilder)
        {
            modelBuilder.Entity<Region>().Property(e => e.Boundaries).HasColumnType("geometry");
            base.OnModelCreating(modelBuilder);
        }
    }

    public class Region
    {
        [Key, Required]
        public Guid RegionId { get; set; }
        public Geometry Boundaries { get; set; }

        public Region()
        {
            RegionId = Guid.NewGuid();
        }
    }
}